xiclohexanol

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Cyclohexanol[1]
Skeletal formula of cyclohexanol
Ball-and-stick model of the cyclohexanol molecule
Names
Preferred IUPAC name

Cyclohexanol

Other names

Cyclohexyl Alcohol,
hexahydrophenol,
hydrophenol,
hydroxycyclohexane,
Naxol
Hexalin
Hydralin
HOCy

Identifiers

CAS Number
  • 108-93-0 check

3D model (JSmol)
  • Interactive image
3DMet
  • B00190
ChEBI
  • CHEBI:18099 check
ChEMBL
  • ChEMBL32010 check
ChemSpider
  • 7678 check
DrugBank
  • DB03703 check
ECHA InfoCard 100.003.301 Edit this at Wikidata
EC Number
  • 203-630-6
KEGG
  • C00854 check

PubChem CID
  • 7966
RTECS number
  • GV7875000
UNII
  • 8E7S519M3P check

CompTox Dashboard (EPA)
  • DTXSID4021894 Edit this at Wikidata

InChI

  • InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 check

    Key: HPXRVTGHNJAIIH-UHFFFAOYSA-N check

  • 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)[2]

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

 GHS07: Exclamation mark

Signal word

 Warning
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed vĩ đại relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code

1

2

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)[3]
NIOSH (US health exposure limits):

PEL (Permissible)

 TWA 50 ppm (200 mg/m3)[2]

REL (Recommended)

 TWA 50 ppm (200 mg/m3)[2]

IDLH (Immediate danger)

 400 ppm[2]
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).

check verify (what is check☒ ?)

Infobox references

Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related vĩ đại 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 vĩ đại nylon.[5]

Production[edit]

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 vĩ đại favor the formation of cyclohexanone.

Basic reactions[edit]

Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives cyclohexanone, which is converted on a large scale in industry vĩ đại the oxime, a precursor vĩ đại 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 vĩ đại cyclohexene.[5][6]

Structure[edit]

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

Applications[edit]

As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor vĩ đại nylons, but also vĩ đại various plasticizers. Small amounts are used as a solvent.

Safety[edit]

Cyclohexanol is moderately toxic: the Threshold Limit Value for the vapor for 8 h is 50 ppm.[5] The IDLH concentration is phối 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 vĩ đại have co-carcinogenic effects.[8]

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References[edit]

  1. ^ Merck Index, 11th Edition, 2731.
  2. ^ a b c d NIOSH Pocket Guide vĩ đại Chemical Hazards. "#0165". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Cyclohexanol". Immediately Dangerous vĩ đại Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
  5. ^ a b c d Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  6. ^ G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene". Organic Syntheses. 5: 33. doi:10.15227/orgsyn.005.0033.
  7. ^ CDC - NIOSH Pocket Guide vĩ đại Chemical Hazards
  8. ^ [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.