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Isomerization of Maleic Acid to Fumaric Acid Catalyzed by Bromate Ion and Bromine
Author(s) -
Chen YihHsiung,
Jwo JingJer
Publication year - 1983
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198300007
Subject(s) - chemistry , isomerization , bromate , fumaric acid , maleic acid , cumene , sulfuric acid , yield (engineering) , catalysis , photochemistry , iodide , inorganic chemistry , bromine , organic chemistry , bromide , copolymer , polymer , materials science , metallurgy
In the presence of a relatively small amount of bromate, maleic acid in aqueous sulfuric acid isomerizes catalytically to fumaric acid in the dark at room temperature. The concomitant presence of a suitable amount of bromine in CCI, phase raises the rate and yield significantly. The yield and rate of isomerization depend on the relative amounts of maleic acid, bromate, bromine, and sulfuric acid. For a favorable condition, nearly 90% yield can be obtained. Raising the temperature accelerates the production of fumaric acid while decreases the final yield. The isomerization reaction competes favorably with the redox reaction at room temperature while the latter dominates at high temperature. For the heterogeneous case, the agitation of the reaction mixture delays the isomerization. The presence of cumene or benzene inhibits the isomerization. Hypobromous acid is proposed to play a major role in catalyzing the isomerization. A mechanism is proposed to rationalize the experimental results.