Difference between revisions of "Cyclohexanol"

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(Imported from http://en.wikipedia.org/w/index.php?title=Cyclohexanol&oldid=308307711)
 
 
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{{chembox
 
{{chembox
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|  Reference=<ref>''[[Merck Index]]'', 11th Edition, '''2731'''.</ref>
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|  Reference=<ref>{{Merck11th|2731}}.</ref>
 
|  Name = Cyclohexanol
 
|  Name = Cyclohexanol
 
|  ImageFileL1 = Cyclohexanol acsv.svg
 
|  ImageFileL1 = Cyclohexanol acsv.svg
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   }}
 
   }}
 
| Section2 = {{Chembox Properties
 
| Section2 = {{Chembox Properties
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|  Reference = <ref name="ICSC">{{ICSC-ref|02|43|name=Cyclohexanol|date=November 1988}}.</ref>
 
|  Formula = C<sub>6</sub>H<sub>12</sub>O
 
|  Formula = C<sub>6</sub>H<sub>12</sub>O
 
|  MolarMass = 100.16 g/mol
 
|  MolarMass = 100.16 g/mol
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|  Appearance = Colorless, viscous liquid.<br />[[Hygroscopic]]
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|  Appearance = colorless, viscous liquid.<br />[[Hygroscopic]]
 
|  Density = 0.962 g/mL, liquid
 
|  Density = 0.962 g/mL, liquid
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|  Solubility = 3.60 g/100 mL (20 °C)
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|  Solubility = 4 g/100 mL (20 °C)
 
|  MeltingPtC = 25.4
 
|  MeltingPtC = 25.4
 
|  BoilingPtC = 160.8
 
|  BoilingPtC = 160.8
 
|  pKa = 16
 
|  pKa = 16
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|  pKb =
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|  Viscosity = 41.07 mPa&thinsp;s (30 °C)
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|  Viscosity = 41.07 mPa·s (30 °C)
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|  LogP = 1.2
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|  RefractIndex = 1.465
 
   }}
 
   }}
 
| Section7 = {{Chembox Hazards
 
| Section7 = {{Chembox Hazards
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|  ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/CY/cyclohexanol.html MSDS for cyclohexanol]
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|  Reference = <ref name="ICSC"/><ref>{{CLP Regulation|index=603-009-00-3|page=477}}</ref><ref>{{PGCH-ref|0165|name=Cyclohexanol}}.</ref>
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|  MainHazards = Flammable, skin irritant<br />Reacts violently with oxidizing agents
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|  ExternalMSDS = {{ICSC-small|02|43}}
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|  FlashPt = 67 °C
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|  EUIndex = 603-009-00-3
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|  GHSPictograms = {{GHS07|Acute Tox. 4; STOT SE 3; Skin Irrit. 2}}
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|  GHSSignalWord = WARNING
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|  HPhrases = {{H-phrases|332|302|335|315}}
 +
|  FlashPt = 68 °C (154 ºF)
 +
|  Autoignition = 300 ºC (572 ºF)
 +
|  ExploLimits = 2.4–12%
 +
|  PEL = 50 ppm TWA
 +
|  IDLH = 400 ppm
 
|  LD50 = 2.06 g/kg (oral, rat)
 
|  LD50 = 2.06 g/kg (oral, rat)
−
|  RPhrases = {{R20}} {{R22}} {{R37}} {{R38}}
 
−
|  SPhrases = {{S24}} {{S25}}
 
 
   }}
 
   }}
 
}}
 
}}
  
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'''Cyclohexanol''' is the [[organic compound]] with the [[Chemical formula|formula]] ([[carbon|C]][[hydrogen|H]]<sub>2</sub>)<sub>5</sub>CHOH. The molecule is related to [[cyclohexane]] ring by replacement of one hydrogen atom by a [[hydroxide|hydroxyl group]].<ref>{{RubberBible86th}}</ref> This compound exists as a [[deliquescent]] colorless solid, which, when very pure, melts near room temperature.  Billions of kilograms 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>
+
'''Cyclohexanol''' is the [[organic compound]] with the [[Chemical formula|formula]] ([[carbon|C]][[hydrogen|H]]<sub>2</sub>)<sub>5</sub>CHOH. The molecule is related to [[cyclohexane]] ring by replacement of one hydrogen atom by a [[hydroxide|hydroxyl group]]. This compound exists as a [[deliquescent]] colorless solid, which, when very pure, melts near room temperature.  Billions of kilograms are produced annually, mainly as a precursor to [[nylon]].<ref name=Ullmann>{{citation | first = Michael | last = Tuttle Musser | contribution = Cyclohexanol and Cyclohexanone | title = Ullmann's Encyclopedia of Industrial Chemistry | publisher = Wiley-VCH | location = Weinheim | year = 2005}}.</ref>
  
 
==Production==
 
==Production==
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==Safety==
 
==Safety==
−
Cyclohexanol is somewhat toxic: the [[Threshold Limit Value|TLV]] for the vapor for 8 h is 50 [[ppm]].<ref name=Ullmann/>  Few studies have been done on its [[carcinogenicity]], but one study on rats found it to have [[co-carcinogenic]] effects.<ref>[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>
+
Cyclohexanol is somewhat toxic: the [[Threshold Limit Value|TLV]] for the vapor for 8 h is 50 [[ppm]].<ref name=Ullmann/>  Few studies have been done on its [[carcinogenicity]], but one study on rats found it to have [[co-carcinogenic]] effects.<ref>{{citation | first1 = Lucrecia | last1 = Márquez-Rosado | first2 = Cristina | last2 = Trejo-Solís | first3 = María | last3 = del Pilar Cabrales-Romero | first4 = Evelia | last4 = Arce-Popoca | first5 = Adolfo | last5 = Sierra-Santoyo | first6 = Leticia | last6 = Alemán-Lazarini | first7 = Samia | last7 = Fatel-Fazenda | first8 = Claudia E. | last8 = Carrasco-Legleu | first9 = Saúl | last9 = Villa-Treviño | title = Co-carcinogenic effect of cyclohexanol on the development of preneoplastic lesions in a rat hepatocarcinogenesis model | journal = Mol. Carcinogen. | year = 2007 | volume = 46 | issue = 7 | pages = 524–33 | doi = 10.1002/mc.20295}}.</ref>
  
 
==References==
 
==References==
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<references/>
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{{reflist}}
  
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{{Alcohols}}
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==External links==
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<!--Refractive index = 1.465-->
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*{{ICSC|02|43}}
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*{{PGCH|0165}}
  
 
[[Category:Alcohols]]
 
[[Category:Alcohols]]
  
 
{{Imported from Wikipedia|name=Cyclohexanol|id=308307711}}
 
{{Imported from Wikipedia|name=Cyclohexanol|id=308307711}}

Latest revision as of 09:22, 22 August 2009

Cyclohexanol[1]
Cyclohexanol
Cyclohexanol
IUPAC name Cyclohexanol
Other names Cyclohexyl Alcohol,
hexahydrophenol,
hydrophenol,
hydroxycyclohexane,
Naxol
Identifiers
InChI InChI=1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
InChIKey HPXRVTGHNJAIIH-UHFFFAOYAN
Standard InChI InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
Standard InChIKey HPXRVTGHNJAIIH-UHFFFAOYSA-N
CAS number [108-93-0]
EC number 203-630-6
RTECS GV7875000
ChemSpider 7678
SMILES
Properties[2]
Chemical formula C6H12O
Molar mass 100.16 g/mol
Appearance colorless, viscous liquid.
Hygroscopic
Density 0.962 g/mL, liquid
Melting point

25.4 °C, 299 K, 78 °F

Boiling point

160.8 °C, 434 K, 321 °F

Solubility in water 4 g/100 mL (20 °C)
log P 1.2
Acidity (pKa) 16
Refractive index (nD) 1.465
Viscosity 41.07 mPa s (30 °C)
Hazards[2][3][4]
Material safety data sheet (MSDS) ICSC 0243
EU index number 603-009-00-3
GHS pictograms Acute Tox. 4; STOT SE 3; Skin Irrit. 2
GHS signal word WARNING
GHS hazard statements H332, H302, H335, H315
Flash point 68 °C (154 ºF)
Autoignition temp. 300 ºC (572 ºF)
Explosive limits 2.4–12%
PEL (U.S.) 50 ppm TWA
IDLH level 400 ppm
LD50 2.06 g/kg (oral, rat)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

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, which, when very pure, melts near room temperature. Billions of kilograms 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]

C6H12 + 1/2 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:

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]

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 somewhat toxic: the TLV for the vapor for 8 h is 50 ppm.[5] Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.[6]

References

  1. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 11th ed.; Merck, 1989. ISBN 091191028X, 2731.
  2. ↑ 2.0 2.1 Cyclohexanol; International Chemical Safety Card 0243; International Labour Organization: Geneva, November 1988, <http://www.inchem.org/documents/icsc/icsc/eics0243.htm>.
  3. ↑ Index no. 603-009-00-3 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 477.
  4. ↑ Cyclohexanol. In Pocket Guide to Chemical Hazards; U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149; Government Printing Office: Washington, DC, 2005. ISBN 9780160727511, <http://www.cdc.gov/niosh/npg/default.html>.
  5. ↑ 5.0 5.1 5.2 5.3 Tuttle Musser, Michael Cyclohexanol and Cyclohexanone. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2005.
  6. ↑ Márquez-Rosado, Lucrecia; Trejo-Solís, Cristina; del Pilar Cabrales-Romero, María; Arce-Popoca, Evelia; Sierra-Santoyo, Adolfo; Alemán-Lazarini, Leticia; Fatel-Fazenda, Samia; Carrasco-Legleu, Claudia E., et al. Co-carcinogenic effect of cyclohexanol on the development of preneoplastic lesions in a rat hepatocarcinogenesis model. Mol. Carcinogen. 2007, 46 (7), 524–33. DOI: 10.1002/mc.20295.

External links

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