Synthesis of adiponitrile

Preparation of adiponitrile

Preparation of adiponitrile

Preparation of adiponitrile

30 g of dry sodium cyanide (dried at 110º C overnight a) are mixed with 150 ml of dry dimethyl sulfoxide. The mixture is added to the flask fitted with a stirrer, reflux condenser, dropping funnel, and thermometer. The thick reaction slurry is heated to 90º C and the heating then  is stopped.  0.25 mole of 1,4-dichlorobutane is slowly added to the stirred mixture causing the temperature to increase immediately. The rate of addition is such that the temperature of the reaction did not go above about 160º C. After all the 1,4-dichlorobutane is added the mixture is stirred for additional 10 min. more, or until the temperature dropped below 50º C. After the reaction is complete the mixture is cooled to room temperature and 150 ml. of chloroform is added to the flask and this mixture is then poured into saturated sodium chloride solution. Enough water was added to dissolve precipitated salt and the chloroform layer was separated. The aqueous layer was extracted once with chloroform. The combined extracts were then washed twice with sodium chloride solution, dried, and distilled at 115º C/0.7 mmHg yielding 88% of the final product.

J. Org. Chem., 1960, 25 (2), pp 257–258

IUPAC Name

hexanedinitrile

InChI

InChI=1S/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2

InChI Key

BTGRAWJCKBQKAO-UHFFFAOYSA-N

Canonical SMILES

C(CCC#N)CC#N

MeSH Synonyms

adiponitrile, hexanedinitrile

Depositor-Supplied Synonyms

ADIPONITRILE, Hexanedinitrile, 1,4-Dicyanobutane, 111-69-3, Adipyldinitrile, Adipic acid dinitrile, Tetramethylene dicyanide, Adipodinitrile, Nitrile adipico, Tetramethylene cyanide, Adipic acid nitrile, Hexanedioic acid, dinitrile, NSC 7617, Hexanedioic acid dinitrile, Nitrile adipico [Italian], Adipinsaeuredinitril [German], CCRIS 4570, HSDB 627, BTGRAWJCKBQKAO-UHFFFAOYSA-N, EINECS 203-896-3, SBB060888, UN2205, BRN 1740005, AI3-11080, DSSTox_CID_1936, butane-1,4-dicarbonitrile, DSSTox_RID_76412, DSSTox_GSID_21936, CAS-111-69-3, Adipic dinitrile, Adipinsaeuredinitril, AC1L1QBT, WLN: NC4CN, ACMC-2099ae, AC1Q4S7T, UNII-SYT33B891I, SCHEMBL59340, D77001_ALDRICH, KSC175O9B, MLS002415709, SYT33B891I, CHEMBL2132938, CTK0H5790, NSC7617, MolPort-001-783-993, HMS2268I10, Adiponitrile [UN2205] [Poison], NSC-7617, ZINC1683668, EINECS 270-153-8, Tox21_202183, Tox21_300026, Adiponitrile [UN2205] [Poison], ANW-16308, AR-1H6668, LS-537, ZINC01683668, AKOS009031175, MCULE-6300737279, RP18903, RTR-002297, TRA0098590, UN 2205, Reaction product (adiponitrile-hydrogen), NCGC00090882-01, NCGC00090882-02, NCGC00090882-03, NCGC00254080-01, NCGC00259732-01, AJ-29771, AK117068, AN-25432, K894, KB-64541, LP057620, OR079756, SMR001252282, TR-002297, A0168, FT-0083166, FT-0606865, ST24030071, ST51046986, 4-02-00-01975 (Beilstein Handbook Reference), Hexanedinitrile, hydrogenated, high-boiling fraction, J-503989, I14-16587, 3B1-000442, InChI=1/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H, Adiponitrile, reaction product with hydrogen, high-boiling fraction, 68411-90-5

Removed Synonyms

UNII-VK98I9YW5M, C6H8N2, CID8128, 1124-63-6, 68511-79-5

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