Cyclohexanol
| Cyclohexanol[1] | |
|---|---|
 |
 |
| IUPAC name | Cyclohexanol |
| Other names | Cyclohexyl Alcohol, hexahydrophenol, hydrophenol, hydroxycyclohexane, Naxol |
| Identifiers | |
| InChI | InChI=1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 |
| InChIKey | HPXRVTGHNJAIIH-UHFFFAOYAN |
| Standard InChI | InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 |
| Standard InChIKey | HPXRVTGHNJAIIH-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| RTECS | GV7875000 |
| ChemSpider | |
| SMILES | |
| Properties[2] | |
| Chemical formula | C6H12O |
| Molar mass | 100.16 g/mol |
| Appearance | colorless, viscous liquid. Hygroscopic |
| Density | 0.962 g/mL, liquid |
| Melting point |
25.4 °C, 299 K, 78 °F |
| Boiling point |
160.8 °C, 434 K, 321 °F |
| Solubility in water | 4 g/100 mL (20 °C) |
| log P | 1.2 |
| Acidity (pKa) | 16 |
| Refractive index (nD) | 1.465 |
| Viscosity | 41.07 mPa s (30 °C) |
| Hazards[2][3][4] | |
| Material safety data sheet (MSDS) | ICSC |
| EU index number | 603-009-00-3 |
| GHS pictograms | 
|
| GHS signal word | WARNING |
| GHS hazard statements | H332, H302, H335, H315 |
| Flash point | 68 °C (154 ºF) |
| Autoignition temp. | 300 ºC (572 ºF) |
| Explosive limits | 2.4–12% |
| PEL (U.S.) | 50 ppm TWA |
| IDLH level | 400 ppm |
| LD50 | 2.06 g/kg (oral, rat) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Cyclohexanol is the organic compound with the formula (CH2)5CHOH. The molecule is related to cyclohexane ring by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon.[5]
Production
Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:[5]
- C6H12 + 1/2 O2 → C6H11OH
This process co-forms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol:
- C6H5OH + 3 H2 → C6H11OH
This process can also be adjusted to favor the formation of cyclohexanone.
Basic reactions
Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives cyclohexanone, which is converted on a large scale in industry to the oxime, a precursor to caprolactam. As a laboratory exercise, this oxidation can be effected with chromic acid. Esterification affords the commercially useful derivatives dicyclohexyladipate and dicyclohexylphthalate, which are used as plasticizers. Heating in the presence of acid catalysts converts cyclohexanol to cyclohexene.[5]
Applications
As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor to Nylons, but also to various plasticizers. Small amounts are used as a solvent.
Safety
Cyclohexanol is somewhat toxic: the TLV for the vapor for 8 h is 50 ppm.[5] Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.[6]
References
- ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 11th ed.; Merck, 1989. ISBN 091191028X, 2731.
- ↑ 2.0 2.1 Cyclohexanol; International Chemical Safety Card 0243; International Labour Organization: Geneva, November 1988, <http://www.inchem.org/documents/icsc/icsc/eics0243.htm>.
- ↑ Index no. 603-009-00-3 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 477.
- ↑ Cyclohexanol. In Pocket Guide to Chemical Hazards; U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149; Government Printing Office: Washington, DC, 2005. ISBN 9780160727511, <http://www.cdc.gov/niosh/npg/default.html>.
- ↑ 5.0 5.1 5.2 5.3 Tuttle Musser, Michael Cyclohexanol and Cyclohexanone. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2005.
- ↑ Márquez-Rosado, Lucrecia; Trejo-Solís, Cristina; del Pilar Cabrales-Romero, María; Arce-Popoca, Evelia; Sierra-Santoyo, Adolfo; Alemán-Lazarini, Leticia; Fatel-Fazenda, Samia; Carrasco-Legleu, Claudia E., et al. Co-carcinogenic effect of cyclohexanol on the development of preneoplastic lesions in a rat hepatocarcinogenesis model. Mol. Carcinogen. 2007, 46 (7), 524–33. DOI: 10.1002/mc.20295.
External links
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