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US 5,492,875 AGranted
Catalyst for nucleophilic aromatic substitutions
AssigneeHoechst Aktiengesellschaft
InventorsThomas Schach, Theodor Papenfuhs
Life of this patent
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Abstract
A catalyst consisting essentially of a quaternary ammonium compound, comprising at least one linear or branched alkoxypolyoxyalkyl chain, and a quaternary ammonium or phosphonium salt or a polyether, or a mixture of each of the specified compounds, is suitable for accelerating, or making possible for the first time, many nucleophilic aromatic substitutions.
Claims10
A catalyst suitable for nucleophilic substitution, consisting essentially of:
- a mixture of a component a) and a component b), wherein component a) is at least one quaternary ammonium compound of the formula (1) ##STR3## in which R.sup.1, R.sup.2 and R.sup.3 are identical or different and are a linear or branched alkoxypolyoxyalkyl 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 linear 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;
- a linear 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, with the substituents being halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro or cyano;
- R.sup.4 is a linear or branched alkoxypolyoxyalkyl radical of the formula --(C.sub.m H.sub.2m O).sub.p R.sup.5, wherein R.sup.5, m, and p are as defined above, and;
- X is an inorganic anion;
- and
- component b) is at least one quaternary ammonium salt or at least one phosphonium salt of the formula (2) ##STR4## 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 1 to 22 carbon atoms;
- or an unsubstituted or substituted aryl radical or a C.sub.1 -C.sub.4 -alkyl-aryl radical, with aryl being phenyl or napthyl, and the said substituents are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro or cyano;
- and
- Y is N or P;
- or
- the mixture consists essentially of component a) as defined above, and a component c), which is at least one polyether of the formula (3)
- R.sup.10 --(O--C.sub.x H.sub.2x).sub.r --OR.sup.11 ( 3),
- in which
- R.sup.10 and R.sup.11 are identical or different and are hydrogen or a linear or branched alkyl radical having from 1 to 16 carbon atoms,
- x is an integer from 2 to 6 and
- r is a number from 0 to 20;
- or
- the mixture consists essentially of component a) as defined above, and a crown ether;
- or
- the mixture consists essentially of component a) as defined above, component b) as defined above, and component c) as defined above.
19 more elements
Dependencies are inferred from the claim text.