Method of producing alkylaromatic compounds using aromatic compound from catalyst regeneration

Patent metadata

Field	Value
Publication number	US-9732014-B2
Application number	US-201414200693-A
Country	US
Kind code	B2
Filing date	Mar 7, 2014
Priority date	Mar 7, 2014
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

A process for producing alkylaromatic compounds is described. The process involves utilizing at least a portion of the aromatic compound used to regenerate the alkylation catalyst in a spent alkylation reaction zone as a reactant in the active alkylation reaction zone.

First claim

What is claimed is:

1. A process for producing alkylaromatic compounds comprising:
contacting an aromatic compound and an olefin in an alkylation reaction zone under alkylation conditions in the presence of an alkylation catalyst to produce an alkylation product containing monoalkylaromatic compounds, dialkylaromatic compounds, and unreacted aromatic compound;
separating the alkylation product in a separation zone into an unreacted aromatic fraction and a fraction containing the monoalkylaromatic compounds and the dialkylaromatic compounds;
regenerating a spent alkylation reaction zone by passing an aromatic compound stream through the spent alkylation zone at a regeneration temperature above an alkylation temperature to provide a regeneration aromatic compound stream; and
introducing at least about 80 wt % of the regeneration aromatic compound stream directly into the alkylation zone, the regeneration aromatic compound stream being at the alkylation temperature.

2. The process of claim 1 wherein regenerating a spent alkylation reaction zone comprises heating the spent alkylation zone from the alkylation temperature to the regeneration temperature, maintaining the spent alkylation zone at the regeneration temperature for a period of time, and cooling the spent alkylation zone from the regeneration temperature to the alkylation temperature.

3. The process of claim 2 wherein heating the spent alkylation zone from the alkylation temperature to the regeneration temperature takes about 8 hr, wherein the spent alkylation zone is maintained at the regeneration temperature for about 8 hr, and wherein cooling the spent alkylation zone from the regeneration temperature to the alkylation temperature takes about 8 hr.

4. The process of claim 1 wherein at least about 50 wt % of the regeneration aromatic compound stream is introduced into the alkylation zone.

5. The process of claim 1 further comprising:
separating the fraction containing the monoalkylaromatic compounds and the dialkylaromatic compounds into a monoalkylaromatic compound stream and a dialkylaromatic compound stream;
introducing the dialkylaromatic compound stream and a second aromatic compound into a transalkylation reaction zone under transalkylation conditions to produce a transalkylation product containing monoalkylaromatics, unreacted dialkylaromatics, and unreacted second aromatic compound;
introducing a second portion of the regeneration aromatic compound stream into the transalkylation reaction zone as at least a portion of the second aromatic compound.

6. The process of claim 5 wherein the second portion of the regeneration aromatic compound stream comprises at least about 50 wt % of a remainder of the regeneration aromatic compound stream, the remainder of the regeneration aromatic compound stream being the regeneration aromatic compound stream minus the portion introduced into the alkylation zone.

7. The process of claim 1 further comprising introducing a third portion of the regeneration aromatic compound stream into the separation zone.

8. The process of claim 1 wherein the alkylation temperature is in a range of about 120° C. to about 150° C., and the regeneration temperature is in a range of about 160° C. to about 250° C.

9. The process of claim 1 wherein the alkylation temperature is in a range of about 130° C. to about 140° C., and the regeneration temperature is in a range of about 180° C. to about 250° C.

10. The process of claim 1 wherein regenerating the spent alkylation reaction zone takes place at a pressure in a range of 1.300 MPa(g) to about 7.000 MPa(g).

11. The process of claim 1 wherein the alkylation catalyst is selected from mordenite, ZSM-4, ZSM-12, ZSM-20, ZSM-38, offretite, gmelinite, beta, NU-87, UZM-8, MCM-22, MCM-36, MCM-49, zeolite Y, zeolite X, gottardite, MOR, MWW, FAU, RE-Y, NES, ZDA-2, DA-114, or combinations thereof.

12. A process for producing alkylaromatic compounds comprising:
contacting an aromatic compound and an olefin in an alkylation reaction zone under alkylation conditions in the presence of an alkylation catalyst to produce an alkylation product containing monoalkylaromatic compounds, dialkylaromatic compounds, and unreacted aromatic compound;
separating the alkylation product in a separation zone into an unreacted aromatic fraction and a fraction containing the monoalkylaromatic compounds and the dialkylaromatic compounds;
regenerating a spent alkylation reaction zone by passing an aromatic compound stream through the spent alkylation zone while heating the spent alkylation zone from an alkylation temperature to a regeneration temperature, maintaining the spent alkylation zone at the regeneration temperature for a period of time, and cooling the spent alkylation zone from the regeneration temperature to the alkylation temperature to provide a regeneration aromatic compound stream;
introducing at least about 80 wt % of the regeneration aromatic compound stream directly into the alkylation zone, the regeneration aromatic compound stream being at the alkylation temperature.

13. The process of claim 12 wherein heating the spent alkylation zone from the alkylation temperature to the regeneration temperature takes about 8 hr, wherein the spent alkylation zone is maintained at the regeneration temperature for about 8 hr, and wherein cooling the spent alkylation zone from the regeneration temperature to the alkylation temperature takes about 8 hr.

14. The process of claim 12 wherein at least about 50 wt % of the regeneration aromatic compound stream is introduced into the alkylation zone.

15. The process of claim 12 further comprising:
separating the fraction containing the monoalkylaromatic compounds and the dialkylaromatic compounds into a monoalkylaromatic compound stream and a dialkylaromatic compound stream;
introducing the dialkylaromatic compound stream and a second aromatic compound into a transalkylation reaction zone under transalkylation conditions to produce a transalkylation product containing monoalkylaromatics, unreacted dialkylaromatics, and unreacted second aromatic compound;
introducing a second portion of the regeneration aromatic compound stream into the transalkylation reaction zone as at least a portion of the second aromatic compound.

16. The process of claim 15 wherein the second portion of the regeneration aromatic compound stream comprises at least about 50 wt % of a remainder of the regeneration aromatic compound stream, the remainder of the regeneration aromatic compound stream being the regeneration aromatic compound stream minus the portion introduced into the alkylation zone.

17. The process of claim 12 further comprising introducing a third portion of the regeneration aromatic compound stream into the separation zone.

18. The process of claim 12 wherein the alkylation temperature is in a range of about 120° C. to about 150° C., and the regeneration temperature is in a range of about 160° C. to about 250° C.

19. The process of claim 12 wherein regenerating a spent alkylation reaction zone takes place at a pressure in a range of 2.758 MPa to about 4.137 MPa.

20. The process of claim 12 wherein the alkylation catalyst is selected from mordenite, ZSM-4, ZSM-12, ZSM-20, ZSM-38, offretite, gmelinite, beta, NU-87, UZM-8, MCM-22, MCM-36, MCM-49, zeolite Y, zeolite X, gottardite, MOR, MWW, FAU, RE-Y, NES, ZDA-2, DA-114, or combinations thereof.

Assignees

• Uop Llc

Inventors

• Sohn Stephen W
• Zhang Shuguang
• Jani Priyesh Jayendrakumar
• Banerjee Soumendra M

Classifications

• C07C6/126

  of more than one hydrocarbon · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title

• C07C2/66 Primary

  Catalytic processes · CPC title

• C07C5/2775

  with crystalline alumino-silicates, e.g. molecular sieves · CPC title

• C07C15/107

  having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates · CPC title