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Cyclohexanol

Cyclohexanol
Skeletal formula of cyclohexanol
Ball-and-stick model of the cyclohexanol molecule
Names
IUPAC name
Cyclohexanol
Other names
Cyclohexyl Alcohol,
hexahydrophenol,
hydrophenol,
hydroxycyclohexane,
Naxol
Hexalin
Hydralin
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.301
EC Number 203-630-6
KEGG
PubChem CID
RTECS number GV7875000
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 in ethanol, ethyl ether acetone, chloroform
miscible with ethyl acetate, linseed oil, benzene
Vapor pressure 1 mmHg (20°C)
4.40 x 10−6 atm-cu m/mol
Acidity (pKa) 16
-73.40·10−6 cm3/mol
1.4641
Viscosity 41.07 mPa·s (30 °C)
Hazards
Main hazards Flammable, skin irritant
Reacts violently with oxidizing agents
Safety data sheet MSDS for cyclohexanol
R-phrases R20 R22 R37 R38
S-phrases S24 S25
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored 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)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 50 ppm (200 mg/m3)
REL (Recommended)
TWA 50 ppm (200 mg/m3)
IDLH (Immediate danger)
400 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

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 with a camphor-like odor, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon.

Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:

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:

This process can also be adjusted to favor the formation of cyclohexanone.

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.


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