2-Ethylhexanol

2-Ethylhexanol
IUPAC name 2-Ethyl-1-hexanol
Other names Isooctanol Isooctyl alcohol 2-Ethylhexyl alcohol Oxooctyl alcohol
Identifiers
CAS number	104-76-7 Y
ChemSpider	7434 Y
UNII	XZV7TAA77P Y
KEGG	C02498 Y
ChEBI	CHEBI:16011 Y
ChEMBL	CHEMBL31637 Y
Jmol-3D images	Image 1
SMILES OCC(CC)CCCC
InChI InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 Y Key: YIWUKEYIRIRTPP-UHFFFAOYSA-N Y InChI=1/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 Key: YIWUKEYIRIRTPP-UHFFFAOYAU
Properties
Molecular formula	C8H18O
Molar mass	130.23 g/mol
Density	0.833 g/cm³
Melting point	-76 °C
Boiling point	183-185 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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.

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.^[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.

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.

See also

• Bis(2-ethylhexyl) adipate
• Padimate O
• Octyl salicylate

References

1. ^ 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.
2. ^ Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-1

External links

• National Institute for Occupational Safety and Health (NIOSH)