Cyclohexanol

Cyclohexanol^[1]
Names
	Preferred IUPAC name Cyclohexanol
	Other names Cyclohexyl Alcohol,; hexahydrophenol,; hydrophenol,; hydroxycyclohexane,; Naxol; Hexalin; Hydralin; HOCy
Identifiers
CAS Number	108-93-0 ;
3D model (JSmol)	Interactive image;
3DMet	B00190;
ChEBI	CHEBI:18099 ;
ChEMBL	ChEMBL32010 ;
ChemSpider	7678 ;
DrugBank	DB03703 ;
ECHA InfoCard	100.003.301
EC Number	203-630-6;
KEGG	C00854 ;
PubChem CID	7966;
RTECS number	GV7875000;
UNII	8E7S519M3P ;
CompTox Dashboard (EPA)	DTXSID4021894 ;
	InChI InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 Key: HPXRVTGHNJAIIH-UHFFFAOYSA-N ; InChI=1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 Key: HPXRVTGHNJAIIH-UHFFFAOYAN;
	SMILES C1CCCCC1O;
Properties
Chemical formula	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)
Solubility in water	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)
Henry's law; constant (kH)	4.40 x 10−6 atm-cu m/mol
Acidity (pKa)	16
Magnetic susceptibility (χ)	-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:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H332, H335
Precautionary statements	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)	1 2 0
Flash point	67 °C (153 °F; 340 K)
Autoignition; temperature	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)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 50 ppm (200 mg/m3)
REL (Recommended)	TWA 50 ppm (200 mg/m3)
IDLH (Immediate danger)	400 ppm
Safety data sheet (SDS)	MSDS for cyclohexanol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cyclohexanol is the organic compound with the formula HOCH(CH₂)₅. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group.^[4] This compound exists as a deliquescent 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 to nylon.^[5]

Production

Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:^[5]

2 C₆H₁₂ + O₂ → 2 C₆H₁₁OH

This process coforms 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]^[6]

Structure

Cyclohexanol has at least two solid phases. One of them is a plastic crystal.

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 moderately toxic: the Threshold Limit Value for the vapor for 8 h is 50 ppm.^[5] The IDLH concentration is set at 400 ppm, based on studies on the acute oral toxicity in animals.^[7] Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.^[8]

References

^ Merck Index, 11th Edition, 2731.
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0165". National Institute for Occupational Safety and Health (NIOSH).
^ "Cyclohexanol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
^ ^a ^b ^c ^d Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
^ G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene". Organic Syntheses. 5: 33. doi:10.15227/orgsyn.005.0033.
^ CDC - NIOSH Pocket Guide to Chemical Hazards
^ [1] Lucrecia Márquez-Rosado, Cristina Trejo-Solís 2, María del Pilar Cabrales-Romero, Evelia Arce-Popoca, Adolfo Sierra-Santoyo, Leticia Alemán-Lazarini, Samia Fatel-Fazenda, Claudia E. Carrasco-Legleu, Saúl Villa-Treviño, "Co-carcinogenic effect of cyclohexanol on the development of preneoplastic lesions in a rat hepatocarcinogenesis model", Molecular Carcinogenesis, Vol. 46, No. 7, Pages 524 - 533, March 2007.