Hydrocarbon conversion processes using lactamium-based ionic liquids

Patent metadata

Field	Value
Publication number	US-9416071-B2
Application number	US-201414556932-A
Country	US
Kind code	B2
Filing date	Dec 1, 2014
Priority date	May 6, 2014
Publication date	Aug 16, 2016
Grant date	Aug 16, 2016

Abstract

A hydrocarbon conversion process is described. The process involves contacting a hydrocarbon feed with a lactamium based ionic liquid catalyst in a reaction zone under reaction conditions to form a mixture comprising reaction products, and the lactamium based ionic liquid catalyst. Typical hydrocarbon conversion processes include alkylation, oligomerization, isomerization, disproportionation, and reverse disproportionation.

First claim

What is claimed is:

1. A hydrocarbon conversion process comprising:
contacting a hydrocarbon feed with a lactamium based ionic liquid catalyst in a hydrocarbon conversion zone under hydrocarbon conversion conditions to form a mixture comprising reaction products, and the lactamium based ionic liquid catalyst.

2. The process of claim 1 wherein the lactamium based ionic liquid catalyst comprises at least one of:
a reaction product of a lactam compound having a general formula

wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8;
and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide;
or
a reaction product of a lactam compound having a general formula

wherein the ring has at least one C≡C double bond, R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8;
and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide;
or
a reaction product of a lactam compound having a general formula

wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8, m is 1 to 8, and the rings can be saturated or unsaturated;
and a Brønsted acid HX; or a Brønsted acid HX where X is a halide, and a metal halide.

3. The process of claim 2 wherein an anion of the Brønsted acid HX is at least one of carboxylates, nitrates, phosphates, phosphinates, phosphonates, imides, cyanates, borates, sulfates, sulfonates, acetates, and halides.

4. The process of claim 2 wherein the ionic liquid has the general formula (III) and wherein at least one ring has at least one C≡C double bond.

5. The process of claim 1 wherein the hydrocarbon conversion process comprises at least one of alkylation, oligomerization, isomerization, disproportionation, and reverse disproportionation.

6. The process of claim 1 wherein the hydrocarbon conversion conditions include at least one of a temperature in a range of about −20° C. to about 250° C., and a pressure in a range of about 0 MPa(g) to about 7.1 MPa(g).

7. The process of claim 1 further comprising separating the reaction products from the lactamium based ionic liquid catalyst.

8. The process of claim 1 further comprising regenerating the lactamium based ionic liquid catalyst.

9. The process of claim 8 further comprising recycling the regenerated lactamium based ionic liquid to the hydrocarbon conversion zone.

10. The process of claim 1 further comprising adding an acid, or an acid precursor to the hydrocarbon conversion zone.

11. The process of claim 1 wherein the hydrocarbon conversion process comprises alkylation, the feed comprises C 2 to C 10 paraffins and olefins, and wherein the hydrocarbon conversion conditions include a catalyst volume in the reactor of from about 1 vol % to about 50 vol %, a temperature of from about 0° C. to about 100° C., a pressure from about 0.3 MPa(g) to about 2.5 MPa(g), an isobutane to olefin molar ratio from about 2 to about 20, and a residence time of about 1 min to about 1 hour.

12. The process of claim 1 wherein the hydrocarbon conversion process comprises oligomerization, the feed comprises C 2 to C 23 olefins, and wherein the hydrocarbon conversion conditions include a temperature of about 50° C. to about 200° C., a pressure of about 0.3 MPa(g) to about 3.4 MPa(g), and a liquid hourly space velocity of about 0.5 to about 8 hr −1 .

13. The process of claim 1 wherein the hydrocarbon conversion process comprises at least one of isomerization, and disproportionation, the feed comprises C 2 to C 23 paraffins, and wherein the hydrocarbon conversion conditions include a temperature of about 0° C. to about 200° C., a pressure of about 0 MPa(g) to about 20.7 MPa(g), and a residence time of less than about 12 hour.

14. The process of claim 1 wherein the hydrocarbon conversion process comprises reverse disproportionation, the feed comprises C 4 to C 25 paraffins, and wherein the hydrocarbon conversion conditions include a temperature of about 0° C. to about 250° C., a pressure of about 0 MPa(g) to about 20.7 MPa(g), and a residence time of less than about 12 hour.

15. A hydrocarbon conversion process comprising:
contacting a hydrocarbon feed with a lactamium based ionic liquid catalyst in a hydrocarbon conversion zone under hydrocarbon conversion conditions to form a mixture comprising conversion reaction products, and the lactamium based ionic liquid catalyst, wherein the hydrocarbon conversion processes comprises at least one of alkylation, oligomerization, isomerization, disproportionation, and reverse disproportionation;
separating the conversion reaction products from the lactamium based ionic liquid catalyst;
recovering the conversion reaction products; and
recycling the lactamium based ionic liquid to the reaction zone;
wherein the lactamium based ionic liquid catalyst comprises at least one of:
a reaction product of a lactam compound having a general formula

wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8;
and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide;
or
a reaction product of a lactam compound having a general formula

wherein the ring has at least one C≡C double bond, R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8;
and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide;
or
a reaction product of a lactam compound having a general formula

wherein R is hydrogen, an alkyl group having from 1 to 12 carbon atoms, an amine, an ether, or a silyl group, n is 1 to 8, m is 1 to 8, and the rings can be saturated or unsaturated;
and a Brønsted acid HX; or a Brønsted acid HX, where X is a halide, and a metal halide.

16. The process of claim 15 wherein an anion of the Brønsted acid HX is at least one of carboxylates, nitrates, phosphates, phosphinates, phosphonates, imides, cyanates, borates, sulfates, sulfonates, acetates, and halides.

17. The process of claim 15 wherein the hydrocarbon conversion conditions include at least one of a temperature in a range of about −20° C. to about 250° C., and a pressure in a range of about 0 MPa(g) to about 20.7 MPa(g).

18. The process of claim 15 further comprising regenerating the lactamium based ionic liquid catalyst before recycling the lactamium based ionic liquid to the reaction zone.

19. The process of claim 15 further comprising adding an acid, or an acid precursor to the reaction zone.

20. The process of claim 15 wherein the hydrocarbon conversion process comprises alkylation,

Assignees

• Uop Llc

Inventors

• Broderick Erin M
• Smith Stuart
• Bhattacharyya Alakananda
• Martins Susie C

Classifications

• C07C2531/14

  of aluminium or boron · CPC title

• C07C2/22

  Metal halides; Complexes thereof with organic compounds · CPC title

• C07C6/10 Primary

  in hydrocarbons containing no six-membered aromatic rings · CPC title

• C07C2/20

  Acids of halogen; Salts thereof {; Complexes thereof with organic compounds} · CPC title

• C07C6/123

  of only one hydrocarbon · CPC title