ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Cyclic hydrocarbons > Cyclohexane
Cyclohexane Chemical Properties
- Melting point:4-7 °C(lit.)
- Boiling point:80.7 °C(lit.)
- Density 0.779 g/mL at 25 °C(lit.)
- vapor density 2.9 (vs air)
- vapor pressure 168.8 mm Hg ( 37.7 °C)
- refractive index n
- Flash point:-1 °F
- storage temp. Store at RT.
- solubility ethanol: miscible(lit.)
- form Liquid
- color colorless
- Odorresembling benzene; mild, sweet, resembling chloroform.
- Relative polarity0.006
- Odor Threshold2.5ppm
- explosive limit1.2-8.3%(V)
- Water Solubility PRACTICALLY INSOLUBLE
- FreezingPoint 6.554℃
- λmaxλ: 210 nm Amax: ≤1.00
λ: 220 nm Amax: ≤0.50
λ: 230 nm Amax: ≤0.20
λ: 235 nm Amax: ≤0.10
λ: 240 nm Amax: ≤0.08
λ: 250 nm Amax: ≤0.03
λ: 255 nm Amax: ≤0.01
- Merck 14,2723
- BRN 1900225
- Henry's Law Constant1.03, 1.26, 1.40, 1.77, and 2.23 at 10, 15, 20, 25, and 30 °C, respectively (EPICS, Ashworth et al., 1988) 0.54, 0.69, 0.82, 1.43, and 1.79 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (Dewulf et al.,1999)
- Exposure limitsTLV-TWA 300 ppm (～1050 mg/m3) (ACGIH, OSHA, and NIOSH); IDLH 10,000 ppm (NIOSH).
- CAS DataBase Reference110-82-7(CAS DataBase Reference)
- NIST Chemistry ReferenceCyclohexane(110-82-7)
- EPA Substance Registry SystemCyclohexane (110-82-7)
- Hazard Codes F,Xn,N
- Risk Statements 11-38-50/53-65-67-20
- Safety Statements 9-16-25-33-60-61-62
- RIDADR UN 1145 3/PG 2
- WGK Germany 2
- RTECS GU6300000
- F 3-10
- Autoignition Temperature500 °F
- TSCA Yes
- HS Code 2902 11 00
- HazardClass 3
- PackingGroup II
- Hazardous Substances Data110-82-7(Hazardous Substances Data)
- ToxicityLC in mice: ~60-70 mg/l air (Lazarew)
Cyclohexane Usage And Synthesis
- Chemical PropertiesCyclohexane is a colorless liquid with a mild, sweet odor.
- Physical propertiesColorless liquid with a sweet, chloroform-like odor. A detection odor threshold concentration of 2,700 mg/m3 (784 ppmv) was experimentally determined by Dravnieks (1974). An odor threshold concentration of 2.7 ppbv was reported by Nagata and Takeuchi (1990).
- UsesSuitable for HPLC, spectrophotometry, environmental testing
- UsesSolvent for lacquers and resins. Paint and varnish remover. In the extraction of essential oils. In analytical chemistry for mol wt determinations (cryoscopic constant 20.3). In the manufacture of adipic acid, benzene, cyclohexyl chloride, nitrocyclohexane, cyclohexanol and cyclohexanone. In the manufacture of solid fuel for camp stoves. In fungicidal formulations (possesses slight fungicidal action). In the industrial recrystallization of steroids.
- UsesCyclohexane is a petroleum product obtainedby distilling C4- 400°F boiling rangenaphthas, followed by fractionation andsuperfractionation; also formed by catalytichydrogenation of benzene. It is usedextensively as a solvent for lacquers andresins, as a paint and varnish remover, andin the manufacture of adipic acid, benzene,cyclohexanol, and cyclohexanone.
- DefinitionA colorless liquid alkane that is commonly used as a solvent and in the production of hexanedioic acid (adipic acid) for the manufacture of nylon. Cyclohexane, itself, is manufactured by the reformation of longer chain hydrocarbons present in crude-oil fractions. It is also interesting from a structural point of view, existing as a ‘puckered’ six-membered ring, having all bonds between carbon atoms at 109.9° (the tetrahedral angle). The molecule undergoes rapid interconversion between two ‘chair-like’ CONFORMATIONS, which are energetically equivalent, passing through a ‘boat-like’ structure of higher energy. It is commonly represented by a hexagon.
- Definitioncyclohexane: A colourless liquidcycloalkane, C6H12; r.d. 0.78; m.p.6.5°C; b.p. 81°C. It occurs in petroleumand is made by passing benzeneand hydrogen under pressureover a heated Raney nickel catalyst at150°C, or by the reduction of cyclohexanone.It is used as a solvent andpaint remover and can be oxidizedusing hot concentrated nitric acid tohexanedioic acid (adipic acid). The cyclohexanering is not planar and canadopt boat and chair conformations;in formulae it is representedby a single hexagon.
- DefinitionChEBI: An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.
- Production MethodsCyclohexane is fractionated from crude oil and may be released wherever petroleum products are refined, stored, and used. Another large source of general release is in exhaust gases from motor vehicles. It is prepared synthetically from benzene, by hydrocracking of cyclopentane, or from toluene by simultaneous dealkylation and double bond hydrogenation.
- General DescriptionA clear colorless liquid with a petroleum-like odor. Used to make nylon, as a solvent, paint remover, and to make other chemicals. Flash point -4°F. Density 6.5 lb / gal (less than water) and insoluble in water. Vapors heavier than air.
- Air & Water ReactionsHighly flammable. Insoluble in water.
- Reactivity ProfileLiquid nitrogen dioxide was fed into a nitration column containing hot Cyclohexane, due to an error. An explosion resulted [MCA Case History 128(1962)] Incompatible with strong oxidizers.
- Health HazardDizziness, with nausea and vomiting. Concentrated vapor may cause unconsciousness and collapse.
- Health HazardCyclohexane is an acute toxicant of loworder. It is an irritant to the eyes and respiratorysystem. Exposure to a 1–2% concentrationin air caused lethargy, drowsiness,and narcosis in test animals. The lethal concentrationfor a 1-hour exposure in mice isestimated at around 30,000 ppm. Ingestionof cyclohexane exhibited low toxic effects intest species. The LD50 values in the literature show a wide variation. It may be detectedfrom its odor at 300 ppm concentration.
- 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.
- Safety ProfilePoison by intravenous route, Moderately toxic by ingestion. A systemic irritant by inhalation and ingestion. A skin irritant. Mutation data reported. Flammable liquid. Dangerous fire hazard when exposed to heat or flame; can react with oxidming materials. Moderate explosion hazard in the form of vapor when exposed to flame. When mixed hot with liquid dinitrogen tetraoxide an explosion can result. To fight fire, use foam, CO2, dry chemical, spray, fog. When heated to decomposition it emits acrid smoke and fumes.
- Potential ExposureCyclohexane is used as a chemical intermediate; as a solvent for fats, oils, waxes, resins, cer- tain synthetic rubbers; and as an extractant of essential oils in the perfume industry.
- CarcinogenicityNo tumor-promoting activity was observed in mice receiving one 60 mL application of 0.3% DMBA in benzene followed by a 60 mL application of cyclohexane twice weekly for 50 weeks.
- SourceSchauer et al. (1999) reported cyclohexane in a diesel-powered medium-duty truck
exhaust at an emission rate of 210 μg/km.
California Phase II reformulated gasoline contained cyclohexane at a concentration of 8,900 mg/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 1.44 and 238.0 mg/km, respectively (Schauer et al., 2002).
- Environmental FateBiological. Microbial degradation products reported include cyclohexanol (Dugan, 1972;
Verschueren, 1983), 1-oxa-2-oxocycloheptane, 6-hydroxyheptanoate, 6-oxohexanoate, adipic acid,
acetyl-CoA, succinyl-CoA (quoted, Verschueren, 1983), and cyclohexanone (Dugan, 1972; Keck
et al., 1989).
Photolytic. The following rate constants were reported for the reaction of cyclohexane and OH radicals in the atmosphere: 5.38 x 10-12 cm3/molecule?sec at 295 K (Greiner, 1970); 6.7 x 10-12 cm3/molecule?sec at 300 K (Darnall et al., 1978); 6.69 x 10-12 cm3/molecule?sec at 298 (DeMore and Bayes, 1999); 7.0 x 10-12 cm3/molecule?sec (Atkinson et al., 1979); 7.49 x 10-12 cm3/molecule?sec (Atkinson, 1990). A photooxidation reaction rate constant of 1.35 x 10-16 cm3/molecule?sec was reported for the reaction of cyclohexane with NO3 in the atmosphere (Atkinson, 1991).
Chemical/Physical. The gas-phase reaction of cyclohexane with OH radicals in the presence of nitric oxide yielded cyclohexanone and cyclohexyl nitrate as the major products (Aschmann et al., 1997).
Cyclohexane will not hydrolyze because it has no hydrolyzable functional group.
- ShippingUN1145 Cyclohexane, Hazard Class: 3; Labels: 3-Flammable liquid.
- Purification MethodsIt is best to purify it by washing with conc H2SO4 until the washings are colourless, followed by water, aqueous Na2CO3 or 5% NaOH, and again water until neutral. It is then dried with P2O5, Linde type 4A molecular sieves, CaCl2, or MgSO4 then Na and distilled. Cyclohexane has been refluxed with, and distilled from Na, CaH2, LiAlH4 (which also removes peroxides), sodium/potassium alloy, or P2O5. Traces of *benzene can be removed by passage through a column of silica gel that has been freshly heated: this gives material suitable for ultraviolet and infrared spectroscopy. If there is much *benzene in the cyclohexane, most of it can be removed by a preliminary treatment with nitrating acid (a cold mixture of 30mL conc HNO3 and 70mL of conc H2SO4) which converts *benzene into nitrobenzene. The impure cyclohexane and the nitrating acid are placed in an ice bath and stirred vigorously for 15minutes, after which the mixture is allowed to warm to 25o during 1hour. The cyclohexane is decanted, washed several times with 25% NaOH, then water, dried with CaCl2, and distilled from sodium. Carbonyl-containing impurities can be removed as described for chloroform. Other purification procedures include passage through columns of activated alumina and repeated crystallisation by partial freezing. Small quantities may be purified by chromatography on a Dowex 710-Chromosorb W gas-liquid chromatographic column. Flammable liquid. [Sabatier Ind Eng Chem 18 1005 1926, Schefland & Jacobs The Handbook of Organic Solvents (Van Nostrand) p592 1953, Beilstein 5 IV 27.] Rapid purification: Distil, discarding the forerun. Stand distillate over Grade I alumina (5% w/v) or 4A molecular sieves.
- IncompatibilitiesMay form explosive mixture with air. Contact with oxidizers, nitrogen dioxide, and oxygen can cause fire and explosion hazard. Can explode in heat when mixed with dinitrogen tetraoxide liquid.
- 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.
Cyclohexane Preparation Products And Raw materials
- Raw materialsBenzeneHydrogenPhenanthreneCYCLOHEXANE-D12
- Preparation ProductsN-METHYLOCTYLAMINEBis(pinacolato)diboron Hexamethylphosphorous triamideTramadol hydrochlorideRamiprilBromopyruvic acidMilrinoneGestrinoneSimvastatin1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER(6-ETHYL-4-OXO-4H-THIENO[2,3-D]PYRIMIDIN-3-YL)-ACETIC ACID5-BROMO-2-FLUOROPYRIDINE-3-CARBALDEHYDE2-(CHLOROMETHYL)-6-ETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE3-(3,5-DICHLOROPHENOXY)BENZALDEHYDE3-(3,4-DICHLOROPHENOXY)BENZALDEHYDE4-CHLORO-6-ETHYLTHIENO[2,3-D]PYRIMIDINE1-(2-Pyridylazo)-2-naphtholVitamin D24-CHLORO-8-(TRIFLUOROMETHYL)QUINOLINE2-METHOXY-6-METHYL-4(1H)-PYRIMIDINONETetraheptylammonium bromide6-ethylthieno[2,3-d]pyrimidin-4(3H)-oneN-Vinyl-2-pyrrolidoneProgabide2,3-DIHYDROXYPROPYL METHACRYLATEETHYL 2-AMINO-5-ETHYLTHIOPHENE-3-CARBOXYLATE2,5-DICHLORO-4-FORMYLPYRIDINEBefunolol3-METHYL-2-NITROBENZYL ALCOHOLAtovaquoneBenalaxyldimethyl octadecyloxy methylene betaineCyhalothrinVitamin D3Ziegler catalyst、Phillips catalystACID BLUE 62controlled release property of urea coated by sulfonated EPDM ionomerGabapentin hydrochloride3-methyl-2-nitrobenzoyl chloridepolyoxyethylene fatty acid glycerol borate
- Hexane Cyclohexanone Cyclohexylbenzene 2-ETHYLCYCLOHEXANOL 4'-CYCLOHEXYLACETOPHENONE 1,4-Cyclohexanediol PERHYDROFLUORENE 4-Methylcyclohexanol DL-ISOPINOCAMPHEOL beta-Pinene 2-Methylcyclohexanol Cyclohexane Methylcyclohexane Chlorocyclohexane Cyclohexyl mercaptan 4-CYCLOHEXYLANILINE 3-Methylcyclohexanol METHYL O-METHYLPODOCARPATE
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