Alkylation process

• US 5,574,201 A
• Filed: 05/12/1995
• Issued: 11/12/1996
• Est. Priority Date: 05/12/1995
• Status: Expired due to Fees

• Current Assignee: Phillips Petroleum Company (ConocoPhillips)
• Original Assignee: Phillips Petroleum Company (ConocoPhillips)
• Inventors: Kallenbach, Lyle R.
• Primary Examiner(s): Pal, Asok
• Assistant Examiner(s): BULLOCK, IN SUK C
• Application Number:
  US08/440,262
• Time in Patent Office: 550 Days
• Field of Search: 585/730, 585/731, 585/721
• US Class Current: 585/730
• CPC Class Codes: C07C 2/62 with acids
• CPC Class Codes: C07C 2521/08 Silica
• CPC Class Codes: C07C 2531/025 Sulfonic acids
• CPC Class Codes: C07C 2531/26 containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24

Abstract

The alkylation of C₂ -C₁₂ alkanes (preferably isobutane) with C₂ -C₁₂ alkenes (preferably butene-2), in the presence of trifluoromethanesulfonic acid on a solid inorganic material as catalyst, is carried out with dicyclopentadiene and/or tetrahydrodicyclopentadiene as additional alkylating agent(s).

Claims

1. In a process for alkylating at least one alkane containing 2-12 carbon atoms per molecule with at least one alkene containing 2-12 carbon atoms per molecule in the presence of a catalyst comprising trifluoromethanesulfonic acid and at least one solid inorganic material so as to produce at least one product alkane containing more carbon atoms than said at least one feed alkane, the improvement which comprises the presence of at least one tricyclic hydrocarbon selected from the group consisting of dicyclopentadiene, tetrahydrodicyclopentadiene and mixtures thereof in the feed comprising said at least one feed alkane and said at least one feed alkene.

2. In a process for alkylating at least one alkane containing 2-12 carbon atoms per molecule with at least one alkene containing 2-12 carbon atoms per molecule in the presence of a catalyst comprising trifluoromethanesulfonic acid and at least one solid inorganic material so as to produce at least one product alkane containing more carbon atoms than said at least one feed alkane, the improvement which comprises the presence of dicyclopentadiene in the feed comprising said at least one feed alkane and said at least one feed alkene.

3. A process in accordance with claim 2, wherein the content of dicyclopentadiene in said feed is about 0.05-3.0 weight percent.

4. A process in accordance with claim 3, wherein said at least one solid inorganic material is selected from the group consisting of alumina, silica, silica-alumina, titania, zirconia, aluminum phosphate, aluminum oxide/phosphate, aluminum borate, aluminum borate/oxide, boron oxide, boron phosphate, aluminum boron phosphate, boron sulfate, zirconium sulfate, and mixtures thereof.

5. A process in accordance with claim 4, wherein said at least one solid inorganic material is silica.

6. A process in accordance with claim 3, wherein said at least one feed alkane contains 4-8 carbon atoms per molecule, said at least one feed alkene contains 4-6 carbon atoms per molecule, the content of dicyclopentadiene in said feed is about 0.05-3.0 weight-%, and said at least one solid inorganic is selected from the group consisting of alumina, silica, silica-alumina, titania, zirconia, aluminum phosphate, aluminum oxide/phosphate, aluminum borate, aluminum borate/oxide, boron oxide, boron phosphate, aluminum boron phosphate, boron sulfate, zirconium sulfate, and mixtures thereof.

7. A process in accordance with claim 6, wherein the content of dicyclopentadiene in said feed is about 0.1-1.0 weight-%.

8. A process in accordance with claim 7, wherein the weight ratio of trifluoromethanesulfonic acid to said at least one solid inorganic material is in the range of about 0.01:

1 to about 0.4;

1.

9. A process in accordance with claim 8, wherein said at least one solid inorganic material is silica.

10. A process in accordance with claim 9, wherein said at least one feed alkane is isobutane and said at least one feed alkene is butene-2.

11. In a process for alkylating at least one alkane containing 2-12 carbon atoms per molecule with at least one alkene containing 2-12 carbon atoms per molecule in the presence of a catalyst comprising trifluoromethanesulfonic acid and at least one solid inorganic material so as to produce at least one product alkane containing more carbon atoms than said at least one feed alkane, the improvement which comprises the presence of tetrahydrocyclopentadiene in the feed comprising said at least one feed alkane and said at least one feed alkene.

12. A process in accordance with claim 11, wherein the content of tetrahydrodicyclopentadiene in said feed is about 0.05-3.0 weight-%.

13. A process in accordance with claim 12, wherein said at least one solid inorganic material is selected from the group consisting of alumina, silica, silica-alumina, titania, zirconia, aluminum phosphate, aluminum oxide/phosphate, aluminum borate, aluminum borate/oxide, boron oxide, boron phosphate, aluminum boron phosphate, boron sulfate, zirconium sulfate, and mixtures thereof.

14. A process in accordance with claim 13, wherein said at least one solid inorganic material is silica.

15. A process in accordance with claim 12, wherein said at least one feed alkane contains 4-8 carbon atoms per molecule, said at least one feed alkene contains 4-6 carbon atoms per molecule, the content of dicyclopentadiene in said feed is about 0.05-3.0 weight-%, and said at least one solid inorganic is selected from the group consisting of alumina, silica, silica-alumina, titania, zirconia, aluminum phosphate, aluminum oxide/phosphate, aluminum borate, aluminum borate/oxide, boron oxide, boron phosphate, aluminum boron phosphate, boron sulfate, zirconium sulfate, and mixtures thereof.

16. A process in accordance with claim 15, wherein the content of tetrahydrodicyclopentadiene in said feed is about 0.1-1.0 weight-%.

17. A process in accordance with claim 16, wherein the weight ratio of trifluoromethanesulfonic acid to said at least one solid inorganic material is in the range of about 0.01:

1 to about 0.4;

1.

18. A process in accordance with claim 17, where said solid inorganic material is silica.

19. A process in accordance with claim 18, wherein said at least one feed alkane is isobutane and said at least one feed alkene is butene-2.