222 K. G. D.

FLAVOUR ANDBABU AND V. K. KAUL

FRAGRANCE JOURNAL
Flavour Fragr. J. 2005; 20: 222–231
Published online 20 December 2004 in Wiley InterScience (www.interscience.wiley.com). DOI: 10.1002/ffj.1414

Variation in essential oil composition of rose-scented

geranium (Pelargonium sp.) distilled by different
distillation techniques†
Kiran G. D. Babu and V. K. Kaul*
NPP Division, Institute of Himalayan Bioresource Technology, PO Box 6, Palampur, HP-176 061, India
Received 18 March 2003; Revised 25 November 2003; Accepted 8 December 2003

ABSTRACT: The rose-scented geranium (Pelargonium sp.) cultivar ‘Kelkar’, grown in the agroclimatic conditions of
the western Himalayas, was processed by various hydrodistillation methods, which revealed that water distillation of the
herb gave a higher oil yield (0.16–0.22%) than the water–steam distillation (0.09–0.12%) and steam distillation methods
(0.06–0.18%). The samples were analysed by GC and GC–MS to study and compare the essential oil compositions which
revealed that the oil distilled by the water–steam distillation method contained a higher content of monoterpene hydro-
carbons (1.7%), followed by steam distillation without cohobation and without recycling (1.5%). A higher content of
sesquiterpene hydrocarbons (4.4%) was found in cumulative oil followed by ‘direct oil’ (4.2%) obtained by steam distilla-
tion with cohobation and without recycling of hydrosol, followed by the water–steam distillation method (3.4%). ‘Decanted
oil’, recovered from redistilling the hydrosol obtained by steam distillation with cohobation and without recycling, con-
tained maximum monoterpene cyclic ethers (1.1%) and carbonyl content (9.9%), closely followed by water–steam distilla-
tion method (1.1% and 7.2%, respectively). Steam distillation without cohobation and without recycling of hydrosol yielded
essential oil with a higher percentage of esters (21.1%), followed by ‘direct oil’ (16.6%). Lower ester content (5.3%) was
noticed in ‘decanted oil’, followed by oil distilled by steam distillation with cohobation and with recycling (11.8%) and oil
distilled in a Clevenger apparatus by the water distillation method (12.2%), whereas maximum total alcohols were found in
the ‘decanted oil’ (75.1%), followed by oil from the Clevenger apparatus (72.8%) and steam distillation with cohobation and
with recycling (69.1%). A lower alcohol content was found in the ‘direct oil’ (55.2%) closely followed by ‘cumulative oil’
(55.8%). The variation in total alcohol and ester contents in geranium oil samples, distilled by using different processing
techniques on pilot scale distillation, is mainly due to hydrolysis of some volatile constituents. This was further supported
by acid values of the oils, along with other physicochemical properties, such as specific gravity, optical rotation, refrac-
tive index, solubility in alcohol, ester value with cold and hot methods, estimation of ester content as geranyl formate and
geranyl tiglate, ester number after acetylation, and ester number after formylation with aceto-formic acid and formic
acid. Methods have been standardized and proposed for distillations of specific quality, e.g. ester-rich and alcohol-rich
geranium oils, to meet different requirements of the industry. Copyright © 2004 John Wiley & Sons, Ltd.
KEY WORDS: Pelargonium sp.; Geraniaceae; geranium oil; direct oil; decanted oil; hydrosol; hydrodistillation; steam distil-
lation; physicochemical properties; essential oil composition; quality comparison; cohobation

Introduction been carried out in India, and the literature survey

It is believed that rose-scented geranium (Pelargonium
spp., family Geraniaceae) was introduced in India, in the
beginning of the twentieth century. The three cultivars of
geranium, Algerian, Bourbon and Egyptian, which are
presently being cultivated in India, are hybrids originat-
ing from Pelargonium graveolens, P. radens and P.
capitatum.1 Variation in the essential oil composition
of different genotypes of rose-scented geranium was
reported earlier.2,3 Significant work on geranium oil has
* Correspondence to: V. K. Kaul, Natural Plant Products Division, Institute
of Himalayan Bioresource Technology, PO Box 6, Palampur, HP-176 061,
India.
E-mail: vkaul2002@yahoo.co.in
Contract/grant sponsor: ICEOFF-’89, New Delhi, India; Contract/grant
number: GAP-0024.
† IHBT Communication No. 0302.
revealed that oil composition is influenced by location,4
age of leaves,5 climatic changes,6 drying of herbage prior
to distillation,7–9 comminution,10 cultivars and method of
distillation,11 type of distillation units/apparatus used,12,13
application of growth regulators,14,15 storage of oil,16
weeds,17 little leaf disease,18 semi-arid tropical climate,19
partial shade of trees20 and the plant part distilled.21 Ap-
plication of fertilizers, however, did not alter the com-
position, but increased the essential oil yield by applying
nitrogen.22–25 The essential oil composition of geranium
grown in different countries has been extensively re-
viewed by Lawrence.26 Detailed study of the chiral com-
pounds of geranium oils was carried out by Doimo
et al.27 Variation in quality of geranium oil due to use of
different materials for the construction of distillation units
was also investigated by the same authors.28 Large vari-
ations in citronellol content was noticed in oil distilled

Copyright © 2004 John Wiley & Sons, Ltd. Flavour Fragr. J. 2005; 20: 222–231
 ESSENTIAL OIL OF PELARGONIUM SP. FROM DIFFERENT DISTILLATIONS 223
from the material propagated by tissue culture and
cuttings.29 The variation in citronellol:geraniol (C:G) ratio
with respect to air temperature prior to harvesting was
closely monitored by Doimo et al.30 Being stable in an
alkaline medium, geranium oil is ideally suited for the
scenting of soaps. The oil has a strong, pleasant odour,
described as rosy with a mint top note, and finds
extensive application in perfumery, cosmetics, flavour
industries, aromatherapy and for commercial extraction
of ‘rhodinol’. Rhodinol is a high-value aroma chemical
used widely in fine grade perfumes. The market value of
geranium oil is determined by its citronellol content.
On a commercial scale, the most widely used eco-
nomical method for the separation of volatile oil from
the plant matrix is hydrodistillation. Production methods
for essential oils are best discussed by Denny31 and
Lawrence.32 There are three methods of hydrodistillation:
(a) water distillation (herbage totally immersed in water);
(b) water–steam distillation (plant material loaded on a
perforated grid or false bottom placed above the actual
bottom of the distillation tank and water is filled to a
level somewhat below this grid); (c) steam distillation
(direct steam is injected in the distillation tank and the
herbage is loaded over the grid). Theoretically, there is
no fundamental difference between these three methods.
However, there are certain variations in practice and
in the practical results obtained, which in some cases
are considerable; they depend on the distillation method
employed because of certain reactions occurring during
distillation which are reported in the present investigation.
During hydrodistillation, esters present in essential oils
are generally hydrolysed by the release of H+ ions from
water. In the presence of water at around 100 °C, esters
hydrolyse to the corresponding acids and alcohols:
corresponding acids
Esters + water
and alcohols
Two characteristic features are important in deter-
mining the effect of these reactions during distillation. In
the first place, the reactions are not complete in either
direction. Starting with the ester and hot water, only a
part of the ester reacts and, when equilibrium is reached,
the esters, water, alcohols and acids are found to be
present in the distillation tank. Similarly, if only alcohols
and acids are present at the start, all the four constituents
are present when equilibrium is established. A second
important characteristic of the hydrolysis reaction in the
distillation of essential oils is that hydrolysis proceeds at
a measurable rate. The fact that these reactions are not
infinitely rapid and the extent to which they proceed
depend on time of contact between oil and water; this
holds true for short periods of contact. This is another
obvious disadvantage of water distillation, since the oil
and water have a maximum time of contact under the
Copyright © 2004 John Wiley & Sons, Ltd.
conditions employed. These characteristic features have
been discussed, in the present communication, with
supporting data such as GC and GC–MS analysis and
physicochemical properties (acid and ester values, includ-
ing total alcohol content). The equilibrium constant, K,
for the same can be calculated as:
[alcohol] × [acid ]
K =
[ester] × [water]
where [alcohol] = concentration of alcohols, [acid] =
concentration of acids, [ester] = concentration of esters
and [water] = concentration of water.
Esters are formed from four major alcohols, viz. citro-
nellol, nerol, geraniol and 2-phenylethanol and from the
carboxylic acids found in geranium. Higher chain esters
have been reported to be present as 2- and 3-methyl
butyrate branched esters.26(a) A detailed report on straight
and branched esters in Australian geranium oils was first
given by Doimo et al.33 Citronellic acid as the major
constituent (27.9–89.3%) in the geranium oil was re-
ported by Lis-Balchin.34 The qualitative and quantitative
characteristics of volatile oils are greatly influenced by
the type of planting material (dried or fresh), distillation
technique adopted and other factors such as the degree
of comminution of plant material, weight of material
charged, distillation time, pressure or vacuum applied,
amount of steam injected, treatment/redistillation of the
hydrosol, whether the ‘decanted oil’ (redistilled from the
hydrosol) is added to the ‘direct oil’ or not. The effects
of water distillation and steam distillation differ con-
siderably. High-boiling constituents of the volatile oil
are generally lost during water distillation if the plant
material is not fully comminuted. Oil constituents that are
slightly soluble in water (such as phenols, certain alcohols
and acids) are retained in the still, with the result that
water distillation produces a different oil than that pro-
duced by steam distillation.
Kaul et al.11 distilled geranium plant material by two
methods, water distillation and steam distillation, to com-
pare the composition of volatile oil. The other method,
i.e. water–steam distillation, which is expected to produce
higher oil yields than steam distillation and a better
quality of oil than water distillation due to least hydro-
lysis, has been discussed in the present communication.
It is well known that hydrolysis of the esters—and more
precisely the formates—does takes place in hydrodistilla-
tion technique. In the present scenario of the essential oil
industry, geranium oil is being distilled conventionally
by: (a) water–steam distillation without cohobation and
without recycling of hydrosol simultaneously; (b) steam
distillation with/without cohobation and without recycling
of hydrosol simultaneously. In the present investigation,
geranium oil was distilled by three methods of hydro-
distillation with a combination of cohobation and recycl-
ing, for comparison of oil quality and to study the extent
Flavour Fragr. J. 2005; 20: 222–231
224 K. G. D. BABU AND V. K. KAUL
of ester hydrolysis taking place during distillation in
commercial-scale processing units.
Experimental
Plant Materials
Rose-scented geranium (Pelargonium sp.), cultivar
‘Kelkar’, was introduced during 1999 and domesticated
under Palampur agroclimatic conditions at an elevation
of 1475 m above sea level (32°06′40″N latitude and
76°33′46″E longitude) in the mid-hills of the western
Himalayas. Healthy, vigorously growing biomass of
1 year-old plants was harvested (250–350 mm from top)
during May–June, shade-dried for 12 h and then used for
essential oil distillation by different methodologies.
Methods of Hydrodistillation
Distillation in a Clevenger apparatus
2 kg geranium leaves was charged in Clevenger apparatus
along with 4 l water (pH 6.6–6.8). The distillation was
continued for 3 h to isolate the oil. The process may be
treated as a water distillation method, since the material
is (partially) immersed in the water. The oil distilled was
dried over anhydrous sodium sulphate and used for ana-
lysis. This sample was considered as the reference oil for
quality comparison.
Water distillation (on pilot plant)
40 kg herbage was loaded in a distillation tank, immersed
in water and heated by direct firing. The vapours formed
were cohobated in a cohobation column and then con-
densed in a 1-1 shell and tube heat exchanger. The
distillate was collected in a receiver/separator. The dis-
tillate was recycled, simultaneously, in the still through
the cohobation column from the separator. The accumul-
ated oil in the receiver was separated and dried over
anhydrous sodium sulphate and analysed.
Water–steam distillation (on pilot plant)
Geranium plant material was charged on a perforated
grid/false bottom in a direct-fired field distillation unit
fitted with a cohobation column, horizontal 1-1 shell and
tube heat exchanger and a receiver/separator. 40 kg plant
material/batch was charged in the still, along with 50 l
fresh water, and the water level was kept at 50 mm
below the false bottom. The distillation tank was heated
by fuel wood and coal. After 1.5 h, the first drop of dis-
tillate was collected in the receiver. The geranium oil
started collecting in the separator and the hydrosol was
Copyright © 2004 John Wiley & Sons, Ltd.
recycled to the distillation tank through the cohobation
column, where the vapours arising from the distillation
still were allowed to flow in the counter-current direction,
with the down-flowing stream of distillate, to enrich
vapour with oil. During vapour contact with liquid phase,
the vapour absorbs soluble oil from the water stream,
thereby recovering the oil to some extent. The process
was continued for 7 h to recover the soluble oil. The oil
collected was measured, dried over anhydrous sodium
sulphate and analysed.
Steam distillation (on pilot plant)
Without cohobation and without recycling of hydrosol.
50 kg geranium leaves were loaded on a false bottom
of the distillation tank. The tank was connected directly
to a vertical 1-1 shell and tube heat exchanger. Steam,
generated in the boiler, was fed to the tank to commence
distillation. After 15 min, the first drop of condensate was
collected and the distillation process continued for 7 h to
recover the total geranium oil. The distillate collected in
the receiver/separator was not recycled in the still. The
oil separated from the distillate was measured, dried over
anhydrous sodium sulphate and analysed.
With cohobation and without recycling of hydrosol.
350 kg geranium plant material was charged over a false
bottom in a distillation tank having a cohobation head
column, and steam was injected to commence distillation.
After 45 min, the first drop of condensate was collected.
The vapours were passed through a cohobation column
and condensed in 1-1 shell and tube heat exchanger and
collected in a receiver. The oil was separated from the
distillate in a separator and designated ‘direct oil’. The
process was continued for 8 h. The distillate collected
from four batches was pooled and charged in another
tank, where it was heated by an external steam jacket for
6 h to recover water-soluble oil by redistillation, which
is designated ‘decanted oil’. The direct and decanted oils
were mixed to form commercial grade oil, which is
designated ‘cumulative oil’.
With cohobation and with recycling of hydrosol. 350 kg
geranium leaves were charged on a false bottom in the
distillation tank and steam was spurged at the bottom of
the false bottom to commence distillation. The vapours
formed were cohobated in a cohobation column and then
condensed in a horizontal shell and tube heat exchanger.
The distillate and the oil collected were separated in
a receiver/separator. The distillate was simultaneously
recycled to the distillation tank through the cohobation
column from the receiver/separator. After completion of
4 h distillation, steam was also injected into the steam
jacket to boil the residual water being collected at the
bottom of the still, and the process was continued for
another 4 h. The oil collected at the end of the process
Flavour Fragr. J. 2005; 20: 222–231
 ESSENTIAL OIL OF PELARGONIUM SP. FROM DIFFERENT DISTILLATIONS 225
Table 1. Variation in geranium oil yields produced by different methods of hydrodistillation
Sl. No. Method/type of distillation
Laboratory scale
1.Clevenger-type apparatus
Pilot scale
2.Water distillation
3.Water–steam distillation
4.Steam distillation
(i) Without cohobation and without recycling (‘direct oil’ only)
(ii) With cohobation and without recycling (including ‘direct oil’ and ‘decanted oil’)
(iii) With cohobation and with recycling
was measured, dried over anhydrous sodium sulphate and
analysed.
Four replicates of oil samples from each hydrodistilla-
tion method were distilled and the ranges of oil yields are
given in Table 1. Samples were analysed by GC–FID and
the average chemical compositions of the oil, along with
their standard deviations, are given in Table 2. Geranium
oil samples produced by the above distillation methods
were analysed for their physicochemical properties by the
established procedures mentioned in the literature35,36 and
the results are presented in Table 3.
Analysis
GC analysis of essential oil samples was performed
on Shimadzu Gas Chromatograph GC-14B fitted with
carbowax 20 M capillary column (60 m × 0.25 mm i.d.,
film thickness 0.25 µm), using nitrogen as auxiliary car-
rier gas at a flow rate 4 ml/min, equipped with FID and
C-R7A chromatopack data processing system. Temper-
ature programme: 40–190 °C at a rate of 10 °C/min, with
a 2 min hold at 40 °C and 15 min at 190 °C. Injector
and detector temperatures were kept at 250 °C and
230 °C, respectively.
GC–MS analysis was conducted on Perkin-Elmer
Model 910 gas chromatograph equipped with a carbowax
20 M Supelco capillary column (60 m × 0.25 mm i.d.,
film thickness 0.25 µm), using the same temperature con-
ditions as in GC. Helium was used as the carrier gas,
with a head pressure of 18 psi. Identification of constitu-
ents was carried out by comparison of mass spectra with
the data given in literature,37–39 NIST library,40 our own
created library and also by comparison of RI data.
Results and Discussion
The minimum and maximum essential oil yields (% v/w)
in a Clevenger apparatus produced by the water distilla-
tion method were 0.18% and 0.22%, respectively. This
oil yield range is always higher than that observed on the
pilot scale in each method of distillation followed. How-
ever, among the methods used on the pilot scale, water
Copyright © 2004 John Wiley & Sons, Ltd.
Range of oil yield (% v/w)
0.18 – 0.22
0.16 – 0.19
0.09 – 0.12
0.06 – 0.10
0.07– 0.11
0.14 – 0.18
distillation produced higher oil yield (0.16–0.19%), fol-
lowed by steam distillation with cohobation and recycling
(0.14–0.18%) and water–steam distillation (0.09–0.12%).
The lowest oil yields were observed in steam distillation
without cohobation and without recycling of hydrosol
(0.06–0.10%), followed by steam distillation with
cohobation and without recycling of hydrosol (0.07–
0.11%), which includes the direct and decanted oils.
Agglutination and lump formation of plant material was
observed in the distillation tank when the material was
distilled by steam distillation with and without cohobation
and without recycling and by water–steam distillation
methods. This can be attributed to the small quantity of
water present in the still. Compared with water distilla-
tion method, the above-mentioned three distillation
techniques produced lower oil yields, as lumping of the
charged material prevents a uniform flow of steam
through the plant material and results in channelling of
steam, leading to incomplete distillation.
Some of the chemical constituents, viz. trans-2-
hexenal, α-terpinene, terpinolene, α-ylangene, α-copaene,
etc., which have been reported previously,11 could not
be detected under these experimental conditions. The
major constituents, viz. citronellol, geraniol, linalool,
isomenthone, citronellyl formate, geranyl formate and
10-epi-γ -eudesmol, and minor constituents, viz. cis- and
trans-rose oxides, α-terpineol, geranyl acetate, citronellyl
butyrate, geranyl butyrate, guaia-6,9-diene, germacrene D,
2-phenylethyl tiglate and geranyl tiglate, etc., are present
in all the samples.
Geranium oil produced in a Clevenger-type apparatus
by the water distillation method was found to be rich
in geraniol (22.12%) and citronellyl tiglate (0.84%). The
oil produced on a pilot scale by the water distillation
method contained higher percentages of cis-3-hexenol
(0.37%), nerol (0.82%). Samples produced by the water–
steam distillation method were rich in α-pinene (0.33%),
sabinene (0.20%), myrcene (0.22%), cis-rose oxide
(0.44%) and geranial (0.52%). Two constituents, p-
cymene and neryl formate, were found in traces. Samples
produced by the steam distillation method without
cohobation and without recycling of hydrosol contained
higher amounts of α-phellandrene (0.11%), (Z)-β -ocimene
(0.30%), (E)-β -ocimene (0.34%), citronellyl formate
Flavour Fragr. J. 2005; 20: 222–231
 Table 2. Comparative average# chemical composition (%) of geranium oils produced by different hydrodistillation methods
Copyright © 2004 John Wiley & Sons, Ltd.

226
K. G. D. BABU AND V. K. KAUL
Constituents RI Laboratory scale Pilot plant

Clevenger Water Water–steam Steam distillation

apparatus distillation distillation
Without With cohobation and without recycling With cohobation
cohobation and of hydrosol and with recycling
without recycling of hydrosol
of hydrosol ‘Direct oil’ ‘Decanted oil’ ‘Cumulative oil’

α -Pinene 1039 tr tr 0.33 (0.13) 0.25 (0.15) 0.22 (0.13) tr 0.22 (0.17) tr
Sabinene 1130 — — 0.20 (0.14) 0.19 (0.09) 0.17 (0.07) 0.15 (0.19) 0.18 (0.05) —
Myrcene 1156 tr tr 0.22 (0.14) tr 0.16 (0.14) tr 0.10 (0.12) tr
α -Phellandrene 1178 tr tr 0.10 (0.13) 0.11 (0.10) tr tr tr tr
Limonene 1190 tr — 0.27 (0.03) 0.23 (0.02) 0.28 (0.17) 0.14 (0.11) tr —
(Z)-β -Ocimene 1238 tr tr 0.20 (0.16) 0.30 (0.12) 0.18 (0.11) 0.16 (0.15) 0.26 (0.07) tr
(E)-β -Ocimene 1257 tr tr 0.26 (0.10) 0.34 (0.18) 0.29 (0.07) 0.29 (0.05) tr tr
p-Cymene 1268 tr — tr tr tr 0.10 (0.04) tr —
cis-3-Hexenol 1351 0.35 (0.12) 0.37 (0.17) 0.22 (0.19) tr tr 0.19 (0.15) 0.27 (0.16) 0.10 (0.14)
cis-Rose oxide 1354 0.21 (0.22) 0.37 (0.26) 0.44 (0.17) 0.28 (0.11) tr 0.18 (0.12) 0.26 (0.17) 0.12 (0.29)
trans-Rose oxide 1370 tr 0.11 (0.28) 0.14 (0.18) tr 0.28 (0.15) 0.25 (0.13) tr tr
cis-Linalool oxide (furanoid) 1423 tr 0.14 (0.19) 0.21 (0.13) tr 0.15 (0.07) 0.29 (0.15) 0.32 (0.04) tr
Menthone 1444 0.24 (0.12) 0.27 (0.21) 0.33 (0.19) — 0.69 (0.03) 0.75 (0.09) tr —
trans-Linalool oxide (furanoid) 1451 tr 0.27 (0.09) 0.26 (0.06) tr tr 0.36 (0.06) tr tr
Isomenthone 1528 4.25 (1.26) 6.20 (1.02) 6.33 (1.22) 5.77 (2.01) 6.05 (2.45) 8.72 (2.33) 6.28 (2.07) 1.62 (3.94)
Linalool 1544 8.92 (2.51) 14.38 (1.09) 13.63 (1.19) 11.87 (1.10) 8.90 (1.01) 15.89 (2.02) 9.22 (1.22) 4.84 (3.54)
β -Bourbonene 1586 0.22 (0.75) 0.12 (0.18) 0.71 (0.70) 0.82 (0.97) 1.32 (0.77) 0.22 (0.10) 0.41 (0.03) 0.23 (0.29)
Citronellyl formate 1600 5.27 (1.19) 5.02 (0.32) 5.50 (1.88) 8.57 (1.00) 7.29 (0.91) 1.83 (0.44) 8.04 (0.51) 2.29 (0.37)
β -Caryophyllene 1602 0.23 (0.28) — 0.66 (0.99) 0.62 (0.81) 1.06 (0.82) 0.15 (0.04) 0.34 (0.29) tr
Citronellyl acetate 1645 tr — — 0.59 (0.06) 0.35 (0.27) 0.11 (0.09) 0.16 (0.27) 0.13 (0.04)
Neryl formate 1663 tr tr tr 0.34 (0.18) tr tr 0.32 (0.02) tr
α -Humulene 1672 tr 0.18 (0.27) 0.26 (0.22) 0.14 (0.19) 0.31 (0.27) 0.22 (0.01) 0.18 (0.29) tr
Geranyl formate 1684 2.38 (0.16) 4.23 (0.55) 2.91 (0.91) 6.32 (1.28) 1.95 (2.99) 0.36 (0.93) 0.68 (0.84) 0.88 (1.19)
Citronellyl propionate 1700 tr 0.17 (0.23) 0.15 (0.14) 0.20 (0.56) 0.20 (0.49) 0.15 (0.10) 0.19 (0.17) 0.93 (0.31)
α -Terpineol 1706 — 2.09 (0.91) 1.99 (0.99) 1.22 (1.01) 2.07 (1.05) 3.71 (1.11) 2.23 (2.03) —
Germacrene D 1712 tr 2.08 (0.09) 1.31 (0.77) 0.20 (1.00) 1.31 (0.23) 1.27 (0.93) 2.36 (0.12) tr
Citronellol 1722 36.79 (2.32) 22.93 (0.47) 24.95 (3.21) 23.14 (2.98) 30.23 (2.81) 40.19 (4.91) 29.66 (2.36) 36.48 (2.95)
Geranial 1730 — — 0.52 (0.14) — 0.26 (0.22) 0.38 (0.17) 0.41 (0.31) —
Geranyl acetate 1735 0.29 (0.09) 1.29 (1.16) 0.68 (0.29) 1.24 (0.94) 0.89 (1.33) 0.23 (0.31) 1.89 (0.92) 0.30 (0.94)
Piperitone 1748 — — — — 0.14 (0.10) — 0.42 (0.17) —
Nerol 1757 0.51 (0.22) 0.82 (0.26) 0.30 (0.13) 0.64 (0.33) 0.14 (0.15) 0.25 (0.26) 0.55 (0.15) 0.30 (0.25)
Citronellyl butyrate 1786 0.14 (0.01) 0.28 (0.09) 0.12 (0.17) 0.41 (0.99) 1.19 (0.52) 0.26 (0.74) 0.35 (0.29) 0.32 (0.11)
Geraniol 1798 22.12 (2.36) 20.56 (0.14) 19.25 (2.11) 20.74 (2.01) 8.21 (1.91) 11.55 (1.17) 7.95 (1.55) 17.97 (2.54)
Geranyl-n-propionate 1799 0.20 (0.04) — 0.27 (0.13) 0.41 (0.27) 0.50 (0.11) 0.33 (0.07) 0.30 (0.01) 0.20 (0.14)
Guaia-6,9-diene 0.50 (0.01) — 0.41 (0.03) — 0.22 (0.91) tr 1.10 (0.16) 0.23 (0.21)
Geranyl-n-butyrate 1872 0.11 (0.21) 0.14 (0.09) 0.25 (0.15) 0.12 (0.07) 0.29 (0.02) 0.22 (0.11) 0.19 (0.06) 0.22 (0.05)
Geranyl tiglate 1985 2.06 (0.45) 1.87 (0.67) 1.95 (0.94) 1.87 (0.59) 2.40 (1.62) 0.96 (0.43) 1.87 (0.72) 4.79 (1.07)
Flavour Fragr. J. 2005; 20: 222–231

Citronellyl tiglate 1991 0.84 (0.60) 0.77 (0.15) 0.45 (0.18) 0.21 (0.15) 0.45 (0.24) 0.16 (0.03) 0.46 (0.27) 0.39 (0.29)
10-epi-γ -Eudesmol 2121 4.13 (2.31) 5.05 (1.55) 4.93 (2.11) 4.97 (1.97) 5.59 (0.91) 3.34 (0.59) 5.90 (0.36) 9.36 (1.01)
2-Phenylethyl tiglate 2154 0.78 (0.25) 0.72 (0.18) 0.77 (1.02) 0.82 (1.41) 0.99 (1.52) 0.70 (0.17) 0.92 (0.99) 1.23 (0.02)
Monoterpene hydrocarbons* 0.38 0.31 1.66 1.45 1.36 0.89 0.79 0.34
Carbonyls* 4.49 6.47 7.18 5.77 7.14 9.85 7.11 1.62
Monoterpene cyclic ether* 0.43 0.89 1.05 0.31 0.45 1.08 0.60 0.34
Esters* 12.19 14.51 13.08 21.10 16.58 5.32 15.37 11.77
Alcohols* 72.82 66.20 65.27 62.62 55.15 75.12 55.78 69.05
Sesquiterpene hydrocarbons* 1.07 2.38 3.35 1.78 4.22 1.88 4.39 0.64

#
Average reading of four replicate samples.
RI, retention indices on carbowax 20 M capillary column.
The data mentioned in the parenthesis are corresponding standard deviation (±) of the reading.
—, absent; tr, traces (<0.10%).
* Including traces.
Copyright © 2004 John Wiley & Sons, Ltd.

Table 3. Physicochemical properties of geranium oils produced by different hydrodistillation methods

Physicochemical Laboratory scale Pilot plant

properties
Clevenger Water Water–steam Steam distillation
apparatus distillation distillation
Without With cohobation and without With
cohobation recycling of hydrosol cohobation
and without and with
recycling of ‘Direct oil’ ‘Decanted oil’ ‘Cumulative oil’ recycling of
hydrosol hydrosol
20
Specific gravity, d 20 0.9124 0.9012 0.8971 0.8969 0.8944 0.9685 0.9045 0.8999
Optical rotation, α20
D [−] 9°49′ [−] 9°37′ [−] 10°46′ [−] 11°5′ [−] 12°4′ [−] 9°15′ [−] 11°33′ [−] 10°1′
Refractive index, [n] D20 1.4749 1.4772 1.4714 1.4712 1.4710 1.4785 1.4755 1.4722
Solubility in 70% alcohol 1:1 to 1.5 vol. 1:0.5 to 1.0 vol. 1:1 to 2 vol. 1:2 to 2.5 vol. 1:3.5 to 4 vol. 1:0.5 vol. 1:1 to 2 vol. 1:1 vol.
Acid value 9.81 9.98 9.43 7.06 7.04 11.72 8.58 9.89
Ester value

ESSENTIAL OIL OF PELARGONIUM SP. FROM DIFFERENT DISTILLATIONS 227

By cold method 19.42 21.95 21.38 34.45 29.27 15.96 21.91 20.13
By hot method 42.51 39.92 51.39 52.37 58.69 13.15 45.17 41.34
Ester content as geranyl formate 6.31 7.13 6.95 11.19 9.51 5.19 7.12 6.54
Ester content as geranyl tiglate 17.91 16.81 21.65 22.07 27.73 5.54 19.03 17.42
Ester number after acetylation with acetic anhydride
By cold method 22.15 20.12 31.61 43.93 44.78 10.89 33.37 19.15
By hot method 134.58 102.54 111.32 196.64 200.07 168.82 194.99 112.35
Ester content as geranyl formate 7.20 6.54 10.27 14.27 14.46 3.54 10.84 6.22
Ester content as geranyl tiglate 56.69 43.19 80.59 82.83 84.28 71.12 82.14 47.33
Total alcohols as geraniol
By cold method 6.19 5.55 8.71 12.41 12.34 2.99 9.19 5.28
By hot method 36.73 28.05 50.80 21.07 53.03 45.05 51.74 30.71
Ester number after acetylation with aceto-formic acid
By cold method 210.35 240.17 225.63 225.86 209.03 252.04 214.72 204.53
By hot method 229.55 255.13 239.62 249.84 225.71 249.89 233.23 217.81
Total alcohol as linalool
By cold method 58.60 67.06 62.94 62.99 58.23 70.44 59.84 56.96
By hot method 64.04 71.32 66.90 69.81 62.95 69.83 65.08 60.71
Flavour Fragr. J. 2005; 20: 222–231

Ester number after formylation with formic acid

By cold method 129.16 92.53 103.59 105.37 131.19 136.97 94.23 126.58
By hot method 135.11 101.79 118.46 116.47 142.45 146.18 114.67 133.99
Ester content as citronellyl formate
By cold method 42.42 30.39 34.02 34.61 43.09 39.75 30.95 41.57
By hot method 44.38 33.43 38.81 38.26 46.79 48.01 37.66 44.01
Total alcohols as citronellol
By cold method 38.46 27.02 28.23 28.71 35.53 37.50 25.73 37.63
By hot method 40.37 29.87 32.10 31.65 38.48 39.45 31.17 39.99
228 K. G. D. BABU AND V. K. KAUL
(8.57%), neryl formate (0.34%), geranyl formate (6.32%)
and citronellyl acetate (0.59%). Myrcene, p-cymene, cis-
3-hexenol, trans-rose oxide, cis- and trans-linaloöl oxide
were detected in traces. ‘Direct oil’ produced by the
steam distillation method with cohobation and without
recycling of hydrosol contained higher percentages of
limonene (0.28%), trans-rose oxide (0.28%), citronellyl
butyrate (1.19%), geranyl butyrate (0.29%), β-bourbonene
(1.32%), β-caryophyllene (1.06%), α-humulene (0.31%),
geranyl-n-propionate (0.5%). α -Phellandrene, cis-3-
hexenol, p-cymene, trans-linaloöl oxide, cis-rose oxide
and neryl formate were found in traces. ‘Decanted oil’
contained higher percentages of p-cymene (0.1%), trans-
linalool oxide (0.36%), linalool (15.89%), menthone
(0.75%), isomenthone (8.72%), α-terpineol (3.71%) and
citronellol (40.19%), while that of α-pinene, myrcene,
α-phellandrene, neryl formate and 6,9-guaiadiene are
present as traces. The ‘cumulative oil’ consisted of
higher amounts of cis-linalool oxide (0.32%), piperitone
(0.42%), geranyl acetate (1.89%), guaia-6,9-diene (1.1%),
germacrene D (2.36%) and trace amounts of α-
phellandrene, p-cymene, limonene, (E)-β -ocimene, trans-
linalool oxide, trans-rose oxide and menthone. Geranium
oil produced by steam distillation with cohobation and
with recycling of hydrosol is rich in citronellyl pro-
pionate (0.93%), 2-phenylethyl tiglate (1.23%), 10-epi-γ -
eudesmol (9.36%) and geranyl tiglate (4.79%). The volatile
constituents in the category of monoterpene hydrocar-
bons, viz. α-pinene, sabinene, myrcene, α-phellandrene,
p-cymene, limonene and (Z)- and (E)-β -ocimene are
either absent or are present only in traces in the oil
samples produced by water distillation and by steam dis-
tillation with cohobation and with recycling of hydrosol.
Neryl formate was found in traces in all the samples
except in the oil from steam distillation method without
cohobation and without recycling (0.34%) and in ‘cumu-
lative oil’ (0.32%). Steam distilled geranium oil without
cohobation column and without recycling and ‘direct oil’
from steam distillation with cohobation and without recy-
cling of hydrosol contained cis-3-hexenol only in traces.
However, it was found that the same constituent was rich
in oils distilled by the water distillation method on the
laboratory scale (0.35%) and on the pilot scale (0.37%).
This finding is also in agreement with the earlier report
by Kaul et al.11
There is much variation in the quality of the oils
distilled on pilot scale using different hydrodistillation
methods. The highest monoterpene content was observed
in oil obtained by water–steam distillation (1.66%), fol-
lowed closely by steam distillation without cohobation
and without recycling (1.45%) and ‘direct oil’ (1.36%)
distilled from steam distillation with cohobation and with-
out recycling. The lowest monoterpene content was
observed in the oil produced by the water distillation
method (0.31%), followed closely by steam distillation
with cohobation and recycling (0.34%) and Clevenger
Copyright © 2004 John Wiley & Sons, Ltd.
apparatus (0.38%). The highest monoterpene cyclic ether
content was found in the ‘decanted oil’ (1.08%), followed
closely by water–steam distillation (1.05%) and water
distillation method (0.89%). ‘Decanted oil’ consisted of
high carbonyl content (9.85%) followed by water–steam
distillation method (7.18%). The lowest carbonyl content
was noticed in the oil distilled by steam distillation
with cohobation and with recycling (1.62%). The same
sample was also found to contain the lowest content
of sesquiterpene hydrocarbons (0.64%), followed by oil
distilled on laboratory scale in a Clevenger apparatus
(1.07%). In contrast, ‘cumulative oil’ is found to be rich
in total sesquiterpene content (4.39%), followed by ‘direct
oil’ (4.22%) water–steam distillation method (3.35%) and
the water distillation method (2.38%).
It was also observed that maximum content of total
alcohols was present in ‘decanted oil’ (75.12%) recovered
by redistilling the hydrosol from steam distillation with
cohobation and without recycling. This could be due to
the tendency of solubility of alcohols in aqueous medium.
A similar observation, in rose oil distillation, was also
reported in an earlier communication.41 Out of (75.12%)
total alcohols, citronellol (40.19%) was found to be the
major constituent, followed by linalool (15.89%) and
geraniol (11.55%). These three constituents play a major
role in the quality profile of geranium oil and its market
value is determined by the level of citronellol content.
The lowest quantity of alcohols (55.15%) was present in
‘direct oil’ distilled by the steam distillation method with
cohobation and without recycling of hydrosol. However,
amongst the geranium oils distilled directly from the
plant material, Clevenger apparatus contained maximum
total alcohol content (72.82%), followed by steam dis-
tillation with cohobation and with recycling (69.05%) and
water distillation method (66.2%). This variation in the
alcohol content can be explained by the variable amount
of water present in the distillation tank while following
different distillation techniques, and subsequent hydro-
lysis occurred during the distillation process. Variation in
citronellol and geraniol contents can be explained by the
hydrolysis of their respective esters. However, in the case
of linalool, its variation can be ascribed to the fact that
catabolism become apparent during prevailing transient
weather conditions42 and its new synthesis in young and
expanding leaves,6 but is not due to the hydrolysis of
corresponding esters of linalool, as these are absent in
geranium oil. However, studies are required to obtain
further insight into these phenomena. In contrast, a low
quantity of esters (5.32%) was found in the ‘decanted
oil’ distilled from geranium water. Amongst the oils
extracted directly from plant material, the samples pro-
duced by the steam distillation method with cohoba-
tion and with recycling contained a lower ester content
(11.77%), followed by Clevenger apparatus (12.19%).
The highest percentage of esters was observed in oil
produced by the steam distillation method without
Flavour Fragr. J. 2005; 20: 222–231
 ESSENTIAL OIL OF PELARGONIUM SP. FROM DIFFERENT DISTILLATIONS 229
cohobation and without recycling of hydrosol (21.1%),
followed by ‘direct oil’ (16.58%) and ‘cumulative oil’
(15.37%). Hence, it can be concluded that the more
water present in the distillation tank, the more hydrolysis
of esters takes place, thereby increasing the total alcohol
content in the oil. Similarly, if the amount of water in the
still is less, the geranium oil produced will be richer in
ester content and poorer in alcohol content. These results
were further substantiated and authenticated by evaluation
of physicochemical data of different samples, as given in
Table 3.
Specific gravities of the oil samples were determined
at 20 °C and it was found that the ‘decanted oil’ has
maximum value (0.9685), followed by oil distilled in
Clevenger apparatus (0.9124) and ‘cumulative oil’
(0.9045). The lowest specific gravities were observed in
‘direct oil’ (0.8944), closely followed by steam dis-
tillation without cohobation and without recycling of
hydrosol (0.8969), and water–steam distillation method
(0.8971). The samples were tested for optical rotation
at 20 °C (α 20 D ) and all were found to be laevo-rotatory.
‘Direct oil’ (−12°4′) has a higher value of optical rotation
than ‘cumulative oil’ (−11°33′), followed closely by the
oil produced by steam distillation without cohobation
and without recycling of hydrosol (−11°5′). ‘Decanted
oil’ (−9°15′) has the lowest optical rotation compared
with oil distilled by water distillation (−9°37′) and
Clevenger apparatus (−9°49′).
Refractive indices of geranium oil samples were deter-
mined on an Abbé refractometer at 20 °C and it was
found that the ‘decanted oil’ possessed a higher refractive
index (1.4785) than the rest of the samples. ‘Direct oil’
has the lowest refractive index (1.4710), followed by oil
produced by steam distillation without cohobation and
without recycling of hydrosol (1.4712) and water–steam
distillation (1.4714). Solubility of the oils was tested in
70% alcohol at 20 °C. ‘Direct oil’ is clearly soluble in
3.5–4 volumes of 70% alcohol; opalescent with more, up
to 10 volumes; oily separation is observed after 24 h.
Another same category of the oils distilled by steam dis-
tillation without cohobation and without recycling of
hydrosol was clearly soluble in 2–2.5 volumes of 70%
alcohol and more, up to 6.0 volumes; opalescent in
6.2 volumes and more, up to 10 volumes. Oil produced
by the water–steam distillation method was clearly
soluble in 1–2 volumes of 70% alcohol at 20 °C. During
experimentation, the same sample was tested for solu-
bility at 15 °C and it was found that the oil was clearly
soluble after adding 2.5–3.0 volumes and more, up to
4.5 volumes of 70% alcohol. But at 22 °C the same oil
was clearly soluble in 1 volume of 70% alcohol, and oily
separation was observed after 12 h. ‘Decanted oil’ was
clearly soluble only in 0.5 volumes of 70% alcohol and
more, up to 10 volumes. ‘Cumulative oil’ was clearly
soluble in 1–2 volumes of 70% alcohol, and oil produced
by steam distillation with cohobation and with recycling
Copyright © 2004 John Wiley & Sons, Ltd.
of hydrosol was also clearly soluble in 1 volume of 70%
alcohol.
Lowest acid values were noticed in ‘direct oil’ (7.04),
followed by steam-distilled oil without cohobation and
without recycling of hydrosol (7.06) and ‘cumulative
oil’ (8.58). Medium acid values (9.43) were observed
in the oil produced by the water–steam distillation
method. Oils produced by water distillation methods
at the pilot and laboratory scales possessed slightly
higher acid values (9.98 and 9.81, respectively). The
highest acid value (11.72) was observed in ‘decanted
oil’. Ester values were determined by saponification with
cold and hot methods to evaluate the amount of ‘actual
formate’ and ‘actual tiglate’. Ester content as geranyl
formate and geranyl tiglate was calculated, and a large
variation was found between the two, except in ‘decanted
oil’, as the solubility of tiglates in the hydrosol is very
low. Ester number after acetylation with acetic anhydride
and aceto-formic acid was estimated and the total alcohols
were also calculated ‘as geraniol’ and ‘as linalool’,
respectively. Ester number after formylation with 98%
formic acid was also estimated by saponification with
cold and hot methods. The results are given in Table 3.
Processes such as oxidation of aldehydes, hydrolysis
of esters and the often long period of storage of the oil
increase the acid number. However, in the present invest-
igation, oil samples were immediately and thoroughly
dried over anhydrous sodium sulphate, protected from air
and light, stored under refrigeration and analysed quickly
to restrict reactions such as oxidation and hydrolysis
after distillation. Hence, variation in acid and ester values
is attributed mainly to the prevailing conditions during
distillation; e.g. the time of contact of geranium oil with
water is longer in the water distillation and redistillation
methods than in the steam distillation method. These re-
sults provide supporting evidence for the above assertions
that the higher the water content in the distillation tank,
the more hydrolysis of esters occurs and the reversible
reaction proceeds towards right-hand side to maintain the
equilibrium constant by forming corresponding acids and
alcohols.
In addition to the experiments described above, the
spent water (generally black in colour) from the distilla-
tion tank was tested for its acidity after the completion of
the distillation process and it was found that the pH was
2.8–3.8 and that of the distillate (hydrosol) was 4.5–5.5.
Thus, it is confirmed and that hydrolysis of esters does
occur to form the corresponding acids and alcohols at
higher temperatures, as mentioned earlier.
With respect to oil yields, total mono- and sesquiter-
penes, alcohols and ester content, steam distillation with
cohobation and with recycling produced almost similar
type of oil as that produced by water distillation method
in Clevenger apparatus and on a pilot scale. This can be
explained on the basis that recycled hydrosol, in steam
distillation with cohobation and recycling, continuously
Flavour Fragr. J. 2005; 20: 222–231
230 K. G. D. BABU AND V. K. KAUL
increases the level of water in the distillation tank while
the batch is under distillation, and this ultimately be-
comes water distillation method at the end, even though
the plant material is set up to undergo by steam distilla-
tion method at the beginning.
Conclusion
The study gives an insight of the quality of essential oil
produced from geranium plants by adopting different dis-
tillation techniques. A synergistic combination of the
steam-distillation method, the water–steam distillation
method and even the water distillation method is pro-
posed for the production of better quality and quantity of
geranium oil on a pilot scale. This can be achieved by
adopting improved design and processing techniques.43
The distillation unit used for this purpose in the present
investigation was equipped with a steam jacket, false
bottom, steam spurger, cohobation head column, recycl-
ing line, horizontal condenser and a receiver/separator.
In the beginning, the plant material is distilled using the
steam distillation method and the distillate collected in
the receiver is recycled to the distillation tank through a
cohobation column after separating the essential oil. As
distillation proceeds, the distillate from the receiver re-
cycled through the cohobation column starts accumulat-
ing at the bottom of the distillation tank, and the plant
material is distilled by water–steam distillation method.
On further prolonging the distillation period, the charge
can be distilled by the water distillation method. In this
unique type of distillation method, a particular quality of
geranium oil can be produced to meet the requirements
of the customer. As a result of this investigation and by
using the above-mentioned distillation methods, one can
produce particular a quality of geranium oils (such as es-
ter-rich and alcohol-rich) according to need. The esters
(which are responsible for characteristic heavy, lingering
aroma)-rich oil can be extracted in the first phase and
the whole oil (including oil dissolved in hydrosols, an
alcohol-rich fraction) can be recovered in the second
phase, which makes the process economically viable
by producing more oil yields and better quality oil. It is
understood that the geranium oil produced by the water–
steam distillation method, which contains more alcohols,
is preferred in the aromatherapy industry, but for other
purposes steam-distilled oil, which has a higher ester
content, is preferred. Esters comprise the largest and
most important class of compounds used in flavours and
fragrances.44 Therefore, depending upon the end-use of
the essential oil, one can distil geranium plant material to
obtain the required quality of oil by applying the above-
recommended different hydrodistillation techniques.
Acknowledgements—The authors are grateful to the Director, IHBT
(CSIR), Palampur, for continuous encouragement and for providing
necessary facilities during the course of this investigation. The authors
Copyright © 2004 John Wiley & Sons, Ltd.
also gratefully acknowledge the funding of this project (GAP-0024) by
ICEOFF-’89, New Delhi. Thanks are also due to Mr Kuldeep Singh and
Mr Balak Ram for their technical support services.
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