WO1997015681B1 - Methods for isolating polyhydroxyalkanoates from plants - Google Patents
Methods for isolating polyhydroxyalkanoates from plantsInfo
- 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
Methods are provided for separating polyhydroxyalkanoates ('PHAs') from plants, such as transgenic oil crop plants. The methods advantageously permit both the oil and the PHAs to be recovered from the plant biomass. To isolate the PHAs, in one embodiment, a biomass derived from an oil crop plant is pre-processed, for example by grinding, crushing or rolling. The oil then is extracted from the biomass with a first solvent in which the oil is soluble and in which the PHAs are not highly soluble to remove the oil. The biomass then can be extracted with a second solvent in which the PHA is soluble, to separate the PHA from the biomass. Alternatively, the PHA-containing biomass is treated with a chemical or biochemical agent, such as an enzyme, to chemically transform the PHA into a PHA derivative. The PHA derivative then is separated from the mixture using, for example, a physical separation process such as distillation, extraction or chromatography. Advantageously, using the method, the plant oils, the PHAs and PHA derivatives can be recovered and purified on a large scale from oil containing plants such as transgenic oil crop plants.
Claims
1. A method for separating a polyhydroxy alkanoate ("PHA") from a plant biomass comprising plant oil and meal, the method comprising extracting the plant biomass with a first solvent to essentially remove the oil from the biomass, and then separating the PHA from the plant biomass.
2. The method of claim 1 wherein the plant biomass is derived from a transgenic plant.
3. The method of claim 1 further comprising derivatizing the PHA prior to separating the PHA from the biomass.
4. The method of claim 1 wherein the separated PHA comprises one or more units having the formula:
-OCR'R^CR^CO- wherein n is 0 or an integer; and wherein R1, R2, R\ and R4 each are independently selected from the group consisting of hydrocarbon-radicals, halo- and hydroxy-substituted radicals, hydroxy radicals, halogen radicals, nitrogen-substituted radicals, oxygen-substituted radicals and hydrogen atoms.
5. The method of claim 4 wherein the separated PHA is selected from the group consisting of monomers, dimers, linear and cyclic oligomers, and lactones of the units.
6. The method of claim 3 wherein the separated PHA is selected from the group consisting of esters defined by the formula: HOCR'R2(CR3R4)nCO2R5; amides defined by the formula: HOCR1R2(CR3R4)nCONR5R6; thioesters defined by the formula: HOCR1R2(CR3R4)nCOSR5; acids defined by the formula: HOCR1R2(CR3R4)nCO2H; ethers defined by the formula: R6OCR1R2(CR3R4)nCO2R5; esters defined by the formula: R6CO2CR1R2(CR3R4)nCO2R5; unsaturated compounds, defined by the formulas: - 30 -
R 'R2C=CR3(CR4R5)nCO2R6; and
R'R^CCCR4) =C(R5)CO2R6; diols defmed by the formula: HOCR1R2(CR3R4)nCH2OH; lactones or macrolides defined by the formula:
H -OCRlR2(CR3R4)„CO-K , wherein x is an integer; and ketones or aldehydes defined by the formulas:
HOCR'R2(CR3R4)nCOR5;
HOCR1R2(CR3R4)nCHO;
R'CO(CR2R3)nCOOR4; and
R1CO(CR2R3)nCOR4; wherein n is 0 or an integer; and wherein Rl, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of hydrocarbon radicals, halo- and hydroxy-substituted radicals, hydroxy radicals, halogen radicals, nitrogen-substituted radicals, oxygen-substituted radicals, and hydrogen atoms.
7. The method of claim 1 comprising a) providing a plant biomass containing a PHA; b) pre-processing the plant biomass to obtain a mixture containing PHA, oil and plant meal; c) extracting oil from the mixture with a first solvent at a temperature at which the oil is soluble and in which the PHA is not highly soluble, to obtain a residual meal mixture comprising PHA; and d) extracting the residual meal mixture obtained in step c) with a second solvent in which the PHA is soluble, to separate PHA from the biomass.
8. The method of claim 1 comprising: a) providing a plant biomass containing a PHA; b) pre-processing the plant biomass to produce a mixture containing PHA, oil and plant meal; c) extracting oil from the mixture with a first solvent at a temperature at which the oil is soluble and in which the PHA is not highly soluble, to obtain a residual meal mixture comprising PHA; d) treating the residual meal mixture comprising PHA, obtained in step c), with at least one chemical or biochemical agent, to chemically derivatize the PHA; and e) separating derivatized PHA from the residual meal mixture obtained in step d).
9. The method of claim 7 or 8 wherein step b) comprises pre¬ processing the plant biomass using one or more processes selected from the group consisting of drying, dehulling, cleaning, ageing, cleaning, weighing, cracking, flaking, pressing, rolling, grinding, cooking, crushing, settling, filtering, washing, centrifugal fractionation, and air classification.
10. The method of claim 7 wherein the second solvent is selected from the group consisting of a chlorinated organic solvent, an alkyl carbonate, an alcohol, a hydroxyacid, acetic acid, and mixtures thereof.
11. The method of claim 10 wherein the second solvent comprises a chloronated organic solvent selected from the group consisting of chloroform, methylene chloride, dichloroethane, trichloroethane, tetrachloroethane and dichloroacetate. - 32 -
12. The method of claim 7 wherein the second solvent comprises a composition selected from the group consisting of a propylene carbonate, ethylene carbonate, trifluoroethanol, acetic anhydride, acetic acid, dimethylformamide, ethylacetoacetate, triolein, toluene, dioxane, tetrahydrofuran, diethylether, pyridine, and alcohols having more than three carbon atoms.
13. The method of claim 8 wherein, in step d), the residual meal mixture comprising PHA is treated with at least one chemical agent selected from the group consisting of acids, bases, detergents, oxidizing agents, chelating agents, reducing agents, nucleophilic reagents, electrophilic reagents, metal ions, and free radicals.
14. The method of claim 8 wherein the PHA is derivatized by a chemical transformation selected from the group consisting of esterification, transesterification, hydrolysis, saponif ication, aminolysis, thiolysis, etherification, silylation, addition, elimination, rearrangement, reduction, and condensation.
15. The method of claim 8 wherein the biochemical agent is an enzyme.
16. The method of claim 15 wherein the enzyme is selected from the group consisting of a depolymerase, protease, nuclease, lipase, phosphorylase and a glycosidase.
17. The method of claim 8 wherein, in step e), the derivatized PHA is separated by a physical process selected from the group consisting of distillation, extraction, centrifugation, filtration, evaporation, and chromatography.
18. The method of claim 7 or 8 wherein the first and second solvents each have boiling points between 30 'C and 250' C.
19. The method of claim 7 or 8 further comprising precipitating the separated PHA derivative. 33 -
20. The method of claim 1 wherein the biomass is derived from a plant source selected from the group consisting of soybean, cotton, coconuts, groundnuts, rapeseed, sunflower seed, olive, palm, sesame seed, linseed, castor, safflower seed, tobacco, corn, mustard, and potato.
21. The method of claim 4 wherein the separated PHA includes one or more of the same or different units selected from the group consisting of hydroxy butyrate, hydroxyvalerate, hydroxy hexanoate, hydroxy heptanoate, hydroxy octanoate, hydroxynonanoate, and hydroxy decanoate .
22. The method of claim 8 wherein the separated PHA is selected from the group consisting of 3-hydroxybutyric acid, 4- hydroxybutyric acid, crotonic acid and alkyl esters thereof.
23. The method of claim 2 wherein the plant biomass is derived from a plant containing a heterologous PHA synthase gene derived from a microorganism selected from the group consisting of Acinetobacter, Aeromonas, Alcaligenes, Azotobacter, Bacillus, Brevibacteriwn, Corynebacterium, Chromatium, Flavobacterium, Halobacterium, Pseudomonads, Nocardia, Rhodococcus, Thiocystis, Streptomyces, Streptococcus and Zoogloea.
24. A method for separating a polyhydroxyalkanoate ("PHA") from a plant biomass comprising plant oil, the method comprising extracting a plant biomass with a first solvent at a temperature at which the oil and PHA are soluble, to essentially remove oil and PHA from the biomass, and then separating PHA from the oil.
25. The method of claim 24 wherein the plant biomass is derived from a transgenic oil crop plant.
26. The method of claim 25 wherein the method comprises a) providing a plant biomass containing a PHA; b) pre-processing the plant biomass to obtain a mixture of PHA, oil and plant meal; - 34 -
c) extracting oil and PHA from the mixture with a first solvent in which the oil and the PHA are soluble and in which the meal is not highly soluble; and d) separating the PHA from the oil.
27. The method of claim 26 wherein the PHA is separated from the oil in step d) by treating the PHA-oil mixture with a chemical or biochemical agent, thereby to chemically derivatize the PHA, and separating derivatized PHA from the oil.
28. The method of claim 26 wherein the solvent is selected from the group consisting of a chlorinated organic solvent, an alkylcarbonate, an alcohol, a hydroxyacid and a hydrocarbon, and mixtures thereof.
29. The method of claim 26 wherein the solvent is selected from the group consisting of hexane, trifluoroethanol, acetic anhydride, dimethylformamide, ethylacetoacetate, triolein, acetic acid, toluene, dioxane, tetrahydrofuran, diethylether and pyridine.
30. The method of claim 27 wherein the biochemical agent is an enzyme selected from the group consisting of PHA depolymerases, proteases, nucleases, lipases, hydratases, phosphorylases, cellulases and glycosidases.
31. The method of claim 7, 8, 26 or 27 wherein the separated PHA includes a functional group selected from the group consisting of amides, thioesters, acids, ethers, esters, unsaturated compounds, diols, ketones and aldehydes.
32. The method of claim 7, 8, 26 or 27 wherein the separated PHA includes one or more units selected from the group consisting of a 3-hydroxyacid, a 4-hydroxyacid and a 5-hydroxyacid.
33. The method of claim 7 or 26 wherein the separated PHA is separated in an organic solvent; and wherein the method further comprises: - 35
emulsifying the PHA in the organic solvent in an aqueous solution containing a surfactant, thereby to form a PHA latex.
34. The method of claim 7 or 26 wherein the separated PHA is separated in an organic solvent and wherein the method further comprises emulsifying the PHA in the organic solvent in an aqueous solution and removing the solvent thereby forming a PHA latex.
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 (en) | 1995-10-26 | 1996-10-23 | Methods for isolating polyhydroxyalkanoates from plants |
| DE69637253T DE69637253T2 (en) | 1995-10-26 | 1996-10-23 | PROCESS FOR THE ISOLATION OF POLYHYDROXYALKANOATES FROM PLANTS |
| JP51672197A JP2001517070A (en) | 1995-10-26 | 1996-10-23 | Method for isolating polyhydroxyalkanoate from plants |
| CA 2234965 CA2234965C (en) | 1995-10-26 | 1996-10-23 | Methods for isolating polyhydroxyalkanoates from plants |
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 (en) | 1997-05-01 |
| WO1997015681B1 true WO1997015681B1 (en) | 1997-06-19 |
| WO1997015681A9 WO1997015681A9 (en) | 1997-07-17 |
Family
ID=24190604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/016921 WO1997015681A1 (en) | 1995-10-26 | 1996-10-23 | Methods for isolating polyhydroxyalkanoates from plants |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6083729A (en) |
| EP (1) | EP0859858B1 (en) |
| JP (4) | JP2001517070A (en) |
| AT (1) | ATE373722T1 (en) |
| AU (1) | AU722033B2 (en) |
| DE (1) | DE69637253T2 (en) |
| WO (1) | WO1997015681A1 (en) |
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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/en not_active Expired - Lifetime
- 1996-10-23 EP EP96936839A patent/EP0859858B1/en not_active Expired - Lifetime
- 1996-10-23 AT AT96936839T patent/ATE373722T1/en not_active IP Right Cessation
- 1996-10-23 JP JP51672197A patent/JP2001517070A/en not_active Withdrawn
- 1996-10-23 WO PCT/US1996/016921 patent/WO1997015681A1/en 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/en not_active Withdrawn
-
2008
- 2008-07-10 JP JP2008180815A patent/JP4422776B2/en not_active Expired - Fee Related
-
2009
- 2009-02-27 JP JP2009045960A patent/JP2009112315A/en not_active Ceased
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