Cyclohexanol

Last updated
Cyclohexanol [1]
Cyclohexanol.svg
Cyclohexanol molecule ball from xtal.png
Cyclohexanol-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
Cyclohexanol
Other names
Cyclohexyl Alcohol,
hexahydrophenol,
hydrophenol,
hydroxycyclohexane,
Naxol
Hexalin
Hydralin
HOCy
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.301 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-630-6
KEGG
PubChem CID
RTECS number
  • GV7875000
UNII
  • InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 Yes check.svgY
    Key: HPXRVTGHNJAIIH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
    Key: HPXRVTGHNJAIIH-UHFFFAOYAN
  • C1CCCCC1O
Properties
C6H12O
Molar mass 100.158 g/mol
AppearanceColorless, 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)
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]
4.40 x 10−6 atm-cu m/mol
Acidity (pKa)16
-73.40·10−6 cm3/mol
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:
GHS-pictogram-exclam.svg
Warning
H302, H315, H332, H335
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)
1
2
0
Flash point 67 °C (153 °F; 340 K)
300 °C (572 °F; 573 K)
Explosive limits 2.7-12%
Lethal dose or concentration (LD, LC):
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. Billions of kilograms are produced annually, mainly as a precursor to nylon. [5]

Contents

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]

Related Research Articles

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893.

Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products. Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.

Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.

<span class="mw-page-title-main">Methyl formate</span> Chemical compound

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<span class="mw-page-title-main">Cyclohexanone</span> Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Vanadium(V) oxide</span> Precursor to vanadium alloys and industrial catalyst

Vanadium(V) oxide (vanadia) is the inorganic compound with the formula V2O5. Commonly known as vanadium pentoxide, it is a brown/yellow solid, although when freshly precipitated from aqueous solution, its colour is deep orange. Because of its high oxidation state, it is both an amphoteric oxide and an oxidizing agent. From the industrial perspective, it is the most important compound of vanadium, being the principal precursor to alloys of vanadium and is a widely used industrial catalyst.

Aziridine is an organic compound consisting of the three-membered heterocycle (CH2)2NH. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

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2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">Propan-1-ol</span> Primary alcohol compound

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<i>n</i>-Butylamine Chemical compound

n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Vapors heavier than air and it produces toxic oxides of nitrogen during combustion.

References

  1. ↑ Merck Index , 11th Edition, 2731.
  2. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0165". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ "Cyclohexanol". Immediately Dangerous to 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. 1 2 3 4 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. ↑ 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.
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