HRP20211740T1 - Postupak za pretvaranje lignoceluloznih materijala u korisne kemikalije - Google Patents
Postupak za pretvaranje lignoceluloznih materijala u korisne kemikalije Download PDFInfo
- Publication number
- HRP20211740T1 HRP20211740T1 HRP20211740TT HRP20211740T HRP20211740T1 HR P20211740 T1 HRP20211740 T1 HR P20211740T1 HR P20211740T T HRP20211740T T HR P20211740TT HR P20211740 T HRP20211740 T HR P20211740T HR P20211740 T1 HRP20211740 T1 HR P20211740T1
- Authority
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- Prior art keywords
- mixture
- temperature
- reactor
- catalyst composition
- dialkyl
- Prior art date
Links
- 239000012978 lignocellulosic material Substances 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 4
- 239000000126 substance Substances 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims 12
- 239000007788 liquid Substances 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- -1 alkyl pyridinium organic cation Chemical class 0.000 claims 3
- 239000003610 charcoal Substances 0.000 claims 3
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000007790 solid phase Substances 0.000 claims 2
- 239000012855 volatile organic compound Substances 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000002608 ionic liquid Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/02—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
- C10B53/00—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form
- C10B53/02—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form of cellulose-containing material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
- C10B7/00—Coke ovens with mechanical conveying means for the raw material inside the oven
- C10B7/10—Coke ovens with mechanical conveying means for the raw material inside the oven with conveyor-screws
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
- C10G1/083—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts in the presence of a solvent
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
- C10G1/086—Characterised by the catalyst used
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
- C10G2300/1014—Biomass of vegetal origin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Processing Of Solid Wastes (AREA)
- Compounds Of Unknown Constitution (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (3)
1. Postupak pretvaranja čestičnog lignoceluloznog materijala za stvaranje hlapljivih organskih spojeva i drvenog ugljena, koji obuhvaća,
stvaranje smjese od čestičnog lignoceluloznog materijala s katalizatorskim sastavom koji sadrži polarnu organsku tekućinu i kiselinu,
zagrijavanje smjese do dovoljno visoke temperature i za dovoljno dugo razdoblje kako bi pretvorio glavni udio od bilo koje preostale čvrste faze smjese u drveni ugljen, pritom miješajući smjesu i odvajajući hlapljive organske spojeve i katalizatorski sastav od čvrste faze;
pri čemu je polarna organska tekućina odabrana iz ionskih tekućina sobne temperature imajući opću formulu AxMy, gdje je A organski kation dialkil imidazolij ili alkil piridinij i M je halid, sulfat, format, acetat, trifluorometansulfonat ili bis (trifluorometan) sulfonamid, i x i y su cijeli brojevi, ili
polarna organska tekućina je dipolarna aprotična tekućina izabrana iz dialkil formamida, N-alkil morfolin oksida, dialkil sulfoksida ili dialkil sulfona imajući opću kemijsku formulu R1 -SO2-R2, gdje su R1 i R2 alkilne grupe koje sadrže između jedan i deset atoma ugljika, uključujući ciklične sulfone u kojima R1 i R2 tvore dio cikličnog polimetilenskog prstena;
pri čemu je kiselina izabrana iz ortofosforne, sulfatne, metansulfonske, trifluorometansulfonske, hidrohalične i nitratne kiseline;
težina katalizatorskog sastava u smjesi je jedan do deset puta težine čestičnog lignoceluloznog materijala i pri čemu kiselina obuhvaća 0.1 do 10% težinskog udjela katalizatorskog sastava; i pri čemu
smjesa je odreagirala na temperaturu u području od 190°C do 500°C, pri čemu je zagrijavanje smjesa izvršeno u rotirajućem vijčanom reaktoru imajući ulaz za smjesu i izlaz za drveni ugljen u kojem je tlak održavan unutar područja 0.1 do 900 milibara s temperaturom u reaktoru kontroliranom duž reaktorove duljine tako da se temperatura reaktora povećava s niže temperature bliže ulazu prema višoj temperaturi bliže izlazu.
2. Postupak prema patentnom zahtjevu 1, pri čemu je tlak unutar rotirajućeg vijčanog reaktora održavan unutar područja 50 do 150 milibara.
3. Postupak prema patentnom zahtjevu 1 i patentnom zahtjevu 2, pri čemu polarna organska tekućina je tetrametilen sulfon.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2009903060A AU2009903060A0 (en) | 2009-07-01 | Method for Converting Lignocellulosic Materials into useful Chemicals | |
PCT/AU2010/000811 WO2011000030A1 (en) | 2009-07-01 | 2010-06-29 | Method for converting lignocellulosic materials into useful chemicals |
EP10793418.4A EP2449057B1 (en) | 2009-07-01 | 2010-06-29 | Method for converting lignocellulosic materials into useful chemicals |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20211740T1 true HRP20211740T1 (hr) | 2022-02-04 |
Family
ID=43410355
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20211740TT HRP20211740T1 (hr) | 2009-07-01 | 2010-06-29 | Postupak za pretvaranje lignoceluloznih materijala u korisne kemikalije |
Country Status (20)
Country | Link |
---|---|
US (1) | US9505985B2 (hr) |
EP (1) | EP2449057B1 (hr) |
JP (1) | JP5773279B2 (hr) |
KR (1) | KR101685229B1 (hr) |
CN (1) | CN102471694B (hr) |
AU (1) | AU2010268754B2 (hr) |
BR (1) | BRPI1014004B1 (hr) |
CA (1) | CA2764865C (hr) |
DK (1) | DK2449057T3 (hr) |
ES (1) | ES2887589T3 (hr) |
HR (1) | HRP20211740T1 (hr) |
IL (1) | IL217299A (hr) |
MX (1) | MX2011013425A (hr) |
MY (1) | MY159096A (hr) |
NZ (1) | NZ597803A (hr) |
PL (1) | PL2449057T3 (hr) |
PT (1) | PT2449057T (hr) |
SG (2) | SG176971A1 (hr) |
SI (1) | SI2449057T1 (hr) |
WO (1) | WO2011000030A1 (hr) |
Families Citing this family (36)
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JP5888246B2 (ja) * | 2011-01-28 | 2016-03-16 | 三菱化学株式会社 | 2−フルアルデヒドの製造方法 |
CN102298364B (zh) * | 2011-05-10 | 2013-03-27 | 沈阳新一代信息技术有限公司 | 拌和站电控系统及控制方法 |
JP2014517052A (ja) * | 2011-06-22 | 2014-07-17 | ビーエーエスエフ ソシエタス・ヨーロピア | 炭水化物含有組成物を脱水するための方法 |
EP2782897A4 (en) | 2011-11-23 | 2015-06-24 | Segetis Inc | PROCESS FOR PREPARING LÄVULINIC ACID |
US9181210B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Processes for making furfurals |
CN104039772B (zh) | 2011-12-28 | 2016-06-29 | 纳幕尔杜邦公司 | 用于制备糠醛的方法 |
CA2859996A1 (en) | 2011-12-28 | 2013-07-04 | Paul Joseph Fagan | Process for the production of furfural |
WO2013102027A1 (en) | 2011-12-28 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of furfural |
CN102634229B (zh) * | 2012-04-13 | 2013-08-14 | 蔡家俊 | 螺旋输送机与挤压机相结合生产粉末焦糖色素的方法 |
US9073841B2 (en) | 2012-11-05 | 2015-07-07 | Segetis, Inc. | Process to prepare levulinic acid |
EP2759597A1 (en) * | 2013-01-23 | 2014-07-30 | Sekab E-Technology AB | Image analysis based process control of processes for production of sugar from lignocellulosic biomass |
NZ743055A (en) * | 2013-03-08 | 2020-03-27 | Xyleco Inc | Equipment protecting enclosures |
US10442995B2 (en) | 2013-03-15 | 2019-10-15 | Gas Technology Institute | Rapid production of hydrothermally carbonized biomass via reactive twin-screw extrusion |
US10590359B2 (en) | 2013-03-15 | 2020-03-17 | Gas Technology Institute | Hydrothermally carbonized biomass formed via reactive twin-screw extrusion |
US9920251B2 (en) * | 2013-03-15 | 2018-03-20 | Terry Karanikas | Pyrolysis apparatus and method |
WO2016039996A1 (en) * | 2014-09-11 | 2016-03-17 | E. I. Du Pont De Nemours And Company | Production of levoglucosenone |
CA2964210C (en) | 2014-10-15 | 2023-09-12 | Licella Pty Ltd | Integrated kraft pulp mill and thermochemical conversion system |
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WO2016100028A1 (en) | 2014-12-16 | 2016-06-23 | E. I. Du Pont De Nemours And Company | Process for producing levoglucosenone |
GB201506701D0 (en) | 2015-04-20 | 2015-06-03 | Univ York | Method for converting waste lignocellulosic materials derived from converting lignocellulose to ethanol into levoglucosenone |
EP3337873B1 (en) * | 2015-08-17 | 2020-10-28 | Gas Technology Institute | Hydrothermally carbonized biomass formed via reactive twin-screw extrusion |
EP3353225B1 (en) | 2015-09-25 | 2023-05-10 | Huntsman Advanced Materials Licensing (Switzerland) GmbH | Preparation of polyamidoimides |
US10465120B1 (en) * | 2016-09-12 | 2019-11-05 | Michael Garjian | Method and device with catalyst storage and delivery capsule for converting biomass into solid and gaseous components |
CN106928285B (zh) * | 2017-02-21 | 2022-02-08 | 华北电力大学 | 一种生物质催化热解制备左旋葡萄糖酮的方法 |
ES2785648T3 (es) * | 2017-10-11 | 2020-10-07 | Energies Termiques Basiques Sl | Método para tratamiento de biomasa de residuos agrícolas lignocelulósicos y/o residuos que contienen grupos funcionales fenólicos |
CN107759544A (zh) * | 2017-10-11 | 2018-03-06 | 肥城金威机械有限公司 | 用于糠醛的水解方法、装置及其应用 |
CN108249174B (zh) * | 2017-12-25 | 2019-10-22 | 格林美(无锡)能源材料有限公司 | 一种物料输送及投料系统的工作方法 |
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2010
- 2010-06-29 PT PT107934184T patent/PT2449057T/pt unknown
- 2010-06-29 MY MYPI2011006365A patent/MY159096A/en unknown
- 2010-06-29 MX MX2011013425A patent/MX2011013425A/es active IP Right Grant
- 2010-06-29 CA CA2764865A patent/CA2764865C/en active Active
- 2010-06-29 JP JP2012516439A patent/JP5773279B2/ja active Active
- 2010-06-29 BR BRPI1014004-2A patent/BRPI1014004B1/pt active IP Right Grant
- 2010-06-29 ES ES10793418T patent/ES2887589T3/es active Active
- 2010-06-29 SG SG2011095635A patent/SG176971A1/en unknown
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EP2449057A1 (en) | 2012-05-09 |
MX2011013425A (es) | 2012-04-11 |
KR101685229B1 (ko) | 2016-12-09 |
SI2449057T1 (sl) | 2021-11-30 |
US20120111714A1 (en) | 2012-05-10 |
AU2010268754A1 (en) | 2012-02-09 |
DK2449057T3 (da) | 2021-11-08 |
PT2449057T (pt) | 2021-09-10 |
IL217299A0 (en) | 2012-02-29 |
EP2449057A4 (en) | 2013-03-06 |
CN102471694A (zh) | 2012-05-23 |
WO2011000030A1 (en) | 2011-01-06 |
BRPI1014004A2 (pt) | 2019-04-09 |
SG176971A1 (en) | 2012-02-28 |
IL217299A (en) | 2017-02-28 |
JP2012531477A (ja) | 2012-12-10 |
ES2887589T3 (es) | 2021-12-23 |
KR20120106711A (ko) | 2012-09-26 |
EP2449057B1 (en) | 2021-08-11 |
AU2010268754B2 (en) | 2015-11-05 |
MY159096A (en) | 2016-12-15 |
CA2764865A1 (en) | 2011-01-06 |
BRPI1014004B1 (pt) | 2020-10-27 |
PL2449057T3 (pl) | 2022-01-24 |
US9505985B2 (en) | 2016-11-29 |
JP5773279B2 (ja) | 2015-09-02 |
NZ597803A (en) | 2013-08-30 |
SG10201403520SA (en) | 2014-10-30 |
CN102471694B (zh) | 2014-06-04 |
CA2764865C (en) | 2017-04-25 |
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