Diethyl maleate

Diethyl maleate
Names
Preferred IUPAC name
Diethyl (2Z)-but-2-enedioate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.957 Edit this at Wikidata
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).

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]

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.