- One Synthetic Approach of Trimethylene cyanide
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Trimethylene cyanide (CAS NO.: ), with other name of Glutaronitrile, could be produced through the following synthetic routes.
In a 5-l. round-bottomed flask fitted with a stopper holding a reflux condenser and a separatory funnel are placed 294 g. (6 moles) of sodium cyanide and 300 cc. of water. The flask is heated on a steam bath until most of the sodium cyanide is in solution. This requires two to three hours. A solution of 500 g. (2.47 moles) of trimethylene bromide in 1 l. of 95 per cent alcohol is then added through the separatory funnel over a period of forty to sixty minutes. The mixture is refluxed for thirty to forty hours on a steam bath. Then the solvent is removed, preferably under reduced pressure, using an oil bath.
The residue, consisting of sodium bromide, sodium cyanide, and trimethylene cyanide, is extracted with 300–400 cc. of ethyl acetate, which dissolves the trimethylene cyanide and does not dissolve the inorganic salts. This solution is filtered and the salt washed once with about 100 cc. of ethyl acetate. The ethyl acetate is distilled at ordinary pressure and the residual liquid is distilled under reduced pressure. The yield of trimethylene cyanide boiling at 144–147°/13 mm. or 131–134°/10 mm. is 180–200 g. (77–86 per cent of the theoretical amount).
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