“Cyclohexanol”的意思、由来-开放百科全书

词条

Cyclohexanol

释义

Production
Basic reactions
Structure
Applications
Safety
References

{{chembox
| Watchedfields = changed
| verifiedrevid = 443680043
| Reference=^[1]
| 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
| IUPACName = Cyclohexanol
| OtherNames = Cyclohexyl Alcohol,
hexahydrophenol,
hydrophenol,
hydroxycyclohexane,
Naxol
Hexalin
Hydralin
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}}
| RTECS = GV7875000
| EC_number = 203-630-6
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7678
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00854
| 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 = C₆H₁₂O
| MolarMass = 100.158 g/mol
| Appearance = Colorless, viscous liquid.
Hygroscopic
| Odor = camphor-like
| Density = 0.9624 g/mL, liquid
| Solubility = 3.60 g/100 mL (20 °C)
4.3 g/100 mL (30 °C)
| SolubleOther = soluble in ethanol, ethyl ether acetone, chloroform
miscible with ethyl acetate, linseed oil, benzene
| MeltingPtC = 25.93
| BoilingPtC = 161.84
| pKa = 16
| pKb =
| Viscosity = 41.07 mPa·s (30 °C)
| RefractIndex = 1.4641
| HenryConstant = 4.40 x 10⁻⁶ atm-cu m/mol
| VaporPressure = 1 mmHg (20°C)^[2]
| MagSus = -73.40·10⁻⁶ cm³/mol
|Section7={{Chembox Hazards
| ExternalSDS = MSDS for cyclohexanol
| MainHazards = Flammable, skin irritant
Reacts violently with oxidizing agents
| NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 0
| FlashPtC = 67
| AutoignitionPtC = 300
| ExploLimits = 2.7-12%
| LD50 = 2060 mg/kg (oral, rat)
2200-2600 mg/kg (oral, rabbit)^[2]
| RPhrases = {{R20}} {{R22}} {{R37}} {{R38}}
| SPhrases = {{S24}} {{S25}}
| PEL = TWA 50 ppm (200 mg/m³)^[3]
| IDLH = 400 ppm^[3]
| REL = TWA 50 ppm (200 mg/m³)^[3]
}}Cyclohexanol is the organic compound with the formula HOCH(CH₂)₅. 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]

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

1. ^Merck Index, 11th Edition, 2731.
2. ^{{IDLH|108930|Cyclohexanol}}
3. ^¹²³{{PGCH|0165}}
4. ^{{RubberBible86th}}
5. ^¹²³Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
6. ^[https://www.cdc.gov/niosh/npg/npgd0165.html CDC - NIOSH Pocket Guide to Chemical Hazards]
7. ^[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.

3 : Cyclohexanols|Cycloalkanols|Cyclohexanes

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