|PubChem||, R, S|
|ChemSpider||, R , S|
|Jmol-3D images||Image 1|
|Molar mass||130.23 g mol−1|
|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|
|Vapor pressure||30 Pa (at 20 °C)|
|Refractive index (nD)||1.431|
heat capacity C
|317.5J K−1 mol−1|
|347.0 J K−1 mol−1|
|Std enthalpy of
|−433.67–−432.09 kJ mol−1|
|Std enthalpy of
|−5.28857–−5.28699 MJ mol−1|
|GHS signal word||DANGER|
|GHS hazard statements||H312, H315, H318, H335|
|GHS precautionary statements||P261, P280, P305+351+338|
|R-phrases||R21, R37/38, R41, R52/53|
|Flash point||81 °C; 178 °F; 354 K|
|Autoignition temperature||290 °C; 554 °F; 563 K|
|Related alkanol||Propylheptyl alcohol|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 poorly soluble 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.
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.
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. 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.
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. 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. According to animal studies, 2-Ethylhexanol does not seem to be carcinogenic.
- "2-ethylhexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2005. Identification and Related Records. 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
- Assessment Report On 2-Ethylhexanol For Developing Ambient Air Quality Objectives Prepared for Alberta Environment by Toxico-Logic Consulting Inc. November 2004