Diethyl maleate explained

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

• Dimethyl maleate
• Dibutyl maleate

External links

• Safety Data Sheet Neuchem

Notes and References

1. Web site: Diethyl maleate. PubChem. pubchem.ncbi.nlm.nih.gov. en. 2020-05-13. 2020-10-15. https://web.archive.org/web/20201015105202/https://pubchem.ncbi.nlm.nih.gov/compound/5271566. live.
2. Diethyl maleate preparation method. 2016-03-16. CN. 105399623. Changzhou Songsheng Perfumery Co. Ltd.. Xu. Songhao.
3. Web site: Kinetic Study for the Synthesis of Diethyl Maleate over Cation Exchange Resin Indion 730. Sirsam and Usmami. 2020-05-14. 2017-08-08. https://web.archive.org/web/20170808154125/http://ijcea.org/papers/298-C03.pdf. live.
4. US. 7977324. 2011-07-12. Process for preparing malathion for pharmaceutical use. Taro Pharmaceutical Industries North America Inc.. Gutman. Daniella . Baidussi. Wael.
5. Web site: PubChem. Diethyl maleate. 2022-02-22. pubchem.ncbi.nlm.nih.gov. en. 2022-01-29. https://web.archive.org/web/20220129012101/https://pubchem.ncbi.nlm.nih.gov/compound/5271566. live.
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. en. 46. 3. 247–259. 10.1007/BF02789300. 7702979. 1559-0720.
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. en. 59. 1. 7–11. 10.1007/BF00263949. 3741149. 1432-0738.
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. en. 21. 6. 1107–1116. 10.1007/s11307-019-01331-8. 30838549. 1860-2002.
9. Web site: The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information. www.thegoodscentscompany.com. en-US. 2020-05-14. 2020-05-01. https://web.archive.org/web/20200501020601/http://www.thegoodscentscompany.com/data/rw1018941.html. live.
10. US. 5243012. 1993-09-07. Polyurea coating compositions having improved pot lives. Miles Inc.. Wicks. Douglas A.. Yeske. Philip E..
11. EP. 403921. 1990-12-27. Process for the preparation of coatings. Bayer AG. Zwiener. Christian. Pedain. Josef. Kahl. Lothar. Nachtkamp. Klaus.
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. 10.1007/BF02699621.