IP Library › Granted Patent US 7,399,726
Granted Patent B2
US 7,399,726 · App. 11/087,776 · Granted Jul 15, 2008

Process for direct oxidation of propylene to propylene oxide and large particle size titanium silicalite catalysts for use therein

Assignee: Lyondell Chemical Technology, L.P.
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Quick Facts
Patent No.
US 7,399,726
App. No.
11/087,776
Filed
Mar 23, 2005
Granted
Jul 15, 2008
Kind
B2
Art Unit
1625
USPC
549/533
Abstract

Large crystals of titanium silicalite or intergrowths of intergrown smaller crystals, having a mean particle size greater than 2 μm, have been found catalytically effective at commercially reasonable rates for the epoxidation of olefins in the presence of hydrogen peroxide. Crystals synthesized with a silica source having a low sodium content exhibit high levels of production and selectivity. The crystals have a low attrition rate and are easily filterable from a product stream.

Claims (19)

1. A process for the preparation of a titanium silicalite catalyst comprising an intergrowth of titanium silicalite crystals having a mean particle size greater than 2 μm, said process comprising reacting a hydrolyzable titanium/silcon copolymer in the presence of a tetraalkylammonium hydroxide.

2. The process of claim 1 , wherein said tetraalkylammonium hydroxide comprises tetrapropylammonium hydroxide.

3. A process for the preparation of a titanium silicalite catalyst comprising an intergrowth of titanium silicalite crystals having a mean particle size greater than 2 μm, said process comprising reacting a hydrolyzable titanium/silcon copolymer in the presence of a tetraalkylammonium salt and a base.

4. The process of claim 3 , wherein said tetraalkylammonium salt is a tetrapropylammonium salt.

5. The process of claim 3 , wherein said salt is a halide.

6. The process of claim 3 , wherein said base comprises one or more of an organic amine, ammonia, or tetraalkylammonium hydroxide.

7. The process of claim 3 , wherein said hydrolyzable titanium/silicon copolymer comprises an alkyl silicate/titanate copolymer.

8. A process for the preparation of titanium silicalite olefin epoxidation catalysts of improved catalytic activity, said process comprising: a) preparing titanium silicalite crystals by crystal growth from a growth medium comprising a hydrolyzable titanium/silcon copolymer, an alkylammonium salt and a base to form a titanium silicalite product containing crystals or intergrowths thereof having a particle size greater than 2 μm; b) filtering the titanium silicalite product with a filter medium having a mean pore size greater than 0.5 μm; and c) recovering a filter cake of titanium silicalite crystals or intergrowths thereof relatively depleted of crystals or intergrowths having particle sizes less than 2 μm as compared with the amount of crystals or intergrowths with particle sizes less than 2 μm obtained in step a).

9. The process of claim 8 , wherein said base is an organic amine, ammonia, or a tetraalkylammonium hydroxide.

10. The process of claim 8 , wherein said alkylammonium salt is a tetrapropylammonium salt.

11. The process of claim 8 , wherein said filter medium has a mean pore size of from 1 μm to 8 μm.

12. The process of claim 8 , wherein said filter medium has a mean pore size of from 2 μm to 7 μm.

13. An olefin epoxidation catalyst suitable for epoxidation of olefins with an oxidant mixture comprising oxygen and hydrogen, prepared by a process comprising: treating a titanium silicalite catalyst produced by the process of claim 1 with a noble metal source to provide a titanium silicalite catalyst containing a noble metal such that hydrogen peroxide is generated in situ from hydrogen and oxygen.

14. The catalyst of claim 13 , wherein at least one noble metal is selected from the group consisting of palladium, gold, and platinum.

15. The catalyst of claim 13 , wherein said noble metal comprises palladium.

16. An olefin epoxidation catalyst suitable for epoxidation of olefins with an oxidant mixture comprising oxygen and hydrogen, prepared by a process comprising: treating a titanium silicalite catalyst catalyst produced by the process of claim 3 with a noble metal source to provide a titanium silicalite catalyst containing a noble metal such that hydrogen peroxide is generated in situ from hydrogen and oxygen.

17. The catalyst of claim 16 , wherein at least one noble metal is selected from the group consisting of palladium, gold, and platinum.

18. The catalyst of claim 16 , wherein said noble metal comprises palladium.

19. An olefin epoxidation catalyst suitable for epoxidation of olefins with an oxidant mixture comprising oxygen and hydrogen, prepared by a process comprising: treating a titanium silicalite catalyst prepared by the process of claim 8 with a noble metal source to provide a titanium silicalite catalyst containing a noble metal such that hydrogen peroxide is generated in situ from hydrogen and oxygen.

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: 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 →
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: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0856 →
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 →
Continuity (2)
Division 1025140500 · Sep 20, 2002
Related Publication 20050187395A1 · Aug 25, 2005