Process for producing alkylated aromatic hydrocarbons from a mixed hydrocarbon feedstream

Patent metadata

Field	Value
Publication number	US-10654767-B2
Application number	US-201515321352-A
Country	US
Kind code	B2
Filing date	Jun 25, 2015
Priority date	Jun 26, 2014
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

The present invention relates to a process for producing alkylated aromatic hydrocarbons such as ethyl benzene or cumene from a mixed hydrocarbon feedstream comprising subjecting C6 cut separated from said mixed hydrocarbon feedstream to hydrocracking to provide benzene and subjecting said benzene to alkylation.

First claim

The invention claimed is:

1. A process for producing alkylated aromatic hydrocarbons comprising:
(a) subjecting a mixed hydrocarbon feedstream to a separation to provide a C6 cut;
(b) subjecting the C6 cut to hydrocracking, wherein the hydrocracking comprises contacting the C6 cut with a hydrocracking catalyst comprising a hydrogenation metal and a zeolite under hydrocracking conditions comprising a temperature of 450-580° C., a pressure of 300-5000 kPa gauge, and a Weight Hourly Space Velocity of 0.1-20 h 1 to provide a benzene stream, wherein the benzene stream has a benzene purity of at least 98 wt %; and
(c) subjecting the benzene stream to alkylation to provide a product stream rich in alkylated aromatic hydrocarbons.

2. The process according claim 1 , wherein step (b) further comprises separating the benzene stream by vapor-liquid separation.

3. The process according to claim 1 , wherein the hydrocracking catalyst comprises 0.1-1 wt-% of the hydrogenation metal in relation to the total catalyst weight and the zeolite has a pore size of 5-8 Å and a silica (SiO 2 ) to alumina (Al 2 O 3 ) molar ratio of 5-200.

4. The process according to claim 3 , wherein the benzene stream comprises less than 1 wt % co-boilers of benzene.

5. The process according to claim 1 , wherein the hydrocracking produces a benzene stream comprises less than 1 wt % co-boilers of benzene.

6. The process according to claim 1 , wherein the alkylation comprises contacting the benzene stream in the presence of ethylene with an alkylation catalyst under alkylation conditions to produce ethylbenzene, wherein said alkylation catalyst comprises beta zeolite, zeolite Y, ZSM-12, MCM-22 or mordenite and wherein said alkylation conditions comprise a temperature of 120-250° C., a pressure of 1000-5000 kPa, a Weight Hourly Space Velocity (WHSV) of 0.5-20 h −1 , and a benzene/ethylene molar ratio of 3-10.

7. The process according to claim 6 , wherein the temperature is 150-230° C., the Weight Hourly Space Velocity is 1-10 h −1 , and the benzene/ethylene molar ratio is 5-8.

8. The process according to claim 1 , wherein the alkylation comprises contacting the benzene stream in the presence of propylene with an alkylation catalyst under alkylation conditions to produce cumene, wherein said alkylation catalyst comprises a zeolite selected from the group consisting of beta zeolite, zeolite Y, ZSM-12, MCM-22 and mordenite and wherein said alkylation conditions comprise a temperature of 120-250° C., a pressure of 1000-5000 kPa, a Weight Hourly Space Velocity (WHSV) of 0.5-20 and a benzene/propylene molar ratio of 3-10.

9. The process according to claim 8 , wherein the temperature is 150-230° C., the Weight Hourly Space Velocity is 1-10 h −1 , and the benzene/propylene molar ratio is 5-8.

10. The process according to claim 1 , wherein the stream rich in alkylated aromatic hydrocarbons is subjected to a separation to provide a monoalkylated aromatic product stream and a stream comprising polyalkylated aromatic product and wherein said polyalkylated aromatic product is recycled to the hydrocracking.

11. The process according to claim 1 , wherein the mixed hydrocarbon feedstream comprises reformate.

12. The process according to claim 1 , the benzene stream has a benzene purity of greater than 99 wt %.

13. The process according to claim 1 , wherein the hydrocracking further produces a C2-3 alkane stream that is subjected to olefins synthesis to provide a C2-3 alkene stream that is subjected to the alkylation as alkylation agent.

14. The process according to claim 13 , wherein the C2-3 alkane stream comprises ethane and the olefins synthesis is ethane cracking to provide ethylene.

15. The process according to claim 13 , wherein the C2-3 alkane stream comprises propane and the olefins synthesis is propane dehydrogenation to provide propylene.

16. The process according to claim 15 , wherein the dehydrogenation comprises contacting the propane with a dehydrogenation catalyst under dehydrogenation conditions to produce propylene.

17. The process according to claim 16 , wherein the dehydrogenation catalyst comprises a catalyst support comprising 0.1-1 wt-% hydrogenation metal in relation to the total catalyst weight.

18. The process according to claim 16 , wherein the dehydrogenation conditions comprise a temperature of 450-800° C. and a pressure of ambient to 1000 kPa gauge.

19. The process according to claim 18 , wherein the temperature is 540-700° C. and the pressure is 25-500 kPa gauge.

Assignees

• Sabic Global Technologies Bv

Inventors

• Daniëls Dimitri
• Wong Kae Shin

Classifications

• C07C4/06

  Catalytic processes {(C07C4/025 takes precedence)} · CPC title

• C07C2/66 Primary

  Catalytic processes · CPC title

• C10G47/16

  Crystalline alumino-silicate carriers · CPC title

• C10G69/123

  alkylation · CPC title

• C07C2523/42

  Platinum · CPC title