Cyclohexanol

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Cyclohexanol
Names
IUPAC name
Cyclohexanol
Systematic IUPAC name
Cyclohexanol
Other names
Cyclohexyl alcohol
CyOH
Hexahydrophenol
Hexalin
Hydralin
Hydrophenol
Hydroxycyclohexane
Naxol
Properties
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)
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):
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:[1]

C6H5OH + 3 H2 → C6H11OH

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

Projects

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

  1. https://www.prepchem.com/synthesis-of-cyclohexanol/

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