Production system/production process for acrylic acid and precursors thereof

• US 10,703,702 B2
• Filed: 07/29/2016
• Issued: 07/07/2020
• Est. Priority Date: 07/31/2015
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Sookraj, Sadesh H, Farmer, Jay J.
• Primary Examiner(s): Kahn, Rachel
• Application Number:
  US15/223,178
• Publication Number:
  US 20170029352A1
• Time in Patent Office: 1,439 Days
• CPC Class Codes: B01J 19/1862 placed in series
• 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: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/785 characterised by the apparatus used
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

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.

Claims

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.

39. The process of claim 1, wherein the at least one polymerization reactor is at least one plug-flow reactor.

40. The process of claim 1, wherein the at least one polymerization reactor is at least one continuous-flow stirred-tank reactor.

41. The process of claim 1, wherein the at least one polymerization reactor is at least one loop reactor.

42. The process of claim 5, wherein the first polymerization reactor is at least one continuous-flow stirred-tank reactor or loop reactor, and the second polymerization reactor is at least one plug-flow reactor.

43. The process of claim 8, wherein the thermolysis reactor is the fluidized bed reactor for receiving molten polypropiolactone.

44. The process of claim 8, wherein the thermolysis reactor is the moving bed reactor.

45. The process of claim 1, wherein the at least one polymerization reactor is at least one of a continuous-flow stirred-tank reactor, a loop reactor, or a plug-flow reactor.

46. The process of claim 1, wherein the polymerization initiator is selected from the group consisting of ammonium acrylate, ammonium acetate, phosphonium acrylate, sodium acrylate, potassium acrylate, phosphonium acetate, tetra-n-butylammonium acrylate, sodium acetate, potassium acetate, tetra-n-butylammonium acetate, trimethylphenylammonium acrylate, trimethylphenylammonium acetate, and tetraphenyl phosphonium acrylate.

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°

C. to 160°

C. and operates at a pressure from 100 psig to 5000 psig, and produces β

-propiolactone with a selectivity of at least 90%.

18. The process of claim 10, wherein the carbonylation reaction zone contains at least one reactor selected from the group consisting of a continuous reactor or a semibatch reactor.

19. The process of claim 10, wherein the β

-propiolactone outlet stream satisfies on a mass fraction basis the condition of having;

at least 0.1 β

-propiolactone;

at most 0.9 solvent;

at most 0.07 ethylene oxide;

between 0.0005 to 0.04 of carbon monoxide;

at most 0.005 catalyst;

at most 0.07 acetaldehyde;

or at most 0.07 succinic anhydride.

20. The process of claim 10, wherein the β

-propiolactone outlet stream satisfies on a mass fraction basis the condition of having;

at least 0.1 and at most 0.4 β

-propiolactone;

at most 0.9 solvent;

at least 0.005 and at most 0.07 ethylene oxide;

between 0.0005 to 0.001 of carbon monoxide;

at least 0.0001 and at most 0.005 catalyst;

at least 0.0001 and at most 0.06 acetaldehyde;

or at least 0.0001 and at most 0.06 succinic anhydride.

21. The process of claim 10, wherein the carbonylation catalyst recycling zone comprises a membrane that is a ceramic membrane or a polymeric membrane, wherein the membrane has a carbonylation catalyst rejection rate greater than 95% or a permeability of greater than 1.0 L m−

2 hr−

1 bar−

1.

22. The process of claim 10, wherein the purifying of the β

-propiolactone separation stream in the β

-propiolactone purification zone is performed using a vacuum column, and the purified β

-propiolactone stream is recovered as a vacuum column overhead stream having a β

-propiolactone purity of at least 99%.

47. The process of claim 10, wherein the carbonylation catalyst is a carbonyl cobaltate in combination with an aluminum porphyrin compound, a carbonyl cobaltate in combination with an aluminum salen compound, a carbonyl cobaltate in combination with an aluminum salophen compound, or Al(TPP)Co(CO)4, or any combination thereof.

48. The process of claim 10, wherein the carbonylation catalyst is at least partially dissolved in a catalyst solvent, and the catalyst solvent comprises tetrahydrofuran, hexane, 2,5-dimethyl tetrahydrofuran, sulfolane, N-methyl pyrrolidone, 1,3 dimethyl-2-imidazolidinone, diglyme, triglyme, tetraglyme, diethylene glycol dibutyl ether, isosorbide ethers, methyl tertbutyl ether, diethylether, diphenyl ether, 1,4-dioxane, ethylene carbonate, propylene carbonate, butylene carbonate, dibasic esters, diethyl ether, acetonitrile, ethyl acetate, propyl acetate, butyl acetate, 2-butanone, cyclohexanone, toluene, difluorobenzene, dimethoxy ethane, acetone, or methylethyl ketone, or any combination thereof.

49. The process of claim 10, wherein the carbonylation reaction zone contains at least one reactor selected from the group consisting of a continuous-flow stirred-tank reactor, and a loop reactor.

23. A process for producing acrylic acid from ethylene oxide and carbon monoxide, comprising:

contacting carbon monoxide feed, an ethylene oxide feed, a carbon monoxide overhead stream and a β

-propiolactone recycle stream with a carbonylation catalyst and a solvent in a carbonylation reaction zone and producing a β

-propiolactone outlet stream comprising β

-propiolactone, solvent, ethylene oxide, carbon monoxide, carbonylation catalyst, acetaldehyde, and succinic anhydride;

passing at least a portion of the β

-propiolactone outlet stream to a carbon monoxide separator and recovering i.) the carbon monoxide separator overhead stream wherein the carbon monoxide separator overhead stream comprises ethylene oxide and carbon monoxide and ii.) a carbon monoxide separator bottoms stream comprising β

-propiolactone, solvent, carbonylation catalyst, acetaldehyde, succinic anhydride, and ethylene oxide;

passing at least a portion of the carbon monoxide separator overhead stream to the carbonylation reaction zone;

passing at least a portion the carbon monoxide separator bottoms stream to a membrane separation section of a carbonylation catalyst recycling zone and separating said at least a portion of the carbon monoxide separator bottoms stream into i) a β

-propiolactone recycle stream comprising a retentate containing separated carbonylation catalyst, solvent, and β

-propiolactone, and ii) a β

-propiolactone separation stream comprising a permeate containing β

-propiolactone, solvent, acetaldehyde, succinic anhydride, ethylene oxide and carbonylation catalyst;

passing at least a portion of the β

-propiolactone recycle stream to the carbonylation reaction zone;

passing at least a portion of the β

-propiolactone separation stream to a β

-propiolactone purification zone comprising at least one separation zone that separates the β

-propiolactone separation stream into a solvent recycle stream comprising solvent, and a purified β

-propiolactone stream comprising β

-propiolactone and carbonylation catalyst;

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 contacts the at least a portion of the purified β

-propiolactone stream with the polymerization initiator and produces a polypropiolactone outlet stream comprising polypropiolactone and β

-propiolactone;

passing at least a portion of the polypropiolactone outlet stream to a polypropiolactone/β

-propiolactone processing zone having at least one separation zone to produce i) a polypropiolactone/β

-propiolactone overhead stream that increases the concentration of β

-propiolactone relative to the polypropiolactone outlet stream, and ii) a polypropiolactone/β

-propiolactone separator bottoms stream that comprises polypropiolactone;

passing at least a portion of the polypropiolactone/β

-propiolactone overhead stream to the polypropiolactone reaction zone;

passing at least a portion of the polypropiolactone/β

-propiolactone bottoms stream to an acrylic acid production zone comprising a thermolysis reactor that receives the at least a portion of the a polypropiolactone outlet stream and produces an acrylic acid stream; and

separating at least a portion of the acrylic acid stream in a separator into (i) acrylic acid stream comprising acrylic acid having a purity of at least 90%, and (ii) an organic heavies stream.

24. The process of claim 23, wherein the acrylic acid stream has an acrylic acid purity of greater than 99.5% and comprises glacial acrylic acid.

25. The process of claim 23, wherein the at least one polymerization reactor produces polypropiolactone at a polypropiolactone conversion of at least 50%.

26. The process of claim 23, wherein the at least one separation zone in the polypropiolactone/β

-propiolactone processing zone comprises at least one flash tank, or at least one evaporator, or a combination thereof.

27. The process of claim 26, wherein the at least one evaporator is at least one wiped film evaporator, thin film evaporator, or falling film evaporator.

28. The process of claim 23, wherein the carbonylation reactor zone operates at a temperature between 30°

C. and 160°

C., and a pressure between 100 psig and 5000 psig.

29. The process of claim 23, wherein the carbon monoxide separator is a flash tank.

30. The process of claim 23, wherein the membrane separation section comprises at least one membrane selected from the group consisting of ceramic membranes and polymeric membranes, wherein the at least one membrane has a rejection rate of greater than 95% or a permeability of greater than 1.0 1.0 L m−

2 hr−

1 bar−

1.

31. The process of claim 23, wherein the at least one separation zone comprises a distillation column that operates at or below atmospheric pressure and at a temperature of less than 120°

C.

32. The process of claim 23, wherein the solvent recycle stream comprises solvent, and the solvent recycle stream has less than 15 wt % of β

-propiolactone, ethylene oxide, carbon monoxide, acetaldehyde, or succinic anhydride.

33. The process of claim 23, wherein the purified β

propiolactone stream comprises (i) β

-propiolactone and (ii) less than 1 wt % of solvent, ethylene oxide, carbon monoxide, acetaldehyde, or succinic anhydride.

34. A process for producing glacial acrylic acid from ethylene oxide and carbon monoxide, comprising:

contacting carbon monoxide feed, an ethylene oxide feed, a carbon monoxide overhead stream and a β

-propiolactone recycle stream with a carbonylation catalyst and a solvent in a carbonylation reaction zone and producing a β

-propiolactone outlet stream comprising β

-propiolactone, solvent, ethylene oxide, carbon monoxide, carbonylation catalyst, acetaldehyde,

and succinic anhydride;

passing at least a portion of the β

-propiolactone outlet stream to a carbon monoxide separator and recovering i.) the carbon monoxide overhead stream wherein the carbon monoxide overhead stream comprises ethylene oxide and carbon monoxide and ii.) a carbon monoxide bottoms stream comprising β

-propiolactone, solvent, carbonylation catalyst, acetaldehyde, succinic anhydride, ethylene oxide and carbon monoxide;

passing at least a portion of the carbon monoxide overhead stream to the carbonylation reaction zone;

passing at least a portion the carbon monoxide bottoms stream to a membrane separation section of a carbonylation catalyst recycling zone and separating said at least a portion of the carbon monoxide bottoms stream into i) a β

-propiolactone recycle stream comprising a retentate containing separated carbonylation catalyst, solvent and β

-propiolactone and ii) a β

-propiolactone separation stream comprising a permeate containing β

-propiolactone, solvent,

acetaldehyde, succinic anhydride, ethylene oxide, carbon monoxide, and carbonylation catalyst;

passing at least a portion of the β

-propiolactone recycle stream to the carbonylation reaction zone;

purifying the β

-propiolactone separation stream in a β

-propiolactone purification zone comprising at least one distillation column that further separates the β

-propiolactone separation stream into a solvent recycle stream comprising solvent and a purified β

-propiolactone stream comprising β

-propiolactone;

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 contacts the at least a portion of the purified β

-propiolactone stream with the polymerization initiator and produces a polypropiolactone outlet stream comprising polypropiolactone and β

-propiolactone;

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; and

separating at least a portion of the acrylic acid stream in a condenser into (i) an acrylic acid stream comprises acrylic acid having a purity of at least 90%, and (ii) an organic heavies stream.

35. The process of claim 34, wherein the acrylic acid stream has an acrylic acid purity of greater than 99.5%, and wherein the acrylic acid stream comprises glacial acrylic acid.

36. The process of claim 34, wherein the at least a portion of the polypropiolactone outlet stream that passes to the acrylic acid production zone first passes to a polypropiolactone purification zone, wherein the polypropiolactone purification zone comprises a polypropiolactone ion exchange zone comprising a resin column that a.) purifies the at least a portion of the polypropiolactone outlet stream that passes to the acrylic acid production zone so that the polypropiolactone outlet stream comprises at least 90 wt % of polypropiolactone, and b.) removes an ionic species stream comprising cationic carbonylation catalyst species and anionic carbonylation catalyst species.

37. The process of claim 34, wherein at least a portion of the polypropiolactone outlet stream that passes to the acrylic acid production zone from the polypropiolactone purification zone first passes to a polypropiolactone processing zone before passing to the acrylic acid production zone, and the polypropiolactone processing zone converts the at least a portion of the polypropiolactone outlet stream that passes to the acrylic acid production zone to solid form.

38. The process of claim 34, wherein:

a.) at least a portion of the polypropiolactone outlet stream that passes to the acrylic acid production zone passes from the polypropiolactone purification zone to a polypropiolactone/β

-propiolactone processing zone before passing to the acrylic acid production zone and the a polypropiolactone/β

-propiolactone processing zone has at least one separation zone to produce i.) an overhead stream that increases the concentration of β

-propiolactone in the at least a portion of the polypropiolactone outlet stream that passes to the acrylic acid production zone and ii.) a polypropiolactone/β

-propiolactone bottoms stream that comprises polypropiolactone; and

b.) a condensate ion exchange zone comprising a resin column receives at least a portion of the organic heavies and separates the organic heavies into a heavies output stream and an ionic species stream comprising cationic carbonylation catalyst species and anionic carbonylation catalyst species.