Plastic Auxiliary Agents & Other Organic Chemicals Used Maleic Anhydride

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Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor.It is produced industrially on a large scale for applications in coatings and polymers.

Maleic anhydride is produced by vapor-phase oxidation of n-butane. The overall process converts the methyl groups to carboxylate and dehydrogenates the backbone.The selectivity of the process reflects the robustness of maleic anhydride, with its conjugated double-bond system. Traditionally maleic anhydride was produced by the oxidation of benzene or other aromatic compounds. As of 2006, only a few smaller plants continue to use benzene. In both cases, benzene and butane are fed into a stream of hot air, and the mixture is passed through a catalyst bed at high temperature.

The ratio of air to hydrocarbon is controlled to prevent the mixture from igniting. The main competing process entails full combustion of the butane, a conversion that is twice as exothermic as the partial oxidation.

The traditional method using benzene became uneconomical due to the high and still rising benzene prices and by complying the regulations of benzene emissions. In addition, in the production of maleic anhydride a third of the original carbon atoms is lost as carbon dioxide when using benzene (6 carbon atoms). The modern catalytic processes start from a 4-carbon molecule and only attaches oxygen and removes water; the 4-C-base body of the molecule remains intact. Overall, the newer method is therefore more material efficient.

Parallels exist with the production of phthalic anhydride: While older methods use naphthalene, modern methods use o-xylene as feedstock.

The chemistry of maleic anhydride is very rich, reflecting its ready availability and bi-functional reactivity. It hydrolyzes, producing maleic acid, cis-HOOC-CH=CH-COOH. With alcohols, the half-ester is generated, e.g. cis-HOOC-CH=CH-COOCH₃.

Maleic anhydride is a classic substrate for Diels-Alder reactions. It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride converted to many pesticides and pharmaceuticals.

Michael reaction of maleic anhydride with active methylene or methine compounds such as malonate or acetoacetate esters in the presence of sodium acetate catalyst. These intermediates were subseqeuently used for the generation of the Krebs cycle intermediates aconitic and isocitric acids.

Maleic anhydride dimerizes in a photochemical reaction to form cyclobutane tetracarboxylic dianhydride. This compound is used in the production of polyimides and as an alignment film for liquid crystal displays.

It is also a ligand for low-valent metal complexes, examples being Pt(PPh₃)₂(MA) and Fe(CO)₄(MA). Liquid maleic anhydride is available in road tankers and/or tank-containers which are made of stainless steel, which are insulated and provided with heating systems to maintain the temperature of 65-75℃. Tank cars must be approved for the transport of molten maleic anhydride.

Liquid/ molten maleic anhydride is a dangerous material in accordance with RID/ADR.

Solid maleic anhydride pastilles are transported by transport trucks. Packaging is generally in 25kg polyethylene bags.

Effects on human health and the environment

This compound poses relatively low-risk environmental hazards, an important feature for some applications. In humans, exposure to maleic anhydride may cause irritation to the respiratory tract, eyes,exposed mucosa, and skin. Maleic anhydride is a low hazard profile chemical. Maleic anhydride is also a skin and respiratory sensitizer.

Applications

Maleic anhydride is used in many applications. Around 50% of world maleic anhydride output is used in the manufacture of unsaturated polyster resins (UPR). Chopped glass fibers are added to UPR to produce fiberglass reinforced plastics that are used in a wide range of applications such as pleasure boats, bathroom fixtures, automobiles, tanks and pipes.

A number of smaller applications for maleic anhydride. The food industry uses maleic anhydride in artificial sweeteners and flavor enhancements Personal care products consuming maleic anhydride include hair sprays, adhesives and floor polishes. Maleic anhydride is also a precursor to compounds used for water treatment detergents, insecticides and fungicides,pharmaceuticals and other copolymers.

Storage

Requirements for storage buildings:

Local exhaust systems to take vapors away from the places of emission, and general ventilation in rooms.

Protection against static charges.

Impervious floor which makes it possible to collect the spilled material and which prevents its entry to the sewage systems.

Storage rooms should be cool and dry.

Storage conditions:

Keep ignition sources away- do not smoke.Product dust may form explosive air-dust mixtures.

Keep humidity away from storage rooms.

Keep containers tightly closed. Store them in cool, dry and well ventilated places.

Tanks/containers must be properly marked.

Hand-operated/ portable fire-fighting equipment should be available in storage rooms.

Neutral gas blanketing is required inside storage tanks.

 Attention, please!

Maleic anhydride is a low hazard profile chemical. Maleic anhydride rapidly hydrolyzes to form maleic acid in the presence of water and hence environmental exposures to maleic anhydride itself are unlikely. Maleic acid is biodegradable under aerobic conditions in sewage sludge as well as in soil and water.

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