Bis(2-ethylhexyl) maleate

Bis(2-ethylhexyl) maleate
Names
	IUPAC name Bis(2-ethylhexyl) (Z)-but-2-enedioate
	Other names Bis(2-ethylhexyl) maleate; Di-2-ethylhexyl maleate; Diethylhexyl maleate; DOM
Identifiers
CAS Number	142-16-5;
3D model (JSmol)	Interactive image;
ChemSpider	4517207;
ECHA InfoCard	100.005.022
EC Number	205-524-5;
PubChem CID	5365125;
UNII	C2F7JHI12L;
CompTox Dashboard (EPA)	DTXSID2027094 ;
	InChI 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;
	SMILES CCCCC(CC)COC(=O)/C=C\C(=O)OCC(CC)CCCC;
Properties
Chemical formula	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]
Solubility in water	0.036 mg/L (20 °C)[1]
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H373, H410
GHS precautionary statements	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

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.

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.

External links

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[GESTIS-1] 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.

[3] "Dioctyl Sulfosuccinate - DOSS Surfactants - Emulsion Polymerization". JLK Industries. Retrieved 2019-07-18.

[4] "DOM product data" (PDF). esim-chemicals.com.