Cyclohexanol

Cyclohexanol

Names
IUPAC name Cyclohexanol
Systematic IUPAC name Cyclohexanol
Other names Cyclohexyl alcohol CyOH Hexahydrophenol Hexalin Hydralin Hydrophenol Hydroxycyclohexane Naxol
Properties
Chemical formula	C6H12O (CH2)5CHOH
Molar mass	100.158 g/mol
Appearance	Colorless viscous liquid
Odor	Camphor-like
Density	0.9624 g/cm3 (20 °C)
Melting point	25.93 °C (78.67 °F; 299.08 K)
Boiling point	161.84 °C (323.31 °F; 434.99 K)
Solubility in water	3.60 g/100 ml (20 °C) 4.3 g/100 ml (30 °C)
Solubility	Misicble with acetone, benzene, chloroform, diethyl ether, ethanol, ethyl acetate, linseed oil, toluene, xylene
Vapor pressure	1 mmHg (20 °C)
Acidity (pKa)	16
Thermochemistry
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	67 °C (153 °F; 340 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	1,400 mg/kg (rat, oral) 2,200-2,600 mg/kg (rabbit, oral)
Related compounds
Related compounds	Cyclopentanol Cycloheptanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclohexanol is the organic compound with the formula (CH₂)₅CHOH

Properties

Chemical

Oxidation of cyclohexanol yields cyclohexanone.

Physical

Cyclohexanol is a colorless solid at room temperature, that rapidly melts into a viscous liquid upon gentle heating. It has a camphor-like odor and miscible with organic solvents.

Availability

Cyclohexanol is sold by chemical suppliers. Can also be bought online.

Preparation

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

C₆H₁₂ + ½ 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, using nickel catalyst:

C₆H₅OH + 3 H₂ → C₆H₁₁OH

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

Projects

• Make adipic acid and nylon
• Make cyclohexanone

Handling

Safety

Cyclohexanol is somewhat toxic: the TLV for the vapor for 8 h is 50 ppm. The IDLH concentration is set at 400 ppm, based on studies on the acute oral toxicity in animals.

Due to its high flash point of 67 °C, cyclohexanol is not very flammable and poses a moderate fire hazard.

Storage

Cyclohexanol should be kept in closed bottles, away from oxidizers and flames.

Disposal

Should be mixed with a more flammable solvent and incinerated.

References

Relevant Sciencemadness threads

• Failed synthesis of cyclohexanol from cyclohexene.