BR112012014736B1 - método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição - Google Patents
método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição Download PDFInfo
- Publication number
- BR112012014736B1 BR112012014736B1 BR112012014736A BR112012014736A BR112012014736B1 BR 112012014736 B1 BR112012014736 B1 BR 112012014736B1 BR 112012014736 A BR112012014736 A BR 112012014736A BR 112012014736 A BR112012014736 A BR 112012014736A BR 112012014736 B1 BR112012014736 B1 BR 112012014736B1
- Authority
- BR
- Brazil
- Prior art keywords
- isoprene
- solvent
- column
- weight
- gaseous effluent
- Prior art date
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- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims abstract description 907
- 238000000034 method Methods 0.000 title claims abstract description 168
- 239000000203 mixture Substances 0.000 title claims abstract description 152
- 238000000746 purification Methods 0.000 title claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 182
- 239000012535 impurity Substances 0.000 claims abstract description 170
- 239000006227 byproduct Substances 0.000 claims description 111
- 238000001179 sorption measurement Methods 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 47
- 150000002430 hydrocarbons Chemical class 0.000 claims description 38
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 37
- 229930195733 hydrocarbon Natural products 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 21
- 229910001868 water Inorganic materials 0.000 claims description 21
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 15
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 claims description 14
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims description 14
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 14
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 14
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 14
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 14
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 14
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims description 14
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 claims description 14
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 11
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- IHPKGUQCSIINRJ-CSKARUKUSA-N (E)-beta-ocimene Chemical compound CC(C)=CC\C=C(/C)C=C IHPKGUQCSIINRJ-CSKARUKUSA-N 0.000 claims description 7
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- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 7
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 7
- 238000000638 solvent extraction Methods 0.000 claims description 7
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 claims description 7
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- 238000012546 transfer Methods 0.000 claims description 6
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 4
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 claims description 2
- CXENHBSYCFFKJS-VDQVFBMKSA-N (E,E)-alpha-farnesene Chemical compound CC(C)=CCC\C(C)=C\C\C=C(/C)C=C CXENHBSYCFFKJS-VDQVFBMKSA-N 0.000 claims description 2
- ZJVWGOLNVKJRDF-UHFFFAOYSA-N 2-methylbut-3-en-2-yl acetate Chemical compound CC(=O)OC(C)(C)C=C ZJVWGOLNVKJRDF-UHFFFAOYSA-N 0.000 claims description 2
- 235000000983 citronellal Nutrition 0.000 claims description 2
- 229930003633 citronellal Natural products 0.000 claims description 2
- 229940044613 1-propanol Drugs 0.000 claims 1
- BVCLXNHIJBDDTH-UHFFFAOYSA-N but-1-en-2-yl acetate Chemical compound CCC(=C)OC(C)=O BVCLXNHIJBDDTH-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 21
- 239000000243 solution Substances 0.000 description 109
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- 210000004027 cell Anatomy 0.000 description 59
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
- 239000007789 gas Substances 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000000855 fermentation Methods 0.000 description 37
- 230000004151 fermentation Effects 0.000 description 37
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 32
- 108090000765 processed proteins & peptides Proteins 0.000 description 32
- 102000039446 nucleic acids Human genes 0.000 description 31
- 108020004707 nucleic acids Proteins 0.000 description 31
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 30
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- 102000004196 processed proteins & peptides Human genes 0.000 description 29
- 229910052799 carbon Inorganic materials 0.000 description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 description 26
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 25
- 239000000377 silicon dioxide Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 21
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 20
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- 238000009835 boiling Methods 0.000 description 18
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- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000001184 proton transfer reaction mass spectrometry Methods 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002916 wood waste Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/173—Alkadienes with five carbon atoms
- C07C11/18—Isoprene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28814209P | 2009-12-18 | 2009-12-18 | |
| PCT/US2010/060552 WO2011075534A2 (en) | 2009-12-18 | 2010-12-15 | Purification of isoprene from renewable resources |
Publications (2)
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| BR112012014736A2 BR112012014736A2 (pt) | 2016-04-19 |
| BR112012014736B1 true BR112012014736B1 (pt) | 2018-09-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| BR112012014736A BR112012014736B1 (pt) | 2009-12-18 | 2010-12-15 | método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição |
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| Country | Link |
|---|---|
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| EP (1) | EP2513021A2 (cg-RX-API-DMAC10.html) |
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| CN (1) | CN102884028B (cg-RX-API-DMAC10.html) |
| AR (1) | AR079560A1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU2010331946A1 (cg-RX-API-DMAC10.html) |
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| TW (1) | TWI481594B (cg-RX-API-DMAC10.html) |
| WO (1) | WO2011075534A2 (cg-RX-API-DMAC10.html) |
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| MX318543B (es) | 2008-07-02 | 2014-03-18 | Danisco Us Inc | Composiciones y metodos para producir isopreno libre de hidrocarburos de c5 bajo condicion de desacoplamiento y/o intervalos de operacion seguros. |
| US8324442B2 (en) | 2009-03-03 | 2012-12-04 | Amyris, Inc. | Microbial derived isoprene and methods for making the same |
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| TW201412988A (zh) * | 2009-06-17 | 2014-04-01 | Danisco Us Inc | 使用ｄｘｐ及ｍｖａ途徑之改良之異戊二烯製造 |
| WO2011075534A2 (en) * | 2009-12-18 | 2011-06-23 | Danisco Us Inc. | Purification of isoprene from renewable resources |
| WO2011075748A1 (en) * | 2009-12-22 | 2011-06-23 | Danisco Us Inc. | Membrane bioreactor for increased production of isoprene gas |
| CN103025688A (zh) | 2010-06-17 | 2013-04-03 | 丹尼斯科美国公司 | 包含异戊二烯衍生物的燃料组合物 |
| EP2601300A1 (en) | 2010-08-06 | 2013-06-12 | Danisco US Inc. | Production of isoprene under neutral ph conditions |
| SG190043A1 (en) | 2010-10-27 | 2013-06-28 | Danisco Us Inc | Isoprene synthase variants for improved production of isoprene |
| CN103403145A (zh) | 2010-12-22 | 2013-11-20 | 丹尼斯科美国公司 | 使用重组细胞进行戊糖的生物制备 |
| CN103476926A (zh) | 2010-12-22 | 2013-12-25 | 丹尼斯科美国公司 | 使用两种类型的ispg酶改善异戊二烯产量的组合物和方法 |
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| HK1198837A1 (en) | 2011-08-05 | 2015-06-12 | Danisco Us Inc. | Production of isoprenoids under neutral ph conditions |
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| DK2771460T3 (en) | 2011-10-27 | 2017-06-06 | Danisco Us Inc | ISOPRENE SYNTHASE VARIETIES WITH IMPROVED SOLUBILITY FOR THE PREPARATION OF ISOPRENE |
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| US9163263B2 (en) | 2012-05-02 | 2015-10-20 | The Goodyear Tire & Rubber Company | Identification of isoprene synthase variants with improved properties for the production of isoprene |
| JP6010342B2 (ja) * | 2012-05-21 | 2016-10-19 | 株式会社ブリヂストン | イソプレン−ブタジエン共重合体、イソプレン−ブタジエン共重合体の製造方法、ゴム組成物及びタイヤ |
| JP6010343B2 (ja) * | 2012-05-21 | 2016-10-19 | 株式会社ブリヂストン | イソプレン−ブタジエン共重合体、イソプレン−ブタジエン共重合体の製造方法、ゴム組成物及びタイヤ |
| JP6074160B2 (ja) * | 2012-05-22 | 2017-02-01 | 株式会社ブリヂストン | ゴム組成物およびタイヤの製造方法 |
| JP6074161B2 (ja) * | 2012-05-22 | 2017-02-01 | 株式会社ブリヂストン | ゴム組成物およびタイヤの製造方法 |
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| EP2935364A2 (en) | 2012-12-21 | 2015-10-28 | Danisco US Inc. | Production of isoprene, isoprenoid, and isoprenoid precursors using an alternative lower mevalonate pathway |
| BR112015018807B1 (pt) * | 2013-02-07 | 2021-07-27 | Braskem S.A. | Método para separação e purificação de uma diolefina conjugada produzida por fermentação sob condições anaeróbicas |
| US9850512B2 (en) | 2013-03-15 | 2017-12-26 | The Research Foundation For The State University Of New York | Hydrolysis of cellulosic fines in primary clarified sludge of paper mills and the addition of a surfactant to increase the yield |
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| ES2728307T3 (es) | 2013-06-21 | 2019-10-23 | Danisco Us Inc | Composiciones y métodos para la transformación clostridial |
| BR112016012491B1 (pt) * | 2013-12-02 | 2022-03-29 | Braskem S.A. | Método para separar e purificar um produto de fermentação de um gás residual fermentador |
| EP3107993B1 (en) | 2014-02-20 | 2020-08-26 | Danisco US Inc. | Recombinant microorganisms for the enhanced production of mevalonate, isoprene, isoprenoid precursors, isoprenoids, and acetyl-coa-derived products |
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| CN106866341B (zh) * | 2017-01-20 | 2019-08-06 | 中国科学院青岛生物能源与过程研究所 | 一种分离回收发酵尾气中低浓度异戊二烯的方法 |
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| CN110354644A (zh) * | 2018-04-10 | 2019-10-22 | 天津科技大学 | 一种高效的醋酸丁酯废气吸收与解吸装置 |
| CN111454114B (zh) * | 2020-05-11 | 2023-07-14 | 长沙贝塔医药科技有限公司 | 一种用13c2-香叶醇合成高纯度13c2-月桂烯的方法 |
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-
2010
- 2010-12-15 WO PCT/US2010/060552 patent/WO2011075534A2/en not_active Ceased
- 2010-12-15 CN CN201080064167.4A patent/CN102884028B/zh not_active Expired - Fee Related
- 2010-12-15 SG SG2012042511A patent/SG181605A1/en unknown
- 2010-12-15 BR BR112012014736A patent/BR112012014736B1/pt not_active IP Right Cessation
- 2010-12-15 EP EP10799184A patent/EP2513021A2/en not_active Withdrawn
- 2010-12-15 IN IN5187DEN2012 patent/IN2012DN05187A/en unknown
- 2010-12-15 JP JP2012544763A patent/JP5643838B2/ja not_active Expired - Fee Related
- 2010-12-15 AU AU2010331946A patent/AU2010331946A1/en not_active Abandoned
- 2010-12-15 US US12/969,440 patent/US8569562B2/en active Active
- 2010-12-15 CA CA2783976A patent/CA2783976A1/en not_active Abandoned
- 2010-12-17 TW TW099144617A patent/TWI481594B/zh active
- 2010-12-20 AR ARP100104783A patent/AR079560A1/es unknown
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2013
- 2013-09-24 US US14/035,746 patent/US20140187839A1/en not_active Abandoned
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2014
- 2014-09-10 JP JP2014184058A patent/JP6378013B2/ja not_active Expired - Fee Related
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2015
- 2015-04-09 US US14/682,930 patent/US9751820B2/en active Active
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2016
- 2016-11-18 JP JP2016225310A patent/JP2017081924A/ja active Pending
Also Published As
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| BR112012014736A2 (pt) | 2016-04-19 |
| AR079560A1 (es) | 2012-02-01 |
| WO2011075534A3 (en) | 2012-04-12 |
| EP2513021A2 (en) | 2012-10-24 |
| TWI481594B (zh) | 2015-04-21 |
| US20110178261A1 (en) | 2011-07-21 |
| US8569562B2 (en) | 2013-10-29 |
| CN102884028A (zh) | 2013-01-16 |
| AU2010331946A2 (en) | 2012-07-19 |
| JP2017081924A (ja) | 2017-05-18 |
| JP5643838B2 (ja) | 2014-12-17 |
| US20150274615A1 (en) | 2015-10-01 |
| WO2011075534A2 (en) | 2011-06-23 |
| JP2013514375A (ja) | 2013-04-25 |
| US20140187839A1 (en) | 2014-07-03 |
| CA2783976A1 (en) | 2011-06-23 |
| JP2015007119A (ja) | 2015-01-15 |
| IN2012DN05187A (cg-RX-API-DMAC10.html) | 2015-10-23 |
| CN102884028B (zh) | 2015-08-19 |
| JP6378013B2 (ja) | 2018-08-22 |
| AU2010331946A1 (en) | 2012-06-28 |
| TW201139367A (en) | 2011-11-16 |
| US9751820B2 (en) | 2017-09-05 |
| SG181605A1 (en) | 2012-07-30 |
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