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| | Cyclohexanol Basic information |
| | Cyclohexanol Chemical Properties |
| Melting point | 20-22 °C (lit.) | | Boiling point | 160-161 °C (lit.) | | density | 0.948 g/mL at 25 °C (lit.) | | vapor density | 3.5 (vs air) | | vapor pressure | 0.98 mm Hg ( 25 °C) | | refractive index | n20/D 1.465(lit.) | | Fp | 67 °C | | storage temp. | Store below +30°C. | | solubility | 40g/l | | form | Liquid After Melting | | pka | 16 | | color | Clear colorless | | Odor | Like camphor. | | Relative polarity | 0.509 | | PH | 6.5 (40g/l, H2O, 20℃) | | explosive limit | 2-11.2%(V) | | Odor Type | camphoreous | | Water Solubility | 3.6 g/100 mL (20 ºC) | | Sensitive | Hygroscopic | | Merck | 14,2725 | | BRN | 906744 | | Henry's Law Constant | 16.9 at 50.00 °C, 34.4 at 60.00 °C (headspace-GC, Hovorka et al., 2002) | | Exposure limits | TLV-TWA 200 mg/m3 (50 ppm) (ACGIH);
IDLH 3500 ppm (NIOSH). | | Stability: | Stable. Incompatible with oxidizing agents. Reacts violently with oxidizing agents such as hydrogen peroxide and nitric acid, even at room temperature, to form an explosive material. Hygroscopic. Combustible. | | LogP | 1.25 at 25℃ | | CAS DataBase Reference | 108-93-0(CAS DataBase Reference) | | NIST Chemistry Reference | Cyclohexanol(108-93-0) | | EPA Substance Registry System | Cyclohexanol (108-93-0) |
| | Cyclohexanol Usage And Synthesis |
| Chemical Properties | Cyclohexanol is a sticky solid (above 25°C /77°C F) or colorless, viscous liquid. Faint camphor odor.It has a fairly high flash point and boiling range. A solvent for cellulose ethers, ester gum,shellac, low viscosity silicones and polyvinyl chloride. lt has a fairly limited use in screen inks. lt is miscible with oils and hydrocarbon solvents. | | Physical properties | Clear, colorless to pale yellow, viscous, hygroscopic liquid with a camphor-like odor. A detection
odor threshold concentration of 64 μg/m3 (155 ppbv) was reported by Punter (1983). | | Uses | Cyclohexanol is used for the productionof adipic acid and caprolactam for makingnylon. Its phthalate derivatives are used forplasticizers. It is used as a stabilizer for soapsand detergents; as a solvent for lacquers,varnishes, and shellacs; and as a dye solventfor textiles. | | Uses | Solvent for oils, resins, ethyl cellulose;
manufacture of soap, plastics | | Production Methods | Cyclohexanol is prepared by the catalytic air oxidation of
cyclohexane or by the catalytic hydrogenation of phenol. The most important use of cyclohexanol is in producing
adipic acid used in the manufacture of caprolactam.
Cyclohexanol is used in the manufacture of esters for use
as plasticizers; it is also used as a chemical intermediate, a
stabilizer, a homogenizer for various soap and detergent
emulsions, and as a solvent for lacquers and varnishes .
The primary routes of occupational exposure are dermal and
inhalation. | | Definition | ChEBI: Cyclohexanol is an alcohol that consists of cyclohexane bearing a single hydroxy substituent. The parent of the class of cyclohexanols. It has a role as a solvent. It is a secondary alcohol and a member of cyclohexanols. | | Synthesis Reference(s) | Journal of the American Chemical Society, 97, p. 7118, 1975 DOI: 10.1021/ja00857a025
Tetrahedron Letters, 21, p. 2305, 1980 DOI: 10.1016/S0040-4039(00)92591-7 | | General Description | A colorless liquid with a camphor-like odor. Soluble in most organic liquids. Flash point 154°F. May be toxic by inhalation or skin exposure. Vapors are narcotic in high concentrations. Irritates skin, eyes and mucus membranes. Used in making soap, lacquers, and plastics. | | Air & Water Reactions | Less dense than water and slightly soluble in water. | | Reactivity Profile | Cyclohexanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Violent reaction with nitric acid. Incompatible with strong oxidizers (chromium trioxide, nitric acid, etc.). | | Health Hazard | Cyclohexanol is moderately toxic. Targetorgans are the eyes, skin, and respiratorysystem. At high concentrations cyclohexanolabsorbed through the skin may possiblyinjure the brain, kidney, and heart.
LD50 value, single oral dose (rats): 2060mg/kg
LD50 value, single intravenous dose (mice):270 mg/kg
Inhalation of vapors may cause irritationof the eyes, nose, and throat. However,because of its low vapor pressure (1.12 torrat 25°C), the health hazard due to inhalationis low. Ingestion can cause nausea,trembling, and gastrointestinal disturbances.Repeated skin contact may produce erythemaand edema. | | Flammability and Explosibility | Notclassified | | Chemical Reactivity | Reactivity with Water: No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | | Potential Exposure | Cyclohexanol is used in making plac-
ticizers, dry cleaning, dyebath; and textile finishing formu-
lations; as a solvent for ethyl cellulose and other resins; it
is used in soap manufacture; it is used as a raw material for
adipic acid manufacture; as a nylon intermediate. | | Shipping | UN1986 Alcohols, toxic, flammable, n.o.s.,
Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poison
Inhalation Hazard, Technical Name Required. | | Purification Methods | Reflux it with freshly ignited CaO, or dry it with Na2CO3, then fractionally distil it. Redistil it from Na. It is further purified by fractional crystallisation from the melt in dry air. Peroxides and aldehydes can be removed by prior washing with ferrous sulfate and water, followed by distillation under nitrogen from 2,4-dinitrophenylhydrazine, using a short fractionating column: water distils as the azeotrope. Dry cyclohexanol is very hygroscopic. The 3,4-dinitrobenzoate has m 111-112o (EtOH or aqueous EtOH) It has TOXIC vapours. [Beilstein 6 III 10, 6 IV 20.] | | Incompatibilities | Forms explosive mixture in air.
Incompatible with oxidizers (chlorates, nitrates, peroxides,
permanganates, perchlorates, chlorine, bromine, fluorine,
etc.); contact may cause fires or explosions. Keep away
from alkaline materials, strong bases, strong acids, oxoa-
cids, epoxides. Attacks some plastics. | | Waste Disposal | Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera-
tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. |
| | Cyclohexanol Preparation Products And Raw materials |
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