1-Hexanol

1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in the perfume industry.

1-Hexanol
Skeletal formula of 1-hexanol
Spacefill formula of 1-hexanol
Names
IUPAC name
Hexan-1-ol[1]
Identifiers
3D model (JSmol)
969167
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.503
EC Number
  • 203-852-3
MeSH 1-Hexanol
RTECS number
  • MQ4025000
UNII
UN number 2282
Properties
C6H14O
Molar mass 102.177 g·mol−1
Density 0.82 g cm−3 (at 20 °C)[2]
Melting point −45 °C (−49 °F; 228 K)[2]
Boiling point 157 °C (315 °F; 430 K)[2]
5.9 g/L (at 20 °C)[2]
log P 1.858
Vapor pressure 100 Pa (at 25.6 °C)
1.4178 (at 20 °C)
Thermochemistry
243.2 J K−1 mol−1
287.4 J K−1 mol−1
−377.5 kJ mol−1
−3.98437 MJ mol−1
Hazards
Safety data sheet ICSC 1084
GHS pictograms
GHS Signal word Warning
H302
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 59 °C (138 °F; 332 K)
293 °C (559 °F; 566 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products.[3] An idealized synthesis is shown:

Al(C2H5)3 + 6C2H4 → Al(C6H13)3
Al(C6H13)3 + ​1 1⁄2O2 + 3H2O → 3HOC6H13 + Al(OH)3

The process generates a range of oligomers that are separated by distillation.

Alternative methods

Another method of preparation entails hydroformylation of 1-pentene followed by hydrogenation of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C6-alcohols, which are precursors to plasticizers.[3]

In principle, 1-hexene could be converted to 1-hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide):

Hexan-1-ol

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ethylene.

Occurrence in nature

1-Hexanol is believed to be a component of the odour of freshly mown grass. Alarm pheromones emitted by the Koschevnikov gland of honey bees contain 1-hexanol.

See also

Cis-3-Hexenal, another volatile organic compound, is also considered responsible for the freshly mowed grass flavor.

References
  1. "1-hexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 8 October 2011.
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter. "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_279..
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