1-Hexanol


1-Hexanol
1-Hexanol
Identifiers
CAS number 111-27-3 YesY
PubChem 8103
ChemSpider 7812 YesY
UNII 6CP2QER8GS YesY
EC number 203-852-3
UN number 2282
MeSH 1-Hexanol
ChEMBL CHEMBL14085 N
RTECS number MQ4025000
Beilstein Reference 969167
Jmol-3D images Image 1
Properties
Molecular formula C6H14O
Molar mass 102.17 g mol−1
Exact mass 102.104465070 g mol−1
Density 813.6 mg cm−3
Melting point

-53--41 °C, 220-232 K, -64--42 °F

Boiling point

155-159 °C, 428-432 K, 311-318 °F

Solubility in water 5.9 g dm−3 (at 20 ºC)
log P 1.858
Vapor pressure 100 Pa (at 25.6 ºC)
Refractive index (nD) 1.4178 (at 20 ºC)
Thermochemistry
Std enthalpy of
formation
ΔfHo298
−377.5 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−3.98437 MJ mol−1
Standard molar
entropy
So298
287.4 J K−1 mol−1
Specific heat capacity, C 243.2 J K−1 mol−1
Hazards
MSDS ICSC 1084
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
GHS hazard statements H302
EU Index 603-059-00-6
EU classification Harmful Xn
R-phrases R22
S-phrases (S2), S24/25
NFPA 704
NFPA 704.svg
2
1
0
Flash point 59 °C
Autoignition
temperature
293 ºC
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in the perfume industry.

Contents

Preparation

Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the 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 industrially 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):

Hexene-hexanol.png

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, 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. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8103&loc=ec_rcs. Retrieved 8 October 2011. 
  2. ^ a b Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_279 .

External links


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Look at other dictionaries:

  • Hexanol — may refer to any of the following isomeric organic compounds: *1 Hexanol (n hexanol) *2 Hexanol *3 Hexanolee also* Cyclohexanol …   Wikipedia

  • hexanol — ● hexanol nom masculin Nom générique des alcools dérivés de l hexane. (L hexanol 1 est utilisé dans la préparation d antiseptiques et d hypnotiques.) ● hexanol (synonymes) nom masculin Nom générique des alcools dérivés de l hexane. Synonymes :… …   Encyclopédie Universelle

  • Hexanol — Strukturformel Allgemeines Name Hexanol Andere Namen n Hexanol 1 Hexanol Hexan 1 ol Hexylalkohol Caprona …   Deutsch Wikipedia

  • Hexanol — Le terme hexanol en chimie organique peut faire référence aux 28 isomères en comptant les énantiomères de formule brute C6H14O : Structure Type Nomenclature IUPAC Numéro CAS Température d ébullition (°C) Primaire hexan 1 ol …   Wikipédia en Français

  • hexanol — noun Any of many isomers of the saturated aliphatic alcohol having six carbon atoms …   Wiktionary

  • Hexanol — He|xa|nol 〈n.; s; unz.; Chem.〉 farbloser, brennbarer Alkohol * * * He|xa|nol, hier Hexan 1 ol [↑ ol (1)], das; s; Syn.: Hexylalkohol: C5H11 CH2OH; farblose, brennbare Fl., Sdp. 158 °C, die für Lsgm. u. als Zwischenprodukt für Synthesen gebraucht… …   Universal-Lexikon

  • 1-Hexanol — Hexanol Nombre (IUPAC) siste …   Wikipedia Español

  • 2-Hexanol — Strukturformel …   Deutsch Wikipedia

  • 1-Hexanol — Strukturformel Allgemeines Name Hexanol Andere Namen …   Deutsch Wikipedia

  • N-Hexanol — Strukturformel Allgemeines Name Hexanol Andere Namen n Hexanol 1 Hexanol Hexan 1 ol Hexylalkohol Capronalkohol …   Deutsch Wikipedia


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