Diethyl maleate
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IUPAC name
diethyl (Z)-but-2-enedioate
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3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.004.957 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C8H12O4 | |
Molar mass | 172.180 g·mol−1 |
Hazards | |
GHS labelling: | |
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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).
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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][2]
Synthesis
The material is synthesized by the esterification of maleic acid or maleic anhydride and ethanol.[3][4][5]
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.[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
- ^ PubChem. "Diethyl maleate". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-05-13.
- ^ "Maleic Acid Diethyl Ester - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2020-05-14.
- ^ [1], "Diethyl maleate preparation method", issued 2014-09-16
- ^ Sirsam and Usmami. "Kinetic Study for the Synthesis of Diethyl Maleate over Cation Exchange Resin Indion 730" (PDF).
{{cite web}}
: CS1 maint: url-status (link) - ^ US Patent US7977324
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information". www.thegoodscentscompany.com. Retrieved 2020-05-14.
- ^ US Patent 5,243,012
- ^ European Patent EP-A-0,403,921
- ^ 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.