and you may need to create a new Wiley Online Library account. 2 A Novel Voltammetric Method for the Determination of Maleic Acid Using Silver Amalgam Paste Electrode. For teaching experiments designed to measure the difference in energy between the cis- and trans- isomers, a measured quantity of carbon can be ground with the subject compound and the enthalpy of combustion computed by difference. Physical and chemical properties for these three chemicals are updated with literature citations when available. O As well as being a component of some artificial vinegar flavors, such as "Salt and Vinegar" flavored potato chips,[10] it is also used as a coagulant in stove-top pudding mixes. Institute for Occupational Safety and Health, Active Ingredients Used in Cosmetics: Safety Survey, "Current EU approved additives and their E Numbers", "Listing of Food Additives Status Part II", "Standard 1.2.4 - Labelling of ingredients", "The Science Behind Salt and Vinegar Chips", "European Commission Report of the Scientific Committee on Animal Nutrition on the Safety of Fumaric Acid", https://en.wikipedia.org/w/index.php?title=Fumaric_acid&oldid=976832123, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 5 September 2020, at 09:00. p It is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase. If you do not receive an email within 10 minutes, your email address may not be registered, Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers. The European Commission Scientific Committee on Animal Nutrition, part of DG Health, found in 2014 that fumaric acid is "practically non-toxic" but high doses are probably nephrotoxic after long-term use.[11]. Maleic acid, also called cis-butenedioic acid (HO2CCH=CHCO2H), unsaturated organic dibasic acid, used in making polyesters for fibre-reinforced laminated moldings and paint vehicles, and in the manufacture of fumaric acid and many other chemical products. It is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid. EXPOSURE: Workers making maleic acid … Fumaric acid, or trans-butenedioic acid, the geometrical isomer of maleic acid, occurs in fumitory (Fumaria officinalis), in various fungi, and in Iceland moss. Maleic acid and fumaric acid are carboxylic acids. [§ 1]. Our editors will review what you’ve submitted and determine whether to revise the article. A survey is given of catalyst developments through the end of 2000. Maleic anhydride is interchangeable with the acid in most applications. Click on genes, proteins and metabolites below to link to respective articles. The interactive pathway map can be edited at WikiPathways: Australia New Zealand Food Standards Code. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Maleic acid melts at 139–140° C (282–284° F); at higher temperatures it forms the anhydride, which, like the acid, is irritating to the skin and toxic. Effect of Addition Mode of Re in Bimetallic Pd–Re/TiO2 Catalysts Upon the Selective Aqueous-Phase Hydrogenation of Succinic Acid to 1,4-Butanediol. Volhard, J. https://www.britannica.com/science/maleic-acid. Learn about our remote access options, Huntsman Petrochemical Corporation Austin Laboratories. Maleic acid and its anhydride are prepared industrially by the catalytic oxidation of benzene. It is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase. It is approved for use as a food additive in the EU,[6] USA[7] and Australia and New Zealand. Let us know if you have suggestions to improve this article (requires login). Fumarate is then converted by the enzyme fumarase to malate. . Clean Technologies and Environmental Policy. Polymers derived from hemicellulosic parts of lignocellulosic biomass. It has a fruit-like taste and has been used as a food additive. "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. Each molecule contains two acid carbonyl groups and a double bond in the α, β position. Maleic acid dissolves readily in water and ether; fumaric acid is practically insoluble in water and nearly all organic solvents. Fumaric acid does not combust in a bomb calorimeter under conditions where maleic acid deflagrates smoothly. Ullmann's Encyclopedia of Industrial Chemistry,  10.1002/0471238961.1301120506051220.a01.pub2,  10.1002/0471238961.1301120506051220.a01, https://doi.org/10.1002/0471238961.1301120506051220.a01.pub2. Kirk‐Othmer Encyclopedia of Chemical Technology. Fumarate can also refer to the C4H2O2−4 ion (in solution). Oxide Nanocatalyst for Aqueous‐Phase Oxidation of Furfural to Renewable Maleic Acid Omissions? Eco-efficiency and techno-economic analysis for maleic anhydride manufacturing processes. Please check your email for instructions on resetting your password. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use.