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Frances 5.

Sterrett
Hofstra College
The Nature of Essential Oils
Hempstead, N e w York
I. Production

The word "essential oils" undoubtedly The term production here refen to the various
originates from the Latin "quinta essentia" (quintes- methods of separation of essential oils from the aromatic
sence), the fifth element, the essence of things. Al- plant materials. These volatile oils are formed mostly
chemists believed essential, ethereal, or volatile oils to in the secretory cells or reservoirs, internal or external
be the most condensed form of the individual character- glands of flowers, leaves, bark, wood, root, or fruit of an
istics of the plant or drug. aromatic plant. Essential oils originate in practically
Since antiquity man has been mystified and intrigued every part of the world. Many are produced in remote
by essential oils and has made great efforts to obtain geographical areas under exceptionally primitive con-
them. Today as a result of many years of research ditions as an enterprise to supplement the family in-
these oils have become truly indispensable and essential come.
to our way of life. During the course of a single day,
from the first day of existence to the last, every living Table 1. Important Essential Oils
person in this country uses or consumes many of these Abies albh (pine) Labdanum Leaf
substances. They have a variety of applications in al- cone
leaf (needle)
Labdanum
Laurel Leaf
most all industrial and consumer products, from rubber Acacia flower
Ajowan
Lavandin
Lavender
baby pants, food and toilet preparations to embalming Ailsnioe
Almond (bitter)
Lemonerass
Lemon"'
fluids. Essential oils are used mostly for their sensory Ambretti seed' Lily (concrete and absolute)
Angdioa root Lime (distilled and oddpressed1
quality, but often also for their antibacterial and anti- Angelica seed Linaloe seed
Anyustors bark Lim.10e wood
fungicidal action. They are mainly of botanical origin,
composed of the organoleptic principles which contrib-
Anise seed
Arnica root
Balm
...-
Lovage root
xr"""uv
Mandarin
ute to the odor and flavor of the aromatic plant mate- Balsam (different typed
B a d (different tyge.)
Marjoram (a?&)
Marjoram (wrld)
rial; there are only very few exceptions of animal origin, Bayberry Mimosa Rawer
such as musk, civet, and ambergris.
Bay laurel
Bay leaf M".k;oot
..
Mint [different tvoesl
norgarnot mint Mustard seed
The term "oil" probably originated from observing Bergamot ..,....
M"rrh
that some of the glands or intercellular spaces in plant Birch (sweet) Myrtle
niroi, tar Ncroli bigarade
tissues are filled with oily droplets, similar to fatty or Bois de rose
Boineoeamphor
Nutmeg
oak moss (ooncrete and abeolute)
fixed oils. Essential oils and fixed oils have in common Buohu leaf
Cabreuva
Olibanum
Onion
the properties that they are nonmiscible with (and Cajunut 0pophne.x
Calhmus Orsnge (bitter) blossom
usually lighter than) water, and soluble in ether and Cslnphor (Neroli bisarade oil) ,
Carnnhor leaf Orange (bitter) leaf (Petltsrain)
many organic solvents. On the other hand, the compo- orange (bitter)
sition and properties of these volatile oils differ greatly Car&& seed or&"gcb e e t )
Carm.tion flower origsnum
from fixed or fatty oils, the former consisting of various Carrot seed
Cassia
orris root
Paimarosa
mixtures of different types of compounds, the latter Catni"
Cedar leaf
Parsley herb
Parsley seed
being for the most part glycerides of fatty acids or Cedarwood Patehouly
Celery seed Pennyroyal
paraffin oils. Essential oils are generally liquid (some- Cbhmomille (German and Roman) P,,,,,,i"t
Pepper bemy(different type4
Cirenopodiurn (American wormaeed
times semisolid or even solid) and, a t ordinary tem- oil) prtitzrain biaarade
perature, volatile. If a drop of essential oil and one of Cherry laurel Pin&ta ber&
Cinnamon bark pirnenta leaf
fatty acid are put on blotting paper, both a t first will Cinnamon leaf
Citronella
Pine needle (different types1
Pine root
leave an "oily" spot. The fatty-oil spot will remain CLsry sage
Clove (bud)
pinetar
Rose (distilled, also oonorete and
transparent to light, but the essential-oil spot will be- Clove l e d absolute)
Clove stem Roeemary
come almost invisible in a short time, retaining only Coriander seed Rosewood
costus root Rue
the non-volatile constituents which have an odor pecul- Cllmin seed Sage
iar to the particular ethereal oil applied. There exist CYP~~SP Sandalwood
Dill herb
in scientific literature many references to essential oils, Dill seed
Elomi
perfumes, and flavoring materials (1-10). Table 1 Ertragon
Eucalyptus (different types)
gives a list of the most important essential oils used Fennel seed
Fir (Siberian)
today. For the botanical classification of essential-oil Gariio
Geranium
plants, a list of plant families and genera is available Gingergrass
Ginper root
(11). Gramfruit
Hemlock
Honeysuckle (concrete s n d absolute)
This ia the firat of a two-part paper on essential oils. I n the next Hops
Horsemint
issue chemical constituents and analysis will be reported. Ae- EIorseradish
knowledgment is gratefully made to Dr. Ernest Guenther for Jasmine flower
Jonquil flower
valuable suggestions. Juniper berry

Volume 39, Number 4, April 1962 / 203


Methods of Production done by hand or by machine. I n Florida and Califor-
nia (9, 10) modern, elaborate and ingenious machines
The methods of production are complicated and keep the peel separated from the juice, thus producing
practices vary, depending on plant material, the type of the highest quality of "cold pressed" oils, such as sweet
essential oil to be obtained, and availability of equip- and bitter orange, lemon, grapefruit, mandarin, tange-
ment. There are three basic methods of production: rine, bergamot, and lime. The oil produced by this
steam distillation, expression and extraction. method at a yield of 1-5 kilogram per ton of fruit con-
Steam distillation. Proper preparation of the plant tains large amounts of waxes. The waste peel (after
material is of great importance, so that more rapid dis- expression) still holds substantial quantities of oil as
tillation, higher yields, and better quality oils will result, only 10-2070 of the oil contained in the peel is recov-
and lower fuel consumption will be achieved as well ered by expression. To obtain the balance of the oil,
(12-14). Since the essential oil is not distributed the peel (after expression) is submitted to steam distil-
evenly throughout the plant material, it is often neces- lation, which process yields the so-called distilled citrus
sary to mechanically rupture as many plant cell walls oils; their quality is inferior to that of the cold-pressed
as possible to render the volatile oil accessible to the citrus oils.
passing steam. The exact degree of comminution (the Extraction. Most essential oils are isolated by steam
mechanical breaking up) of the particular plant mate- distillation. However, some of the more delicate flow-
rial varies. Flower petals and most leaves (which are ers (such as jasmine, tuberose, violet, jonquil, narcissus,
relatively thin) can be distilled without comminution, mimosa, acacia, gardenia, hyacinth, etc.) when distilled
seeds must be crushed, root stalks and woody material yield either practically no oil or oil of inferior quality.
must he cut into small pieces. The comminuted mate- The action of steam or boiling water on the flower
rial must be distilled as soon as possible to minimize material apparently causes the constituents of the essen-
evaporation of oil and possible chemical changes of con- tial oils to hydrolyze, thermo-decompose, polymerize,
stituents. For some oils the plant material may be used resinify, etc., and the somewhat water-soluble constit-
for distillation immediately after picking; sometimes uents (such as phenyl ethyl alcohol or eugenol) are lost
the plant must be air dried or sernidried. in the distilling water, thus rendering such oils actually
Even after the plant material is well comminuted, useless since they do not represent the natural oil as it
those plant cells which are not damaged have a tend- occurs in the flower. Therefore, the more delicate
ency to retain some oil, and thus only the essential oil natural flower oils must be extracted. There are es-
present on the surface is available for the passing steam. sentially three methods of extraction: enfleuwge (cold
For this reason the plant tissues are often permitted to maceration), hot maceration, and extraction with vol-
come in contact with the boiling water during distil- atile solvents.
lation. The oil then diffuses through the surrounding Enfleurage and hot maceration (8, 17) are based on
membrane, bringing more volatile oil in contact with the property of fats (such as lard and tallow) to absorb
the steam and in this way improving the yield. On the volatile odoriferous constituents of flowers. This
the other hand, large amounts of boiling water in con- was recognized empirically hundreds of years ago when
tact with comparatively small amounts of essential oil flowers were treated by hot or cold maceration to yield
may upset the equilibrium condition (water ester + + fragrant pomades. Today these methods of extraction
alcohol + acid) of the essential oil constituents. with fat are obsolete. Since they are complicated and
Hydrolysis of the esters present in the original oil may involve much manual labor (which is costly) only in the
occur; the acid thus formed could possibly cause alter- region of Grasse, Southern France, are they still used
ation of some of the other constituents present in the and there on a very limited scale.
oil. However, since these hydrolysis reactions have a Hot and cold maceration have been almost com-
comparatively slow rate, a minimum contact with pletely replaced by extraction with volatile solvents
boiling water may in certain cases be preferred, using (18). This method is based on the fact that volatile
direct steam distillation, with the steam generated in a solvents such as petroleum ether penetrate the petals
separate still. Since practically all essential oil con- and dissolve all of the natural perfume, also the waxes
stituents are unstable at high temperature (many and coloring matters. The fresh flowers are extracted
isomerize, polymerize, and oxidize readily), the ideal dis- several times with a carefully purified solvent, which is
tillation therefore is one in which the diffusion rate is subsequently removed, usually by vacuum distillation.
high, while hydrolysis and thermal decomposition are The remaining product is a semisolid concentrated
kept at a minimum. I n general it is desirable to main- flower oil known as "concrete." These concrete flower
tain a low temperature during distillation and, if neces- oils contain considerable amounts of plant waxes,
sary, to employ high temperatures for as short a time albuminous material, and color pigments, and are only
as possible. Steam distillation may also be modified by partly soluble in alcohol. To obtain alcohol-soluble
changing the pressure in the distilling equipment to products the concrete must be converted into the so-
either reduced or excess pressure. called L'absolute" (19, 20). For this purpose the con-
Expression. Essential oils which are contained in oil crete flower oils are treated several times with warm
sacs in the peels of citrus fruit are obtained by "cold absolute alcohol in which most waxes are not soluble.
pressing" (15, 16). Basically the process of expression The alcoholic extracts are then refrigerated to precipi-
consists of mechanically rupturing these sacs and liher- tate as much as possible of the remaining waxes which
ating the oil, which is collected together with some cell are filtered in the cold. The alcoholic tinctures thus
water and cell debris. The oil then is clarified and sep- obtained often find application in fine perfumes. In
arated by decanting, centrifuging, filtering, etc. most cases, however, the alcohol is distilled off at re-
Depending on the local facilities, the cold pressing is duced pressure, to yield the absolute of the respective
204 / Journol of Chemicol Education
flower oil. The extracted natural flower oils are among "
terpeneless," "terpeneless and sesquiterpeneless oils"
the most highly priced products in the industry. (A (25, $6). These contain mainly the oxygenated com-
pound of absolute of jasmine for example costs up to pounds concentrated from carefully selected pure nat-
$500.) Separating the essential oils from the plant ural oils. They are more stable and stronger in odor
material by the method of cold pressing or extraction and flavor, and are comparatively highly soluble in
permits the operating temperatures to be kept low alcohol; hence they are more useful. Most essential
(under SOT) during most of the processes, thus pro- oils consist of a mixture of hydrocarbons (terpenes,
ducing an oil with a "true to nature" odor and flavor sesquiterpenes, etc.), oxygenated compounds (alcohols,
superior to the steam-distilled oils. esters, ethers, aldehydes, ketones, lactones, phenols,
The yield of essential oil, disregarding the different phenolethers, oxides, etc.) and a small percentage of
methods of isolation, ranges on the average from about viscid or solid non-volatile residues (paraffins, waxes,
O.O1yo to roughly 5y0, by weight, of the aromatic plant and products of resinification). Of these the oxygen-
material. It should also be kept in mind that the qual- ated compounds are the principal odor and flavor car-
ity of the same type of oil may vary greatly, depending riers, although the terpenes and sesquiterpenes con-
011 the availability of equipment and on geographic tribute to some degree to the total odor and flavor char-
location and the climatic and soil conditions in which acter of the oil. The oxygenated substances possess
the aromatic plant grew. the advantage of better solubility in dilute alcohol and
Many natural oils are imported. However, during (with the exception of some aldehydes) of greater sta-
World War I and I1 when most imports were cut off, bility against oxidizing and resinifying influences. The
the United States developed domestic oils ($1). Today terpenes and sesquiterpenes, chemically unsaturated,
this country has become the world's largest producer of oxidize and resinify readily in light and air; odor and
such important essential oils as citms oils from Cali- flavor will be spoiled under improper storage conditions.
fornia and Florida, turpentine, peppermint, spearmint, The "concentrated oils" have only part of the low boiling
dill, cedarwood, and sassafras oils; substantial quan- hydrocarbons removed; this is done by simple frac-
tities of these oils are exported every year. Citrus oils tional distillation in vacuo (1-5 mm pressure). "Ter-
are now by-products in the manufacture of citrus juices peneless oils" are those from which most of the terpenes
(canned, straight, concentrated, frozen, etc.) and the and waxes have been removed by first distilling in vacuo
machinery used in this billion-dollar industry is of the and then extracting with dilute alcohol or other solvents
most modern engineering design. in which the oxygenated compounds are soluble. Some
newer methods of fractionation especially applied to
Synthetic Oils essential oils are countercurrent distribution (87-29)
and a recently reported continuous distillation for fine
Prices of natural essential oils vary greatly, from less separation at low-flow rates (SO). The "terpeneless and
than 91.00 per lb to hundreds of dollars per lb. In sesquiterpeneless oils" have most of the terpenes and
order to get less expensive products, chemists for many the higher boiling fraction of sesquiterpenes as well as
years have endeavored to develop "synthetic" essential waxes removed by a combination of fractionation
oils as substitutes for the natural products. This in vacuo and extraction with dilute alcohol in which
search made great advances particularly during World terpenes, sesquiterpenes and the waxes are almost in-
War I1 when pure essential oils were no longer avail- soluble. The terpeneless and sesquiterpeneless oils
able from the sources abroad. Some of the artificial represent the highest possible concentration of a nat-
oils can be modified in grade and price depending upon ural oil. The degree of concentration is automatically
the intended use. Many low-cost synthetic oils are limited by the amount of oxygenated compounds pres-
used for covering objectionable odors, e.g., of artificial ent in the natural oil: for example, orange oil consists
leather, synthetic rubber, etc. of 2% oxygenated compounds and 98% terpenes, ses-
The artificial oils consist primarily of two groups of quiterpenes and waxes and therefore may be concen-
aromatic chemicals. One group includes those syn- trated fifty times. Bergamot oil, on the other hand,
thesized economically from petroleum or coal tar de- contains 50% hydrocarbons and 50% esters, alcohols,
rivatives plus some synthetics not known in nature. lactones, etc., hence can only be concentrated to double
There is a constant demand and search for new chem- strength. These concentrated oils are more stable and
icals possessing interesting odor and flavor character- soluble, but they do not have the freshness and bouquet
istics (88-$4). The other group, the L'isolates," are of the original natural oil. They are used in many
specific fractions from the distillation of the natural cosmetic preparations and for flavoring, e.g., gelatin
oils containing generally one chemical compound in desserts and candies.
more or less isomeric mixture, e.g., citral from lemon-
grass oil, pinene from turpentine, linalool from hois de Literature Cited
rose oil, geraniol from palmarosa or citronella oil,
citronella1 from citronella oil, safrol from sassafras or (1) GUENTAER, E., "The Essential Oils," Vols. 1-6, D. Van
Nostrand Co., Inc., Princeton, N. J., 1948-52.
camphor oil, eugenol from clove oil. These "isolates" (2) GILDEMEIBTER, E., AND HOFFMANN, F., "Die Atherisehen
may also be used as basic raw material for the manu- Me," Vols. 1-3, 3rd ed., Miltite-Leipzig, 1928-1931.
facture of other aromatic chemicals, e.g., citral con- Also 4th ed., Vols. 1-4, Akademie-Verlag, Berlin, 1956.
verted chemically into ionones, eugenol into vanillin, (3) POUCHER, W. A,, "Perfumes, Cosmetics, and Soaps," Vols.
beta-pineue into geraniol, citronellol, nerol, and lina- 1-3, D. Van Nostrand Go., Inc., Princetan, N. J., 195960.
loo1 ("The Glidden process," $3), etc. (4) BEDOUKIAN, P. Z.,"Perfumery Synthetics and Isolates,"
D. Van Nostrand Co., Inc., Princeton, N. J., 1951.
Another refinement in the manufacture of natural (5) B E D O ~ I AP.N Z.,
, Am. Pmf. Armat., 75 (3) 51 and (4) 49
essential oils is the preparation of "concentrated," (1960), a review of progress in perfumery.

Volume 39, Number 4, April 1962 / 205


(6) SAGABIN, E., "The Science and Art of Perfumery," McGraw- (14) BLOOMFIELD, L. A,, Pevfumew Essent. Oil Record, 27, 404,
Hill Book Go., Inc., New York, 1945. 443, 483 (1936); 28, 24, 59 (1937).
(7) NAVEB, Y. R., AND M A X ~ E G.,
R , "Natural Perfume Mate- (15) GUENTHER, E., "The Essential Oils," Vol. 3, 1949, pp. 6 8 1 .
rids," translated by SAGARIN, E. (from "Les Perfuma (16) GLENN,H. J., & e n . Botany, 1, 415 (1947).
Naturels," Gauthier-Villars, 1939), Reinhold Publishing (17) GUENTBER, E., "The Essential Oils," Vol. 1, 1948, 188-200.
Corp., New York, 1947. s , Perfumery Bssent. Oil Record, 12, 197 (1921).
(18) C r r r ~ ~A.,
(8) GRIBOU,H., Am. P w f . Armat., 75, (6) 87 (1960), history of (19) GUENTHER, E., "The Essential Oils," T'ol. 1, 1948, 200-218.
perfumes. (20) NAYES,Y . R., Riechstoff lnd., 11, 135, 151, 176,212 (1936);
12, 23, 50, 137 (1937).
(9) BROWNE, C. A,, J. CHEM.EDUC.,11,131(1934), essentialoil (21) HALL,M. D., J. CHEM.EDUC.,25, 45 (1948).
industry of foreign lands. (22) HACKFORTH-JONES, J., Am. P q f . Avomat., 7 5 , No. 6, 90
(10) WHITE,L. J., A N D EISERLE,R. L., Ind. and Eng. Chem., 53, (1960).
~ ~~~,
No. 6, 421 (1961). (23) MAX,E., Perfumery Essmt. Oil Record, 51, 541 (1960).
(11) GUENTEER, E., "The Essential Oils," Vol. 6: HAAS,T. P., (24) NATES,Y. R., Bull. Soc. Chim. F~ance,1754 (1959).
"Botanical Classification of Essential Oil Plants," 391 (25) NAVES,Y. R., Mfg. Chemist, 18, No. 4, 173 (1947).
(1952). ., Riv. ital. e s s a z e profumi, 2I
(12) GUENTHER,E., "The Essential Oils," Vol. 1, 1949, p. 104: (27) SORM,F., ETAL., Coll. czeek. chem. Commun., 15,373 (1950).
practice of distillation. (28) MURRAY, J , Perfumery Easent. Oil Record, 43, 148 (1952).
(13) VON RECHENBERG, C., "Einfache und Fraktionierte Destill* . . SUTHERLAND.
(29) M D... Perfumeru
. Essent. Oil Rccord.. 43.. 453
tion in Theorie und Praxis," Schimmel & Co., Miltitz- (1952).
Leipzig, 1923. (30) BAROUT, R., Parfi~msCosmet. Savons, 4, No. 2, 55 (1961).

206 / Journal of Chemical Education

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