Linoleic acid ethyl ester

A large number of heterogeneous catalysts have been tested under screening conditions (reaction parameters 60 °C, linoleic acid ethyl ester at an LHSV of 30 L/h, and a fixed carbon dioxide and hydrogen flow) to identify a suitable fixed-bed catalyst. We investigated a number of catalyst parameters such as palladium and platinum as precious metal (both in the form of supported metal and as immobilized metal complex catalysts), precious-metal content, precious-metal distribution (egg shell vs. uniform distribution), catalyst particle size, and different supports (activated carbon, alumina, Deloxan , silica, and titania). We found that Deloxan-supported precious-metal catalysts are at least two times more active than traditional supported precious-metal fixed-bed catalysts at a comparable particle size and precious-metal content. Experimental results are shown in Table 14.1 for supported palladium catalysts. The Deloxan-supported catalysts also led to superior linoleate selectivity and a lower cis/trans isomerization rate was found. The explanation for the superior behavior of Deloxan-supported precious-metal catalysts can be found in their unique chemical and physical properties—for example, high pore volume and specific surface area in combination with a meso- and macro-pore-size distribution, which is especially attractive for catalytic reactions (Wieland and Panster, 1995). The majority of our work has therefore focused on Deloxan-supported precious-metal catalysts. 

Synonyms linoleic acid ethyl ester 9,12-octadecadienoic acid ethyl ester vitamin E... 

CAS 544-35-4 EINECS/ELINCS 208-868-4 Synonyms Ethyl (Z,Z)-9,12-octadecadienoate Linoleic acid ethyl ester 9,12-Octadecadienoic acid ethyl ester Vitamin F Definition Ester of ethyl alcohol and linoleic acid Empirical C20H36O2... 

Arai, M., Fukuda, H. and Morikawa, H. (1987) Selective separation of gamma linoleic acid ethyl ester using Y-zeolite. J. Ferment. Technol. 65, 569-574. 

In the presence of a catalytic amount of Sc(OTf)3, conjugated linoleic acid ethyl ester could be used as a diene in Diels-Alder reactions to react with quinines, a,P-unsaturated aldehydes, and ketones in good yields [26]. Sc(OTf)3 catalyst could be recovered by extraction of organic layers with water. After removal of water, the recovered Sc(OTf)3 could be reused in the Diels-Alder reaction without appreciable loss of catalytic activity. 

Trade Names Crossential L90 Emerso 315 Pamolyn 200 Pamolyn 240 9,12-Linoleic acid. See Linoleic acid Linoleic acid diethanolamide. See Linoleamide DEA Linoleic acid ethyl ester. See Ethyl linoleate Linoleic acid methyl ester. See Methyl linoleate Linoleic diethanolamide. See Linoleamide DEA Linolenic acid... 

Acetic acid, butyl ester Acetic acid, pentyl ester Acetic acid, decyl ester Acetic acid, benzyl ester Acetic acid, benzyl ester Acetic acid, 1-cyclohexenyl ester Acetic acid, 3-cyclohexenyl ester Butyric acid, benzyl ester Phenylacetic acid, propyl ester Oleic acid, methyl ester Linoleic acid, methyl ester Linolenic acid, methyl ester Adipic acid, methyl ester Adipic acid, ethyl ester Adipic acid, diethyl ester Adipic acid, dipropyl ester Adipic acid, (methylethyl)ester Adipic acid,... 

Ethyl linoleate 9,12-Octadecanoic acid ethyl ester 544-35-4... 

FIGURE 1.21 Effect of initial molar ratio of various fatty acid esters to a-CD on the inclusion fraction of fatty acid esters in a-CD. O CAPME, A CPRME, MYRME, <> LINME, V EPAEE, DHAEE. Abbreviations CAPME, -caproic acid methyl ester CPRME, n-caprylic acid methyl ester LINME, linoleic acid methyl ester EPAEE, ethyl eicosapentae-noate DHAEE, ethyl docosahexaenoate. (From Yoshii, H. et ah, Oyo Toshitsu Kagaku, 42, 243, 1995. With permission.)... 

Abbreviations PC, phosphatidylcholine FFA, free fatty acid EPA, eicosapentaenoic acid DHA, docosahexaenoic acid EPA-EE, eicosapentaenoic acid ethyl ester DHA-EE, docosahexaenoic acid ethyl ester CLA, conjugated linoleic acid,. 

Linoieic acid ethyl ester. See Ethyl linoleate Linoleic acid, monoester with 1,2-propanediol. See Propylene glycol linoleate Linoleic acid, oleyl ester. See Oieyi linoleate Linoleic acid, 1,2,3-propanethyi ester. See Trilinolein... 

Octadecadienoic acid ethyl ester. See Ethyl linoleate... 

C12 to C20, primarily Ci6 to ( is), used as surface lubricants in the manufacture of food-contact articles. The method, which uses ethyl palmitate (Eastman Chemicals No. 1575 Red Label) as an internal standard, has been validated at 200 ppm total FAME [185]. Other FAME standards (methyl palmitate, methyl stearate, methyl oleate, methyl linoleate and methyl linolenate) are available (Applied Science Laboratories) [116], Worked out examples of additive determinations are given in the Food Additives Analytical Manual [116], which also describes a great many of indirect food additives, such as BHA, BHT, TBHQ, l-chloro-2-propanol, DLTDP, fatty acid methyl esters, w-heptyl-p-hydroxybenzoate, propyl-gallate, sodium benzoate, sodium stearoyl-2-lactylate, sorbitol and phenolic antioxidants. EPA methods 606 and 8060 describe the CGC separation of phthalate esters (direct injection) (cf. Figure 4.2). 

The flavour of distillates from apple and pear is characterised by typical aroma compounds from these fruits formed by enzymatic degradation of fatty acids to C6-fragments like hexanol, trans-2-hexenol, as well as ethyl esters and acetates of hexanoic acid. In distillates of pears, especially of the variety Bartlett pear, the characteristic pear flavour is mainly dominated by the ethyl and methyl esters of frans-2-czs-4-decadienoic acid and trans-2-trans-A-decadienoic acid [27-29], The biogenesis of these monounsaturated, diunsaturated, and triunsaturated esters may be explained by -oxidation of unsaturated linoleic and linolenic acid in the fruits. The sesquiterpene compound a-farnesene, which is formed during postharvest ripening and storage of Bartlett pears [28], shows that quality and intensity of distilled pear spirits is mainly influenced by the quality and degree of ripeness of the fruits. 

A significant portion of the neutral ethyl ether extract from the salts of carboxylated methyl linoleate consists of ,/3-unsaturated cyclic ketones. This material is produced in small but significant amounts (4-10%) (Table I) from the carboxylation of polyunsaturates but not from the corresponding monounsaturated fatty acids and esters (19). These ,/ -unsaturated cyclic ketones were identified spectroscopically (IR, UV, and NMR) as 4. This structural assignment was firmly established by mass spectral analyses before and after hydrogenation of the carbon-carbon double bond. 

The catalyst system [Rh(acac)(CO)2]/biphephos shows high activity for isomerization with yields of 60% of branched isomers at 20 bar CO/H2 pressure and 115°C [10]. With this catalyst system, a 26% selectivity of linear aldehyde from ethyl oleate was observed. The selectivity for the n-aldehvde was higher at 34% for linoleic acid. A hydrogenation side product was observed in the reaction due to the isomerization of the double bond toward the ester group, where hydrogenation is favored. 

A very different type of reaction is represented by the conjugation of xenobiotic alcohols with fatty acids, yielding highly lipophilic metabolites accumulating in tissues. Thus, ethanol and haloethanols form esters with palmitic acid, oleic acid, linoleic acid, and lin-olenic acid enzymes catalyzing such reactions are cholesteryl ester synthase (EC 3.1.1.13) and fatty-acyl-ethyl-ester synthase (EC 3.1.1.67) (71). Larger xenobiotics such as tet-rahydrocannabinols and codeine are also acy-... 

Fats and oils (triglycerides) from plants and animals are renewable sources of chemicals, but the amounts of the chemicals made from them are small compared with those made from petroleum and natural gas. This may change if biodiesel fuel (e.g., ethyl oleate) made by the alcoholysis of oils becomes common. Such esters may be useful as environmentally friendly solvents.50 Unsaturated oils, such as linseed oil, are the basis of oil-based paints, which cure by cross-linking through oxidation by air. Soaps are the potassium or sodium salts of the long-chain fatty acids obtained by the hydrolysis of the triglycerides. The dibasic dimer fatty acids obtained by the dimerization of oleic and linoleic acids (both Cig acids) are made into oligomeric fatty amides which are used to cure epoxy resins. The un-... 

Laurie acid, myristic acid, caproic acid Oleic acid, linoleic acid, linolenic acid Methyl or ethyl esters of lauric acid, myristic acid, oleic acid... 

When samples of the ethyl esters of linoleic and linolenic acids were tested at the 1.6 % level in a vitamin E-free diet with low selenium content, both these fatty acids produced exudative diathesis and gave rise to formation of peroxides in the affected fat tissue, but only linoleic acid produced encephalomalacia. This experiment has been repeated many times with diets containing added selenium so that the exudative diathesis was suppressed. In these cases encephalomalacia was the only symptom it occurred only with linoleic acid, not with linolenic acid. The samples of linolenate tested contained a certain amount of trans-isomers it is not known whether the presence of these isomers played a role in preventii encephalomalacia. It is clear, however, that whereas the acceleration of exudative diathesis is related to polyunsaturation of the dietary fatty acids, the production of encephalomalacia is a more complicated matter depending on the structure of the polyunsaturated fatty acid (Dam et aL., 1958b). 

Recently, a proprietary method has been developed that quantitatively isomerizes methyl esters and ethyl esters of linoleic acid using very low quantities of catalysts and virtually no solvents (data not published). Because of the quantity of catalyst (-2%), only a small fraction of the ester is saponified and hence appears as free fatty acid after addition of a neutralizing agent. Most of the product (>92%) is still in the form of the methyl or ethyl ester after the isomerization process. The reaction proceeds at temperatures dovra to below 100°C, and the CLA product is characterized by very low levels of CLA isomers produced by thermal [1,5] sigmatropic rearrangements (see below). 

CLA was more stable than linoleic acid as free fatty acids, and less stable as ethyl esters (18). Another study using methyl esters reported that stability decreased in the following order oleate > CLA > linoleate. Samples were stored in the dark at 40°C and monitored by thin-layer chromatography (TLC), GC and PV. From 9-cis,li-trans, the major monohydroperoxides formed were identified as 8-, 9-, 12-and 13-monohydroperoxides, whereas 10-trans,12-cis yielded primarily 9-, 10-, 13-, and 14-monohydroperoxides (19). 

The alcohols above ethyl in the series are generally spoken of as higher alcohols. An extensive literature on their presence in brandy has developed because of their importance to the organoleptic character of brandy. Much less information is available for wines. The chief higher alcohols found are isoamyl (3-methyl-l-butanol), active amyl ((—)-2-methyl-l-butanol), -propyl (1-propanol), isobutyl (2-methyl-l-propa-nol), n-butyl (1-butanol), and (—) sec-butyl (2-butanol). Others doubtless occur and will be identified as better methods for their separation are developed. Buscarfins (1941) fractionated (under vacuum) a fusel oil from wine pomace and identified amyl, propyl, isobutyl, butyl, and isopropyl (2-propanol)alcohols as esters and higher alcohols up to decyl. No hi er secondary alcohols were found. The residue consisted of esters, fatty acids, furfural, cylic bases, and hydrocarbons. Only acids with an even number of carbon atoms were demonstrated. The unsaturated acids oleic and linoleic were present in small amounts, presumably from the seeds. Ethyl esters were more important in amount than amyl esters. There was 3% furfural, 5.5% fatty acids (free and esterified), 30.9% alcohols (free and esterified), and 1.6% hydrocarbons (terpene). Dupont and Dulou (1935) demonstrated sec-butyl alcohol in a technical propyl alcohol that had been produced from fusel oil. 

Fruits obtained from this species of palm are very rich in fats, including oleic, lauric, myristic, capric, palmitic, stearic (all saturated) and linoleic fatty acids as well as ethyl esters of these fatty acids. The lipophilic constituents also include numerous sterols, diterpenes, sesquiterpenes, triterpenes, carotenoids and high-molecular-weight alcohols (Winston 1999). Water-soluble polysaccharides with high molecular weights are also found in the seed, but not in the widely used liposterolic extracts. 

It is clear that moulds represent excellent sources of dietetically acceptable oils. The main difficulty is one of sales and marketing as it obviously is not easy to convince a suspicious public that mould oil is as good as a plant oil. Scientifically, there is no detriment to using mould oil. Indeed one positive advantage of the mould oil as a source of GLA is its much lower content of linoleic acid (18 2) than either of the plant sources. This makes the purification of GLA much easier than starting from the plant oils as the main problem is the separation of the two closely allied fatty acids. Simple urea adduct formation enables oils with 80-85% GLA to be produced. Solvent winterization has also been used but without great effect (Yokochi et al., 1990) although the best, but most expensive, procedure for purification is by use of zeolites where 98% pure GLA has been obtained as its ethyl ester (Arai et al., 1987). Enrichment... 

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