Diethyl maleate

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 name of diethyl (Z)-but-2-enedioate.[1]

Diethyl maleate
Names
IUPAC name
diethyl (Z)-but-2-enedioate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.957
EC Number
  • 205-451-9
UNII
Properties
C8H12O4
Molar mass 172.180 g·mol−1
Hazards
GHS pictograms
GHS Signal word Warning
H317, H319, H412
P261, P264, P272, P273, P280, P302+352, P305+351+338, P321, P333+313, P337+313, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

The material is synthesized by the esterification of maleic acid or maleic anhydride and ethanol.[2][3][4]

Uses

One of the key uses for the compound is in production of the pesticide Malathion. It has also been used medically as a chemical depletory of glutathione.[5] It has been studied extensively with regard to renal function.[6] Other medical uses include treatment of breast cancer and its monitoring with Positron Emission Tomography.[7] It is also used as a food additive[8] 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 reaction.[9][10] These products are then used in coatings, adhesives, sealants and elastomers.[11]

See also

References
  1. PubChem. "Diethyl maleate". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-05-13.
  2. , "Diethyl maleate preparation method", issued 2014-09-16
  3. Sirsam and Usmami. "Kinetic Study for the Synthesis of Diethyl Maleate over Cation Exchange Resin Indion 730" (PDF).
  4. US Patent US7977324
  5. Uthus, Eric O. (1994-12-01). "Diethyl maleate, an in vivo chemical depletor of glutathione, affects the response of male and female rats to arsenic deprivation". Biological Trace Element Research. 46 (3): 247–259. doi:10.1007/BF02789300. ISSN 1559-0720. PMID 7702979.
  6. Davis, Mary E.; Berndt, William O.; Mehendale, Harihara M. (1986-05-01). "Effects of cysteine and diethylmaleate pretreatments on renal function and response to a nephrotoxicant". Archives of Toxicology. 59 (1): 7–11. doi:10.1007/BF00263949. ISSN 1432-0738. PMID 3741149.
  7. Čolović, Milena; Yang, Hua; Merkens, Helen; Colpo, Nadine; Bénard, François; Schaffer, Paul (2019-12-01). "Non-invasive Use of Positron Emission Tomography to Monitor Diethyl maleate and Radiation-Induced Changes in System xC− Activity in Breast Cancer". Molecular Imaging and Biology. 21 (6): 1107–1116. doi:10.1007/s11307-019-01331-8. ISSN 1860-2002. PMID 30838549.
  8. "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information". www.thegoodscentscompany.com. Retrieved 2020-05-14.
  9. US Patent 5,243,012
  10. European Patent EP-A-0,403,921
  11. Howarth, G. A (2003). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 1110–1118. doi:10.1007/BF02699621.


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