Hydrocyanation of 2-pentenenitrile
The invention provides a process for hydrocyanation, comprising: contacting 2-pentenenitrile with hydrogen cyanide at a temperature in the range of about 0° C. to about 150° C. in the presence of at least one Lewis acid promoter and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one bidentate phosphite ligand selected from a member of the group represented by Formula I and Formula II, in which all like reference characters have the same meaning, except as further explicitly limited: wherein R 1 and R 5 are independently selected from the group consisting of C 1 to C 5 hydrocarbyl; and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 are independently selected from the group consisting of H and C 1 to C 4 hydrocarbyl.
1. A process for hydrocyanation, comprising:
contacting 2-pentenenitrile with hydrogen cyamide at a temperature in the range of about 0° C. to about 150° C. in the presence of at least one Lewis acid promoter and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one bidentate phosphite ligand selected from a member of the group represented by Formula I and Formula II, in which all like numbered substitutents have the same meaning, except as further explicitly limited:
wherein R 1 and R 5 are independently selected from the group consisting of C 1 to C 5 hydrocarbyl; and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 are independently selected from the group consisting of H and C 1 to C 4 hydrocarbyl.
2. The process of claim 1 wherein the bidentate phosphite ligand is selected from a member of the group represented by Formula I and Formula II, wherein
R 1 is methyl, ethyl, isopropyl or cyclopentyl;
R 2 is H or methyl;
R 3 is H or a C 1 to C 4 hydrocarbyl;
R 4 is H or methyl;
R 5 is methyl, ethyl or isopropyl; and
R 6 , R 7 and R 8 are independently selected from the group consisting of H and C 1 to C 4 hydrocarbyl.
3. The process of claim 1 , wherein the bidentate phosphite ligand is selected from a member of the group represented by Formula I, wherein R 1 , R 4 , and R 5 are methyl; R 2 , R 6 , R 7 and R 8 are H; and R 3 is C 1 to C 4 hydrocarbyl.
4. The process of claim 1 , wherein the bidentate phosphite ligand is selected from a member of the group represented by Formula I, wherein R 1 is isopropyl; R 2 is H; R 3 is C 1 to C 4 hydrocarbyl; R 4 is H or methyl; R 5 is methyl or ethyl; R 6 and R 8 are H or methyl; and R 7 is H, methyl or tertiary-butyl.
5. The process of claim 1 , wherein the bidentate phosphite ligand is selected from a member of the group represented by Formula II, wherein R 1 is isopropyl or cyclopentyl; R 5 is methyl or isopropyl; and R 2 , R 6 , R 7 , and R 8 are H.
6. The process of claim 1 , wherein the Lewis acid promoter comprises at least one compound selected from the group consisting of ZnCl 2 and FeCl 2 or a combination of such members.
7. The process of claim 1 , wherein the reaction temperature is in the range of about 25° C. to about 80° C.
8. The process of claim 1 , wherein the molar ratio of the Lewis acid promoter to the nickel present in the reaction ranges from about 1:10 to about 10:1.
9. The process of claim 1 wherein the catalyst precursor composition further comprises at least one monodentate phosphite ligand.