Separating a solvent from a nickel catalyst by distillation

Patent metadata

Field	Value
Publication number	US-10759741-B2
Application number	US-201414904726-A
Country	US
Kind code	B2
Filing date	Jul 16, 2014
Priority date	Jul 17, 2013
Publication date	Sep 1, 2020
Grant date	Sep 1, 2020

Abstract

A solvent is at least partially separated from a catalyst. The catalyst comprises nickel and a bidentate phosphorus-containing ligand. The method for separation involves distilling a catalyst solution. The ratio of 2-pentenenitrile to 3-pentenenitrile in distillation column bottoms is controlled to reduce the amount of 3-pentenenitrile which is isomerized to form 2-methyl-3-butenenitrile. Isomerization of 3-pentenenitrile to 2-methyl-3-butenenitrile and subsequent isomerization of 2-methyl-3-butenenitrile to 2-methyl-2-butenenitrile, and/or hydrocyanation of 2-methyl-3-butenenitrile to methylglutaronitrile represents a loss in adiponitrile yield in a process for making adiponitrile.

First claim

What is claimed is:

1. A method for evaporation of solvent from a catalyst solution comprising solvent and a catalyst, wherein said solvent comprises 2-pentenenitrile (2PN) and 3-pentenenitrile (3PN), wherein said catalyst comprises nickel and a bidentate phosphorus-containing ligand, and wherein said method comprises the steps of:
(a) introducing said catalyst solution into a distillation zone; and
(b) evaporating solvent in the distillation zone to form a solvent-depleted catalyst solution comprising said catalyst, 2-pentenenitrile and 3-pentenenitrile, while maintaining the 3PN/2PN ratio in said solvent-depleted catalyst solution at 14/1 or less, wherein said catalyst solution, which is introduced into the distillation zone of step (a), is an extracted catalyst solution formed by extracting catalyst from an effluent stream or distilled bottoms fraction of an effluent stream, wherein said effluent stream is the effluent stream from a reactor, and wherein said reactor is selected from the group consisting of (i) a reactor for reacting hydrogen cyanide with 1,3-butadiene in the presence of the catalyst to form 3-pentenenitrile, (ii) a reactor for isomerizing 2-methyl-3-butenenitrile in the presence of the catalyst to form 3-pentenenitrile, and (iii) a reactor for reacting 3-pentenenitrile with hydrogen cyanide in the presence of the catalyst to form adiponitrile, wherein the effluent stream or distilled fraction of the effluent stream is contacted with an extraction solvent comprising one or more linear aliphatic hydrocarbons, one or more branched aliphatic hydrocarbons, one or more unsubstituted cycloaliphatic hydrocarbons, one or more alkyl-substituted cycloaliphatic hydrocarbons, and/or one or more aromatic hydrocarbons, wherein an extraction solvent is a solvent evaporated from said catalyst solution in step (b).

2. The method of claim 1 , wherein said catalyst solution, which is introduced into the distillation zone of step (a), is an effluent stream from a reactor for reacting 3-pentenenitrile with hydrogen cyanide in the presence of the catalyst to form adiponitrile, and wherein unreacted 3-pentenenitrile is a solvent evaporated from said catalyst in step (b).

3. The method of claim 2 , wherein a temperature of the solvent-depleted catalyst solution is controlled between 60° C. and 160° C. during the evaporating of step (b).

4. The method of claim 2 , wherein the ratio of step (b) is maintained by controlling the composition of 3-pentenenitrile and 2-pentenenitrile in the catalyst solution introduced in step (a).

5. The method of claim 2 , wherein the catalyst further comprises at least one monodentate phosphorus containing ligand selected from the group consisting of monodentate phosphite, monodentate phosphonite, monodentate phosphinite, and monodentate phosphine.

6. A method for reacting 3-pentenenitrile (3PN) with hydrogen cyanide in the presence of a catalyst to form adiponitrile, wherein said catalyst comprises nickel and a bidentate phosphorus-containing ligand, and said method comprises the steps of:
(a) obtaining a reaction effluent stream comprising adiponitrile, unreacted 3PN, 2-pentenenitrile (2PN) and catalyst;
(b) extracting the reaction effluent stream from step (a) with an extraction solvent to obtain an extracted catalyst solution comprising 3PN, 2PN, catalyst and extraction solvent;
(c) introducing the extracted catalyst solution from step (b) into a distillation zone;
(d) evaporating solvent from said catalyst in the distillation zone of step (c) to form a solvent-depleted catalyst solution comprising the catalyst, 2-pentenenitrile, and the 3-pentenenitrile while maintaining the 3PN/2PN ratio in said solvent-depleted catalyst solution at 14/1 or less; and
(e) contacting the solvent-depleted catalyst solution from step (d) with hydrogen cyanide and Lewis acid to form the adiponitrile.

7. The method of claim 2 , wherein the 3PN/2PN ratio in said solvent-depleted catalyst solution is maintained at from 1/1 to 7/1.

8. The method of claim 6 , wherein the 3PN/2PN ratio in said solvent-depleted catalyst solution is maintained at from 1/1 to 7/1.

9. The method of claim 2 , wherein the solvent of step (b) comprises one or more linear aliphatic hydrocarbons, one or more branched aliphatic hydrocarbons, one or more unsubstituted cycloaliphatic hydrocarbons, one or more alkyl-substituted cycloaliphatic hydrocarbons, and/or one or more aromatic hydrocarbons, and wherein the 3PN/2PN ratio in said solvent-depleted catalyst solution is maintained at from 1/1 to 3/1.

10. The method of claim 2 , wherein solvent is evaporated in the distillation zone utilizing a distillation method selected from the group consisting of an adiabatic flash, a distillation at or above one atmosphere pressure, and a vacuum distillation.

Assignees

• Invista North America Sarl

Inventors

• Aki Sudhir N V K
• Garner James M
• Tenn Iii William J
• Vos Thomas E

Classifications

• C07C253/34

  Separation; Purification · CPC title

• C07C253/10 Primary

  to compounds containing carbon-to-carbon double bonds · CPC title

• B01J31/185

  Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof · CPC title

• B01J38/02

  Heat treatment · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title