Synthesis of cyclohexane

Preparation of cyclohexane

Preparation of cyclohexane

Preparation of cyclohexane

For the preparation of nickel catalyst, small pieces of pumice stone of a convenient size are soaked in a concentrated solution of nickel nitrate in distilled water, and heated in a basin over a free flame until the nitrate has been converted into the nickel oxide. Alternatively, the pumice is impregnated with a paste of its own weight of nickel oxide and distilled water, and dried on a water bath. The nickel oxide is reduced by heating in a current of pure, thoroughly dried hydrogen in a combustion tube. A combustion tube 1 metre long is loosely packed for three-quarters of its length with the impregnated pumice stone, the layer being held in position with loose asbestos plugs. The tube is placed in a long cylindrical air bath fitted with 2 thermometers. The hydrogen for the preparation of  catalyst should be passed first through sodium hydroxide solution, then through conc. sulphuric acid, then over heated copper gauze or turnings (previously washed with alcohol to remove grease), and finally through a tower containing sticks of sodium hydroxide. Ordinary corks should be used, and not rubber stoppers, in making the connections to the combustion tube. Unpurified hydrogen must not be admitted, as otherwise the catalyst will be poisoned. It is convenient to have a by-pass in the form of a T-piece between the copper gauze and the sodium hydroxide tower. At first the hydrogen escapes through the by-pass. After the air has been expelled (a sample must be collected and tested) as far as the T-piece, the copper gauze tube is heated, and the current of hydrogen is then diverted through the tower into the combustion tube. Some should also be allowed to escape through the funnel B to remove air from its stem. When the air has been expelled completely, the air bath carrying the combustion tube is heated to 280° C. Air must not be allowed to enter the combustion tube from this until the end of the experiment. The reduction of the nickel oxide will take at least a week; the hydrogen is passed at the rate of about 300ml per minute. The reduction is accompanied by a colour change from black to a greyish-yellow, and is complete when no more steam is evolved, i.e., when a calcium chloride tube at the exit end of the combustion tube does not gain in weight after passing the exit gas through it for ¼ hour.

A glass apparatus for the preparation of cyclohexane

A glass apparatus for the preparation of cyclohexane

The benzene used should be thiophene free, the traces of sulphur and chlorine compounds completely inhibit the reaction. The benzene is passed at the rate of about 7 ml per minute into the combustion tube by means of a dropping funnel, B, whose stem, drawn out to a capillary, passes through one hole of the double-holed cork at A. The quantity of benzene used is obtained by weighing the amount in the funnel before and after the experiment. The temperature of the air bath should be 180-190° C, and the hydrogen should be passed at about 250 ml. per minute. When commencing to add the benzene at A, air must not be allowed to enter the tube; the vapour issuing from the combustion tube is condensed in a flask immersed in a freezing mixture. The condensate contains some unchanged benzene. This, when 40 g or more have been collected, is treated with a nitrating mixture of sulphuric and nitric acids. Cyclohexane is scarcely affected by this mixture while benzene is rapidly nitrated. It canot otherwise easily be separated from cyclohexane; their boiling points and freezing points are almost identical. After standing for 1 hour the top layer of oil is separated, well washed with water, and dried for 24 hours over calcium chloride. It is fractionated, and the fraction 78-85° C redistilled and collected between 80-82° C. Yield 80%. Calculated on the benzene volatilised (8.5 g cyclohexane per 10 g benzene). Almost theoretical allowing for unchanged benzene (11 g cyclohexane per 10 g benzene). Cyclohexane is colourless liquid; insoluble in water.

Systematic organic chemistry, by W. M. Cumming, 173-174, 1937.

IUPAC Name

cyclohexane

InChI

InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2

InChI Key

XDTMQSROBMDMFD-UHFFFAOYSA-N

Canonical SMILES

C1CCCCC1

MeSH Synonyms

Cyclohexane

Depositor-Supplied Synonyms

CYCLOHEXANE, Hexamethylene, Hexanaphthene, Hexahydrobenzene, Cyclohexan, Cykloheksan, 110-82-7, Cicloesano, Cyclohexaan, Benzene, hexahydro-, Polycyclohexane, Benzenehexahydride, hexahydro-Benzene, Poly(cyclohexane), RCRA waste number U056, Cyclohexaan [Dutch], Cyclohexan [German], Cicloesano [Italian], Cykloheksan [Polish], Caswell No. 269, RCRA waste no. U056, NSC 406835, UNII-48K5MKG32S, HSDB 60, CCRIS 3928, CHEBI:29005, XDTMQSROBMDMFD-UHFFFAOYSA-N, EINECS 203-806-2, UN1145, EPA Pesticide Chemical Code 025901, AI3-08222, Cyclohexane, oxidized, non-volatile residue, Ciclohexano, Zyklohexan, cyclo-hexane, Cyclohexane,oxidized, Cyclohexane, homopolymer, ACMC-1BUC3, CYCLOHEXANE- D12, DSSTox_CID_1923, bmse000545, WLN: L6TJ, AC1L1Q7Q, DSSTox_RID_76404, DSSTox_GSID_21923, ghl.PD_Mitscher_leg0.242, KSC176E2J, CHEMBL15980, 15329_RIEDEL, 227048_ALDRICH, 33117_RIEDEL, 34496_RIEDEL, 442531_SUPELCO, 48K5MKG32S, 650455_ALDRICH, 676861_ALDRICH, 28918_FLUKA, 28918_SIGMA, 28920_FLUKA, 28935_FLUKA, 34496_FLUKA, CTK0H6224, MolPort-001-785-799, 15329_SIAL, 28935_SIAL, 33117_SIAL, 34855_SIAL, LTBB002303, 154741_SIAL, 179191_SIAL, 227048_SIAL, 650455_SIAL, 676861_SIAL, ZINC1532203, EINECS 270-147-5, Tox21_201087, ANW-56408, LS-516, NSC406835, STL283116, AKOS000119975, ZINC100503963, ZINC108957648, ZINC111873857, CYCLOHEXANE, HPLC/SPECTRO GRADE, DB03561, MCULE-3136361765, NSC-406835, UN 1145, NCGC00248918-01, NCGC00258639-01, AN-22625, CAS-110-82-7, CJ-24168, KB-76252, OR034049, OR247837, OR257144, Cyclohexane [UN1145] [Flammable liquid], TR-002195, TX-017501, Cyclohexane [UN1145] [Flammable liquid], FT-0624180, FT-0624182, FT-0632535, 5374-EP2269975A2, 5374-EP2269977A2, 5374-EP2269986A1, 5374-EP2269989A1, 5374-EP2269990A1, 5374-EP2269993A1, 5374-EP2269997A2, 5374-EP2270001A1, 5374-EP2270003A1, 5374-EP2270006A1, 5374-EP2270008A1, 5374-EP2270010A1, 5374-EP2270014A1, 5374-EP2270113A1, 5374-EP2270114A1, 5374-EP2272516A2, 5374-EP2272517A1, 5374-EP2272537A2, 5374-EP2272822A1, 5374-EP2272825A2, 5374-EP2272826A1, 5374-EP2272831A1, 5374-EP2272848A1, 5374-EP2272935A1, 5374-EP2274983A1, 5374-EP2275401A1, 5374-EP2275407A1, 5374-EP2275410A1, 5374-EP2275414A1, 5374-EP2275415A2, 5374-EP2275419A2, 5374-EP2275469A1, 5374-EP2277848A1, 5374-EP2277882A1, 5374-EP2277898A2, 5374-EP2280000A1, 5374-EP2280005A1, 5374-EP2280006A1, 5374-EP2280009A1, 5374-EP2280011A1, 5374-EP2280014A2, 5374-EP2281812A1, 5374-EP2281813A1, 5374-EP2281815A1, 5374-EP2281818A1, 5374-EP2281820A2, 5374-EP2281822A1, 5374-EP2284148A1, 5374-EP2284149A1, 5374-EP2284157A1, 5374-EP2284174A1, 5374-EP2286915A2, 5374-EP2287147A2, 5374-EP2287152A2, 5374-EP2287153A1, 5374-EP2287154A1, 5374-EP2287159A1, 5374-EP2287160A1, 5374-EP2287168A2, 5374-EP2287940A1, 5374-EP2289509A2, 5374-EP2289876A1, 5374-EP2289878A1, 5374-EP2289879A1, 5374-EP2289884A1, 5374-EP2289887A2, 5374-EP2289888A2, 5374-EP2289891A2, 5374-EP2289893A1, 5374-EP2289897A1, 5374-EP2289965A1, 5374-EP2292592A1, 5374-EP2292596A2, 5374-EP2292611A1, 5374-EP2292612A2, 5374-EP2292617A1, 5374-EP2292621A1, 5374-EP2292629A1, 5374-EP2292630A1, 5374-EP2295408A1, 5374-EP2295410A1, 5374-EP2295426A1, 5374-EP2295427A1, 5374-EP2295430A2, 5374-EP2295431A2, 5374-EP2298729A1, 5374-EP2298731A1, 5374-EP2298735A1, 5374-EP2298745A1, 5374-EP2298746A1, 5374-EP2298754A1, 5374-EP2298761A1, 5374-EP2298763A1, 5374-EP2298767A1, 5374-EP2298772A1, 5374-EP2298828A1, 5374-EP2301544A1, 5374-EP2301627A1, 5374-EP2301909A1, 5374-EP2301918A1, 5374-EP2301919A1, 5374-EP2301934A1, 5374-EP2301939A1, 5374-EP2301983A1, 5374-EP2302003A1, 5374-EP2305250A1, 5374-EP2305254A1, 5374-EP2305625A1, 5374-EP2305627A1, 5374-EP2305642A2, 5374-EP2305649A1, 5374-EP2305650A1, 5374-EP2305667A2, 5374-EP2305675A1, 5374-EP2305679A1, 5374-EP2305682A1, 5374-EP2305683A1, 5374-EP2305685A1, 5374-EP2305686A1, 5374-EP2305688A1, 5374-EP2305808A1, 5374-EP2305825A1, 5374-EP2308471A1, 5374-EP2308510A1, 5374-EP2308562A2, 5374-EP2308812A2, 5374-EP2308832A1, 5374-EP2308838A1, 5374-EP2308839A1, 5374-EP2308848A1, 5374-EP2308849A1, 5374-EP2308850A1, 5374-EP2308851A1, 5374-EP2308857A1, 5374-EP2308858A1, 5374-EP2308861A1, 5374-EP2308865A1, 5374-EP2308876A1, 5374-EP2308879A1, 5374-EP2308926A1, 5374-EP2309564A1, 5374-EP2309584A1, 5374-EP2311796A1, 5374-EP2311797A1, 5374-EP2311798A1, 5374-EP2311799A1, 5374-EP2311801A1, 5374-EP2311802A1, 5374-EP2311803A1, 5374-EP2311808A1, 5374-EP2311813A1, 5374-EP2311816A1, 5374-EP2311817A1, 5374-EP2311821A1, 5374-EP2311822A1, 5374-EP2311824A1, 5374-EP2311829A1, 5374-EP2311830A1, 5374-EP2311837A1, 5374-EP2311839A1, 5374-EP2311841A1, 5374-EP2311842A2, 5374-EP2311846A1, 5374-EP2314295A1, 5374-EP2314558A1, 5374-EP2314579A1, 5374-EP2314583A1, 5374-EP2314585A1, 5374-EP2314587A1, 5374-EP2314589A1, 5374-EP2316452A1, 5374-EP2316824A1, 5374-EP2316837A1, 5374-EP2371797A1, 5374-EP2371798A1, 5374-EP2371800A1, 5374-EP2371804A1, 5374-EP2371811A2, 5374-EP2371814A1, 5374-EP2371831A1, 5374-EP2374454A1, 5374-EP2375479A1, 5374-EP2376421A1, 5374-EP2376422A1, 5374-EP2377844A2, 5374-EP2377845A1, 5374-EP2377847A1, 5374-EP2380568A1, 5374-EP2380871A1, 5374-EP2380874A2, 5611-EP2270101A1, 5611-EP2272822A1, 5611-EP2272832A1, 5611-EP2272843A1, 5611-EP2275469A1, 5611-EP2281817A1, 5611-EP2281818A1, 5611-EP2284169A1, 5611-EP2287161A1, 5611-EP2287162A1, 5611-EP2287940A1, 5611-EP2289518A1, 5611-EP2292231A1, 5611-EP2292589A1, 5611-EP2292597A1, 5611-EP2292611A1, 5611-EP2295414A1, 5611-EP2298747A1, 5611-EP2298828A1, 5611-EP2301922A1, 5611-EP2305248A1, 5611-EP2305641A1, 5611-EP2311850A1, 5611-EP2371811A2, 5611-EP2372804A1, 5611-EP2374783A1, 5611-EP2377841A1, 5611-EP2378585A1, C11249, 56779-EP2272846A1, 56779-EP2275408A1, 56779-EP2275422A1, 56779-EP2277868A1, 56779-EP2277869A1, 56779-EP2277870A1, 56779-EP2287147A2, 56779-EP2287158A1, 56779-EP2292608A1, 56779-EP2292616A1, 56779-EP2292625A1, 56779-EP2295422A2, 56779-EP2295436A1, 56779-EP2298076A1, 56779-EP2298077A1, 56779-EP2298305A1, 56779-EP2298769A1, 56779-EP2301353A1, 56779-EP2305031A1, 56779-EP2305034A1, 56779-EP2305035A1, 56779-EP2308866A1, 56779-EP2308878A2, 56779-EP2374791A1, 56779-EP2377844A2, 300044X, 3B4-0314, Cyclohexane,oxidized,non-acidicby-products,distn.lights, I14-17856, InChI=1/C6H12/c1-2-4-6-5-3-1/h1-6H, Cyclohexane, reaction product with oxygen, nonvolatile residue, 25012-93-5, 68411-76-7, 68512-15-2, 68609-05-2

Removed Synonyms

benzene, Cyclohexane-d12, Cyclohexyl radical, Cymal-4, HEXANE, CID8078, c0469, c0696, c0818, c0941, 5-CYCLOHEXYL-1-PENTYL-BETA-D-MALTOSIDE, C506365, CHX, 1735-17-7, 71-43-2, CM5, CVM, HEX

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