Cyclohexanol

Cyclohexanol[1] | Skeletal formula of cyclohexanol | Ball-and-stick model of the cyclohexanol molecule

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Names
Preferred IUPAC name

Cyclohexanol

Other names

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

Identifiers

CAS Number

* 108-93-0 Y

3D model (JSmol)

* Interactive image

3DMet  |

* B00190

ChEBI |

* CHEBI:18099 Y

ChEMBL |

* ChEMBL32010 Y

ChemSpider |

* 7678 Y

DrugBank |

* DB03703 Y

EC Number |

* 203-630-6

KEGG |

* C00854 Y

PubChem CID

* 7966

RTECS number |

* GV7875000

UNII |

* 8E7S519M3P Y

InChI

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

Key: HPXRVTGHNJAIIH-UHFFFAOYSA-N Y

* 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
Main hazards | Flammable, skin irritant
Reacts violently with oxidizing agents
Safety data sheet | MSDS for cyclohexanol
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H302, H315, H332, H335

GHS precautionary statements

| P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P321, P330, P332+313, P362, P403+233, P405, P501
NFPA 704 (fire diamond)  |

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]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet
* PairSizeSet

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]

## Contents

* 1 Production
* 2 Basic reactions
* 3 Structure
* 4 Applications
* 5 Safety
* 6 References

## 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

1. ↑ Merck Index, 11th Edition, 2731.
2. ↑ 2.0 2.1 2.2 2.3 NIOSH Pocket Guide to Chemical Hazards. "#0165". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0165.html.
3. ↑ "Cyclohexanol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/108930.html.
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. ↑ 5.0 5.1 5.2 5.3 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 to 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.

* v
* t
* e

Alcohols

Straight-chain
primary
alcohols (1°)|

* Methanol (C1)
* Ethanol (C2)
* 1-Propanol (C3)
* n-Butanol (C4)
* 1-Pentanol (C5)
* 1-Hexanol (C6)
* 1-Heptanol (C7)
* 1-Octanol (C8)
* 1-Nonanol (C9)
* 1-Decanol (C10)
* Undecanol (C11)
* Dodecanol (C12)
* Tridecan-1-ol (C13)
* 1-Tetradecanol (C14)
* 1-Pentadecanol (C15)
* Cetyl alcohol (C16)
* Heptadecan-1-ol (C17)
* Stearyl alcohol (C18)
* Nonadecan-1-ol (C19)
* Arachidyl alcohol (C20)
* Heneicosan-1-ol (C21)
* Docosanol (C22)
* Tricosan-1-ol (C23)
* 1-Tetracosanol (C24)
* Pentacosan-1-ol (C25)
* 1-Hexacosanol (C26)
* 1-Heptacosanol (C27)
* 1-Octacosanol (C28)
* 1-Nonacosanol (C29)
* Triacontanol (C30)
* Hentriacontanol (C31)
* Dotriacontanol (C32)
* Tritriacontanol (C33)
* Tetratriacontanol (C34)
* Pentatriacontanol (C35)
* Hexatriacontanol (C36)
* 1-Heptatriacontanol (C37)
* 1-Octatriacontanol (C38)
* Nonatriacontan-1-ol (C39)
* Tetracontanol (C40)

Other primary
alcohols|

* Isobutanol (C4)
* Isoamyl alcohol (C5)
* 2-Methyl-1-butanol (C5)
* Phenethyl alcohol (C8)
* Tryptophol (C10)

Secondary
alcohols (2°)|

* Isopropanol (C3)
* Cyclopropanol (C3)
* 2-Butanol (C4)
* 2-Pentanol (C5)
* 3-Pentanol (C5)
* Cyclopentanol (C5)
* 2-Hexanol (C6)
* 3-Hexanol (C6)
* Pinacolyl alcohol (C6)
* Cyclohexanol (C6)
* 2-Heptanol (C7)
* 3-Heptanol (C7)
* 2-Octanol (C8)

Tertiary
alcohols (3°)|

* tert-Butyl alcohol (C4)
* tert-Amyl alcohol (C5)
* 2-Methyl-2-pentanol (C6)
* 2-Methylhexan-2-ol (C7)
* 2-Methylheptan-2-ol (C8)
* 3-Methyl-3-pentanol (C6)
* 3-Methyloctan-3-ol (C9)

Preparations|

* Substitution of haloalkane
* Carbonyl reduction
* Ether cleavage
* Hydrolysis of epoxide
* Hydration of alkene
* Ziegler process

Reactions|

* Deprotonation
* Protonation
* Alcohol oxidation
* Glycol cleavage
* Nucleophilic substitution
* Fischer–Speier esterification
* Williamson ether synthesis
* Elimination reaction
* Nucleophilic substitution of carbonyl group
* Friedel-Crafts alkylation
* Nucleophilic conjugate addition
* Transesterification

* Category

* v
* t
* e

* Agents used in chemical warfare
* incapacitation
* riot control

Blood|

* Cyanogen
* Cyanogen bromide
* Cyanogen chloride (CK)
* Hydrogen cyanide (AC)
* Arsine
* Vinyl arsine

Blister|

* Arsenicals
* Ethyldichloroarsine (ED)
* Methyldichloroarsine (MD)
* Phenyldichloroarsine (PD)
* Lewisite (L)
* Mustard gas (HD H HT HL HQ)
* Nitrogen mustard
* HN1
* HN2
* HN3
* TL-301
* Nitrosocarbamates
* KB-16

Nerve|

| G-agents|

* Tabun (GA)
* Sarin (GB)
* Chlorosarin (GC)
* Soman (GD)
* Ethylsarin (GE)
* Cyclosarin (GF)
* GH
* GJ
* GK
* GL
* GM
* GN
* GO
* GP
* GQ
* GR
* GS
* GT
* GU
* Fluorotabun
* GV
* GV1
* GV2
* GV3
* GV4
* GV5
* GV6
* EA-1356
* EA-3534
* EA-4352
* EA-5414
* EA-5488
* Thiosarin
* Thiosoman
* Thiocyclosarin
* Crotylsarin

|

V-agents|

* EA-2192
* EA-3148
* EA-3317
* VD
* VE
* VF
* VG
* VH
* VJ
* VK
* VL
* VM
* VN
* VO
* VP
* VQ
* VR
* VS
* VT
* VU
* VV
* VW
* VY
* VZ
* VX
* V1
* V2
* V3
* V4
* V5
* V6
* IVX
* IIVx
* Chinese VX
* V-sub x (GD-7)

Novichok agents|

* A-230
* A-232
* A-234
* A-242
* A-262
* C01-A035
* C01-A039
* C01-A042

Carbamates|

* EA-3887
* EA-3887A
* EA-3948
* EA-3966
* EA-3990
* EA-4026
* EA-4038
* EA-4048
* EA-4056
* EA-4057
* EA-4181
* T-1123
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)

Other|

* EA-2012
* EA-2054
* EA-2098
* EA-2613
* 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Neopentylene fluorophosphate

Precursors|

* Chlorosarin
* Chlorosoman
* Cyclohexanol
* 1,8-Dibromooctane
* N,N-Diisopropylaminoethanol
* Dimethylamidophosphoric dichloride
* Dimethylamidophosphoric dicyanide
* Isopropyl alcohol
* Methyldichlorophosphine
* Methylphosphonic acid dichloride
* Methylphosphonyl difluoride
* Pinacolone
* Pinacolyl alcohol
* QL
* 3,3,5-Trimethylcyclohexanol

Neurotoxins|

* Saxitoxin (TZ)
* Botulinum toxin (BTX)
* Tetanospasmin (TeNT)
* Chlorophenylsilatrane
* Tetrodotoxin

Nettle|

* Phosgene oxime (CX)

Pulmonary/Choking agent|

* Chlorine
* Phosgene (CG)
* Perfluoroisobutene
* Chloropicrin (PS)
* Diphosgene (DP)
* Disulfur decafluoride
* Acrolein
* Ethyl bromoacetate
* Perchloromethyl mercaptan

Vomiting agent|

* Adamsite
* Chloropicrin
* Diphenylchlorarsine
* Diphenylcyanoarsine
* Diphenylaminecyanoarsine

Incapacitating|

* Agent 15 (BZ)
* Dimethylheptylpyran (DMHP)
* EA-3167
* EA-3443
* EA-3580
* EA-3834
* Kolokol-1
* LSD-25
* PAVA spray
* Sleeping gas

Riot control|

* Xylyl bromide
* Pepper spray (OC)
* Mace (spray)
* CN
* CS
* CR
* CNS

Other|

* Methyl fluoroacetate
* Fluoroethyl fluoroacetate
* Ricin
* Abrin
* Enterotoxin type B
* Depleted uranium
* post-combustion uranium oxides

* List of chemical warfare agents
* CB military symbol

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Original source: https://en.wikipedia.org/wiki/Cyclohexanol. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Cyclohexanol&oldid=820064"
*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H315]: Causes skin irritation
*[H332]: Harmful if inhaled
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
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