2-Ethylhexanol
| 2-Ethylhexanol | |
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2-Ethyl-1-hexanol[citation needed] |
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2-Ethylhexan-1-ol[1] |
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Other names
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| Identifiers | |
| CAS number | 104-76-7  |
| PubChem | 7720, 6991979 R, 6991980 S |
| ChemSpider | 7434 , 5360145 R , 5360146 S |
| UNII | XZV7TAA77P |
| EC number | 203-234-3 |
| KEGG | C02498  |
| MeSH | 2-ethylhexanol |
| ChEBI | CHEBI:16011 |
| ChEMBL | CHEMBL31637 , CHEMBL1229918 |
| Beilstein Reference | 1719280 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H18O |
| Molar mass | 130.23 g mol−1 |
| Exact mass | 130.135765198 g mol−1 |
| Appearance | Colourless, transparent liquid |
| Density | 833 mg mL−1 |
| Melting point |
−76 °C, 197 K, -105 °F |
| Boiling point |
180-186 °C, 453-459 K, 356-367 °F |
| log P | 2.721 |
| Vapor pressure | 30 Pa (at 20 °C) |
| Refractive index (nD) | 1.431 |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−433.67–−432.09 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−5.28857–−5.28699 MJ mol−1 |
| Standard molar entropy S |
347.0 J K−1 mol−1 |
| Specific heat capacity, C | 317.5J K−1 mol−1 |
| Hazards | |
| GHS pictograms |   |
| GHS signal word | DANGER |
| GHS hazard statements | H312, H315, H318, H335 |
| GHS precautionary statements | P261, P280, P305+351+338 |
| EU classification |  Xn |
| R-phrases | R21, R37/38, R41, R52/53 |
| S-phrases | S26, S36/37/39 |
| Flash point | 81 °C |
| Explosive limits | 0.88–9.7% |
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| Related compounds | |
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 (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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[edit] Applications
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.
[edit] Industrial production
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.[2][3] 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.
[edit] Nomenclature
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.
[edit] See also
[edit] References
- ^ "2-ethylhexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2005. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7720. Retrieved 29 January 2012.
- ^ C. Kohlpaintner, M. Schulte, J. Falbe, P. Lappe, J. Weber, "Aldehydes, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2008, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_321.pub2.
- ^ Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-1
