Process for making 3-pentenenitrile by hydrocyanation of butadiene
View Patent ↗The invention provides a continuous process for the production of 3-pentenenitrile, comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a 1,3-butadiene-containing feed, and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one multidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, and a mixed phosphorus-containing ligand or a combination of such members; and (b) maintaining a residence time sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the reaction mixture.
1. A process for the continuous production of 3-pentenenitrile, comprising:
(a) continuously introducing feed comprising hydrogen cyanide, 1,3-butadiene, and a catalyst precursor composition to a reaction zone, wherein the molar ratio of the hydrogen cyanide in the feed to the 1,3-butadiene in the feed is in the range of about 0.90:1.00 to about 1.04:1.00, and wherein the catalyst precursor composition comprises a zero-valent nickel and at least one multidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, and a mixed phosphorus-containing ligand or a combination of such members;
(b) displacing a product mixture from the reaction zone by the feed which is continuously introduced into the reaction zone; and
(c) maintaining a residence time in the reaction zone sufficient to convert about 95% or more of the hydrogen cyanide and to produce the product mixture, wherein the product mixture comprises 3-pentenenitrile and 2-methyl-3-butenenitrile, and wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the product mixture.
2. The process according to claim 1 , wherein the molar ratio of the zero-valent nickel in the feed to the 1,3-butadiene in the feed is in the range of about 0.00005:1.00 to about 0.0050:1.00.
3. The process according to claim 1 , wherein the temperature is maintained within a range of about 80° C. to about 140° C.
4. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a phosphite.
5. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a phosphonite.
6. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a phosphinite.
7. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a phosphine.
8. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a mixed phosphorus-containing ligand comprising at least one combination selected from the group consisting of a phosphite-phosphonite, a phosphite-phosphinite, a phosphite-phosphine, a phosphonite-phosphinite, a phosphonite-phosphine, and a phosphinite-phosphine or a combination of such members.
9. The process according to claim 1 , wherein the temperature is maintained within the range of about 100° C. to about 130° C.
10. The process according to claim 1 , wherein the molar ratio of the hydrogen cyanide in the feed to the butadiene in the feed is in the range of about 0.92:1.00 to about 0.98:1.00.
11. The process according to claim 1 , wherein the molar ratio of the zero-valent nickel in the feed to the butadiene in the feed is in the range of about 0.0001:1.00 to about 0.0010:1.00.
12. The process according to claim 1 , wherein the residence time in the reaction zone is sufficient to maintain the 2-methyl-3-butenenitrile concentration at or below about 10 weight percent of the total mass of the product mixture.
13. The process according to claim 1 , wherein said feed comprises 2-methyl-3-butenenitrile.
14. The process according to claim 1 , wherein the catalyst precursor composition further comprises at least one monodentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, and a phosphine or a combination of such members.
15. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a bidentate phosphite.
16. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a bidentate phosphonite.
17. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a bidentate phosphinite.
18. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a bidentate phosphine.
19. The process according to claim 1 , wherein the multidentate phosphorus-containing ligand is a bidentate mixed phosphorus-containing ligand selected from the group consisting of a phosphite-phosphonite, a phosphite-phosphinite, a phosphite-phosphine, a phosphonite-phosphinite, a phosphonite-phosphine, and a phosphinite-phosphine or a combination of such members.