Fatty oxirane

An interesting ring opening of a fatty oxirane has been reported by Loupy [69]. Diethyl acetamidomalonate opens the oxirane ring according to Scheme 8.47. 

Epoxides (oxirans) and 1,2-diols can also be looked upon as disguised ketones capable of being unmasked by acids. Since its development by Spencer et al49 the idea has been utilized by several other groups who used protic acids in work aimed at syntheses of methyl lambertianate,50 a rare furanoid fatty acid from an Exocarpus species,51 and a terpenoid furan,... 

In contrast to the relative chemical stability of mono-epoxides, diol epoxides of fatty acids (10.52), which are formed from di-epoxides by EH, are subject to a different fate. In such metabolites, intramolecular nucleophilic substitution may occur, such that oxirane opening is accompanied by formation of a tetrahydrofuran ring [134], Such reactions of intramolecular nucleophilic substitution are discussed in detail in Sect. 11.9. In the case of diol epoxides of fatty acids, the resulting tetrahydrofuran-diols (10.53) are part of a much larger ensemble of oxygenated metabolites of fatty acids, the potential cytotoxicities of which are being evaluated [135]. 

The other mode of activation of the oxirane moieties is through cationic polymerization, which will generate a network for polyfunctional epoxidized glycerides and thermoplastic materials with fatty acids bearing a single epoxy group [43],... 

Cross-linkers that are based on epoxidized fatty acid derivatives seem to offer a good alternative for TGIC. In a recent patent, DSM Resins BV has claimed the use of aliphatic oxiranes based on vegetable oils as cross-linkers in commercial powder... 

On a pilot scale, epoxidation of both rapeseed mefliyl esters (RME) and higholeic sunflower methyl esters (HOSME) generally yields 85-90%. Epoxidized RME have oxirane values ranging from 4.5 to 5.2 and iodine values ranging from 5 to 1.7. Epoxidized HOSME have oxirane values ranging from 4.5 to 5 and iodine values ranging from of 1.7 to 0. The fatty acid compositions of expoxidized methyl esters determined by GC are given in Table 5. 

With heptanol as reactant, the use of PTSA (100°C, 12 h, 1 bar) led to fatty ethers with an oxirane value of 0.0 and a saponifieation value of 130. The main component was the methyl heptyloxyhydroxystearate formed out of the epoxidized oleic methyl... 

Wolf, H.P.O. Engel, D.W. (1985) Eur. J. Biochem. 146, 359-363. Decrease of fatty acid oxidation, keto-genesis, and gluconeogenesis in isolated perfused rat liver by phenylalkyl oxirane carboxylate (B 807-27) due to inhibition of CPT-1 (EC 2.3.1.21). 

CAS 52932-31-7 25212-19-5 Synonyms Adipic acid, diethylenetriamine, epichlorohydrin polymer Adipic acid, diethylenetriamine, epichlorohydrin resin Diethylenetriamine, epichlorohydrin, adipic acid polymer Epichlorohydrin, adipic acid, diethylenetriamine polymer Hexanedioic acid, polymer with N-(2-aminoethyl)-1,2-ethanediamine and (chloromethyl) oxirane Classification Condensation polymer Uses Antistat, film-former in cosmetics hair care resin in permanent sol ns. and hair sprays dye fixing agent in paper/paperboard in contact with aq./fatty foods Regulatory FDA 21CFR 176.170 Trade Name Synonyms Delsette 101 t[Hercules http //www.herc.com], Hercosett 57 [Hercules http //www.herc.com]... 

Exceptions to the generality of straight chains are FAs substituted with hydroxy, keto (0x0), and epoxy (oxirane) groups and FAs with unusual unsaturation. Methyl branched FAs occur mainly in bacteria, but also naturally in the fat of ruminant animals together with a series of odd-chain fatty acids. 

Conversion of internal unsaturations in triglycerides and their fatty acids into epoxide moieties has been optimised to enable their industrial implementation an economically viable operation with some oils. This strategy has opened the way to elaboration of macromolecular materials that could become real commodities. This rationale implies that the performance of these polymers should adequately match the respective applications they are conceived to fulfill. Apart from such common epoxidised oils, this section deals with other more elaborate monomers in which the oxirane function is present as an end group and hence more reactive. 

Classical combination of diepoxide monomers with diamine counterparts in conventional Araldite-type adhesives involves terminal oxirane groups, which are considerably more reactive than the internal counterparts present in epoxidised oils or fatty acids. This difference is probably why studies on the potential of coupling epoxidised oils and diamine for the development of epoxy resins based on renewable resources have been published. 

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