シクロヘキサノール
WordNet
- a colorless oily alcohol that smells like camphor
- the cyclohexanol ester of phthalic acid
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/15 05:52:45」(JST)
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Cyclohexanol[1]
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|
| Names |
| IUPAC name
Cyclohexanol
|
Other names
Cyclohexyl Alcohol,
hexahydrophenol,
hydrophenol,
hydroxycyclohexane,
Naxol
Anol
Hexalin
Hydralin |
| Identifiers |
|
CAS Number
|
108-93-0 Y |
| ChEBI |
CHEBI:18099 Y |
| ChEMBL |
ChEMBL32010 Y |
| ChemSpider |
7678 Y |
| DrugBank |
DB03703 Y |
| EC Number |
203-630-6 |
| Jmol interactive 3D |
Image |
| KEGG |
C00854 Y |
| PubChem |
7966 |
| RTECS number |
GV7875000 |
InChI
-
InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 Y
Key: HPXRVTGHNJAIIH-UHFFFAOYSA-N Y
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InChI=1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
Key: HPXRVTGHNJAIIH-UHFFFAOYAN
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|
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| 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 |
|
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 |
| R-phrases |
R20 R22 R37 R38 |
| S-phrases |
S24 S25 |
| NFPA 704 |
|
| 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] |
| US health exposure limits (NIOSH): |
|
PEL (Permissible)
|
TWA 50 ppm (200 mg/m3)[2] |
|
REL (Recommended)
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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 |
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|
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.[4] This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Billions of kilograms 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]
- 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]
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 somewhat toxic: the TLV 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.[6] Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.[7]
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 and Health. 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.
- ^ 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.
|
Alcohols
|
|
Straight-chain
primary
alcohols (1°) |
- Methanol (C
1)
- Ethanol (C
2)
- 1-Propanol (C
3)
- n-Butanol (C
4)
- 1-Pentanol (C
5)
- 1-Hexanol (C
6)
- 1-Heptanol (C
7)
- 1-Octanol (C
8)
- 1-Nonanol (C
9)
- 1-Decanol (C
10)
- Undecanol (C
11)
- Dodecanol (C
12)
- Tridecan-1-ol (C
13)
- 1-Tetradecanol (C
14)
- Pentadecan-1-ol (C
15)
- Cetyl alcohol (C
16)
- Heptadecan-1-ol (C
17)
- Stearyl alcohol (C
18)
- Nonadecan-1-ol (C
19)
- Arachidyl alcohol (C
20)
- Heneicosan-1-ol (C
21)
- Docosanol (C
22)
- Tricosan-1-ol (C
23)
- 1-Tetracosanol (C
24)
- Pentacosan-1-ol (C
25)
- 1-Hexacosanol (C
26)
- 1-Heptacosanol (C
27)
- 1-Octacosanol (C
28)
- 1-Nonacosanol (C
29)
- Triacontanol (C
30)
|
|
Other primary
alcohols |
- Isobutanol (C
4)
- Isoamyl alcohol (C
5)
- 2-Methyl-1-butanol (C
5)
- Phenethyl alcohol (C
8)
- Tryptophol (C
10)
|
|
Secondary
alcohols (2°) |
- Isopropanol (C
3)
- 2-Butanol (C
4)
- 2-Pentanol (C
5)
- 2-Hexanol (C
6)
- 2-Heptanol (C
7)
- Cyclohexanol (C
6)
|
|
Tertiary
alcohols (3°) |
- tert-Butyl alcohol (C
4)
- tert-Amyl alcohol (C
5)
- 2-Methyl-2-pentanol (C
6)
- 2-Methylhexan-2-ol (C
7)
- 2-Methylheptan-2-ol (C
8)
- 3-Methyl-3-pentanol (C
6)
- 3-Methyloctan-3-ol (C
9)
|
|
English Journal
- CB1 Knockout Mice Unveil Sustained CB2-Mediated Antiallodynic Effects of the Mixed CB1/CB2 Agonist CP55,940 in a Mouse Model of Paclitaxel-Induced Neuropathic Pain.
- Deng L1, Cornett BL1, Mackie K1, Hohmann AG2.
- Molecular pharmacology.Mol Pharmacol.2015 Jul;88(1):64-74. doi: 10.1124/mol.115.098483. Epub 2015 Apr 22.
- Cannabinoids suppress neuropathic pain through activation of cannabinoid CB1 and/or CB2 receptors; however, unwanted CB1-mediated cannabimimetic effects limit clinical use. We asked whether CP55,940 [(-)-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-hydroxypropyl)cyclohexanol], a potent cannabinoi
- PMID 25904556
- Contribution of liver alcohol dehydrogenase to metabolism of alcohols in rats.
- Plapp BV1, Leidal KG2, Murch BP3, Green DW4.
- Chemico-biological interactions.Chem Biol Interact.2015 Jun 5;234:85-95. doi: 10.1016/j.cbi.2014.12.040. Epub 2015 Jan 29.
- The kinetics of oxidation of various alcohols by purified rat liver alcohol dehydrogenase (ADH) were compared with the kinetics of elimination of the alcohols in rats in order to investigate the roles of ADH and other factors that contribute to the rates of metabolism of alcohols. Primary alcohols (
- PMID 25641189
- A structural study of (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1,3,5-triphenylcyclohexan-1-ol chloroform hemisolvate and (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1-phenyl-3,5-bis(2-methoxyphenyl)cyclohexan-1-ol.
- Minyaev ME1, Roitershtein DM1, Nifant'ev IE1, Ananyev IV2, Minyaeva TV3, Mikhaylyev TA4.
- Acta crystallographica. Section C, Structural chemistry.Acta Crystallogr C Struct Chem.2015 Jun 1;71(Pt 6):491-8. doi: 10.1107/S2053229615009857. Epub 2015 May 27.
- (1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol or (4-hydroxy-2,4,6-triphenylcyclohexane-1,3-diyl)bis(phenylmethanone), C38H32O3, (1), is formed as a by-product in the NaOH-catalyzed synthesis of 1,3,5-triphenylpentane-1,5-dione from acetophenone and benzaldehyde. Single crystals
- PMID 26044332
Japanese Journal
- Evaluation of urinary cyclohexanediols and cyclohexanol as biomarkers of occupational exposure to cyclohexane
- , , , , , , ,
- Journal of Occupational Health advpub(0), 2015
- … Objectives: The aim of the present study was to comparatively evaluate the usefulness of urinary cyclohexanediols (CHdiols-U) and cyclohexanol (CHol-U) as biomarkers of occupational exposure to cyclohexane (CH). …
- NAID 130005069599
- Electrocatalytic Hydrogenation of Lignin-Derived Phenol into Alkanes by Using Platinum Supported on Graphite
- , ,
- Electrochemistry 82(11), 954-959, 2014
- … In this work, electrocatalytic hydrogenation (ECH) of phenol to cyclohexane and cyclohexanol was studied. …
- NAID 130004707694
- Multiphase reaction media including dense phase carbon dioxide and/or water: A case study for hydrogenation of phenol with a Pd/Al2O3 catalyst
- Yoshida Hiroshi,Narisawa Satomi,Fujita Shin-ichiro,Arai Masahiko
- Journal of molecular catalysis a-chemical 379, 80-85, 2013-11-15
- … At the latter stage of reaction in this system, phenol was not consumed but cyclohexanone did transform to cyclohexanol. …
- NAID 120005385308
Related Links
- CYCLOHEXANOL | C6H11OH or C6H12O | CID 7966 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. ...
- [Cyclohexanone] [108-94-1] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日，つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては，お手数ですが営業部までお問い合わせください。
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