Synthesis of benzene

Preparation of benzene

Preparation of benzene from aniline

Preparation of benzene from aniline

Preparation of benzene from aniline from aniline

50 g of aniline is dissolved in a mixture of 150 g of concentrated hydrochloric acid and 300 ml of water. This solution is cooled with ice, and treated with a solution of 50 g of sodium nitrite in 150 ml of water.  When diazotization reaction is complete the benzenediazonium chloride is allowed to flow carefully into a cooled solution of 100 g sodium hydroxide in 300 ml of water. A 200 g of stannous chloride in 500 ml of water is treated with concentrated solution of sodium hydroxide until the precipitated stannous oxide is redissolved in the excess of the alkali. Well cooled with ice-water benzenediazonium chloride solution is gradually treated with small portions of sodium stannite solution, allowing the evolution of nitrogen gas to ceased before adding more of the sodium stannite. When reaction is complete, the flask is connected with a distillation head and condenser, and heated to boiling. The benzene formed passes over first, and is collected yielding 30-40 g of final product. Pure product is obtained by redistillation collecting fraction boiling at 81° C.

The practical methods of organic chemistry, by L. Gattermann, 210, 1909

Preparation of benzene from calcium benzoate

Preparation of benzene from calcium benzoate

Preparation of benzene from calcium benzoate

300 g of powdered calcium benzoate is mixed with 600 g of soda-lime, and the mixture is distilled by heating with gas burner, yielding water and a light brown oil with strong smell of benzene. The benzene is separated from the water by a means of a separatory funnel. Crude benzene is dried over calcium chloride, and redistilled yielding pure benzene with boiling point 81° C.

A class-book of organic chemistry, by J. B. Cohen, 249, 1918

IUPAC Name

benzene

InChI

InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H

InChI Key

UHOVQNZJYSORNB-UHFFFAOYSA-N

Canonical SMILES

C1=CC=CC=C1

MeSH Synonyms

Benzene, Benzol, Benzole, Cyclohexatriene

Depositor-Supplied Synonyms

benzene, benzol, benzole, Cyclohexatriene, Pyrobenzole, Benzine, Phenyl hydride, Pyrobenzol, Benzen, Phene, Mineral naphtha, Coal naphtha, Bicarburet of hydrogen, [6]Annulene, Benzolene, Benzin, Motor benzol, Carbon oil, 71-43-2, Polystream, Benzeen, Benzolo, Fenzen, Nitration benzene, (6)Annulene, Benzol 90, Benzol diluent, Benzene, pure, Rcra waste number U019, NCI-C55276, Benzeen [Dutch], Benzen [Polish], Fenzen [Czech], Benzolo [Italian], Benzine (Obs.), Benzin (Obs.), Caswell No. 077, CHEBI:16716, 1,3,5-cyclohexatriene, NSC 67315, CCRIS 70, UN 1114, HSDB 35, CHEMBL277500, UHOVQNZJYSORNB-UHFFFAOYSA-N, UNII-J64922108F, EINECS 200-753-7, UN1114, EPA Pesticide Chemical Code 008801, Benzene (including benzene from gasoline), Benzene-UL-14C, AI3-00808, BNZ, 2,5-cyclohexadien-1,4-ylene, 26181-88-4, RNG, Benzinum, Benzolum, Aromatic alkane, benzene-, 1hyz, 1swi, Benzene-U-14C, {[6]Annulene}, PETROLEUM ETHER, 2z9g, 4i7j, BENZENE, ACS, ACMC-209snd, Benzene + aniline combo, DSSTox_CID_135, WLN: RH, Epitope ID:116867, AC1L18SP, DSSTox_RID_79433, DSSTox_GSID_39242, ghl.PD_Mitscher_leg0.503, 48503_SUPELCO, 270709_ALDRICH, 32212_RIEDEL, 401765_ALDRICH, 676985_ALDRICH, 12540_FLUKA, 12553_FLUKA, HMDB01505, Benzene, labeled with carbon-14, 1l83, 220l, 223l, 311855_SIGMA, 322644_SIGMA, MolPort-000-871-944, 12553_SIAL, 32212_SIAL, 154628_SIAL, 270709_SIAL, 319953_SIAL, 401765_SIAL, 676985_SIAL, ACT02832, NSC67315, Tox21_202487, ANW-41399, NSC-67315, STL264205, AKOS008967253, LS-1605, MCULE-4899719484, RL04726, RTR-002195, Benzene [UN1114] [Flammable liquid], CAS-71-43-2, Benzene [UN1114] [Flammable liquid], NCGC00090744-01, NCGC00090744-02, NCGC00163890-01, NCGC00163890-02, NCGC00260036-01, 8030-30-6, AJ-24530, AN-23800, AN-24993, KB-47520, ZB015460, AB1007259, B0020, Benzene, labeled with carbon-14 and tritium, FT-0080146, FT-0622636, FT-0622667, FT-0656867, FT-0657604, J64922108F, Q0038, Q0042, S0631, 3945-EP0930075A1, 3945-EP1441224A2, 3945-EP2269977A2, 3945-EP2269978A2, 3945-EP2269985A2, 3945-EP2269986A1, 3945-EP2269987A1, 3945-EP2269988A2, 3945-EP2269989A1, 3945-EP2269990A1, 3945-EP2269991A2, 3945-EP2269993A1, 3945-EP2269995A1, 3945-EP2270000A1, 3945-EP2270006A1, 3945-EP2270008A1, 3945-EP2270010A1, 3945-EP2270113A1, 3945-EP2270114A1, 3945-EP2272516A2, 3945-EP2272537A2, 3945-EP2272813A2, 3945-EP2272817A1, 3945-EP2272822A1, 3945-EP2272825A2, 3945-EP2272828A1, 3945-EP2272832A1, 3945-EP2272839A1, 3945-EP2272840A1, 3945-EP2272841A1, 3945-EP2272849A1, 3945-EP2272935A1, 3945-EP2272972A1, 3945-EP2272973A1, 3945-EP2275395A2, 3945-EP2275401A1, 3945-EP2275404A1, 3945-EP2275407A1, 3945-EP2275410A1, 3945-EP2275411A2, 3945-EP2275414A1, 3945-EP2275417A2, 3945-EP2275418A1, 3945-EP2275427A1, 3945-EP2275469A1, 3945-EP2277858A1, 3945-EP2277862A2, 3945-EP2277867A2, 3945-EP2277871A1, 3945-EP2277872A1, 3945-EP2277874A1, 3945-EP2277875A2, 3945-EP2277878A1, 3945-EP2277881A1, 3945-EP2279750A1, 3945-EP2280000A1, 3945-EP2280001A1, 3945-EP2280003A2, 3945-EP2280005A1, 3945-EP2280007A1, 3945-EP2280009A1, 3945-EP2280011A1, 3945-EP2281559A1, 3945-EP2281563A1, 3945-EP2281810A1, 3945-EP2281817A1, 3945-EP2281818A1, 3945-EP2281821A1, 3945-EP2282636A2, 3945-EP2284150A2, 3945-EP2284151A2, 3945-EP2284152A2, 3945-EP2284153A2, 3945-EP2284155A2, 3945-EP2284156A2, 3945-EP2284157A1, 3945-EP2284159A1, 3945-EP2284162A2, 3945-EP2284163A2, 3945-EP2284164A2, 3945-EP2284169A1, 3945-EP2284174A1, 3945-EP2284178A2, 3945-EP2284920A1, 3945-EP2286811A1, 3945-EP2286812A1, 3945-EP2287140A2, 3945-EP2287141A1, 3945-EP2287147A2, 3945-EP2287148A2, 3945-EP2287150A2, 3945-EP2287152A2, 3945-EP2287153A1, 3945-EP2287154A1, 3945-EP2287161A1, 3945-EP2287162A1, 3945-EP2287165A2, 3945-EP2287166A2, 3945-EP2287940A1, 3945-EP2289509A2, 3945-EP2289518A1, 3945-EP2289868A1, 3945-EP2289871A1, 3945-EP2289876A1, 3945-EP2289879A1, 3945-EP2289884A1, 3945-EP2289887A2, 3945-EP2289888A2, 3945-EP2289892A1, 3945-EP2289965A1, 3945-EP2292227A2, 3945-EP2292231A1, 3945-EP2292576A2, 3945-EP2292589A1, 3945-EP2292590A2, 3945-EP2292592A1, 3945-EP2292593A2, 3945-EP2292595A1, 3945-EP2292597A1, 3945-EP2292599A1, 3945-EP2292606A1, 3945-EP2292611A1, 3945-EP2292612A2, 3945-EP2292615A1, 3945-EP2292617A1, 3945-EP2292620A2, 3945-EP2292630A1, 3945-EP2295399A2, 3945-EP2295402A2, 3945-EP2295406A1, 3945-EP2295409A1, 3945-EP2295411A1, 3945-EP2295412A1, 3945-EP2295413A1, 3945-EP2295414A1, 3945-EP2295415A1, 3945-EP2295418A1, 3945-EP2295419A2, 3945-EP2295421A1, 3945-EP2295422A2, 3945-EP2295424A1, 3945-EP2295425A1, 3945-EP2295426A1, 3945-EP2295427A1, 3945-EP2295429A1, 3945-EP2295432A1, 3945-EP2295433A2, 3945-EP2295438A1, 3945-EP2295439A1, 3945-EP2295441A2, 3945-EP2295503A1, 3945-EP2298729A1, 3945-EP2298731A1, 3945-EP2298732A1, 3945-EP2298735A1, 3945-EP2298745A1, 3945-EP2298746A1, 3945-EP2298747A1, 3945-EP2298750A1, 3945-EP2298753A1, 3945-EP2298756A1, 3945-EP2298763A1, 3945-EP2298767A1, 3945-EP2298768A1, 3945-EP2298770A1, 3945-EP2298772A1, 3945-EP2298774A1, 3945-EP2298777A2, 3945-EP2298778A1, 3945-EP2298783A1, 3945-EP2298828A1, 3945-EP2300430A1, 3945-EP2301534A1, 3945-EP2301627A1, 3945-EP2301911A1, 3945-EP2301912A2, 3945-EP2301913A1, 3945-EP2301914A1, 3945-EP2301916A2, 3945-EP2301918A1, 3945-EP2301919A1, 3945-EP2301921A1, 3945-EP2301922A1, 3945-EP2301924A1, 3945-EP2301926A1, 3945-EP2301928A1, 3945-EP2301933A1, 3945-EP2301934A1, 3945-EP2301936A1, 3945-EP2301937A1, 3945-EP2302003A1, 3945-EP2305219A1, 3945-EP2305250A1, 3945-EP2305625A1, 3945-EP2305627A1, 3945-EP2305636A1, 3945-EP2305637A2, 3945-EP2305640A2, 3945-EP2305641A1, 3945-EP2305642A2, 3945-EP2305647A1, 3945-EP2305648A1, 3945-EP2305649A1, 3945-EP2305650A1, 3945-EP2305651A1, 3945-EP2305655A2, 3945-EP2305658A1, 3945-EP2305668A1, 3945-EP2305672A1, 3945-EP2305676A1, 3945-EP2305679A1, 3945-EP2305683A1, 3945-EP2305687A1, 3945-EP2305769A2, 3945-EP2305825A1, 3945-EP2308510A1, 3945-EP2308562A2, 3945-EP2308812A2, 3945-EP2308828A2, 3945-EP2308832A1, 3945-EP2308838A1, 3945-EP2308839A1, 3945-EP2308844A2, 3945-EP2308845A2, 3945-EP2308846A2, 3945-EP2308848A1, 3945-EP2308849A1, 3945-EP2308850A1, 3945-EP2308851A1, 3945-EP2308852A1, 3945-EP2308853A1, 3945-EP2308854A1, 3945-EP2308855A1, 3945-EP2308857A1, 3945-EP2308863A1, 3945-EP2308865A1, 3945-EP2308868A1, 3945-EP2308869A1, 3945-EP2308872A1, 3945-EP2308874A1, 3945-EP2308876A1, 3945-EP2308877A1, 3945-EP2308882A1, 3945-EP2308926A1, 3945-EP2309564A1, 3945-EP2309584A1, 3945-EP2311451A1, 3945-EP2311464A1, 3945-EP2311796A1, 3945-EP2311797A1, 3945-EP2311798A1, 3945-EP2311799A1, 3945-EP2311802A1, 3945-EP2311803A1, 3945-EP2311804A2, 3945-EP2311807A1, 3945-EP2311808A1, 3945-EP2311811A1, 3945-EP2311813A1, 3945-EP2311814A1, 3945-EP2311820A1, 3945-EP2311825A1, 3945-EP2311827A1, 3945-EP2311828A1, 3945-EP2311829A1, 3945-EP2311830A1, 3945-EP2311839A1, 3945-EP2311840A1, 3945-EP2311842A2, 3945-EP2314558A1, 3945-EP2314576A1, 3945-EP2314577A1, 3945-EP2314579A1, 3945-EP2314581A1, 3945-EP2314583A1, 3945-EP2314584A1, 3945-EP2314585A1, 3945-EP2314586A1, 3945-EP2314587A1, 3945-EP2314589A1, 3945-EP2314593A1, 3945-EP2315303A1, 3945-EP2315502A1, 3945-EP2316450A1, 3945-EP2316459A1, 3945-EP2316826A1, 3945-EP2316829A1, 3945-EP2316831A1, 3945-EP2316832A1, 3945-EP2316833A1, 3945-EP2316836A1, 3945-EP2316837A1, 3945-EP2371795A1, 3945-EP2371810A1, 3945-EP2371811A2, 3945-EP2371812A1, 3945-EP2371831A1, 3945-EP2372804A1, 3945-EP2374787A1, 3945-EP2374790A1, 3945-EP2377610A2, 3945-EP2377611A2, 3945-EP2377847A1, 3945-EP2377849A2, 3945-EP2378585A1, 3945-EP2379677A2, 3945-EP2380568A1, 3945-EP2380867A1, 3945-EP2380873A1, 3945-EP2380874A2, C01407, 77823-EP2272846A1, 77823-EP2277862A2, 77823-EP2277868A1, 77823-EP2277869A1, 77823-EP2277870A1, 77823-EP2287158A1, 77823-EP2292608A1, 77823-EP2292625A1, 77823-EP2295422A2, 77823-EP2295436A1, 77823-EP2298749A1, 77823-EP2298769A1, 77823-EP2300430A1, 77823-EP2305033A1, 77823-EP2308866A1, 77823-EP2379677A2, TRANSGENIC MODEL EVALUATION II (BENZENE), 142077-EP2270010A1, 142077-EP2292593A2, 300019X, 3B4-0001, InChI=1/C6H6/c1-2-4-6-5-3-1/h1-6, T5329368, I01-19671, I14-114049, 1053658-43-7, 174973-66-1, 54682-86-9

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