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Journal of Essential Oil

Research
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Extraction of Essential Oils.

Part III. Two-Stage Production
of the Oil of Lavandula
angustifolia Mill.
a

Thierry Bernard , Francis Perineau , Michel

a

Delmas & Antoine Gaset

Laboratoire de Chimie des Agroressources , Ecole

Rationale Superieure de Chimie (INPT) , 118 Route
de Narbonne, 31077, Toulouse Cedex, France
Published online: 28 Nov 2011.

To cite this article: Thierry Bernard , Francis Perineau , Michel Delmas & Antoine
Gaset (1989) Extraction of Essential Oils. Part III. Two-Stage Production of the Oil of
Lavandula angustifolia Mill. , Journal of Essential Oil Research, 1:6, 261-267, DOI:
10.1080/10412905.1989.9697796
To link to this article: http://dx.doi.org/10.1080/10412905.1989.9697796

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RESEARCH REPORT

J . Ess. Oil Res., 1,261-267, (Nov/Dec 1989)

Extraction of Essential Oils. Part 111.

Two-Stage Production of the Oil of
Lavandula angustifolia Mill.
Thierry Bernard, Francis Perineau*, Michel Delmas and Antoine Gaset
Laboratoire de Chimie des Agroressources,
Ecole Nationale Superieure de Chimie (ZNPT),118 Route de Narbonne,
31077 Toulouse Cedex, France
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Received: March 1989

ABSTRACT: Although lavender oil generally is produced by steam distillation of the harvested flowering tops of Lavandula angustifolia, the use of a
two-stage production method was examined. First, the flowering tops were
(CFC-113) to yield a conextracted with 1,1,2-trichloro-1,2,2-trifluoroethane
crete. The concrete then was steam distilled to produce an oil of higher yields.
GC/MS analysis showed that the oil produced in this way was richer in sesquiterpenes than a steam distilled oil. Seventy-three compounds, representing 81.8% of the total essential oil, were identified. The remaining 18.2% was
comprised mainly of compounds with molecular weights greater than 220.
KEY WORD INDEX: Lavandula angustifolia, Labiatae, extract, essential oil,
combined extraction and distillation, CFC-113.
INTRODUCTION: 1,1,2-Trichloro-1,2,2-trifluoroethane(CFC-113 or
Freon-113), which is an efficient solvent for both fats and aromatic compounds, is also known for its dehydrating activity on vegetable products. Recently, we exploited these properties in a study on ambrette seed extraction
(1).This solvent made it possible for us to obtain a concrete with an excellent
aroma from which the essential oil could be obtained by steam distillation.
Two other commercially important plant materials (Chinese star anise, Z l licium verum, and cinnamon bark, Cinnamomum zeylanicum) also have been
extracted with CFC-113 to produce concretes of excellent aroma quality (2).
In this study, we examined the efficacy of using CFC-113 as a solvent to
produce lavender concrete from which the oil could be distilled. A reason to
do this is because lavender oil is a commercially important essential oil, with
France producing about 50 tons per year (3).We examined the oil produced
from the concrete using GUMS. Although steam distillation is the usual
method for the production of lavender oil, we thought that a combination of
extraction followed by steam distillation would be a more reproducible oil
preparation method. It would also permit the possibility of recovering the
potentially interesting natural lavender waxes.
It is reported that upon distillation of the flowering tops of L. angustifolia, the
oil yield is 1.2% to 2.8%(4-6).According to the published literature (4,7-9), the
*Senior author
261

JOURNAL O F ESSENTIAL OIL RESEARCH

262

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main components found in the oil are: monoterpene hydrocarbons (1.4-18.6%)

including cis- and trans-ocimene, etc., monoterpene alcohols (28.4-59.3%) including linalool, terpinen-4-01, etc., monoterpene esters (22.6-49.0%) including linalyl acetate, lavandulyl acetate, etc., and sesquiterpene hydrocarbons
(0.4-7.6%)including p-caryophyllene, etc.

EXPERIMENTAL: Extraction was carried out with,a soxhlet extraction thimble of 0.5dm3 volume within which was placed the dried flowering tops of
lavender. The two-necked ldm3 flask was half filled with 1,1,2-trichloro172,2-trifluoroethane(CFC-113haN, was bubbled through a diffuser connected
to the narrow neck (10).The large neck was connected to the soxhlet assembly
which possessed two condensers through which a cryogenic liquid was mechanically pumped at a controlled -20C. The pot temperature was controlled
at 48C. The extraction time was calculated once boiling had started. It was
expressed according to the number of siphonages. From the results of previous studies (l,2), extraction time was set at 20 siphonages.
Once the solvent had been removed from the concrete, it was steam distilled
to produce the essential oil. The relative density at 20"C, optical rotation and
other physico-chemical properties of the resultant oil were determined according to the standards of the French Normalization Association, AFNOR
(11).
Component identification was performed using gas chromatography coupled
to mass spectrometry (GCIMS). Analyses were run on a Ribermag R-10-10
coupled to a Delsi 700 chromatograph equipped with a 0.29 mm (i.d.) x 50 m
Carbowax 52 capillary column. The column temperature was maintained at
70C for five minutes and then raised to 220C at 2"C/min. Identification was
carried out with EPA-NIH and SPECMA data bases. Kovats' indices and the
peak enrichment technique were used to confirm the spectral identification.
The Kovats' indices (KI) were calculated from scannings after setting up a
linear regression of 10 reference products for which KI were known.
Quantitative analyses were carried out by gas chromatography on a Intersmat
IGC 120 FL, coupled to a Shimadzu CR3A integrator, equipped with a 0.22
mm (i.d.) x 50 m Carbowax 20 M capillary column. Helium at a pressure of 2
Table 1. Extractionand DistillationYield of
Lavandula angusfifolia Flowering Tops.

Dry Plant
Material (9)

Concrete
Yield (%)

Steam
Distillation
Time (h)

Lipid
Yield ( O h )

Essential
Oil Yield (Yo)

1 1 1.97

25.00

2.26

2.30

127.95

22.53

2.20

2.66

194.77

24.17

2.30

2.30

2.02

"Was obtained as FORANE 113 from Atochem. Ltd.

263

JOURNAL O F ESSENTIAL OIL RESEARCH

kg/cm2was chosen as the carrier gas. The injector and flame ionization detector temperatures were fixed at 260C. The column temperature was maintained at 70C for three minutes and then raised to 220C. The column temperature was maintained at 70C for three minutes and then raised at 220C at
2"C/min. Injection volume was 0.04 pl.
Table II. Physico-Chemical Characterization of Lavender Oil.
~~

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Physical
Constants

Gildemeister
& Hoffman (10)

Authors
AFNOR
(11)

Naves

CFC-113
Extraction/
Steam
Distillation

Density
620C
20C

0.885-0.895

0.877-0.890

0.893-0.898

0.895

Refractive
Index
1720C
D

not reported

1.4580-1.4640

1.464-1.467

1.4610

Optical
Rotation
a20"c
D

-3" to -9"

-1l"to +7"

-7"43' to -8'50'

4'25'

Essential
Oil Yield

1.2-2.8%

not reported

1.3-2.2%

2.30-2.66%

RESULTS AND DISCUSSION: The optimum yield of essential oil obtained

by CFC-113 extraction followed by hydrodistillation was reached with an
extraction time of two hours (corresponding to 20 soxhlet siphonages) and a
steam distillation time of four hours (Table I). The oil yield of 2.66% was quite
comparable with the previously published yield of 1.2% to 2.8% (12). The fat
(fixed oil) recovered under these operating conditions after hydrodistillation
was 2.3%. Analyses of residual fats indicated a content in non-extracted lipids
of 1.7%. The essential oil obtained by this two-stage technique of extraction,
followed by steam distillation, was a pale yellow, mobile liquid with a strong
characteristic lavender aroma. Examination of the physico-chemical constants
showed that the oil is similar to those previously examined (12,13) and conformed to the standards of AFNOR (11)as shown in Table 11. The chemical
composition of the oil can be seen in Table 111. The 73 constituents characterized represent 81.82% of the total essential oil. Most of the components not
identified had a molecular weight greater than 220 with KI values on a polar
column of 2180-2700. It is speculated that these are probably sesquiterpene
ketones and esters perhaps with caryophyllane, humulane, and/or cadinane
skeletons. If the results obtained in this analysis are compared with the previously published studies (4,7,9) for monoterpene hydrocarbons, alcohols, esters, and sesquiterpene hydrocarbons, the following can be seen:

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monoterpene hydrocarbons:
monoterpene alcohols:
monoterpene esters:
sesquiterpene hydrocarbons:

Previously Published (4,7,9)

3.2-18.6%
28.4693%
22.6-49.0%
2.7- 7.6%

Our Results
2.6%
25.9%
27.8%
6.1%

We feel that the low level of monoterpene hydrocarbons found could be

explained by the fact that freshly harvested flowering tops normally are used
for commercial oil production and the dry plant material used to produce our
oil had probably lost some of the more volatile compounds. The monoterpene
alcohols and esters in our oil were noticeably on the low side when compared
with the published data. This can be explained by the postulate that internal
degradation of linalool and linalyl acetate, as described previously (14,15),
accounted for the low levels found. The presence of myrcene (0.39%),transp-ocimene (0.57%),and neryl acetate (3.23%)infers this degradation. In addiTable 111. Compositionof the Oil of Lavandula angustifolia Produced by
the Two-Stage Process.
Compound

K. I.

Percentage
A

Composition
B

2-hexanone
a-thujene
a-pinene
camphene
ppinene
sabinene
trans-2-hexenyl acetate
b3-carene
myrcene
limonene
1,&cineole
butyl butyrate
cis-p-ocimene
3-octanone
trans-p-ocimene
p-cymene
terpinolene
6-methyl-5-hepten-2-one
3-octanol
hexenyl acetate
n-hexyl butyrate
cis-linalool oxide (furanoid)
1-octen-3-ol
camphene hydrate
trans-linalool oxide (furanoid)
1,2-Iimonene epoxide
octyl acetate
camphor
linalool

1040
1045
1050
1070
1095
1104
1117
1126
1140
1170
1176
1185
1210
1220
1230
1250
1268
1325
1350
1354
1395
1415
1420
1430
1435
1440
1460
1485
1535

0.02
0.03
0.07
0.09
0.09
0.02
0.01
0.01
0.39
0.22
2.58
0.06.
0.59
0.08
0.57
0.14
0.05
0.04
0.07
0.66
0.02
1.54
0.54
0.10
0.78
0.71
0.02
2.90
20.90

1.53
0.76
0.68
0.13

0.1 1
0.29
2.06
4.31

1.16

0.48
1.06

3.67
44.44

JOURNAL OF ESSENTIAL OIL RESEARCH

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Table 111, continued.

Compound

K. I.

linalyl acetate
6-methyl-3,5-heptadien-2-one
bornyl acetate
a-santalene
terpinen-4-ol
trans-crbergamotene
pcaryophyllene
hexenyl butyrate
neryl acetate
hexyl hexanoate
octyl propanoate
p-bisabolene
cis-pfarnesene
wterpineol
borneol
trans-p-farnesene
piperitone
germacrene D
carvone
cis-linalool oxide (pyranoid)
geranyl acetate
rbisabolene
a-farnesene
estragole
trans-linalool oxide (pyranoid)
ycadinene
nerol
neryl propanoate
p-mentha-l,5-dien-7-01
dihydro-p-cymen-8-01
trans-anethole
cis-carveol
p-cymen-8-01
geraniol
a-calacorene
cis-3-hexenyl octanoate
caryophyllene oxide
cinnamaldehyde
cis-3-hexenylnonanoate
cis-3-hexenyldocanoate
6,10,14-trimethylpentadecanone
acetoeugenol
eugenol
a-cadinol

1550
1567
1572
1576
1584
1593
1600
1594
1603
1612
1618
1625
1676
1680
1683
1696
1704
1707
1710
1719
1724
1730
1733
1740
1746
1760
1764
1769
1770
1793
1810
1815
1820
1830
1900
1970
1950
1996
2000
2070
2000
2105

A = CF-113 extraction/steam distillation

B = Steam distillation (4)
t i = Trace (<0.01%)

2160

Percentage
A
25.06
tr
0.24
0.76
2.03
tr
3.00
0.80
2.23
0.03
0.26
0.10
1.oo
0.70
1.70
0.08
tr
0.23
0.06
0.29
0.13
tr
tr
tr
0.13
0.85
0.21
0.14
tr
0.03
4.62
0.05
0.09
0.26
0.12
0.56
2.1 1
0.32
0.02
0.14
0.02
0.05
tr
tr

Composition
B

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JOURNAL OF ESSENTIAL OIL RESEARCH

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tion, our oil contained both oxides of limonene and linalool. The formation of
these oxides has been discussed by Hoffman (16). We feel that the formation
of these oxides is not specific to our two-stage production procedure (17).
The sesquiterpene hydrocarbon content of our oil is on the high side when
compared to the previously published data. In addition to p-caryophyllene
(the major component), we also characterized a-santalene, trans-a-bergamotene, p-bisabolene, cis-p-farnesene, trans-p-farnesene, germacrene D,
y-bisabolene, a-farnesene, y-cadinene, and a-calacorene. The characterization of caryophyllene oxide shows that the two-stage technique produces an
oil richer in high boiling compounds. We made a similar observation on the
extraction of aromatic compounds from celery seed and lovage root. We
noticed that CFC-113 could extract heavy compounds not recovered by direct
hydrodistillation thereby producing a richer essential oil with a strong and
lasting odor (18). Moreover, after direct hydrodistillation, residual celery
seeds were extracted by CFC-113 and a concrete containing 85% of
phthalides was obtained. This confirmed the efficiency of CFC-113 for the
extraction of less volatile compounds not easily accessible by steam distillation.
In summary we would like to report that the use of a combination of CFC113 extraction followed by steam distillation is an efficient way to produce a
quality oil of lavender with a strong, lasting aroma. The chemical composition
of the oil produced in this manner is quite similar, although it is richer in high
boiling compounds.
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