Diethyl maleate

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Diethyl maleate
Diethyl maleate.svg
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
Signal word
 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

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. 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. ^ [1], "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.

External links[]

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