Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

Advanced practical course

for Organic Chemistry
WS 2012/13

Report

Steam distillation of juniper berry oil

from juniper berries

Leipzig, 6th November 2012

Supervisor: Prof. Dr. Sicker, M.Sc. Liang Xia

Intern: Benedikt Schwarze (2263057), Daniel Meyer (2258970)
Handover date: 06.11.2012

Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

TABLE OF CONTENTS
1

Introduction.................................................................................................................................................................3

Experimental part ....................................................................................................................................................4

Analytical facts..........................................................................................................................................................4

Discussion...................................................................................................................................................................6

References .................................................................................................................................................................6

Appendix ......................................................................................................................................................................7

Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

Juniper berry oil

1 INTRODUCTION
In this laboratory exercise juniper berry oil will be isolated by steam distillation from
juniper berries. This essential oil is a mix of fragrant compounds like -pinen, pinen, etc., which belong to the terpenes, the terpenoids and their oxygen containing
derivatives.
The direct distillation of juniper berries is impossible, because most compounds of
the oil have a high boiling point and would decompose under higher temperatures.
Therefore it is milder to use steam distillation to isolate the essential oil.
Steam distillation is a useful and selective separation process for temperature
sensitive volatile compounds that are not or only poorly miscible with water.
In our case the option of the live steam generation is used to generate steam from an
external steam source. The steam, which is conducted into the distilling pot, carries
the oils vapor into the distilling head and then into the condenser, where the oil and
water co-condense. This type of a so called azeotropic distillation only works
because of the fact that oil and water are immiscible and boil independent of each
other distillation.

[1][2]

Heating of such a mixture of two nearly immiscible liquids

forces each constituent to independently exert its own vapour pressure, in a manner
as if the other compound(s) were not existing. Continuous heating leads to a
temperature where the sum of the added single vapour pressure matches the
atmospheric pressure. With water as the main compound this boiling temperature is
close to 100 C, but always below. By this method, many hydrophobic but volatile
organic compounds can be selectively removed from their natural raw materials
distinctly below their own boiling points as pure liquids (e.g. -pinene which has a bp
of 155 C).

Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

2 EXPERIMENTAL PART
200 g of intact juniper berries and 2000 mL water were put into a 4-L-triple-neckedflask. The distillation was stopped at an amount of 1500 mL of distillate, which was
extracted with 580 mL MTBE. The extract was dried and the solvent was removed
under reduced pressure (500 mbar, 40 C). The distillation yielded 250 mg of an
yellow-brown oil.
The setup for steam distillation looks like in figure 1.

Fig. 1: Still for steam distillation of juniper berries

[4]

3 ANALYTICAL FACTS
To roughly analyze the composition the essential oil a 1H-NMR-spectrum was taken.
Solvent: CDCl3
Mass: 50 mg
Test frequency: 300 MHz

Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

Of course the oil is a mixture of many compounds, which are not all known. But the
main compound in the mixture is supposed to be -pinene. To proof this, a second
spectrum was taken of pure -pinene from our lab. The spectrum of -pinene was
taken from [6].

Fig. 2: - and -pinene

It is mainly hard to analyze the aliphatic part of the spectrum, since there is a mixture
of many compounds, whose signals overlap. Nonetheless there are specific shifts in
both the spectrum of the oil and the spectra of the pure pinenes.
Tab. 1: aliphatic shifts of the spectra

-pinene

-pinene

Juniper Berry Oil

=0.80 ppm

=0.70

=0.80

=1.30 ppm

=1.20

=1.20; =1.23

=1.60 ppm

=1.470

=1.60; =3.25

From the aliphatic part it is not obvious if only one or both pinenes are components of
the oil.
Hence the olefinic part of the spectrum has to be analyzed, since -pinene has only
one olefinic proton and -pinene has two.
Tab.2: olefinic shifts of the spectra

-pinene

-pinene

Juniper Berry Oil

=5.2 (s)

=4.6 (d)

=5.2 (s)

The olefinic part gives the information which is needed. For there is a singlet at a
chemical shift of 5.2 ppm in both the spectrum of -pinene and the juniper berry oil, it
is obvious that the one of the main components of the oil is -pinene.
In the spectrum of the oil there are some shifts in the aromatic part, which cannot be
interpreted. On principle, a gas chromatogram would give further informations.

Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

4 DISCUSSION
The yield of 250 mg of juniper berry oil from 200 g juniper berries is rather small.
Hence the practical application has to be improved. The first idea is to reduce the
juniper berries to small pieces, so the steam can better release the essential oil
components, since there is no shell protecting fragrant compounds.
The second idea comes from the gin production. Some distillers dilute the spirit
alcohol with water to 45% (percentage by volume) and put it together with juniper
berries and other (!!) botanicals into a copper pot still for one day to one week so
the alcohol can absorb the flavors. This process is called maceration and gives low
quality gin. To complete the distillation process the grain distillate is heated up and
the volatile alcohol with the extracted flavors is collected at 86-89C.
Other distillers, who make superior quality gins, use the vaporization process. The
botanicals are placed in a copper basket or cheesecloth and suspended above the
alcohol in the pot still while the spirits are boiled. The vapor soak the contents of the
botanicals and transfer the flavor to the alcohol.[5] However, the intention for this
exercise was not to make gin, but to increase the number of steam distillation
examples. In this respect it was both interesting and sufficient for a first trail.

5 REFERENCES
[1] S. Hnig et al., Arbeitsmethoden in der organischen Chemie, 2006, Lehmanns
Media, S.110
[2] http://infohost.nmt.edu/~jaltig/SteamDistill.pdf (Stand: 05.11.2012)
[3] http://www.heilkraeuter.de/lexikon/wacholde.htm (Stand: 05.11.2012)
[4] Still by courtesy of S. Aurich, WDD Apparatur Kamille zu Chamazulen, 2008
[5] http://www.ehow.com/how-does_5453310_distillation-process-gin.html
(Stand: 05.11.2012)
[6] http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi
(Stand: 05.11.2012)

Benedikt Schwarze, Daniel Meyer

OC-F-Practical course WS 2012/13

Steam distillation of juniper berry oil

6 APPENDIX

Spectrum of -pinene from the SDBS database (enclosed)

CAS-Registry-Number of -pinene: 7785-26-4

H-NMR-spectra of juniper berry oil (extra file)

H-NMR-spectra of - and -pinene (extra file)