Hydrochloric acid stripping process for ionic liquid regeneration process

Patent metadata

Field	Value
Publication number	US-9566578-B2
Application number	US-201414567844-A
Country	US
Kind code	B2
Filing date	Dec 11, 2014
Priority date	Dec 11, 2014
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

A method for regenerating deactivated acidic ionic liquid is described. The method involves reducing a level of free hydrochloric acid in the deactivated acidic ionic liquid in a removal zone using at least one of heat, a stripping fluid, reduced pressure, and liquid-liquid extraction to form a deactivated acidic ionic liquid having a reduced level of free hydrochloric acid; and regenerating the deactivated acidic ionic liquid having the reduced level of free hydrochloric acid.

First claim

What is claimed is:

1. A method for regenerating deactivated acidic ionic liquid catalyst from an ionic liquid catalyzed process, comprising the steps of:
(a) withdrawing an effluent comprising hydrocarbon product and deactivated acidic ionic liquid catalyst from a reaction zone;
(b) separating the effluent from step (a) into at least a hydrocarbon phase and an ionic liquid phase comprising at least a portion of the deactivated acidic ionic liquid catalyst;
(c) directing at least a portion of the ionic liquid phase from step (b) to a hydrochloric acid removal zone;
(d) reducing a level of free hydrochloric acid in the ionic liquid phase from step (b) in the hydrochloric acid removal zone using at least one of heat, a stripping fluid, reduced pressure, and liquid-liquid extraction to form a deacidified ionic liquid phase, wherein the deacidified ionic liquid phase has a reduced level of free hydrochloric acid compared to the free hydrochloric acid in the ionic liquid phase of step (b);
(e) directing the deacidified ionic liquid phase from step (d) to an ionic liquid regeneration zone to produce a regenerated ionic liquid catalyst;
(f) returning the regenerated ionic liquid catalyst to the reaction zone.

2. The method of claim 1 wherein the level of free hydrochloric acid is reduced in step (d) using heat, and wherein reducing the level of free hydrochloric acid from the ionic liquid phase comprises:
heating the ionic liquid phase in the hydrochloric acid removal zone; and
withdrawing a stream comprising the removed hydrochloric acid from the hydrochloric acid removal zone.

3. The method of claim 2 wherein the hydrochloric acid removal zone is a stripping column.

4. The method of claim 3 further comprising:
introducing a stripping fluid into the stripping column; and
withdrawing a stream of stripping fluid rich in hydrochloric acid from the stripping column.

5. The method of claim 4 wherein the stripping fluid comprises at least one of nitrogen, carbon dioxide, carbon monoxide, hydrogen, hydrocarbons, and combinations thereof.

6. The method of claim 2 wherein the ionic liquid phase is heated using at least one of steam, a heat transfer fluid, and electricity.

7. The method of claim 1 wherein the level of free hydrochloric acid is reduced in step (d) using reduced pressure, and wherein reducing the level of free hydrochloric acid from the ionic liquid phase comprises:
reducing a pressure in the hydrochloric acid removal zone to a pressure less than a pressure in the separating step (b).

8. The method of claim 1 wherein the level of free hydrochloric acid is reduced in step (d) using the stripping fluid, and wherein reducing the level of free hydrochloric acid from the ionic liquid phase comprises:
introducing the stripping fluid into the hydrochloric acid removal zone; and
withdrawing a stream comprising the stripping fluid comprising the removed hydrochloric acid.

9. The method of claim 8 wherein the stripping fluid comprises nitrogen, carbon dioxide, carbon monoxide, hydrogen, hydrocarbons, or combinations thereof.

10. The method of claim 1 wherein the level of free hydrochloric acid is reduced in step (d) using liquid-liquid extraction, and wherein reducing the level of free hydrochloric acid in the ionic liquid phase comprises:
contacting an extraction solvent stream lean in hydrochloric acid with the ionic liquid phase in the hydrochloric acid removal zone; and further comprising
withdrawing an extraction solvent stream rich in hydrochloric acid from the hydrochloric acid removal zone.

11. The method of claim 10 wherein the extraction solvent stream lean in hydrochloric acid comprises a solvent which is immiscible or partially miscible in the ionic liquid phase and in which the hydrochloric acid is at least partially soluble.

12. The method of claim 10 wherein the extraction solvent stream lean in hydrochloric acid comprises at least one hydrocarbon.

13. The method of claim 1 wherein the deactivated acidic ionic liquid contains conjunct polymer, and wherein regenerating the deacidified ionic liquid phase in step (e) comprises:
contacting the deacidified ionic liquid phase with at least one silane or borane compound, the conjunct polymer reacting with the at least one silane or borane compound resulting in a catalyst phase comprising ionic liquid catalyst and an organic phase containing the conjunct polymer and at least one silyl or boryl compound; and
separating the catalyst phase from the organic phase.

14. The method of claim 1 further comprising:
withdrawing a stream comprising removed hydrochloric acid from the hydrochloric acid removal zone in step (d); and
recovering hydrochloric acid from the stream comprising removed hydrochloric acid.

15. The method of claim 14 further comprising reactivating the regenerated ionic liquid catalyst with the recovered hydrochloric acid.

16. A method for regenerating deactivated acidic ionic liquid catalyst from an ionic liquid catalyzed process, comprising the steps of:
(a) withdrawing an effluent comprising hydrocarbon product and deactivated acidic ionic liquid catalyst from a reaction zone;
(b) separating the effluent from step (a) into at least a hydrocarbon phase and an ionic liquid phase comprising at least a portion of the deactivated acidic ionic liquid catalyst;
(c) directing at least a portion of the ionic liquid phase from step (b) to a hydrochloric acid removal zone;
(d) reducing a level of free hydrochloric acid in the ionic liquid phase from step (b) in the hydrochloric acid removal zone using at least one of heat, a stripping fluid, reduced pressure, and liquid-liquid extraction to form a deacidfied ionic liquid phase, wherein the deacidified ionic liquid phase has a reduced level of free hydrochloric acid compared to the free hydrochloric acid in the ionic liquid phase of step (b);
(e) withdrawing a stream comprising removed hydrochloric acid from the hydrochloric acid removal zone in step (d);
(f) contacting the deacidified ionic liquid phase from step (d) with at least one silane or borane compound, the conjunct polymer reacting with the at least one silane or borane compound resulting in a catalyst phase comprising ionic liquid catalyst and an organic phase containing the conjunct polymer and at least one silyl or boryl compound; and
(g) separating the catalyst phase from the organic phase.

17. The method of claim 16 wherein the level of free hydrochloric acid is reduced in step (d) using heat, and wherein reducing the level of free hydrochloric acid from the ionic liquid phase comprises:
heating the ionic liquid phase in the hydrochloric acid removal zone;
introducing a stripping fluid into the hydrochloric acid removal zone; and
wherein withdrawing the stream comprising the removed hydrochloric acid comprises withdrawing the stripping fluid comprising the removed hydrochloric acid.

18. The method of claim 16 wherein the level of free hydrochloric acid is reduced in step (d) using the stripping fluid, and wherein reducing the level of free hydrochloric acid from the ionic liquid phase comprises:
introducing the stripping fluid into the hydrochloric acid removal zone; and
wherein withdrawing the stream comprising removed hydrochloric acid from the hydrochloric acid removal zone comprises withdrawing a stream of stripping fluid rich in hydrochloric acid from the hydrochloric acid removal zone.

19. The method of claim 16 wherein the level of free hydrochloric acid is reduced in step (d) using liquid-liquid extraction,

Assignees

• Uop Llc

Inventors

• Brendel Michael
• Buchbinder Avram M
• Olson Paul
• Martins Susie C
• Desalvo Kaitlin M
• Nafis Douglas A

Classifications

• B01J31/0298 Primary

  the ionic liquids being characterised by the counter-anions · CPC title

• B01J31/4069 Primary

  involving extraction with coordinating ionic liquids or supercritical fluids, e.g. CO2 · CPC title

• B01J2531/008

  Methods or theories · CPC title

• C07F9/025

  Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds (of natural phosphatides C07F9/103; phosphines C07F9/5095) · CPC title

• B01J2231/44

  Allylic alkylation, amination, alkoxylation or analogues · CPC title