Fumaric acid, production and applications

FUMARIC ACID PRODUCTION AND APPLICATION ASPECTS TABLE 8.6 Different Immobilization-Based Studies for Fumaric Acid Production ... 

After the primary recovery of MA during production, the remaining MA is recovered as maleic acid by scrubbing with water. Some of this can be and often is converted to fumaric acid. High-purity fumaric acid for food applications is made from refined MA. The isomerization may be brought about in a number of ways, e.g., thermal, yy (7i,83) catalytic. Aqueous solutions containing 40% maleic acid when heated to form fumaric... 

FUMARIC ACID PRODUCTION AN D APPLICATION ASPECTS TABLE 8.7 Important Molecular Mechanisms/Factors Involved in the Morphogenesis of Some Model Filamentous Fungi and Their Predicted Relevancy for the Fumaric Acid-Producing Fungal Strains ... 

Producers of acidulants came to food applications through chemistry or biochemistry. Malic acid is produced by Denka, now owned by Mobay, in the United States and by Croda in England. Like fumaric acid, it is a derivative of maleic anhydride production. The... 

The oxidation of 1,4-dicarboxylic acids with LTA in benzene results in double decarboxylation with the formation of a double bond (equation 16). Similarly, the pyrolysis of the di-r-butyl peroxy esters of 1,4-dicarboxylic acids in high boiling solvents leads to the formation of double bonds (equation 17). The method is especially useful in so far as 1,4-diacids are readily available from Diels-Alder reactions using derivatives of mtdeic and fumaric acid as the dienophile. Apparently, application of the 0-acyl thiohydroxamate method to 1,4-diacids does not result in the formation of double bonds but rather in the product of double decarboxylative rearrangement (Section S.4.6.1). ... 

Similar to fumaric acid, L-malic acid is also a naturally occurring four-carbon dicarboxyhc acid and an intermediate in the TCA cycle. It has been used in many food products, primarily as an acidulant. L-Malic acid is compatible with all sugars with low hygroscopicity and good solubihty. In addition, it has therapeutic value for the treatment of hyperammoemia and liver dysfunction and as a component for amino acid infusion. L-Malic acid has been the subject of interest because of its increased application in the food industry as a citric acid replacement and its potential use as a raw material for the manufacture of biodegradable polymers. 

Ammonia lyases in their natural role are involved in the metabolism of amino acids and also play a role in, for instance, the degradation of amino sugars, but only a limited amount of these enzymes have been characterized biochemically. Application of a broad range of different ammonia and lyases in organic chemical synthesis on an industrial scale has thus far not occurred, which is due to both their limited commercial availability and their lack of stability under process conditions. Exceptions are the commercially applied aspartase, which is an ammonia lyase that is utilized for the synthesis of L-aspartic acid from fumaric acid, and phenylalanine lyase. The latter is an example of a commercial application of an ammonia lyase in a process for the production of L-phenylalanine and more importantly L-phenylalanine derivatives. 

UP resins are soluble linear polycondensation products made from polyvalent -usually unsaturated - acids (e.g. maleic or fumaric acids) and bivalent alcohols (e.g. ethylene glycol and/or 1,2-propylene glycol). For special applications, it is common to substitute some of the a, -unsaturated dicarboxylic acids with phthalic acid and/or adipic acid. Seminal work on unsaturated polycondensation products made from maleic acid, maleic acid anhydride and glycols and on their copolymerisation with styrene is listed in [2.100],... 

PPF is an unsaturated hnear polyester (Eig re 1) that degrades into fumaric acid and propylene glycol, both biocompatible degradation products. Many formulation methods have been proposed for orthopaedic applications. Once PPF is produced, it can be crosslinked through the fumarate double bond widi a vinyl monomer. Various filler particles can be incorporated to create porosity, increase mechanical properties, and enhance osteoconductivity. This mixture creates a moldable paste suitable for filling irregularly shaped bone defects that hardens in a short period of time. This review describes the many metliods used to synthesize and characterize PPF, and explores possible applications. 

Maleic anhydride can function both as a dibasic acid in the polyesterification reaction and a dienophile for Diels-Alder reaction with the fatty acid. The total functionality of the alkyd resin is significantly enhanced by MA. Thus, the replacement of phthalic anhydride by MA produces a more complex molecular structure with high viscosity and possible gelation. In normal alkyd production, MA or fumaric acid is usually restricted to about 1-10% of the phthalic anhydride content. Maleic anhydride incorporation improves color, processing time, and water resistance of the alkyd coating. Alkyd molding compositions are also being used to some extent in automotive and electrical applications. 

TABLE 8.4 Different Neutralizing Agents Used in the Fermentative Production of Fumaric Acid and Their Advantages/Disadvantages of Applications ... 

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