Erucic acid derivative

Ferulic acid, a phenolic acid that can be found in rapeseed cake, has been used in the synthesis of monomers for ADMET homo- and copolymerization with fatty acid-based a,co-dienes [139]. Homopolymerizations were performed in the presence of several ruthenium-based olefin metathesis catalysts (1 mol% and 80°C), although only C5, the Zhan catalyst, and catalyst M5i of the company Umicore were able to produce oligomers with Tgs around 7°C. The comonomers were prepared by epoxidation of methyl oleate and erucate followed by simultaneous ring opening and transesterification with allyl alcohol. Best results for the copolymerizations were obtained with the erucic acid-derived monomer, reaching a crystalline polymer (Tm — 24.9°C) with molecular weight over 13 kDa. 

Rapeseed oil has been used for a number of years in food applications as a cheap alternative to olive oil. However, there are large amounts of etude acid and glucosinolates in conventional rapeseed oil, both substances being toxic to humans and animals. Canola oil derived from genetically selected rapeseed plants that are low in erucic acid content has been developed to overcome this problem. 

Derivation By treating erucic acid with nitrous acid... 

The main derivative of erucic acid is erucamide (2,4). Erucamide is manufactured under standard amination procedures by reacting pure erucic acid ( 95%) at elevated temperature and pressure with ammonia (Scheme 1). The A,A-disubstituted amides are used as slip and antiblocking agents in polyethylene, polypropylene, and other plastics (2,5). The length of the alkyl chain appears to be the key feature for its properties, allowing low concentrations (1000 ppm) in the resin, whereas shorter... 

Behenic acid, its esters, and other derivatives that are derived from catalytie hydrogenation of erucic acid are useful in a wide range of applications including cosmetics, fabric softeners, photothermography, mold release in rubber and plastics, and antifriction coatings in textiles (2). 

Brassylic acid, a 13-caihon saturated dibasic acid, can be derived from the oxidative cleavage of erucic acid and used as a feedstock for the production of nylon (Scheme 1). Brassylic acid is made by ozonolytic cleavage of erucic acid in acetic acid followed by oxidation of the resultant aldehyde by oxygen at elevated temperatures (100°C) to give the diacid. Crystallization from toluene gives a polymer-grade brassylic acid (6). Pilot-scale production of nylon-1313 (7) as well as nylon-613 was found to have exceptionally low sensitivity to moisture, excellent dimensional stability. and dielectric properties. Long-chain nylons of this type have found niche markets in automotive parts. 

Canadian rapeseed oil for edible use is now called canola oil, which is derived from rapeseed low in both erucic acid and glucosinolates. A second oil which is high in erucic acid is produced in limited quantities for industrial use only, and is marketed separately from the edible oils. In the Orient, rapeseed and mustard oils, which are both high in erucic acid, are used extensively for food. Mustard [B. juncea (L.)] is grown and processed for oil in the same manner as rapeseed. 

Rapeseed meal is a by-product of the production of rapeseed oil. In the past, in the Orient the meal was used principally as a fertilizer with limited amounts fed to animals. In Canada and Europe, the meal was fed to livestock but with severe restrictions on its use because of its antinutritional (goitrogenic) effects in animals. Since 1974, however, with the availability of low glucosinolate low erucic acid rapeseed (double low) in Canada (i.e., canola), the production and use of the meal has increased substantially. The same trend is now occurring in Europe with the availability of double low rapeseed. The meal derived from these two types of rapeseed, i.e., high and low in glucosinolates, is handled separately in commerce. 

In the Orient, both rapeseed and mustard oils are used extensively for food and large quantities of mustard are produced for oil in India, Pakistan and Bangladesh. In Canada and Europe there is no production of mustard oil for edible oil purposes. All edible Canadian rapeseed oil is now from canola varieties, i.e., derived from seed low in erucic acid and low in glucosino-lates. High erucic acid rapeseed oil is used exclusively for industrial purposes, such as lubricants, slip agents for molds, and polymers. In Canada these high erucic acid oils are produced and marketed separately from canola oil. Rapeseed oils in the Western World are either very low in erucic acid for edible use or very high (over 40%) in erucic acid for industrial use. 

Cooperative research on many aspects of rapeseed processing and utilization has resulted in rapeseed oil (now termed canola oil) becoming the most widely used edible oil in the domestic market in Canada. Canola oil is the oil derived from the rapeseed varieties grown in Canada which are low in erucic acid and low in glucosinolates. 

DESCRIPTION Low erucic acid rapeseed oil (synonyms low erucic acid turnip rape oil low erucic acid colza oil) is produced from the low erucic acid oil-bearing seeds of varieties derived from the Brassica napus L., Brassica campestris L. species. 

The magnitude of the variation in the composition of rapeseed oil and meal now commercially available has created a need for new terms to describe the products derived from rapeseed. The fatty acid composition of most edible vegetable oils such as soybean, sunflower, or cottonseed oils, varies within narrow limits. Thus, the species or commodity name (e.g., soybean oil) provides a reasonable description of the fatty add composition of soybean oil. In contrast, the erucic acid content of commercially available rapeseed oil may vary from near zero to 55%, and the oleic acid from 10 to more than 60%. A number of terms have been proposed or utilized to describe the new rapeseed oil whose fatty acid composition has been altered by the elimination of erucic acid these include low erucic acid rape-seed oil (LEAR), canbra, and canola. Similar terms such as high erucic acid rapeseed oil (HEAR) and common or traditional rapeseed oil have been used to describe rapeseed oil whose fatty acid composition includes substantial amounts of erucic acid. 

It was more difficult to develop low erucic acid cultivars for northern Europe because most of the rapeseed in this area is derived from winter rape. European cultivars were highly developed for seed and oil yield more time was required to grow a plant from seed to maturity because a cold treatment (vernalization) was required so that the plant could proceed from vegetative to reproductive development. Furthermore, a characteristic had to be transferred from summer rape to winter rape, a cross that produces a... 

Rapeseed oil constitutes a substantial proportion of the supply of edible oil to consumers in many parts of the world. It includes the original HEAR (high erucic acid rapeseed) oils, LEAR (low erucic acid rapeseed) oils and canola oils (canola is the name adopted by Canadians for the oil derived from the new rapeseed low in both erucic acid and glucosinolates). Since there are great differences in the kinds of edible oil products which these consumers prefer, the type and degree of processing that are applied to the oils vary markedly from country to country, and even within different regions of some countries. 

The two most common naturally occurring c/s docosenoic acids are erucic acid (c/s 22 1 n-9) found in the seed oil of the Brassica family and ceto-leic acid (c/s 22 1 n-11) found mainly in marine oils (Ackman et ai, 1971a). The cetoleic acid in fish oils is derived by oxidation of the corresponding alcohol present in small Crustacea which form part of the food chain for marine life (Nenenzel, 1970 Pascal and Ackman, 1976). To date, no longterm studies have been reported in which these two docosenoic fatty acids were fed in purified form. When a comparison was made between a HEAR... 

Hexamethylene diamine can be produced by various processes (see also Chapter 24), and is industrially mostly produced from adipic acid, butadiene, or acrylonitrile. Sebacic acid is obtained from castor oil. Because of the uncertain supply situation, the sebacic acid for such polyamides is being increasingly replaced by dodecane diacid, which is obtained by the oxidation of cyclododecatriene, the cyclic trimer of butadiene. The monomers for polyamide 13,13 are derived from erucic acid (see also Chapter 24). 

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