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Bis(2-ethylhexyl) maleate

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.

Bis(2-ethylhexyl) maleate
Names
Preferred IUPAC name
Bis(2-ethylhexyl) (2Z)-but-2-enedioate
Other names
Bis(2-ethylhexyl) maleate; Di-2-ethylhexyl maleate; Diethylhexyl maleate; DOM
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.022 Edit this at Wikidata
EC Number
  • 205-524-5
UNII
  • InChI=1S/C20H36O4/c1-5-9-11-17(7-3)15-23-19(21)13-14-20(22)24-16-18(8-4)12-10-6-2/h13-14,17-18H,5-12,15-16H2,1-4H3/b14-13-
    Key: ROPXFXOUUANXRR-YPKPFQOOSA-N
  • CCCCC(CC)COC(=O)/C=C\C(=O)OCC(CC)CCCC
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:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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).

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

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References

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  1. ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ 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.
  3. ^ "Dioctyl Sulfosuccinate - DOSS Surfactants - Emulsion Polymerization". JLK Industries. Retrieved 2019-07-18.
  4. ^ "DOM product data" (PDF). esim-chemicals.com.
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