CA2843696C - Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up - Google Patents
Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up Download PDFInfo
- Publication number
- CA2843696C CA2843696C CA2843696A CA2843696A CA2843696C CA 2843696 C CA2843696 C CA 2843696C CA 2843696 A CA2843696 A CA 2843696A CA 2843696 A CA2843696 A CA 2843696A CA 2843696 C CA2843696 C CA 2843696C
- Authority
- CA
- Canada
- Prior art keywords
- solution
- succinic acid
- mgcl2
- magnesium
- magnesium succinate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 238000001556 precipitation Methods 0.000 title claims abstract description 73
- 238000000855 fermentation Methods 0.000 title claims description 58
- 230000004151 fermentation Effects 0.000 title claims description 58
- 238000011084 recovery Methods 0.000 title claims description 5
- 159000000003 magnesium salts Chemical class 0.000 title abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 2
- 238000010626 work up procedure Methods 0.000 title description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 241
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 146
- 239000001384 succinic acid Substances 0.000 claims abstract description 117
- OKUCEQDKBKYEJY-UHFFFAOYSA-N tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate Chemical compound CNC1CCN(C(=O)OC(C)(C)C)C1 OKUCEQDKBKYEJY-UHFFFAOYSA-N 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 74
- 229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 72
- 239000002244 precipitate Substances 0.000 claims abstract description 32
- 230000001376 precipitating effect Effects 0.000 claims abstract description 12
- 238000000926 separation method Methods 0.000 claims abstract description 10
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 147
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 83
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 32
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 28
- 239000000347 magnesium hydroxide Substances 0.000 claims description 28
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 28
- 235000012254 magnesium hydroxide Nutrition 0.000 claims description 28
- 239000000725 suspension Substances 0.000 claims description 24
- 239000000395 magnesium oxide Substances 0.000 claims description 23
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 23
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 15
- 239000011777 magnesium Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 11
- 229910052749 magnesium Inorganic materials 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 230000003472 neutralizing effect Effects 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 5
- 239000001095 magnesium carbonate Substances 0.000 claims description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 4
- 239000002028 Biomass Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims 6
- 235000014380 magnesium carbonate Nutrition 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 20
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 19
- 230000000694 effects Effects 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 8
- 239000002699 waste material Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000005185 salting out Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 238000010899 nucleation Methods 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- 150000003890 succinate salts Chemical class 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000006911 nucleation Effects 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 239000012296 anti-solvent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 235000011148 calcium chloride Nutrition 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003916 acid precipitation Methods 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- PBUBJNYXWIDFMU-UHFFFAOYSA-L calcium;butanedioate Chemical compound [Ca+2].[O-]C(=O)CCC([O-])=O PBUBJNYXWIDFMU-UHFFFAOYSA-L 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/03—Preparation from chlorides
- C01B7/035—Preparation of hydrogen chloride from chlorides
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F5/00—Compounds of magnesium
- C01F5/02—Magnesia
- C01F5/06—Magnesia by thermal decomposition of magnesium compounds
- C01F5/10—Magnesia by thermal decomposition of magnesium compounds by thermal decomposition of magnesium chloride with water vapour
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F5/00—Compounds of magnesium
- C01F5/26—Magnesium halides
- C01F5/30—Chlorides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11177633.2 | 2011-08-16 | ||
| EP11177633 | 2011-08-16 | ||
| US201161524353P | 2011-08-17 | 2011-08-17 | |
| US61/524,353 | 2011-08-17 | ||
| PCT/NL2012/050572 WO2013025105A1 (en) | 2011-08-16 | 2012-08-16 | Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2843696A1 CA2843696A1 (en) | 2013-02-21 |
| CA2843696C true CA2843696C (en) | 2019-09-24 |
Family
ID=50279087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2843696A Active CA2843696C (en) | 2011-08-16 | 2012-08-16 | Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9376364B2 (enExample) |
| EP (1) | EP2744745B1 (enExample) |
| JP (1) | JP6146922B2 (enExample) |
| KR (1) | KR101991705B1 (enExample) |
| CN (1) | CN103813977A (enExample) |
| AU (1) | AU2012295625B2 (enExample) |
| BR (1) | BR112014003379A2 (enExample) |
| CA (1) | CA2843696C (enExample) |
| EA (1) | EA027269B1 (enExample) |
| IN (1) | IN2014CN01924A (enExample) |
| PL (1) | PL2744745T3 (enExample) |
| UA (1) | UA112991C2 (enExample) |
| WO (1) | WO2013025105A1 (enExample) |
| ZA (1) | ZA201401748B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3401410B1 (en) | 2010-06-26 | 2020-12-30 | Virdia, Inc. | Methods for production of sugar mixtures |
| IL206678A0 (en) | 2010-06-28 | 2010-12-30 | Hcl Cleantech Ltd | A method for the production of fermentable sugars |
| EP3401322B1 (en) | 2011-04-07 | 2022-06-08 | Virdia, LLC | Lignocellulose conversion processes and products |
| KR101975177B1 (ko) | 2011-08-16 | 2019-05-07 | 푸락 바이오켐 비.브이. | 발효 브로스 후처리에 유용한, 염산을 사용하는 침전에 의한 카복실산 마그네슘염으로부터의 카복실산의 회수 |
| EA035054B1 (ru) * | 2011-08-16 | 2020-04-22 | Пурак Биокем Б.В. | Извлечение карбоновой кислоты из ее магниевых солей путем осаждения с применением хлористоводородной кислоты, пригодное для выделения продукта реакции из ферментативного бульона |
| BR112014027474B1 (pt) | 2012-05-03 | 2020-03-17 | Virdia, Inc. | Métodos de processamento de materiais lingnocelulósicos |
| EP2821368A1 (en) * | 2013-07-03 | 2015-01-07 | PURAC Biochem BV | Method for processing magnesium chloride solutions |
| WO2016112134A1 (en) | 2015-01-07 | 2016-07-14 | Virdia, Inc. | Methods for extracting and converting hemicellulose sugars |
| BR112017025322A8 (pt) * | 2015-05-27 | 2022-08-23 | Virdia Inc | Processos integrados para recuperação de hidrolisato celulósico após hidrólise de polpa de celulose |
| EP3118185A1 (en) * | 2015-07-14 | 2017-01-18 | PURAC Biochem BV | Method for manufacturing succinic acid |
| EP3124434A1 (en) | 2015-07-31 | 2017-02-01 | PURAC Biochem BV | Method for providing a succinic acid solution |
| JP6667646B2 (ja) * | 2016-01-19 | 2020-03-18 | ピュラック バイオケム ビー． ブイ． | 塩化マグネシウム溶液の改良処理方法及びカルボン酸の製造方法 |
| US10933592B2 (en) | 2016-06-29 | 2021-03-02 | Valinge Innovation Ab | Method and device for inserting a tongue |
| CN114906812B (zh) * | 2022-06-01 | 2023-06-23 | 湖南吴赣药业有限公司 | 一种有机混酸分离纯化方法 |
| WO2024097329A1 (en) | 2022-11-02 | 2024-05-10 | Amalgamated Research Llc | Smb separator for organic acid purification using a strong acid cation resin |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE548967A (enExample) | 1954-12-08 | 1956-07-14 | ||
| GB9102393D0 (en) | 1991-02-05 | 1991-03-20 | Ici Plc | Production of terephthalic acid |
| AUPP437698A0 (en) * | 1998-06-30 | 1998-07-23 | Baumgart, Karl | Methods for treatment of coronary, carotid and other vascular disease |
| IL126264A0 (en) | 1998-09-17 | 1999-05-09 | Tami Inst For Research & Dev L | Process for preparing lactic acid |
| US6670505B1 (en) * | 2000-03-07 | 2003-12-30 | Eastman Chemical Company | Process for the recovery of organic acids from aqueous solutions |
| US6660505B2 (en) | 2000-06-22 | 2003-12-09 | Cognis Corporation | Isolation of carboxylic acids from fermentation broth |
| CN100534972C (zh) * | 2003-09-30 | 2009-09-02 | 味之素株式会社 | 从发酵液中纯化琥珀酸的方法 |
| JP2009079057A (ja) | 2005-04-22 | 2009-04-16 | Mitsubishi Chemicals Corp | ポリエステル及びその製造方法 |
| US20080223519A1 (en) | 2006-12-06 | 2008-09-18 | Locko George A | Polyamide polyols and polyurethanes, methods for making and using, and products made therefrom |
| FR2925068B1 (fr) * | 2007-12-13 | 2010-01-08 | Roquette Freres | Procedes de production d'acide succinique |
| CN101550079B (zh) * | 2009-05-12 | 2010-10-27 | 安徽丰原发酵技术工程研究有限公司 | 一种连续制备丁二酸的方法 |
| KR101051582B1 (ko) * | 2009-05-13 | 2011-07-22 | 삼성석유화학(주) | 발효액으로부터 숙신산을 분리 및 정제하는 방법 |
| US8431372B2 (en) * | 2009-06-19 | 2013-04-30 | Mbi International | Fermentation method using a magnesium compound containing oxygen |
| CN101748161B (zh) * | 2010-01-19 | 2012-06-06 | 南京工业大学 | 一种厌氧发酵纯化丁二酸的工艺 |
| KR101975177B1 (ko) | 2011-08-16 | 2019-05-07 | 푸락 바이오켐 비.브이. | 발효 브로스 후처리에 유용한, 염산을 사용하는 침전에 의한 카복실산 마그네슘염으로부터의 카복실산의 회수 |
-
2012
- 2012-08-16 CA CA2843696A patent/CA2843696C/en active Active
- 2012-08-16 JP JP2014525958A patent/JP6146922B2/ja not_active Expired - Fee Related
- 2012-08-16 WO PCT/NL2012/050572 patent/WO2013025105A1/en not_active Ceased
- 2012-08-16 KR KR1020147006790A patent/KR101991705B1/ko not_active Expired - Fee Related
- 2012-08-16 EP EP12750876.0A patent/EP2744745B1/en active Active
- 2012-08-16 US US14/238,666 patent/US9376364B2/en not_active Expired - Fee Related
- 2012-08-16 PL PL12750876T patent/PL2744745T3/pl unknown
- 2012-08-16 UA UAA201402003A patent/UA112991C2/uk unknown
- 2012-08-16 EA EA201490408A patent/EA027269B1/ru not_active IP Right Cessation
- 2012-08-16 AU AU2012295625A patent/AU2012295625B2/en not_active Ceased
- 2012-08-16 IN IN1924CHN2014 patent/IN2014CN01924A/en unknown
- 2012-08-16 CN CN201280045958.1A patent/CN103813977A/zh active Pending
- 2012-08-16 BR BR112014003379A patent/BR112014003379A2/pt not_active IP Right Cessation
-
2014
- 2014-03-10 ZA ZA2014/01748A patent/ZA201401748B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013025105A8 (en) | 2014-04-10 |
| EA027269B1 (ru) | 2017-07-31 |
| EA201490408A1 (ru) | 2014-07-30 |
| UA112991C2 (uk) | 2016-11-25 |
| US20140200365A1 (en) | 2014-07-17 |
| JP2014524254A (ja) | 2014-09-22 |
| EP2744745B1 (en) | 2019-10-30 |
| CA2843696A1 (en) | 2013-02-21 |
| EP2744745A1 (en) | 2014-06-25 |
| JP6146922B2 (ja) | 2017-06-14 |
| CN103813977A (zh) | 2014-05-21 |
| KR20140064870A (ko) | 2014-05-28 |
| AU2012295625B2 (en) | 2016-05-12 |
| BR112014003379A2 (pt) | 2017-03-01 |
| IN2014CN01924A (enExample) | 2015-05-29 |
| US9376364B2 (en) | 2016-06-28 |
| PL2744745T3 (pl) | 2020-05-18 |
| KR101991705B1 (ko) | 2019-06-21 |
| ZA201401748B (en) | 2015-01-28 |
| WO2013025105A1 (en) | 2013-02-21 |
| AU2012295625A1 (en) | 2014-03-20 |
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