INTEGRATED METHODS FOR CHEMICAL SYNTHESIS

• US 20170107103A1
• Filed: 05/29/2015
• Published: 04/20/2017
• Est. Priority Date: 05/30/2014
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: SLOWIK, Michael A., SOOKRAJ, Sadesh H.
• Granted Patent: US 10,597,294 B2
• Time in Patent Office: Days
• CPC Class Codes: B01J 2231/321 Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
• CPC Class Codes: B01J 2531/025 Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
• CPC Class Codes: B01J 2531/72 Manganese
• CPC Class Codes: B01J 2531/822 Rhodium
• CPC Class Codes: B01J 2531/827 Iridium
• CPC Class Codes: B01J 2531/842 Iron
• CPC Class Codes: B01J 2531/845 Cobalt
• CPC Class Codes: B01J 31/00 Catalysts comprising hydrides, coordination complexes or organic compounds catalyst compositions used only in polymerisation reactions C08 ; catalytic antibodies C12N9/0002
• CPC Class Codes: B01J 31/20 Carbonyls
• CPC Class Codes: C01B 2203/04 containing a purification step for the hydrogen or the synthesis gas
• CPC Class Codes: C01B 2203/0435 Catalytic purification
• CPC Class Codes: C01B 2203/062 Hydrocarbon production, e.g. Fischer-Tropsch process
• CPC Class Codes: C01B 2203/065 using hydrotreating, e.g. hydrogenation, hydrodesulfurisation
• CPC Class Codes: C01B 2203/066 with fuel cells
• CPC Class Codes: C01B 3/50 Separation of hydrogen or hydrogen containing gases from gaseous mixtures, e.g. purification C01B3/14 takes precedence
• CPC Class Codes: C07C 1/20 starting from organic compounds containing only oxygen atoms as heteroatoms
• CPC Class Codes: C07C 11/04 Ethylene
• CPC Class Codes: C07C 11/06 Propene
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 29/1518 one step being the formation of initial mixture of carbon oxides and hydrogen for synthesis
• CPC Class Codes: C07C 31/04 : Methanol
• 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 57/04 : Acrylic acid; Methacrylic acid
• CPC Class Codes: C07D 305/12 : Beta-lactones
• CPC Class Codes: C07D 307/60 : Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: C10G 2/30 : from carbon monoxide with hydrogen
• CPC Class Codes: C10G 2/32 : with the use of catalysts
• CPC Class Codes: H01M 8/0625 : in a modular combined reactor/fuel cell structure
• CPC Class Codes: H01M 8/0668 : Removal of carbon monoxide or carbon dioxide
• CPC Class Codes: Y02E 50/10 : Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02E 60/50 : Fuel cells
• CPC Class Codes: Y02P 20/10 : Process efficiency
• CPC Class Codes: Y02P 20/52 : using catalysts, e.g. selective catalysts
• CPC Class Codes: Y02P 30/20 : using bio-feedstock
• CPC Class Codes: Y02P 30/40 : Ethylene production

Abstract

Among other things, the present invention encompasses the applicant'"'"'s recognition that epoxide carbonylation can be performed industrially utilizing syngas streams containing hydrogen, carbon monoxide and varying amounts carbon dioxide. Contrary to expectation, the epoxide carbonylation reaction proceeds selectively in the presence of these mixed gas streams and incorporates excess CO in the syngas stream into valuable chemical precursors, resulting in hydrogen streams substantially free of CO. This is economically and environmentally preferable to performing WSGR which releases the excess carbon as CO2. The integrated processes herein therefore provide improved carbon efficiency for processes based on coal or biomass gasification or steam methane reforming.

Claims

1. A method for the integrated production of chemicals comprising the steps of:

a) in a first reaction zone, contacting an epoxide in the presence of a carbonylation catalyst with a syngas stream containing hydrogen and carbon monoxide thereby causing carbon monoxide in the industrial gas stream to react with the epoxide to provide an epoxide carbonylation product,

b) removing an upgraded gas stream from the first reaction zone wherein the upgraded gas stream has a higher hydrogen to carbon monoxide than the starting syngas stream,

c) in a second reaction zone, utilizing the upgraded gas stream to conduct a second chemical process requiring a hydrogen to CO ratio higher than the ratio in the industrial gas stream utilized in step (a).

2. The method of claim 1, wherein the syngas stream has a molar hydrogen to CO ratio between 0.5:

1 and 1.2;

1 and the upgraded gas stream has a hydrogen to CO ratio of at least 1.9;

1.

3. The method of claim 1, wherein the second chemical process comprises Fischer Tropsch synthesis.

4. The method of claim 1, wherein the second chemical process comprises reaction on a fuel cell.

5. The method of claim 1, wherein the second chemical process comprises hydrogenation.

6. The method of claim 1, wherein the epoxide carbonylation product is selected from the group consisting of:

optionally substituted beta lactone, optionally substituted succinic anhydride, and a polyester resulting from alternating polymerization of CO and the epoxide.

7. The method of claim 1, wherein the epoxide is ethylene oxide.

8. The method of claim 7, wherein the carbonylation product is beta propiolactone.

9. The method of claim 7, wherein the epoxide carbonylation product is succinic anhydride and the upgraded gas stream has a molar hydrogen to CO ratio greater than 5:

1.

10. The method of claim 9, wherein and the upgraded gas stream has a hydrogen to CO ratio greater than 10:

1, greater than 20;

1, greater than 50;

1, greater than 100;

1, or greater than 1,000;

1.

11. The method of claim 9, wherein the upgraded gas stream is substantially free of carbon monoxide.