# US 11,078,172 B2 · Integrated methods for chemical synthesis

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- Number: US 11,078,172 B2
- Document ID: US11078172B2
- Status: Granted
- Kind: B2
- Application number: 16/453,775
- Filed: 2019-06-26
- Published: 2019-10-17
- Granted: 2021-08-03
- Earliest claimed: 2015-02-13
- Assignees: Novomer, Inc.
- Applicants: Novomer, Inc.
- Inventors: Sadesh H. Sookraj; Michael A. Slowik
- Web page: https://patentgrep.com/patent/US11078172B2

## CPC

- C07D 305/12: Beta-lactones
- C01B 3/32: by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide or air
- C01B 3/34: by reaction of hydrocarbons with gasifying agents
- C01B 3/50: Separation of hydrogen or hydrogen-containing gases from gaseous mixtures, e.g. purification
- C07D 307/60: Two oxygen atoms, e.g. succinic anhydride
- C10G 2/30: {from carbon monoxide with hydrogen}
- C01B 2203/062: Hydrocarbon production, e.g. Fischer-Tropsch process
- C01B 2203/066: with fuel cells
- C01B 2203/068: Ammonia synthesis
- C10J 2300/1656: Conversion of synthesis gas to chemicals
- Y02E 50/30: Fuel from waste, e.g. synthetic alcohol or diesel
- Y02P 20/10: Process efficiency
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10J: PRODUCTION OF PRODUCER GAS, WATER-GAS, SYNTHESIS GAS FROM SOLID CARBONACEOUS MATERIAL, OR MIXTURES CONTAINING THESE GASES (synthesis gas from liquid or gaseous hydrocarbons C01B; underground gasification of minerals E21B43/295); CARBURETTING AIR OR OTHER GASES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The integrated processes herein provide improved carbon efficiency for processes based on coal or biomass gasification or steam methane reforming. Provided are also ethylene oxide carbonylation products such as beta-propiolactone and succinic anhydride having a bio-based content between 0% and 100%, and methods for producing and analyzing the same.

## Claims

### Claim 1

A method comprising:
a) selecting a target bio-based content for beta-propiolactone;
b) combining a bio-based ethylene oxide stream and a fossil-based ethylene oxide stream to produce a combined ethylene oxide feed stream; and
c) carbonylating the combined ethylene oxide feed stream using the combined carbon monoxide feed stream in the presence of carbonylation catalyst to produce beta-propiolactone having the target bio-based content selected in step (a).

### Claim 2 (depends on 1)

The method of claim 1, wherein the bio-based ethylene oxide stream is produced by a process comprising biomass fermentation.

### Claim 3 (depends on 1)

The method of claim 1, wherein the bio-based ethylene oxide stream is produced by a process comprising biomass gasification.

### Claim 4 (depends on 3)

The method of claim 3, wherein the biomass gasification is municipal solid waste gasification.

### Claim 5 (depends on 1)

The method of claim 1, wherein the fossil-based ethylene oxide stream is prepared by:
cracking the fossil-based feedstock to produce ethylene; and
oxidizing the ethylene to produce the fossil-based ethylene oxide stream.

### Claim 6 (depends on 1)

The method of claim 1, wherein the fossil-based feedstock comprises naphtha, shale gas, oil, or coal, or any combination thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein the bio-based syngas stream is prepared by:
performing biomass gasification to produce methanol, and
processing the methanol to produce the bio-based syngas stream.

### Claim 8 (depends on 1)

The method of claim 1, wherein the bio-based ethylene oxide stream is produced by electrolysis of carbon dioxide to produce the bio-based carbon monoxide stream.

### Claim 9 (depends on 1)

The method of claim 1, wherein the fossil-based syngas stream has a H2 to CO ratio in the range from 0.4:1 to 1.2:1.

### Claim 10 (depends on 1)

The method of claim 1, wherein the carbonylating of the combined ethylene oxide feed stream using the combined carbon monoxide feed stream further produces an upgraded syngas stream having a higher H2 to CO ratio than the combined carbon monoxide feed stream.

### Claim 11 (depends on 10)

The method of claim 10, further comprising feeding the upgraded syngas stream to a Fischer Tropsch reactor to produce liquid fuels, oils, waxes, olefins, or alcohols, or any combination thereof.

### Claim 12 (depends on 11)

The method of claim 11, further comprising treating the upgraded syngas stream to remove residual solvent, residual ethylene oxide, or residual carbon dioxide, or any combination thereof, prior to feeding the upgraded syngas stream to the Fischer Tropsch reactor.
