IP Library Granted Patent US 7,432,384
Granted Patent B2
US 7,432,384 · App. 11/257,955 · Granted Oct 7, 2008

Direct epoxidation process

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Quick Facts
Patent No.
US 7,432,384
App. No.
11/257,955
Granted
Oct 7, 2008
Kind
B2
Abstract

A process is disclosed for the epoxidation of an olefin with hydrogen and oxygen in the presence of an oxidation catalyst comprising a transition metal zeolite and a polymer-encapsulated noble metal catalyst. The noble metal catalyst comprises a noble metal and an ion-exchange resin. The process using the polymer-encapsulated noble metal catalyst gives higher epoxide productivity than a process that uses a noble metal catalyst which is not encapsulated by a polymer.

Claims (20)

1. An epoxidation process comprising reacting an olefin, hydrogen, and oxygen in the presence of an oxidation catalyst comprising a transition metal zeolite, and a polymer-encapsulated noble metal catalyst comprising a noble metal and an ion-exchange resin.

2. The process of claim 1 wherein the transition metal zeolite is a titanium zeolite.

3. The process of claim 1 wherein the transition metal zeolite is TS-1.

4. The process of claim 1 wherein the noble metal is selected from the group consisting of palladium, platinum, gold, rhenium, silver, and mixtures thereof.

5. The process of claim 1 wherein the ion-exchange resin has a capacity of from 1 to 10 eq/kg.

6. The process of claim 1 wherein the ion-exchange resin is an acidic ion-exchange resin.

7. The process of claim 1 wherein the ion-exchange resin is a sulfonic acid polystyrene resin.

8. The process of claim 1 wherein the polymer is selected from the group consisting of polystyrenics, polyolefins, and mixtures thereof.

9. The process of claim 1 wherein the polymer is polystyrene.

10. The process of claim 1 wherein the oxidation catalyst is encapsulated within a polymer.

11. The process of claim 1 wherein the oxidation catalyst is encapsulated within the same polymer.

12. The process of claim 1 wherein the ion-exchange resin comprises a cation selected from the group consisting of alkali metal and alkaline earth metal ions, and mixtures thereof.

13. The process of claim 1 wherein the noble metal catalyst further comprises a component selected from the group consisting of titania, zirconia, niobia, silica, alumina, silica-alumina, titania-silica, zirconia-silica, niobia-silica, and mixtures thereof.

14. The process of claim 1 wherein the reaction is performed in the presence of a solvent.

15. The process of claim 14 wherein the solvent is selected from the group consisting of alcohols, ethers, esters, ketones, carbon dioxide, water, and mixtures thereof.

16. The process of claim 14 wherein the reaction is performed in the presence of a buffer.

17. The process of claim 16 wherein the buffer comprises an anion selected from the group consisting of phosphate, carbonate, sulfate, hydroxide, acetate, and the mixtures thereof; and a cation selected from the group consisting of ammonium, alkylammonium, alkylphosphonium, alkali metal, and alkaline earth metal ions, and the mixtures thereof.

18. The process of claim 1 wherein the olefin is one or more C 2 -C 6 olefins.

19. The process of claim 1 wherein the olefin is propylene.

20. An epoxidation process comprising reacting propylene, hydrogen, and oxygen in a solvent in the presence of a buffer, an oxidation catalyst comprising a titanium zeolite, and a polymer-encapsulated noble metal catalyst comprising a noble metal and a sulfonic acid polystyrene resin.

Assignments (20)
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 024337/0856 →
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 →
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 →
RELEASE OF LYONDELL CHEMICAL TECHNOLOGY, L.P. PATENT SECURITY AGREEMENT Recorded Mar 20, 2008
From: JPMORGAN CHASE BANK, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 020679/0063 →
SECURITY AGREEMENT Recorded Sep 15, 2006
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: JPMORGAN CHASE BANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 018260/0306 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2005
From: LE-KHAC, BI; GREY, ROGER A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 017147/0351 →