Extraction solvent control for reducing stable emulsions

Patent metadata

Field	Value
Publication number	US-9388204-B2
Application number	US-201214367156-A
Country	US
Kind code	B2
Filing date	Nov 20, 2012
Priority date	Dec 21, 2011
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the diphosphite-containing compounds.

First claim

What is claimed is:

1. A process for recovering diphosphite-containing compounds from a feed mixture comprising diphosphite-containing compounds, organic mononitriles and organic dinitriles in a multistage countercurrent liquid-liquid extractor with extraction solvent comprising aliphatic hydrocarbon, cycloaliphatic hydrocarbon or a mixture of aliphatic and cycloaliphatic hydrocarbon, said process comprising:
a) flowing the feed mixture to the first stage of the multistage countercurrent liquid-liquid extractor; and
b) contacting the feed mixture with extraction solvent in the multistage countercurrent liquid-liquid extractor,
wherein the first stage of the multistage countercurrent liquid-liquid extractor comprises a mixing section and a settling section, wherein a light phase separates from a heavy phase in the settling section, wherein the light phase comprises extraction solvent and extracted diphosphite-containing compounds, wherein the heavy phase comprises organic mononitriles and organic dinitriles, wherein a first portion of the light phase is withdrawn from the settling section and treated to recover diphosphite-containing compounds extracted into the light phase, and wherein a second portion of the light phase is withdrawn from the settling section and recycled to the mixing section of the first stage of the multistage countercurrent liquid-liquid extractor.

2. The process of claim 1 , wherein the recycle of the light phase to the mixing section of the first stage of the multistage countercurrent liquid-liquid extractor is sufficient to result in enhanced settling of the light phase and heavy phase in the settling section of the first stage.

3. The process of claim 1 , wherein the recycle of the light phase in the settling section of the first stage of the multistage countercurrent liquid-liquid extractor is sufficient to achieve at least one of the following results: (a) a reduction in the size of an emulsion phase in the settling section, based upon the size of the emulsion phase in the absence of recycle of the heavy phase; (b) an increase in the rate of settling in the settling section, based upon the rate of settling in the absence of recycle of the heavy phase; (c) an increase in the amount of diphosphite-containing compounds in the light phase, based upon the upon the amount of diphosphite-containing compounds in the light phase in the absence of recycle of the heavy phase; (d) a reduction in the size of a rag layer in the settling section, based upon the size of a rag layer in the settling section in the absence of recycle of the heavy phase; and (e) reduction in the rate of formation of a rag layer in the settling section, based upon the rate of formation of a rag layer in the settling section in the absence of recycle of the light phase.

4. The process of claim 1 , wherein the recycle of the light phase in the settling section of the first stage is sufficient to result in improved extraction of diphosphite-containing compounds based upon the extraction of diphosphite compounds in the absence of recycle of the light phase.

5. The process of claim 1 , wherein the extraction solvent recycle ratio (ESRR) is between 0.1 and 0.9, wherein ESRR is defined by the ratio of X to Y, wherein X is the mass per unit time of the second portion of the light phase recycled to the mixing section of the first stage of the multistage countercurrent liquid-liquid extractor, and wherein Y is the mass per unit time of all extraction solvent charged to the mixing section of the first stage of the multistage countercurrent liquid-liquid extractor.

6. The process of claim 1 , wherein the ESRR is between 0.2 and 0.8.

7. A process according to claim 1 wherein the diphosphite-containing compound is a Ni complex with a diphosphite ligand selected from the group consisting of:

wherein in I, II and Ill, R 1 is phenyl, unsubstituted or substituted with one or more C 1 to C 12 alkyl or C 1 to C 12 alkoxy groups; or naphthyl, unsubstituted or substituted with one or more C 1 to C 12 alkyl or C 1 to C 12 alkoxy groups; and wherein Z and Z 1 are independently selected from the group consisting of structural formulae IV, V, VI, VII, and VIII:

and wherein
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, C 1 to C 12 alkyl, and C 1 to C 12 alkoxy;
X is O, S, or CH(R 10 );
R 10 is H or C 1 to C 12 alkyl;

and wherein
R 11 and R 12 are independently selected from the group consisting of H, C 1 to C 12 alkyl, and C 1 to C 12 alkoxy and CO 2 R 13 ,
R 13 is C 1 to C 12 alkyl, or C 6 to C 10 aryl unsubstituted or substituted with C 1 to C 4 alkyl;
Y is O, S, or CH(R 14 );
R 14 is H or C 1 to C 12 alkyl;

wherein
R 15 is selected from the group consisting of H, C 1 to C 12 alkyl, and C 1 to C 12 alkoxy and CO 2 R 16 ,
R 16 is C 1 to C 12 alkyl, or C 6 to C 10 aryl, unsubstituted or substituted with C 1 to C 4 alkyl,

and wherein
for structural formulae I through VIII, the C 1 to C 12 alkyl, and C 1 to C 12 alkoxy groups may be straight chain or branched.

8. The process of claim 1 wherein at least one stage of the extraction is carried out above 40° C.

9. The process of claim 1 , wherein at least one stage contains a Lewis base.

10. The process of claim 9 wherein the Lewis base is a monodentate triarylphosphite wherein the aryl groups are unsubstituted or substituted with alkyl groups having 1 to 12 carbon atoms, and wherein the aryl groups may be interconnected.

11. The process of claim 9 wherein the Lewis base is selected from the group consisting of:
a) anhydrous ammonia, pyridine, alkylamine, dialkylamine, trialkylamine wherein the alkyl groups have 1 to 12 carbon atoms; and
b) polyamine.

12. The process of claim 11 wherein the polyamine comprises at least one selected from hexamethylene diamine and dimers and trimers of hexamethylene diamine.

13. The process of claim 11 wherein the polyamine comprises dimers of hexamethylene diamine.

14. The process of claim 9 wherein the Lewis base compound is Amberlyst 21® resin.

15. The process of claim 1 wherein the extraction solvent is cyclohexane.

16. The process of claim 1 wherein at least a portion of the process is carried out in an extraction column or a mixer-settler.

17. The process of claim 1 wherein the feed mixture is an effluent stream from a hydrocyanation process.

18. The process of claim 14 wherein the hydrocyanation process includes a 3-pentenenitrile hydrocyanation process.

19. The process of claim 15 wherein the hydrocyanation process includes a 1,3-butadiene hydrocyanation process.

20. The process of claim 1 wherein the feed mixture is an effluent stream from a hydrocyanation process and the concentration of pentenenitriles in the feed to the mixing section of the first stage of the multistage countercurrent liquid-liquid extractor, is sufficient to result in enhanced settling of the light phase and heavy phase in the settling section of the first stage, and a reduction in stable emulsion and rag.

Assignees

• Invista North America Sarl
• Invista North America Sarl

Inventors

• Tenn Iii William J
• Aki Sudhir N V K
• Vos Thomas E
• Chao Tseng H

Classifications

• B01D11/0426

  Counter-current multistage extraction towers in a vertical or sloping position · CPC title

• B01J31/4053

  with recovery of phosphorous catalyst system constituents · CPC title

• B01J31/185

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

• C07F9/141

  Esters of phosphorous acids · CPC title

• B01D11/0457

  comprising rotating mechanisms, e.g. mixers, mixing pumps · CPC title