1-Hexanol

1-Hexanol
Names
IUPAC name
Hexan-1-ol[1]
Identifiers
3D model (JSmol)
969167
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 102.18 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
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 codeNFPA 704 four-colored diamond
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

1-Hexanol 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.

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):

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. 1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. 1 2 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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