IP Library Granted Patent US 10,618,039
Granted Patent B2
US 10,618,039 · App. 16/201,241 · Granted Apr 14, 2020

Process and catalyst for the production of pyridine and alkyl derivatives thereof

Inventor: Dorai Ramprasad (Columbia, MD)
Assignee: W.R. GRACE & CO.-CONN.
B01J29/405B01J37/0045B01J37/08C07D213/09C07D213/10B01J2229/18B01J2229/20B01J2229/42
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Quick Facts
Patent No.
US 10,618,039
App. No.
16/201,241
Granted
Apr 14, 2020
Kind
B2
Abstract

A process for increasing the overall yield of pyridine or its alkyl pyridine derivatives during a base synthesis reaction is disclosed. The process comprises reacting a C 2 to C 5 aldehyde, a C 3 to C 5 ketone or a combination thereof, with ammonia and, optionally, formaldehyde, in the gas phase and in the presence of an effective amount of a particulate catalyst comprising a zeolite, zinc, a binder, and clay and optionally a matrix, wherein the catalyst has a L/B ratio of about 1.5 to about 4.0. Preferably, the zeolite is ZSM-5. A process for enhancing the catalytic activity of a zinc and zeolite containing catalyst to increase the overall yield of pyridine and/or its derivatives during a base synthesis reaction is also disclosed.

Claims (20)

1. A base synthesis process for the preparation of pyridine or its alkyl pyridine derivatives comprising reacting a C 2 to C 5 aldehyde, a C 3 to C 5 ketone or a combination thereof, with ammonia and, optionally, formaldehyde, in the gas phase and in the presence of an effective amount of a particulate catalyst comprising a zeolite selected from the group consisting of ZSM-5, ZSM-11 and combinations thereof, zinc, a binder and clay, wherein the catalyst has a L/B ratio of about 1.5 to about 4.0.

2. The process of claim 1 wherein the catalyst further comprises a matrix material.

3. The process of claim 1 wherein the zeolite is ZSM-5.

4. The process of claim 1 wherein the organic reactants are acetaldehyde and formaldehyde, and comprising the additional step of recovering pyridine and beta-picoline as the products of said process.

5. The process of claim 1 wherein the zeolite has been treated with a compound of zinc prior to incorporation into the catalyst composition.

6. The process of claim 1 wherein a compound of zinc is incorporated as a component of the catalyst during formulation of the catalyst composition.

7. The process of claim 1 wherein a compound of zinc is ion exchanged on preformed catalyst particles.

8. The process of claim 6 wherein the compound of zinc is selected from the group consisting of nitrate, halides, acetates and combinations thereof.

9. The process of claim 1 wherein the catalyst has an L/B ratio of about 2.0 to about 3.6.

10. The process of claim 1 wherein the binder is an alumina binder.

11. The process of claim 1 wherein the zeolite has a silica to alumina ratio of about 100 or less.

12. The process of claim 11 wherein the zeolite has a silica/alumina ratio of from about 20 to about 80.

13. The process of claim 3 wherein the zeolite has a silica/alumina ratio of about 28 to about 55.

14. The process of claim 1 wherein the zeolite is present in an amount ranging from about 35 wt % to about 50 wt % based on the total weight of the catalyst composition.

15. The process of claim 1 wherein the binder is present in an amount ranging from about 10 wt % to about 30 wt % based on the total weight of the catalyst composition.

16. The process of claim 1 wherein the clay component is present in an amount ranging from about 30 wt % to about 50 wt % based on the total weight of the catalyst composition.

17. The process of claim 1 wherein the particulate catalyst has a particle size sufficient for use in a fluid bed reactor.

18. The process of claim 17 wherein the particulate catalyst has a particle size ranging from about 40 μm to about 200 μm.

19. The process of claim 1 wherein the particulate catalyst has a Davison Index (DI) of less than 20.

20. The process of claim 1 wherein pyridine and beta-picoline are recovered as the products of said process.

Assignments (7)
NOTES SECURITY INTEREST Recorded Jan 29, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 074532/0229 →
SECURITY AGREEMENT (NOTES) Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 072520/0653 →
SECURITY INTEREST Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 072519/0240 →
SECURITY INTEREST Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 072519/0265 →
SECURITY INTEREST Recorded Apr 2, 2023
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 063199/0472 →
TERM LOAN SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 057594/0104 →
NOTES SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 057594/0156 →