2-ethylhexanol

2-Ethylhexanol

Names
IUPAC name 2-Ethylhexan-1-ol
Identifiers
CAS Number	104-76-7 Y
3D model (Jmol)	Interactive image
Beilstein Reference	1719280
ChEBI	CHEBI:16011 Y
ChEMBL	ChEMBL31637 Y ChEMBL1229918 Y
ChemSpider	7434 Y 5360145 R Y 5360146 S Y
ECHA InfoCard	100.002.941
EC Number	203-234-3
KEGG	C02498 N
MeSH	2-ethylhexanol
PubChem	7720 6991979 R 6991980 S
UNII	XZV7TAA77P Y
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
SMILES CCCCC(CC)CO
Properties
Chemical 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
GHS signal word	DANGER
GHS hazard statements	H312, H315, H318, H335
GHS precautionary statements	P261, P280, P305+351+338
EU classification (DSD)	Xn
R-phrases	R21, R37/38, R41, R52/53
S-phrases	S26, S36/37/39
Flash point	81 °C (178 °F; 354 K)
Autoignition temperature	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	2-Methylhexane 3-Methylhexane Valnoctamide 2-Methylheptane 3-Methylheptane Valpromide 2-Ethylhexanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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.

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.