Bis(2-ethylhexyl) maleate is the chemical compound with the structural formula (H3C(−CH2)3−CH(−CH2−CH3)−CH2−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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| Preferred IUPAC name
Bis(2-ethylhexyl) (2Z)-but-2-enedioate | |
| Other names
Bis(2-ethylhexyl) maleate; Di-2-ethylhexyl maleate; Diethylhexyl maleate; DOM
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| 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 labelling: | |
  
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| Warning | |
| H315, H319, H373, H410 | |
| P260, P264, P273, P280, P302+P352, P305+P351+P338, P314, P321, P332+P313, P337+P313, 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).
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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]
See also
editReferences
edit- ^ a b c d e f 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. ISBN 9783527306732.
- ^ "Dioctyl Sulfosuccinate - DOSS Surfactants - Emulsion Polymerization". JLK Industries. Retrieved 2019-07-18.
- ^ "DOM product data" (PDF). esim-chemicals.com.
External links
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