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Cyclohexane

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Cyclohexane

EINECS 203-806-2
CAS No. 110-82-7 Density 0.791 g/cm3
Solubility PRACTICALLY INSOLUBLE Melting Point 4-7 °C(lit.)
Formula C6H12 Boiling Point 80.719 °C at 760 mmHg
Molecular Weight 84.18 Flash Point -18ºC
Transport Information Appearance colorless liquid
Safety 9-16-25-33-60-61-62 Risk Codes 11-38-50/53-65-67
Molecular Structure Molecular Structure of 110-82-7 (Cyclohexane) Hazard Symbols FlammableF,HarmfulXn,DangerousN
Synonyms

Cyclohexan [German];RCRA waste no. U056;Cyclohexaan [Dutch];Cicloesano [Italian];Cyclohexane [UN1145] [Flammable liquid];hexahydro-;hexahydrobenzene;RCRA waste number U056;Cyclohexaan;Benzene, hexahydro-;Cyclohexan;Cykloheksan;hexanaphthene;hexamethylene;Cyclohexane (DOT;Cyclohexane ring;EPA Pesticide Chemical Code 025901;Cicloesano;10-81-1;Benzenehexahydride;Cykloheksan [Polish];Cyclobexane;Cyclohexane, Reagent;Cyclohexane, Spectrophotometric Grade;

 

Cyclohexane History

Unlike compounds like benzene, Cyclohexane (CAS NO.110-82-7) cannot easily be obtained from natural resources such as coal. Towards the end of the nineteenth century early chemical investigators had to depend on organic synthesis. It took them 30 years to flesh out the details.
In 1867 Marcellin Berthelot reduced benzene with hydroiodic acid at elevated temperatures. He incorrectly identified the reaction product as n-hexane not only because of the convenient match in boiling point (69°C) but also because he did not believe benzene was a cyclic molecule but rather some sort of association of acetylene.
In 1870 one of his sceptics Adolf von Baeyer repeated the reaction and pronounced the same reaction product hexahydrobenzene and in 1890 Vladimir Markovnikov believed he was able to distill the same compound from Caucasus petroleum calling his concoction hexanaphtene.
In 1894 Baeyer synthesized Cyclohexane (CAS NO.110-82-7) starting with a Dieckmann condensation of pimelic acid, and in the same year E. Haworth and W.H. Perkin Jr. (1860 - 1929) did the same in a Wurtz reaction of 1,6-dibromohexane.
Surprisingly their cyclohexanes(110-82-7) boiled higher by 10°C than either hexahydrobenzene or hexanaphtene but this riddle was solved in 1895 by Markovnikov, N.M. Kishner and Nikolay Zelinsky when they re-diagnosed hexahydrobenzene and hexanaphtene as methylcyclopentane, the result of an unexpected rearrangement reaction.

Cyclohexane Consensus Reports

Community Right-To-Know List.

Cyclohexane Standards and Recommendations

OSHA PEL: TWA 300 ppm
ACGIH TLV: TWA 100 ppm
DFG MAK: 200 ppm (720 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Cyclohexane Analytical Methods

For occupational chemical analysis use NIOSH: Hydrocarbons.

Cyclohexane Specification

The Cyclohexane is an organic compound with the formula C6H12. The IUPAC name of this chemical is cyclohexane. With the CAS registry number 110-82-7, the product's categories are Analytical Chemistry; Solvents for HPLC & Spectrophotometry; Solvents for Spectrophotometry; HPLC Solvents; Aluminum Bottles; Solvent Bottles; Solvents; Alpha Sort; C; CAlphabetic; CO - CZ; Volatiles/Semivolatiles; CO - CZChemical Class; Chemical Class; Hydrocarbons; NeatsAnalytical Standards ;C-D, Puriss p.a. ACS; Analytical Reagents for General Use; Puriss p.a. ACS; Amber Glass Bottles; Spectrophotometric Grade Solvents; Spectrophotometric GradeSolvents; Anhydrous Grade SolventsSolvents; AnhydrousSolvents; Returnable Container Solvents; Carbon Steel Cans with NPT Threads; ReagentPlus(R) Solvent Grade Products; ReagentPlus(R)Semi-Bulk Solvents; ReagentPlus(R)Solvents; Pesticide Residue Analysis (PRA) Solvents Solvent Bottles; PRA; ACS Grade Solvents; ACS GradeSemi-Bulk Solvents; ACS GradeSolvents; Chromatography/CE Reagents; Pestanal/Residue Analysis; Solvents - GC/SH; LC-MS Plus and Gradient; Spectroscopy; UV/Vis Solvents; UV/Visible (UV/VIS) Spectroscopy. Besides, it is colorless liquid, which should be stored in in a cool and well-ventilated place.

Physical properties about Cyclohexane are: (1)ACD/LogP: 3.16; (2)ACD/LogD (pH 5.5): 3.163; (3)ACD/LogD (pH 7.4): 3.163; (4)ACD/BCF (pH 5.5): 149.118; (5)ACD/BCF (pH 7.4): 149.118; (6)ACD/KOC (pH 5.5): 1251.474; (7)ACD/KOC (pH 7.4): 1251.474; (8)Index of Refraction: 1.433; (9)Molar Refractivity: 27.67 cm3; (10)Molar Volume: 106.454 cm3; (11)Polarizability: 10.969×10-24cm3; (12)Surface Tension: 25.943 dyne/cm; (13)Density: 0.791 g/cm3; (14)Enthalpy of Vaporization: 29.97 kJ/mol; (15)Boiling Point: 80.719 °C at 760 mmHg; (16)Vapour Pressure: 93.669 mmHg at 25°C.

Preparation: this chemical can be quantitatively produced from benzene by hydrogenation over either a nickel or a platinum catalyst at 210 °C  and 350 to 500 psi hydrogen. Several reactors may be used in series and the yield is over 99 percent.
C6H6 + 3H2 → C6H12

Uses of Cyclohexane: commercially most of cyclohexane produced is converted into cyclohexanone-cyclohexanol mixture (or "KA oil") by catalytic oxidation. KA oil is then used as a raw material for adipic acid and caprolactam. Practically, if the cyclohexanol content of KA oil is higher than cyclohexanone, it is more likely(economical) to be converted into adipic acid, and the reverse case, caprolactam production is more likely. Such ratio in KA oil can be controlled by selecting suitable oxidation catalyst. Some of cyclohexane is used as an organic solvent. Cyclohexane is also used for calibration of Differential scanning calorimetry (DSC) instruments, because of a convenient crystal-crystal transition at -87.1 C.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. Please keep away from sources of ignition - No smoking and take precautionary measures against static discharges. Besides, this chemical is irritating to skin and may cause lung damage if swallowed. When you are using it, avoid contact with eyes and avoid release to the environment. Refer to special instructions/safety data sheet. This material and its container must be disposed of as hazardous waste.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CCCCC1
(2)InChI: InChI=1/C6H12/c1-2-4-6-5-3-1/h1-6H2
(3)InChIKey: XDTMQSROBMDMFD-UHFFFAOYAZ
(4)Std. InChI: InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
(5)Std. InChIKey: XDTMQSROBMDMFD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LC50 inhalation 70gm/m3 (70000mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mouse LCLo inhalation 70gm/m3/2H (70000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 41, 1982.
mouse LD50 oral 813mg/kg (813mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 17, 1974.
rabbit LCLo inhalation 89600mg/m3/1H (89600mg/m3) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 323, 1943.
rabbit LD skin > 180gm/kg (180000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.
rabbit LDLo oral 5500mg/kg (5500mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.
rat LD50 oral 12705mg/kg (12705mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 699, 1971.

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