Nonedible Byproducts

The majority of rapeseed currently grown in Canada is canola, although there still remains some acreage devoted to HEAR. This is due to the industrial applications of er-ucic acid and its cleavage products.

Canola Oil

Canola oil-based printing ink has been found to be superior to petroleum-based ink by reducing the rub problem. Switching to canola-based ink also reduces environmental problems, as 75% of the ink is biodegradable (78). The superior rub properties of canola oil permit both black and color inks to be made with this oil. A number of major Canadian newspapers are now printed with canola oil-based ink.

High Erucic Acid Oil

Erucic acid, a long chain fatty acid (C22:i) containing a single double bond, exhibits high fire and smoke points (271°C). These properties allow erucic acid to withstand high temperatures and still remain a liquid at room temperature (79). Consequently, oils containing high levels of erucic acid are used as lubricants or in lubricant formulations (80). Because of their lubricant properties, HEAR oils have found applications as spinning lubricants in the textile, steel, and shipping industries, as drilling oils, and as marine lubricants (81). High erucic acid oil has also been used for the clinical treatment of adrenoleukodistrophy, a rare children's disease. Hydrogenated HEAR oils have industrial applications by producing hard, glossy waxes (82).

Erucic Acid Derivatives

Erucic acid and its hydrogenated derivative, behenic acid, and erucyl and behenyl alcohols as well as other derivatives including esters, amides, amines, and their salts are used extensively in industry as slip, softening, antifoam-ing, and release agents; emulsifiers; processing aids; conditioners; antistatic agents; stabilizers; and corrosion inhibitors (80).

CH3(CH2)7CH = CH(CH2)nCOOH erucic acid

CH3(CH2)7CH2CH2(CH2)uCOOH behenic acid

Erucamide, the amide derivative of erucic acid, has been used for many years as a processing aid and antiblock agent in plastic films. It facilitates the production of plastic parts by acting as a lubricant and forming a thin layer on the surface of the plastic, thus preventing the sheets from sticking to each other.

CH3(CH2)CH = CH(CH2)nCONH2 erucamide

Behenic acid and its esters are used to enhance the performance of a wide range of pharmaceutical, cosmetic, fabric softener, and hair conditioner products. As antifriction coatings they soften and improve the texture and sewabil-ity of cotton and synthetic fabrics (80). In addition to the compounds discussed, there are a large number of HEAR oil-derived alcohols and esters that are used in the cosmetic and pharmaceutical industries.

Erucic acid cleavage products have considerable potential in the production of plastics, resins, and nylons. For example, the oxidative cleavage of erucic acid yields bras-sylic acid, a 13-carbon dicarboxylic acid, and pelargonic acid, a 9-carbon monocarboxylic acid. A number of long chain nylons prepared from brassylic acid are important in automotive parts and products (79, 83,84).

CH3(CH2)6CH= CH(CH2)nCOOH oxidative cleavage

- CH3(CH2)yCOOH + HOOC(CH2)uCOOH pelargonic acid brassylic acid

Alkyl esters of brassylic acid are excellent plasticizers. The corresponding allyl and vinyl esters form polymers and copolymers that may be used in molding compounds, reinforced plastics, laminates, sealants, and coatings (8588).

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