IP Library Granted Patent US 7,238,817
Granted Patent B1
US 7,238,817 · App. 11/358,984 · Granted Jul 3, 2007

Direct epoxidation process

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Quick Facts
Patent No.
US 7,238,817
App. No.
11/358,984
Granted
Jul 3, 2007
Kind
B1
Abstract

A process is disclosed for reacting an olefin, hydrogen, and oxygen in a reactor in the presence of a catalyst comprising a transition metal zeolite and a noble metal to produce a reaction mixture comprising an epoxide and acidic byproducts. A portion of the reaction mixture is contacted with an adsorbent so that a treated mixture having a reduced amount of byproducts is produced. The treated mixture is recycled back to the reactor. Including an adsorption step should improve the catalyst productivity and epoxide selectivity.

Claims (23)

1. An epoxidation process comprising:

(a) reacting an olefin, hydrogen, and oxygen in the presence of an epoxidation catalyst comprising a transition metal zeolite and a noble metal to produce a reaction mixture comprising an epoxide and acidic byproducts;

(b) contacting a portion of the reaction mixture with an adsorbent to produce a treated mixture having a reduced amount of acidic byproducts; and

(c) recycling the treated mixture to step (a).

2. The process of claim 1 wherein the noble metal is supported on the transition metal zeolite.

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

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

5. The process of claim 1 wherein the noble metal is supported on a carrier.

6. The process of claim 5 wherein the carrier is selected from the group consisting of carbons, titanias, zirconias, niobias, silicas, aluminas, silica-aluminas, titania-silicas, zirconia-silicas, niobia-silicas, ion-exchange resins, and mixtures thereof.

7. The process of claim 5 wherein the transition metal zeolite is a titanium zeolite.

8. The process of claim 5 wherein the noble metal is selected from the group consisting of palladium, platinum, gold, rhenium, silver, and mixtures thereof.

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

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

11. The process of claim 1 wherein the adsorbent is selected from the group consisting of basic ion-exchange resins, aluminas, calcium oxide, magnesium oxide, activated carbons, and mixtures thereof.

12. The process of claim 1 wherein the adsorbent is a basic ion-exchange resin.

13. The process of claim 1 wherein the adsorbent is in a fixed-bed.

14. The process of claim 1 wherein the adsorbent is in a slurry.

15. The process of claim 1 wherein step (b) is performed in continuous flow mode.

16. The process of claim 1 wherein step (b) is performed in batch mode.

17. The process of claim 1 wherein the adsorbent is regenerated on-line.

18. The process of claim 1 wherein the adsorbent is in multiple adsorption vessels.

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

20. The process of claim 19 wherein the adsorbent is a basic ion-exchange 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 Feb 22, 2006
From: HAN, YUANZHANG
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 017610/0349 →