Patent ID: 6114589
Filing Date: 2000-09-05
Classification: C07B,C07C

Abstract:
A process for the preparation of fluorinated compounds of the formula (1 )Az.sub.x ArF.sub.w Cl.sub.(y-w) R.sub.z ( 1)in which Az independently of one another are identical or different and are a radical --F, --Cl, --Br, --NO.sub.2, --CN, --CF.sub.3, --CCl.sub.3, --CHO, --CO(C.sub.n H.sub.2n+1), where n is an integer from 1 to 10, --COX or --SO.sub.2 X, where X is F, Cl or Br, x is an integer from 1 to 3, Ar is a phenyl radical, pyridyl radical or naphthyl radical, w is an integer from 1 to y, y is an integer from 1 to 5,R independently of one another are identical or different and are H, a straight-chain or branched alkyl radical having from 1 to 10 carbon atoms or a straight-chain or branched alkoxy radical having from 1 to 10 carbon atoms,z is an integer from 1 to 5, where (x+y+z) is the number of all substitutable valences on the radical Ar, which comprises reacting a compound of the formula (2)Az.sub.x ArCl.sub.y R.sub.z ( 2),in which Az, x, Ar, y, R, z and (x+y+z) are as defined for formula 1, with an alkali metal fluoride or a mixture of alkali metal fluorides in the presence of a component a) or a mixture of component a) and at least one of components b), c), d) and e),component a) being one or more quaternary ammonium compounds of the formula (3) ##STR5## in which R.sup.1, R.sup.2 and R.sup.3 are identical or different and are a straight-chain or branched radical of the formula --(C.sub.m H.sub.2m O).sub.p R.sup.5, in which R.sup.5 is hydrogen or a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms, m is an integer from 1 to 10 and p is a number from 1 to 15; or a straight-chain or branched alkyl radical having from 1 to 30 carbon atoms;or an unsubstituted phenyl or naphthyl radical; or a substituted phenyl or naphthyl radical where the substituents are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro or cyano;R.sup.4 is a straight-chain or branched radical of the formula --(C.sub.m H.sub.2m O).sub.p R.sup.5 ; andX.sup..crclbar. is a monobasic acid radical or the equivalent of a polybasic acid radical,component b) being one or more amidophosphonium salts of the formula (4) ##STR6## in which A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, A.sup.7, A.sup.8 independently of one another are identical or different and are a straight-chain or branched alkyl or alkenyl having from 1 to 12 carbon atoms, cycloalkyl having from 4 to 8 carbon atoms, an aryl having from 6 to 12 carbon atoms, an aralkyl having from 7 to 12 carbon atoms, or A.sup.1 A.sup.2, A.sup.3 A.sup.4, A.sup.5 A.sup.6 and A.sup.7 A.sup.8 independently of one another are identical or different and are bonded together, directly or via O or N--A.sup.9, to give a ring having from 3 to 7 ring members, A.sup.9 is an alkyl having from 1 to 4 carbon atoms and X.sup.- is a monobasic acid radical or the equivalent of a polybasic acid radical,component c) being one or more quaternary ammonium compounds of the formula (5) ##STR7## in which R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are identical or different and are a straight-chain or branched alkyl radical having from 1 to 22 carbon atoms; or an unsubstituted or substituted aryl radical or a C.sub.1 -C.sub.4 -alkylaryl radical, where aryl is phenyl or naphthyl, and said substituents are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro or cyano; and X.sup.- is a monobasic acid radical or the equivalent of a polybasic acid radical;component d) being one or more quaternary phosphonium compounds of the formula (6) ##STR8## in which R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are identical or different and are a linear or branched alkyl radical having from 1 to 22 carbon atoms; or an unsubstituted or substituted aryl radical or aC.sub.1-C.sub.4 -alkylaryl radical, where aryl is phenyl or naphthyl, and said substituents are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro or cyano; and X.sup.- is a monobasic acid radical or the equivalent of a polybasic acid radical; component e) being one or more polyethers of the formula (7)R.sup.10 --(O--C.sub.a H.sub.2a).sub.b --OR.sup.11 ( 7)or crown ethers, where, in formula (7)R.sup.10 and R.sup.11 are identical or different and are a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms;a is an integer from 2 to 6 andb is an integer from 0 to 20, and carrying out the reaction at from 50 to 250.degree. C., removing the compound of the formula (1) formed during the reaction by distillation, and the compound of the formula (2) is fed to the reaction mixture at a rate corresponding to the rate at which the compound of the formula (1) is removed.