Use of diethylenetriamine as a CS2 scavenger in isoprene production

Patent metadata

Field	Value
Publication number	US-9981889-B2
Application number	US-201414913500-A
Country	US
Kind code	B2
Filing date	Aug 15, 2014
Priority date	Aug 22, 2013
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

Methods for scavenging carbon disulfide (“CS 2 ”) from hydrocarbon streams using treatment compositions comprising at least one CS 2 scavenger and at least one phase transfer catalyst therein. The CS 2 scavenger may comprise at least one polyamine with the general formula: H 2 N—(R 1 —NH) x —R 2 —(NH—R 3 ) y —NH 2 wherein R 1 , R 2 , R 3 may be the same or different H, aryl or C 1 -C 4 alkyl; and x and y may be integers from 0 to 10. A hydrocarbon product with a reduced concentration of CS 2 therein.

First claim

The invention claimed is:

1. A method of scavenging carbon disulfide (“CS 2 ”) in a hydrocarbon stream comprising:
(a) contacting said hydrocarbon stream with a treatment composition to form a reaction product of said CS 2 and said treatment composition, wherein said hydrocarbon stream comprises isoprene, wherein said treatment composition comprises at least one CS 2 scavenger and at least one phase transfer catalyst therein and wherein said CS 2 scavenger comprises at least one polyamine with the general formula:
H 2 N—(R 1 —NH) x —R 2 —(NH—R 3 ) y —NH 2

wherein R 1 , R 2 , R 3 may be the same or different H, aryl or C 1 -C 4 alkyl; and x and y are integers from 0 to 10; and
(b) separating the reaction product from said hydrocarbon stream,
wherein said phase transfer catalyst comprises at least one quaternary ammonium salt with the general formula:

wherein R 4 , R 5 , R 6 , and R 7 may be the same or different H, aryl, benzyl, or C 1 -C 20 alkyl, and A − may be a hydroxide, halide, acetate, sulfate, or nitrate anion, and
wherein at least one quaternary ammonium salt is selected from the group consisting of alkyl quaternary ammonium salts, dialkyl fatty ammonium salts, dimethyl dialkyl ammonium salts, and diamide ammonium complexes.

2. The method of claim 1 , wherein said polyamine is diethylenetriamine (“DETA”).

3. The method of claim 1 , wherein at least one quaternary ammonium salt is selected from the group consisting of tetradecyldimethylbenzylammonium chloride (zephiramine) and tetrabutylammonium bromide (“TBAB”).

4. The method of claim 1 , wherein said hydrocarbon stream comprises a solvent stream in an isoprene purification process.

5. The method of claim 4 , wherein said solvent stream is a lean solvent stream that is contacted with said treatment composition as said lean solvent stream exits a stripper in said isoprene purification process.

6. A treatment composition for scavenging carbon disulfide (“CS 2 ”) in a hydrocarbon stream, wherein said hydrocarbon stream comprises isoprene, said treatment composition comprising at least one CS 2 scavenger and at least one phase transfer catalyst therein and wherein said CS 2 scavenger comprises at least one polyamine with the general formula:
H 2 N—(R 1 —NH) x —R 2 —(NH—R 3 ) y —NH 2

wherein R 1 , R 2 , R 3 may be the same or different H, aryl or C 1 -C 4 alkyl; and x and y are integers from 0 to 10.

7. The treatment composition of claim 6 , wherein a weight of the phase transfer catalyst is 0.1 to 10% of a weight of the CS 2 scavenger.

8. The treatment composition of claim 6 , wherein said polyamine is diethylenetriamine (“DETA”).

9. The treatment composition of claim 6 , wherein said phase transfer catalyst comprises at least one quaternary ammonium salt with the general formula:

wherein R 4 , R 5 , R 6 , and R 7 may be the same or different H, aryl, benzyl, or C 1 -C 20 alkyl, and A − may be a hydroxide, halide, acetate, sulfate, or nitrate anion.

10. The treatment composition of claim 9 , wherein at least one quaternary ammonium salt is selected from the group consisting of alkyl quaternary ammonium salts, dialkyl fatty ammonium salts, dimethyl dialkyl ammonium salts, and diamide ammonium complexes.

11. The treatment composition of claim 9 , wherein at least one quaternary ammonium salt is selected from the group consisting of tetradecyldimethylbenzylammonium chloride (zephiramine) and tetrabutylammonium bromide (“TBAB”).

12. A hydrocarbon product with a reduced concentration of carbon disulfide (“CS 2 ”) therein, wherein said CS 2 was reduced in a method comprising:
(a) contacting said hydrocarbon product with a treatment composition to form a reaction product of said CS 2 and said treatment composition, wherein said hydrocarbon product comprises isoprene, wherein said treatment composition comprises at least one CS 2 scavenger and at least one phase transfer catalyst therein and wherein said CS 2 scavenger comprises at least one polyamine with the general formula:
H 2 N—(R 1 —NH) x —R 2 —(NH—R 3 ) y —NH 2

wherein R 1 , R 2 , R 3 may be the same or different H, aryl or C 1 -C 4 alkyl; and x and y are integers from 0 to 10; and
(b) separating the reaction product from said hydrocarbon product,
wherein said phase transfer catalyst comprises at least one quaternary ammonium salt with the general formula:

wherein R 4 , R 5 , R 6 , and R 7 may be the same or different H, aryl, benzyl, or C 1 -C 20 alkyl, and A − may be a hydroxide, halide, acetate, sulfate, or nitrate anion, and
wherein at least one quaternary ammonium salt is selected from the group consisting of alkyl quaternary ammonium salts, dialkyl fatty ammonium salts, dimethyl dialkyl ammonium salts, and diamide ammonium complexes.

13. The hydrocarbon product of claim 12 , wherein said polyamine is diethylenetriamine (“DETA”).

14. The hydrocarbon product of claim 12 , wherein at least one quaternary ammonium salt is selected from the group consisting of tetradecyldimethylbenzylammonium chloride (zephiramine) and tetrabutylammonium bromide (“TBAB”).

Assignees

• Gen Electric

Inventors

• Weissheimer Flavio
• Link John

Classifications

• B01D2255/70

  Non-metallic catalysts, additives or dopants · CPC title

• B01D2256/24

  Hydrocarbons · CPC title

• B01D53/485

  containing only one sulfur compound other than sulfur oxides or hydrogen sulfide · CPC title

• B01D2252/602

  Activators, promoting agents, catalytic agents or enzymes · CPC title

• B01D2252/2053

  Other nitrogen compounds · CPC title