IP Library Granted Patent US 7,026,492
Granted Patent B1
US 7,026,492 · App. 10/977,444 · Granted Apr 11, 2006

Direct epoxidation process using modifiers

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Quick Facts
Patent No.
US 7,026,492
App. No.
10/977,444
Granted
Apr 11, 2006
Kind
B1
Abstract

The invention is a process for epoxidizing an olefin with hydrogen and oxygen in the presence of a noble metal-containing titanium or vanadium zeolite and a modifier selected from the group consisting of carbon monoxide, methylacetylene, and propadiene. The process results in significantly reduced alkane by-product formed by the hydrogenation of olefin compared to processes that do not use the carbon monoxide, methylacetylene, and/or propadiene modifier.

Claims (16)

1. A process for producing an epoxide comprising reacting an olefin, oxygen, and hydrogen in the presence of a noble metal-containing titanium or vanadium zeolite catalyst and a modifier selected from the group consisting of methylacetylene and propadiene.

2. The method of claim 1 wherein the noble metal-containing titanium or vanadium zeolite catalyst comprises titanium silicalite and palladium.

3. The method of claim 1 wherein the noble metal-containing titanium or vanadium zeolite catalyst comprises titanium silicalite, palladium, and one or more metals selected from the group consisting of gold and platinum.

4. The method of claim 1 wherein the noble metal-containing titanium or vanadium zeolite catalyst comprises a mixture of palladium-containing titanium or vanadium zeolite and palladium-free titanium or vanadium zeolite.

5. The process of claim 1 wherein the olefin is a C 2 –C 6 olefin.

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

7. The process of claim 1 wherein the modifier is a mixture of methylacetylene and propadiene.

8. The process of claim 1 further comprising a solvent selected from the group consisting of oxygenated hydrocarbons, aromatic and aliphatic hydrocarbons, chlorinated aromatic and aliphatic hydrocarbons, supercritical CO 2 , and water.

9. The process of claim 1 further comprising a solvent selected from the group consisting of methanol, ethanol, isopropanol, and tert-butanol, and water.

10. A process for producing propylene oxide comprising reacting propylene, hydrogen and oxygen in a solvent in the presence of a palladium-containing titanium zeolite catalyst and a modifier selected from the group consisting of methylacetylene and propadiene.

11. The method of claim 10 wherein the palladium-containing titanium zeolite catalyst comprises titanium silicalite and palladium.

12. The method of claim 10 wherein the palladium-containing titanium zeolite catalyst comprises titanium silicalite, palladium, and one or more metals selected from the group consisting of gold and platinum.

13. The method of claim 10 wherein the palladium-containing titanium zeolite catalyst comprises a mixture of palladium-containing titanium zeolite and palladium-free titanium zeolite.

14. The process of claim 10 wherein the modifier is a mixture of methylacetylene and propadiene.

15. The process of claim 10 wherein the solvent is selected from the group consisting of oxygenated hydrocarbons, aromatic and aliphatic hydrocarbons, chlorinated aromatic and aliphatic hydrocarbons, supercritical CO 2 , and water.

16. The process of claim 10 wherein the solvent is selected from the group consisting of methanol, ethanol, isopropanol, tert-butanol, and water.

Assignments (21)
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 →
CHANGE OF NAME Recorded Jun 27, 2005
From: ARCO CHEMICAL TECHNOLOGY, L.P.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 016206/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 29, 2004
From: KAMINSKY, MARK P.
To: ARCO CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 015952/0090 →