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Essential oils: Extraction, Applications & Analysis

Presentation · January 2015

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 ESSENTIAL OILS
Extraction, Applications
and Analysis
Amr Edris
Aroma & Flavor Chemistry Department
National Research Center
Cairo, Egypt
amr_edris@[Link]
 What are Essential Oils ?

Volatile fraction of aromatic & medicinal plants

(Essential oil = volatile oil)

 Chemical Difference between
essential oil and fixed oil

From oil seeds

Fixed oils Triglyceride

“Building unit”
 Essential oils

From aromatic plants

2 – 4 unites
Isoprene
“Building unit”
Essential oil

Terpenes
 Difference between essential oil and fixed oil

Essential oil Fixed oil

Source

Building unite

(isoprene) (triglyceride)

Nutritional value Non-nutritive Nutritive

(no calories) (high calories)

Olfactoric highly fragrant non

Properties

Volatility volatile non-volatile

 What is the part of plant that contain essential oil ?

Flowers Herbs Seeds Bark Buds

Rose lemongrass Caraway cinnamon Clove

 What are their functions in the plant ?

1- Protection

* Harmful insects
*Bacterial disease

2- Attraction

Pollinating insects for pollination

 Essential oil in secretion glands

Lavender flower Sweet basil Sage leaf

 Extraction of essential oils

1- Distillation

[Link]
 Extraction of essential oils

1- Distillation

Medievals Now days

 1- a Water distillation

Distill.
Aromatic plant + water Essential + water
Industrial scale water distillation

Essential oils with burnet aroma !!

 1-b- Steam distillation

Essential oils with good quality !!

 Industrial scale steam distillation

Steam is generated outside

 1-c- Water and Steam distillation

Used in case of hard aromatic plants like

seeds of parks
Cloves Cinnamon
1- d- Microwave assisted extraction of essential oils
 Advantage

- Reducing extraction time (due to fast heating)

- Decreasing fuel consumption & CO2 emission to the environment

 Delicate flowers get HURT
From distillation

Jasmine

Rose

Orange flower
 2- Fat extraction
The Enffleurage Method
(for delicate flowers)

(France 1800’s)
 Extraction material

Heat Cool

Fat Melting Tallow

Wooden chassais Stacked chassais

 After fat is saturated with the oil

1- Chassais extracted with ethanol

2- gives ethanol + essential oil
3- Evaporate ethanol

“Essential oil”
Absolute flower oil

The Best Finest Grade

 3- Solvent extraction
For Mass Production

Jasmine

Rose

Orange flower
 2-a- Extraction Using Organic Solvent
(Hexane or petroleum ether)

Evaporation
Hexane
soaking

Absolute flower oil

(Most pure & expensive)

Evaporate
Ethyl alcohol
Ethyl alcohol + oil Refrigeration
Filteration Concrete
Oil + Wax +Pigment
1000 Kg rose =
2.5Kg concrete =
1.3 Kg absolute oil
(0.13% of flowers weight)

1000 Kg jasmine =
2.5 Kg concrete =
1.4 Kg absolute oil
(0.14% of flowers weight)
Problems with solvent extraction
2-b- Using supercritical gas extraction
 At the supercritical pressure & temperature:
gases have two important characters

Flow ability like a gas

Extraction ability like solvent

So it can defuse through plant tissue & extract essential oils

Which gas would you like to use for super
critical extraction of essential oil ?

Yes: CO2
All you need is to adjust the pressure and the temperature
to bring CO2 to supercritical gas

Enjoy extracting E. oils

33
Trade
 Global market (2011)
of essential oil used in fragrance and flavor was estimated at

US$ 24 billion
The United Nations Comtrade statistics, (2011)

Major consumers

40.0% 30.0% 7.0%

 Prices of some essential oils
Oil type Price ($) for 1 Oz (28.34g)

Sandal wood 167.0

Jasmine absolute 137.0
Orange flower oil (Neroli) 168.0 Expensive
Rose oil absolute (Bulgaria) 168.0
Rose oil absolute (Russia) 88.0
Chamomile (German) 90.0
Chamomile oil (Roman) 55.0

Frankincense 30.0
Geranium oil (Burbon) 28.0 Average
Basil oil 14.0

Peppermint oil 7.0

Cinnamon leaf 5.0 Cheap
Citronella 4.0
Spearmint oil 4.0
Adulteration of
Essential Oils
 Types of adulteration

1- Increasing volume
(adding organic solvents)

Benzyl alcohol
Vegetable oils, Mineral oils
Diethyl phthalate

Invisible Visible
can not be detected by can be detected by
Gas chromatography Gas chromatography
 2- Adulteration by
addition of cheaper oils

Original essential oils Cheaper essential oils

Cinnamon bark oil Cinnamon leaf oil

Grapefruit oil Orange terpenes

Lavender oil (Lavandula anguestifolia) Lavandin (lavadula intermedia)

Peppermint oil (Mentha piperita) Cornmint (Mentha arvensis)

Rosemary oil Eucalyptus oil

 3- Adulteration by
addition of synthetic chemicals

Original oil Synthetic odor character

Anise oil Anethol
Basil oil linalool & estragol
Berganolt oil linalyl acetate
Caraway seed oil (+) Carvone
Spearmint oil (-) Carvone
Coriander oil linalool
Cumin seed oil cuminaldehyde
Lemongrass oil citral
Rose oil (-) citroneloll
Applications & Uses
 1- Application in Perfumes

The word perfume comes from the Latin phrase:

"per" meaning "through"
"fumus" meaning smoke."
 The most 3 famous flowers used in perfume industry

Jasmine rose Bitter Orange

83% of 75% of all

female
perfumes
perfumes ?

43
 2- Application in cleaning formulas
de-greasing Cleaners

Orange peel Limonene Dish washing formula

essential oil Powerful de-greasing
90.0% of orange peel oil
 3- Application in Disinfectants
antiseptic, antiviral, and antifungal properties

Colve Thyme & Oregano Cinnamon bark

&

Eugenol Cinnamic aldehyde

Embalming
Modern applications of essential oils as
antimicrobials for food preservation
1- Active paper packaging

Paper coated with Normal paper

4.0% cinnamon oil

Progress in Organic Coatings 60: (2007) 33–38

 3- Application in Flavors

Spearmint &
Peppermint

Orange peel

Clove &
Cinnamon
Flavored water
Hydrosol
 4- Application as Green Pesticides

Many plant pests attack crops leading to great lose

2.5 million tons of pesticides are used on crops each year

The damage caused by pesticides reaches $100 billion annually.

Essential oils as alternatives !

Anti-feedants (prevent eating)

Repellent (repells)

Ovicides (kill the eggs)

Attractants (collect insects)

 4-1 Mosquito repellent

Msq, are a vector of several tropical diseases such as

Zika

yellow fever, dengue, malaria & filariasis

 DEET (synthetic compound) is the most
famous mosquito repellent

7.0% formula give repellent action for ~ 4 hours

80.0% formula give repellent action for ~ 14 hours

Problem
Skin irritation, Rash, Allergy
Natural alternative

Pyretherum
 Essential oils
Citronella essential oil
(since 1900s)

1.0%

Mosquito repellent activity

 Citronellal
Is the active mosquito repellent
(~ 40.0% of citronella oil)

Mosquito repellence activity 77.8%

(Approved for topical applications on the skin)

 How to use essential oils as repellents

1- as fumigants

2- as topical creams

3- in Fabrics
5- Application in Aromatherapy
 Aromatherapy is the use of essential oils for

Changing mood
Relaxation Improve body function
Relief stress

“It is a form of complementary therapy”

 European J. Prev Cardiol. 2012 Nov 29

Exposure to essential oil for 1 hour was found to be an effective

method of relaxation, as indicated by decreases in the Hart rate
and Blood pressure.

Prolonged exposure for longer than 1 hour to essential oils may

be harmful to cardiovascular health among spa workers.
 Lavender essential oil Migraine Headaches
‫الصداع النصفى‬

Inhalation for 15 minutes

129 headache attacks in cases, 92 responded entirely or partially to lavender.

European. Neurology 2012; 67(5):288-91

 How to diffuse
Essential oil

TISSUE TERRACOTTA PENDANT NECK BURNER--HEATER

PLUG-IN ULTASONIC MIST NEPULIZER

National Association of Holistic aromatherapy

[Link]
Massage therapy
 Never use concentrated essential oils on the skin
It will cause burns !!

Dilute essential oil with carrier oil like:

Jojoba oil, carrot seed oil, sesame oil, grape seed oil wheat germ
oil, evening prime rose oil
 1996

Robert Tisserand

69
70
Value addition to essential oils
 Fractionation distillation technique

Fractionating column

Example: fractional distillation of crude oil (petrol)

 Fractionation of essential oils

Fractionating column
 Fractionating column

Heli-back Rasching rings

Wire mesh Teflon balls

Fractionating column

Rasching rings
Fraction
collector
 Pure fractions from Essential oils
1 2 3

Limonene Citral Geraniol

(90.0% Orange oil) (80.0% lemongrass oil) (40.0% rose oil)

4 5 6

(-) carvone Eucalyptol Cinnamaldehyde

(75.0% Spearmint oil) (80.0% Eucalyptus oil) (90.0% Cinnamon oil)

 Fractional cooling

Slow cooling

- 40.0C for
1 week

Peppermint oil` Menthol

45.0% of the oil
Storage of essential oils
 Stability of essential oils during storage

81
 That will lead to deterioration in

1- Taste (oxidation)

2- Fragrance (oxidation)

3- Viscosity (polymerization or resinification)

4- Biological activity (skin sensitization & dermatitis)

82
 1- Light
can lead to isomerization

Anise essential oil

(80.0% trans-anethol)

(UV)

cis- anethol
trans- anethol

83
 Protection from light
Store in amber glass or Cobalt blue bottles

Aluminum essential oil bottles

84 (Lines with enamel or epoxy)
 2- Oxidation

90.0% of
orange oil

85
 Protection from oxidation

File the bottle to the neck to expel all oxygen

Head
space

86
 3- Heat
Every 10C rise in temperature will double the rate of
oxidation reaction (Vanthoff rule)

Store your oil in refrigerator or cooler

87
 Orifice reducers

88
 Analysis of essential oils

Polarimeter Refractometer

GC or GC-MS
 How GC Work?

Collector

GC FID
 Retention time (minutes)

Gas chromatogram

Report
Peak Number Time (minutes) Area (uV*sec) Area %
1 15.0 94864.4 0.4
2 19.4 1552476.15 28.2%
3
4
 How GC-MS Work?

MS GC
identification separation
(2) (1)
 How GC-MS Work?

70ev
Mass Fragmentation
Electronic Mass spectral library Soft wares

(mass fragmentation patterns of 1000,000’s of compounds)

Examples:
NIST
Chemistation (HP)
?

Match
GC- Olfactometry

MS/
GC- Olfactometry
 Thanks

amr_edris@[Link]
 Benzene ring may also present

Carvacrol Thymol Eugenol Cinnamic aldehyde

EO Thyme & oregano EO Clove EO Cinnamon

1- Peppermint 1(a)- Menthol 2- spearmint 2(a) (-) Carvone

‫نعناع فلفلى‬ ‫نعناع بلدى‬

3- Lavender 4- Basil 5- Orange leaf

‫الفندر‬ ‫ريحان‬ ‫ورق البرتقال‬
 Benzene ring may also present

Carvacrol Thymol Eugenol Cinnamic aldehyde

EO Thyme & oregano EO Clove EO Cinnamon

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