Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins
AssigneeE. I. Du Pont de Nemours and Company
InventorsKristina A. Kreutzer, Wilson Tam
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Abstract
Processes for hydrocyanation of nonconjugated aliphatic monoolefins or monoolefins conjugated to an ester group utilizing a catalyst precursor composition comprising an unsymmetrical bidentate phosphite ligand and zero-valent nickel, preferably in the presence of a Lewis acid promoter, to produce a terminal organonitrile. Catalyst precursor compositions are also disclosed.
Claims13
A process for hydrocyanation comprising reacting a monoolefin of Formula VII or IX with a source of HCN in the presence of a catalyst precursor composition comprising zero-valent nickel and a bidentate phosphite ligand of Formula I, to yield a terminal organonitrile of Formula VIII or X;
- ##STR19## wherein each R.sup.1 is independently a secondary or tertiary substituted hydrocarbyl of 3 to 12 carbon atoms;
- and
- each R.sup.2 is independently, H, X wherein X is Cl, F or Br, a C.sub.1 to C.sub.12 alkyl, or OR.sup.3 wherein R.sup.3 is C.sub.1 to C.sub.12 alkyl;
- and wherein said monoolefin and terminal organonitrile are ##STR20## wherein R.sup.19 is H, CN, CO.sub.2 R.sup.20, or perfluoroalkyl;
- y is 0 to 12;
- x is 0 to 12 when R.sup.19 is H, CO.sub.2 R.sup.20 or perfluoroalkyl;
- x is 1 to 12 when R.sup.19 is CN;
- and
- R.sup.20 is alkyl;
- or ##STR21## wherein R.sup.19 is H, CN, CO.sub.2 R.sup.20, or perfluoroalkyl;
- x is 0 to 12 when R.sup.19 is H, CO.sub.2 R.sup.20 or perfluoroalkyl;
- x is 1 to 12 when R.sup.19 is CN;
- and
- R.sup.20 is alkyl.
A process for hydrocyanation comprising reacting a nonconjugated acyclic aliphatic monoolefin or a monoolefin conjugated to an ester group;
- with a source of HCN in the presence of a catalyst precursor composition comprising zero-valent nickel and a bidentate phosphite ligand selected from the group consisting of Formulas II-VI as set forth below:
- ##STR23## wherein each R.sup.6 is independently a secondary or tertiary substituted hydrocarbyl of 3 to 12 carbon atoms;
- and
- each R.sup.7 is independently H, X wherein X is Cl, F or Br, a C.sub.1 to C.sub.12 alkyl, or OR.sup.8 wherein R.sup.8 is C.sub.1 to C.sub.12 alkyl;
- ##STR24## wherein each R.sup.9 is independently a secondary or tertiary substituted hydrocarbyl of 3 to 12 carbon atoms;
- each R.sup.10 is independently H, X wherein X is Cl, F or Br, a C.sub.1 to C.sub.12 alkyl, or OR.sup.8 wherein R.sup.8 is C.sub.1 to C.sub.12 alkyl;
- and
- each R.sup.11 is independently a branched or straight chain alkyl of up to 12 carbon atoms;
- ##STR25## wherein each R.sup.12 is independently a secondary or tertiary substituted hydrocarbyl of 3 to 12 carbon at oms;
- each R.sup.13 is independently H, X wherein X is Cl, F or Br, a C.sub.1 to C.sub.12 alkyl, or OR.sup.8 wherein R.sup.8 is C.sub.1 to C.sub.12 alkyl;
- and
- each R.sup.14 is independently a branched or straight chain alkyl of up to 12 carbon atoms;
- ##STR26## wherein each R.sup.15 is independently a secondary or tertiary substituted hydrocarbyl of 3 to 12 carbon atoms;
- and
- each R.sup.16 is independently H, X wherein X is Cl, F or Br, a C.sub.1 to C.sub.12 alkyl, or OR.sup.8 wherein R.sup.8 is C.sub.1 to C.sub.12 alkyl;
- and ##STR27## wherein each R.sup.17 is independently a secondary or tertiary substituted hydrocarbyl of 3 to 12 carbon atoms;
- and
- each R.sup.18 is independently H, X wherein X is Cl, F or Br, a C.sub.1 to C.sub.12 alkyl, or OR.sup.8 wherein R.sup.8 is C.sub.1 to C.sub.12 alkyl;
- and wherein said reaction is carried out to produce a terminal organonitrile.
Dependencies are inferred from the claim text.