US5274073A
Expired / Lapsed
US
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Continuous process for manufacture of a purified lactide
Assignee: Cargill Inc
•
Filing: 1992-08-24
•
Granted: 1993-12-28
•
Expires: 2012-08-24
Abstract
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.
Inventors
- 👤 Patrick R. Gruber
- 👤 Eric S. Hall
- 👤 Jeffrey J. Kolstad
- 👤 Matthew L. Iwen
- 👤 Richard D. Benson
- 👤 Ronald L. Borchardt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:45
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/06; C08G63/08
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
174 words
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.
Claim 2
Dependent Claim
174 words
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.
Claim 3
Dependent Claim
27 words
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.
Claim 4
Dependent Claim
46 words
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.
Claim 5
Dependent Claim
35 words
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.
Claim 6
Dependent Claim
21 words
The process of claim 1, wherein the intermediate boiling sidedraw stream of step (e) is further distilled in a distillation process.
Claim 7
Dependent Claim
20 words
The process of claim 1, wherein the intermediate-boiling sidedraw stream of step (e) is a vapor comprising substantially purified lactide.
Claim 8
Dependent Claim
61 words
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.
Claim 9
Dependent Claim
23 words
The process of claim 7, wherein the substantially purified lactide is removed from said top-mounted distillation column as an intermediate boiling sidedraw stream.
Claim 10
Dependent Claim
43 words
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).
Claim 11
Dependent Claim
42 words
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.
Claim 12
Dependent Claim
36 words
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.
Claim 13
Dependent Claim
47 words
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).
Claim 14
Dependent Claim
40 words
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.
Claim 15
Dependent Claim
25 words
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.
Claim 16
Dependent Claim
26 words
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.
Claim 17
Dependent Claim
175 words
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.
Claim 18
Dependent Claim
175 words
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.
Claim 19
Dependent Claim
27 words
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.
Claim 20
Dependent Claim
40 words
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.
Claim 21
Dependent Claim
30 words
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.
Claim 22
Dependent Claim
21 words
The process of claim 16, wherein the intermediate boiling sidedraw stream of step (e) is further distilled in a distillation process.
Claim 23
Dependent Claim
20 words
The process of claim 16, wherein the intermediate-boiling sidedraw stream of step (e) is a vapor comprising substantially purified lactide.
Claim 24
Dependent Claim
63 words
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.
Claim 25
Dependent Claim
23 words
The process of claim 22, wherein the substantially purified lactide is removed from said top-mounted distillation column as an intermediate boiling sidedraw stream.
Claim 26
Dependent Claim
43 words
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).
Claim 27
Dependent Claim
37 words
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.
Claim 28
Dependent Claim
36 words
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.
Claim 29
Dependent Claim
45 words
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).
Claim 30
Dependent Claim
40 words
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.
Claim 31
Dependent Claim
25 words
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.
Claim 32
Dependent Claim
26 words
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.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-12-27 | 1997-06-28 | 1997-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-12-27 | 2001-06-28 | 2001-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-12-27 | 2005-06-28 | 2005-12-28 | $7700.00 | Window Closed / Lapsed |