IP Library Granted Patent US 7,259,280
Granted Patent B1
US 7,259,280 · App. 11/386,131 · Granted Aug 21, 2007

Process for producing alkenyl alcohols

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Quick Facts
Patent No.
US 7,259,280
App. No.
11/386,131
Granted
Aug 21, 2007
Kind
B1
Abstract

A process for producing an alkenyl alcohol from a diol is disclosed. The process comprises dehydrating a diol in the presence of a catalyst comprising cerium oxide supported on a carrier. The carrier has a surface area in the range of 0.1 to 50 m 2 /g. The catalyst is more active than unsupported cerium oxide.

Claims (20)

1. A process for producing an alkenyl alcohol, which comprises dehydrating a diol in the presence of a catalyst comprising cerium oxide supported on a carrier, wherein the carrier has a surface area in the range of 0.1 to 50 m 2 /g.

2. The process of claim 1 wherein the catalyst further comprises a metal oxide.

3. The process of claim 2 wherein the metal oxide is selected from the group consisting of oxides of aluminum, magnesium, calcium, barium, iron, cobalt, nickel, titanium, vanadium, scandium, yttrium, and mixtures thereof.

4. The process of claim 1 wherein the carrier is selected from the group consisting of alumina, silica, titania, zirconia, magnesia, calcium oxide, calcium carbonate, magnesium carbonate, silica-alumina, silica-titania, silica-zirconia, carbon, and mixtures thereof.

5. The process of claim 1 wherein the carrier is an alumina.

6. The process of claim 1 wherein the carrier is an alpha-alumina.

7. The process of claim 1 wherein the carrier has a surface area in the range of 1 to 10 m 2 /g.

8. The process of claim 1 performed at a temperature in the range of 250 to 450° C.

9. The process of claim 1 performed at a temperature in the range of 300 to 400° C.

10. The process of claim 1 performed in the presence of an inert gas.

11. The process of claim 1 performed in a continuous flow mode.

12. The process of claim 1 wherein the catalyst is in a fixed bed.

13. The process of claim 1 performed at a pressure of 0.5 to 1.5 atmospheres.

14. The process of claim 1 wherein the diol is a gas under the reaction conditions.

15. The process of claim 1 wherein the diol is a 1,3-diol.

16. The process of claim 1 wherein the diol is 1,3-propanediol and the alkenyl alcohol is allyl alcohol.

17. The process of claim 1 wherein the diol is 2-methyl-1,3-propanediol and the alkenyl alcohol is 2-methyl-2-propen-1-ol.

18. A process for producing allyl alcohol, which comprises dehydrating 1,3-propanediol in the presence of a catalyst comprising cerium oxide supported on a carrier, wherein the carrier has a surface area in the range of 0.1 to 50 m 2 /g.

19. The process of claim 18 wherein the catalyst is in a fixed bed.

20. The process of claim 18 wherein the carrier is an alumina.

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 Mar 22, 2006
From: KAHN, ANDREW P.; HARRIS, STEPHEN H.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 017725/0452 →