1-Hexanol
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1-Hexanol
| 1-Hexanol | |
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Hexan-1-ol[1] |
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| Identifiers | |
| CAS number | 111-27-3  |
| PubChem | 8103 |
| ChemSpider | 7812 |
| UNII | 6CP2QER8GS |
| EC number | 203-852-3 |
| UN number | 2282 |
| MeSH | 1-Hexanol |
| ChEMBL | CHEMBL14085 |
| RTECS number | MQ4025000 |
| Beilstein Reference | 969167 |
| Jmol-3D images | Image 1 |
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| 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 ΔfH |
−377.5 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−3.98437 MJ mol−1 |
| Standard molar entropy S |
287.4 J K−1 mol−1 |
| Specific heat capacity, C | 243.2 J K−1 mol−1 |
| Hazards | |
| MSDS | ICSC 1084 |
| GHS pictograms |  |
| GHS signal word | WARNING |
| GHS hazard statements | H302 |
| EU Index | 603-059-00-6 |
| EU classification |  Xn |
| R-phrases | R22 |
| S-phrases | (S2), S24/25 |
| NFPA 704 |
 2
1
0
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| Flash point | 59 °C |
| Autoignition temperature |
293 ºC |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 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.
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Contents
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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 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-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.
- ^ 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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