IP Library Granted Patent US 7,528,269
Granted Patent B2
US 7,528,269 · App. 11/312,036 · Granted May 5, 2009

Process for oxidizing organic compounds

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Quick Facts
Patent No.
US 7,528,269
App. No.
11/312,036
Granted
May 5, 2009
Kind
B2
Abstract

This invention is a process for oxidizing an organic compound with a hydrogen peroxide solution produced by reacting hydrogen and oxygen in the presence of an oxidation catalyst. The hydrogen peroxide is produced by reacting hydrogen and oxygen in a solvent in the presence of a H 2 O 2 -producing catalyst comprising a polymer-encapsulated combination of a noble metal and an ion-exchange resin. Polymer encapsulation of the H 2 O 2 -producing catalyst improves its productivity in making hydrogen peroxide and is expected to reduce metal loss.

Claims (18)

1. A process which comprises:

(a) reacting hydrogen and oxygen in a solvent in the presence of a H 2 O 2 -producing catalyst comprising a polymer-encapsulated combination of a noble metal and a sulfonic acid polystyrene resin having 1 to 10 equivalents per kilogram of functional groups, to obtain a hydrogen peroxide solution; and

(b) reacting an olefin with the hydrogen peroxide solution in the presence of an oxidation catalyst to produce an epoxide.

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

3. The process of claim 1 wherein the noble metal is palladium.

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

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

6. The process of claim 1 wherein the H 2 O 2 -producing catalyst further comprises a component selected from the group consisting of carbon, titania, zirconia, niobia, silica, alumina, silica-alumina, titania-silica, zirconia-silica, niobia-silica, and mixtures thereof.

7. The process of claim 1 wherein step (a) is performed in the presence of a hydrogen peroxide stabilizer.

8. The process of claim 1 wherein the solvent is an oxygenated solvent.

9. The process of claim 1 wherein the solvent is selected from the group consisting of alcohols, ethers, esters, ketones, carbon dioxide, water, and mixtures thereof.

10. The process of claim 1 wherein step (b) is performed in the presence of a buffer.

11. The process of claim 1 wherein the oxidation catalyst is a titanium zeolite.

12. The process of claim 11 wherein the titanium zeolite is TS-1.

13. A process which comprises:

(a) reacting hydrogen and oxygen in a solvent in the presence of a H 2 O 2 -producing catalyst comprising a polymer-encapsulated combination of palladium and a sulfonic acid polystyrene resin, to obtain a hydrogen peroxide solution; and

(b) reacting propylene with the hydrogen peroxide solution in the presence of a titanium zeolite to produce propylene oxide.

14. The process of claim 13 wherein the titanium zeolite is TS-1.

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 Dec 20, 2005
From: LE-KHAC, BI; GREY, ROGER A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 017396/0488 →