Production system/production process for acrylic acid and precursors thereof

Patent metadata

Field	Value
Publication number	US-10703702-B2
Application number	US-201615223178-A
Country	US
Kind code	B2
Filing date	Jul 29, 2016
Priority date	Jul 31, 2015
Publication date	Jul 7, 2020
Grant date	Jul 7, 2020

Abstract

Provided herein are systems, and methods of using such systems, for producing acrylic acid from ethylene oxide and carbon monoxide on an industrial scale. The production system/production process has various unit operations, including, for example, a β-propiolactone production system/production process configured to produce β-propiolactone from ethylene oxide and carbon monoxide; a polypropiolactone production system/production process configured to produce polypropiolactone from β-propiolactone; and a glacial acrylic acid production system/production process configured to produce acrylic acid with a high purity by thermolysis of polypropiolactone.

First claim

What is claimed is:

1. A process for producing acrylic acid from a source of β-propiolactone, the process comprising:
contacting a β-propiolactone feed stream with a polymerization initiator in a polypropiolactone reaction zone having at least one polymerization reactor to produce a polypropiolactone outlet stream comprising polypropiolactone and β-propiolactone, wherein the at least one polymerization reactor is at least one of a continuous reactor or a semi-batch reactor; and
passing at least a portion of the polypropiolactone outlet stream to an acrylic acid production zone comprising a thermolysis reactor that receives the at least a portion of the polypropiolactone outlet stream to produce an acrylic acid stream comprising acrylic acid.

2. The process of claim 1 , wherein the polymerization initiator is selected from the group consisting of quaternary ammonium salts, alkali metal salts of carboxylic acids and phosphonium salts.

3. The process of claim 1 , wherein a radical polymerization inhibitor is present in the polypropiolactone reaction zone.

4. The process of claim 3 , wherein the radical polymerization inhibitor comprises phenothiazine in a concentration of 50-500 ppm (by weight).

5. The process of claim 1 , wherein the polypropiolactone reaction zone comprises a first polymerization reactor and a second polymerization reactor;
wherein the process further comprises:
producing a first mixture in the first polymerization reactor, wherein the first mixture comprises a first amount of the polypropiolactone, a first amount of unreacted β-propiolactone and a first amount of residual polymerization initiator; and
passing the first mixture and an additional amount of the polymerization initiator to the second polymerization reactor to produce at least a portion of the polypropiolactone outlet stream, wherein the at least a portion of the polypropiolactone outlet stream comprises a second amount of the polypropiolactone, a second amount of unreacted β-propiolactone, and a second amount of residual polymerization initiator.

6. The process of claim 5 , further comprising separating the second amount of unreacted β-propiolactone from the at least a portion of the polypropiolactone outlet stream in at least one of a flash tank evaporator, a wiped-film evaporator or a distillation apparatus.

7. The process of claim 1 , wherein the polypropiolactone outlet stream comprises solid polypropiolactone.

8. The process of claim 1 , wherein the acrylic acid production zone comprises at least one of: a thermolysis reactor in a form of a continuous stirred-tank reactor,
a plug flow reactor, a wiped film evaporator, a moving bed reactor; a kneader reactor; or
a fluidized bed reactor for receiving molten polypropiolactone.

9. The process of claim 1 , further comprising separating at least a portion of the acrylic acid stream into (i) an acrylic acid stream comprising acrylic acid having a purity of at least 90%, and (ii) an organic heavies stream.

10. A process for producing acrylic acid from ethylene oxide and carbon monoxide, comprising:
contacting input components comprising a carbon monoxide feed, an ethylene oxide feed, and a catalyst recycle stream with a carbonylation catalyst and a solvent in a carbonylation reaction zone and producing a β-propiolactone outlet stream comprising β-propiolactone, ethylene oxide and carbonylation catalyst;
passing at least a portion of the β-propiolactone outlet stream to a carbonylation catalyst recycling zone and separating said portion into i) a β-propiolactone separation stream comprising a portion of the β-propiolactone outlet stream from which at least some carbonylation catalyst has been removed and ii) the recycle stream, comprising β-propiolactone, solvent, ethylene oxide, carbonylation catalyst, succinic anhydride, and acetaldehyde;
passing at least a portion of the recycle stream to the carbonylation reaction zone;
purifying at least a portion of the β-propiolactone separation stream in a β-propiolactone purification zone comprising at least one separator, wherein the β-propiolactone purification zone produces a purified β-propiolactone stream and rejects a portion of at least one of β-propiolactone, solvent, ethylene oxide, carbonylation catalyst, succinic anhydride, and acetaldehyde in one or more rejection streams;
passing at least a portion of the purified β-propiolactone stream and a polymerization initiator to a polypropiolactone reaction zone having at least one polymerization reactor that produces a polypropiolactone outlet stream comprising polypropiolactone and β-propiolactone; and
passing at least a portion of the polypropiolactone outlet stream to an acrylic acid production zone comprising a thermolysis reactor that receives the at least a portion of the polypropiolactone outlet stream and produces an acrylic acid stream comprising acrylic acid.

11. The process of claim 10 , wherein the β-propiolactone purification zone produces an ethylene oxide rejection stream as one of the rejection streams,
wherein the ethylene oxide rejection stream comprises ethylene oxide, and at least a portion of the ethylene oxide rejection stream is passed to the carbonylation reaction zone.

12. The process of claim 11 , wherein the β-propiolactone purification zone produces a solvent recovery stream as one of the rejection streams, wherein the solvent recovery stream comprises solvent, and wherein at least a portion of the solvent recovery stream is passed to the carbonylation reaction zone.

13. The process of claim 10 , wherein:
I) the carbonylation catalyst recycling zone comprises one or more membrane systems from which the catalyst recycle stream is recovered as a retentate and β-propiolactone separation stream is recovered as a permeate; and
II) the β-propiolactone purification zone comprises
a.) an ethylene oxide recovery section comprising at least one distillation column that receives at least a portion of the β-propiolactone separation stream and produces an ethylene oxide stream containing ethylene oxide that is passed to the carbonylation reactor and a solvent bottoms stream containing solvent and β-propiolactone,
b.) a solvent recovery section comprising at least one distillation column that receives at least a portion of the solvent bottoms stream and produces an overhead recovered solvent stream comprising solvent that is passed to the carbonylation zone and a β-propiolactone bottoms stream comprising β-propiolactone, and
c.) a β-propiolactone concentration section comprising at least one distillation column that receives the β-propiolactone bottoms stream and produces a bottoms rejection stream and produces the purified β-propiolactone as an overhead stream.

14. The process of claim 10 , wherein at least one of the carbon monoxide feed and the ethylene oxide feed have at least one of an oxygen level of less than 5 ppm and a water level of less than 5 ppm.

15. The process of claim 10 , wherein the carbonylation catalyst is a cobalt-aluminum catalyst.

16. The process of claim 10 , wherein the carbonylation catalyst is at least partially dissolved in a catalyst solvent, and the catalyst solvent comprises an ether, a hydrocarbon, sulfolane, N-methyl pyrrolidone, 1,3 dimethyl-2-imidazolidinone, ethylene carbonate, propylene carbonate, butylene carbonate, dibasic esters, acetonitrile, ethyl acetate, propyl acetate, butyl acetate, 2-butanone, cyclohexanone, difluorobenzene, acetone, or methylethyl ketone, or any combination thereof.

17. The process of claim 10 , wherein the carbonylation reactor operates at a temperature from −20

Assignees

• Novomer Inc

Inventors

• Sookraj Sadesh H
• Farmer Jay J

Classifications

• C08G63/823

  for the preparation of polylactones or polylactides · CPC title

• C08G63/08 Primary

  Lactones or lactides · CPC title

• C07C51/12 Primary

  on an oxygen-containing group in organic compounds, e.g. alcohols · CPC title

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title

• C08G63/785

  characterised by the apparatus used · CPC title