| 2-Ethylhexanol | |
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2-Ethyl-1-hexanol |
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Other names
Isooctanol |
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| Identifiers | |
| CAS number | 104-76-7 |
| ChemSpider | 7434 |
| UNII | XZV7TAA77P |
| KEGG | C02498 |
| ChEBI | CHEBI:16011 |
| ChEMBL | CHEMBL31637 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H18O |
| Molar mass | 130.23 g/mol |
| Density | 0.833 g/cm³ |
| Melting point |
−76 °C |
| Boiling point |
183−185 °C |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2-Ethylhexanol (abbreviated 2-EH) is a fatty alcohol, an organic compound is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is nearly insoluble in water but soluble in most organic solvents. It is produced on a massive scale as a precursor to plasticizers, some of which are controversial as potential endocrine disruptors.
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Almost all 2-ethylhexanol is converted into the diesters bis(2-ethylhexyl) phthalate (DEHP), a plasticizer. Because it is a fatty alcohol, its esters tend to have emollient properties. For example, the sunscreen octocrylene contains a 2-ethylhexyl ester for this purpose. It is also commonly used as a low volatility solvent.
2-Ethylhexanol is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde. About 2,500,000 tons are prepared in this way annually.[1][2]. The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol.
Isooctanol and 2-ethylhexanol are not synonyms. According to the Chemical Abstracts Service, isooctanol (CAS# 26952-21-6) refers to a different isomer of octanol, 6-methylheptan-1-ol.