Natural Products in Perfumery

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Natural ProductsinPerfumery
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History

• First uses
• Natural gums olibanum, myrrh, galbanum
• Spices - cinnamon
• Herbs, aromatic woods
• Macerated in vegetable oils, heated
• Distillation of essential oils
• Flower waters rose, neroli
• Enfleurages jasmine, narcissus

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Natural Materials
Ethanol Solvent
Enfleurage Cold Extraction
Extraction Pressed
Tincture Concrete Pomade
(resinoid)
Ethanol
Ethanol Extraction Extraction

Essential Oil Absolute
Deterpenation
Terpeneless Oil
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Definitions
Essential oil Extracted by pressing or
steam distillation Concrete-Extracted
by solvent Absolute-Waxes in concrete
removed with alcohol
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PARTS OF PLANT
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Types of Natural Products

• Essential Oils
• Volatile material obtained from plants
• Concretes and Resinoids
• Solvent extracts of plant matter
• Absolutes
• Ethanol extracts of concretes and resinoids

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Essential Oils

• Volatile components of a plant, obtained from
  either the whole plant or a part of that plant
  (flower, leaf, bark, root, peel, etc.)
• Steam or water distillation
• Expression (cold pressing)
• Yields are usually 0.1 to 2-5

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Essential Oils

• Steam or water distillation
• Volatiles are entrained in steam
• Vapor condenses
• Essential oil separates
• Compounds can react

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Essential Oilsobtained by steam or water
distillation

• Spicy notes clove, nutmeg, pepper, cascarilla
• Herbal, camphoraceous notes lavender, rosemary,
  cedarleaf
• Floral notes ylang, rose, geranium
• Woody notes patchouli, vetiver, sandalwood,
  cedarwood

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Essential Oilsobtained by expression (cold
pressing)

• Citrus oils
• Orange
• Grapefruit
• Lemon
• Lime
• Tangerine
• Mandarin
• Bitter orange
• Bergamot

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Essential OilsRectification

• Fractional distillation
• vacuum 2 20 mm Hg
• low temperature
• tall separating column with packing
• Removes undesirable components
• Cleaner odor, low color, low residue

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Essential OilsFolding

• Rectification and concentration of citrus oils
• Removal of terpenes
• 10 fold start with 10 drums oil, remove 9 drums
  terpenes, create 1 drum of 10X oil

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Essential Oil Isolates

• Eugenol from clove leaf oil
• 1,8-cineole (eucalyptol) from eucalyptus oil
• Several from orange
• Octanal
• Decanal
• Valencene
• Sinensals

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Clove Oil Derivatives

METHYL ISOEUGENOL
ISOEUGENYL ACETATE
BENZYL ISOEUGENOL
VANILLIN
CARYOPHYLLENE
ISO EUGENOL
EUGENYL ACETATE
METHYL EUGENOL
BENZYL EUGENOL
DIHYDRO EUGENOL
CARYOPHYLLENE OXIDE
Distillation Fractionation Acetylation
Isomerisation Methylation Hydrogenation Oxidatio
n Mild Acid Reaction Benzylation
EUGENOL
CARYOPHYLLENE ALCOHOL
ESSENTIAL OILS
CLOVE BUD/LEAF/STEM
CARYOPHYLLENE ACETATE
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Expression Citrus Peel Oils

• Pellatrice Method
• Whole fruits grated or rasped action to yield
  particles of the oil-containing colored layer
• Refined through filtration and centrifuge
• Remaining intact fruit processed for juice
• Former methods include sponge and sfumatrice
• Oil components mostly monoterpenes, with some
  funtionalized terpenes and aliphatic esters
• Contain non-volatile components such as waxes

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Ylang Oils

• Main Growing areas
• Madagascar, Comores
• Description
• Short tree with yellowy-green flowers and
  carmine-red spots in the center
• Part of plant used
• Flower petals
• Harvest Time
• May to July and November to December

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Ylang Oil Fractions
Fractions made during initial distillation
More woody spicy odor
More floral odor
Extra
First
Second
Third
Increasing Distillation Time
Decreasing Density (!)
Higher Ester Content
Complete
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Natural Ylang Products

• Ylang Extra
• Contains more esters
• Ylang I
• Ylang II
• Ylang III
• Contains more phenolic, woody notes

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Traditional Natural Specialties

• Folded Oils via distillation
• Orange 5X, Orange 10X
• Isolates via distillation
• Citral, Eugenol, Nerolidol, Geraniol, Nootkatone

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Nontraditional Natural Specialties

• Fractions via technical distillation
• New olfactive characters
• Ylang Fraction G
• Patchouli Fraction
• Vetiver Fraction
• Reduction of specific materials
• Methyl eugenol
• Safrol
• Estragol

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Enfleurage

• Expensive Process
• Low Yield
• Used on two types
• of flowers
• Jasmin
• Tuberose

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Concretes

• Concrete is obtained
• from fresh plant matter
• and flowers which are
• non-resinous or low
• resinous materials.

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Extractions - Concretes

• Material extracted with volatile nonpolar solvent
• Solvent evaporated away in vacuo leaving
  concentrated product
• Contains plant waxes and other odorless
  fixatives (based on solubility in extraction
  solvent)

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Resinoids

• Resinoids are obtained from dry
• plant matter and gums.

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Absolutes

• Absolutes are highly concentrated,
• they are entirely alcohol soluble, and
• are usually liquid materials.

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Fragrance Natural ProductsCommercial Categories

• Pure and natural
• Natural
• Perfumery (or commercial grade)
• Extenders
• Replacers
• Organic

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Natural ProductsCommercial Aspects

• Prices are cyclical
• Quality can vary
• Supply can be inconsistent due to
• Weather
• Harvest time
• Demand
• Processing problems
• Political instability

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Eau de Cologne 1709
1 lb
Rose Oil 2 drams Melissa Oil
2 drams Neroli Oil 5 drams
Lavender Oil 6 drams Geranium Oil 8
drams Rosemary Oil 9 drams Lime Oil
1 oz Cedra Oil 2
oz Petitgrain Oil 2 oz Orange Oil
2 oz Lemon Oil 3
oz Bergamot Oil 4 oz
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Historic Shift
The development of organic chemistry in Germany
in the late 1800s led to the synthesis of many
new aromatic materials
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Possibilities

• Natural
• Synthetics Existing in
  nature Not existing in
  nature

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All Natural BQT
Bergamot oil 20 Geranium oil
150 Palmarosa oil 200 Sunflower
oil 210 Turkish rose oil
50 Rosewood oil 150 Sandalwood oil
100 Vanilla absolute 10 Violet leaves
abs. 10 Ylang ylang oil 100
1000
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Problems With Naturals

• Price
• Skin irritation
• Decomposition
• Discoloration

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The Changing Face of Natural

• Traditional Definition
• Defined by suppliers themselves
• Obvious(?)
• Products derived from the plant kingdom, animals
  (or their secretions) via extraction, expression,
  or distillation without intentional chemical
  reaction or change

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The Changing Face of Natural

• New Definition(s) for the 21st Century
• Defined by
• end user / consumer / marketplace
• Not as clear-cut
• Products obtained from the plant kingdom (or
  animals?) using entirely natural methods and
  materials such as heat and water

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Crop Production Techniques

• Traditional
• OK to use chemical fertilizers, pest control
  agents and irrigation to maximize yield and/or
  quality
• Organic
• Plantations conforming to organic standards
  allowing some natural fertilizers and/or pest
  control
• Beyond Organic Biodynamic
• Plantations planted for the purpose of harvest
  but left completely in the wild with no
  irrigation, pest control or fertilization