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2-Ethylhexanol

2-Ethylhexanol
Skeletal formula of 2-ethylhexanol
2-Ethylhexanol molecule
Names
IUPAC name
2-Ethylhexan-1-ol
Identifiers
104-76-7 YesY
3D model (Jmol) Interactive image
1719280
ChEBI CHEBI:16011 YesY
ChEMBL ChEMBL31637 YesY
ChEMBL1229918 YesY
ChemSpider 7434 YesY
5360145 R YesY
5360146 S YesY
ECHA InfoCard 100.002.941
EC Number 203-234-3
KEGG C02498 N
MeSH 2-ethylhexanol
PubChem 7720
6991979 R
6991980 S
UNII XZV7TAA77P YesY
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)
1.431
Thermochemistry
317.5J K−1 mol−1
347.0 J K−1 mol−1
−433.67–−432.09 kJ mol−1
−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
H312, H315, H318, H335
P261, P280, P305+351+338
Harmful Xn
R-phrases R21, R37/38, R41, R52/53
S-phrases S26, S36/37/39
Flash point 81 °C (178 °F; 354 K)
290 °C (554 °F; 563 K)
Explosive limits 0.88–9.7%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 1.97 g kg−1(dermal, rabbit)
  • 3.73 g kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
none
REL (Recommended)
TWA 50 ppm (270 mg/m3) [skin]
IDLH (Immediate danger)
N.D.
Related compounds
Related alkanol
Propylheptyl alcohol
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
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.

Almost all 2-ethylhexanol manufactured is used as a precursor for the synthesis of the diester bis(2-ethylhexyl) phthalate (DEHP), a plasticizer. Because it is a fatty alcohol, its esters tend to have emollient properties. For example, the sunscreen 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.

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.

Synthesis of 2-Ethylhexanol

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. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.


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