Vegetable Oils

Reporter: Soriano, Jerico B.

BS Biology – 4B
ORIGIN

 Such oils have been part of human culture for millennia. Oils such as
poppy seed, rapeseed, linseed, almond oil, sesame seed, safflower, and
cottonseed were variously used since at least the Bronze Age in the
Middle East, Africa and Central Asia. Vegetable oils have been used for
lighting fuel, cooking, medicine and lubrication. The Chinese started to
use vegetable oil for stir-frying instead of animal fats during the Song
dynasty (960–1279). Palm oil has long been recognized in West and
Central African countries, and European merchants trading with West
Africa occasionally purchased palm oil for use as a cooking oil in Europe
and it became highly sought-after commodity by British traders for use as
an industrial lubricant for machinery during Britain's Industrial
Revolution. Palm oil formed the basis of soap products, such as Lever
Brothers' (now Unilever) "Sunlight" soap, and the American Palmolive
brand, and by around 1870, palm oil constituted the primary export of
some West African countries.
Where is the oil located?

 Plants use stored oil as food for germinating

embryo, caloric content is high so is efficient
storage material. Double that of carbohydrates
and proteins.
 Oil can be stored in endosperm (castor, coconut),
cotyledons (peanut, soybean), scutellum (corn),
fruit pulp (palms and olives).
 Seeds have organelles called as glyxosomes that
convert fatty acids into carbohydrates during
germination.
Oils

 Mainly hydrocarbons made up of

 Glycerol (backbone) with three fatty acids chemically bonded to it -
triglycerides
Cholesterol
Unsaturation

 The number of double bonds determines the

level of saturation.
 Vegetable oils are complex mixtures and
saturation levels cannot be calculated directly
very easily;
 % saturation is determined by Iodine method,
 Iodine breaks ='s and is incorporated.
Amount of Iodine left over is determined.
Iodine values range from 7 to >200. 70 are
called fats (solid at room temperature) and
higher values correspond to more
unsaturation.
Unsaturation and Iodine Value

 Drying - >150 thin film will dry into impervious coating

 Semidrying - 100-150
 Nondrying - 70-100
 Fats 70
http://discovermagazine.com/2001/mar/featchemistry/
 Soap making

 Soap is salt of fatty acid

                                       
     
+3NaOH          
3 RCOO-
Na+
+
                                            
Soap Making

 Water lye (Base)

 Add oil or fat
 Glycerol and fatty acids separate
 Fatty acids will react with base to form salt of fatty acid
 Head which is soluble in water
 Tail soluble in oil
Oil Paints and Varnishes

 Drying or semidrying oils (linseed & tung oil)

 oil paints are boiled with heavy metal containing
compounds (Mg, Co, Pb) which help oils absorb
oxygen and form a hard film;
 varnishes are produced by mixing boiled oils with
resins or gums;
 enamels are varnishes + pigments;
 paints do not contain gums or resins

 Latex paints - alkyd resins which are

manufactured from fatty acids cleaved from
vegetable oils, water soluble
Linoleum and Jojoba

 Made up of Oils + gums + synthetic resins +

pigments;
 oils are "blown" which thickens them and makes them
soluble in petroleum oils (resins)
 linoleum is not used much in U.S. anymore.

 Jojoba - oils is esters rather than triglycerides,

originally thought to be good substitute for
sperm oil but is not because of high temperature
breakdown; however is useful in medicine and
cosmetics.
Extraction

 Grinding with stones

- cold pressing – high quality
 Steam driven stone press
 hot pressing
 Screw press - continuous feed
 Solvent extraction - follows screw press, hexane
Refining

 Removal of free fatty acids

 Degumming - removes mucilaginous material
 Bleaching - removal of pigments
 Deodorized - steam heating
 Winterize - prevents clouding by chilling oil and
filtering out particles.
 Hydrogenation - yields vegetable lards,
margarine and cheese substitutes
Drying Oils
High in double bonds in FA
 Linseed oil - Linum usitatissimum, seeds, water-
repellent glaze
 mostly non-edible oils
 due to unpleasant flavor
 Cyanogenic glycosidesand
 rapid rancidity due to lots of double bonds.
 also source of flax
 Tung oil - Aleurites (Euphorbiaceae), seeds,
poisonous (not edible), used in paints, waterproof
coverings and caulking. Once grown in U.S. but
most now comes from China.
Semi-drying Oil
Few double bonds in FA
 Safflower oil - Carthamus tinctorius, thistles, oil is from seeds, used in cooking oils, salad
dressings, margarine, high I value so low in calories but oxidizes readily
 Produces dye
 Soybean oil – Glycine max already covered, stores well, used in salad and cooking oils and
artificial "fluffy" products.
 Sunflower oil - Helianthus annuus - native North American plant but development of large-headed
cultivars is largely credited to Russians; used as salad and cooking oil; paints, varnishes and resins;
added to diesel fuel.
Considered equal to olive oil, used for production of margarines.
 Corn oil – Zea mays salad dressing and margarines, stable but smokes at high temp.
 Sesame oil - Sesamum indicum, from Ethiopia, highly resistant to oxidation due an antioxidant
compound called sesamolin, most is consumed and produced in Africa, Middle East, India and
China
 Cottonseed oil – Gossypium barbedensis byproduct of cotton fiber production, must remove
gossypol (toxic to most animals except cows); Wesson oil, hydrogenation ---> Crisco
 Rapeseed oil - Brassica napus, edible oil but possibly toxic, most useful as machine oil as an
lubricant
Non-drying Oil

 Peanut oil - Arachis hypogaea, premium cooking

oil
 Olive oil - Olea europea, obtained from fruit
pulp,
 Gentle pressing of the olive – virgin oil
 Further pressing – first, second grade oils
 Has monounsaturated fat – good for health.
 Castor oil - Ricinus communis
 Laxative – ricinoleic acid
 poison - ricine (alkaloid) and ricin (highly toxic
protein); used in soaps, paints, lubricants
Vegetable Fat

 Oil palms - Elaeis guinensis, distinct oils are obtained from

fruit pulp and seeds
 kept separate due to differences in chemical composition; used in
soap, candles, margarine and shortenings
 U.S. diets are avoiding fats and palm oils are taboo.
 Coconut oil - Cocos nucifera, cosmetics and nondairy
"dairy" products
 At 20oC becomes semisolid; at 15oC becomes brittle
 Has free fatty acid – caprylic acid - smell
 Shea butter: Butyrospermum parkit
 50% saturated fat
 Relative effect of fats on Total Cholesterol

Alpha  Delta TC 

Myristic Palmitic Linoleic
Linolenic Dietary Change in
Oil or Fat acid acid acid
Acid Cholesterol cholesterol
C14:0 C16:0 C18:2
C18:3 level

Butterfat 11 27 2 1 273 1788 

Canola oil 0 4 22 10 0 -514 

Coconut oil 18 9 2 0 0 1674 

Corn oil 0 11 58 1 0 -870 

Grape seed oil 0 8 73 0 0 -1196 

Lard 2 26 10 0 77 630 

Olive oil 0 13 10 1 0 88.6 

Safflower oil* 0 7 78 0 0 -1310 

Soybean oil 0 11 54 7 0 -908 

Sunflower oil* 0 7 68 1 0 -1142 

* Not high-oleic
Wax

 Long chain alcohol and long chain fatty acid

 Jojoba wax: Simmondsia chinensis
 Seeds contain liquid wax
 Similar to sperm whale oil
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