| 1-Hexanol | |
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| IUPAC name |
Hexan-1-ol
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| Other names | hexanol hexyl alcohol |
| Identifiers | |
| CAS number | 111-27-3  |
| PubChem | 8103 |
| EC-number | 203-852-3 |
| RTECS number | MQ4025000 |
| SMILES |
OCCCCCC
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| InChI |
1/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
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| InChI key | ZSIAUFGUXNUGDI-UHFFFAOYAO |
| ChemSpider ID | 7812 |
| Properties[1][2] | |
| Molecular formula | C6H14O |
| Molar mass | 102.17 g/mol |
| Density | 0.8136 g/cm3 (20 ºC) |
| Melting point |
−46.7 °C |
| Boiling point |
158 °C |
| Solubility in water | 0.59 g/100 ml (20 ºC) |
| log P | 2.03 |
| Refractive index (nD) | 1.4178 (20 ºC) |
| Hazards[2] | |
| MSDS | ICSC 1084 |
| EU Index | 603-059-00-6 |
| EU classification | Harmful (Xn) |
| R-phrases | R22 |
| S-phrases | (S2), S24/25 |
| Flash point | 63 °C (145 ºF) |
| Autoignition temperature |
290 ºC (554 ºF) |
| Related compounds | |
| Related primary alcohols | 1-Pentanol 1-Heptanol |
| Related compounds | Hexanal Hexanoic acid |
| (what is this?) (verify) 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 exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. 1-hexanol is believed to be a component of the odour of freshly mowed grass. 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.[3] 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.[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.
See also
Cis-3-Hexenal, another volatile organic carbon biomolecule, also considered responsible for the freshly mowed grass flavor.
References
- ^ Weast, Robert C., ed. (1981), CRC Handbook of Chemistry and Physics (62nd ed.), Boca Raton, FL: CRC Press, p. C-329, ISBN 0-8493-0462-8.
- ^ a b 1-Hexanol, International Chemical Safety Card 1084, Geneva: International Labour Organization, October 2002, http://www.inchem.org/documents/icsc/icsc/eics1084.htm.
- ^ a b Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic", Ullmann’s Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:.
External links
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