IP Library Granted Patent US 7,816,572
Granted Patent B2
US 7,816,572 · App. 11/890,728 · Granted Oct 19, 2010

Propylene and isoprene production

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Quick Facts
Patent No.
US 7,816,572
App. No.
11/890,728
Granted
Oct 19, 2010
Kind
B2
Abstract

A process for producing propylene and isoprene from a feed stream comprising 1-butene and isobutene is disclosed. The feed stream is reacted in a catalytic distillation reactor containing an olefin isomerization catalyst to produce an overhead stream comprising 2-butene and isobutene and a bottoms stream comprising 2-butene. The overhead stream is reacted in the presence of a metathesis catalyst to produce propylene and isoamylenes. Isoprene is produced by dehydrogenation of isoamylenes.

Claims (20)

1. A process comprising: (a) reacting a feed stream comprising 1-butene and isobutene in the presence of an isomerization catalyst to generate a first reaction mixture, and concurrently distilling the first reaction mixture to produce an overhead stream comprising 2-butene and isobutene and a bottoms stream comprising 2-butene; (b) reacting the overhead stream in the presence of a first metathesis catalyst to generate a second reaction mixture comprising isoamylenes, butenes, and propylene; (c) distilling the second reaction mixture to isolate isoamylenes; and (d) dehydrogenating isoamylenes from step (c) to produce isoprene.

2. The process of claim 1 further comprising reacting the bottoms stream from step (a) with ethylene in the presence of a second metathesis catalyst to produce a third reaction mixture comprising ethylene, propylene, 1-butene, 2-butene, and C 5 and higher olefins; distilling the third reaction mixture into ethylene, propylene, a butenes stream, and a heavy stream comprising the C 5 and higher olefins.

3. The process of claim 2 further comprising recycling the separated ethylene to the metathesis reaction of the bottoms stream from step (a) and ethylene.

4. The process of claim 3 further comprising recycling the butenes stream to step (a).

5. The process of claim 1 wherein the feed stream comprises 2-butene.

6. The process of claim 1 wherein the feed stream is raffinate-1.

7. The process of claim 1 wherein the isomerization catalyst is a basic catalyst.

8. The process of claim 1 wherein the isomerization catalyst comprises magnesium oxide.

9. The process of claim 1 wherein the isomerization catalyst is a hydroisomerization catalyst.

10. The process of claim 1 wherein the hydroisomerization catalyst comprises Pd and alumina.

11. The process of claim 10 wherein the feed stream comprises hydrogen.

12. The process of claim 10 wherein the isomerization reaction is performed at a temperature in the range of from 100 to 250° F.

13. The process of claim 10 wherein the isomerization reaction is performed at a pressure in the range of from 50 to 250 psig.

14. The process of claim 1 wherein the dehydrogenation reaction is performed at a temperature in the range of from 700 to 1300° F.

15. The process of claim 1 wherein the first metathesis catalyst comprises a transition metal oxide comprising an element selected from the group consisting of cobalt, molybdenum, rhenium, tungsten, and mixtures thereof.

16. The process of claim 1 wherein the first metathesis catalyst comprises tungsten oxide and silica.

17. The process of claim 16 wherein the first metathesis catalyst further comprises magnesium oxide.

18. The process of claim 2 wherein the second metathesis comprises a transition metal oxide comprising an element selected from the group consisting of cobalt, molybdenum, rhenium, tungsten, and mixtures thereof.

19. The process of claim 2 wherein the second metathesis catalyst comprises tungsten oxide and silica.

20. The process of claim 19 wherein the second metathesis catalyst further comprises magnesium oxide.

Assignments (18)
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032123/0799 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: CITIBANK, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032125/0296 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032137/0156 →
APPOINTMENT OF SUCCESSOR ADMINISTRATIVE AGENT Recorded Jan 23, 2014
From: UBS AG, STAMFORD BRANCH
To: BANK OF AMERICA, N.A.
Reel/Frame 032137/0639 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: BANK OF AMERICA, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032138/0134 →
SECURITY AGREEMENT Recorded May 19, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 024402/0681 →
SECURITY AGREEMENT Recorded May 18, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024397/0818 →
SECURITY AGREEMENT Recorded May 7, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 024342/0801 →
SECURITY AGREEMENT Recorded May 6, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 024342/0421 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0705 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0285 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0020 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0856 →
SECURITY AGREEMENT Recorded Oct 30, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 023449/0138 →
SECURITY AGREEMENT Recorded Apr 9, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
Reel/Frame 022708/0830 →
SECURITY AGREEMENT Recorded Aug 4, 2008
From: BASELL POLYOLEFINE GMBH; ARCO CHEMICAL TECHNOLOGY L.P.; ARCO CHEMICAL TECHNOLOGY, INC.; ATLANTIC RICHFIELD COMPANY; BASELL NORTH AMERICA, INC.; BASELL POLYOLEFIN GMBH; LYONDELL CHEMICAL COMPANY; EQUISTAR CHEMICALS, L.P.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021354/0708 →
GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AND PATENT APPLICATIONS Recorded Mar 26, 2008
From: BASELL POLYOLEFINE GMBH; ARCO CHEMICAL TECHNOLOGY L.P.; ARCO CHEMICAL TECHNOLOGY, INC.; ATLANTIC RICHFIELD COMPANY; BASELL NORTH AMERICA, INC.; EQUISTAR CHEMICALS. LP.; LYONDELL CHEMICAL COMPANY; LYONDELL CHEMICAL TECHNOLOGY, L.P.; LYONDELL PETROCHEMICAL COMPANY; NATIONAL DISTILLERS AND CHEMICAL CORPORATION; OCCIDENTAL CHEMICAL CORPORATION; OLIN CORPORATION; QUANTUM CHEMICAL CORPORATION; BASELL POLYOLEFIN GMBH
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 020704/0562 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2007
From: LEYSHON, DAVID W.; ZAK, THOMAS S.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 019729/0113 →