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2-ethylhexanol

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2-ethylhexanol

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Also known as FEMA 3151, isooctyl alcohol

2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula . It 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 large scale (>2,000,000,000 kg/y) 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 plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer an

Chemical data

Formula
C8H18O
Molecular weight
130.23 g/mol
IUPAC name
2-ethylhexan-1-ol
SMILES
CCCCC(CC)CO
InChIKey
YIWUKEYIRIRTPP-UHFFFAOYSA-N
XLogP
3.1
Polar surface area
20.2 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Wikidata facts

Mass
130.136
Show 5 more facts
chemical formula
C₈H₁₈O
canonical SMILES
CCCCC(CC)CO
Commons category
2-Ethylhexanol
melting point
-70
boiling point
184.62
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~3 min read

Article

7 sections
Contents
  • Properties and applications
  • Industrial production
  • Health effects
  • Nomenclature
  • See also
  • References
  • External links

2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula . It 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 large scale (>2,000,000,000 kg/y) 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 plants, fruits, and wines. 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.

==Properties and applications== The branching in 2-ethylhexanol inhibits crystallization. Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a fatty alcohol, its esters have emollient properties. Representative is the diester bis(2-ethylhexyl) phthalate (DEHP), commonly used in PVC. The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the esterification of three 2-ethylhexanol per trimellitic acid.

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