Process for removal of alkynes and/or dienes from an olefin stream

• US 7,115,789 B2
• Filed: 03/28/2003
• Issued: 10/03/2006
• Est. Priority Date: 03/28/2003
• Status: Expired due to Fees

• Current Assignee: ExxonMobil Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: ExxonMobil Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Kuechler, Keith Holroyd, Lumgair, David R. Jr.
• Primary Examiner(s): Dang, Thuan D.
• Application Number:
  US10/403,229
• Publication Number:
  US 20040192982A1
• Time in Patent Office: 1,285 Days
• Field of Search: 585/265, 585/259
• US Class Current: 585/265
• CPC Class Codes: C07C 1/20 starting from organic compounds containing only oxygen atoms as heteroatoms
• CPC Class Codes: C07C 11/04 Ethylene
• CPC Class Codes: C07C 11/06 Propene
• CPC Class Codes: C07C 7/163 by hydrogenation
• CPC Class Codes: C07C 7/167 for removal of compounds containing a triple carbon-to-carbon bond
• CPC Class Codes: C10G 45/32 Selective hydrogenation of the diolefin or acetylene compounds
• CPC Class Codes: C10G 45/40 containing platinum group metals or compounds thereof
• CPC Class Codes: C10G 65/06 at least one step being a selective hydrogenation of the diolefins
• CPC Class Codes: Y02P 30/20 using bio-feedstock
• CPC Class Codes: Y02P 30/40 Ethylene production

Abstract

The present invention is a process for removing alkynes and/or dienes from an olefin product stream withdrawn from an oxygenate-to-olefins reactor. The process comprises hydrogenating a first olefin stream that has alkynes and/or dienes in the presence of excess hydrogen and a first hydrogenation catalyst. The hydrogenation of the first olefin stream produces a second olefin stream that has unreacted hydrogen. The second olefin stream is contacted with a second hydrogenation catalyst producing a third olefin stream. The third olefin stream has low levels of hydrogen and alkynes and/or dienes.

Claims

1. A process for hydrogenating byproducts selected from the group consisting of alkynes, dienes and mixtures thereof in an olefin product stream from an oxygenate-to-olefins reactor, the process comprising the steps of:

(a) contacting an oxygenate with a molecular sieve catalyst in the oxygenate-to-olefins reactor to provide the olefin product stream;

(b) isolating from the olefin product stream a first olefin stream containing 25 mol. % or more ethylene or 25 mol. % or more propylene, based upon the composition of the first olefin stream, and 500 mppm or less of the alkyne or diene byproduct;

(c) hydrogenating the first olefin stream to produce a second olefin stream; and

(d) hydrogenating the second olefin stream in the presence of from 100 mppm to 1000 mppm hydrogen, based upon the weight of the second olefin stream, to produce a third olefin stream containing 20 mppm or less hydrogen, based upon the composition of the third olefin stream.

2. The process of claim 1, wherein about 1.05 moles or more of hydrogen are present for every mole of alkyne or diene byproduct in the first olefin stream.

3. The process of claim 1, wherein from about 1.5 moles to about 50 moles of hydrogen are present for every mole of alkyne or diene byproduct in the first olefin stream.

4. The process of claim 1, wherein from about 1.5 moles to about 10 moles of hydrogen arc present for every mole of alkyne or diene byproduct in the first olefin stream.

5. The process of claim 1, further comprising heating the first olefin stream.

6. The process of claim 5, wherein the first olefin stream is heated to a temperature ranging from about 100°

F. (38°

C.) to about 250°

F. (121°

C.).

7. The process of claim 6, wherein the first olefin stream is heated to a temperature ranging from about 120°

F. (49°

C.) to about 200°

F. (93°

C.).

8. The process of claim 7, wherein the first olefin stream is heated to a temperature ranging from about 150°

F. (66°

C.) to about 190°

F. (88°

C.).

9. The process of claim 1, wherein hydrogenating the first olefin stream occurs at a pressure ranging from about 50 psia (344 kPaa) to about 400 psia (2760 kPaa).

10. The process of claim 9, wherein hydrogenating the first olefin stream occurs at a pressure ranging from about 200 psia (1380 kPaa) to about 300 psia (2070 kPaa).

11. The process of claim 10, wherein hydrogenating the first olefin stream occurs at a pressure ranging from about 250 psia (1720 kPaa) to about 300 psia (2070 kPaa).

12. The process of claim 1, wherein first olefin stream is hydrogenated in the presence of a first hydrogenating catalyst that is an elemental Group VIII metal catalyst.

13. The process of claim 12, wherein the first catalyst is an elemental noble metal on a substrate selected from the group consisting of silica, alumina and mixtures thereof with a co-catalyst selected from the group consisting of elemental silver, vanadium, iodine and combinations thereof.

14. The process of claim 12, wherein the first catalyst is an elemental palladium catalyst.

15. The process of claim 14, wherein the first catalyst is an elemental palladium catalyst on a substrate selected from the group consisting of silica, alumina and/or mixtures thereof with a co-catalyst selected from the group consisting of elemental silver, vanadium, iodine and combinations thereof.

16. The process of claim 1, wherein the first olefin stream is heated with the third olefin stream in a heat exchanger.

17. The process of claim 1, wherein the first olefin stream contains 50 mol. % or more olefin based upon the composition of the first olefin stream.

18. The process of claim 1, wherein the first olefin stream contains about 90 mol. % or more olefin based upon the composition of the first olefin stream.

19. The process of claim 1, wherein the first olefin stream contains about 98 mol. % or more olefin based upon the composition of the first olefin stream.

20. The process of claim 1, wherein the first olefin stream comprises about 200 mppm or less alkyne and or diene byproduct.

21. The process of claim 1, wherein the first olefin stream comprises about 90 mol. % or more propylene based upon the composition of the first olefin stream.

22. The process of claim 1, wherein the alkyne is methyl acetylene and the diene is propadiene and the first olefin stream comprises about 500 mppm or less byproducts based upon the composition of the first olefin stream.

23. The process of claim 1, wherein the temperature of the second olefin stream ranges from about 100°

F. (38°

C.) to about 250°

F. (121°

C.).

24. The process of claim 1, wherein the temperature of the second olefin stream ranges from about 120°

F. (49°

C.) to about 200°

F. (93°

C.).

25. The process of claim 1, wherein the temperature of the second olefin stream ranges from about 150°

F. (66°

C.) to about 190°

F. (88°

C.).

26. The process of claim 1, wherein the second olefin stream is hydrogenated at a pressure ranging from about 50 psia (344 kPaa) to about 400 psia (2760 kPaa).

27. The process of claim 1, wherein the second olefin scream is hydrogenated at a pressure ranging from about 200 psia (1380 kPaa) to about 300 psia (2070 kPaa).

28. The process of claim 1, wherein the second olefin stream is hydrogenated at a pressure ranging from about 250 psia (1720 kPaa) to about 300 psia (2070 kPaa).

29. The process of claim 1, wherein the second olefin stream is hydrogenated in the presence of a second hydrogenating catalyst that is an elemental Group VIII metal catalyst.

30. The process of claim 29, wherein the second catalyst is an elemental noble metal on a substrate selected from the group consisting of silica and/or alumina with a co-catalyst selected from the group comprising elemental iron catalyst, elemental nickel catalyst, and mixtures thereof.

31. The process of claim 30, wherein the second catalyst is an elemental palladium catalyst.

32. The process of claim 31, wherein the second catalyst is an elemental palladium catalyst on a substrate selected from the group consisting of silica, alumina and mixtures thereof with a co-catalyst selected from the group consisting of elemental iron, elemental nickel and mixtures thereof.

33. The process of claim 1, wherein the first olefin stream and the second olefin stream are hydrogenated in the presence of a first and second hydrogenation catalyst in which the first catalyst is the same as the second catalyst.

34. The process of claim 1, wherein the third olefin stream is converted to polyolefin.