Ester glycidyl

The trialkylacetic acids have a number of uses ia areas such as polymers, pharmaceuticals, agricultural chemicals, cosmetics, and metal-working fluids. Commercially important derivatives of these acids iaclude acid chlorides, peroxyesters, metal salts, vinyl esters, and glycidyl esters. 

Both saturated (50) and unsaturated derivatives (51) are easily accepted by lipases and esterases. Lipase P from Amano resolves azide (52) or naphthyl (53) derivatives with good yields and excellent selectivity. PPL-catalyzed resolution of glycidyl esters (54) is of great synthetic utiUty because it provides an alternative to the Sharpless epoxidation route for the synthesis of P-blockers. The optical purity of glycidyl esters strongly depends on the stmcture of the acyl moiety the hydrolysis of propyl and butyl derivatives of epoxy alcohols results ia esters with ee > 95% (30). 

In addition, glycidyl esters are produced by the reaction of cycloahphatic carboxyUc acids with epichlorohydrin, followed by dehydrohalogenation with caustic. Such products are characterized by low viscosities (ca 500 mPa-s (=cP)). Reactivity of the glycidyl esters more closely resembles the standard bisphenol—epichlorohydrin resins. 

Another example of interest with regard to the reaction mechanism is the analysis of epoxy groups. Durbetaki60 titrated a-epoxy compounds with HBr (cf., p. 260) in glacial acetic acid with crystal violet as indicator, but the method was slow for glycidyl esters, CH2—CHCH2OOCR. As it concerns a two-step... 

Allyl formate, physical properties, 6 292t Allyl glycidyl ester (AGE), physical properties of, 2 244, 246 Allyl glycidyl ether, 2 267-268 Allylic derivatives, hydroboration of, 73 641... 

Methacrylic acid glycidyl ester Methacrylic acid hexyl ester Methacrylic acid methyl ester... 

A trifluoroacetic anhydride-catalysed opening of the oxirane system of glycidyl esters with simultaneous migration of the acyl group provides a new, efficient entry... 

Enantioselective rearrangement of epoxides to allylic alcohols 91TA1. Photochemical reactions of glycidyl esters 92MI11. 

Finally, another useful synthesis of epoxides (in the form of glycidyl esters which are important synthetic intermediates) consisted of treating an a-halo-/Miydroxyester with sodium ethoxide (equation 174)945. 

Initiators. All keto compounds tested were analytically pure. l[2-N-Methylpyrrolyl]2-propanone, a hitherto unknown compound, was synthesized in 20% yield from N-methylpyrrolaldehyde using a Darzens glycidyl ester condensation ... 

Tougher polymers of somewhat lower Tg are obtained from glycidyl esters such as the diglycidyl ester of hexahydrophthalic acid (Araldite CY-184 from Huntsman). The glycidyl esters are prepared by reacting the corresponding cycloaliphatic carboxylic acid with epichlorohydrin and dehydrohalogenat-ing with NaOH. 

The reagent catalyzes the reaction of sodium salts of fatty acids with epichloro-hydrin to form glycidyl esters. Other quaternary ammonium halides are less effective, probably owing to decreased solubility in epichlorohydrin. 

Cadura E Ester [Shell], TM for glycidyl ester of Versatic 911 Acid. 

We then discovered that we could improve the softness and the flow of the binders by incorporating a derivative of a synthetic fatty acid. This derivative is the glycidyl ester of an a-branched monocarboxylic acid with 10 carbon atoms and is commercially available under the trade-name CARDURA. ElO (CE lO). Being a monoepoxy compound, CE 10 could be easily incorporated by reaction with part of the carboxyl groups present in the binders ... 

Indeed, in a patent held by the Dow Chemical Company(1)it is observed that epichlorohydrin (or other suitable 1,2-epoxide) is required in order to obtain high yields of glycidyl esters from 2-hydroxy-3-chlorophenyl esters. A mechanism involving transepoxidation was proposed (Fig. 17). 

The best technique for ring closure evaluated to date involves continuous addition of 50% aqueous sodium hydroxide to the reaction mixture at such a rate that water may be obtained by azeotropic distillation. Although polymeric material is formed during the reaction this can be removed, along with the salt formed during dehydrochlorination, prior to isolation of the glycidyl ester by distillation. 

A variety of cation-induced cyclization approaches to systems of this type have been introduced. Reaction of hydroxyethylthiocyanates (236) with a tertiary alcohol, R OH, in sulfuric acid gives the 2-iminooxathiolanes (237) (Equation (35)) <92Z0R418> and treatment of glycidyl esters such as (238) with cationic zirconium complexes such as (239) and AgC104 gives the dioxolane (240) (Equation... 

Chlorinated and/or oxidized starches crosslinked with glyoxal were used to produce a high-strength size for paper.573 Coating adhesives were also prepared by crosslinking glycidyl esters.1385 In addition, esters of starch with inorganic acids (such as starch phosphates) were crosslinked with various aliphatic and aromatic aldehydes in the presence of urea, melamine and similar compounds.1322... 

Aserin,A.,N. Garti,and Y. Sasson, Preparation of Monoglycerides of Fatty Acids from Epichlorohydrin by Phase Transfer Catalysis. Glycidyl Esters, 7 d. /ig. Chem. Prod 23,452 (1984). 

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