Polynt fumaric acid complies with the current edition of us fcc, uspnf and eu. Title cistrans isomerization of maleic acid to fumaric. The encoded protein forms a cytosolic homotetramer and primarily catalyzes the reversible hydrolytic cleavage of argininosuccinate into arginine and fumarate, an essential step in the liver in detoxifying ammonia via the urea cycle. Fumaric acid market size, share global industry analysis. Active research on carbon economy and biorefinery concepts has sped up the biological production of fa. Pdf theoretical study of the isomerization of maleic acid into. The packed bags shall be kept under shade, dry, and protected from rain. Fumaric acid is used in small amounts in the preparation of food, i. Predict the consequences if it is used to purify the crystallized fumaric acid product polar in. Maleic acid is a geometric isomer of fumaric acid, having two carboxyl groups cooh on the same side of an ethylene chain. Us2441238a conversion of maleic acid to fumaric acid.
Maleic acid, also called cisbutenedioic acid ho 2 cchchco 2 h, unsaturated organic dibasic acid, used in making polyesters for fibrereinforced laminated moldings and paint vehicles, and in the manufacture of fumaric acid and many other chemical products. Recent developments in maleic acid synthesis from bio. The method comprises an isomerization reaction process of the maleic anhydride waste water, a centrifugal separation process of fumaric acid head products, a dissolution and decoloration process of the fumaric acid, a filtration process, a crystallization and recrystallization process. Expired lifetime application number us569419a inventor andrew p dunlop. Brittain, in analytical profiles of drug substances and excipients, 2001.
Nowadays, fumaric acid is produced through petrochemical routes via isomerization of maleic acid that, in turn, is obtained by the hydrolysis of. Maleic and fumaric acids are both dicarboxylic acids and have the same molecular weight. Adi not specified established at the 35th jecfa in 1989. Different forms of maleic and fumaric acids cis and trans of 2. Maleic acid or cisbutenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. In this procedure, the mobile phase is filtered and degassed 0. Nervertheless they have different structural formulas. Quantum yeilds for isomerization of fumaric acid were generally higher than those of maleic acid. Maleic acid ma and fumaric acid fa are very important chemical intermediates that find applications in nearly every field of industrial chemistry. Maleic acid 2 115 32 28 fumaric acid 1 115 71 11 fumaric acid 2 115 32 28 results and discussion an example chromatogram of the detection of maleic acid and fumaric acid is shown in figure 1. The invention relates to a method for producing fumaric acid by maleic anhydride waste water.
It has a role as a food acidity regulator and a fundamental metabolite. Difference between maleic acid and fumaric acid compare. The structural formula of malic acid is hoocch2chohcooh, and that of the other one is hoocchchcooh cisisomer of butenedioic acid. Fumaric acid is a butenedioic acid in which the cc double bond has e geometry. Fumaric acid is a chemical compound that occurs in plants like lichen and bolete mushrooms. Both acids are readily esterified by the action of alkyl halides on their silver salts, and the maleic ester is readily transformed into the fumaric ester by warming with iodine, the same result being obtained by esterification of maleic acid in alcoholic solution by means of hydrochloric acid. The fda and european food safety agency have declared that fumaric acid is safe for human consumption. It also forms within human skin when that skin is exposed to sunlight. It was first produced by pelouze in 1834 by heating malic acid.
Development of an amperometric biosensor platform for the combined determination of lmalic, fumaric, and laspartic acid. The key difference between maleic acid and fumaric acid is that maleic acid is the cisisomer of butenedioic acid, whereas fumaric acid is the transisomer. It is an intermediate metabolite in the citric acid cycle. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. Therecognitionof fu maric and maleic acids as geometrical isomers, as proposed by vant hoff, was due chiefly to the work. Fumaric acid is a chemical thats naturally produced when human skin is exposed to sunlight. Various tests conducted by different health bodies have cleared fumaric acid as being safe for human beings. Maleic acid material safety data sheet cas no 11016. Cistrans isomerization of maleic acid to fumaric acid under pressure.
First, the limit of quantitation loq, linearity, and repeatability were evaluated using injections of maleic and fumaric acid. Pdf the isomerization reaction of 2butenedioic acid in gas phase has been studied. The global fumaric acid market size demand was 245. Any fumaric or maleic acid impurities in a sample of malic acid are determined using high pressure liquid chromatography. Fumaric acid or e2butanodioic acid is a transc4 dicarboxilic acid, while maleic acid is its ciscounterpart. Physical and chemical properties for these three chemicals are updated with literature citations when available. The photochemical isomerization of maleic to fumaric acid. In the treatment of psoriasis, doses of several hundred mg are common.
Cn103204772a method for producing fumaric acid by maleic. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Maleic acid was available commercially in 1928 and fumaric acid production began in 1932 by acidcatalyzed isomerization of maleic acid. We have been investigating the structures of hydrogen bonded adducts obtained by the cocrystallization of aliphatic dicarboxylic acids with molecules. Fumaric acid chemical economics handbook ceh ihs markit. Maleic acid cas no 110167 material safety data sheet sdsmsds. Fumaric and maleic acids, two isomeric unsaturated acids of composition c 4 h 4 o 4. Its used in a number of foods as a flavoring agent. It is generated by oxidation of adenylsuccinate by the enzyme succinate dehydrogenase and is then converted to maleate by the enzyme fumarase. Maleic acid is the cisisomer of butenedioic acid, whereas fumaric acid is the transisomer. Decolorizing carbon, a solid which was used in the recrystallization experiment, works by bonding with polar compounds. For instance maleic acid transforms into fumaric acid at high temperatures melting point.
Maleic acid is a butenedioic acid in which the double bond has cis zconfiguration. Maleic acid is an organic salt or ester of maleic acid that could be conjugated to free base compoundsdrugs to improve the physiochemical properties including stability, solubility and dissolution rate. Fumaric acid, organic compound related to maleic acid. Maleic acid and its anhydride are prepared industrially by the catalytic oxidation of benzene. Maleic acid ma is a dicarboxylic acid that undergoes esterification with ethanol in the presence of cationexchange resin catalysts to form diethyl maleate. This weak acid forms a diester, it undergoes additions across the double bond, and it is an excellent dienophile. Explain why maleic acid is weighed after grinding, rather than before. Stabilization of maleic acid by a strong hydrogen bond is. Does fumaric acid form maleic anhydride upon heating. This acid presents a high boiling point due to its being a transacid, an aspect that permits a close intermolecular interaction. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Maleic anhydride 108316 1, maleic acid 110167 2, and fumaric acid 110178 3 are. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few.
Fumaric acid or e2butanodioic acid is a transc4 dicarboxilic acid, while maleic acid is its cis counterpart. Both these compounds have two carboxylic acid groups per molecule. Castro and others published the photochemical isomerization of maleic to fumaric acid. It can be seen that malic acid is a saturated dicarboxylic acid whereas malei. Fumaric acid prepared at the 53rd jecfa 1999 and published in fnp 52 add 7 1999, superseding specifications prepared at the 35th jecfa 1989 and published in fnp 49 1990. Fumaric acid is an intermediate product of the citric acid cycle that is a source of intracellular energy in the form of adenosine triphosphate atp. In addition, the competitive conversion of maleic acid, fumaric acid, and.
Maleic acid 110167, c4h4o 4, cisbutene dioic acid, mr 116. This acid presents a high boiling point due to its being a transacid, an aspect. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid 1 degree centigrade is also much lower than that of fumaric acid 287 degree centigrade. The progress made in the applied field has helped in reevaluating fumaric acid fa beyond the scope of a platform chemical. Maleic and fumaric acids have physical properties that differ owing to the cis and trans configurations about the double bond. Tolerance for the fetus has not been systematically studied, but the current unpublished experience of the authors on psoriasis treatment with fumaric acid. Theoretical study of the isomerization of maleic acid into fumaric acid. Rising popularity of processed food and demand for readytodrink beverages is expected to remain a key factor driving the growth. Fumaric acid is a key intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals. As is well known, substituted ethylenes exhibit cistrans isomerism. Claydens organic chemistry textbook mentions this as a point of distinction between it and fumaric acid the trans isomer, which fails to dehydrate to its anhydride upon heating. Experimental thermodynamic functions concerning isomerization of maleic acid to fumaric acid are well reproduced by theoretical calculation using a userdefined model at a blyp sto6g level of theory. Kinetic study on the preparation of fumaric acid from. A highly selective conversion of fumaric acid was achieved without a catalyst by a simple onestep hydrothermal reaction.
Immobilization techniques and genetic and metabolic engineering. Title cistrans isomerization of maleic acid to fumaric acid under. The encoded protein forms a cytosolic homotetramer and primarily. What is the difference between malic acid and maleic acid. Each molecule contains two acid carbonyl groups and a double bond in the.
In addition, scientists have created a synthetic version that is often used as an additive in several foods to enhance a. Fumaric acid trans2butenedioic acid is a multifunctional chemical with a diverse set of end uses, including unsaturated polyester resins, food and beverages, laspartic acid, rosin paper sizes, alkyd resins, and animal feed. Key derivatives are summarized, including acid chlorides. Maleic acid is an important raw material used in the manufacture of lubricant additives, unsaturated polyester resins, surface coatings, plasticizers, copolymers and agricultural chemicals 15. Reaction kinetics and mechanism of the isomerization of maleic acid to fumaric acid in the presence of ceric and bromide ions has been. The chemical properties of fumaric acid can be anticipated from its component functional groups. Pdf the photochemical isomerization of maleic to fumaric acid. The physical properties of maleic acid are very different from that of fumaric acid. It is a colorless crystalline acid used in textile processing and as an oil and fat preservative. Kinetic study on the preparation of fumaric acid from maleic acid by. Fumaric acid does not combust in a bomb calorimeter under conditions where maleic acid deflagrates smoothly.
Due to its reactivity fa is a useful material for a variety of industrial applications such as paper sizing, unsaturated polyester resins u. Unsaturated polyester resin upr is the largest end use for fumaric acid in 2019. It is the cisisomer of butenedioic acid, whereas fumaric. Also, describe the grinding procedure and location. Chromatograph the resolution solution, and record the peak responses. In recent years, the increase in demand for fumaric acid from industry has resulted in an increased need for a highselectivity process for the conversion of maleic acid to fumaric acid. Fumaric acid or transbutenedioic acid, is a white crystalline chemical compound widely found in nature. The key difference between maleic acid and fumaric acid is that maleic acid is the cisisomer of butenedioic acid, whereas fumaric acid is the transisomer maleic acid and fumaric acid are carboxylic acids.
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