IP Library Granted Patent US 11,420,177
Granted Patent B2
US 11,420,177 · App. 16/890,056 · Granted Aug 23, 2022

Flexible chemical production method

Inventor: Sadesh H. Sookraj (Rochester, NY)
Assignee: Novomer, Inc.
B01J19/2445B01J19/0006B01J19/245C07C29/132C07C29/147C07C29/149C07C51/09C07C67/03C07D301/03C07D305/12C07D307/08C07D307/33C07D307/60C08G63/08C08G63/78C08G63/785C08J11/12B01J2219/00049B01J2219/24C08J2367/04
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Quick Facts
Patent No.
US 11,420,177
App. No.
16/890,056
Granted
Aug 23, 2022
Kind
B2
Abstract

Disclosed herein is a method for converting an epoxide to a first C3 product, a second C3 product, and/or a first C4 product within an integrated system. The method includes converting the epoxide to a beta lactone to produce an outlet stream comprising beta lactone. The method includes converting the beta lactone of the outlet stream to a first C3 product in the first C3 reactor to produce an outlet stream comprising the first C3 product; converting the beta lactone to a second C3 product in the second C3 reactor to produce an outlet stream comprising the second C3 product, and/or converting the beta lactone to a first C4 product in the first C4 reactor to produce an outlet stream comprising the first C4 product.

Claims (61)

1. A method for converting an epoxide to two or more of: a first C 3 product, a second C 3 product, and a first C 4 product within an integrated system, the method comprising:

providing an inlet stream comprising an epoxide and carbon monoxide (CO) to a central reactor of the integrated system;

contacting the inlet stream with a carbonylation catalyst in a central reaction zone;

converting at least a portion of the epoxide to a beta lactone to produce an outlet stream comprising beta lactone;

(i) directing the outlet stream comprising beta lactone from the central reaction zone to a first C 3 reactor, and converting at least some of the beta lactone to a first C 3 product in the first C 3 reactor to produce an outlet stream comprising the first C 3 product, or

(ii) directing the outlet stream comprising beta lactone from the central reaction zone to a second C 3 reactor, and converting at least some of the beta lactone to a second C 3 product in the second C 3 reactor to produce an outlet stream comprising the second C 3 product, and

(iii) directing the outlet stream comprising beta lactone from the central reaction zone to a first C 4 reactor, and converting at least some of the beta lactone to a first C 4 product in the first C 4 reactor to produce an outlet stream comprising the first C 4 product; and

obtaining the first C 3 product, the second C 3 product, and the first C 4 product.

2. A method for producing acrylic acid (AA) from ethylene in a single integrated system, the method comprising:

providing ethylene to an oxidative reactor that converts at least some of the ethylene to ethylene oxide (EO);

providing EO to a central reactor that converts at least some of the EO to beta propiolactone (BPL);

providing BPL to a first reactor that converts at least some of the BPL to AA, and

providing BPL to a second reactor that converts at least some of the BPL to polypropiolactone (PPL).

3. The method of claim 2 , wherein BPL is provided to a first reactor that converts at least some of the BPL, and the method further comprises isolating acrylic acid at a rate of about 200 to about 800 kilotons per annum (kta).

4. A method, comprising:

providing an EO stream and a CO stream to a central reactor, wherein the EO stream comprises EO, and the CO stream comprises CO;

contacting the EO stream and the CO stream with a carbonylation catalyst in the central reactor;

converting at least a portion of the EO to produce a beta propiolactone (BPL) stream comprising BPL;

directing at least a portion of the BPL stream to a first C3 reactor;

converting at least portion of the BPL to polypropiolactone (PPL) in the first C3 reactor, to produce a PPL stream comprising the PPL from the first C3 reactor;

directing the PPL stream to a second C3 reactor;

converting at least a portion of the PPL to acrylic acid (AA) in the second C3 reactor, to produce an AA stream comprising the AA from the second C3 reactor;

directing at least a portion of the BPL stream to a third C3 reactor;

contacting the BPL stream in the third C3 reactor with an alcohol; and

converting at least a portion of the BPL to acrylate esters in the third C3 reactor, to produce an acrylate ester stream comprising the acrylate esters.

5. The method of claim 4 , further comprising:

directing at least a portion of the BPL stream to a fourth C3 reactor;

converting at least a portion of the BPL to acrylic acid (AA) in the fourth C3 reactor, to produce an AA stream comprising the AA from the fourth C3 reactor;

directing at least a portion of the BPL stream to a fifth C3 reactor;

contacting the BPL stream with an alcohol in the fifth C3 reactor; and

converting at least a portion of the BPL to acrylate esters in the fifth C3 reactor, to produce another acrylate ester stream comprising the acrylate esters.

6. The method of claim 4 , further comprising:

directing at least a portion of the BPL stream to a first C4 reactor; and

converting at least some of the BPL to succinic anhydride (SA) in the first C4 reactor, to produce a succinic anhydride stream comprising the succinic anhydride from the first C4 reactor.

7. The method of claim 4 , further comprising:

directing at least a portion of the BPL stream to a fourth C3 reactor;

contacting the BPL stream with an alcohol in the fourth C3 reactor;

converting at least a portion of the BPL to acrylate esters in the fourth C3 reactor, to produce another acrylate ester stream comprising the acrylate esters;

directing at least a portion of the BPL stream to a first C4 reactor;

contacting the BPL stream and at least a portion of the CO stream in the first C4 reactor; and

converting at least a portion of the BPL to succinic anhydride (SA) in the first C4 reactor, to produce a SA stream comprising the SA.

8. The method of claim 6 , further comprising:

directing the SA stream to a second C4 reactor;

contacting at the SA stream with hydrogen in the second C4 reactor; and

converting at least a portion of the SA to 1,4 butanediol (BDO), tetrahydrofuran (THF), or gamma butyrolactone (GBL), or any combinations thereof.

9. The method of claim 1 , further comprising:

providing an inlet stream comprising ethylene to an inlet of an oxidative reactor;

converting at least some of the ethylene to ethylene oxide (EO) to produce an outlet stream comprising EO;

directing the outlet stream comprising EO from the oxidative reactor to the inlet of the central reactor; and

converting at least some of the EO to BPL.

10. The method of claim 1 , wherein the outlet stream comprising beta lactone is directed from the central reaction zone to the first C3 reactor and the first C4 reactor.

11. The method of claim 1 , wherein the epoxide is ethylene oxide (EO) and the beta lactone is beta propiolactone (BPL).

12. The method of claim 4 , wherein the PPL stream, the AA stream, and the acrylate ester stream are simultaneously produced.

13. The method of claim 4 , further comprising modulating a ratio of PPL:AA:acrylate ester produced in the PPL stream, the AA stream, and the acrylate ester stream.

14. The method of claim 4 , further comprising modulating the fraction of the PPL stream that is received by the second C3 reactor.

15. The method of claim 5 , wherein two or more of the PPL stream, the AA stream, and the acrylate ester stream are simultaneously produced.

16. The method of claim 6 , further comprising modulating the fraction of the PPL stream that is received by the second C3 reactor.

17. The method of claim 8 , further comprising modulating a ratio of BDO:THF:GBL produced in the second C4 reactor.

18. The method of claim 6 , wherein the PPL stream, the AA stream, and the SA stream are simultaneously produced.

19. The method of claim 6 , further comprising modulating a ratio of PPL:AA:SA from the PPL stream, the AA stream, and the SA stream.

20. The method of claim 1 , wherein the first C 3 product includes polypropiolactone, wherein the second C 3 product includes polyacrylic acid, and wherein the first C 4 product includes tetrahydrofuran and/or gamma butyrolactone.

Assignments (4)
CHANGE OF NAME Recorded Mar 24, 2026
From: NMER WINDDOWN, INC.
To: NOVOMER LLC
Reel/Frame 075187/0876 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2022
From: TRUIST BANK
To: NOVOMER, INC.
Reel/Frame 061088/0116 →
SECURITY INTEREST Recorded Feb 1, 2022
From: NOVOMER, INC.
To: TRUIST BANK
Reel/Frame 058922/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2021
From: SOOKRAJ, SADESH H.
To: NOVOMER, INC.
Reel/Frame 056876/0326 →
Continuity (3)
Division 15550153
Provisional Application 62116234 · Feb 13, 2015
Related Publication 20200298199A1 · Sep 24, 2020