Dioctyl 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

EC Number |

* 205-524-5

PubChem CID

* 5365125

UNII |

* C2F7JHI12L

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

Tracking categories (test):

* SizeSet

Dioctyl maleate is a chemical compound with the molecular formula C20H36O4. It is often called DOM in the chemical industry even though the octyl is not straight chained but branched. It is manufactured by reacting 2-ethylhexanol with maleic anhydride and an esterification catalyst. This is a key intermediate raw material in the production of DOSS surfactants[2], including the pharmaceutical drug docusate (dioctyl sodium sulfosuccinate).[3]. The DOSS molecule is formed by reacting a metal (usually sodium) bisulfite across the vinylic double bond of the dioctyl maleate thus forming an ionic species.

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Record  in the GESTIS Substance Database of the Institute for Occupational Safety and Health
2. ↑ "Dioctyl Sulfosuccinate - DOSS Surfactants - Emulsion Polymerization" (in en-US). https://www.jlkindustries.com/dioctyl-sulfosuccinates.
3. ↑ "DOM product data". http://www.esim-chemicals.com/binaries/content/assets/products/dfc000037r1-dom-product-data-sheet-esim.pdf.

## External links

* Aerosol Surfactants
* MSDS
* General data and uses
* product data

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Dioctyl_maleate&oldid=494193"
*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H373]: May cause damage to organs through prolonged or repeated exposure
*[H410]: Very toxic to aquatic life with long lasting effects
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P314]: Get Medical advice/attention if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P391]: Collect spillage
*[P501]: Dispose of contents/container to …