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Bis(2-ethylhexyl) maleate

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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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.022 Edit this at Wikidata
EC Number
  • 205-524-5
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Appearance Colorless liquid
Density 0.94 g/cm
Melting point −60 °C (−76 °F; 213 K)
Boiling point 156 °C (313 °F; 429 K)
Solubility in water 0.036 mg/L (20 °C)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Warning
Hazard statements H315, H319, H373, H410
Precautionary statements 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

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.

See also

References

  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. ISBN 9783527306732.
  3. "Dioctyl Sulfosuccinate - DOSS Surfactants - Emulsion Polymerization". JLK Industries. Retrieved 2019-07-18.
  4. "DOM product data" (PDF). esim-chemicals.com.

External links

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