WO1997015681B1 - Procedes d'extraction de polyhydroxyalkanoates a partir de vegetaux - Google Patents
Procedes d'extraction de polyhydroxyalkanoates a partir de vegetauxInfo
- Publication number
- WO1997015681B1 WO1997015681B1 PCT/US1996/016921 US9616921W WO9715681B1 WO 1997015681 B1 WO1997015681 B1 WO 1997015681B1 US 9616921 W US9616921 W US 9616921W WO 9715681 B1 WO9715681 B1 WO 9715681B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pha
- oil
- group
- plant
- biomass
- Prior art date
Links
- 229920000903 polyhydroxyalkanoate Polymers 0.000 title claims abstract 62
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 title claims abstract 57
- 238000000034 method Methods 0.000 title claims abstract 45
- 208000037534 Progressive hemifacial atrophy Diseases 0.000 claims abstract 59
- 239000002028 Biomass Substances 0.000 claims abstract 26
- 239000003921 oil Substances 0.000 claims abstract 26
- 239000000203 mixture Substances 0.000 claims abstract 17
- 239000002904 solvent Substances 0.000 claims abstract 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract 5
- 102000004190 Enzymes Human genes 0.000 claims abstract 4
- 108090000790 Enzymes Proteins 0.000 claims abstract 4
- 244000038559 crop plants Species 0.000 claims abstract 4
- 230000009261 transgenic effect Effects 0.000 claims abstract 4
- 239000010773 plant oil Substances 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims abstract 3
- 238000004587 chromatography analysis Methods 0.000 claims abstract 2
- 238000004821 distillation Methods 0.000 claims abstract 2
- 238000000605 extraction Methods 0.000 claims abstract 2
- 238000000227 grinding Methods 0.000 claims abstract 2
- 238000005096 rolling process Methods 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims 21
- 235000012054 meals Nutrition 0.000 claims 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 239000003960 organic solvent Substances 0.000 claims 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 238000007781 pre-processing Methods 0.000 claims 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 102000005744 Glycoside Hydrolases Human genes 0.000 claims 2
- 108010031186 Glycoside Hydrolases Proteins 0.000 claims 2
- 108090001060 Lipase Proteins 0.000 claims 2
- 239000004367 Lipase Substances 0.000 claims 2
- 102000004882 Lipase Human genes 0.000 claims 2
- 101710163270 Nuclease Proteins 0.000 claims 2
- 108091005804 Peptidases Proteins 0.000 claims 2
- 102000009097 Phosphorylases Human genes 0.000 claims 2
- 108010073135 Phosphorylases Proteins 0.000 claims 2
- 239000004365 Protease Substances 0.000 claims 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000005910 alkyl carbonate group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 238000004140 cleaning Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229960004132 diethyl ether Drugs 0.000 claims 2
- 150000002009 diols Chemical class 0.000 claims 2
- 230000001804 emulsifying effect Effects 0.000 claims 2
- 150000002170 ethers Chemical class 0.000 claims 2
- 229940052303 ethers for general anesthesia Drugs 0.000 claims 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims 2
- 229940093858 ethyl acetoacetate Drugs 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 150000001261 hydroxy acids Chemical class 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 150000002596 lactones Chemical class 0.000 claims 2
- 239000004816 latex Substances 0.000 claims 2
- 229920000126 latex Polymers 0.000 claims 2
- 235000019421 lipase Nutrition 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 150000007970 thio esters Chemical class 0.000 claims 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims 2
- 229940117972 triolein Drugs 0.000 claims 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 claims 1
- BTJFTHOOADNOOS-UHFFFAOYSA-N 2-hydroxynonanoic acid Chemical compound CCCCCCCC(O)C(O)=O BTJFTHOOADNOOS-UHFFFAOYSA-N 0.000 claims 1
- JKRDADVRIYVCCY-UHFFFAOYSA-N 2-hydroxyoctanoic acid Chemical compound CCCCCCC(O)C(O)=O JKRDADVRIYVCCY-UHFFFAOYSA-N 0.000 claims 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 claims 1
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims 1
- 241000589291 Acinetobacter Species 0.000 claims 1
- 241001133760 Acoelorraphe Species 0.000 claims 1
- 241000607534 Aeromonas Species 0.000 claims 1
- 241000588986 Alcaligenes Species 0.000 claims 1
- 235000003276 Apios tuberosa Nutrition 0.000 claims 1
- 244000105624 Arachis hypogaea Species 0.000 claims 1
- 235000010777 Arachis hypogaea Nutrition 0.000 claims 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims 1
- 241000589151 Azotobacter Species 0.000 claims 1
- 241000193830 Bacillus <bacterium> Species 0.000 claims 1
- 244000056139 Brassica cretica Species 0.000 claims 1
- 235000003351 Brassica cretica Nutrition 0.000 claims 1
- 240000002791 Brassica napus Species 0.000 claims 1
- 235000003343 Brassica rupestris Nutrition 0.000 claims 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims 1
- 244000020518 Carthamus tinctorius Species 0.000 claims 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims 1
- 102000005575 Cellulases Human genes 0.000 claims 1
- 108010084185 Cellulases Proteins 0.000 claims 1
- 241000190831 Chromatium Species 0.000 claims 1
- 244000060011 Cocos nucifera Species 0.000 claims 1
- 235000013162 Cocos nucifera Nutrition 0.000 claims 1
- 241000186216 Corynebacterium Species 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 claims 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 1
- 241000589565 Flavobacterium Species 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 1
- 235000010469 Glycine max Nutrition 0.000 claims 1
- 241000219146 Gossypium Species 0.000 claims 1
- 241000205062 Halobacterium Species 0.000 claims 1
- CODXQVBTPQLAGA-UHFFFAOYSA-N Hydroxydecanoate Chemical compound CCCCCCCCCC(=O)OO CODXQVBTPQLAGA-UHFFFAOYSA-N 0.000 claims 1
- 240000006240 Linum usitatissimum Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 244000061176 Nicotiana tabacum Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 241000187654 Nocardia Species 0.000 claims 1
- 240000007817 Olea europaea Species 0.000 claims 1
- 102000035195 Peptidases Human genes 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- 241000316848 Rhodococcus <scale insect> Species 0.000 claims 1
- 235000004443 Ricinus communis Nutrition 0.000 claims 1
- 244000000231 Sesamum indicum Species 0.000 claims 1
- 235000003434 Sesamum indicum Nutrition 0.000 claims 1
- 244000061456 Solanum tuberosum Species 0.000 claims 1
- 235000002595 Solanum tuberosum Nutrition 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- 241000187747 Streptomyces Species 0.000 claims 1
- 241000736901 Thiocystis Species 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 241000589651 Zoogloea Species 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 238000003483 aging Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- 239000013043 chemical agent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000010411 cooking Methods 0.000 claims 1
- 235000005822 corn Nutrition 0.000 claims 1
- 238000005336 cracking Methods 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003599 detergent Substances 0.000 claims 1
- 229940120124 dichloroacetate Drugs 0.000 claims 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000006266 etherification reaction Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 235000004426 flaxseed Nutrition 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- GLAYRDYYNSCSPO-UHFFFAOYSA-N heptaneperoxoic acid Chemical compound CCCCCCC(=O)OO GLAYRDYYNSCSPO-UHFFFAOYSA-N 0.000 claims 1
- -1 hydratases Proteins 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 1
- 229940041033 macrolides Drugs 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 235000010460 mustard Nutrition 0.000 claims 1
- 239000012434 nucleophilic reagent Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- UQGPCEVQKLOLLM-UHFFFAOYSA-N pentaneperoxoic acid Chemical compound CCCCC(=O)OO UQGPCEVQKLOLLM-UHFFFAOYSA-N 0.000 claims 1
- 108010081808 poly(3-hydroxyalkanoic acid) depolymerase Proteins 0.000 claims 1
- 108010010718 poly(3-hydroxyalkanoic acid) synthase Proteins 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000003825 pressing Methods 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 230000009467 reduction Effects 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 238000006884 silylation reaction Methods 0.000 claims 1
- 235000020238 sunflower seed Nutrition 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 238000007079 thiolysis reaction Methods 0.000 claims 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- 238000012017 passive hemagglutination assay Methods 0.000 abstract 12
- 238000000926 separation method Methods 0.000 abstract 1
Abstract
Cette invention concerne des procédés permettant d'extraire des polyhydroxyalkanoates ('PHA') de végétaux tels que des plantes oléagineuses transgéniques. Ces procédés permettent avantageusement de récupérer à la fois les PHA et l'huile de la biomasse végétale. Dans une réalisation, afin d'isoler les PHA, on prétraite une biomasse dérivée d'une plante oléagineuse, par exemple en procédant à la mouture, l'écrasement ou l'aplatissement par rouleau. Puis on extrait l'huile de la biomasse en utilisant un premier solvant dans lequel l'huile est soluble et dans lequel les PHA ne sont pas fortement solubles de façon à extraire l'huile. On peut ensuite extraire la biomasse en utilisant un second solvant dans lequel le PHA est soluble, de façon à séparer PHA et biomasse. Une autre possibilité consiste à traiter la biomasse contenant les PHA avec un agent chimique ou biochimique, tel qu'un enzyme, de manière à transformer chimiquement le PHA en un dérivé de PHA. On extrait ensuite ce dérivé de PHA du mélange au moyen, par exemple, d'un processus de séparation physique du type distillation, extraction ou chromatographie. La mise en oeuvre de ce procédé permet, avantageusement, d'extraire et de purifier, à grande échelle, les huiles végétales, les PHA et dérivés de PHA, de végétaux contenant de l'huile tels que des végétaux oléagineux transgéniques.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU74663/96A AU722033B2 (en) | 1995-10-26 | 1996-10-23 | Methods for isolating polyhydroxyalkanoates from plants |
| EP96936839A EP0859858B1 (fr) | 1995-10-26 | 1996-10-23 | Procedes d'extraction de polyhydroxyalkanoates a partir de vegetaux |
| DE69637253T DE69637253T2 (de) | 1995-10-26 | 1996-10-23 | Verfahren zur isolierung von polyhydroxyalkanoaten aus pflanzen |
| JP51672197A JP2001517070A (ja) | 1995-10-26 | 1996-10-23 | 植物からポリヒドロキシアルカノエートを単離する方法 |
| CA 2234965 CA2234965C (fr) | 1995-10-26 | 1996-10-23 | Procedes d'extraction de polyhydroxyalkanoates a partir de vegetaux |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US548,840 | 1995-10-26 | ||
| US08/548,840 US6083729A (en) | 1995-10-26 | 1995-10-26 | Methods for isolating polyhydroxyalkanoates from plants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1997015681A1 WO1997015681A1 (fr) | 1997-05-01 |
| WO1997015681B1 true WO1997015681B1 (fr) | 1997-06-19 |
| WO1997015681A9 WO1997015681A9 (fr) | 1997-07-17 |
Family
ID=24190604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/016921 WO1997015681A1 (fr) | 1995-10-26 | 1996-10-23 | Procedes d'extraction de polyhydroxyalkanoates a partir de vegetaux |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6083729A (fr) |
| EP (1) | EP0859858B1 (fr) |
| JP (4) | JP2001517070A (fr) |
| AT (1) | ATE373722T1 (fr) |
| AU (1) | AU722033B2 (fr) |
| DE (1) | DE69637253T2 (fr) |
| WO (1) | WO1997015681A1 (fr) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6083729A (en) * | 1995-10-26 | 2000-07-04 | Metabolix, Inc. | Methods for isolating polyhydroxyalkanoates from plants |
| US6087471A (en) * | 1997-04-15 | 2000-07-11 | Monsanto Company | High temperature PHA extraction using PHA-poor solvents |
| AU6971598A (en) * | 1997-04-15 | 1998-11-11 | Monsanto Company | Methods of pha extraction and recovery using non-halogenated solvents |
| DK1045642T3 (da) | 1998-01-07 | 2003-03-03 | Metabolix Inc | Dyrefodersammensætninger |
| US6586658B1 (en) | 1998-03-06 | 2003-07-01 | Metabolix, Inc. | Modification of fatty acid metabolism in plants |
| CA2327086A1 (fr) | 1998-04-08 | 1999-10-14 | Daniel M. Horowitz | Procedes pour la separation et la purification des biopolymeres |
| US6228934B1 (en) | 1998-06-09 | 2001-05-08 | Metabolix, Inc. | Methods and apparatus for the production of amorphous polymer suspensions |
| WO2000004895A2 (fr) | 1998-07-22 | 2000-02-03 | Metabolix, Inc. | Utilisations nutritionnelles et therapeutiques d'oligomeres de 3-hydroxyalcanoate |
| DE69938105T2 (de) | 1998-08-04 | 2009-01-29 | Metabolix, Inc., Cambridge | Herstellung von polyhydroxyalkanoaten aus polyolen |
| EP1867348B1 (fr) | 1999-03-25 | 2012-05-16 | Metabolix, Inc. | Dispositifs médicaux et applications de polymères polyhydroxyalkanoates |
| ATE292188T1 (de) * | 1999-05-12 | 2005-04-15 | Metabolix Inc | Verfahren zur reinigung von polyhydroxyalkanoaten |
| US6451564B1 (en) | 1999-07-02 | 2002-09-17 | Massachusetts Institute Of Technology | Methods for producing L-isoleucine |
| CA2383011C (fr) * | 1999-09-14 | 2008-07-22 | Tepha, Inc. | Utilisations therapeutiques de polymeres et d'oligomeres a base de gamma-hydroxybutyrate (ghb) |
| DE10013514C2 (de) * | 2000-03-14 | 2002-06-27 | Ufz Leipzighalle Gmbh | Verfahren zur Gewinnung von Polyhydroxyalkanoaten (PHA) oder deren Copolymeren |
| US20020077269A1 (en) * | 2000-10-27 | 2002-06-20 | Whitehouse Robert S. | Alkanoic acid ester monomer compositions and methods of making same |
| JP3768799B2 (ja) * | 2000-10-30 | 2006-04-19 | キヤノン株式会社 | 置換脂肪酸エステル化物を原料とするポリヒドロキシアルカノエートの製造方法 |
| AU2003259112A1 (en) * | 2002-07-12 | 2004-02-02 | The Texas A And M University System | Enzymatic process for the preparation of foods, feedstuffs and ingredients therefor |
| BR0313251A (pt) * | 2002-08-06 | 2005-07-05 | Metabolix Inc | Métodos de extração de polìmero |
| ATE518932T1 (de) * | 2003-02-21 | 2011-08-15 | Metabolix Inc | Pha-mischungen |
| US7781539B2 (en) * | 2003-02-21 | 2010-08-24 | Metabolix Inc. | PHA blends |
| ES2527857T3 (es) | 2003-05-08 | 2015-01-30 | Tepha, Inc. | Tejidos y fibras médicas de polihidroxialcanoato |
| US7579176B2 (en) | 2003-10-15 | 2009-08-25 | Newlight Technologies, Llc | Method for the production of polyhydroxyalkanoic acid |
| US8735113B2 (en) | 2003-10-15 | 2014-05-27 | Newlight Technologies, Llc | Methods and systems for production of polyhydroxyalkanoate |
| US7745197B1 (en) | 2003-10-15 | 2010-06-29 | Newlight Technologies, Llc | Process for the utilization of ruminant animal methane emissions |
| WO2005121207A2 (fr) * | 2004-06-11 | 2005-12-22 | Canon Kabushiki Kaisha | Polyhydroxyalcanoate comportant un groupe vinyle, un groupe ester, un groupe carboxyle et un groupe sulfonique, et procédé de production de ce composé |
| JP4455413B2 (ja) * | 2004-06-11 | 2010-04-21 | キヤノン株式会社 | ビニル基、エステル基、カルボキシル基並びにスルホン酸基を有するポリヒドロキシアルカン酸並びにその製造方法 |
| WO2005121204A2 (fr) * | 2004-06-11 | 2005-12-22 | Canon Kabushiki Kaisha | Acide polyhydroxyalcanoïque comportant un groupe vinyle, ester, carboxyle ou acide sulfonique et procédé de production de cet acide |
| JP4741883B2 (ja) * | 2004-06-11 | 2011-08-10 | キヤノン株式会社 | エステル基、カルボキシル基並びにスルホン酸基を有するポリヒドロキシアルカノエート並びにその製造方法 |
| ES2362217T3 (es) | 2004-08-03 | 2011-06-29 | Tepha, Inc. | Suturas de polihidroxialcanoato no rizadas. |
| CA2581458A1 (fr) * | 2006-03-22 | 2007-09-22 | National Research Council Of Canada | Methode de production de poly-.beta.-hydroxybutyrate |
| US8377151B2 (en) * | 2006-07-19 | 2013-02-19 | Zackery Allen McMurry | Process for producing a renewable biofuel from waste water treatment plants |
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-
1995
- 1995-10-26 US US08/548,840 patent/US6083729A/en not_active Expired - Lifetime
-
1996
- 1996-10-23 DE DE69637253T patent/DE69637253T2/de not_active Expired - Lifetime
- 1996-10-23 EP EP96936839A patent/EP0859858B1/fr not_active Expired - Lifetime
- 1996-10-23 AT AT96936839T patent/ATE373722T1/de not_active IP Right Cessation
- 1996-10-23 JP JP51672197A patent/JP2001517070A/ja not_active Withdrawn
- 1996-10-23 WO PCT/US1996/016921 patent/WO1997015681A1/fr active IP Right Grant
- 1996-10-23 AU AU74663/96A patent/AU722033B2/en not_active Expired
-
2000
- 2000-06-12 US US09/591,739 patent/US6709848B1/en not_active Expired - Lifetime
-
2007
- 2007-06-06 JP JP2007151037A patent/JP2007277574A/ja not_active Withdrawn
-
2008
- 2008-07-10 JP JP2008180815A patent/JP4422776B2/ja not_active Expired - Fee Related
-
2009
- 2009-02-27 JP JP2009045960A patent/JP2009112315A/ja not_active Ceased
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