Phosphonite ligands and their use in hydrocyanation
View Patent ↗Disclosed herein are processes for hydrocyanation and isomerization of olefins by using at least one multidentate phosphonite ligands, including organometallic phosphonite ligands with a Group VIII metal or Group VIII metal compound, and optionally, a Lewis acid promoter.
1. A hydrocyanation process, said process, said process comprising: contacting an acyclic and aliphatic ethylenically unsaturated olefin compound with HCN in the presence of a catalyst composition, wherein said catalyst composition comprises a Group VIII metal and a phosphonite ligand wherein the ligand has a structure:
wherein the X groups independently are selected from the group consisting of unbridged substituted and unsubstituted organic aromatic groups, and when X is substituted, the substituent on X is independently selected from the group consisting of C1 to C12 alkyl, perfluoroalkyl, cycloalkyl, alkoxy, acetal, ketal, alkylaryl, aryl, 1,3-dioxolane, cyano, and hydrogen and wherein the Q groups independently are selected from the group consisting of substituted and unsubstituted divalent aromatic and non aromatic hydrocarbon radicals, and when Q is substituted, the substituent on the Q groups is independently selected from the group consisting of C1 to C12 alkyl, cycloalkyl, alkoxy, alkylaryl, aryl, pyran, and cyano, and L is a linking group selected from the group consisting of —CR1R2-, —O—, —S—, —CO— (wherein each of R1-R2 are independent of one another, are a hydrogen atom, a C1-12 alkyl group, or an aryl group), and each of m and m′ which are independent of each other, are 0 or 1.
2. A hydrocyanation process according to claim 1 wherein X is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and combinations thereof.
3. A hydrocyanation process according to claim 1 wherein the X is selected from the group consisting of:
4. A hdrocyanation process according to claim 1 wherein said acyclic and aliphatic ethylenically unsaturated olefin compound is a conjugated C 4 to C 20 diene.
5. The process of claim 1 wherein the acyclic and aliphatic ethylenically unsaturated olefin compound is 1,3-butadiene.
6. The process of claim 1 wherein reactants are in the liquid phase.
7. The process of claim 1 wherein the Group VIII metal is selected from the group consisting of nickel, cobalt, and palladium.
8. The process of claim 1 wherein said Group VIII metal is zero-valent nickel.
9. The process of claim 1 wherein the acyclic and aliphatic ethylenically unsaturated olefin compound is 3- or 4-pentenenitrile or mixture thereof.