View source for Cyclohexanol

{{chembox
|Watchedfields = changed
|verifiedrevid = 443680043
|Reference=<ref>''[[Merck Index]]'', 11th Edition, '''2731'''.</ref>
|Name = Cyclohexanol
|ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageFileL1 = Cyclohexanol.svg
|ImageSizeL1 = 80px
|ImageAltL1 = Skeletal formula of cyclohexanol
|ImageFileR1 = Cyclohexanol molecule ball from xtal.png
|ImageSizeR1 = 130px
|ImageAltR1 = Ball-and-stick model of the cyclohexanol molecule
|ImageFile2 = Cyclohexanol-from-xtal-3D-bs-17.png
|ImageSize2 = 130px
|PIN = Cyclohexanol
|OtherNames = Cyclohexyl Alcohol,<br />hexahydrophenol,<br />hydrophenol,<br />hydroxycyclohexane,<br />Naxol<br/>Hexalin<br/>Hydralin<br/>HOCy
|Section1={{Chembox Identifiers
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 18099
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB03703
|SMILES = C1CCCCC1O
|PubChem = 7966
|CASNo = 108-93-0
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 8E7S519M3P
|RTECS = GV7875000
|EC_number = 203-630-6
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 7678
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C00854
|3DMet = B00190
|InChI = 1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 32010
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
|InChIKey = HPXRVTGHNJAIIH-UHFFFAOYAN
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = HPXRVTGHNJAIIH-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|Formula = C<sub>6</sub>H<sub>12</sub>O
|MolarMass = 100.158 g/mol
|Appearance = Colorless, viscous liquid.<br />[[Hygroscopic]]
|Odor = [[camphor]]-like
|Density = 0.9624 g/mL, liquid
|Solubility = 3.60 g/100 mL (20 °C) <br> 4.3 g/100 mL (30 °C)
|SolubleOther = soluble in [[ethanol]], [[ethyl ether]], [[acetone]], [[chloroform]] <br> miscible with [[ethyl acetate]], [[linseed oil]], [[benzene]]
|MeltingPtC = 25.93
|BoilingPtC = 161.84
|pKa = 16
|Viscosity = 41.07 mPa·s (30 °C)
|RefractIndex = 1.4641
|HenryConstant = 4.40 x 10<sup>−6</sup> atm-cu m/mol 
|VaporPressure = 1 mmHg (20°C)<ref name=PGCH/>
|MagSus = −73.40·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Hazards
|ExternalSDS = [http://ptcl.chem.ox.ac.uk/MSDS/CY/cyclohexanol.html MSDS for cyclohexanol]
|MainHazards = Flammable, skin irritant<br />Reacts violently with oxidizing agents
|NFPA-H = 1 | NFPA-F = 2 | NFPA-R = 0
|FlashPtC = 67
|AutoignitionPtC = 300
|ExploLimits = 2.7–12%
|LD50 = 2060 mg/kg (oral, rat)<br/>2200-2600 mg/kg (oral, rabbit)<ref>{{IDLH|108930|Cyclohexanol}}</ref>
|GHSPictograms = {{GHS07}}
|GHSSignalWord = Warning
|HPhrases = {{H-phrases|302|315|332|335}}
|PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|312|321|330|332+313|362|403+233|405|501}}
|PEL = TWA 50 ppm (200 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0165}}</ref>
|IDLH = 400 ppm<ref name=PGCH/>
|REL = TWA 50 ppm (200 mg/m<sup>3</sup>)<ref name=PGCH/>
}}
}}

'''Cyclohexanol''' is the [[organic compound]] with the [[Chemical formula|formula]] HOCH(CH<sub>2</sub>)<sub>5</sub>. The molecule is related to [[cyclohexane]] by replacement of one hydrogen atom by a [[hydroxide|hydroxyl group]].<ref>{{RubberBible86th}}</ref> 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]].<ref name=Ullmann>Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref>

==Production==
Cyclohexanol is produced by the [[oxidation]] of [[cyclohexane]] in air, typically using cobalt [[catalyst]]s:<ref name=Ullmann/>
:2 C<sub>6</sub>H<sub>12</sub> + O<sub>2</sub> → 2 C<sub>6</sub>H<sub>11</sub>OH
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]] C<sub>6</sub>H<sub>11</sub>O<sub>2</sub>H.
Alternatively, cyclohexanol can be produced by the [[hydrogenation]] of [[phenol]]:
:C<sub>6</sub>H<sub>5</sub>OH + 3 H<sub>2</sub> → C<sub>6</sub>H<sub>11</sub>OH
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 [[plasticizer]]s. Heating in the presence of acid catalysts converts cyclohexanol to [[cyclohexene]].<ref name=Ullmann/><ref>{{cite journal |doi=10.15227/orgsyn.005.0033|title=Cyclohexene|journal=Organic Syntheses|year=1925|volume=5|page=33|author=G. H. Coleman, H. F. Johnstone}}</ref>

==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 [[nylon]]s, 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 [[Parts per million|ppm]].<ref name=Ullmann/> The [[IDLH]] concentration is set at 400 ppm, based on studies on the acute oral toxicity in animals.<ref>[https://www.cdc.gov/niosh/npg/npgd0165.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref> Few studies have been done on its [[carcinogenicity]], but one study on rats found it to have [[co-carcinogenic]] effects.<ref>[https://archive.today/20130105121729/http://www3.interscience.wiley.com/journal/114178183/abstract?CRETRY=1&SRETRY=0] 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.</ref>

==References==
<references/>

{{Alcohols}}
{{Chemical agents}}


[[Category:Cyclohexyl compounds]]
[[Category:Cyclohexanols]]
[[Category:Nerve agent precursors]]