2-Ethylhexanol
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| 2-Ethylhexanol molecule | |
| Names | |
|---|---|
| IUPAC name
2-Ethylhexan-1-ol[1]
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| Identifiers | |
104-76-7  |
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| 1719280 | |
| ChEBI | CHEBI:16011 |
| ChEMBL | ChEMBL31637 ChEMBL1229918 |
| ChemSpider | 7434 5360145 R 5360146 S |
| EC Number | 203-234-3 |
| Jmol 3D model | Interactive image |
| KEGG | C02498  |
| MeSH | 2-ethylhexanol |
| PubChem | 7720 6991979 R 6991980 S |
| UNII | XZV7TAA77P |
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| Properties | |
| C8H18O | |
| Molar mass | 130.23 g·mol−1 |
| Appearance | Colourless liquid |
| Density | 833 mg mL−1 |
| Melting point | −76 °C (−105 °F; 197 K) |
| Boiling point | 180 to 186 °C; 356 to 367 °F; 453 to 459 K |
| log P | 2.721 |
| Vapor pressure | 30 Pa (at 20 °C) |
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Refractive index (nD)
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1.431 |
| Thermochemistry | |
| 317.5J K−1 mol−1 | |
|
Std molar
entropy (S |
347.0 J K−1 mol−1 |
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Std enthalpy of
formation (ΔfH |
−433.67–−432.09 kJ mol−1 |
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Std enthalpy of
combustion (ΔcH |
−5.28857–−5.28699 MJ mol−1 |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related alkanol
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Propylheptyl alcohol |
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
2-Ethylhexanol (abbreviated 2-EH) 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 massive scale 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 natural plant fragrances, and 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.[2]
Contents
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. 2-Ethylhexanol can also be used as an octane booster when reacted with nitric acid.
Industrial production
2-Ethylhexanol is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.[3] About 2,500,000 tons are prepared in this way annually.[4][5] 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.
Health effects
Air exposure of 2-ethylhexanol to a human in a case study involving concentrations between 80 and 470 μg/m3 included throat irritation, cough, sore eyes, headache and blurred vision. Other volatile organic compounds were detected in the air as well, but 2-ethylhexanol was of the highest concentration.[6] Another study involving several people exposed to 2-ethylhexanol reported headaches, dizziness, fatigue and gastrointestinal disorders, but the concentration of 2-ethylhexanol in this case is not known.[6] According to animal studies, 2-ethylhexanol does not seem to be carcinogenic.[6]
Nomenclature
Isooctanol and 2-ethylhexanol are not synonyms. According to the Chemical Abstracts Service, isooctanol (CAS# 26952-21-6) refers to an isomer of octanol, 6-methylheptan-1-ol.
See also
References
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- ↑ 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 4180-4181.
- ↑ 6.0 6.1 6.2 Assessment Report On 2-Ethylhexanol For Developing Ambient Air Quality Objectives Prepared for Alberta Environment by Toxico-Logic Consulting Inc. November 2004.
