Epoxysuccinic acid

Oxidation. Maleic and fumaric acids are oxidized in aqueous solution by ozone [10028-15-6] (qv) (85). Products of the reaction include glyoxyhc acid [298-12-4], oxalic acid [144-62-7], and formic acid [64-18-6], Catalytic oxidation of aqueous maleic acid occurs with hydrogen peroxide [7722-84-1] in the presence of sodium tungstate(VI) [13472-45-2] (86) and sodium molybdate(VI) [7631-95-0] (87). Both catalyst systems avoid formation of tartaric acid [133-37-9] and produce i j -epoxysuccinic acid [16533-72-5] at pH values above 5. The reaction of maleic anhydride and hydrogen peroxide in an inert solvent (methylene chloride [75-09-2]) gives permaleic acid [4565-24-6], HOOC—CH=CH—CO H (88) which is useful in Baeyer-ViUiger reactions. Both maleate and fumarate [142-42-7] are hydroxylated to tartaric acid using an osmium tetroxide [20816-12-0]/io 2LX.e [15454-31 -6] catalyst system (89). 

Keywords epoxide, tran -epoxysuccinic acid, hydrogenation, hydrogenolysis, alcohol... 

The asymmetric reduction of raeso-epoxides with hydrogen or hydrides has been scarcely explored, despite the synthetic utility of the chiral secondary alcohol products. The lone example has been provided by Chan, who treated the disodium salt of epoxysuccinic acid with H2 or MeOH as the reducing agent in the presence of a chiral rhodium catalyst (Scheme 13) [27]. Deuterium labeling experiments established that the reduction proceeded through direct cleavage of the epoxide C-O bond, rather than isomerization to the ketone followed by carbonyl reduction. 

Packter, N.M. Studies on the Biosynthesis of Phenols in Fungi. Production of 4-Methoxytoluquinol, Epoxysuccinic Acid and a Diacetylenic Alcohol by Surface Cultures of Lentinus degener I.M.I. 110525. Biochem. J. 114, 369 (1969). 

Saturated and unsaturated mono-, di-, and tricarboxylic acids with 2-6 C-atoms carrying hydroxy and carbonyl groups participate in the cycles mentioned above (Fig. 89). The secondary products derived from cycle intermediates are either carboxylic acids, e.g., agaricic acid, epoxysuccinic acid or mesotartaric acid, or lactones like the nonadrides. 

Tricarboxylic acid cycle derivatives irans-Epoxysuccinic acid (D5) Blighting factor in almond leaves, formed after Rhizopus infection of the hulls, which causes overproduction of fumaric acid... 

The hydrolysis of cw-epoxysuccinic acid (the initial product in the hydroxyla-tion reaction of maleic acid by hydrogen peroxide) by H2O2 is accelerated by the epoxidation catalyst sodium tungstate. The reaction is first-order within respect to the concentrations of the catalyst and the epoxide and end-product inhibition was observed. ... 

The double bond in MA and derivatives can be epoxidized to yield epoxysuccinic acid derivatives 92. So far, the primary use of this reaction has been for the synthesis of tartaric acid 93 (R = H). Epoxysuccinic acid can also be made by the hypochlorite reaction of maleic acid. The final product, dl-trans-a,p-epoxysuccinic acid 92 (R = H) is isolated in a 75% yield. 

Epoxysuccinic acid 92 has not found a major outlet but its functionality shows significant potential. 

MA condensations, 500, 516 MA copolymer crosslinked, 273, 444, 449 MA crosslinking, 507-510 MA crosslinking kinetics, 508 MA crosslinking mechanism, 508, 509 MA curing accelerators, 508 MA grafted fiber composites, 473 maleimide modified, 511 a,j3-Epoxysuccinic acid, dl-trans, 69, 73 Equimolar copolymerizations see alternating copolymerization... 

Dicarboxylic acid anhydrides. A soln. of c/5-epoxysuccinic acid in trifluoroacetic anhydride allowed to stand overnight at 22°, then evaporated cw-epoxy-succinic anhydride. Y 85%. Also from the disodium salt s. G. G. Allan and A. N. Neogi, Chem. Ind. 1971, 545. 

Ling ETM, Dibble JT, Houston MR, Lockwood LB, Elliott LP (1978) Accumulation of 1-trans-2,3-epoxysuccinic acid and succinic acid by Paecilomyces varioti. Appl Environ Microbiol 35 1213-1215... 

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