1-Hexanol

1-Hexanol

1-Hexanol
Skeletal formula of 1-hexanol
Spacefill formula of 1-hexanol
Names
IUPAC name
Hexan-1-ol[1]
Identifiers
 Y
969167
ChEMBL  Y
ChemSpider  Y
EC number 203-852-3
Jmol-3D images Image
MeSH
PubChem
RTECS number MQ4025000
UNII  Y
UN number 2282
Properties
C6H14O
Molar mass 102.18 g·mol−1
Density .8136 g cm−3
Melting point −53 to −41 °C; −64 to −42 °F; 220 to 232 K
Boiling point 155 to 159 °C; 311 to 318 °F; 428 to 432 K
5.9 g/L (at 20 °C)
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 The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H302
Harmful Xn
R-phrases R22
S-phrases (S2), S24/25
NFPA 704
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).
 Y  (: Y/N?)

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.

Contents

  • Preparation 1
    • Alternative methods 1.1
  • Occurrence in Nature 2
  • See also 3
  • References 4
  • External links 5

Preparation

Hexanol is produced industrially by the oligomerization of alkylaluminium products.[2] An idealized synthesis is shown:

Al(C2H5)3 + 6C2H4 → Al(C6H13)3
Al(C6H13)3 + 1½O2 + 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.[2]

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 carbon biomolecule, 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. ^ a b Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic",  .

External links

  • International Chemical Safety Card 1084