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
Preferred IUPAC name
Diethyl (2Z)-but-2-enedioate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.957
EC Number
  • 205-451-9
UNII
  • InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
    Key: IEPRKVQEAMIZSS-WAYWQWQTSA-N
  • CCOC(=O)/C=C\C(=O)OCC
Properties
C8H12O4
Molar mass 172.180 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H317, H319, H412
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, 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.[5] It has also been used medically as a chemical depletory of glutathione.[6] It has been studied extensively with regard to renal function.[7] Other medical uses include treatment of breast cancer and its monitoring with Positron Emission Tomography.[8] It is also used as a food additive[9] 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.[10][11] These products are then used in coatings, adhesives, sealants and elastomers.[12]

See also

References
  1. PubChem. "Diethyl maleate". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2020-10-15. Retrieved 2020-05-13.
  2. CN 105399623, Xu, Songhao, "Diethyl maleate preparation method", published 2016-03-16, assigned to Changzhou Songsheng Perfumery Co. Ltd.
  3. Sirsam and Usmami. "Kinetic Study for the Synthesis of Diethyl Maleate over Cation Exchange Resin Indion 730" (PDF). Archived (PDF) from the original on 2017-08-08. Retrieved 2020-05-14.
  4. US 7977324, Gutman, Daniella & Baidussi, Wael, "Process for preparing malathion for pharmaceutical use", published 2011-07-12, assigned to Taro Pharmaceutical Industries North America Inc.
  5. PubChem. "Diethyl maleate". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2022-01-29. Retrieved 2022-02-22.
  6. 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.
  7. 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.
  8. 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.
  9. "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information". www.thegoodscentscompany.com. Archived from the original on 2020-05-01. Retrieved 2020-05-14.
  10. US 5243012, Wicks, Douglas A. & Yeske, Philip E., "Polyurea coating compositions having improved pot lives", published 1993-09-07, assigned to Miles Inc.
  11. EP 403921, Zwiener, Christian; Pedain, Josef & Kahl, Lothar et al., "Process for the preparation of coatings", published 1990-12-27, assigned to Bayer AG
  12. 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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