Diethyl maleate is an organic compound with the CAS Registry number 141-05-9. It is chemically a maleate ester with the formula C₈H₁₂O₄. It is a colorless liquid at room temperature. It has the

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

name of diethyl (''Z'')-but-2-enedioate.

Synthesis

The material is synthesized by the esterification of

maleic acid Maleic acid or ''cis''-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the ''cis'' Cis–trans isomerism, isomer of butenedioic acid, ...

maleic anhydride Maleic anhydride is an organic compound with the formula . 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. Str ...

and

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

Uses

One of the key uses for the compound is in production of the

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

Malathion Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion. The compound's name is presumably ...

. It has also been used medically as a chemical depletory of

glutathione Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources ...

. It has been studied extensively with regard to renal function. Other medical uses include treatment of breast

cancer Cancer is a group of diseases involving Cell growth#Disorders, abnormal cell growth with the potential to Invasion (cancer), invade or Metastasis, spread to other parts of the body. These contrast with benign tumors, which do not spread. Po ...

and its monitoring with

Positron Emission Tomography Positron emission tomography (PET) is a functional imaging technique that uses radioactive substances known as radiotracers to visualize and measure changes in metabolic processes, and in other physiological activities including blood flow, r ...

. It is also used as a food additive and has Food and Drug Administration clearance for indirect food contact. In synthetic organic chemistry it is a dienophile and used in the Diels-Alder reaction. With the invention of polyaspartic technology the material also found another use. With this technology an amine is reacted with a dialkyl maleate - usually diethyl maleate - utilizing the

Michael addition In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a c ...

reaction. These products are then used in

coatings A coating is a covering that is applied to the surface of an object, or substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. powder coatings. Paints and ...

adhesives Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

sealants Sealant is a substance used to block the passage of fluids through openings in materials, a type of mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulk'' (especially if acrylic latex or polyurethane based ...

and

elastomers An elastomer is a polymer with viscoelasticity (i.e. both viscosity and Elasticity (physics), elasticity) and with weak intermolecular forces, generally low Young's modulus (E) and high failure strain compared with other materials. The term, a ...

References

{{Reflist

External links

Safety Data Sheet Neuchem
Ethyl esters Maleate esters

Synthesis

Uses

See also

References

External links