ES2449915T3 - Métodos y dispositivos para la producción de disoluciones acuosas de cianopiridinas - Google Patents
Métodos y dispositivos para la producción de disoluciones acuosas de cianopiridinas Download PDFInfo
- Publication number
- ES2449915T3 ES2449915T3 ES10768872.3T ES10768872T ES2449915T3 ES 2449915 T3 ES2449915 T3 ES 2449915T3 ES 10768872 T ES10768872 T ES 10768872T ES 2449915 T3 ES2449915 T3 ES 2449915T3
- Authority
- ES
- Spain
- Prior art keywords
- cyanopyridine
- column
- gas phase
- section
- heat exchanger
- 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
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical class N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 93
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 title claims description 49
- 239000007789 gas Substances 0.000 claims abstract description 90
- 239000012071 phase Substances 0.000 claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910001868 water Inorganic materials 0.000 claims abstract description 31
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 20
- 239000007792 gaseous phase Substances 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims description 54
- 239000002250 absorbent Substances 0.000 claims description 52
- 230000002745 absorbent Effects 0.000 claims description 52
- 239000007788 liquid Substances 0.000 claims description 22
- 238000005406 washing Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 7
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical group CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 6
- 238000005915 ammonolysis reaction Methods 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkyl pyridine Chemical compound 0.000 claims description 4
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical group N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- 239000003990 capacitor Substances 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 20
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 229960003512 nicotinic acid Drugs 0.000 description 11
- 235000005152 nicotinamide Nutrition 0.000 description 10
- 239000011570 nicotinamide Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000001968 nicotinic acid Nutrition 0.000 description 9
- 239000011664 nicotinic acid Substances 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229960003966 nicotinamide Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 7
- 230000008033 biological extinction Effects 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 229930003537 Vitamin B3 Natural products 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 229940046001 vitamin b complex Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25237309P | 2009-10-16 | 2009-10-16 | |
| EP09013113A EP2319834A1 (en) | 2009-10-16 | 2009-10-16 | Methods and devices for the production of aqueous solutions of cyanopyridines |
| EP09013113 | 2009-10-16 | ||
| US252373P | 2009-10-16 | ||
| PCT/EP2010/006204 WO2011045015A1 (en) | 2009-10-16 | 2010-10-12 | Methods and devices for the production of aqueous solutions of cyanopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2449915T3 true ES2449915T3 (es) | 2014-03-21 |
Family
ID=41693013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10768872.3T Active ES2449915T3 (es) | 2009-10-16 | 2010-10-12 | Métodos y dispositivos para la producción de disoluciones acuosas de cianopiridinas |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8680287B2 (enExample) |
| EP (2) | EP2319834A1 (enExample) |
| JP (1) | JP5730882B2 (enExample) |
| KR (1) | KR101775887B1 (enExample) |
| CN (1) | CN102648181B (enExample) |
| AU (1) | AU2010306144B2 (enExample) |
| BR (1) | BR112012012143A2 (enExample) |
| CA (1) | CA2775025C (enExample) |
| DK (1) | DK2488499T3 (enExample) |
| EA (1) | EA020721B1 (enExample) |
| ES (1) | ES2449915T3 (enExample) |
| IN (1) | IN2012DN02614A (enExample) |
| MX (1) | MX2012004464A (enExample) |
| MY (1) | MY156176A (enExample) |
| PL (1) | PL2488499T3 (enExample) |
| WO (1) | WO2011045015A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2319833A1 (en) * | 2009-10-16 | 2011-05-11 | Lonza Ltd. | Methods and devices for the production of aqueous solutions of cyanopyridines |
| CN103360304A (zh) * | 2013-07-27 | 2013-10-23 | 新乡市博科精细化工有限公司 | 2-甲基吡啶的加工生产装置 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2861299A (en) | 1958-11-25 | Apparatus for and method of cleaning lint cotton | ||
| GB790937A (en) * | 1955-08-23 | 1958-02-19 | Distillers Co Yeast Ltd | Process for the recovery of cyanopyridines |
| US2929811A (en) * | 1958-11-28 | 1960-03-22 | Bernard T Hofreiter | Starch products of stable viscosity |
| US3929811A (en) * | 1973-11-15 | 1975-12-30 | Lummus Co | Production of pyridine nitriles and carboxylic acids |
| US4603207A (en) * | 1985-10-24 | 1986-07-29 | The Standard Oil Company | Conversion of a mixture of 3-methylpyridine and 3-methylpiperidine to 3-cyanopyridine |
| US4810794A (en) * | 1986-02-06 | 1989-03-07 | Koei Chemical Co., Ltd. | Process for producing pyridine bases |
| JPH0692368B2 (ja) * | 1986-02-06 | 1994-11-16 | 広栄化学工業株式会社 | ピリジン塩基の合成方法 |
| EE03555B1 (et) * | 1994-05-23 | 2001-12-17 | Lonza Ltd. | Katalüütiline koostis alküülpüridiinide oksüdeerivaks ammonolüüsiks |
| CN1086311C (zh) | 1994-05-23 | 2002-06-19 | 隆萨股份公司 | 烷基吡啶的氧化氨解 |
| HUT76437A (en) * | 1994-05-23 | 1997-08-28 | Inst Of Chemical Science Of Th | Process for oxidative ammonolysis of alkylpyridines |
| DE19504283A1 (de) | 1995-02-09 | 1996-08-14 | Degussa | Verfahren zur Herstellung von Cyanopyridinen und dafür geeignete Katalysatoren |
| ZA968485B (en) * | 1995-11-01 | 1997-05-20 | Lonza Ag | Process for preparing nicotinamide |
| JPH09136876A (ja) * | 1995-11-14 | 1997-05-27 | Nitto Chem Ind Co Ltd | ２−シアノ−３−メチルピリジンの回収法 |
| US5786443A (en) * | 1995-12-14 | 1998-07-28 | E. I. Du Pont De Nemours And Company | Process of making polyester prepolymer |
| US6118003A (en) * | 1998-01-29 | 2000-09-12 | Reilly Industries, Inc. | Processes for producing 3-cyanopyridine from 2-methyl-1,5-pentanediamine |
| CN100390147C (zh) * | 2001-09-07 | 2008-05-28 | 喜洋洋有机合成有限公司 | 杂芳腈的制备方法,其改良的催化剂及所述改良催化剂的制备方法 |
| DE10305650A1 (de) | 2003-02-12 | 2004-08-26 | Reilly Industries, Inc., Indianapolis | Verfahren zur Regenerierung von Mischoxidkatalysatoren |
| DE10335454A1 (de) | 2003-08-02 | 2005-02-24 | Reilly Industries, Inc., Indianapolis | Verfahren zur Herstellung von Cyanopyridinen und dafür geeignete Katalysatoren |
| CN100532361C (zh) | 2006-03-27 | 2009-08-26 | 中国石油化工股份有限公司上海石油化工研究院 | 3-氰基吡啶吸收方法 |
| WO2008021836A1 (en) * | 2006-08-08 | 2008-02-21 | Dow Agrosciences Llc | Process for quenching gaseous reaction product containing cyanopyridine |
| EP2319833A1 (en) * | 2009-10-16 | 2011-05-11 | Lonza Ltd. | Methods and devices for the production of aqueous solutions of cyanopyridines |
-
2009
- 2009-10-16 EP EP09013113A patent/EP2319834A1/en not_active Ceased
-
2010
- 2010-10-12 MY MYPI2012001386A patent/MY156176A/en unknown
- 2010-10-12 AU AU2010306144A patent/AU2010306144B2/en not_active Ceased
- 2010-10-12 KR KR1020127012206A patent/KR101775887B1/ko not_active Expired - Fee Related
- 2010-10-12 DK DK10768872.3T patent/DK2488499T3/da active
- 2010-10-12 EP EP10768872.3A patent/EP2488499B1/en not_active Not-in-force
- 2010-10-12 ES ES10768872.3T patent/ES2449915T3/es active Active
- 2010-10-12 JP JP2012533518A patent/JP5730882B2/ja not_active Expired - Fee Related
- 2010-10-12 PL PL10768872T patent/PL2488499T3/pl unknown
- 2010-10-12 EA EA201200596A patent/EA020721B1/ru not_active IP Right Cessation
- 2010-10-12 CN CN201080046250.9A patent/CN102648181B/zh not_active Expired - Fee Related
- 2010-10-12 BR BR112012012143A patent/BR112012012143A2/pt not_active Application Discontinuation
- 2010-10-12 CA CA2775025A patent/CA2775025C/en not_active Expired - Fee Related
- 2010-10-12 WO PCT/EP2010/006204 patent/WO2011045015A1/en not_active Ceased
- 2010-10-12 MX MX2012004464A patent/MX2012004464A/es active IP Right Grant
- 2010-10-12 IN IN2614DEN2012 patent/IN2012DN02614A/en unknown
- 2010-10-13 US US12/903,270 patent/US8680287B2/en not_active Expired - Fee Related
-
2014
- 2014-01-27 US US14/165,219 patent/US9155977B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2488499B1 (en) | 2013-12-18 |
| CA2775025A1 (en) | 2011-04-21 |
| JP2013507406A (ja) | 2013-03-04 |
| AU2010306144A1 (en) | 2012-05-10 |
| US8680287B2 (en) | 2014-03-25 |
| CN102648181B (zh) | 2015-11-25 |
| CA2775025C (en) | 2017-09-05 |
| MX2012004464A (es) | 2012-05-08 |
| KR101775887B1 (ko) | 2017-09-19 |
| JP5730882B2 (ja) | 2015-06-10 |
| EA201200596A1 (ru) | 2012-12-28 |
| MY156176A (en) | 2016-01-15 |
| US20140140901A1 (en) | 2014-05-22 |
| EA020721B1 (ru) | 2015-01-30 |
| US9155977B2 (en) | 2015-10-13 |
| KR20120087150A (ko) | 2012-08-06 |
| EP2488499A1 (en) | 2012-08-22 |
| WO2011045015A1 (en) | 2011-04-21 |
| EP2319834A1 (en) | 2011-05-11 |
| BR112012012143A2 (pt) | 2015-09-08 |
| US20110092709A1 (en) | 2011-04-21 |
| CN102648181A (zh) | 2012-08-22 |
| PL2488499T3 (pl) | 2014-05-30 |
| HK1169406A1 (zh) | 2013-01-25 |
| DK2488499T3 (da) | 2014-03-24 |
| AU2010306144B2 (en) | 2016-03-31 |
| IN2012DN02614A (enExample) | 2015-09-04 |
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