Bis(2-ethylhexyl) maleate

Last updated
Bis(2-ethylhexyl) maleate
Bis(2-ethylhexyl) maleate.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-524-5
PubChem CID
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
AppearanceColorless 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:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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).

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.

Contents

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

Related Research Articles

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Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. Surfactants may function as emulsifiers, wetting agents, detergents, foaming agents, or dispersants. The word "surfactant" is a blend of surface-active agent, coined c.  1950.

<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

Dom or DOM may refer to:

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, R being an alkyl group or an aryl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

<span class="mw-page-title-main">2-Butoxyethanol</span> Chemical compound

2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH (Bu = CH3CH2CH2CH2). This colorless liquid has a sweet, ether-like odor, as it derives from the family of glycol ethers, and is a butyl ether of ethylene glycol. As a relatively nonvolatile, inexpensive solvent, it is used in many domestic and industrial products because of its properties as a surfactant. It is a known respiratory irritant and can be acutely toxic, but animal studies did not find it to be mutagenic, and no studies suggest it is a human carcinogen. A study of 13 classroom air contaminants conducted in Portugal reported a statistically significant association with increased rates of nasal obstruction and a positive association below the level of statistical significance with a higher risk of obese asthma and increased child BMI.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<span class="mw-page-title-main">Diethanolamine</span> Chemical compound

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

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<span class="mw-page-title-main">Amine oxide</span> Chemical compound containing the functional group R3N→O

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<span class="mw-page-title-main">2-Ethylhexanol</span> Chemical compound

2-Ethylhexanol (abbreviated 2-EH) is an organic compound with formula C8H18O. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

<span class="mw-page-title-main">2-Ethylhexanoic acid</span> Chemical compound

2-Ethylhexanoic acid is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

<span class="mw-page-title-main">Dimethyl maleate</span> Chemical compound

Dimethyl maleate is an organic compound with the formula C6H8O4. It is the dimethyl ester of maleic acid.

<span class="mw-page-title-main">Docusate</span> Laxatives/stool softeners

Docusate is the common chemical and pharmaceutical name of the anion bis(2-ethylhexyl) sulfosuccinate, also commonly called dioctyl sulfosuccinate (DOSS). It is on the World Health Organization's List of Essential Medicines. Salts of this anion, especially docusate sodium, are widely used in medicine as laxatives and as stool softeners, by mouth or rectally. In 2020, it was the 163rd most commonly prescribed medication in the United States, with more than 3 million prescriptions. Some studies claim that docusate is not more effective than a placebo for improving constipation. Other docusate salts with medical use include those of calcium and potassium.

Bis(2-ethylhexyl) adipate or DEHA is an organic compound with the formula (CH2CH2CO2C8H17)2. It is the diester of 2-ethylhexanol and adipic acid. It is a colorless oily liquid.

Dioctyl terephthalate commonly abbreviated DOTP or DEHT, is an organic compound with the formula C6H4(CO2C8H17)2. It is a non-phthalate plasticizer, being the diester of terephthalic acid and the branched-chain 2-ethylhexanol, which is referred to as octyl. This colorless viscous liquid is used for softening PVC plastics and is known for chemical similarity to general purpose phthalates such as DEHP and DINP, but without any negative regulatory pressure. It possesses very good plasticizing properties and may be used as a direct replacement for DEHP and DINP in many applications.

<span class="mw-page-title-main">2-Octanol</span> Chemical compound

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<span class="mw-page-title-main">Sodium sulfosuccinate esters</span>

Sodium sulfosuccinate esters are organic compounds with the formula NaO3SCH(CO2R')CH2CO2R where R and R' can be H or alkyl groups. They comprise a large class of surfactants and emulsifiers used in cosmetics, pharmaceuticals, and cleaning agents. They are colorless salts. These materials can be further classified into monoesters (R' = H, R = alkyl) and diesters (R and R' = alkyl).

Diethyl maleate is an organic compound with the CAS Registry number 141-05-9. It is chemically a maleate ester with the formula C8H12O4. It is a colorless liquid at room temperature. It has the IUPAC name of diethyl (Z)-but-2-enedioate.

α,β-Unsaturated carbonyl compound Functional group of organic compounds

α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ-R. Such compounds include enones and enals. In these compounds the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

References

  1. 1 2 3 4 5 6 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.