Diethyl maleate

Short description: Chemical compound

Diethyl maleate

Names
Preferred IUPAC name

Diethyl (2Z)-but-2-enedioate

Identifiers

CAS Number

* 141-05-9

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:68508

ChemSpider |

* 4436353

EC Number |

* 205-451-9

PubChem CID

* 5271566

UNII |

* G81WQB56OL

InChI

* 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

SMILES

* CCOC(=O)/C=C\C(=O)OCC

Properties

Chemical formula

| C8H12O4
Molar mass | 172.180 g·mol−1
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H317, H319, H412

GHS precautionary statements

| P261, P264, P272, P273, P280, P302+352, P305+351+338, P321, P333+313, P337+313, 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]

## Contents

* 1 Synthesis
* 2 Uses
* 3 See also
* 4 References
* 5 External links

## 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

## References

1. ↑ PubChem. "Diethyl maleate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/5271566.
2. ↑ Xu, Songhao, "Diethyl maleate preparation method", CN patent 105399623, published 2016-03-16
3. ↑ Sirsam and Usmami. "Kinetic Study for the Synthesis of Diethyl Maleate over Cation Exchange Resin Indion 730". http://www.ijcea.org/papers/298-C03.pdf.
4. ↑ Gutman, Daniella & Wael Baidussi, "Process for preparing malathion for pharmaceutical use", US patent 7977324, published 2011-07-12
5. ↑ PubChem. "Diethyl maleate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/5271566.
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" (in en). 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" (in en). 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" (in en). 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" (in en-US). http://www.thegoodscentscompany.com/data/rw1018941.html.
10. ↑ Wicks, Douglas A. & Philip E. Yeske, "Polyurea coating compositions having improved pot lives", US patent 5243012, published 1993-09-07
11. ↑ Zwiener, Christian; Josef Pedain & Lothar Kahl et al., "Process for the preparation of coatings", EP patent 403921, published 1990-12-27
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.

## External links

* Safety Data Sheet Neuchem

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Diethyl_maleate&oldid=284895"
*[CID]: Compound ID
*[H317]: May cause an allergic skin reaction
*[H319]: Causes serious eye irritation
*[H412]: Harmful to aquatic life with long lasting effects
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P321]: Specific treatment (see … on this label)
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P363]: Wash contaminated clothing before reuse
*[P501]: Dispose of contents/container to …