Improvements in the production of alpha, beta-unsaturated nitriles

    公开(公告)号:GB884548A

    公开(公告)日:1961-12-13

    申请号:GB751260

    申请日:1960-03-03

    Applicant: BASF AG

    Abstract: The invention comprises (1) the compounds alpha - cyclohexylidenyl - cyclohexylidene aceto - nitrile, 1,1-dimethoxy-2-methyl-3-cyano-propene(2), p gamma-tetrahydrofuramyloxy-beta-methylcrotonitrile and 1,4-bis-(21cyano-propen-(11)-yl-(11))-benzene; and (2) the preparation of these and other alpha, beta-unsaturated nitriles containing optional halogen, alkoxy, hydroxyl, nitro, amino, carboxyl, carboxylic ester and acyloxy substituents by reacting a phosphonate or phosphinate of the formula in which R1 is an aliphatic, cycloaliphatic or araliphatic radical attached to the phosphorus atom by way of an oxygen atom, R2 has the same meaning as R1 and may also be an aliphatic, cycloaliphatic, araliphatic or aromatic radical attached to the phosphorus atom by means of carbon atom, or in which R1 and R2 may also be common members of a heterocyclic ring carrying optional substituents and containing the phosphorus atom and two oxygen atoms directly attached thereto, R3, R4 and R5 are hydrogen or C1-4 alkyl radicals and n is 0, 1, 2, 3 or 4, with a carbonyl compound in the presence of a proton acceptor. The carbonyl compound may be an aliphatic, aromatic or heterocyclic aldehyde or ketone. Suitable proton acceptors are alkali or alkaline earth metal hydroxides, alcoholates or amides, strongly basic amines or basic ion exchange resins. The reaction may be conducted in water or an inert organic solvent. Phosphinates and phosphonates of the above general formula may be prepared by reacting halonitriles with a phosphinate or phosphorous acid ester, respectively.

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