# US 9,040,735 B2 · Process for making nitriles > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,735 B2 - Document ID: US9040735B2 - Status: Granted - Kind: B2 - Application number: 14/346,882 - Filed: 2012-10-04 - Published: 2014-08-21 - Granted: 2015-05-26 - Earliest claimed: 2011-10-07 - Assignees: Invista North America S.A.R.L. - Applicants: Invista North America S.A.R.L. - Inventors: Sudhir Aki; Wyatte E. Allen; Mark Anstrom; Charles Nelson Campbell, II; Tseng Chao; James E. McIntosh; Larry E. Moerbe; Bruce Edwin Murphree; Mark D. Rogers; William J. Tenn, III; Thomas E. Vos; Michael W. Wensing - Web page: https://patentgrep.com/patent/US9040735B2 ## CPC - C07C 253/18: by reaction of ammonia or amines with compounds containing carbon-to-carbon multiple bonds other than in six-membered aromatic rings - C07C 253/10: to compounds containing carbon-to-carbon double bonds - Y02P 20/584: Recycling of catalysts - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The present invention relates to a process for hydrocyanating 3-pentenenitrile. The process can include feeding 3-pentenenitrile and HCN to a hydrocyanation reaction zone that includes a Lewis acid promoter, nickel, and a phosphorus-containing ligand. In various embodiments, the process can also include controlling water concentration within the hydrocyanation reaction zone sufficient to maintain a high activity of the ligand catalyst complex while recycling at least a portion of the ligand catalyst complex. ## Claims ### Claim 1 A process for hydrocyanating 3-pentenenitrile in a reaction zone in the presence of a catalyst complex comprising a phosphorus-containing ligand and nickel metal, said process comprising: a. charging the catalyst complex, 3-pentenenitrile, a Lewis acid and HCN to the reaction zone; b. withdrawing reactor effluent comprising hydrocyanation product and catalyst complex from the reaction zone; c. contacting the reactor effluent with an extraction solvent to recover catalyst complex and remove impurities from the catalyst complex; and d. recharging at least a portion of the recovered catalyst complex to the reaction zone, e. establishing disproportionation and hydrolysis deactivation percentages of the catalyst complex for the particular process, and f. controlling the amount of water in the catalyst complex recharged to the reaction zone in step d. to decrease the total percentage deactivation percentages established in step e. ### Claim 2 (depends on 1) The process of claim 1, wherein the controlling of the amount of water in step f. is by adding water. ### Claim 3 (depends on 1) The process of claim 1, wherein the controlling of the amount of water in step f. is by removing water. ### Claim 4 A process for hydrocyanating 3-pentenenitrile in a reaction zone in the presence of a catalyst complex comprising a phosphorus-containing ligand and nickel metal, said process comprising: a. charging the catalyst complex, 3-pentenenitrile, a Lewis acid and HCN to the reaction zone; b. withdrawing reactor effluent comprising hydrocyanation product and catalyst complex from the reaction zone; c. contacting the reactor effluent with an extraction solvent to recover catalyst complex and remove impurities from the catalyst complex; and d. recharging at least a portion of the recovered catalyst complex to the reaction zone, wherein the amount of water in the catalyst complex recharged to the reaction zone in step d. is controlled to decrease the deactivation of the catalyst complex to less than about 5% compared to the process without said control. ### Claim 5 (depends on 4) The process of claim 4, wherein the amount of water is controlled by adding water. ### Claim 6 (depends on 4) The process of claim 4, wherein the amount of water is controlled by removing water. ### Claim 7 (depends on 4) The process of claim 4, wherein the phosphorus-containing ligand is a phosphorus-containing ligand of Structure I, wherein in Structure I, R1 and R2 are the same or different, substituted or unsubstituted, monovalent aryl groups; R1 and R2 are bridged to one another or unbridged to one another; X is independently selected from the group consisting of hydrogen, alkyl, aryl, heteroaryl, aryloxy, heteroaryloxy, alkyloxy, alkoxyalkyl, acetal, carboaryloxy, carboalkoxy, arylcarbonyl, alkylcarbonyl, phosphitylbisaryl, phosphitylbisheteroaryl, hydroxybisaryl, hydroxybisheteroaryl, oxazole, amine, amide, nitrile, mercaptyl, and halogen groups. ### Claim 8 (depends on 7) The process of claim 7, wherein the phosphorus-containing ligand is a bidentate phosphorus-containing ligand having aromatic termini that are connected through a phosphorus-containing backbone linkage. ### Claim 9 (depends on 7) The process of claim 7, wherein the phosphorus-containing ligand is a bidentate phosphorus-containing ligand of Structure II, wherein in Structure II, O-Q-O is a divalent species of a bisaryl compound selected from the group consisting of Structure III, IV, or V, wherein in Structures II-V, R1 and R2 are the same or different, substituted or unsubstituted, monovalent aryl groups; and each of R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 is independently selected from the group consisting of hydrogen, alkyl, aryl, heteroaryl, aryloxy, heteroaryloxy, alkyloxy, alkoxyalkyl, acetal, carboaryloxy, carboalkoxy, arylcarbonyl, alkylcarbonyl, oxazole, amine, amide, nitrile, mercaptyl, and halogen groups. ### Claim 10 (depends on 7) The process of claim 7, wherein the phosphorus-containing ligand is a bidentate phosphorus-containing ligand of Structure VI, wherein R1 and R2 are the same or different, substituted or unsubstituted, monovalent aryl groups; each of R3, R4, R5, R6 is independently selected from the group consisting of hydrogen and C1-10 alkyl. ### Claim 11 (depends on 7) The process of claim 7, wherein the phosphorus-containing ligand is a bidentate phosphorus-containing ligand of Structure VII, ### Claim 12 (depends on 1) The process of claim 1, wherein the Lewis acid comprises zinc chloride or triphenylboron. ### Claim 13 (depends on 1) The process of claim 1, wherein processing downstream of the hydrocyanation reaction zone comprises a liquid-liquid extraction of the phosphorus-containing ligand from a dinitrile derived from the 3-pentenenitrile using a hydrocarbon extraction solvent. ### Claim 14 (depends on 1) The process of claim 1 wherein processing downstream of the hydrocyanation reaction zone comprises distillation. ### Claim 15 (depends on 1) The process of claim 1, wherein the amount of water is controlled so that the concentration of water in the reaction zone is about 100 ppm to about 300 ppm.