tci info sheet

7/27/2019 TCI Info Sheet

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TECHNOLOGYCROPSI N T E R N A T I O N A L

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

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 widerange of high-value oleochemical derivatives, including polymers, polymeradditives, surfactants, personal care products and pharmaceuticals. Higherucic acid rapeseed (HEAR) contains over 50% erucic acid in the seed oiland 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 erucicrapeseed oil (HERO) offers a viable alternative source of long-chainoleochemicals that is both renewable and cost effective.

Erucic acid is described chemically as 13-cis-docosenoic acid or (Z) 13-docosenoicacid and abbreviated to C22:1n-9 using the standard nomenclature.

Commercial Information

Technology Crops International manages the commercial production ofhigh erucic acid rapeseed oil through contract crop production with growersaround the world. The oil is processed to demanding standards to complywith 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, rapeseedis available for farming production in both annual and biennial forms ofthe plant. High erucic rapeseed is just one of several types of rapeseednow grown worldwide. Other main types include Double Low (low inerucic acid and low in glucosinolates) and Triple Low (low in erucic acid,glucosinolates and linolenic acid) varieties.

Geographic DistributionGrown in many countries around the world, the major production areas ofrapeseed include Europe, Canada, China, India and Australia.

Growth Habit

Commercially-grown varieties of rapeseed can grow to a height ofapproximately 3 to 6.5 feet (1 to 2 meters). Each plant has a number offlower-bearing racemes (branches) on which bright-yellow flowers areproduced. These flowers can be self-pollinating, insect pollinated or windpollinated. The plant has a tuberous tap root which helps to make itrelatively drought resistant.


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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 oilcontent of about 40-45%, of which some 50-55% is erucic acid. Modern plant varieties havea very low glucosinolate content, and thus the meal left over after extracting the oil issuitable 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, whilespring-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 specialtychemicals in a wide range of applications. Its greatest single use is in the production ofthe primary amide, erucamide. This derivative is widely used as a surface friction modifieror slip additive in the production of polyethylene and polypropylene film.

Erucic acid is further utilized commercially as a feedstock in the production of secondaryderivatives 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 reactioninitially 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 800to 1600 ppm prior to extrusion into film. This additive dramatically reduces surface frictionand enables the film to be processed at high speeds.

Time after extrusion

CoF

Amide moleculeson film surface





Reaction of erucic acid with fatty amines such as stearyl amine produces a secondaryamide, stearyl erucamide. This amide is used in polymer blends where high processingtemperatures 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 diaminesare used to produce bisamides. These amides are reported to aid in the release of moldedpolymer articles.

Ozonolysis of erucic acid produces brassylic acid and pelargonic acid. Brassylic acid isused 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 bepolymerized or copolymerized to yield polymers useful as flow improvers and pour-pointdepressants 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 fatsubstitutes. Behenic acid esters are poorly absorbed and are not incorporated into bodyfat. Esters produced from behenic acid and polyglycerol are useful as nucleation aids forother vegetable oils.

4. Personal care products

Erucic acid esters and behenic acid esters are widely used as emollients in the formulationof creams and lotions. Behenyl alcohol is a structural component used in deodorantsticks and in cosmetic creams such as the RegeneristTM brand product line from OLAY.

Ethoxylation of behenyl alcohol produces non-ionic surfactants used to generate nano-emulsions used in shampoos. Reaction of behenic acid with functionalized polyaminessuch as dimethylamino-1,3-propanediamine and subsequent quaternization producescationic surfactants used as non-irritating conditioning agents in hair care products.

C21H43CONH(CH2)3 N+(CH3)3Cl

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5. Pharmaceuticals

The highly-purified glyceryl trierucate (GTE), free from very long-chain saturated fattyacids 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 wasultimately fatal. The GTE oil used in combination with glyceryl trioleate is also known asLorenzos oil, named after Lorenzo Odone, the first patient treated with the lipid mixture.





Analyses of high erucic acid rapeseed oil

Fatty acid composition of high erucic acid rapeseed oil

Fatty acid Amount FAME (%)

palmitic acid (C16:0) 2.8

stearic acid (C18:0) 0.7

oleic acid (C18:1n-9) 9.1

linoleic acid (C18:2n-6) 11.5

alpha-linolenic acid (C18:3n-3) 9.8

eicosenoic acid (C20:1n-9) 6.0

erucic acid (C22:1n-9) 53.2

Erucic acid has the chemical structure CH3(CH2)7CH=CH(CH2)11COOH, which can beabbreviated to R-COOH (where R=C21H42). The fatty acid is isolated from HERO byhydrolysis or methanolysis to produce HEAR fatty acids or HEAR methyl esters. Thesemixtures are separated using fractional distillation to yield erucic acid or methyl erucatein high purity.

Conversion of HEAR to its derivatives

HEAR

Erucic acid

behenyl alcoholbehenic acid derivatives

estersesters

amides

amines

salts

quats

amides

esters

salts

epoxides

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