Continuous process for manufacture of a purified lactide

• US 5,274,073 A
• Filed: 08/24/1992
• Issued: 12/28/1993
• Est. Priority Date: 01/24/1992
• Status: Expired due to Term

• Current Assignee: Cargill, Inc. (Agricultural Services Division)
• Original Assignee: Cargill, Inc. (Agricultural Services Division)
• Inventors: Iwen, Matthew L., Kolstad, Jeffrey J., Gruber, Patrick R., Hall, Eric S., Benson, Richard D., Borchardt, Ronald L.
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): Dodson, Shelley A.
• Application Number:
  US07/935,059
• Time in Patent Office: 491 Days
• Field of Search: 528/354, 528/357, 528/415, 549/274, 526/67, 526/68, 525/415
• US Class Current: 528/354
• CPC Class Codes: C08G 63/06 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 63/08 Lactones or lactides

Abstract

A process for the continuous conversion of crude lactic acid to a substantially purified lactide or polylactide including the steps of polymerizing the lactic acid to form a prepolymer with subsequent depolymerization to form a crude lactide in the presence of a catalyst. The crude lactide is purified in an improved distillation system in which at least three fractions are formed with the substantially purified lactide removed as an intermediate boiling sidedraw stream. The substantially purified lactide may then be polymerized.

Claims

1. A process for the continuous conversion of a crude lactic acid feed in an aqueous medium to substantially purified lactide, said process comprising the steps of:

a) providing a source of lactic acid in an aqueous medium;

b) concentrating the lactic acid in the aqueous medium by evaporating a substantial portion of the aqueous medium to form a concentrated lactic acid solution;

c) polymerizing lactic acid in the concentrated lactic acid solution of step (b) by further evaporation of the aqueous medium to form polylactic acid molecules having an average molecular weight of between about 100 and about 5000;

d) forming a crude lactide in the presence of catalyst means for catalyzing the depolymerization of the polylactic acid molecules to form lactide molecules; and

e) purifying the crude lactide formed in step (d) to form a substantially purified lactide by distilling the crude lactide, wherein distilling the crude lactide comprises fractionating the crude lactide into at least three component streams, an overhead low-boiling stream, a high-boiling bottoms stream and an intermediate boiling sidedraw stream.

2. The process of claim 1, wherein the overhead low-boiling stream of step (e) comprises water, solvent, lactic acid, ester of lactic acid, lactide, dimer or combinations thereof.

3. The process of claim 1, wherein the high-boiling bottoms stream of step (e) comprises oligomers of lactic acid having at least two lactic acid molecules per polymer chain and the concentration of lactide is less than about 20 percent by weight of said high-boiling bottoms stream.

4. The process of claim 1, wherein the intermediate-boiling sidedraw stream of step (e) comprises substantially purified lactide of purity greater than or equal to about 99 percent by weight of said intermediate boiling sidedraw stream.

5. The process of claim 1, wherein the intermediate boiling sidedraw stream of step (e) is further distilled in a distillation process.

6. The process of claim 1, wherein the intermediate-boiling sidedraw stream of step (e) is a vapor comprising substantially purified lactide.

7. The process of claim 1, wherein the crude lactide formed in step (d) is vaporized to form a lactide vapor, said lactide vapor being contained within a single enclosed space, said single enclosed space comprising a reactor equipped with a top-mounted distillation column, wherein said purifying of the crude lactide of step (e) is completed to form a substantially purified lactide.

8. The process of claim 7, wherein the substantially purified lactide is removed from said top-mounted distillation column as an intermediate boiling sidedraw stream.

9. The process of claim 1, wherein the high-boiling bottoms stream of step (e) is recycled to form a crude lactide in the presence of catalyst means for catalyzing the depolymerization of the polylactic acid molecules to form lactide molecules as in step (d).

10. The process of claim 1, wherein the source of lactic acid of step (a) is an aqueous solution of lactic acid and water in concentrations ranging from about 1 percent by weight lactic acid to about 99 percent by weight lactic acid.

11. The process of claim 1, wherein racemization of the lactic acid is controlled in a range of 0% to 100% by altering residence times in process equipment, impurity levels, catalyst levels, catalyst type, temperatures and pressures.

12. The process of claim 1, wherein the crude lactide formed in step (d) is a vapor, said vapor being subsequently partially condensed to remove volatile contaminants to form a condensed partially purified liquid lactide, the condensed partially purified liquid lactide then being purified as in step (e).

13. The process of claim 1, wherein the source of lactic acid for step (a) contains impurities, which may include but are not limited to, color bodies, carbohydrates, aldehydes, ketones, proteins, amino acids, salts, metal ions, carboxylic acids or combinations thereof.

14. The process of claim 1, wherein the yield of lactide is maximized by recycling streams containing recoverable lactic acid, lactide or oligomers and polymers thereof.

15. The process of claim 1, wherein the crude lactide formed in step (d) is generated in a reactor under conditions of elevated temperature and reduced pressure.

16. A process for the continuous conversion of a crude lactic acid feed in a hydroxylic medium to a substantially purified lactide, said process comprising the steps of:

a) providing a source of lactic acid in a hydroxylic medium;

b) concentrating the lactic acid in the hydroxylic medium by evaporating a substantial portion of the hydroxylic medium to form a concentrated lactic acid solution;

c) polymerizing lactic acid in the concentrated lactic acid solution of step (b) by further evaporation of the hydroxylic medium to form polylactic acid molecules having an average molecular weight of between about 100 and about 5000;

d) forming a crude lactide in the presence of catalyst means for catalyzing the depolymerization of the polylactic acid molecules to form lactide molecules; and

e) purifying the crude lactide formed in step (d) to form a substantially purified lactide by distilling the crude lactide, wherein distilling the crude lactide comprises fractionating the crude lactide into at least three component streams, an overhead low-boiling stream, a high-boiling bottoms stream and an intermediate boiling sidedraw stream.

17. The process of claim 16, wherein the overhead low-boiling stream of step (e) comprises water, solvent, lactic acid, ester of lactic acid, lactide, dimer or combinations thereof.

18. The process of claim 16, wherein the high-boiling bottom stream of step (e) comprises oligomers of lactic acid having at least two lactic acid molecules per polymer chain and the concentration of lactide is less about 20 percent by weight.

19. The process of claim 16, wherein the intermediate-boiling sidedraw stream of step (e) comprises substantially purified lactide of purity greater than or equal to about 99 percent by weight lactide.

20. The process of claim 16, wherein the intermediate boiling sidedraw stream of step (e) is further distilled in a distillation process.

21. The process of claim 16, wherein the intermediate-boiling sidedraw stream of step (e) is a vapor comprising substantially purified lactide.

22. The process of claim 16, wherein the crude lactide formed in step (d) is vaporized to form a lactide vapor, said lactide vapor being contained within a single enclosed space, said single enclosed space comprising a reactor equipped with a top-mounted distillation column, wherein said purifying of step (e) is completed to form a substantially purified lactide as an intermediate boiling sidedraw stream.

23. The process of claim 22, wherein the substantially purified lactide is removed from said top-mounted distillation column as an intermediate boiling sidedraw stream.

24. The process of claim 16, wherein the high-boiling bottoms stream of step (e) is recycled to form a crude lactide in the presence of catalyst means for catalyzing the depolymerization of the polylactic acid molecules to form lactide molecules as in step (d).

25. The process of claim 16, wherein the source of lactic acid of step (a) is a solution of lactic acid and a hydroxylic medium in concentrations ranging from about 1% lactic acid to about 99% lactic acid.

26. The process of claim 16, wherein racemization of the lactic acid is controlled in a range of 0% to 100% by altering residence times in process equipment, impurity levels, catalyst levels, catalyst type, temperatures and pressures.

27. The process of claim 16, wherein the crude lactide formed in step (d) is a vapor being subsequently partially condensed to remove volatile contaminants to form a condensed partially purified liquid lactide, the condensed partially purified liquid lactide then being purified as in step (e).

28. The process of claim 16, wherein the source of lactic acid for step (a) contains impurities, which may include but are not limited to, color bodies, carbohydrates, aldehydes, ketones, proteins, amino acids, salts, metal ions, carboxylic acids or combinations thereof.

29. The process of claim 16, wherein the yield of lactide is maximized by recycling streams containing recoverable lactic acid, lactide or oligomers and polymers thereof.

30. The process of claim 16, wherein the crude lactide formed in step (d) is generated in a reactor under conditions of elevated temperature and reduced pressure.