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| Names | |||
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| Preferred IUPAC name Cyclohexanol | |||
| Other names Cyclohexyl Alcohol, hexahydrophenol, hydrophenol, hydroxycyclohexane, Naxol Hexalin Hydralin HOCy | |||
| Identifiers | |||
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3D model (JSmol) | |||
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| ChEMBL | |||
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| DrugBank |
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| ECHA InfoCard | 100.003.301 | ||
| EC Number |
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| Properties | |||
| C6H12O | |||
| Molar mass | 100.158 g/mol | ||
| Appearance | Colorless, viscous liquid. Hygroscopic | ||
| Odor | camphor-like | ||
| Density | 0.9624 g/mL, liquid | ||
| Melting point | 25.93 °C (78.67 °F; 299.08 K) | ||
| Boiling point | 161.84 °C (323.31 °F; 434.99 K) | ||
| 3.60 g/100 mL (20 °C) 4.3 g/100 mL (30 °C) | |||
| Solubility | soluble inethanol,ethyl ether,acetone,chloroform miscible withethyl acetate,linseed oil,benzene | ||
| Vapor pressure | 1 mmHg (20°C)[2] | ||
Henry's law constant (kH) | 4.40 x 10−6 atm-cu m/mol | ||
| Acidity (pKa) | 16 | ||
| −73.40·10−6 cm3/mol | |||
Refractive index (nD) | 1.4641 | ||
| Viscosity | 41.07 mPa·s (30 °C) | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Flammable, skin irritant Reacts violently with oxidizing agents | ||
| GHS labelling: | |||
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| Warning | |||
| H302,H315,H332,H335 | |||
| P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P312,P304+P340,P312,P321,P330,P332+P313,P362,P403+P233,P405,P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 67 °C (153 °F; 340 K) | ||
| 300 °C (572 °F; 573 K) | |||
| Explosive limits | 2.7–12% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 2060 mg/kg (oral, rat) 2200-2600 mg/kg (oral, rabbit)[3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 50 ppm (200 mg/m3)[2] | ||
REL (Recommended) | TWA 50 ppm (200 mg/m3)[2] | ||
IDLH (Immediate danger) | 400 ppm[2] | ||
| Safety data sheet (SDS) | MSDS for cyclohexanol | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Cyclohexanol is theorganic compound with theformula HOCH(CH2)5. The molecule is related tocyclohexane by replacement of one hydrogen atom by ahydroxyl group.[4] This compound exists as adeliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor tonylon.[5]
Cyclohexanol is produced by theoxidation ofcyclohexane in air, typically using cobaltcatalysts:[5]
This process coformscyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production ofadipic acid. The oxidation involves radicals and the intermediacy of thehydroperoxide C6H11O2H.Alternatively, cyclohexanol can be produced by thehydrogenation ofphenol:
This process can also be adjusted to favor the formation of cyclohexanone.
Cyclohexanol undergoes the main reactions expected for asecondary alcohol. Oxidation givescyclohexanone, which is converted on a large scale in industry to theoxime, a precursor tocaprolactam. As a laboratory exercise, this oxidation can be effected withchromic acid.Esterification affords the commercially useful derivatives dicyclohexyladipate and dicyclohexylphthalate, which are used asplasticizers. Heating in the presence of acid catalysts converts cyclohexanol tocyclohexene.[5][6]
Cyclohexanol has at least two solid phases. One of them is aplastic crystal.
As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor tonylons, but also to variousplasticizers. Small amounts are used as asolvent.
Cyclohexanol is moderately toxic: theThreshold Limit Value for the vapor for 8 h is 50ppm.[5] TheIDLH concentration is set at 400 ppm, based on studies on the acute oral toxicity in animals.[7] Few studies have been done on itscarcinogenicity, but one study on rats found it to haveco-carcinogenic effects.[8]
