FLEXIBLE CHEMICAL PRODUCTION PLATFORM

• US 20180029005A1
• Filed: 02/12/2016
• Published: 02/01/2018
• Est. Priority Date: 02/13/2015
• Status: Abandoned Application

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: SOOKRAJ, Sadesh H.
• Application Number:
  US15/550,153
• Publication Number:
  US 20180029005A1
• Time in Patent Office: Days
• CPC Class Codes: B01J 19/0006 Controlling or regulating processes controlling or regulating in general G05
• CPC Class Codes: B01J 19/2445 placed in parallel
• CPC Class Codes: B01J 19/245 placed in series
• CPC Class Codes: B01J 2219/00049 Controlling or regulating processes
• CPC Class Codes: B01J 2219/24 Stationary reactors without moving elements inside
• CPC Class Codes: C07C 29/132 by reduction of an oxygen containing functional group
• CPC Class Codes: C07C 29/147 of carboxylic acids or derivatives thereof
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 31/207 1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 55/10 Succinic acid
• CPC Class Codes: C07C 57/04 Acrylic acid; Methacrylic acid
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters
• CPC Class Codes: C07D 301/03 by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 307/08 Preparation of tetrahydrofuran
• CPC Class Codes: C07D 307/33 in position 2, the oxygen atom being in its keto or unsubstituted enol form
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/78 : Preparation processes
• CPC Class Codes: C08G 63/785 : characterised by the apparatus used
• CPC Class Codes: C08J 11/12 : by dry-heat treatment only
• CPC Class Codes: C08J 2367/04 : Polyesters derived from hydroxy carboxylic acids, e.g. lactones C08J2367/06 takes precedence

Abstract

Disclosed are integrated systems and methods for the conversion of epoxides to beta lactones and to multiple C₃ products and/or C₄ products.

Claims

1. A system for the production of C₃ and C₄ products, comprising:

an epoxide source;

a carbon monoxide (CO) source;

a central reactor, comprising;

an inlet configured to receive epoxide from the epoxide source and CO from the CO source,

a central reaction zone configured to convert at least some of the epoxide to a beta lactone, and

an outlet configured to provide an outlet stream comprising the beta lactone,

two or more of (i)-(iii);

(i) a first C₃ reactor, comprising;

an inlet configured to receive the outlet stream comprising beta lactone of the central reactor,

a first C₃ reaction zone configured to convert at least some of the beta lactone to a first C₃ product, and

an outlet configured to provide an outlet stream comprising the first C₃ product,

(ii) a second C₃ reactor, comprising;

an inlet configured to receive the outlet stream comprising beta lactone of the central reactor,

a second C₃ reaction zone configured to convert at least some of the beta lactone to a second C₃ product, and

an outlet configured to provide an outlet stream comprising the second C₃ product, and

(iii) a first C₄ reactor, comprising;

an inlet configured to receive the outlet stream comprising beta lactone of the central reactor,

a first C₄ reaction zone configured to convert at least some of the beta lactone to a first C₄ product, and

an outlet configured to provide an outlet stream comprising the first C₄ product, and

a controller to independently modulate production of the beta lactone and each of the products,

provided that the first C₃ product differs from the second C₃ product.

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

3. The system of claim 1, further comprising;

an ethylene source;

an oxidative reactor comprising;

an inlet configured to receive ethylene,

an oxidative reaction zone configured to convert at least some of the ethylene to EO, and

an outlet configured to provide an outlet stream comprising the EO, and feed the outlet stream comprising EO to the inlet of the central reactor.

4. The system of claim 1, wherein the first C₃ product and the second C₃ product are independently selected from an α

,β

-unsaturated acid, an α

,β

-unsaturated ester, an α

,β

-unsaturated amide, a polymer and 1,3-propanediol (PDO).

5. The system of claim 1, wherein the first C₃ product is PPL, and the system further comprises:

a third C₃ reactor comprising;

an inlet configured to receive the outlet stream comprising PPL of the first C₃ reactor,

a third C₃ reaction zone configured to convert at least some of the PPL to a third C₃ product, and

an outlet configured to provide an outlet stream comprising the third C₃ product.

6. The system of claim 5, wherein the third C₃ product is acrylic acid (AA).

7. The system of claim 1, wherein the first C₄ product is succinic anhydride, and the system further comprises:

a second C₄ reactor comprising;

an inlet configured to receive the outlet stream comprising succinic anhydride of the first C₄ reactor,

a second C₄ reaction zone configured to convert at least some of the succinic anhydride to a second C₄ product, and

an outlet configured to provide an outlet stream comprising the second C₄ product.

8. The system of claim 7, wherein the second C₄ product is succinic acid, 1,4 butanediol (BDO), tetrahydrofuran (THF) or gamma butyrolactone (GBL).

9. A system, comprising:

an ethylene source;

a carbon monoxide (CO) source;

an alcohol source;

an oxidative reactor comprising;

an inlet configured to receive ethylene from the ethylene source,

an oxidative reaction zone configured to convert at least some of the ethylene to ethylene oxide (EO), and

an outlet configured to provide an EO stream comprising the EO;

a central reactor comprising;

an inlet configured to receive EO from the EO stream of the oxidative reactor and CO from the CO source,

a central reaction zone configured to convert at least some of the EO to beta propiolactone (BPL), and

an outlet configured to provide a BPL stream comprising the BPL;

a first C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor,

a first C3 reaction zone configured to convert at least some of the BPL to a polypropiolactone (PPL), and

an outlet configured to provide a PPL stream comprising the PPL;

a second C3 reactor comprising;

an inlet configured to receive PPL from the PPL stream of the first C3 reactor,

a second C3 reaction zone configured to convert at least some of the PPL to AA, and

an outlet configured to provide an AA stream comprising the AA;

a third C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor, and an alcohol from the alcohol source,

a third C3 reaction zone configured to convert at least some of the BPL to acrylate esters, and

an outlet configured to provide an acrylate ester stream comprising the acrylate esters; and

a controller to independently modulating production of the EO, BPL, PPL, AA, and acrylate esters.

10. A system, comprising:

an ethylene source;

a carbon monoxide (CO) source;

an alcohol source;

an oxidative reactor comprising;

an inlet configured to receive ethylene from the ethylene source,

an oxidative reaction zone configured to convert at least some of the ethylene to ethylene oxide (EO), and

an outlet configured to provide an EO stream comprising the EO;

a central reactor comprising;

an inlet configured to receive EO from the EO stream of the oxidative reactor and CO from the CO source,

a central reaction zone configured to convert at least some of the EO to beta propiolactone (BPL), and

an outlet configured to provide a BPL stream comprising the BPL;

a first C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor,

a first C3 reaction zone configured to convert at least some of the BPL to a polypropiolactone (PPL), and

an outlet configured to provide a PPL stream comprising the PPL;

a second C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor,

a second C3 reaction zone configured to convert at least some of the BPL to AA, and

an outlet configured to provide an AA stream comprising the AA;

a third C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor, and an alcohol from the alcohol source,

a third C3 reaction zone configured to convert at least some of the BPL to acrylate esters, and

an outlet configured to provide an acrylate ester stream comprising the acrylate esters; and

a controller to independently modulating production of the EO, BPL, PPL, AA, and acrylate esters.

11. A system, comprising:

an ethylene source;

a carbon monoxide (CO) source;

an oxidative reactor comprising;

an inlet configured to receive ethylene from the ethylene source,

an oxidative reaction zone configured to convert at least some of the ethylene to ethylene oxide (EO), and

an outlet configured to provide an EO stream comprising the EO;

a central reactor comprising;

an inlet configured to receive EO from the EO stream of the oxidative reactor and CO from the CO source,

a central reaction zone configured to convert at least some of the EO to beta propiolactone (BPL), and

an outlet configured to provide a BPL stream comprising the BPL;

a first C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor,

a first C3 reaction zone configured to convert at least some of the BPL to a polypropiolactone (PPL), and

an outlet configured to provide a PPL stream comprising the PPL;

a second C3 reactor comprising;

an inlet configured to receive PPL from the PPL stream of the first C3 reactor,

a second C3 reaction zone configured to convert at least some of the PPL to AA, and

an outlet configured to provide an AA stream comprising the AA;

a first C4 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor, and carbon monoxide from the CO source,

a first C4 reaction zone configured to convert at least some of the BPL to succinic anhydride (SA), and

an outlet configured to provide a succinic anhydride stream comprising the succinic anhydride; and

a controller to independently modulating production of the EO, BPL, PPL, AA, and SA.

13. The system of claim 11, further comprising:

a hydrogen source; and

a second C4 reactor comprising;

an inlet configured to receive SA from the SA stream of the first C4 reactor,

a hydrogen inlet fed from the hydrogen source,

a second C4 reaction zone configured to hydrogenate at least a portion of the SA to provide a C4 product stream comprising 1,4 butanediol (BDO), tetrahydrofuran (THF), or gamma butyrolactone (GBL), or any combinations thereof.

14. The system of claim 13, wherein the controller is configured to further modulate production of BDO, THF, and GBL.

12. A system, comprising:

an ethylene source;

a carbon monoxide (CO) source;

an alcohol source;

an oxidative reactor comprising;

an inlet configured to receive ethylene from the ethylene source,

an oxidative reaction zone configured to convert at least some of the ethylene to ethylene oxide (EO), and

an outlet configured to provide an EO stream comprising the EO,

a central reactor comprising;

an inlet configured to receive EO from the EO stream of the oxidative reactor and at least a portion of CO from the CO source,

a central reaction zone configured to convert at least some of the EO to beta propiolactone (BPL), and

an outlet configured to provide a BPL stream comprising the BPL;

a first C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor,

a first C3 reaction zone configured to convert at least some of the BPL to a polypropiolactone (PPL), and

an outlet configured to provide a PPL stream comprising the PPL;

a second C3 reactor comprising;

an inlet configured to receive BPL from the BPL stream of the central reactor,

a second C3 reaction zone configured to convert at least some of the BPL to AA, and

an outlet configured to provide an AA stream comprising the AA;

a third C3 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor, and an alcohol from the alcohol source,

a third C3 reaction zone configured to convert at least some of the BPL to acrylate esters, and

an outlet configured to provide an acrylate ester stream comprising the acrylate esters;

a first C4 reactor comprising;

an inlet configured to receive BPL from at least a portion of the BPL stream of the central reactor, and at least a portion of CO from the CO source,

a first C4 reaction zone configured to convert at least some of the BPL to succinic anhydride (SA), and

an outlet configured to provide a SA stream comprising the succinic anhydride; and

a controller to independently modulating production of the EO, BPL, PPL, AA, acrylate esters, and SA.

15. A method for converting an epoxide to two or more of:

a first C₃ product, a second C₃ product, and a first C₄ 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 C₃ reactor, and converting at least some of the beta lactone to a first C₃ product in the first C₃ reactor to produce an outlet stream comprising the first C₃ product, or

(ii) directing the outlet stream comprising beta lactone from the central reaction zone to a second C₃ reactor, and converting at least some of the beta lactone to a second C₃ product in the second C₃ reactor to produce an outlet stream comprising the second C₃ product, or

(iii) directing the outlet stream comprising beta lactone from the central reaction zone to a first C₄ reactor, and converting at least some of the beta lactone to a first C₄ product in the first C₄ reactor to produce an outlet stream comprising the first C₄ product,

provided that at least two of (i)-(iii) are selected; and

obtaining two or more of the first C₃ product, the second C₃ product, and the first C₄ product.

16. 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);

and at least one or both of (i) and (ii);

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

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

17. The method of claim 16, 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).

18. 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.

19. 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 at least a portion of the BPL stream to a second C3 reactor;

converting at least a portion of the BPL 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 with an alcohol in the third C3 reactor; 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.

20. 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 some 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 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.

22. The method claim 20, 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.

21. 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 at least a portion of 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 at least a portion of the BPL stream to a second C3 reactor;

converting at least a portion of the BPL 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 with an alcohol in the third C3 reactor;

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