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HIGH ERUCIC ACID RAPESEED OIL

A cost-effective renewable source for long-chain oleochemicals
An important raw material, erucic acid is used in the production of a wide range of high-value oleochemical derivatives, including polymers, polymer additives, surfactants, personal care products and pharmaceuticals. High erucic acid rapeseed (HEAR) contains over 50% erucic acid in the seed oil and is the most economical source of this long-chain fatty acid. While the production of petrochemicals derived from fossil fuels has been adversely affected by rising costs and uncertain supplies, high erucic rapeseed oil (HERO) offers a viable alternative source of long-chain oleochemicals that is both renewable and cost effective. Erucic acid is described chemically as 13-cis-docosenoic acid or (Z) 13-docosenoic acid and abbreviated to C22:1n-9 using the standard nomenclature. Commercial Information Technology Crops International manages the commercial production of high erucic acid rapeseed oil through contract crop production with growers around the world. The oil is processed to demanding standards to comply with Technology Crops proprietary Crop Assured 365 system of quality control and traceability protocols. For information on availability and pricing of high erucic acid rapeseed oil, contact Technology Crops International at (877) 780-5882. Botanical Information Developed by plant breeders from the weed Brassica napus, rapeseed is available for farming production in both annual and biennial forms of the plant. High erucic rapeseed is just one of several types of rapeseed now grown worldwide. Other main types include Double Low (low in erucic acid and low in glucosinolates) and Triple Low (low in erucic acid, glucosinolates and linolenic acid) varieties. Geographic Distribution Grown in many countries around the world, the major production areas of rapeseed include Europe, Canada, China, India and Australia. Growth Habit Commercially-grown varieties of rapeseed can grow to a height of approximately 3 to 6.5 feet (1 to 2 meters). Each plant has a number of flower-bearing racemes (branches) on which bright-yellow flowers are produced. These flowers can be self-pollinating, insect pollinated or wind pollinated. The plant has a tuberous tap root which helps to make it relatively drought resistant.
USA Office: Technology Crops International . PO Box 11925 . Winston-Salem, NC 27116, USA . +1 877 780 5882 UK Office: Technology Crops Limited . Berewyk Hall Court . Bures Road . White Colne . Colchester, Essex CO6 2QB, UK . +44 (0) 1787 223196

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Seed Characteristics The seed is small, approximately 3/8 to 3/4 inch long (1 to 2 mm), and has an overall oil content of about 40-45%, of which some 50-55% is erucic acid. Modern plant varieties have a very low glucosinolate content, and thus the meal left over after extracting the oil is suitable for use as an animal feed. Agronomic Information Crops may be either autumn- or spring-sown, depending on the variety. Yield Autumn-sown crops of high erucic rapeseed can yield up to 2 tons per acre of seed, while spring-sown crops yield approximately 1 ton per acre. Application areas for high erucic acid rapeseed The value of erucic acid resides in the large number of derivatives used as specialty chemicals in a wide range of applications. Its greatest single use is in the production of the primary amide, erucamide. This derivative is widely used as a surface friction modifier or slip additive in the production of polyethylene and polypropylene film. Erucic acid is further utilized commercially as a feedstock in the production of secondary derivatives such as behenyl alcohol, behenic acid and behenyl amines.

Application areas for erucic acid and its derivatives

1. Polymers and polymer additives The primary use for erucic acid is in the manufacture of erucamide, which is produced by the reaction of erucic acid (or methyl erucate) with ammonia. The chemical reaction initially produces ammonium salt, which is converted to the amide upon heating: CH3(CH2)7CH=CH(CH2)11COOH CH3(CH2)7CH=CH(CH2)11CONH2

Erucamide is added to polyolefins such as polyethylene or polypropylene at between 800 to 1600 ppm prior to extrusion into film. This additive dramatically reduces surface friction and enables the film to be processed at high speeds.

CoF

Time after extrusion Amide molecules on film surface

USA Office: Technology Crops International . PO Box 11925 . Winston-Salem, NC 27116, USA . +1 877 780 5882 UK Office: Technology Crops Limited . Berewyk Hall Court . Bures Road . White Colne . Colchester, Essex CO6 2QB, UK . +44 (0) 1787 223196

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HIGH ERUCIC ACID RAPESEED OIL

Reaction of erucic acid with fatty amines such as stearyl amine produces a secondary amide, stearyl erucamide. This amide is used in polymer blends where high processing temperatures are employed: stearyl erucamide: CH3(CH2)7CH=CH(CH2)11CO-NH-C18H37

Other amides have been produced from erucic acid. For example, erucic acid and diamines are used to produce bisamides. These amides are reported to aid in the release of molded polymer articles. Ozonolysis of erucic acid produces brassylic acid and pelargonic acid. Brassylic acid is used in the manufacture of Nylon 1313 by reaction with 1,13-diamino-tridecane. 2. Petroleum additives Behenyl alcohol, produced from erucic acid, can be esterified with unsaturated acids such as fumaric acid, to yield a polymerizable monomer, behenyl fumarate. This monomer can be polymerized or copolymerized to yield polymers useful as flow improvers and pour-point depressants for use in waxy crude oils. 3. Foods Structured triglycerides from behenic acid, produced from erucic acid by hydrogenation, capric acid and other medium chain fatty acids have been used as low-calorie fats or fat substitutes. Behenic acid esters are poorly absorbed and are not incorporated into body fat. Esters produced from behenic acid and polyglycerol are useful as nucleation aids for other vegetable oils. 4. Personal care products Erucic acid esters and behenic acid esters are widely used as emollients in the formulation of creams and lotions. Behenyl alcohol is a structural component used in deodorant sticks and in cosmetic creams such as the RegeneristTM brand product line from OLAY. Ethoxylation of behenyl alcohol produces non-ionic surfactants used to generate nanoemulsions used in shampoos. Reaction of behenic acid with functionalized polyamines such as dimethylamino-1,3-propanediamine and subsequent quaternization produces cationic surfactants used as non-irritating conditioning agents in hair care products. C21H43CONH(CH2)3 N+(CH3)3Cl 5. Pharmaceuticals The highly-purified glyceryl trierucate (GTE), free from very long-chain saturated fatty acids such as lignoceric acid, has been used successfully to treat adrenoleukodystrophy (ALD). ALD is a genetic disorder affecting young boys. Prior to the use of GTE, ALD was ultimately fatal. The GTE oil used in combination with glyceryl trioleate is also known as Lorenzos oil, named after Lorenzo Odone, the first patient treated with the lipid mixture.

USA Office: Technology Crops International . PO Box 11925 . Winston-Salem, NC 27116, USA . +1 877 780 5882 UK Office: Technology Crops Limited . Berewyk Hall Court . Bures Road . White Colne . Colchester, Essex CO6 2QB, UK . +44 (0) 1787 223196

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Analyses of high erucic acid rapeseed oil
Fatty acid composition of high erucic acid rapeseed oil Fatty acid palmitic acid (C16:0) stearic acid (C18:0) oleic acid (C18:1n-9) linoleic acid (C18:2n-6) alpha-linolenic acid (C18:3n-3) eicosenoic acid (C20:1n-9) erucic acid (C22:1n-9) Amount FAME (%) 2.8 0.7 9.1 11.5 9.8 6.0 53.2

Erucic acid has the chemical structure CH3(CH2)7CH=CH(CH2)11COOH, which can be abbreviated to R-COOH (where R=C21H42). The fatty acid is isolated from HERO by hydrolysis or methanolysis to produce HEAR fatty acids or HEAR methyl esters. These mixtures are separated using fractional distillation to yield erucic acid or methyl erucate in high purity.

Conversion of HEAR to its derivatives

HEAR
Erucic acid behenic acid esters amides amines salts quats behenyl alcohol esters derivatives amides esters salts epoxides

USA Office: Technology Crops International . PO Box 11925 . Winston-Salem, NC 27116, USA . +1 877 780 5882 UK Office: Technology Crops Limited . Berewyk Hall Court . Bures Road . White Colne . Colchester, Essex CO6 2QB, UK . +44 (0) 1787 223196

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