| | Cyclohexane Basic information |
| | 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 | n20/D 1.426(lit.) | | Fp | -1 °F | | storage temp. | Store at +5°C to +30°C. | | solubility | ethanol: miscible(lit.) | | form | Liquid | | color | colorless | | Odor | resembling benzene; mild, sweet, resembling chloroform. | | Relative polarity | 0.006 | | Odor Threshold | 2.5ppm | | explosive limit | 1.2-8.3%(V) | | Water Solubility | PRACTICALLY INSOLUBLE | | FreezingPoint | 6.554℃ | | λmax | λ: 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 Constant | 1.03, 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 limits | TLV-TWA 300 ppm (～1050 mg/m3)
(ACGIH, OSHA, and NIOSH); IDLH
10,000 ppm (NIOSH). | | Stability: | Volatile | | InChIKey | XDTMQSROBMDMFD-UHFFFAOYSA-N | | LogP | 3.44 at 20℃ | | CAS DataBase Reference | 110-82-7(CAS DataBase Reference) | | NIST Chemistry Reference | Cyclohexane(110-82-7) | | EPA Substance Registry System | Cyclohexane (110-82-7) |
| | Cyclohexane Usage And Synthesis |
| Description | Cyclohexane is obtained by the distillation of petroleum or
by hydrogenation of benzene. It constitutes 0.5–1.0% of
petroleum | | Chemical Properties | Cyclohexane is a colorless liquid with a mild,
sweet odor. | | Physical properties | Colorless 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). | | Uses | Suitable for HPLC, spectrophotometry, environmental testing | | Uses | Solvent 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. | | Uses | Cyclohexane 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. | | Definition | A 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. | | Definition | cyclohexane: 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. | | Definition | ChEBI: 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 Methods | Cyclohexane 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 Description | A 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 Reactions | Highly flammable. Insoluble in water. | | Reactivity Profile | Liquid 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 Hazard | Dizziness, with nausea and vomiting. Concentrated vapor may cause unconsciousness and collapse. | | Health Hazard | Cyclohexane 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. | | Flammability and Explosibility | Highlyflammable | | 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. | | Safety Profile | Poison 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 Exposure | Cyclohexane 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. | | Carcinogenicity | No 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. | | Source | Schauer 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 fate | Biological. 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. | | Shipping | UN1145 Cyclohexane, Hazard Class: 3; Labels:
3-Flammable liquid. | | Purification Methods | It 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. | | Toxicity evaluation | If released to air, cyclohexane will exist solely as a vapor in the
ambient atmosphere, and will be degraded in the atmosphere
by reaction with photochemically produced hydroxyl radicals,
though direct photolysis is not expected due to the lack of
absorption in the environmental spectrum. Volatilization from
water surfaces is expected to be an important fate for this
compound, and half-lives in a model river and lake are expected
to be 3 h and ～3.5 days respectively. Adsorption to
suspended solids and sediments is also expected, though
hydrolysis in the environment is unlikely due to the lack of
hydrolyzable functional groups.
The potential for bioconcentration and bioaccumulation of
cyclohexane in aquatic organisms is moderate. It is highly
resistant to biodegradation and is catabolized chiefly by
cooxidation. | | Incompatibilities | May 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 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. |
| | Cyclohexane Preparation Products And Raw materials |
| Raw materials | Benzene-->Hydrogen-->Phenanthrene-->CYCLOHEXANE-D12 | | Preparation Products | N-METHYLOCTYLAMINE-->Bis(pinacolato)diboron-->Hexamethylphosphorous triamide-->Tramadol hydrochloride-->Ramipril-->3-Bromopyruvic acid-->Milrinone-->Gestrinone-->Simvastatin-->1-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 ACID-->5-BROMO-2-FLUOROPYRIDINE-3-CARBALDEHYDE-->2-(CHLOROMETHYL)-6-ETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE-->3-(3,5-DICHLOROPHENOXY)BENZALDEHYDE-->3-(3,4-DICHLOROPHENOXY)BENZALDEHYDE-->4-CHLORO-6-ETHYLTHIENO[2,3-D]PYRIMIDINE-->1-(2-Pyridylazo)-2-naphthol-->Vitamin D2-->4-CHLORO-8-(TRIFLUOROMETHYL)QUINOLINE-->2-METHOXY-6-METHYL-4(1H)-PYRIMIDINONE-->Tetraheptylammonium bromide-->6-ethylthieno[2,3-d]pyrimidin-4(3H)-one-->N-Vinyl-2-pyrrolidone-->Progabide-->2,3-DIHYDROXYPROPYL METHACRYLATE-->ETHYL 2-AMINO-5-ETHYLTHIOPHENE-3-CARBOXYLATE-->2,5-DICHLORO-4-FORMYLPYRIDINE-->Befunolol-->3-METHYL-2-NITROBENZYL ALCOHOL-->Atovaquone-->Benalaxyl-->dimethyl octadecyloxy methylene betaine-->Cyhalothrin-->Vitamin D3-->Ziegler catalyst、Phillips catalyst-->ACID BLUE 62-->controlled release property of urea coated by sulfonated EPDM ionomer-->Gabapentin-->3-methyl-2-nitrobenzoyl chloride-->polyoxyethylene fatty acid glycerol borate |
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