Bis(2-ethylhexyl) maleate
Bis(2-ethylhexyl) maleate is the chemical compound with the structural formula (H
3C(−CH
2)
3−CH(−CH
2−CH
3)−CH
2−O−C(=O)−CH=)
2, where the two carboxylate groups are mutually cis. It can be described as the double ester of maleic acid with the alcohol 2-ethylhexanol. It is commonly called dioctyl maleate (DOM), reflecting the older usage of "octane" to refer to any 8-carbon alkane, straight-chained or branched.
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Names | |
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IUPAC name
Bis(2-ethylhexyl) (Z)-but-2-enedioate | |
Other names
Bis(2-ethylhexyl) maleate; Di-2-ethylhexyl maleate; Diethylhexyl maleate; DOM | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.005.022 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C20H36O4 | |
Molar mass | 340.504 g·mol−1 |
Appearance | Colorless liquid[1] |
Density | 0.94 g/cm3[1] |
Melting point | −60 °C (−76 °F; 213 K)[1] |
Boiling point | 156 °C (313 °F; 429 K)[1] |
0.036 mg/L (20 °C)[1] | |
Hazards | |
GHS pictograms | ![]() ![]() ![]() |
GHS Signal word | Warning |
GHS hazard statements |
H315, H319, H373, H410 |
P260, P264, P273, P280, P302+352, P305+351+338, P314, P321, P332+313, P337+313, P362, P391, P501 | |
Flash point | 185 °C (365 °F; 458 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
The compound is manufactured by treating 2-ethylhexanol with maleic anhydride and an esterification catalyst. It is a key intermediate raw material in the production of dioctyl sulfosuccinate (DOSS, docusate) salts, used medically as laxatives and stool softeners, and in many other applications as versatile surfactants.[2][3][4].
References
- Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- Engelhorn, Robert; Seeger, Ernst; Zwaving, Jan H.; Eberlin, Marion (2014). "Laxatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–10. doi:10.1002/14356007.a15_183.pub2.
- "Dioctyl Sulfosuccinate - DOSS Surfactants - Emulsion Polymerization". JLK Industries. Retrieved 2019-07-18.
- "DOM product data" (PDF). esim-chemicals.com.
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