2-Ethylhexanol

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2-Ethylhexanol
Skeletal formula of 2-ethylhexanol
2-Ethylhexanol molecule
Identifiers
CAS number 104-76-7 YesY
PubChem 7720, 6991979 R, 6991980 S
ChemSpider 7434 YesY, 5360145 R YesY, 5360146 S YesY
UNII XZV7TAA77P YesY
EC number 203-234-3
KEGG C02498 N
MeSH 2-ethylhexanol
ChEBI CHEBI:16011 YesY
ChEMBL CHEMBL31637 YesY, CHEMBL1229918 YesY
Beilstein Reference 1719280
Jmol-3D images Image 1
Properties
Molecular formula 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)
Refractive index (nD) 1.431
Thermochemistry
Specific
heat capacity
C
317.5J K−1 mol−1
Std molar
entropy
So298
347.0 J K−1 mol−1
Std enthalpy of
formation
ΔfHo298
−433.67–−432.09 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−5.28857–−5.28699 MJ mol−1
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H312, H315, H318, H335
GHS precautionary statements P261, P280, P305+351+338
EU classification Harmful Xn
R-phrases R21, R37/38, R41, R52/53
S-phrases S26, S36/37/39
Flash point 81 °C (178 °F; 354 K)
Explosive limits 0.88–9.7%
LD50
  • 1.97 g kg−1 (dermal, rabbit)
  • 3.73 g kg−1 (oral, rat)
Related compounds
Related alkanol Propylheptyl alcohol
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 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]

Applications[edit]

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[edit]

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.[3][4] 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[edit]

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.[5] 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.[5] According to animal studies, 2-Ethylhexanol does not seem to be carcinogenic.[5]

Nomenclature[edit]

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[edit]

References[edit]

  1. ^ "2-ethylhexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2005. Identification and Related Records. Retrieved 29 January 2012. 
  2. ^ Klaus Rettinger; Christian Burschka; Peter Scheeben; Heike Fuchs; Armin Mosandl (1991). "Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation". Tetrahedron: Asymmetry 2 (10): 965–968. doi:10.1016/S0957-4166(00)86137-6. 
  3. ^ 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.
  4. ^ Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-1
  5. ^ a b c Assessment Report On 2-Ethylhexanol For Developing Ambient Air Quality Objectives Prepared for Alberta Environment by Toxico-Logic Consulting Inc. November 2004

External links[edit]