Supercritical Fluid Chromatography and Extraction

Anal. Chem.
1998, 70, 301R-319R
Supercritical Fluid Chromatography and Extraction

T. L. Chester,* J. D. Pinkston, and D. E. Raynie
Miami Valley Laboratories, The Procter & Gamble Company, P.O. Box 538707, Cincinnati, Ohio 45253-8707
Downloaded by ECOPETROL SA INST COLOMBIANO DE PETROLEO ICP on October 27, 2009 | http://pubs.acs.org
Publication Date (Web): May 15, 1998 | doi: 10.1021/a1980017d
Review Contents
Fluid Behavior and Physicochemical Measurements
Supercritical Fluid Chromatography
Theory, Fundamentals, and Comparisons
Stationary Phases and Columns
SFC Instrumentation, Techniques, and
Performance
SFC Detectors
SFC/MS
SFC Applications
Supercritical Fluid Extraction
Instrumentation, Techniques, and Performance
Solute Collection
Extracting Fluids
SFE-Coupled Techniques
SFE Applications
Pressurized Fluid Extraction
Literature Cited
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This critical review covers the literature appearing since our

last review (1) and reported in Chemical Abstracts through October
1997, articles appearing in the Journal of Chromatography through
volume 785, and several other recent works not yet abstracted.
We have been more selective than in the past, focusing on what
we believe are the most significant articles generally available to
readers throughout the world.
We agree with numerous critics that mystique surrounding
the word supercritical may have negatively influenced progress
in these areas. The strict definition of a supercritical fluid (that
is, a fluid at a pressure and temperature exceeding the critical
values) does not really apply to much of the work done that
requires supercritical fluid chromatography (SFC) and supercritical fluid extraction (SFE) equipment and techniques. For
example, liquid water has been used up to 300 C by applying
enough pressure (or restriction) to the column outlet to prevent
boiling (2-5). At this temperature, water, without additional
modifier, easily dissolves and transports numerous nonpolar
solutes not appreciably soluble in water at ambient temperature.
The key feature differentiating SFC and related techniques from
conventional techniques is the use of significantly elevated
pressure at the column outlet. This allows us not only to use
mobile phases that are either impossible or impractical under
conventional LC and GC conditions but also to use more ordinary
fluids at temperatures off limits at ambient pressure. These
capabilities provide truly significant advances in speed and
selectivity. A parallel relationship exists between SFE and related
hyperbaric extraction techniques compared with conventional
extraction techniques.
Because of the confusion and unnecessary limitation implied
by the term supercritical, we prefer the term unified chromatogS0003-2700(98)00017-1 CCC: $15.00
Published on Web 05/15/1998
1998 American Chemical Society
raphy to signify techniques performed with control of the column

outlet pressure and the column temperature, regardless of the
fluid state of the mobile phase (6). In this convention, LC and
GC are limiting behaviors of the more general unified description.
High-temperature LC, subcritical fluid chromatography (SubFC),
enhanced-fluidity liquid chromatography, SFC, and solvating gas
chromatography combine without boundaries to form the complete picture of unified chromatography when mobile-phase
properties are considered. Again, a similar case can be made for
extraction.
Unfortunately, there is no agreement yet regarding exactly
what else is unified. For example, should electroosmotic flow be
included in the definition along with pressure-driven flow? There
is no theoretical reason that a switch between GC, SFC, and LC
modes cannot be done without a discontinuity within a single
chromatographic procedure. However, Tong et al. was successful
using a mode-switching chromatograph to perform unified chromatography on samples with wide variation in volatility of
components (7). Discontinuously changing the mobile phase
should probably be viewed analogously with step gradients in LC
or ballistic heating in GC and, thus, should not introduce any new
controversy. Unified chromatography will be subject to debate
for the next few years, with the next installment scheduled for
the National ACS meeting in Boston, August 23-27, 1998. In the
meantime, we will continue to include all sorts of elevated-outletpressure techniques in our literature searches whether strictly
supercritical or not. We will call the techniques SFC or SFE here
when necessary to match the usage in the cited references.
People completely new to the fields of SFC, SFE, and the
related unified techniques might consider reading a recent review
article (8-13). Additional reviews focusing on more specific
topics are cited throughout this report.
FLUID BEHAVIOR AND PHYSICOCHEMICAL
MEASUREMENTS
SFC and SFE techniques can be used to determine a variety
of solute behaviors in fluids. Yang and Griffiths predicted
solubilities of solutes in supercritical CO2 from observations of
SFC retention (14). Condo et al. used inverse SFC to measure
partition coefficients of solutes between CO2 and silicone stationary
phases (15). Lou et al. used SFC data to predict SFE extraction
efficiency (16). Two dissertations deal with solubility and
chromatographic behavior (17) and with phase behavior (18).
Much additional work has been published on phase behavior,
diffusion rates, solubilities, etc., but we elected not to include any
of it here if not using or referring directly to SFC- or SFE-like
techniques.
Analytical Chemistry, Vol. 70, No. 12, June 15, 1998 301R
SUPERCRITICAL FLUID CHROMATOGRAPHY

There are two new books focusing on packed-column SFC
(pcSFC). Berger focused on practical matters regarding SFC
analyses of samples such as pharmaceuticals and agrochemicals
(19), while Anton and Berger edited a volume aimed at industrial
applications of SFC but including information on new fundamental
discoveries and techniques (20).
In our last review we commented on the high price of SFC
instrumentation at that time and on the general disinterest among
some suppliers to adopt significant, proven improvements in
capabilities and techniques appearing in the literature. Now, we
are happy to report, everything has changed.
Berger Instruments acquired the model G1205A SFC instrument from Hewlett-Packard in late 1995 and introduced a new
instrument in 1996. Berger both improved and simplified this
instrument over its predecessor, retaining its best features, and
lowering the price by about one-third. Jasco, who has marketed
SFC equipment in Asia and other parts of the world for many
years, is now actively marketing their instrument in the United
States. Gilson continues to improve their modular instrument with
new autosampler and fraction collection capabilities and significant
improvements in control software.
One extremely important point that potential customers must
understand is that these packed-column instruments, although
called the quite limiting name supercritical fluid chromatograph,
are capable of performing much more. These instruments, with
no (or perhaps only trivial) modifications, can perform nearly all
of the unified chromatography techniques including conventional
LC. If equipped with subambient temperature control and used
with sufficiently low-viscosity mobile phases, these instruments
can perform LC or SubFC (the name distinction is hardly
significant) at temperatures as low as -50 C. These instruments
can perform high-temperature LC (or SubFC, enhanced-fluidity
LC, or SFC, depending on mobile phase and parameter choices)
at temperatures far exceeding that possible with conventional LC
instrumentation. These capabilities offer many new possibilities
in speed and chromatographic selectivity. Customers do not have
to risk the entire cost of the instrument when purchasing an SFC,
but only the small additional expense over a comparable LC. Even
if an instrument is purchased to test just one unconventional
chromatographic possibility, in the worst possible outcome the
customer will be left with an extremely powerful instrument
completely encompassing and surpassing conventional LC.
In 1997, Dionex withdrew from the SFC market entirely,
leaving no commercial source for open-tubular SFC (otSFC)
instruments. (The U.S. patent on otSFC still has several years
remaining.) However, a new supplier, Sensar/Larson-Davis, is
offering an SFC instrument, under license, that will support both
open-tubular and packed microcolumns.
Theory, Fundamentals, and Comparisons. Understanding
continues to develop in the thermodynamics of SFC retention
processes and the effects of parameters on retention and selectivity. Roth examined modifier effects on retention and separated
density effects from intermolecular forces (21). He also combined
classical and molecular thermodynamic approaches to solute
distribution in a chromatographic system to predict retention (22)
and showed the importance of considering stationary-phase
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Analytical Chemistry, Vol. 70, No. 12, June 15, 1998
tivity shifts in SFC with polymeric stationary phases (23). Kautz

et al. measured retention factors for several solutes under a variety
of conditions and discussed effects of density and selectivity (24).
Pyo et al. applied linear solvation energy relations to SFC using
methanol-modified CO2 mobile phase to explain solute retention
(25). Shen et al. extended the earlier work of Martire and Boehm
to explain retention in SFC (26). Mitra et al. reported a simple
empirical method for predicting retention (27). Zhao extended
the rate theory by using fugacities instead of solute concentrations
(28). This approach avoids the restriction of modeling only at
infinite dilution. Wang et al. (29), Yaku et al. (30), Lou et al. (31),
and Funada and Hirata (32) also investigated retention in SFC.
The term modifier is used to denote a solvent added to the
primary mobile-phase fluid (usually CO2 in SFC) to aid in
dissolving and eluting solutes. An additive is a third mobile-phase
component, usually dissolved in small concentration in the
modifier and used to influence specific solute-stationary-phase
interactions. For example, triethylamine may be added at 0.5%
to a methanol modifier to reduce retention and improve peak
shape of basic solutes. Cantrell et al. reported the characterization
of modifiers using monofunctional solutes and a cyano stationary
phase (33). They also used solvatochromic techniques in their
characterization and concluded that modifiers can be chosen either
to enhance or to suppress the effects of a particular type of
intermolecular interaction. Blackwell et al. studied the effect of
mobile-phase additives on retention for various compounds using
both sub- and supercritical conditions (34). Blackwell and
Stringham examined temperature effects on selectivity and found
the hydrogen-bonding character of the analytes to be particularly
important (35). Williams et al. examined the retention behavior
of PAHs using monomeric and polymeric C18 bonded phases and
provided guidelines for optimization of shape selectivity in SFC
(36). Cantrell and Blackwell compared strength, selectivity,
efficiency, and temperature effects of the mobile phases 1,1,1,2tetrafluoroethane (HFC-134a) and CO2 (37).
One of the basic fundamentals of SFC is that when selectivity
is comparable to LC for a particular application, SFC analyses are
considerably faster. This arises because faster mobile-phase
diffusion coefficients translate directly into faster optimum velocities. Even more speed is possible in programmed elution because
reequilibration of columns under SFC conditions is usually much
faster than with LC. Graham et al. compared SFC with LC using
four different packed columns for the separation of butylcalix[n]arenes and improved speed of analysis by the factor 3.5 using
SFC (38).
Of course, selectivity is seldom identical when the conditions
are so different, even when LC and SFC are compared using the
same solutes and column. SFC selectivity may be better or worse
than LC upon initial trial, perhaps frequently being worse at first
if the LC conditions were optimized before SFC was even
attempted. Workers should not be discouraged but should instead
take advantage of the numerous mechanisms to adjust selectivity
in SFC and related techniques. In comparing optimized SFC with
optimized LC, odds for achieving useful selectivity may actually
favor SFC since there are more adjustable (and optimizable)
parameters, particularly the temperature and its much larger range
in SFC. It is also essential to remember that the best selectivity
for a specific application in LC and in SFC may require different
stationary phases. Direct comparisons of LC and SFC should be

done carefully for these reasons and not much significance applied
to results when many parameters remain fixed. Several SFC/LC
comparisons appeared during this reporting period (39-43).
Chiral separations are very frequently superior in SFC as
compared to LC. Williams et al. report SubFC and SFC advantages of simple eluents, rapid optimization, and better resolution
compared with LC using a modified -cyclodextrin stationary
phase (43).
Lower viscosities of supercritical and subcritical fluids, compared to familiar liquids, lead to lower pressure drops and the
possibility of using longer columns than in LC to achieve higher
plate counts. However, the possibility of complications arising
because of the compressibility of the mobile phase and its
expected loss of strength as it decompresses along the column
has been debated for several years. The debate continues. Lou
et al. examined the effect of pressure drop on pcSFC and
concluded that long columns with large (apparent) plate numbers
do not give better separations (44). Li et al. reached similar
conclusions using packed microcolumns (45). Bouigeon et al.
found significant apparent efficiency loss that increased in long
packed columns with increasing pressure drop (46). They
suggested superimposing a temperature gradient to somewhat
counteract the longitudinal density gradient caused by the pressure drop. Poe et al. showed evidence of a longitudinal temperature drop in columns having a longitudinal pressure drop and
improved apparent efficiency by insulating the columns (47, 48).
In the arguments on this subject in recent years, many of the
participants have not realized that column efficiency cannot be
measured directly in columns where a gradient exists. Even if
no conditions are programmed (i.e., there are no temporal
gradients), gradients exist spatially in SFC columns having
pressure drop. These gradients invalidate direct calculation of
actual plate number by simply observing the retention time and
peak width at the column outlet. (These calculations are still
possible in GC even with a significant pressure drop since
retention factors are essentially independent of pressure. However, in SFC and any technique with a compressible, solvating
mobile phase, the spatial pressure gradient creates a corresponding spatial gradient in mobile-phase strength and in retention
factor for every solute. The leading edge of a peak is always in
weaker mobile phase than the trailing edge.) Apparent efficiency
may have no more significance here than in temperatureprogrammed GC or gradient-elution LC, particularly if the pressure
drops are large, and must be used with extreme caution even if
there is no temporal programming involved in the measurements.
Enhanced-fluidity liquid chromatography continues to be
advanced by Olesik and co-workers (49-58). Miller and Hawthorne (4) and Smith and Burgess (5) used neat liquid water,
pressurized and heated well above its normal boiling point, as
mobile phase, finding it to easily transport alcohols, hydroxylbenzenes, amino acids, phenols, parabens, barbiturates, and other
materials. Although appearing to the casual observer to be
distinctly different from SFC, work in these areas is simply
executed in a different part of the continuum of mobile-phase
properties.
In addition, these techniques require SFC instrumentation: In
the hot-water examples, the column outlet pressure is elevated
high enough to prevent boiling. In enhanced-fluidity LC, CO2 is

typically pumped into the mobile phase, and the column outlet
pressure is significantly elevated and regulated above ambient to
keep the mobile phase from separating into coexisting liquid and
vapor phases. If a mobile phase were used in which there is a
miscibility gap between the mobile phase and pure CO2, it could
be argued that the technique is technically different from SFC or
SubFC. However, recent work has used mixtures that have no
such gap. We continue to believe that the subdivision of
chromatography nomenclature over such technicalities causes
confusion and actually slows acceptance of the emerging techniques. Regardless, the examples cited of both hot-water chromatography and enhanced-fluidity liquid chromatography, particularly polymer characterization by size exclusion (53, 54) and
separation at the critical condition (52), have been impressive.
Stationary Phases and Columns. Nearly all the new work
on stationary phases has been for packed columns. Petersson
and Markides evaluated several adsorbents (59), and Shen and
Lee adapted polyhydromethylsiloxane deactivation to silica microparticles (60). Zhang et al. reported an in situ deactivation of
packings and characterized them using NMR (61). Li et al.
explored the use of packed-capillary columns with low column
diameter-to-particle diameter ratios (62).
Shen et al. accomplished an incredible amount of work in
developing and evaluating new stationary-phase packings. These
include SE-54-coated silica (63), cyanobiphenyl-substituted polymethylsiloxane-coated silica (64), several diol-bonded silica phases
(65), end-functionalized poly(ethylene oxide)-coated silica (66),
polyethylenimine-coated bare silica and diol-modified silica (67),
and a silver-complexed dicyanobiphenylsiloxane coated onto
deactivated silica particles (68). Shen et al. also examined the
use of nonporous silica instead of the traditional porous particles
as stationary-phase supports (69,70). Li et al. evaluated a
fluorinated silica packing (71). Shen et al. coated silica particles
with a cyclodextrin-modified polysiloxane and evaluated columns
with a variety of chiral solutes (72).
Donnecke et al. modified a cyclodextrin, incorporated it into a
polysiloxane, and used it to prepare open-tubular columns for SFC
and LC (73). Medvedovici et al. systematically evaluated several
chiral stationary phases for the pcSFC separation of 44 racemic
solutes (74). There are several significant advantages in doing
chiral chromatography at temperatures as low as -50 C. Wolf
and Pirkle evaluated two brush-type chiral stationary phases at
subambient temperatures, achieved greater enantioselectivity and
resolution than at ambient temperature, and also slowed interconversion rates for the separated enantiomers (75). Abornev et
al. performed otSFC using a multichannel column (76).
SFC Instrumentation, Techniques, and Performance.
Injection continues to be an area in need of new research.
Although accuracy and precision are excellent with several direct
injection techniques, maximum sample volumes with simple direct
injection techniques are smaller in pcSFC than in LC and are also
smaller in otSFC than in GC. Berg et al. used both direct injection
and on-line SFE/SFC to introduce edible fat samples into an otSFC
column (77). Ibanez et al. described on-line SFE/SFC for sample
introduction into micropacked columns (56). Arnold and Kleiboehmer used a solid-phase sample loop injector to introduce up
to 100 L into packed columns and 5 L into a capillary column
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(78). Carlsson et al. developed a peak-compression injection for

pcSFC which works with specific combinations of mobile phase
and sample solvent (79).
Leichter et al. gave convincing evidence that helium added to
CO2 cylinders to improve transfer into pumps weakens the mobile
phase and increases solute retention and that the magnitude of
this effect changes as the cylinder is depleted (80). This occurred
for both neat and modified CO2 mobile phases. Robson et al. (81)
and Ibanez et al. (82) reported methods for introducing modifier
into CO2 at flow rates sufficiently low for packed-capillary columns.
Pyo et al. developed an amperometric microsensor to monitor the
concentration of water modifier in supercritical CO2 (83). Heaton
et al. described how to use the mobile-phase modifier as a trapping
fluid for preparative SFC (84). Hanson used SFC in a micropreparative fashion to purify and collect milligram quantities of
steroids (85). Takeuchi and Saito described a two-dimensional
SFC separation in which a polarity- or hydrogen-bonding-based
separation was conducted on a column, fractions were collected,
and each one was further separated by a molecular-weightselective separation (86). Hatano and Hanai also reported twodimensional SFC (87).
SFC Detectors. With the research and application emphasis
shifting strongly to packed columns in the last couple of years, it
is not surprising to see a shift in detector development emphasis
from GC-like detectors to LC-like detectors. This is caused by
the higher flow rate requirements of pcSFC and the frequent use
of modifiers with packed columns.
Wallenborg et al. used oxidative and reductive amperometric
detection with CO2 mobile phase modified with water, acetonitrile,
or methanol and with pressure programming (88-90). They
achieved low-picogram detection limits in favorable cases. No
salts were required in the mobile phase. Dressman et al.
voltammetrically detected phenols and PAHs in neat and methanolmodified CO2, achieving low-nanogram detection limits and two
decades of linearity (91).
Albert and Braumann interfaced SFC with proton NMR (92).
Later, Braumann et al. applied SFC/NMR to the separation and
detection of five cis/trans isomers of vitamin A acetate (93). They
noted that no solvent signal suppression is necessary (with CO2
mobile phase) and that, unlike HPLC/NMR, the entire spectral
range is available for detecting solutes. Albert then reviewed SFC
and SFE coupled with NMR (94).
Evaporative light-scattering detectors (ELSDs) work very well
with SFC instruments because of the ease of evaporating mobile
phase. Although our search only found three papers abstracted
during the review period, we are aware of significant additional
work presented at recent meetings and now in press and expect
the ELSD to become an important detector in pcSFC. Berry et
al. used UV and ELSD detection in series to detect mixtures of
chromophoric and nonchromophoric solutes (95). Strode and
Taylor investigated the effect of makeup gas flow and modifier
parameters and achieved detection limits of 10 ng of steroids (96).
Salvador et al. separated monosaccharides and polyols by SubFC
using an SFC instrument (97). Their mobile phase was CO2
modified with methanol and sometimes containing smaller amounts
of water and triethylamine.
Shi et al. coupled a chemiluminescent nitrogen detector with
otSFC detecting as little as 60 pg of N (98, 99). Shi et al. later
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successfully coupled this detector with pcSFC using methanolmodified CO2 mobile phase with both pressure and modifier
gradients (100). Fujinari showed how this instrumentation is
useful for analyzing spices (101). Combs et al. optimized
conditions to achieve 25 pg of N detection limit for sulfamethazine
(102). Chemiluminescence detection is also possible for sulfur.
Shi et al. tested pcSFC with sulfur chemiluminescence detection
realizing a detection limit of 3 pg of S (103).
Smith et al. separated, detected, and identified Irganox 1076
by SFC-IR using a solvent elimination interface originally
designed for LC/IR (104). They reported obtaining high-quality
spectra from 700 to 4000 cm-1 with no interference from the
methanol modifier. Norton et al. showed that occasional incorrect
identifications may result when KBr disk library spectra are used
for searches of SFC/IR spectra when the solutes are collected on
crystalline substrates (105). They recommend using amorphous
substrates to minimize these problems. Yang et al. rapidly
distinguished compounds extracted from paper using SFC/FTIR in conjunction with principal component analysis (106). Yang
and Griffiths used otSFC/IR to separate and identify several
sulfanilamides (107).
In other assorted detector advances, Hirata et al. used a UV
detector as a refractive index detector in SFC with neat CO2 (108).
Although careful control of temperature and especially pressure
is necessary in the detector cell, the low refractive index of CO2
yielded a detection limit of 30 ng of solute in the detection cell,
but a 1:1000 split was required in the interface. Montes-Bayon et
al. looked at the effect of CO2 and Xe on microwave-induced
plasmas (109). Tarver performed ion-mobility detection in SFC
(110). Strode and Taylor performed electron-capture detection
in pcSFC with modified CO2 achieving picogram detection limits
with up to 5% modifier (111). Wilkes examined interfacing SFC
columns to GC detectors (112).
SFC/MS. A number of reviews either included or focused
on the coupling of SFC with mass spectrometry (MS), arguably
the single most informative detector available (59, 113-115).
Pinkston and Chester described the chromatographic and mass
spectrometric choices the analyst must make in coupling SFC and
MS (114). Many choices, such as the method of injection, the
type of flow restrictor, the type of mass spectrometer, the
ionization method, and the type of vacuum system, can make the
difference between failure and success. The authors describe
successful combinations and important applications. Combs et
al. argued that pcSFC/MS should not be considered a technique
of last resort but should be considered before LC/MS for rapid,
rugged determinations (115). All the reviews pointed to the
promise of atmospheric pressure ionization (API) methods. In
fact, the reviewers predictions of a move toward API methods
are fulfilled when considering SFC/MS publications that appeared
during this review period (116-122). Broadbent et al. used a
versatile atmospheric pressure chemical ionization (APCI) interface and used SFC/APCI-MS to study the photoproducts of a
commercial sunscreen (118). Sjoeberg and Markides described
a similar interface, which allowed rapid conversion between
electrospray and APCI (122). Lazar et al. designed, constructed,
and characterized an APCI source for SFC coupled to time-offlight MS (117). Pinkston and Baker modified a pneumatically
assisted electrospray (ion spray) interface for otSFC/MS (116).
The interface incorporated a sheath-flow liquid, flowing concentrically to the SFC flow restrictor, which allowed both the chromatograph and the mass spectrometer to be operated independently under optimum conditions.
Other publications described the coupling of SFC with sector
mass spectrometers using the direct fluid introduction approach
(123, 124). Both Mertens et al. (123) and Brede and Lundanes
(124) emphasized the suitability of SFC/MS for the analysis of
thermally labile materials. The flow restrictor temperature was
shown to have a pivotal impact on the successful analysis of
thermally labile diflubenzuron (124). The molecular ion produced
by electron attachment negative ionization was the base peak at
a restrictor temperature of 160 C, while it was absent at a
restrictor temperature of 190 C. Ramsey and Raynor studied the
limits of detection achievable for pyrene using otSFC coupled to
a benchtop quadrupole mass spectrometer in full-scan and
selected-ion-monitoring (SIM) modes and using electron ionization
(EI) and chemical ionization (CI) (125). They found a detection
limit of 1 pg using ammonia CI and SIM. Other publications
describing applications of SFC/MS are reviewed in the Applications section.
SFC Applications. Berger recently provided a wide-ranging
review of the separation of polar solutes using pcSFC (126).
(a) Fats, Oils, and Other Food-Related Samples. The
application of various SFC techniques to the analysis of food
components was covered in a number of excellent reviews which
appeared in two monographs (127-131). These reviews deal
primarily with oils and oil components. In addition, Chester (129)
and Borch-Jensen and Mollerup (130) discuss instrumentation
and choice of technique. Flament et al. make a strong argument
for the wider adoption of semipreparative SFC as a general tool
for the separation and isolation of the nonpolar components of
flavors and foods (132). Reactions with, and residues from, the
mobile phase are minimized with CO2 as mobile phase. Lafosse
et al. reviewed the use of SFC for the characterization of
carbohydrates (133). They concluded that open-tubular and
pcSFC provide complementary selectivities and information,
though polar, underivatized monosaccharides and polyols can be
efficiently separated by pcSFC using methanol- or methanol/watermodified CO2 (97). The ELSD is often used as a detector for
these separations. Salvador et al. used a flow rate of 5 mL/min
and a column temperature of 60 C to fully separate eight
monosaccharides and polyols in less than 10 min (97).
SFC is clearly well suited to the characterization of seed and
crop oils (134-138). Borch-Jensen et al. used a variety of
chromatographic techniques to study seed oils and found that SFC
was most versatile for studying both the free fatty acids and the
intact oils (134). Choo et al. used SFC on a combination of a C18
and a silica column to perform a semipreparative separation of
palm oil components (136). Subra and Vega studied the use of
SFC to detoxify bergamot peel oil (139). They were able to
selectively retain the psoralen toxins at low pressure and high
temperature.
The SFC characterization of other types of oils and oil
substitutes was also described during this review period. BorchJensen et al. used otSFC to characterize a variety of fish, shark,
and seal oils (140) and six shark liver oils (141). The authors
used a combination of thin-layer chromatography fragmentation
and SFC to fully characterize the shark liver oils. Cow colostrum
triglycerides, and their changes during parturition, were studied
by Laakso et al. using SFC and MS (142). Artz et al. studied the
thermal oxidation and polymerization of heated oil substitutes,
linoleic and oleic acid-esterified propoxylated glycerol using otSFC
(143).
Other publications focused on the characterization of various
oil components. Galuba and Gogolewski (144) used SFC to
characterize tocopherols in oils. Medvedovici et al. used pcSFC
for the separation of the sterol fraction from vegetable oils,
followed by off-line GC/MS of the underivatized sterols (146).
The SFC fractionation required less than 8 min, with the injection
and collection steps being fully automated. Huber et al. compared
the performance of SFC and GC for the determination of
cholesterol in milk fat (147). They found the accuracy of SFC to
be superior to that of GC. Shen et al. used packed capillarycolumn SFC to separate a number of fat-soluble vitamins (148).
They studied the shape selectivity of various liquid crystal
stationary phases coated on deactivated silica particles and found
the more highly ordered liquid crystals provided greater shape
selectivity.
SFC played an important role in the extraction and isolation
of fatty acids (149, 150). Ikushima et al. combined on-line SFC/
FT-IR with SFE to monitor the extraction of higher fatty acid esters
(149). Kadota et al. used silver-loaded spherical clay as a
stationary phase to perform pilot-scale separations of fatty acid
ethyl esters (150). They recovered docosahexaenoic acid ethyl
ester with a purity of greater than 99% and an efficiency of 65%.
On an analytical scale, Borch-Jensen and Mollerup compared three
chromatographic techniques for the determination of vernolic acid
(12,13-epoxy-9-cis-octadecenioc acid) in the oil of Euphorbia
lagascae (151). They investigated GC of the methyl ester
derivatives, SFC of those same derivatives, and SFC of the raw
oil. SFC of the fatty acid derivatives was the most accurate
method. De Swaef et al. investigated two alternatives for the
otSFC of fatty acids extracted from Sabal serrulata (152). They
found that both use of unmodified CO2 with ethyl ester derivatives
and separation of the free fatty acids with water-saturated CO2
provided dramatically improved peak resolution. Manninen and
Laakso used APCI-MS fragmentation patterns combined with online otSFC retention behavior to study various linolenic acid
isomers in berry oils (121).
(b) Natural Products. Most natural product-related work
used pcSFC and investigated a variety of columns and modifiers
to obtain an optimized separation (153-158). Compound classes
investigated included resin acids (153), triterpenoid compounds
of importance in the perfume industry (154), glycolipids, phospholipids, and carbohydrates (155), ginkgo terpene trilactones
(156), polymethoxylated flavones from citrus oils (157), and
sesquiterpene lactones (158). Most researchers used UV detection, but Thompson et al. (156) and Herbreteau et al. (155) used
the ELSD. They found detection limits in the 10-20-ng range.
Dugo et al. used molecular modeling to calculate dipoles and help
explain the SFC retention of polymethoxylated flavones (157).
Substituent position, neighboring dipoles, and steric hindrance
were all postulated to play a role in retention. Blum et al. used
otSFC/MS to characterize thyme extracts (159). They used the
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retention gap method of direct injection and a direct-fluid MS

interface.
(c) Agrochemicals and Environmental Samples. Berger
published two works describing the on-line extraction from large
aqueous samples and the pcSFC chromatography of sulfonyl
herbicides (160) and of nearly 100 thermally labile pesticides
(161). Rapid separations were performed on a 25-cm column,
while a 1.6-m-long packed column provided high-resolution
separations. Multiple detection (UV, electron capture, and nitrogen-phosphorus) provided in-depth characterization of the samples.
The volumes of on-line-extracted samples ranged up to 100 mL,
while detection limits ranged as low as 10 ppt. Bicchi et al. used
off-line solid-phase extraction (SPE) followed by pcSFC/UV to
determine diflubenzuron, teflubenzuron, and triflumuron in fruit
baby foods (162). Both Bernal et al. (163) and Yarita et al. (164)
used on-line extraction coupled to pcSFC to improve the detection
limits for determining pesticides and herbicides, respectively.
Bernal et al. evaluated 10 silica packed columns coupled in series
for high-resolution separations of 184 pesticides (163). They used
on-line SPE to improve detection limits to approximately 10 ppt.
Rather than on-line SPE, Yarita et al. used on-line SFE to detect
thiocarbamate herbicides (164).
Pocurull et al. (165) and Ramsey et al. (119) used pcSFC to
rapidly determine phenols and nitrophenols in water. Pocurull
et al. tested a variety of on-line SPE sorbents to improve detection
limits (165). Rather than using a sorbent, Ramsey et al. used
on-line, direct SFE of aqueous samples, and pcSFC followed by
atmospheric pressure chemical ionization MS detection (119).
Detection limits for the latter work were in the tens of ppb.
Packed-column SFC of polycyclic aromatic hydrocarbons (PAHs)
and hydroxy-PAHs was the subject of a number of publications
(120, 166-168). Lourdes Cardeal et al. used an injectionsolvent-elimination system which permitted multiple injections
with sample accumulation before the separation was performed
with a cyclohexane-modified gradient and UV detection (167). A
similar approach, but using on-line preconcentration on SPE disks,
was employed by Bernal et al. (168). Detection limits in the lownanogram range were obtained for hydroxy-PAHs by Moyano et
al. using pcSFC/APCI-MS (120). Burford et al. demonstrated the
utility of SFC with packed-capillary columns for environmental
samples (169).
(d) Fossil Fuels and Synthetic Lubricants. Considerable
effort has been devoted to developing multidimensional chromatographic instrumentation involving SFC for the characterization of complex fossil fuel mixtures. For example, Pal et al.
described a system for separating gas oil samples in which the
effluent from a 4.6-mm-i.d. packed column was directed to a tee
(170). One arm of the tee was connected to a UV detector, while
the other was connected to a switching valve and a nonpolar, opentubular column. The packed column provided group separations,
monitored by the UV detector, while the open-tubular system
provided high-resolution separations. A variety of sophisticated,
multidimensional methods for characterizing oil industry samples,
including some involving SFC, were reviewed by Schoenmakers
et al. (171). Nomura et al. used simultaneous, on-line fluorescence, UV absorption, and FID to more fully characterize fractions
of various fuel oils separated by pcSFC (172). Rather than
multiple detectors or multidimensional separations, Squicciarini
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used higher chromatographic efficiency, by means of four columns

coupled in series, to more fully characterize gasoline and JP-4 jet
fuel (173).
Due to the complexity of natural oils, much work in this area
focused on fractionation. For example, Xu et al. used pcSFC with
pentane mobile phase to fractionate bitumen pitch (174). The
fractionation was followed by elemental analysis. The benefits of
enhanced-fluidity, reversed-phase HPLC were demonstrated by
Lee et al. in a separation of a coal tar, among other mixtures (49).
CO2 was added to the methanol/water mobile phase to decrease
viscosity, increase diffusion coefficients, and increase chromatographic efficiency without a significant drop in solvent strength.
Kelemidou and Severin compared GC and SFC for simulated
distillation of high-boiling petroleum fractions (175). SFC removes
the upper molecular weight limit imposed by GC. For somewhat
less complicated mixtures, SFC provides resolution of individual
components. For example, Kuehn et al. compared size-exclusion
chromatography (SEC), SFC, and matrix-assisted laser desorption
mass spectrometry for the characterization of technical waxes
(176). While SEC provides a higher upper molecular weight limit
and a wider molecular weight range, SFC provides far superior
resolution of individual species in homologous series. In other
work dealing with synthetic mixtures, Didziulis and Bauer found
that SFC was useful in characterizing phosphate ester lubricants
intended for spacecraft applications (177). Phosphoric acid (0.5%)
was an unusual but effective additive to the ethanol-in-CO2 mobile
phase in the pcSFC of flavonol isomers studied by Liu et al. (178).
(e) Synthetic Polymers and Oligomers. SFC is well-known
for its ability to characterize low-molecular-weight polymers and
oligomers. It is arguably the best chromatographic method for
the separation, for example, of nonionic surfactants, as reviewed
by Cserhati and Forgacs (179). Just and Much provided a
comprehensive analysis of the use of supercritical mobile phases
in three separation modes: adsorption chromatography for the
separation of oligomers, size-exclusion chromatography for the
determination of molecular weight distributions, and adsorption
chromatography at critical conditions (the point where sizeexclusion effects are balanced by adsorption effects) for the
determination of functionality type (180). The authors provided
examples of these modes with separations of polystyrenes. Just
also reviewed the use of SFC for the analysis of a variety of
polymers and oligomers and compared the results to separations
obtained with other chromatographic techniques (181). Polysiloxanes were investigated with SFC, HPLC, and matrix-assisted
laser desorption MS by Just and Krueger (182). SFC and MALDIMS provide complementary information, while HPLC was most
useful for fractionating cyclic from linear oligomers. The authors
found that MALDI-MS provided higher resolution at high molar
mass (8000 Da) than did SFC. They warn that interpretation
of molar mass distribution by MALDI-MS, however, has to be
done with caution. Yuan et al. (53), Yaun and Olesik (54), and
Souvignet and Olesik (52) explored the advantages of enhancedfluidity size-exclusion chromatography for the analysis of polymers. They used polystyrene and poly(styrene-methyl acrylate)
as probe analytes. Mixtures of up to 40 mol % CO2 with
tetrahydrofuran resulted in a significant drop in mobile-phase
viscosity, without a decrease in solvent strength. Adsorption
effects began to play a role at CO2 concentrations above 50 mol
% (53). Raising the temperature had much the same effect as

adding CO2 to the mobile phase (54). The highest chromatographic efficiencies were obtained when both high temperatures
(up to 100 C) and high CO2 concentration (up to 30 mol %) were
employed. Since the enhanced-fluidity mobile phase is compressible, Olesiks group found that pressure could be used to achieve
the critical condition (52). This is much simpler than mobilephase variation, as in conventional critical chromatography.
Trathnigg and Maier used a variety of chromatographic methods,
including SFC, for the characterization of polyethers (183).
The extraction of polymer additives from polymers using SFE
is well-known, as described later in this review. It is therefore
not surprising that SFC might be used to also analyze these
important components. Jordan et al. described the use of on-line
SFE/SFC/FT-IR to extract, separate, and identify the extractables
in nylon and polystyrene (184). In a different approach toward
the use of SFC in polymer chemistry, Hatada et al. used SFC to
fractionate synthetic uniform polymers from a homologous
mixture (185, 186). (A uniform polymer was defined as a
polymer composed of molecules with the same structure and a
very narrow molecular weight range.) Such uniform polymers
can be used to build highly regular macromonomers for the
synthesis of even higher molecular weight polymers with unique
properties.
(f) Organometallic Compounds. A number of publications
were devoted to the SFC analysis of organometallic compounds
during this review period. Most employed pcSFC with modified
CO2 mobile phase (187-189). But Wu et al. published an unusual
account of the use of organophosphorus (tributylphosphine oxide
or trioctylphosphine oxide) adduct formation to enable elution of
lanthanide -diketonates using unmodified CO2 and otSFC/FID
(190). The lanthanide -diketonates decompose in the chromatographic system when the adducts are not formed. Kumar et al.
also used otSFC for organometallic analysis (191). They compared the performance of inductively coupled-plasma (ICP) mass
spectrometric detection to FID for arsenic, antimony, and mercury
compounds. Detection limits were 2-3 orders of magnitude lower
with ICP-MS than with FID. The generation of liquid waste is
undesirable in uranium processing and analysis. This was largely
avoided during the quantitative determination of uranium using
pcSFC of organometallic uranium complexes by Martin-Daguet
et al. (187). Glennon et al. (188) and McSweeney et al. (189)
used pcSFC/UV to study Fe(III) complexing agents. They found
evidence of ligand contamination by Fe(III) from the SFC system
while studying hydroxamic acids (189). They also conducted an
extensive investigation of the pcSFC behavior of various modified
calixarenes, molecular basket complexing agents (188).
(g) (Achiral) Pharmaceutical Agents and Biologically
Important Mixtures. A comprehensive review of publications
involving the application of SFC to drug analysis was published
in 1996 (192). Most SFC used in drug analysis is pcSFC. This
is mostly due to higher speed of analysis in pcSFC than in otSFC.
This was the conclusion reached by Kohler et al. when they
compared otSFC/FID to pcSFC with evaporative light scattering
detection for the determination of an antimalarial agent, artemisinin, and related compounds in plant extracts (193). Analysis time
in pcSFC/ELSD was approximately one-third that in otSFC/FID.
Other drugs determined by pcSFC include antifungal agents
(194), salbutamol sulfate and related compounds (195), paclitaxel

and related taxanes (196), and benzodiazepines (197). Most of
these works included investigations of various columns, mobilephase modifiers and additives, and chromatographic conditions,
to provide a rapid, high-resolution separation. Combs et al. also
explored various columns and conditions for the separation of
eight regulated sulfonamides (198). They found that two coupled
25-cm columns, one a silica and one an aminopropyl column,
provided an acceptable separation in less than 20 min. Subtle
changes in temperature greatly affected retention of some of the
analytes. Karlsson et al. used experimental design with four
factors (modifier concentration, flow rate, column temperature,
pressure) to develop a fast pcSFC separation for the determination
of a dihydropyridine drug (199). They found the concentration
of the polar mobile-phase component and the flow rate to be the
most important variables. In contrast to the above works, otSFC
(rather than pcSFC) with MS detection was used for the determination of the macrolide antibiotic mydecamycin A1 by Ramsey
et al. (200). Mass spectrometric detection was also used for the
determination of drugs of abuse. Backstrom et al. used pcSFC/
APCI-MS for the rapid determination of Cannabis-related compounds (201). The analysis time using this method was shorter
than either GC/MS or LC/MS, and no derivatization was required.
Packed-column SFC was also used for the rapid analysis of
biologically important mixtures such as bile acids (202) and
steroids (203). Villette et al. used pcSFC/ELSD for the determination of free bile acids (202). A comparison of capillary
electrophoresis and pcSFC for the determination of urinary
metabolites was conducted by Simon and Nicot (203). A mixture
of ethanol, water, and methanesulfonic acid (97.5:2.4:0.1) was used
as the CO2 modifier in pcSFC. They found the two techniques
provided complementary information. Baiocchi et al. used otSFC
for the analysis of steroid mixtures (204). They found that the
electron capture detector provided better signal-to-noise ratios than
the FID.
The mild elution conditions available in SFC, and the generally
nonreactive nature of the CO2 mobile phase, make pcSFC
especially promising for the preparative or semipreparative separation of labile materials. In the preparative chromatography of
pharmaceutical agents or their precursors, where residual solvent
or solvent impurities can be an issue, CO2 can be an even more
attractive alternative as a mobile phase. Bernet et al. illustrated
this point as they studied the thermolysis of dihydrothiadiazoles
(205). They isolated pure thermolysis products using semipreparatory pcSFC, while preparative HPLC resulted in partial or
complete decomposition.
(h) Chiral SFC. Rapid progress in the development of chiral
SFC continued during this review period. Many reports of
superior separations and easier method development have appeared in print and in oral presentations. These advances have
been the subject of a number of reviews (206-209). In one of
these, Majors not only reviews chiral SFC but places its utility in
perspective with chiral GC, CE, and HPLC (208). Chiral SFC is
most useful for high-molecular-weight and/or thermally labile
compounds which cannot be eluted or resolved in GC and which
are separated too slowly in HPLC. Stringham and Blackwell have
developed a theoretical model of chiral SFC and have explored
the theory of entropically driven chiral separations in SFC (210Analytical Chemistry, Vol. 70, No. 12, June 15, 1998
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212). Resolution generally decreases as column temperature

increases. As the temperature is raised to increasingly higher
levels, the enantiomers coelute and then, theoretically, are
resolved with reversed elution order. These latter separations
are said to be entropically driven. Stringham and Blackwell found
that crossing the critical temperature has a variety of effects not
predicted by this theory (210). Also, they found that the ability
to achieve entropically driven separations in SFC is limited by
high isoelution temperatures (which bodes well for chiral SFC
separations at lower temperatures) (212). Use of hexane rather
than CO2 provided successful entropically driven separations. Wolf
et al. also investigated fundamental aspects of chiral SFC (213).
They used subcritical fluid chromatography and computer simulation to determine the enantiomerization barriers of arylnaphthalene lignans bound to chiral stationary phases.
Most publications in the chiral SFC area during this review
period discussed either new chiral stationary phases (CSPs) or
the separation of enantiomeric pharmaceutical agents. Many of
the CSPs incorporated modified cyclodextrins (214-216). Most,
as in the case of Williams et al. (214), also report separations
that were only possible, or that were of substantially higher quality,
in SFC than in HPLC. The stationary phase described by
Grosenick and Schurig consisted of a modified cyclodextrin
incorporated into a polysiloxane, named Chirasil-DEX (216). This
polysiloxane-based stationary phase was tested as a coating in
open-tubular columns and used in four modes: GC, otSFC, otLC,
and electrochromatography (215, 216). Pirkle-type chiral selectors were also incorporated into polysiloxanes and coated on silica
to provide CSPs for packed columns with wide applicabilities (217,
218). At least one of these has been commercialized as the
PolyWhelk-O CSP (218). Pirkle et al. published an extensive
compilation of enantiomeric separations using this phase covering
a wide variety of compound types (218). Garcia et al. described
a derivatized cellulose-based CSP packing designed for rapid
separations using microbore SFC (219). High-resolution microbore or microcapillary SFC separations were also performed
using a novel CSP by DAcquarica et al. (220). These authors
also modeled the separation and used this model to guide their
selection of chromatographic conditions.
Many publications used one or more pharmaceutical agents
as probes to compare chiral pcSFC to chiral HPLC. The results
described by Williams et al. are typical (221): column equilibration
and chromatographic condition optimization were accomplished
more rapidly in pcSFC than in HPLC. Improved resolution was
often observed in chiral pcSFC, and analysis times in pcSFC were
often, though not always, shorter. The great majority of the
applications of chiral pcSFC to pharmaceutical agents employed
cellulose-based chiral stationary phases. Most of the authors
found that the column temperature and modifier concentration
had the greatest effect on resolution. Some of the stationary
phases and compound classes investigated included camazepam
(a hypnotic/anxiolytic agent) and its metabolites on Chiralcel
OD-H (222), -blockers on Chiralcel OD and Chiralpak AD (223),
a cardiac antiarrhythmia precursor on Chiralcel OB (224),
indinavir (a protease inhibitor) on Chiralpak AD (225), Profen
nonsteroidal antiinflammatory agents, barbiturate derivatives, and
benzodiazepines on Chiralcel OJ (226), phenylpropanols on
Chiralcel OD and Chiralcel OB (227), D,L- and meso-N,N,-bis308R
(carbobenzyloxy)-2,6-diaminopimelic acid on Chiralpak AD (228),

and diltiazem HCl (a Ca-channel blocker) on Chiralcel OD (229).
As discussed in the latter separation, one advantage of pcSFC over
HPLC is speed (222, 229). Yaku et al. separated four isomers
with baseline resolution in less than 8 min. (229). BargmannLeyder compared the chiral pcSFC and HPLC of -blockers (223).
They found that the selectivity for a pair of enantiomers can vary
widely between these techniques, even when the same cellulosebased CSPs are used. This is especially true when the isomers
carry polar, hydrogen-bonding functional groups. The authors
recommend investigating both chiral pcSFC and HPLC for each
pair of analytes, to find which is more stereoselective. This can
be accomplished using modern, commercial pcSFC instrumentation. The mobile-phase mixture used most often in the separations
cited above was methanol-modified CO2, sometimes with small
amounts of a basic or acidic additive. The next most popular
modifier was acetonitrile, followed by 2-propanol. Ethanol is not
often used as a modifier, perhaps because its distribution is strictly
regulated and it may be difficult to obtain. However, at least one
group, that of Medfedovici et al., found that ethanol-modified CO2
provided a better separation than methanol-, acetonitrile-, or
2-propanol-modified CO2 for an acidic chiral pair (228).
The advantages of pcSFC for chiral chromatography can be
especially important in preparative separations of high-value-added
enantiomers. Saito et al. used preparatory-scale SFC on Chiralcel
OD to resolve milligram quantities of DL-flavanone (57). Problems
associated with residual solvents or solvent impurities are minimized in preparative-scale SFC. Other workers have described
the resolution of diasteriomers by pcSFC (230) and the separation
of enantiomers after derivatization with chiral reagents to form
diasteriomers (231). Alasandro described a pcSFC separation of
diastereomeric, antibacterial oxazolidinones using Chiralcel OD
(230). A separation was not achieved in the HPLC mode. A series
of chiral derivatization reagents for the determination of chiral
alcohols using achiral GC or SFC separations of the resulting
diasteriomers was described by Walther and Netscher (231).
SUPERCRITICAL FLUID EXTRACTION
The rapid development of SFE over the past 8-10 years
created a renewed interest in the evaluation of extraction methods.
While reduced solvent use is often promoted as the driving force
behind SFE, in actuality, the performance attributes (greater
selectivity, reduced time, quantitative yields, lower cost per
extraction, new capabilities) are what has driven the technology.
Several reviews present the state of analytical SFE (232-237).
The advances in SFE spurred the creation of several other new
extraction techniques, known by a variety of sometimes confusing
titles: accelerated solvent extraction (ASE), hot (subcritical) water
extraction, near-critical fluid extraction, enhanced-fluidity extraction, etc. Similar to the unified chromatography approach
discussed earlier, all of these extraction modes feature a single
commonality. Pressure is artificially imposed to allow temperatures greater than the normal boiling point of the extracting
solvent. This elevated temperature allows for higher solubilties,
faster diffusion, improved kinetics, and lower viscosities, all of
which aid in improving extraction yields. For purposes of this
discussion, traditional SFE using CO2 or similar fluids as the
primary extracting solvent under conditions near or above the
critical point is reviewed. The other extraction techniques will

be combined into a section on pressurized fluid extraction. (An
argument could be made that closed-vessel microwave-assisted
extraction can be considered pressurized fluid extraction.
However, in contemporary practice, the elevated pressure results
as a consequence of sample heating rather than being imposed
on the system. Since some controversy exists regarding whether
microwave energy provides any additional benefits, we chose to
omit this extraction mode in our review.)
Instrumentation, Techniques, and Performance. The
commercial market for extraction supplies and instrumentation
appears to be somewhat unsettled as vendors observe the changes
taking place in analytical extractions. However, vendor support
still remains strong. Dionex introduced accelerated solvent
extraction two years ago and continues to develop that field. Isco
developed a dual-mode feature to their automated SFE unit,
allowing both SFE and ASE operation from the same instrument.
Additionally, Isco acquired Suprex and continues to support the
whole line of Suprex SFE products. Other vendors maintain their
market presence, with Jasco increasing its U.S. presence and
several vendors, including Applied Separations and Supercritical
Fluid Technologies, attempting to bridge the gap between analytical-scale SFE and bench-scale engineering units. The Leco SFE
unit is described in a European patent (238). Aspects of
automating SFE are also discussed (239). For field studies, a
thermal pumping system (240) and infrared detection (241)
provide advantages.
Analyte-matrix interactions can be studied with SFE (242,
243) and modeled for polymer systems (244). Luque de Castro
and Tena developed strategies for extracting polar and ionic
compounds (245) while others discussed general method development in SFE (246, 247).
Field described the use of chemical derivatizations during SFE,
for example, to convert carboxyl, hydroxyl, sulfonic acid, and
amino moieties to their alkyl, acyl, and silyl derivatives (248). Such
analyte derivatizations may be necessary to improve analyte
solubility in the extracting fluid, to overcome analyte interactions
with the sample matrix, or to facilitate subsequent analysis.
Solute Collection. Postextraction analyte collection generally
takes on one of two forms: deposition onto a solid-phase trap or
into a collection solvent. Burford et al. developed a device for
adjustable flow control coupled with solvent collection (249), while
Wenclawiak et al. used a Dewar condenser to optimize collection
into organic solvents (250). Eckard and Taylor comprehensively
compared analyte collection onto a number of solid-phase traps
and found a mixture of Porapak Q and glass beads as the most
generally optimal (251). Two independent groups found that
octadecylsilane solid-phase traps worked best for the recovery of
pesticides and polychlorinated organics (252, 253). Gao et al.
compared a variety of collecting solvents and cooled, solid-phase
traps for the collection of PAHs following SFE (254). They found
temperature and collection solvent height to be important parameters.
Extracting Fluids. Little recent work has been reported on
the fundamental evaluation of supercritical fluids as extracting
solvents. In part, this can be attributed to the development of
the pressurized-fluid extraction methods, as well as the maturity
of SFE. Sterzenbach et al. devised an adsorption device to clean
their CO2 source and declared CO2 purity a moot issue for trace
analysis of chlorinated hydrocarbons (255). MacNaughton et al.
proposed a predictive method for choosing CO2 cosolvents for
the SFE of pesticides (256). In the search for alternatives to CO2,
Roth evaluated the thermodynamic properties of several hydrofluorocarbons and hydrochlorofluorocarbons (257).
SFE-Coupled Techniques. One of the attractive features
of SFE, especially with CO2 as the extracting fluid, is the ability
to directly couple the extraction method with subsequent analytical
methods in an overall sample measurement scheme. As attractive
as this capability may be, problems with the interfacing of SFE
with other techniques need to be addressed. These potential
problems prevent many users from fully utilizing this capability
and represent the thrust of most current research in this area.
(a) SFE/Chromatography. The direct coupling of SFE with
GC in an on-line approach is conceptually straightforward, assuming quantitative deposition of the extracted analyte into the
chromatographic inlet. Burford et al. reviewed the instrumentation and applications of on-line SFE/GC (258). Two studies
looked at the use of cryogenic analyte preconcentration traps prior
to SFE/GC (259, 260). Meanwhile, Lou et al. compared the
chromatographic performance of split/splitless and programmedtemperature, vaporizer injection methods in directly coupled SFE/
GC (261).
Only two papers addressed combining SFE with LC (262, 263).
The work reported by Ashraf-Khorassani et al. noted baseline
perturbations with UV detection due to solubility of the CO2
extracting fluid in aqueous LC mobile phases at low chromatographic flow rates (263).
(b) Other SFE-Coupled Techniques. Typically, extraction
methods must be followed by a separation technique prior to
subsequent analysis or detection. However, the combined selectivities afforded by both SFE and spectroscopic methods often
may render intermediate separations moot. Tilotta et al. described
an approach for SFE/FT-IR using a simple fiber-optic transmission
cell (264). Current and Tilotta applied the method to determine
total petroleum hydrocarbons in soil (265). Wetzel and Sweat
used an acousto-optic tunable near-IR filter to monitor the progress
of SFE (266). Liescheski used a flow-cell approach to IR and
monitored the vinylic C-H band to measure the iodine number
in edible oils (267). Liescheski et al. used the same approach to
characterize polyurethane fiber finishes (268).
Other spectroscopic methods were also used in conjunction
with SFE (269, 270). Tena and Valcarcel constructed a windowless fiber-optic-based flow cell similar to that previously described
to study SFE (269). The approach was used to screen soil
samples for PAH (271). Meanwhile, Dunham et al. modified an
LC fluorescence detector for use with SFE (270). The fluorescence measurements were limited to somewhat low pressures due
to both the detector cell construction and increasing CO2 emission
intensity as a function of pressure.
Finally, two groups combined SFE with enzyme-linked immunosorbent assays (ELISA) for the determination of pesticides (272,
273).
SFE Applications. Applications of analytical SFE are numerous and continue to focus on fossil fuels and environmental
samples, foods, natural products, and polymers. Many of these
applications have adopted the advances in SFE previously disAnalytical Chemistry, Vol. 70, No. 12, June 15, 1998
309R
cussed. In reviewing the SFE application areas during this review

period, we choose to classify the work by sample type rather than
analyte type.
(a) Fossil Fuel and Environmental Samples. Pesticides,
hydrocarbons, phenolics, and other compounds of general environmental importance remain of most interest to SFE practitioners.
VanBavel and Lindstrom (274) and Gartner et al. (275) each
presented general reviews of the field. Advancements in the
extraction of materials from soils can follow the modeling of such
systems. Montero et al. modeled their experimental data for the
desorption of contaminants from soils (276). They related the
effects of external mass transfer and intraparticle diffusion to the
overall extraction recovery. Rahme et al. considered axial dispersion, particle-fluid mass transfer, intraparticle diffusion, and
partition coefficients in comparing three kinetic models applied
to the SFE of soil contaminants (277). Riley et al. examined the
airborne and solid wastes generated in comparing SFE with
Soxhlet procedures for the extraction of organic compounds from
sediments (278).
Hydrocarbons, including aromatics, and phenolics are especially amenable to extraction with supercritical fluids. Two reviews
addressed the SFE of PAH from soils (279, 280). Optimization
approaches for this extraction problem, including a central
composite experimental design, evaluated the effects of different
extraction parameters (281-285). Ashraf-Khorassani et al. studied the effects of pressure, temperature, modifier type, modifier
concentration, and sample matrix for optimizing the extraction
efficiency of phenolics from different soils (286). CO2 cosolvents
may be needed in solubilizing analytes or in overcoming analytematrix interactions. Hollender et al. evaluated 12 CO2/modifier
mixtures for the removal of PAH from soils and found that acidic
or basic cosolvents provided the highest yields (287). Friedrich
et al. uncovered binary mixtures containing only 1% additives in
organic solvents for an extracting fluid optimized for PAH that
they claim is nearly matrix independent (288). Soil matrixes
with high amounts of water can affect SFE recovery of PAH (289).
At water levels greater than 10%, increasing temperature increased
the extraction yields of higher molecular mass PAH.
Several researchers compared SFE with other extraction
procedures for the analytical extraction of PAH and phenolics from
soils. Lage et al. found no quantitative difference between SFE
and conventional liquid extraction methods for extracting PAH
from water-soluble smoke (290). Both SFE and microwaveassisted extraction performed better than a standard sonication
procedure for recovering phenolics from a variety of soils (291).
Increasing the methanol modifier content in CO2 into the
enhanced-fluidity region (greater than 20% methanol in CO2)
provided some advantages for extracting PAH and phenolics
(292-294). In these enhanced-fluidity extractions, methanol
content and temperature both improved the extraction yields and
decreased the extraction times. In a similar manner, Deuster et
al. described supercritical-assisted liquid extraction of nitroaromatics and polycyclic aromatics in soil (297). Lopez-Avila et al.
compared SFE with microwave-assisted extraction, sonication, and
Soxhlet methods for a number of compounds adsorbed onto soil
(298).
A number of researchers explored other aspects of SFE for
determining hydrocarbons. Remmler et al. determined over 100
310R
constituents in soils and sludges near petrochemical plants (299).

They used a combination of SFE, GC/MS, and thermal methods
for the characterization. Marine sediment extracted with SFE and
characterized with GC/MS focused on the extracted PAH components (300). Wenclawiak et al. reported toluene as a modifier
in both CO2 (SFE) or dimethyl ether (Soxhlet) for improving the
extractability of higher molecular weight PAHs (301). GC/MS
was used to study PAH and organic acids extracted from creosoted
timber and activated carbon (302, 303). Kado et al. combined
SFE with bioassays and other screening methods to study vaporphase compounds from diesel exhaust (304). Bowadt et al.
demonstrated a field-portable SFE procedure for determining
PAHs in soils (305).
Pesticides and herbicides represent another area of environmental interest where SFE is having significant impact. Stuart et
al. (306) and Camel (307) reviewed the use of SFE in agrochemical studies. The interaction of somewhat polar pesticides with
soil matrixes is subject to much research interest. Dean et al.
looked at the use of modified fluids for overcoming analytesample interactions in the SFE of organochlorine and organophosphorus pesticides (308, 309). Other SFE studies examined
the role of factors such as temperature, pressure, and modifier
on the optimization of extracting pesticide residues in soils (310)
and dicofol residues in fish tissue (311) and the use of supercritical
fluoroform for extracting sulfonamides (312). Stearman et al.
rapidly screened for soil herbicides by combining SFE with ELISA
(313, 314), while Koeber and Niessner used SFE/TLC for the
same purpose (315). Jimenez-Carmona et al. also combined SFE
with immunoassay (316). Both CO2 and water were used for their
extraction of chlorpyrifos metabolites. Triazine herbicides generally required the addition of methanol to the CO2 extracting phase
for complete extraction from soils (317-320). However, when
significant soil moisture was present, neat CO2 can be used for
extraction purposes (321). Mougin et al. directly coupled the SFE
step with LC to achieve extraction efficiencies of 99.5% of triazines
spiked onto soil samples (322). SFE methods developed for the
determination of organochlorine pesticides were applied to soils
(323), oil seeds (324), air (325), and tobacco (326). Ling and
Liao investigated the total organic carbon composition, pH,
moisture, and particle size on the SFE of organochlorine pesticides
from sulfur-containing soils (327). Lopez-Avila et al. converted
chlorophenoxy acid herbicides to their pentafluorobenzyl bromide
esters prior to using CO2 to extract these compounds from soil
(328). Two papers reported the SFE extraction of carbamate
pesticides from soils (329, 330). Other pesticide-related SFE
applications included the extraction of naled, methyleugenol, and
cuelure in soils (331), azadirachtin in soils and insects (332),
cyanazine herbicides in soils (333), metribuzin in soil (334),
acifluorfen in organic soils (335), chlorsulfuron and tribenuronmethyl in soil (336), and nitrogen- or phosphorus-containing
pesticides in wet soils (337).
Halogenated organics, particularly PCBs, PCDDs, and PCDFs,
are also of special interest to environmental scientists and are
readily amenable to extraction by SFE. Regarding the SFE
performance aspects, Ashraf-Khorassani and Taylor studied the
modes of adding fluid modifiers (338). They noted that spiking
the sample with organic cosolvent yields higher results in the SFE
of PCBs from sediment than the on-line fluid-mixing approach.
Hartonen et al. explored various parameters influencing collection

of polychlorinated pollutants onto solid-phase traps following SFE
and found the highest recoveries when they used Florisil (339).
Four independent studies reported SFE to be superior to Soxhlet
for extracting PCBs from soils or ash samples (340-343).
Additional studies presented SFE followed by GC/MS for characterizing PCBs in street dust (344), parts-per-trillion analysis of
PCBs and organochlorine pesticides in marine sediments (345),
and a fractional factorial approach to optimization and modifier
selection for extracting chlorinated benzenes and hexachlorocyclohexanes from soil (346).
Organometallics, metal chelates, and metal ions remain an
interesting environmental application of SFE, as reviewed by
Ashraf-Khorassani et al. (347). Cela-Torrijos studied the kinetics
of removing methylmercury from marine sediments prior to GC
analysis (348). Emteborg et al. extracted methylmercury from
sediments with SFE, derivatizing the sample with butylmagnesium
chloride prior to GC with microwave-induced plasma atomic
emission spectrometry (349). Dithiocarbamates and fluorinated
-diketones served to chelate transition metal ions for subsequent
SFE with CO2 and methanol modifier (350). Lopez-Avila et al.
coordinated a multilaboratory study of the SFE, followed by GC
with atomic emission detection, of organotin compounds (351).
Finally, a variety of other environmental applications were
reported during this period. Barzegar et al. explored a number
of SFE parameters influencing the extraction of nitro-PAHs (352),
while Wujcik and Seiber examined similar parameters in extracting 2,4,6-trinitrotoluene and 1,3,5-trinitrobenzene (353). Reighard
and Olesik compared SFE and enhanced-fluidity extractions for
11 phenols and nitroaromatics (51). Li et al. used SFE to
determine the volatile compounds that usually remain undetected
in pulverized coal samples (355). SFE desorption of coal smoke
pollutant trapped onto Porapak P was reported by Cui et al. (356).
Burford et al. directly transferred the SFE effluent onto an opentubular GC column in the determination of gasoline- and dieselrange organics (357). Alcantara-Licudine et al. used CO2 with
organic solvents and inorganic salts or chelating agents to extract
xanthere dyes from soil (358). Fernandez et al. studied the
decline in the presence of a quaternary ammonium surfactant in
sewage sludge with SFE (359), and Breen et al. investigated the
effect of methanol modifier concentration on this extraction (360).
Sklarew et al. compared SFE with Soxhlet in the characterization
of tributyl phosphate and lard oil spiked into sediments (361).
(b) Foods and Food Products. Beyond environmental
samples, application of SFE to samples of food interest remains a
major emphasis. The popularity of SFE for these applications can
be directly attributed to the elimination of organic solvents, the
high solubility of lipophilic matter in supercritical CO2, and the
low temperatures which allow for flavor analysis. Valcarcel and
Tena comprehensively reviewed several of these applications
(362).
The use of SFE for the determination of fats in food products
is one of the most prevalent applications in the field. Eller and
King provided a review of this application (363). It has become
so prevalent that an undergraduate laboratory exercise is being
advocated (364). Liescheski reviewed the on-line coupling of SFE
and IR for the characterization of lipid products (365). Propane
can be favorable to the use of CO2 for the removal of oils from oil
seeds (366). Fats from meat samples can be characterized by

SFE methods for nutrient analysis by transesterification and GC
analysis (367) or to determine exposure to ionizing radiation by
evaluating the volatile hydrocarbons in the meat lipids (368).
Lipases can be added directly to SFE vessels along with the
sample to provide an in situ methylation for GC determination of
fatty acid methyl esters (369, 370). Berg et al. used their SFE
method to characterize the lipid classes in meat (371). Montanari
et al. reported a selective extraction of phospholipids from other
lipid components with ethanol as a CO2 modifier (372).
Flavor compounds and other food volatiles are relatively
straightforward to extract with SFE. SFE can be favorable due
to the temperature and concentration advantages of using CO2,
as well as the selectivity advantages and the ability to directly
couple to GC analysis. Perhaps most remarkable with these
applications of SFE to flavor analysis is simply the diversity of
samples: breakfast cereal (373), raspberries (374), chilies and
paprika (375), eucalyptus (376), cinnamon (377), milk and dairy
products (378), wines and musts (379), meat (380), Swiss cheese
(381), and roasted peanuts (382).
Just as SFE found utility in the determination of soil-bound
pesticides and herbicides, the technique found application in the
determination of these same compounds in food products. For
example, Lehotay reviewed the SFE of pesticide residues in fruits
and vegetables (383, 384). Because of the inherent water content
in produce samples, where pesticides may be found, drying agents
become especially important. Eller and Lehotay compared Hydromatrix and magnesium sulfate for use in the SFE of multiple
pesticide residues in produce (385). Valverde-Garcia et al. used
magnesium sulfate as the drying agent in their SFE determination
of a number of pesticides in vegetables (386). Lehotay and Lee
evaluated a fibrous cellulose drying agent for determining
pesticides in tomato samples by SFE and pressurized liquid
extraction (387). Pearce et al. developed a rapid SFE method
for the determination of a number of pesticides and fungicides in
strawberries (388). An additional multiple-residue method, developed for egg samples, has been reported by Wigfield et al.
(389). Poustka et al. reported the SFE removal of organophosphates from cereals using pure CO2 (390). Meanwhile Hopper
used CO2 modified with acetonitrile to selectively extract organophosphates and organochlorine pesticides from fats (391).
Another researcher isolated sub-parts-per-million levels of sulfonamides in whole egg samples with CO2 and Hydromatrix drying
agent (392). Liu et al. reported a unique drying agent, defatted
cotton, for the SFE of five carbamate pesticides in apples (393).
Stefani et al. also looked for pesticides in apples, developing an
SFE method for 92 different pesticides (394). Din et al. explored
the SFE of sulfamethazine metabolites in meat tissues (395). Meat
samples, as well as lettuce, were also extracted by Argauer et al.
for the determination of pyrethroids (396). Lancas et al. used
CO2 SFE with acetone modifier for the extraction of acidic
residues, 2,4-dichlorophenoxyacetic acid, and Dicamba in sugar
cane, rice, and corn (397). Other applications of the SFE removal
of pesticide and related residues in food samples included the
SFE of Atabron in cabbage (398), norflurazon and oxadixyl in
sugar cane and grapes (399), and fungicides in fruits (400) and
an ion-pair SFE of clenbuterol from a number of food samples
(401).
311R
A variety of other SFE applications aimed at food quality has

been reported. Fiddler and Pensabene used SFE to examine
N-nitrosamine levels in bacon (402). King et al. used analytical
SFE as a step in the production of tocopherol concentrates (403).
Trichothecene mycotoxins were of interest to Jarvenpaa et al.
(404), while Marx and Fabricius used SFE for the semiquantitative
determination of guarana in foods (405). Stolker et al. reviewed
the use of SFE in the characterization of veterinary drugs and
growth-promoting agents in food and biological samples (406).
Another report examined sample dehydration for the SFE of drug
residues from chicken liver (407). Lopez-Avila and Bendicto used
the SFE-ELISA approach to screen for veterinary drugs in dry
milk powder (408). Taylor et al. applied SFE to the extractive
removal of aflatoxin M1 from beef liver samples (409). CO2 with
methanol was used by Huopalahti et al. in the determination of
mycotoxins in feeds (410). CO2 modifiers were studied for the
extraction of fumonisin B1 in corn dust samples (411), and
Holcomb et al. used SFE and LC to determine aflatoxins in corn
(412). Gawdzik et al. fractionated furanocoumarins in fruit with
SFE (413). Other researchers extracted carotenoids from carrots
using SFE (414). Quantitative recovery of caffeine in Chinese
tea has also been reported (415). Moderate SFE conditions were
all that was required for the extraction of vitamin A palmitate in
cereal products (416). Burri et al. injected their SFE sample of
vitamin A and -carotene extracted from beef liver directly onto
LC without sample cleanup (417). Extracted cyclobutanones were
used as chemical markers in the SFE identification of irradiated
poultry samples (418). Din et al. reported the need to freeze-dry
beef samples prior to the SFE of anabolic steroids (419). Another
report of extracting steroids from beef tissue combined SFE with
sample cleanup by solid-phase extraction (420). Lancas et al.
presented the SFE of chlorothalonil residues in apples (421). Van
der Velde et al. used SFE as a cleanup technique for the partsper-trillion determination of PCBs in fatty samples (422). PAHs
in smoked and broiled fish were isolated via SFE by Jaevenpaeae
et al. (423). Marsin et al. studied the effect of pod storage in
quantifying the pyrazines in roasted cocoa beans (424). Barden
combined resin-mediated methylation and SFE for the subsequent
GC determination of organic acids in fruit juices (425).
(c) Botanicals and Natural Products. Nonfood applications
of SFE to natural products tend to rely on the advantages of
coupling SFE with chromatographic techniques and the lower
probability of thermal sample degradation. Smith (426) and
Modey et al. (427) each comprehensively reviewed this application
area of SFE. Calvey and Block reviewed the use of SFE to obtain
spice extracts (428), and Reverchon reviewed SFE for the
fractionation of essential oils (429). As with the flavor extraction
in foods, the shear sample diversity of SFE applications to natural
product samples can be overwhelming. Gawdzik et al. reported
the clean fractionation of essential oils and furanocoumarins from
Archangelica off. (430). They also identified 45 compounds by
GC/MS in the SFE extract of the essential oil from the same fruit
(431). Semiond et al. compared SFE with alcohol extractions of
safranal in saffron of different geographic origins (432). Lancas
et al. focused on analyte collection in the SFE of pesticide residues
in tobacco (433) and used capillary zone electrophoresis to
determine carbamate pesticide residues in these extracts (434).
Liu obtained a crude fraction of anethole for further purification
312R
from star anise using SFE (435). Van Beek and Taylor obtained
a standard extract of five terpenes in Ginkgo biloba (436). Krizsan
et al. combined SFE with LC for the characterization of anthraquinone derivatives in root and plant cell culture samples
(437). A kinetic extraction model was applied and SFE parameters were explored for the extraction of a monoterpene from a
ground wood sample (438, 439). Sargenti and Lancas examined
a variety of CO2 modifiers for an essential oil extraction (440).
Anitescu et al. compared SFE with steam distillation for the
isolation of essential oils (441). Samples obtained from SFE had
a greater level of heavy hydrocarbons, fatty acids, nitrogenated
compounds, and sesquiterpenes than those obtained by steam
distillation or simultaneous distillation-extraction for a flower
extracts (442, 443). However, SFE recovered higher levels of
natural antioxidants in rosemary than sonication in liquid solvents
(444). Choi et al. combined SFE with five different bioassays to
examine bioactive compounds from Korean natural products
(445). Ma et al. examined the chemical constituents of a Chinese
herbal medicine with SFE followed by GC/MS (446). Kohler et
al. isolated a drug precursor with SFE followed by SFC characterization (447). El-Sharkawy et al. used SFE to remove the color
pigments in seeds (448). Lopez-Avila et al. compared pure CO2
and CO2 modified with methanol for extracting alkaloids (449).
Increasing selectivity by variation of methanol amount was used
by Ashraf-Khorassani and Taylor in the determination of michellamines from leaves (450). Ranade presented thin-layer chromatography as a means of screening natural products extracts
obtained with SFE (451). Wenclawiak et al. performed an in situ
transesterification of natural pyrethrins prior to GC/MS (452).
(d) Biotic (Animal) Fluids and Tissues. Animal tissues
often present an extraction challenge due to the potential for
coextracting lipids, proteins, and other extraneous material. The
selectivity of SFE can address this concern. Meyer and Kleiboehmer presented a series of papers using SFE to remove pentachlorophenol residues from leather for analysis (453-456).
Lindstroem et al. examined polychlorinated materials in human
tissue with SFE, LC, and GC (457, 458). Hale et al. looked at
these polychlorinated compounds in osprey and fish tissues (459)
and Atuma et al. explored organochlorine pesticides in fish (460).
Other analytes were also examined in fish tissue, including
organotin compounds (461) and lipids (462). Jones and McCoy
evaluated SFE for the extraction of pesticides in honeybees (463).
Huopalahti and Henion characterized anabolic steroids in bovine
tissues (464). Jacobson et al. used supercritical ammonia for the
rapid characterization of radiolabeled metabolites in tissues (58,
145).
The use of SFE of hair samples for the determination of drugs
of abuse in humans has found some interest. Staub reviewed this
field (465). Veuthey et al. developed an SFE/GC/MS procedure
for the determination of opiates in urine and hair (466), while
Morrison et al. combined SFE with radioimmunoassay to specifically screen for cocaine residues in hair at levels as low as 0.07
ng/mg (467). Cirimele et al. also examined SFE of opiates from
hair and obtained best results with a modifier containing methanol,
triethylamine, and water (468).
SFE can also be applied to the determination of drug metabolites in serum and other biological fluids. This is exemplified by
the SFE of benzodiazepines, anabolic agents, and nonsteroidal
antiinflammatory drugs in water and serum (469). Scott and

Oliver presented a similar SFE method for the analysis of
temazepam in whole blood (470). Hartonen and Riekkola
developed a procedure that included solid-phase extraction, SFE,
in situ acetylation, and GC/MS for determining -blockers in urine
(471).
(e) Polymers. Polymer applications of SFE generally fall into
one of two categories: extraction of the oligomeric material or
removal of additives from the polymer matrix. SFE can uniquely
address this areas because of the high solubility of some polymers
in supercritical CO2 and because of the high diffusion (at low
temperatures) available with supercritical extracting fluids. Bruna
reviewed the use of SFE in polymer technology (472). Lou et al.
thoroughly investigated the effects of a number of SFE parameters
for extracting additives in polyethylene and developed a two-film
extraction theory considering mass transfer across a phase
boundary (473). Several researchers used supercritical CO2 to
extract additives, including phthalates, from poly(vinyl chloride)
(474-476). Sekinger et al. determined total extractables in
styrene-butadiene rubber with SFE (477). Clifford et al. performed SFE of polymers both at constant density and with linearly
increasing density with time for the fractionation of polymers
(478).
In more unique uses of SFE in polymer applications, Kazarian
et al. developed an in situ spectroscopic method for studying SFE
drying and dyeing of poly(methyl methacrylate) (479). Roston
et al. assayed a polymeric controlled-release drug formulation with
SFE (480) and Nerin et al. quantitatively determined pesticides
in postconsumer recycled plastics (481).
(f) Aqueous Samples. The extraction of liquid samples using
SFE is done either by adsorbing the liquid onto a sorbent material
or by direct means. The direct extraction approach is not typically
used and differs from other forms of SFE, especially since these
extractions will tend to be driven strictly by partitioning into the
supercritical extracting fluid without a strong diffusion driving
force. Janda et al. reviewed these aspects of direct SFE of aqueous
samples (482). Ramsey et al. coupled their aqueous SFE on-line
with LC/MS for the parts-per-billion-level analysis of drugs in
water (483). Aqueous SFE was coupled with FT-IR for monitoring
hydrocarbons in water at parts-per-million levels (484). AshrafKhorassani et al. performed in situ chelation for the direct SFE
of aqueous solutions of Ni2+ and Cu2+ (485). Toews et al. studied
the effect of pH on the SFE efficiency of metals and ionizable
species in water-containing systems (486), while Combs et al.
looked at pH effects for extracting aqueous phenols (487). The
extractability of PAH by SFE from water samples was studied
(488). In another case, chlorinated volatile organic compounds
in water were trapped onto an adsorbent prior to SFE (489). Other
instances where aqueous samples were adsorbed onto support
materials included the following: trapping onto an octadecylsilane
LC column for steroid determinations (490), filtering-suspendedsolids isolation for detecting organics in water (491, 492) and a
comparison of filters for this application (493), and evaluation of
a polymeric phase prior to SFE of water-borne pesticides (494).
(g) Miscellaneous Applications. Applications of SFE to
determine metal compounds is becoming quite popular. Smart
et al. (495) and Wai and Wang (496) covered these applications
in review articles. Wenclawiak et al. studied the supercritical fluid
behavior of different ligands on rhodium and extracted rhodium
and palladium -diketonates (497). Oezel et al. also used
-diketonates for metals SFE, comparing fluorinated and nonfluorinated chelating agents (498). Glennon et al. investigated
hydrooxamic acids as chelating agents for SFE of metals, rather
than the more commonly used dithiocarbamates and -diketonates
(499).
In drug-related applications of SFE, Roston and Sun extracted
an HIV protease inhibitor from animal feed (500). Eckard and
Taylor performed an ion-pairing SFE of pseudoephedrine hydrochloride (501). Karlsson et al. reviewed the field of SFE for
pharmaceutical formulations (502).
Finally, Scalia et al. analyzed triclosan antibacterials in deodorants and soaps (503). Jones investigated an SFE cleanup
procedure for determining pesticides in wool (504). Khundker
et al. optimized the SFE of fluconazole in animal feed with a
fractional factorial design approach (505). Beck and Moore
compared SFE and Soxhlet methods for characterizing impurities
on cotton fibers (506).
Pressurized Fluid Extraction. As discussed earlier, a
number of newer extraction methods are being developed which
share the feature of imposing a pressure so that elevated
temperatures can be used during extraction. These techniques
go by a variety of names such as accelerated solvent extraction,
supercritical assisted liquid extraction, high-pressure solvent
extraction, enhanced solvent extraction, etc. Yet the techniques
are fundamentally the same. The Dionex approach to ASE has
had two issued patents (507, 508) and was fundamentally
described two years ago (509). These techniques are generally
designed for environmental analysis, as reviewed by Hoefler (510)
and Reighard and Olesik (511). Kreisselmeier and Duerbeck
applied the method to extract alkylphenols and linear alkylbenzenesulfonates from sediments (512, 513). Lou et al. examined
ASE parameters for the extraction of monomers and oligomers
from polymers (514). PAHs and other organics of environmental
interest were the subject of research performed by Dean (515),
Huau and Compiano (516), David and Seiber (517), Dean et al.
(518), Creutznacher (519), Ezzell et al. (520), Fisher et al. (521),
Conte et al. (522), Heemken et al. (523), Obana et al. (524),
Wagenaar et al. (525), Friedrich and Kleibohmer (526, 527),
Richter et al. (528), Knowles et al. (529), Ezzell and Richter (530),
Jensen et al. (531), Pyle and Marcus (532), and Popp et al. (533).
Of final interest is development of hot, subcritical water
extraction (2), which has also been combined with SPME (3).
This approach to extraction is fundamentally the same as the
others discussed in this review, with one significant difference.
As water is heated, the dielectric constant (and hence, the effective
polarity) drops to the point where water behaves like an organiclike solvent. This allows a wide range of solvent polarity available
for extraction, along with the diffusion, viscosity, and other
advantages. As materials compatibility issues and a more thorough theoretical basis are devised, it is expected that this approach
will play a significant role in analytical extractions.
313R
Thomas L. Chester received his B.S. in chemistry from the Florida

State University in 1971, spent a year at the Baychem Corp. (now Bayer)
in Charleston, SC, and then began graduate studies at the University of
Florida under the direction of J. D. Winefordner. He received the Ph.D.
degree in 1976 and joined Procter & Gamble where he is currently Head
of the Separations and Optical Spectroscopy Section, Corporate Research
Division, at the Miami Valley Laboratories. He has been active in SFC
research and application since 1982 and is currently the Chair of the
Chromatography and Separations Chemistry Subdivision (Division of
Analytical Chemistry) of the ACS.
J. David Pinkston came to Procter & Gamble in 1985 after receiving

his Ph.D. from Michigan State University. Before beginning his graduate
studies in 1980, he spend a year working with G. Spiteller at the University
of Bayreuth in West Germany as a DAAD Fellow. He received his B.S.
in chemistry and math in 1979 from Ouachita Baptist University in
Arkadelphia, AR. He is currently a Senior Scientist in Procter & Gambles
Corporate Research Division at the Miami Valley Laboratories. His
research interests include the development and application of SFC and
SFE and the coupling of microcolumn separation methods with MS.
Douglas E. Raynie is a Senior Scientist in the Corporate Research
Division of Procter & Gamble. He received his Ph.D. in analytical
chemistry in 1990 from Brigham Young University under the direction
of Milton L. Lee. He has an M.S. in analytical chemistry from South
Dakota State University and a B.A. in biology and chemistry from
Augustana (SD) College. He is on the Editorial Advisory Board of the
Journal of Microcolumn Separations. His research interests include
analytical uses of supercritical fluids, enhanced sample preparation
procedures, high-resolution chromatography, and chromatographic and
separations theory.
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Anal. Chem.

1998, 70, 301R-319R

Supercritical Fluid Chromatography and Extraction

This critical review covers the literature appearing since our

1998 American Chemical Society

raphy to signify techniques performed with control of the column

SUPERCRITICAL FLUID CHROMATOGRAPHY

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

tivity shifts in SFC with polymeric stationary phases (23). Kautz

stationary phases. Direct comparisons of LC and SFC should be

high enough to prevent boiling. In enhanced-fluidity LC, CO2 is

(78). Carlsson et al. developed a peak-compression injection for

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

retention gap method of direct injection and a direct-fluid MS

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

used higher chromatographic efficiency, by means of four columns

% (53). Raising the temperature had much the same effect as

(194), salbutamol sulfate and related compounds (195), paclitaxel

212). Resolution generally decreases as column temperature

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

(carbobenzyloxy)-2,6-diaminopimelic acid on Chiralpak AD (228),

critical point is reviewed. The other extraction techniques will

cussed. In reviewing the SFE application areas during this review

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

constituents in soils and sludges near petrochemical plants (299).

Hartonen et al. explored various parameters influencing collection

seeds (366). Fats from meat samples can be characterized by

A variety of other SFE applications aimed at food quality has

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

antiinflammatory drugs in water and serum (469). Scott and

Thomas L. Chester received his B.S. in chemistry from the Florida

J. David Pinkston came to Procter & Gamble in 1985 after receiving

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

(81) Robson, M. M.; Raynor, M. W.; Bartle, K. D.; Clifford, A. A. J.

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

(219) Garcia, K. E.; Medvedovici, A.; Ferraz, V.; Sandra, P. J. High

(269) Tena, M. T.; Valcarcel, M. J. Chromatogr. 1996, 753, 299-305.

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

(416) Schneiderman, M. A.; Sharma, A. K.; Locke, D. C. J. Chromatogr.

(465) Staub, C. Forensic Sci. Int. 1997, 84, 295-304.

(501) Eckard, P. R.; Taylor, L. T. J. Pharm. Biomed. Anal. 1997, 15,

Analytical Chemistry, Vol. 70, No. 12, June 15, 1998

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