IP Library Granted Patent US 8,124,797
Granted Patent B2
US 8,124,797 · App. 12/459,065 · Granted Feb 28, 2012

Epoxidation process

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Quick Facts
Patent No.
US 8,124,797
App. No.
12/459,065
Granted
Feb 28, 2012
Kind
B2
Abstract

This invention is a process for producing propylene oxide. The process comprises first contacting a titanium zeolite with a reaction feed comprising propylene, hydrogen peroxide, tertiary butyl alcohol, and water to produce a product stream comprising propylene, propylene oxide, propylene glycol, tertiary butyl alcohol, and water. The product stream is distilled to produce a first overhead stream comprising propylene and a first bottoms stream comprising propylene oxide, propylene glycol, tertiary butyl alcohol, and water. The first bottoms stream is distilled to produce a second overhead stream comprising propylene oxide and a second bottoms product stream comprising propylene glycol, tertiary butyl alcohol, and water. The second bottoms stream is distilled to produce a third overhead stream comprising an azeotrope of tertiary butyl alcohol and water and a third bottoms stream comprising propylene glycol and water.

Claims (20)

1. A process for producing propylene oxide comprising:

(a.) contacting a titanium zeolite with a reaction feed comprising propylene, hydrogen peroxide, tertiary butyl alcohol, and water to produce a product stream comprising propylene, propylene oxide, propylene glycol, tertiary butyl alcohol, and water;

(b.) distilling the product stream to produce a first overhead stream comprising propylene and a first bottoms stream comprising propylene oxide, propylene glycol, tertiary butyl alcohol, and water;

(c.) distilling the first bottoms stream to produce a second overhead stream comprising propylene oxide and a second bottoms product stream comprising propylene glycol, tertiary butyl alcohol, and water; and distilling the second bottoms stream to produce a third overhead stream comprising an azeotrope of tertiary butyl alcohol and water and a third bottoms stream comprising propylene glycol and water.

2. The process of claim 1 wherein the titanium zeolite is a titanium-MWW zeolite.

3. The process of claim 1 wherein the hydrogen peroxide is formed by the in situ reaction of hydrogen and oxygen in the presence of a noble metal catalyst.

4. The process of claim 1 , further comprising recycling the third overhead stream back to step (a).

5. The process of claim 1 , further comprising distilling the third bottoms stream to produce a fourth overhead stream comprising water and a fourth bottoms stream comprising propylene glycol.

6. A process for producing propylene oxide comprising:

(a) contacting a catalyst comprising a titanium-MWW zeolite and a noble metal with a reaction feed comprising propylene, hydrogen, oxygen, tertiary butyl alcohol, and water to produce a product stream comprising propylene, propylene oxide, propylene glycol, tertiary butyl alcohol, and water;

(b) distilling the product stream to produce a first overhead stream comprising propylene and a first bottoms stream comprising propylene oxide, propylene glycol, tertiary butyl alcohol, and water;

(c) distilling the first bottoms stream to produce a second overhead stream comprising propylene oxide and a second bottoms product stream comprising propylene glycol, tertiary butyl alcohol, and water; and

(d) distilling the second bottoms stream to produce a third overhead stream comprising an azeotrope of tertiary butyl alcohol and water and a third bottoms stream comprising propylene glycol and water.

7. The process of claim 6 wherein the noble metal is palladium.

8. The process of claim 6 wherein the catalyst contains 0.01 to 10 weight percent of the noble metal and 0.001 to 5 weight percent of an additional metal selected from the group consisting of lead, bismuth, and rhenium.

9. The process of claim 6 wherein the catalyst comprises a noble metal supported on the titanium-MWW zeolite.

10. The process of claim 6 wherein the noble metal is supported on a carrier.

11. The process of claim 10 wherein the carrier is selected from the group consisting of carbon, titania, zirconia, niobia, silica, alumina, silica-alumina, tantalum oxide, molybdenum oxide, tungsten oxide, titania-silica, zirconia-silica, niobia-silica, and mixtures thereof.

12. The process of claim 6 , further comprising recycling the third overhead stream back to step (a).

13. The process of claim 6 , further comprising distilling the third bottoms stream to produce a fourth overhead stream comprising water and a fourth bottoms stream comprising propylene glycol.

Assignments (10)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2009
From: MILLER, JAY F.; SPEIDEL, JR., JOHN H.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 023018/0224 →