CA2579721A1 - Single solvent polymer extraction methods - Google Patents
Single solvent polymer extraction methods Download PDFInfo
- Publication number
- CA2579721A1 CA2579721A1 CA002579721A CA2579721A CA2579721A1 CA 2579721 A1 CA2579721 A1 CA 2579721A1 CA 002579721 A CA002579721 A CA 002579721A CA 2579721 A CA2579721 A CA 2579721A CA 2579721 A1 CA2579721 A1 CA 2579721A1
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- combination
- pha
- combining
- boiling point
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002904 solvent Substances 0.000 title claims abstract 141
- 238000000605 extraction Methods 0.000 title abstract 7
- 229920000642 polymer Polymers 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 93
- 238000009835 boiling Methods 0.000 claims abstract 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 15
- 239000000203 mixture Substances 0.000 claims abstract 7
- 238000010438 heat treatment Methods 0.000 claims 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 21
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 14
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 14
- 239000008187 granular material Substances 0.000 claims 14
- 239000007788 liquid Substances 0.000 claims 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 2
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 abstract 18
- 229920000903 polyhydroxyalkanoate Polymers 0.000 abstract 17
- 239000002028 Biomass Substances 0.000 abstract 4
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/89—Recovery of the polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
Abstract
The invention provides a method that is useful for isolating a polyhydroxyalkanoate (PHA) from biomass. The method may comprise the steps of contacting the biomass with a PHA extraction solvent to form a first combination comprising a PHA phase and a residual biomass phase; separating the PHA phase from the residual biomass phase; introducing the PHA phase into a PHA
receiving solvent, thereby forming a second combination, wherein the PHA extraction solvent is capable of forming a minimum boiling azeotrope with the PHA receiving solvent;
maintaining the second combination at a temperature and pressure such that the PHA extraction solvent of the PHA phase and a portion of the PHA receiving solvent are removed from the second combination in the gaseous state as an azeotropic mixture; and precipitating the PHA from the second combination when the PHA
extraction solvent is removed from the second combination; and recovering the PHA;
wherein: the PHA extraction solvent is selected from the group consisting of ketones, esters, alcohols and alkanes; the PHA receiving solvent is water; and the PHA
extraction solvent has a higher boiling point than the PHA receiving solvent.
receiving solvent, thereby forming a second combination, wherein the PHA extraction solvent is capable of forming a minimum boiling azeotrope with the PHA receiving solvent;
maintaining the second combination at a temperature and pressure such that the PHA extraction solvent of the PHA phase and a portion of the PHA receiving solvent are removed from the second combination in the gaseous state as an azeotropic mixture; and precipitating the PHA from the second combination when the PHA
extraction solvent is removed from the second combination; and recovering the PHA;
wherein: the PHA extraction solvent is selected from the group consisting of ketones, esters, alcohols and alkanes; the PHA receiving solvent is water; and the PHA
extraction solvent has a higher boiling point than the PHA receiving solvent.
Claims (74)
1. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent; and heating the combination to form the azeotrope of the first and second solvents.
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent; and heating the combination to form the azeotrope of the first and second solvents.
2. The method of claim 1, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone.
3. The method of claim 2, wherein the second solvent comprises water.
4. The method of claim 1, wherein the second solvent comprises water.
5. The method of claim 1, wherein heating the combination substantially removes the first solvent from the combination.
6. The method of claim 1, wherein the azeotrope forms at a temperature below the boiling point of the first solvent and below the boiling point of the second solvent.
7. The method of claim 1, further comprising forming granules of the PHA.
8. The method of claim 7, wherein the PHA granules have a bulk density of at least about 0.25 kg/m3.
9. The method of claim 1, wherein, before heating, the method comprises:
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
10. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent; and after forming the combination, forming granules of the PHA.
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent; and after forming the combination, forming granules of the PHA.
11. The method of claim 10, wherein the granules of the PHA have a bulk density of at least about 0.25 kg/m3.
12. The method of claim 10, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone.
13. The method of claim 12, wherein the second solvent comprises water.
14. The method of claim 10, wherein the second solvent comprises water.
15. The method of claim 10, wherein heating the combination substantially removes the first solvent from the combination.
16. The method of claim 10, wherein the azeotrope forms at a temperature below the boiling point of the first solvent and below the boiling point of the second solvent.
17. The method of claim 10, wherein, before forming the PHA granules, the method comprises:
heating the combination to substantially remove the first solvent, thereby forming a second combination comprising the PHA and the second solvent;
and reducing the temperature of the second combination.
heating the combination to substantially remove the first solvent, thereby forming a second combination comprising the PHA and the second solvent;
and reducing the temperature of the second combination.
18. The method of claim 17, wherein, before heating, the method comprises:
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
19. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent having a higher boiling point than the second solvent;
and heating the combination to a temperature less than the boiling point of the second solvent to remove at least some of the PHA from the combination.
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent having a higher boiling point than the second solvent;
and heating the combination to a temperature less than the boiling point of the second solvent to remove at least some of the PHA from the combination.
20. The method of claim 19, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone.
21. The method of claim 20, wherein the second solvent comprises water.
22. The method of claim 21, wherein the second solvent comprises water.
23. The method of claim 19, wherein the first solvent is capable of forming an azeotrope with the second solvent.
24. The method of claim 23, wherein heating the combination forms the azeotrope of the first and second solvents.
25. The method of claim 19, further comprising forming granules of the PHA.
26. The method of claim 25, wherein the PHA granules have a bulk density of at least about 0.25 kg/m3.
27. The method of claim 19, wherein, before heating, the method comprises:
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
28. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent having a higher boiling point than the second solvent;
and heating the combination to a temperature less than the boiling point of the second solvent to substantially remove the first solvent from the combination.
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent having a higher boiling point than the second solvent;
and heating the combination to a temperature less than the boiling point of the second solvent to substantially remove the first solvent from the combination.
29. The method of claim 28, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone.
30. The method of claim 29, wherein the second solvent comprises water.
31. The method of claim 28, wherein the second solvent comprises water.
32 32. The method of claim 28, wherein the first solvent is capable of forming an azeotrope with the second solvent.
33. The method of claim 32, wherein heating the combination forms the azeotrope of the first and second solvents.
34. The method of claim 28, further comprising forming granules of the PHA.
35. The method of claim 34, wherein the PHA granules have a bulk density of at least about 0.25 kg/m3.
36. The method of claim 28, wherein, before heating, the method comprises:
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
37. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent;
heating the combination to form a vapor mixture comprising the first and second solvents; and condensing the vapor mixture to form a liquid comprising first and second phases, the first phase of the liquid being substantially free of the first solvent, the second phase of the liquid being substantially free of the second solvent.
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent;
heating the combination to form a vapor mixture comprising the first and second solvents; and condensing the vapor mixture to form a liquid comprising first and second phases, the first phase of the liquid being substantially free of the first solvent, the second phase of the liquid being substantially free of the second solvent.
38. The method of claim 37, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone
39. The method of claim 38, wherein the second solvent comprises water.
40. The method of claim 37, wherein the second solvent comprises water.
41. The method of claim 37, wherein heating the combination substantially removes the first solvent from the combination.
42. The method of claim 37, wherein the azeotrope of the first and second solvents forms at a temperature below the boiling point of the first solvent and below the boiling point of the second solvent.
43. The method of claim 37, further comprising forming granules of the PHA.
44. The method of claim 43, wherein the PHA crystals have a bulk density of at least about 0.25 kg/m3.
45. The method of claim 37, wherein, before heating, the method comprises:
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
46. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent having a higher boiling point than the second solvent;
heating the combination to form a vapor mixture comprising the first and second solvents; and condensing the vapor mixture to form a liquid comprising first and second phases, the first phase of the liquid being substantially free of the first solvent, the second phase of the liquid being substantially free of the second solvent.
combining the PHA, a first solvent and a second solvent to form a combination, the first solvent having a higher boiling point than the second solvent;
heating the combination to form a vapor mixture comprising the first and second solvents; and condensing the vapor mixture to form a liquid comprising first and second phases, the first phase of the liquid being substantially free of the first solvent, the second phase of the liquid being substantially free of the second solvent.
47. The method of claim 46, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone.
48. The method of claim 47, wherein the second solvent comprises water.
49. The method of claim 46, wherein the second solvent comprises water.
50. The method of claim 46, wherein the first solvent is capable of forming an azeotrope with the second solvent.
51. The method of claim 50, wherein heating the combination forms the azeotrope of the first and second solvents.
52. The method of claim 51, wherein the combination is heated to a temperature below a boiling point of the first solvent and below a boiling point of the second solvent.
53. The method of claim 50, wherein the combination is heated to a temperature below a boiling point of the first solvent and below a boiling point of the second solvent.
54. The method of claim 46, further comprising forming granules of the PHA.
55. The method of claim 54, wherein the PHA crystals have a bulk density of at least about 0.25 kg/m3.
56. The method of claim 46, wherein, before heating, the method comprises:
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
combining the PHA and the first solvent to form a first combination;
and combining the first combination with the second solvent to form the combination.
57. A method of isolating a PHA, the method comprising:
combining the PHA, a first solvent, a second solvent, and a third solvent to form a combination, the first solvent and the second solvent being capable of forming an azeotrope with the third solvent; and after forming the combination, forming granules of the PHA.
combining the PHA, a first solvent, a second solvent, and a third solvent to form a combination, the first solvent and the second solvent being capable of forming an azeotrope with the third solvent; and after forming the combination, forming granules of the PHA.
58. The method of claim 57, wherein heating the combination substantially removes the first solvent and the second solvent from the combination.
59. The method of claim 58, wherein heating the combination forms a ternary azeotrope of the first solvent, the second solvent, and the third solvent.
60. The method of claim 58, wherein heating the combination forms a binary azeotrope of the first solvent and the third solvent and a binary azeotrope of the second solvent and the third solvent.
61. The method of claim 59, wherein the azeotrope forms at a temperature below the boiling point of the first solvent, below the boiling point of the second solvent, and below the boiling point of the third solvent.
62. The method of claim 60, wherein the azeotrope forms at a temperature below the boiling point of the first solvent, below the boiling point of the second solvent, and below the boiling point of the third solvent.
63. The method of claim 57, wherein the first solvent is selected from the group consisting of MIBK, butyl acetate, ethyl acetate, cyclopentanone, and cyclohexanone.
64. The method of claim 63, wherein the first solvent is MIBK.
65. The method of claim 64, wherein the first solvent is miscible with the second solvent.
66. The method of claim 65, wherein the ratio of the second solvent to the first solvent is less than about 0.10.
67. The method of claim 66, wherein the PHA has a solubility in the second solvent of less than about 0.2 percent of the PHA at 20°C.
68. The method of claim 67, wherein the second solvent comprises n-heptane.
69. The method of claim 68, wherein the third solvent comprises water.
70. The method of claim 57, wherein the third solvent comprises water.
71. The method of claim 57, wherein the granules of the PHA have a bulk density of at least about 0.25 kg/m3.
72. The method of claim 57, wherein, before forming the PHA granules, the method comprises:
heating the combination to substantially remove the first solvent and the second solvent, thereby forming a second combination comprising the PHA
and the third solvent; and reducing the temperature of the second combination.
heating the combination to substantially remove the first solvent and the second solvent, thereby forming a second combination comprising the PHA
and the third solvent; and reducing the temperature of the second combination.
73. The method of claim 72, wherein, before heating, the method comprises:
combining the PHA, the first solvent, and the second solvent to form a first combination; and combining the first combination with the third solvent to form the combination.
combining the PHA, the first solvent, and the second solvent to form a first combination; and combining the first combination with the third solvent to form the combination.
74. The method of claim 57, wherein the method further comprises:
heating the combination to form a vapor mixture comprising the first, second, and third solvents; and condensing the vapor mixture to form a liquid comprising first and second phases, the first phase of the liquid being substantially free of the first and second solvents, the second phase of the liquid being substantially free of the third solvent.
heating the combination to form a vapor mixture comprising the first, second, and third solvents; and condensing the vapor mixture to form a liquid comprising first and second phases, the first phase of the liquid being substantially free of the first and second solvents, the second phase of the liquid being substantially free of the third solvent.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60928004P | 2004-09-13 | 2004-09-13 | |
| US60/609,280 | 2004-09-13 | ||
| PCT/US2005/031624 WO2006031492A1 (en) | 2004-09-13 | 2005-09-06 | Single solvent polymer extraction methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2579721A1 true CA2579721A1 (en) | 2006-03-23 |
| CA2579721C CA2579721C (en) | 2012-11-27 |
Family
ID=36060356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2579721A Active CA2579721C (en) | 2004-09-13 | 2005-09-06 | Single solvent polymer extraction methods |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US7576173B2 (en) |
| EP (2) | EP1802681B1 (en) |
| JP (1) | JP4945447B2 (en) |
| CN (1) | CN101065416B (en) |
| AT (1) | ATE531748T1 (en) |
| AU (1) | AU2005285271B2 (en) |
| BR (1) | BRPI0515267B1 (en) |
| CA (1) | CA2579721C (en) |
| ES (1) | ES2375971T3 (en) |
| WO (1) | WO2006031492A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014078014A2 (en) | 2012-11-14 | 2014-05-22 | Metabolix, Inc. | Production of salts of 4-hydroxybutyrate using biobased raw materials |
| CA2893685A1 (en) * | 2012-12-18 | 2014-06-26 | Veolia Water Solutions & Technologies Support | Method of producing polyhydroxyalkanoate compounded plastics having improved mechanical properties |
| US20150376152A1 (en) | 2013-02-13 | 2015-12-31 | Metabolix, Inc. | Process for Ultra Pure Chemical Production from Biobased Raw Starting Materials |
| US9290612B2 (en) | 2013-03-13 | 2016-03-22 | Tepha, Inc. | Compositions and devices of poly-4-hydroxybutyrate |
| US9249378B2 (en) | 2013-08-02 | 2016-02-02 | Eastman Chemical Company | Aqueous cleaning compositions having enhanced properties |
| US9255059B2 (en) | 2013-08-02 | 2016-02-09 | Eastman Chemical Company | Method for producing an alkyl 3-hydroxybutyrate |
| US9388114B2 (en) | 2013-08-02 | 2016-07-12 | Eastman Chemical Company | Compositions including an alkyl 3-hydroxybutyrate |
| US9163202B2 (en) | 2013-08-02 | 2015-10-20 | Eastman Chemical Company | Aqueous cleaning compositions including an alkyl 3-hydroxybutyrate |
| ES2705687T3 (en) | 2013-11-05 | 2019-03-26 | Tepha Inc | Poly-4-hydroxybutyrate compositions and devices |
| KR102280247B1 (en) * | 2014-10-16 | 2021-07-21 | 에스케이이노베이션 주식회사 | Method of Preparing Anhydrosugar Alcohols by Azeotropic Distillation |
| CN111346580B (en) * | 2020-04-29 | 2020-12-11 | 吉林中粮生化有限公司 | Method and system for extracting polyhydroxyalkanoate by combining high temperature and high pressure with ultrasound |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT395319B (en) * | 1990-10-05 | 1992-11-25 | Danubia Petrochem Polymere | METHOD FOR OBTAINING A POLYHYDROXYALKANOATE FROM THE CELL MATERIAL OF A MICROORGANISM AND POLYHYDROXYALKANOATE FLAKES |
| CN1104683A (en) * | 1993-12-29 | 1995-07-05 | 中国科学院成都生物研究所 | Preparation of betal-polyhydroxybutyrate |
| GB9416690D0 (en) * | 1994-08-18 | 1994-10-12 | Zeneca Ltd | Process for the recovery of polyhydroxyalkanoic acid |
| US5942597A (en) * | 1995-08-21 | 1999-08-24 | The Procter & Gamble Company | Solvent extraction of polyhydroxyalkanoates from biomass |
| CZ295187B6 (en) * | 1995-08-21 | 2005-06-15 | The Procter & Gamble Company | Process for separating polyhydroxy-alkanoate from biomass |
| JPH09191893A (en) * | 1996-01-22 | 1997-07-29 | Taisei Corp | Production of hydroxyalkanoic acid copolymer |
| US6087471A (en) | 1997-04-15 | 2000-07-11 | Monsanto Company | High temperature PHA extraction using PHA-poor solvents |
| CN1070534C (en) * | 1998-01-23 | 2001-09-05 | 清华大学 | Method for separating and refining polyhydroxy fatty acid ester in bacteria cell from bacteria |
| PL342996A1 (en) * | 1998-02-23 | 2001-07-16 | Mnemoscience Gmbh | Shape memory polymers |
| EP2305324B1 (en) * | 1999-03-25 | 2014-09-17 | Metabolix, Inc. | Medical devices and applications of polyhydroxyalkanoate polymers |
| JP4790912B2 (en) * | 1999-05-12 | 2011-10-12 | メタボリックス，インコーポレイテッド | Process for purifying polyhydroxyalkanoates |
| WO2001068890A2 (en) * | 2000-03-10 | 2001-09-20 | Metabolix, Inc. | Method of extracting polyhydroxyalkanoate from a solution |
| PT1529072E (en) * | 2002-08-06 | 2012-11-14 | Metabolix Inc | Polymer extraction methods |
| WO2005049692A1 (en) * | 2003-11-21 | 2005-06-02 | Kaneka Corporation | Process for producing polyhydroxyalkanoate crystal |
| AU2004293501B2 (en) | 2003-11-28 | 2009-10-29 | Phb Industrial S.A. | Process for recovering polyhydroxialkanoates ("PHAs") from cellular biomass |
| JP2005239998A (en) * | 2004-01-29 | 2005-09-08 | Mitsubishi Engineering Plastics Corp | Polyphenylene ether resin composition |
| US20050239998A1 (en) * | 2004-03-04 | 2005-10-27 | Koichi Kinoshita | Method for producing polyhydroxyalkanoate |
| BRPI0508083A (en) | 2004-03-04 | 2007-07-17 | Kaneka Corp | process for producing polyhydroxyalkanoate |
| TW200617171A (en) * | 2004-06-29 | 2006-06-01 | Procter & Gamble | Improved process for the solvent-based extraction of polyhydroxyalkanoates from biomass |
-
2005
- 2005-09-06 JP JP2007531250A patent/JP4945447B2/en active Active
- 2005-09-06 US US11/220,119 patent/US7576173B2/en active Active
- 2005-09-06 EP EP05793090A patent/EP1802681B1/en active Active
- 2005-09-06 EP EP10009537A patent/EP2256143A1/en not_active Withdrawn
- 2005-09-06 WO PCT/US2005/031624 patent/WO2006031492A1/en active Application Filing
- 2005-09-06 CN CN200580038924XA patent/CN101065416B/en active Active
- 2005-09-06 AU AU2005285271A patent/AU2005285271B2/en not_active Ceased
- 2005-09-06 AT AT05793090T patent/ATE531748T1/en active
- 2005-09-06 BR BRPI0515267-4A patent/BRPI0515267B1/en active IP Right Grant
- 2005-09-06 CA CA2579721A patent/CA2579721C/en active Active
- 2005-09-06 ES ES05793090T patent/ES2375971T3/en active Active
-
2009
- 2009-07-02 US US12/497,362 patent/US7795376B2/en active Active
-
2010
- 2010-08-17 US US12/857,859 patent/US7893194B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP4945447B2 (en) | 2012-06-06 |
| ATE531748T1 (en) | 2011-11-15 |
| EP1802681A4 (en) | 2007-11-14 |
| US7576173B2 (en) | 2009-08-18 |
| EP2256143A1 (en) | 2010-12-01 |
| WO2006031492A8 (en) | 2007-07-05 |
| AU2005285271A1 (en) | 2006-03-23 |
| EP1802681B1 (en) | 2011-11-02 |
| US20100016544A1 (en) | 2010-01-21 |
| US7893194B2 (en) | 2011-02-22 |
| US20100311940A1 (en) | 2010-12-09 |
| EP1802681A1 (en) | 2007-07-04 |
| BRPI0515267A (en) | 2008-07-15 |
| JP2008512552A (en) | 2008-04-24 |
| WO2006031492A1 (en) | 2006-03-23 |
| BRPI0515267B1 (en) | 2017-11-14 |
| ES2375971T3 (en) | 2012-03-07 |
| US20060058501A1 (en) | 2006-03-16 |
| CN101065416B (en) | 2011-04-13 |
| CN101065416A (en) | 2007-10-31 |
| AU2005285271B2 (en) | 2010-09-09 |
| US7795376B2 (en) | 2010-09-14 |
| CA2579721C (en) | 2012-11-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2579721A1 (en) | Single solvent polymer extraction methods | |
| CA2494322A1 (en) | Polymer extraction methods | |
| JP2008512552A5 (en) | ||
| US9126917B2 (en) | Method for purifying vanillin by liquid-liquid extraction | |
| CA2917037C (en) | Method for processing magnesium chloride solutions | |
| KR20080041195A (en) | Process for the recycling of expanded polystyrene | |
| BRPI0501844A (en) | process for extraction and recovery of polyhydroxyalkanoates (phas) from cellular biomass | |
| JP2000334738A (en) | Recycling method for styrol resin waste material | |
| CN107641216B (en) | Method for recovering waste foamed polystyrene | |
| WO2022122028A1 (en) | Method and device for back-extraction purification of crude product obtained by sublimation of maltol or ethyl maltol | |
| TWI331152B (en) | ||
| CN101861337B (en) | Process for recovering a polymer from a solution | |
| WO2013026727A1 (en) | A method for separating compounds of similar structure. | |
| EP2054367A2 (en) | Process for the preparation of sodium salt of ibuprofen of different particle sizes | |
| JP2001505128A (en) | Material processing | |
| JPS63230659A (en) | Recovery of polymerization inhibitor | |
| JPS60156596A (en) | Solvent mixture and extracting method | |
| JPH06506691A (en) | How to separate peptides from resin | |
| CN108359085B (en) | Dehydration process applied to synthesis of alkyd or polyester resin | |
| US9522834B2 (en) | Process for removing salts from a processing liquid | |
| JP2007191586A (en) | Method for producing reclaimed polyvinyl chloride compound | |
| JP2003305302A (en) | Method for removing water insoluble porogen | |
| US4031148A (en) | Method of separating chlorinated aliphatic hydrocarbons from mixtures thereof by liquid-liquid extraction | |
| EP0076620A2 (en) | Process for recovering caffeine from activated carbon | |
| JP2011111439A (en) | Purification method for anhydrosugar alcohol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |