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Cyclohexanol

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Cyclohexanol Basic information
Cyclohexanol Chemical Properties
  • Melting point:23 °C
  • Boiling point:161 °C
  • 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.)
  • Flash point:67 °C
  • storage temp. Store at RT.
  • solubility 40g/l
  • form Liquid After Melting
  • color Clear colorless
  • Relative polarity0.509
  • OdorLike camphor.
  • PH6.5 (40g/l, H2O, 20℃)
  • explosive limit2-11.2%(V)
  • Water Solubility 3.6 g/100 mL (20 ºC)
  • Sensitive Hygroscopic
  • Merck 14,2725
  • BRN 906744
  • Henry's Law Constant16.9 at 50.00 °C, 34.4 at 60.00 °C (headspace-GC, Hovorka et al., 2002)
  • Exposure limitsTLV-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.
  • CAS DataBase Reference108-93-0(CAS DataBase Reference)
  • NIST Chemistry ReferenceCyclohexanol(108-93-0)
  • EPA Substance Registry SystemCyclohexanol (108-93-0)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 20/22-37/38
  • Safety Statements 24/25
  • RIDADR 1993
  • WGK Germany 1
  • RTECS GV7875000
  • 21
  • Autoignition Temperature572 °F
  • TSCA Yes
  • HS Code 2906 12 00
  • Hazardous Substances Data108-93-0(Hazardous Substances Data)
  • ToxicityLD50 orally in rats: 2.06 g/kg (Smyth)
MSDS
Cyclohexanol Usage And Synthesis
  • Chemical Propertiescolourless liquid
  • Chemical PropertiesCyclohexanol is a sticky solid (above 25℃ /77℃ F) or colorless, viscous liquid. Faint camphor odor.
  • Physical propertiesClear, 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).
  • OccurrenceHas apparently not been reported to occur in nature
  • UsesCyclohexanol 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.
  • UsesSolvent for alkyd resins, alcohol-sol phenolic resins, ethyl cellulose. manufacture of celluloid; finishing textiles; insecticides.
  • DefinitionChEBI: An alcohol that consists of cyclohexane bearing a single hydroxy substituent. The parent of the class of cyclohexanols.
  • PreparationBy reduction of cyclohexanone or by hydrogenation of phenol in the presence of a catalyst (Arctander, 1969).
  • Production MethodsCyclohexanol 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.
  • General DescriptionA 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 ReactionsLess dense than water and slightly soluble in water.
  • Reactivity ProfileCyclohexanol 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.).
  • HazardToxic by ingestion.
  • Health HazardNarcosis-depression of the central nervous system tending to produce sleep or unconsciousness.
  • Health HazardCyclohexanol 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.
  • Chemical ReactivityReactivity 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 ExposureCyclohexanol 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.
  • Environmental FateBiological. Reported biodegradation products include cyclohexanone (Dugan, 1972; Verschueren, 1983), 2-hydroxyhexanone, 1-oxa-2-oxocycloheptane, 6-hydroxyheptanoate, 6- oxohexanoate, and adipate (quoted, Verschueren, 1983). In activated sludge inoculum, following a 20-d adaptation period, 96.0% COD removal was achieved. The average rate of biodegradation was 28.0 mg COD/g?h (Pitter, 1976).
    Photolytic. A photooxidation reaction rate constant of 1.74 x 10-13 cm3/molecule?sec was estimated for the reaction of cyclohexanol with OH radicals in the atmosphere (Atkinson, 1987).
    Chemical/Physical. Cyclohexanol will not hydrolyze in water because it does not contain a hydrolyzable functional group (Kollig, 1993).
    Complete combustion in air yields carbon dioxide and water vapor.
  • MetabolismCyclohexanol and its derivatives are generally not aromatized in vivo; large amounts of cyclohexanol may be excreted as urinary glucuronides (Williams, 1959), without prolonged retention in the organism (Browning, 1965). No urinary metabolites were detected when cyclohexanol was given to dogs by Bernhard (1937), who administered an sc dose of 0.29 g/kg, or by Weitzel (1950). Glucuronic acid was found in the urine of a dog following oral administration of cyclohexanol (Treon, 1963). Following administration to rabbits orally or by inhalation, cyclohexanol was excreted in the urine in conjugation with sulphuric and glucuronic acids. When 1-2 g cyclohexanol/kg (half the minimum lethal dose) was given orally to rabbits, 45-50% was excreted conjugated with glucuronic acid, with a decreased ratio of urinary inorganic sulphates to total sulphates. No cyclohexanone was recovered from the urine of a rabbit given 33% of the minimum lethal dose orally (Treon et al. 1943a,b). Elliott, Parke & Williams (1959) reported that more than 65% of a dose of 0-25 g cyclohexanol/kg was excreted by rabbits as glucuronides, chiefly cyclohexyl glucuronide, and an additional 6% was excreted as conjugated frarcs-cyclohexane-l,2-diol. Cyclohexanol is of interest as a metabolite of sodium cyclamate, having been identified as a metabolite in the urine of rats (Kojima & Ichibagase, 1968), rabbits (Ichibagase, Kojima, Inoue & Suenaga, 1972; Kojima & Ichibagase, 1968), guinea-pigs (Asahina, Yamaha, Sarrazin & Watanabe, 1972) and human subjects (Kojima & Ichibagase, 1969) given sodium cyclamate orally. When rabbits received 50 mg cyclohexanol as a single oral dose, the urine contained 25% of the unchanged alcohol and < 1% of the glucuronide. When rabbit-liver homogenate was incubated with cyclohexanol, 28% of the alcohol remained unchanged and 7% was metabolized. Almost no change occurred in the metabolism of cyclohexanol when the animal was pretreated with tolbutamide, which accelerates the metabolism of sodium cyclamate in the rabbit (Ichibagase et al. 1972). Cyclohexanol was not utilized to any significant extent by a number of endocrine tissues from human placenta, rat ovary, rat testis and rat adrenal gland (Ferguson, Baillie, Caiman & Hart, 1966). It was oxidized by horse-liver alcohol dehydrogenase in a preparative-scale process (Jones & Taylor, 1973) and was fermented in a process for the treatment of waste waters from caprolactam production (Kolesov, 1973). Cyclohexanol was identified as a metabolite in the urine (free and glucuronide-conjugated) in the expired air of rats receiving n-heptyl cyclohexylboronate as a single ip, iv or oral dose of 0.1 mg/kg (Caujolle, Mariotti, Oustrin & Pitet, 1970).
  • ShippingUN1986 Alcohols, toxic, flammable, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poison Inhalation Hazard, Technical Name Required.
  • Purification MethodsReflux 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.]
  • IncompatibilitiesForms 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 DisposalDissolve 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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