Purification of biologically-produced 1,3-propanediol

• US 20050069997A1
• Filed: 05/05/2004
• Published: 03/31/2005
• Est. Priority Date: 05/06/2003
• Status: Active Grant

• Current Assignee: DuPont Industrial Biosciences USA, LLC (DuPont de Nemours, Inc.)
• Original Assignee: TATE & LYLE Ingredients Americas LLC (TATE & LYLE PLC)
• Inventors: Seapan, Mayis, Trotter, Robert E., Chu, Luis Alberto, Gaddy, James M., Alsop, Albert W., Adkesson, Dennis Michael, Fitzgibbon, Patrick, Disney, James M., Ames, Tyler T., Lievense, Jefferson C., Wenndt, Gregory M., Gallagher, F. Glenn, Luyben, Michael L., Yu, Eugene K., Dravis, Bryan C., Lehnhardt, William F.
• Granted Patent: US 7,919,658 B2
• Time in Patent Office: Days
• US Class Current: 435/158
• CPC Class Codes: B01D 2311/04 Specific process operations in the feed stream; Feed pretreatment
• CPC Class Codes: B01D 2311/2623 Ion-Exchange
• CPC Class Codes: B01D 3/002 by continuous methods
• CPC Class Codes: B01D 3/143 by two or more of a fractionation, separation or rectification step
• CPC Class Codes: B01D 3/145 One step being separation by permeation
• CPC Class Codes: B01D 61/027 Nanofiltration
• CPC Class Codes: B01D 61/04 Feed pretreatment
• CPC Class Codes: B01D 61/145 Ultrafiltration
• CPC Class Codes: B01D 61/146 comprising multiple ultrafiltration steps
• CPC Class Codes: B01D 61/147 Microfiltration
• CPC Class Codes: B01D 61/1471 comprising multiple microfiltration steps
• CPC Class Codes: B01D 61/149 Multistep processes comprising different kinds of membrane processes selected from ultrafiltration or microfiltration
• CPC Class Codes: B01D 61/58 Multistep processes
• CPC Class Codes: C07C 29/76 by physical treatment
• CPC Class Codes: C07C 29/80 by distillation
• CPC Class Codes: C07C 31/205 1,3-Propanediol; 1,2-Propanediol
• CPC Class Codes: C12P 7/18 polyhydric

Abstract

A process for purifying 1,3-propanediol from the fermentation broth of a cultured E. coli that has been bioengineered to synthesize 1,3-propanediol from sugar is provided. The basic process entails filtration, ion exchange and distillation of the fermentation broth product stream, preferably including chemical reduction of the product during the distillation procedure. Also provided are highly purified compositions of 1,3-propanediol.

Claims

1. A process of purifying biologically-produced 1,3-propanediol from the fermentation broth of an organism able to produce 1,3-propanediol, comprising the steps of:

(a) subjecting the fermentation broth to filtration;

(b) subjecting the product of step a to ion exchange purification wherein anionic and cationic molecules are removed; and

(c) subjecting the product of step b to a distillation procedure comprising at least two distillation columns wherein one of said distillation columns removes molecules having a boiling point exceeding the boiling point of 1,3-propanediol and the other of said distillation columns removes molecules having a boiling point below the boiling point of 1,3-propanediol.

2. The process of claim 1, further comprising subjecting the product of step b to chemical reduction.

3. The process of claim 2, wherein said chemical reduction is selected from the group consisting of hydrogenation and hydroboration.

4. The process of claim 3, wherein said chemical reduction is hydrogenation.

5. The process of claim 1, further comprising wherein the fermentation broth is subjected to an evaporation step.

6. The process of claim 5, wherein said evaporation step is conducted during step b.

7. The process of claim 1, wherein the filtration process of step a comprises more than one separate filtration procedures.

8. The process of claim 7, wherein the filtration process of step a comprises a first and a second filtration procedure, said first filtration procedure comprising subjecting the fermentation broth to microfiltration comprising removing molecules having a size greater than 0.2 microns and said second filtration procedure comprising removing molecules having a molecule weight greater than about 200 Daltons.

9. The process of claim 7, wherein the filtration process of step a comprises a first, a second and a third filtration procedure:

said first filtration procedure comprising subjecting the fermentation broth to microfiltration comprising removing molecules having a size greater than 0.2 microns;

said second filtration procedure comprising subjecting the fermentation broth to ultrafiltration comprising removing molecules having a molecule weight greater than about 5000 Daltons, and said third filtration procedure comprising subjecting the fermentation broth to nanofiltration comprising removing molecules having a molecule weight greater than about 200 to 400 Daltons.

10. The process of claim 1, wherein the ion exchange process of step b comprises more than one separate ion exchange procedure.

11. The process of claim 10, wherein the ion exchange process of step b comprises subjecting the product of step a to one or more series of ion exchange procedures wherein each series of procedures comprises exposing the product to a strong acid cation exchange resin followed by exposure to a weak ion exchange resin.

12. The process of claim 10, wherein the ion exchange process of step b comprises subjecting the product of step a to two series of ion exchange procedures wherein each series comprises exposing the product to a strong acid cation exchange resin followed by exposing the product to a weak ion exchange resin.

13. The process of claim 12, wherein the ion exchange process of step b further comprises subjecting the product to a mixed ion exchange resin composition comprising a mixture of strong acid cation exchange resin and strong base anion exchange resin.

14. The process of claim of 1, wherein step b comprises subjecting the product of step a to two series of ion exchange procedures wherein each series comprises exposing the product to a strong acid cation exchange resin followed by exposing the product to a weak ion exchange resin;

followed by an evaporation step;

followed by subjecting the product to a mixed ion exchange resin composition comprising a mixture of strong acid cation exchange resin and strong base anion exchange resin.

21. A composition made by the process of any of claims 2 through 20.

15. A process of purifying biologically-produced 1,3-propanediol from the fermentation broth of an organism able to produce 1,3-propanediol, comprising the steps of:

(a) subjecting the fermentation broth to filtration;

(b) subjecting the product of step a to ion exchange purification wherein anionic and cationic molecules are removed;

(c) subjecting the product of step b to a chemical reduction procedure; and

(d) subjecting the product of step c to at least two distillations wherein in one of the distillations compounds having boiling points below that of 1,3-propanediol are removed and in another of the distillations compounds having a boiling point exceeding that of 1,3-propanediol are removed.

16. The process of claim 15, wherein said chemical reduction procedure of step c is selected from the group consisting of exposure to hydroboration and hydrogenation.

17. The process of claim 16, wherein said chemical reduction procedure is hydrogenation.

18. The process of purifying biologically-produced 1,3-propanediol from the fermentation broth of an organism able to produce 1,3-propanediol, comprising the steps of:

(a) subjecting the fermentation broth to microfiltration wherein cellular biomass of the organism is removed from the fermentation broth;

(b) subjecting the product of step a to nanofiltration wherein molecules having a molecular weight of greater than about 200 to 400 Daltons are removed;

(c) subjecting the product of step b to a series of ion exchange procedures, wherein each series comprises exposing the product of step c to a strong acid cation exchange followed by a weak base anion exchange resin;

(d) subjecting the product of step c to a mixed ion exchange procedure by exposing the product to a resin composition comprising a strong cation exchange resin mixed with a strong base anion exchange resin;

(e) subjecting the product of step d to a chemical reduction procedure; and

(f) subjecting the product of step e to a series of distillations wherein compounds remaining in the product of step e having boiling points below that of 1,3-propanediol and above that of 1,3-propanediol are removed.

19. A process of purifying biologically-produced 1,3-propanediol from the fermentation broth of an organism able to produce 1,3-propanediol, comprising the steps of:

(a) subjecting the fermentation broth to microfiltration wherein cellular biomass of the organism is removed from the fermentation broth;

(b) subjecting the product of step a to ultrafiltration wherein molecules having a molecular weight greater than about 5000 Daltons are removed;

(c) subjecting the product of step b to nanofiltration wherein molecules having a molecular weight greater than about 200 to 400 Daltons are removed;

(d) subjecting the product of step c to two series of ion exchange procedures, wherein each series comprises exposing the product of step c to a strong acid cation exchange followed by a weak base anion exchange resin;

(e) reducing the amount of water in the product of step d by evaporation;

(f) subjecting the product of step e to a mixed ion exchange procedure by exposing the product to a resin composition comprising a strong cation exchange resin mixed with a strong base anion exchange resin;

(g) subjecting the product of step f to two distillations wherein in one distillation compounds having a boiling point exceeding that of 1,3-propanediol are removed and in the other distillation compounds having a boiling point below that of 1,3-propanediol are removed;

(h) subjecting the product of step g to a chemical reduction reaction; and

(i) subjecting the product of step h to two distillations wherein in one distillation further compounds having a boiling above that of 1,3-propanediol are removed and in the other distillation further compounds having a boiling point below that of 1,3-propanediol are removed.

20. A process of purifying biologically-produced 1,3-propanediol from the fermentation broth of an organism able to produce 1,3-propanediol, comprising the steps of:

(a) subjecting the fermentation broth to ceramic crossflow microfiltration wherein cellular biomass of the organism is removed from the fermentation broth;

(b) subjecting the product of step a to ultrafiltration wherein molecules having a molecular weight greater than about 5000 Daltons are removed;

(c) subjecting the product of step b to nanofiltration using spiral wound polymeric membranes wherein molecules having a molecular weight greater than about 200 to 400 Daltons are removed;

(d) subjecting the product of step c to two series of ion exchange procedures, wherein each series comprises exposing the product of step c to a strong acid cation exchange followed by a weak base anion exchange resin;

(e) reducing the amount of water in the product of step d by evaporation;

(f) subjecting the product of step e to a mixed ion exchange procedure by exposing the product to a resin composition comprising a strong cation exchange resin mixed with a strong base anion exchange resin;

(g) subjecting the product of step f to two distillations wherein in one distillation compounds having a boiling point above that of 1,3-propanediol are removed, and in the other distillation compounds have a boiling point below that of 1,3-propanediol are removed;

(h) subjecting the product of step g to a hydrogenation reaction; and

(i) subjecting the product of step h to two distillations wherein in one distillation compounds having a boiling point above that of 1,3-propanediol are removed and in the other distillation compounds having a boiling point below that of 1,3-propanediol are removed.

22. A composition comprising biologically-produced 1,3-propanediol having an ultraviolet absorption at 220 nm of less than about 0.200 and at 250 nm of less than about 0.075 and at 275 nm of less than about 0.075.

23. A composition comprising biologically-produced 1,3-propanediol having a “

b”

color value of less than about 0.15 and an absorbance at 275 nm of less than about 0.050.

24. A composition comprising biologically-produced 1,3-propanediol having a peroxide concentration of less than about 10 ppm.

25. A composition comprising biologically-produced 1,3-propanediol having a concentration of total organic impurities in said composition of less than about 400 ppm.

26. A composition comprising biologically-produced 1,3-propanediol having a concentration of total organic impurities in said composition of less than about 300 ppm.

27. A composition comprising biologically-produced 1,3-propanediol having a concentration of total organic impurities in said composition of less than about 150 ppm.

28. A composition comprising 1,3-propanediol having a concentration of total organic impurities in said composition of less than about 400 ppm.

29. A composition comprising 1,3-propanediol having a concentration of total organic impurities in said composition of less than about 300 ppm.

30. A composition comprising 1,3-propanediol having a concentration of total organic impurities in said composition of less than about 150 ppm.

31. A composition comprising 1,3-propanediol having a concentration of peroxides of less than about 10 ppm.

32. A composition comprising 1,3-propanediol having a concentration of carbonyl groups of less than about 10 ppm.