IP Library Granted Patent US 7,741,498
Granted Patent B2
US 7,741,498 · App. 12/231,220 · Granted Jun 22, 2010

Propylene oxide process

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Quick Facts
Patent No.
US 7,741,498
App. No.
12/231,220
Granted
Jun 22, 2010
Kind
B2
Abstract

A process for making propylene oxide from propylene is disclosed. The process comprises reacting propylene, oxygen, and hydrogen in the presence of a catalyst and a solvent to produce a reaction mixture comprising propylene oxide. Separation of propylene, oxygen, hydrogen, and propylene oxide from the reaction mixture results in a residual mixture comprising methanol. A portion of the residual mixture is recycled to the reaction. A portion of the residual mixture is distilled to generate a distilled methanol stream, which is recycled to the reaction.

Claims (15)

1. A process for producing propylene oxide comprising

(a) reacting propylene, oxygen, and hydrogen in the presence of a catalyst and methanol to produce a reaction mixture comprising propylene oxide;

(b) separating propylene, oxygen, hydrogen, and propylene oxide from the reaction mixture to generate a residual mixture comprising methanol:

(c) recycling from 10 to 30 wt % of the residual mixture to step (a);

(d) separating a portion of the residual mixture to generate a methanol stream; and

(e) recycling the methanol stream to step (a);

wherein the reaction mixture comprises methanol and water with a methanol to water weight ratio greater than 7:3.

2. The process of claim 1 wherein the methanol stream comprises at least 95 wt % methanol.

3. The process of claim 1 wherein the methanol stream comprises at least 98 wt % methanol.

4. The process of claim 1 wherein the reaction mixture comprises methanol and water with a methanol to water weight ratio greater than 8:2.

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

6. The process of claim 5 wherein the buffer comprises an ammonium ion and a phosphate ion with an ammonium to phosphate molar ratio of from 1:1 to 3:1.

7. The process of claim 1 wherein the catalyst comprises a transition metal zeolite and a noble metal.

8. The process of claim 7 wherein the transition metal zeolite is titanium silicalite-1.

9. The process of claim 7 wherein the noble metal is selected from the group consisting of palladium, platinum, gold, rhenium, silver, and mixtures thereof.

Assignments (14)
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: 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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2008
From: CHANG, TE; SAWYER, GARY A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 021519/0535 →