Diethyl maleate
{{short description|Chemical compound}}
{{Chembox
| ImageFile = Diethyl maleate.svg
| PIN = Diethyl (2Z)-but-2-enedioate
|Section1={{Chembox Identifiers
| CASNo = 141-05-9
| PubChem = 5271566
| EC_number = 205-451-9
| UNII = G81WQB56OL
| ChEBI = 68508
| ChemSpiderID = 4436353
| StdInChI = 1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
| StdInChIKey = IEPRKVQEAMIZSS-WAYWQWQTSA-N
| SMILES = CCOC(=O)/C=C\C(=O)OCC
}}
|Section2={{Chembox Properties
| C=8 | H=12 | O=4
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|317|319|412}}
| PPhrases = {{P-phrases|261|264|272|273|280|302+352|305+351+338|321|333+313|337+313|363|501}}
}}
|Section8={{Chembox Related
}}
}}
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.{{Cite web|title=Diethyl maleate|url=https://pubchem.ncbi.nlm.nih.gov/compound/5271566|last=PubChem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2020-05-13|archive-date=2020-10-15|archive-url=https://web.archive.org/web/20201015105202/https://pubchem.ncbi.nlm.nih.gov/compound/5271566|url-status=live}}
Synthesis
The material is synthesized by the esterification of maleic acid or maleic anhydride and ethanol.{{Cite patent|title=Diethyl maleate preparation method|pubdate=2016-03-16|country=CN|number=105399623|assign=Changzhou Songsheng Perfumery Co. Ltd.|inventor1-last=Xu|inventor1-first=Songhao}}{{Cite web|title=Kinetic Study for the Synthesis of Diethyl Maleate over Cation Exchange Resin Indion 730|url=http://www.ijcea.org/papers/298-C03.pdf|last=Sirsam and Usmami|access-date=2020-05-14|archive-date=2017-08-08|archive-url=https://web.archive.org/web/20170808154125/http://ijcea.org/papers/298-C03.pdf|url-status=live}}{{cite patent|country=US|number=7977324|pubdate=2011-07-12|title=Process for preparing malathion for pharmaceutical use|assign=Taro Pharmaceutical Industries North America Inc.|inventor1-last=Gutman|inventor1-first=Daniella
|inventor2-last=Baidussi|inventor2-first=Wael}}
Uses
One of the key uses for the compound is in production of the pesticide Malathion.{{Cite web|last=PubChem|title=Diethyl maleate|url=https://pubchem.ncbi.nlm.nih.gov/compound/5271566|access-date=2022-02-22|website=pubchem.ncbi.nlm.nih.gov|language=en|archive-date=2022-01-29|archive-url=https://web.archive.org/web/20220129012101/https://pubchem.ncbi.nlm.nih.gov/compound/5271566|url-status=live}} It has also been used medically as a chemical depletory of glutathione.{{Cite journal|last=Uthus|first=Eric O.|date=1994-12-01|title=Diethyl maleate, an in vivo chemical depletor of glutathione, affects the response of male and female rats to arsenic deprivation|journal=Biological Trace Element Research|language=en|volume=46|issue=3|pages=247–259|doi=10.1007/BF02789300|pmid=7702979|issn=1559-0720}} It has been studied extensively with regard to renal function.{{Cite journal|last=Davis|first=Mary E.|last2=Berndt|first2=William O.|last3=Mehendale|first3=Harihara M.|date=1986-05-01|title=Effects of cysteine and diethylmaleate pretreatments on renal function and response to a nephrotoxicant|journal=Archives of Toxicology|language=en|volume=59|issue=1|pages=7–11|doi=10.1007/BF00263949|pmid=3741149|issn=1432-0738}} Other medical uses include treatment of breast cancer and its monitoring with Positron Emission Tomography.{{Cite journal|last=Čolović|first=Milena|last2=Yang|first2=Hua|last3=Merkens|first3=Helen|last4=Colpo|first4=Nadine|last5=Bénard|first5=François|last6=Schaffer|first6=Paul|date=2019-12-01|title=Non-invasive Use of Positron Emission Tomography to Monitor Diethyl maleate and Radiation-Induced Changes in System xC− Activity in Breast Cancer|journal=Molecular Imaging and Biology|language=en|volume=21|issue=6|pages=1107–1116|doi=10.1007/s11307-019-01331-8|pmid=30838549|issn=1860-2002}} It is also used as a food additive{{Cite web|title=The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information|url=http://www.thegoodscentscompany.com/data/rw1018941.html|website=www.thegoodscentscompany.com|language=en-US|access-date=2020-05-14|archive-date=2020-05-01|archive-url=https://web.archive.org/web/20200501020601/http://www.thegoodscentscompany.com/data/rw1018941.html|url-status=live}} 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.{{cite patent|country=US|number=5243012|pubdate=1993-09-07|title=Polyurea coating compositions having improved pot lives|assign=Miles Inc.|inventor1-last=Wicks|inventor1-first=Douglas A.|inventor2-last=Yeske|inventor2-first=Philip E.}}{{cite patent|country=EP|number=403921|pubdate=1990-12-27|title=Process for the preparation of coatings|assign=Bayer AG|inventor1-last=Zwiener|inventor1-first=Christian|inventor2-last=Pedain|inventor2-first=Josef|inventor3-last=Kahl|inventor3-first=Lothar|inventor4-last=Nachtkamp|inventor4-first=Klaus}} These products are then used in coatings, adhesives, sealants and elastomers.{{Cite journal|last=Howarth|first=G. A|date=2003|title=Polyurethanes, polyurethane dispersions and polyureas: Past, present and future|journal=Surface Coatings International Part B: Coatings Transactions|volume=86|issue=2|pages=1110–1118|doi=10.1007/BF02699621}}
See also
References
{{Reflist}}
External links
- [https://neuchem.com/wp-content/uploads/2013/03/Diethyl-maleate-MSDS.pdf Safety Data Sheet Neuchem ]