Alkylation process

Patent metadata

Field	Value
Publication number	US-9249067-B2
Application number	US-201113642676-A
Country	US
Kind code	B2
Filing date	Apr 15, 2011
Priority date	May 20, 2010
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

The present invention provides an improved process for producing an alkylated aromatic compound from an at least partially untreated alkylatable aromatic compound having catalyst poisons and an alkylating agent, wherein said alkylatable aromatic compound stream is treated to reduce catalyst poisons with a treatment composition having a surface area/surface volume ratio of greater than or equal to 30 in −1 (12 cm −1 ) in a treatment zone separate from an alkylation reaction zone under treatment conditions including a temperature of from about 30° C. to about 300° C. to form an effluent comprising said treated alkylatable aromatic compound.

First claim

We claim:

1. A process for producing an alkylated aromatic compound stream from at least one partially untreated alkylatable aromatic compound stream having catalyst poisons comprising a compound having nitrogen as an element, the process comprising the steps of:
(a) feeding said untreated alkylatable aromatic compound stream having said catalyst poisons and a portion of an alkylating agent stream in the liquid phase to a treatment zone having a treatment composition comprising a zeolite having a *BEA framework type;
(b) contacting said untreated alkylatable aromatic compound stream and said alkylating agent stream with said treatment composition in said treatment zone separate from an alkylation reaction zone under liquid phase treatment conditions to remove at least a portion of said catalyst poisons and to alkylate at least a portion of said alkylatable aromatic compound to form a treated effluent stream which comprises treated alkylatable aromatic compound, an alkylated aromatic compound and a reduced amount of catalyst poisons, wherein said treatment composition has a surface area/surface volume ratio in the range of 180 in −1 (71 cm −1 ) to 220 in −1 (87 cm −1 ), said liquid phase treatment conditions include a temperature of from about 30° C. to about 300° C. and a pressure from about 101 kPa to about 4601 kPa, and a molar ratio of untreated alkylatable aromatic compound to alkylating agent of greater than or equal to about 50:1; and
(c) contacting said treated alkylatable aromatic compound in said effluent stream and an additional portion of said alkylating agent stream with a catalyst composition in said alkylation reaction zone separate from said treatment zone under at least partial liquid phase catalytic conversion conditions to form an alkylated effluent stream which comprises additional alkylated aromatic compound, wherein said catalyst composition comprises a porous crystalline material having a framework structure type selected from the group consisting of FAU, *BEA, MOR, MWW and mixtures thereof, wherein said at least partial liquid phase catalytic conversion conditions include a temperature of from about 100° C. to about 300° C., a pressure from about 689 kPa to about 4601 kPa, a molar ratio of treated alkylatable aromatic compound to alkylating agent of from about 0.01:1 to about 25:1, and a feed weight hourly space velocity (WHSV) based on alkylating agent of from about 0.5 to about 500 hr −1 .

2. The process of claim 1 , wherein said treatment composition is zeolite beta.

3. The process of claim 1 , wherein said porous crystalline material having said FAU framework structure type is faujasite, zeolite Y, Ultrastable Y (USY), Dealuminized Y (Deal Y), Rare Earth Y (REY), Ultrahydrophobic Y (UHP-Y) or a mixture thereof.

4. The process of claim 1 , wherein said porous crystalline material having said *BEA framework structure type is zeolite beta.

5. The process of claim 1 , wherein said porous crystalline material having said MOR framework structure type is mordenite, TEA-mordenite or a mixture thereof.

6. The process of claim 1 , wherein said porous crystalline material having said MWW framework structure type has an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstroms in as-synthesized or calcined form.

7. The process of claim 1 , wherein said porous crystalline material having MWW framework structure type is PSH-3, SSZ-25, ERB-1, ITQ-1, ITQ-2, ITQ-30, MCM-22, MCM-36, MCM-49, MCM-56, UZM-8, EMM-10, EMM-12, EMM-13 or mixtures thereof.

8. The process of claim 1 , wherein said alkylatable aromatic compound is selected from the group consisting of benzene, naphthalene, anthracene, naphthacene, perylene, coronene, phenanthrene and mixtures thereof.

9. The process of claim 1 , wherein said alkylatable aromatic compound is benzene, said alkylating agent is ethylene and said alkylated aromatic compound is ethylbenzene.

10. The process of claim 1 , wherein said alkylatable aromatic compound is benzene, said alkylating agent is propylene and said alkylated aromatic compound is cumene.

11. The process of claim 1 , wherein said alkylatable aromatic compound is benzene, said alkylating agent is butene and said alkylated aromatic compound is sec-butylbenzene.

12. The process of claim 1 , wherein said alkylatable aromatic compound is benzene, said alkylating agent is ethylene, said alkylated aromatic compound is ethylbenzene, and said at least partial liquid phase conversion conditions include a temperature of from about 100° C. to about 280° C., a pressure of about 3102 kPa or less, a weight hourly space velocity (WHSV) based on the ethylene of from about 0.1 to about 20 hr −1 , and a ratio of benzene to ethylene in the alkylation reactor of from about 0.5:1 to about 20:1 molar.

13. The process of claim 12 , wherein said treatment composition is zeolite beta.

14. The process of claim 12 , wherein said porous crystalline material having said MWW framework structure type has an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstroms.

15. The process of claim 12 , wherein said porous crystalline material having MWW framework structure type is PSH-3, SSZ-25, ERB-1, ITQ-1, ITQ-2, ITQ-30, MCM-22, MCM-36, MCM-49, MCM-56, UZM-8, EMM-10, EMM-12, EMM-13 or mixtures thereof.

16. The process of claim 1 , wherein said alkylatable aromatic compound comprises benzene, said alkylating agent is propylene, said alkylated aromatic compound comprises cumene, and said at least partial liquid phase conversion conditions include a temperature of less than about 200° C., a pressure of about 3102 kPa or less, a weight hourly space velocity (WHSV) based on propylene alkylating agent of from about 0.1 hr −1 to about 250 hr −1 , and a ratio of benzene to propylene in the alkylation reactor of from about 0.5:1 to about 20:1 molar.

17. The process of claim 16 , wherein said treatment composition is zeolite beta.

18. The process of claim 16 , wherein said porous crystalline material having said MWW framework structure type has an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstroms.

19. The process of claim 18 , wherein said porous crystalline material having MWW framework structure type is PSH-3, SSZ-25, ERB-1, ITQ-1, ITQ-2, ITQ-30, MCM-22, MCM-36, MCM-49, MCM-56, UZM-8, EMM-10, EMM-12, EMM-13 or mixtures thereof.

20. The process of claim 1 , wherein said treatment conditions of contacting step (a) includes a treatment weight hourly space velocity (WHSV) based on the untreated alkylatable aromatic compound in the range from about 5 to 70 hr −1 .

21. The process of claim 1 , said treatment composition absorbs greater than 900 wppm N-formyl morpholine (NFM) based on the weight of the treatment composition.

Assignees

• Vincent Matthew J
• Nanda Vijay
• Helton Terry E
• Exxonmobil Chem Patents Inc

Inventors

• Vincent Matthew J
• Nanda Vijay
• Helton Terry E

Classifications

• C07C2529/08

  of the faujasite type, e.g. type X or Y · CPC title

• C07C15/04

  Benzene · CPC title

• C07C2529/70

  of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 · CPC title

• C07C2/66 Primary

  Catalytic processes · CPC title

• C07C2529/18

  of the mordenite type · CPC title