RU2012135497A - Производство сбраживаемых сахаров и лигнина из биомассы, использующее сверхкритические текучие среды - Google Patents
Производство сбраживаемых сахаров и лигнина из биомассы, использующее сверхкритические текучие среды Download PDFInfo
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- 239000012530 fluid Substances 0.000 title claims abstract 31
- 229920005610 lignin Polymers 0.000 title claims abstract 10
- 239000002028 Biomass Substances 0.000 title claims abstract 9
- 238000000034 method Methods 0.000 claims abstract 40
- 230000007062 hydrolysis Effects 0.000 claims abstract 23
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 23
- 239000007788 liquid Substances 0.000 claims abstract 23
- 239000011159 matrix material Substances 0.000 claims abstract 14
- 239000007787 solid Substances 0.000 claims abstract 14
- 238000002203 pretreatment Methods 0.000 claims abstract 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000001569 carbon dioxide Substances 0.000 claims abstract 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 4
- 239000008103 glucose Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N Xylose Natural products O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 3
- 239000000178 monomer Substances 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 229920001542 oligosaccharide Polymers 0.000 claims 1
- 238000000194 supercritical-fluid extraction Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- -1 xylose oligosaccharides Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
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- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/25—Component parts, details or accessories; Auxiliary operations
- B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
- B29C48/395—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders
- B29C48/40—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders using two or more parallel screws or at least two parallel non-intermeshing screws, e.g. twin screw extruders
- B29C48/41—Intermeshing counter-rotating screws
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/25—Component parts, details or accessories; Auxiliary operations
- B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
- B29C48/50—Details of extruders
- B29C48/505—Screws
- B29C48/535—Screws with thread pitch varying along the longitudinal axis
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/06—Ethanol, i.e. non-beverage
- C12P7/08—Ethanol, i.e. non-beverage produced as by-product or from waste or cellulosic material substrate
- C12P7/10—Ethanol, i.e. non-beverage produced as by-product or from waste or cellulosic material substrate substrate containing cellulosic material
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
- C13K1/04—Purifying
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/002—Xylose
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- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/007—Separation of sugars provided for in subclass C13K
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C3/00—Pulping cellulose-containing materials
- D21C3/22—Other features of pulping processes
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C1/00—Pretreatment of the finely-divided materials before digesting
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
- D21C11/0007—Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for
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- Y02E50/00—Technologies for the production of fuel of non-fossil origin
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- Y02P20/00—Technologies relating to chemical industry
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- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Processing Of Solid Wastes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1. Способ непрерывной обработки биомассы, включающий:стадию предварительной обработки, где указанная биомасса вступает в контакт с первой сверхкритической, околокритической или докритической текучей средой, образуя твердую матрицу и первую жидкую фракцию;где указанная первая сверхкритическая, околокритическая или докритическая текучая среда содержит воду и, необязательно, CO; игде указанная первая сверхкритическая, околокритическая или докритическая текучая среда практически не содержит спирта C-C; истадию гидролиза, где указанная твердая матрица вступает в контакт со второй сверхкритической или близкой к сверхкритической текучей средой, образуя вторую жидкую фракцию и нерастворимую содержащую лигнин фракцию;где указанная вторая сверхкритическая или околокритическая текучая среда содержит воду и, необязательно, CO; игде указанная вторая сверхкритическая или околокритическая текучая среда практически не содержит спиртов C-C.2. Способ по п.1, в котором указанная первая сверхкритическая, околокритическая или докритическая текучая среда содержит менее чем приблизительно 10% диоксида углерода.3. Способ по п.1, в котором указанная стадия предварительной обработки происходит при температуре и давлении ниже критической точки, по меньшей мере, одного компонента указанной первой сверхкритической, околокритической или докритической текучей среды.4. Способ по п.1, в котором указанную стадию предварительной обработки осуществляют при температуре, составляющей от приблизительно 150°C до приблизительно 300°C.5. Способ по п.1, в котором указанную стадию предварительной обработки осуществляют при давлении, составляющем �
Claims (36)
1. Способ непрерывной обработки биомассы, включающий:
стадию предварительной обработки, где указанная биомасса вступает в контакт с первой сверхкритической, околокритической или докритической текучей средой, образуя твердую матрицу и первую жидкую фракцию;
где указанная первая сверхкритическая, околокритическая или докритическая текучая среда содержит воду и, необязательно, CO2; и
где указанная первая сверхкритическая, околокритическая или докритическая текучая среда практически не содержит спирта C1-C5; и
стадию гидролиза, где указанная твердая матрица вступает в контакт со второй сверхкритической или близкой к сверхкритической текучей средой, образуя вторую жидкую фракцию и нерастворимую содержащую лигнин фракцию;
где указанная вторая сверхкритическая или околокритическая текучая среда содержит воду и, необязательно, CO2; и
где указанная вторая сверхкритическая или околокритическая текучая среда практически не содержит спиртов C1-C5.
2. Способ по п.1, в котором указанная первая сверхкритическая, околокритическая или докритическая текучая среда содержит менее чем приблизительно 10% диоксида углерода.
3. Способ по п.1, в котором указанная стадия предварительной обработки происходит при температуре и давлении ниже критической точки, по меньшей мере, одного компонента указанной первой сверхкритической, околокритической или докритической текучей среды.
4. Способ по п.1, в котором указанную стадию предварительной обработки осуществляют при температуре, составляющей от приблизительно 150°C до приблизительно 300°C.
5. Способ по п.1, в котором указанную стадию предварительной обработки осуществляют при давлении, составляющем от приблизительно 50 бар (5 МПа) до приблизительно 115 бар (11,5 МПа).
6. Способ по п.1, в котором указанная биомасса имеет время выдерживания от приблизительно 1 минуты до приблизительно 5 минут на указанной стадии предварительной обработки.
7. Способ по п.1, в котором, по меньшей мере, одну из указанной твердой матрицы и указанной первой жидкой фракции охлаждают до температуры ниже температуры указанной стадии предварительной обработки.
8. Способ по п.7, в котором, по меньшей мере, одну из указанной твердой матрицы и указанной первой жидкой фракции охлаждают до температуры от приблизительно 20°C до приблизительно 90°C.
9. Способ по п.1, дополнительно включающий первую стадию разделения после указанной стадии предварительной обработки и до указанной стадии гидролиза, в котором разделяют указанную твердую матрицу и указанную первую жидкую фракцию.
10. Способ по п.1, в котором указанная первая жидкая фракция содержит олигосахариды ксилозы.
11. Способ по п.1, в котором, по меньшей мере, одна из указанной стадии предварительной обработки и указанной стадии гидролиза является непрерывной.
12. Способ по п.1, в котором указанная вторая сверхкритическая или близкая к сверхкритической текучая среда не содержит кислоту.
13. Способ по п.1, в котором указанная твердая матрица имеет время выдерживания от приблизительно 1 секунды до приблизительно 30 секунд на указанной стадии гидролиза.
14. Способ по п.1, в котором указанная стадия гидролиза происходит при температуре и давлении выше критической точки, по меньшей мере, одного компонента указанной второй сверхкритической или околокритической текучей среды.
15. Способ по п.1, в котором указанная стадия гидролиза происходит при температуре от приблизительно 275°C до приблизительно 450°C.
16. Способ по п.1, в котором указанная стадия гидролиза происходит при давлении, составляющем от приблизительно 200 бар (20 МПа) до приблизительно 250 бар (25 МПа).
17. Способ по п.1, в котором указанную твердую матрицу выдерживают при температуре, составляющей от приблизительно 185°C или выше, от начала указанной стадии предварительной обработки, по меньшей мере, до окончания указанной стадии гидролиза.
18. Способ по п.1, дополнительно включающий охлаждение, по меньшей мере, одной из указанной лигниновой фракции и указанной второй жидкой фракции после указанной стадии гидролиза.
19. Способ по п.18, в котором, по меньшей мере, одну из указанной лигниновой фракции и указанной второй жидкой фракции охлаждают до температуры, составляющей от приблизительно 180°C до приблизительно 240°C,
20. Способ по п.19, дополнительно включающий мгновенное охлаждение, по меньшей мере, одной из указанной лигниновой фракции и указанной второй жидкой фракции.
21. Способ по п.1, дополнительно включающий вторую стадию разделения после указанной стадии гидролиза, в котором разделяют указанную лигниновую фракцию и указанную вторую жидкую фракцию.
22. Способ по п.1, дополнительно включающий:
вторую стадию гидролиза, где указанная вторая жидкая фракция вступает в контакт с третьей околокритической или докритической текучей средой, образуя третью жидкую фракцию, содержащую мономеры глюкозы;
в котором указанная третья околокритическая или докритическая текучая среда содержит воду и, необязательно, кислоту.
23. Способ по п.22, в котором указанная вторая стадия гидролиза происходит при температуре, составляющей от приблизительно 220°C до приблизительно 320°C.
24. Способ по п.22, в котором указанная вторая стадия гидролиза происходит при давлении, составляющем от приблизительно 30 бар (3 МПа) до приблизительно 90 бар (9 МПа).
25. Способ по п.22, в котором указанная вторая стадия гидролиза происходит при температуре, составляющей от приблизительно 240°C до приблизительно 300°C, и при давлении, составляющем от приблизительно 35 бар (3,5 МПа) до приблизительно 85 бар (8,5 МПа).
26. Способ по п.22, в котором указанная кислота присутствует в каталитическом количестве.
27. Способ по п.22, в котором указанная кислота присутствует в количество менее чем приблизительно 1%.
28. Способ по п.22, в котором указанная кислота выбрана из группы, которую составляют фтористоводородная кислота, соляная кислота, бромистоводородная кислота, йодистоводородная кислота, серная кислота, сульфоновая кислота, фосфорная кислота, фосфоновая кислота, азотная кислота, азотистая кислота и их сочетания.
29. Способ по п.22, в котором указанная вторая жидкая фракция имеет время выдерживания от приблизительно 1 секунды до приблизительно 30 секунд на указанной второй стадии гидролиза.
30. Способ по п.22, в котором, по меньшей мере, один продукт указанной второй стадии гидролиза затем охлаждают до температуры ниже температуры указанной второй стадии гидролиза.
31. Способ по п.22, в котором указанная третья жидкая фракция содержит гликолевый альдегид.
32. Способ по п.1, в котором давление, производимое на указанную твердую матрицу, уменьшается до приблизительно 105 кПа или менее после указанной стадии гидролиза.
33. Способ по п.1, дополнительно включающий, после указанной стадии гидролиза, уменьшение давления, производимого на указанную твердую матрицу, таким образом, что указанный лигнин осаждается.
34. Способ по п.1, дополнительно включающий:
стадию гидролиза ксилоолигосахаридов, где указанная первая жидкая фракция вступает в контакт с четвертой околокритической или докритической текучей средой, образуя четвертую жидкую фракцию, содержащую мономеры ксилозы;
в котором указанная четвертая околокритическая или докритическая текучая среда содержит воду и, необязательно, кислоту.
35. Способ обработки биомассы, включающий:
стадию предварительной обработки, где указанная биомасса вступает в контакт с первой сверхкритической, околокритической или докритической текучей средой, образуя предварительно обработанную суспензию, включающую твердую матрицу и первую жидкую фракцию, содержащую ксилоолигосахариды;
где указанная первая сверхкритическая, околокритическая или докритическая текучая среда содержит воду и, необязательно, CO2; и
где указанная первая сверхкритическая, околокритическая или докритическая текучая среда практически не содержит спирта C1-C5;
первую стадию разделения, где разделяют указанную твердую матрицу и указанную первую жидкую фракцию;
первую стадию гидролиза, где указанная твердая матрица вступает в контакт со второй сверхкритической или околокритической текучей средой, образуя нерастворимую содержащую лигнин фракцию и вторую жидкую фракцию, содержащую целлоолигосахариды;
где указанная вторая сверхкритическая или околокритическая текучая среда содержит воду и, необязательно, CO2; и
где указанная вторая сверхкритическая или околокритическая текучая среда практически не содержит спирта C1-C5;
вторую стадию разделения, где разделяют указанную нерастворимую содержащую лигнин фракцию и указанную вторую жидкую фракцию; и
вторую стадию гидролиза, где указанная вторая жидкая фракция вступает в контакт с третьей околокритической или докритической текучей средой, образуя продукт, содержащий мономеры глюкозы;
где указанная третья околокритическая или докритическая текучая среда содержит воду и, необязательно, кислоту.
36. Композиция, включающая:
глюкозу, составляющую, по меньшей мере, приблизительно 63 мас.% по отношению к суммарной массе композиции;
воду;
менее чем приблизительно 13,0 мас.% гликолевого альдегида по отношению к суммарной массе композиции;
менее чем приблизительно 2,0 мас.% гликолевой кислоты по отношению к суммарной массе композиции; и
в которой указанную глюкозу экстрагируют из биомассы, используя экстракцию сверхкритической текучей средой.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US10053745B2 (en) | 2010-01-19 | 2018-08-21 | Renmatix, Inc. | Production of fermentable sugars and lignin from biomass using supercritical fluids |
| US10858712B2 (en) | 2010-01-19 | 2020-12-08 | Renmatix, Inc. | Production of fermentable sugars and lignin from biomass using supercritical fluids |
| US9963555B2 (en) | 2011-12-30 | 2018-05-08 | Renmatix, Inc. | Compositions comprising lignin |
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| Publication number | Publication date |
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| US20180355447A1 (en) | 2018-12-13 |
| RU2015112569A (ru) | 2015-09-20 |
| BR112012017850A2 (pt) | 2016-04-19 |
| CN102859066B (zh) | 2016-01-13 |
| RU2597588C2 (ru) | 2016-09-10 |
| CN102859066A (zh) | 2013-01-02 |
| CA2815597A1 (en) | 2011-07-28 |
| CN105525043B (zh) | 2021-03-19 |
| US20160244852A1 (en) | 2016-08-25 |
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| US20130239954A1 (en) | 2013-09-19 |
| EP2526225B1 (en) | 2019-10-02 |
| CN112159869A (zh) | 2021-01-01 |
| EP2526225A4 (en) | 2017-07-26 |
| US8968479B2 (en) | 2015-03-03 |
| CN112159869B (zh) | 2024-04-19 |
| BR112012017850B1 (pt) | 2020-11-17 |
| CA2945277A1 (en) | 2011-07-28 |
| US20120291774A1 (en) | 2012-11-22 |
| WO2011091044A1 (en) | 2011-07-28 |
| RU2556496C2 (ru) | 2015-07-10 |
| US10858712B2 (en) | 2020-12-08 |
| US10053745B2 (en) | 2018-08-21 |
| CA2945277C (en) | 2021-01-05 |
| CA2769746A1 (en) | 2011-07-28 |
| EP2526225A1 (en) | 2012-11-28 |
| US9359651B2 (en) | 2016-06-07 |
| CN105525043A (zh) | 2016-04-27 |
| CA2815597C (en) | 2016-11-29 |
| CA2769746C (en) | 2013-10-15 |
| BR112012017850B8 (pt) | 2020-12-01 |
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