RU2470706C2 - Твердый катализатор, используемый для превращения алкиленоксида в алкиленгликоль - Google Patents
Твердый катализатор, используемый для превращения алкиленоксида в алкиленгликоль Download PDFInfo
- Publication number
- RU2470706C2 RU2470706C2 RU2010119451/04A RU2010119451A RU2470706C2 RU 2470706 C2 RU2470706 C2 RU 2470706C2 RU 2010119451/04 A RU2010119451/04 A RU 2010119451/04A RU 2010119451 A RU2010119451 A RU 2010119451A RU 2470706 C2 RU2470706 C2 RU 2470706C2
- Authority
- RU
- Russia
- Prior art keywords
- exchange resin
- ion exchange
- glycol
- alkylene
- catalyst
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 37
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 35
- -1 alkylene glycol Chemical compound 0.000 title claims abstract description 28
- 239000011949 solid catalyst Substances 0.000 title description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 57
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 57
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 56
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000004793 Polystyrene Substances 0.000 claims abstract description 12
- 229920002223 polystyrene Polymers 0.000 claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005496 phosphonium group Chemical group 0.000 claims description 4
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- 230000003197 catalytic effect Effects 0.000 abstract description 20
- 238000006703 hydration reaction Methods 0.000 abstract description 12
- 230000036571 hydration Effects 0.000 abstract description 9
- 239000007787 solid Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000003957 anion exchange resin Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920005990 polystyrene resin Polymers 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical group C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/872,318 | 2007-10-15 | ||
| US11/872,318 US8053609B2 (en) | 2007-10-15 | 2007-10-15 | Solid catalyst useful for converting an alkylene oxide to an alkylene glycol |
| PCT/US2008/078654 WO2009051972A1 (en) | 2007-10-15 | 2008-10-03 | Solid catalyst useful for converting an alkylene oxide to an alkylene glycol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010119451A RU2010119451A (ru) | 2011-11-27 |
| RU2470706C2 true RU2470706C2 (ru) | 2012-12-27 |
Family
ID=40534877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010119451/04A RU2470706C2 (ru) | 2007-10-15 | 2008-10-03 | Твердый катализатор, используемый для превращения алкиленоксида в алкиленгликоль |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8053609B2 (enExample) |
| EP (1) | EP2212023B1 (enExample) |
| JP (1) | JP2011501692A (enExample) |
| KR (1) | KR101502921B1 (enExample) |
| CN (1) | CN101821002B (enExample) |
| BR (1) | BRPI0818057B1 (enExample) |
| CA (1) | CA2702498A1 (enExample) |
| MX (1) | MX2010004077A (enExample) |
| RU (1) | RU2470706C2 (enExample) |
| TW (1) | TWI527625B (enExample) |
| WO (1) | WO2009051972A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106478375A (zh) * | 2015-08-25 | 2017-03-08 | 中国石油化工股份有限公司 | 一种以阴离子交换树脂为催化剂合成邻二醇类化合物的方法 |
| CN106478374A (zh) * | 2015-08-25 | 2017-03-08 | 中国石油化工股份有限公司 | 一种通过开环反应制备邻二醇类化合物的方法 |
| CN106478365A (zh) * | 2015-08-25 | 2017-03-08 | 中国石油化工股份有限公司 | 一种邻二醇类化合物的合成方法 |
| CN112239393B (zh) * | 2019-07-17 | 2023-06-06 | 中国石油化工股份有限公司 | 纳米复合离子交换树脂催化剂及其应用 |
| CN116020557A (zh) * | 2021-10-25 | 2023-04-28 | 中国石油化工股份有限公司 | 离子交换树脂催化剂及其制备方法和应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0741683A1 (en) * | 1994-01-31 | 1996-11-13 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of alkylene glycols |
| EP0929503A1 (en) * | 1996-10-04 | 1999-07-21 | The Dow Chemical Company | A method for producing glycols |
| US6156942A (en) * | 1998-12-14 | 2000-12-05 | Shell Oil Company | Catalyst stabilizing additive in the hydrolysis of alkylene oxides |
| RU2211211C2 (ru) * | 1997-12-18 | 2003-08-27 | Дау Глобал Текнолоджиз Инк. | Способ получения алкиленгликолей |
| US6730816B2 (en) * | 2000-12-29 | 2004-05-04 | Rohm And Haas Company | High productivity bisphenol-A catalyst |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6056141B2 (ja) | 1981-02-24 | 1985-12-09 | 株式会社日本触媒 | アルキレングリコールの製造方法 |
| US4560813A (en) | 1984-03-28 | 1985-12-24 | Union Carbide Corporation | Processes for the production of alkylene glycol in the presence of organometalate |
| US4701571A (en) * | 1986-06-30 | 1987-10-20 | Union Carbide Corporation | Process for the production of alkylene glycols with metalate-containing solids |
| RU2002726C1 (ru) | 1992-05-19 | 1993-11-15 | Государственное научно-производственное предпри тие "Совинтех" | Способ получени алкиленгликолей |
| RU2001901C1 (ru) | 1992-05-19 | 1993-10-30 | Государственное научно-производственное предпри тие "Совинтех" | Способ получени алкиленгликолей |
| JPH07204523A (ja) * | 1994-01-19 | 1995-08-08 | Mitsubishi Chem Corp | 陰イオン交換樹脂およびその製造方法 |
| JPH07289912A (ja) * | 1994-03-01 | 1995-11-07 | Mitsubishi Chem Corp | 固体塩基性触媒 |
| WO1997033850A1 (fr) | 1996-03-11 | 1997-09-18 | Valery Fedorovich Shvets | Procede de production d'alcyleneglycols |
| JP3815045B2 (ja) * | 1997-04-30 | 2006-08-30 | 三菱化学株式会社 | アルキレングリコール類の製造方法 |
| MY121124A (en) * | 1998-12-14 | 2005-12-30 | Shell Int Research | Catalyst stabilising additive in the hydrolysis of alkylene oxides |
| US6153801A (en) * | 1998-12-14 | 2000-11-28 | Shell Oil Company | Carboxylates in catalytic hydrolysis of alkylene oxides |
| MY120595A (en) * | 1998-12-14 | 2005-11-30 | Shell Int Research | Quaternary phosphonium salt catalysts in catalytic hydrolysis of alkylene oxides |
| PE20001571A1 (es) * | 1998-12-14 | 2001-01-26 | Shell Int Research | Carboxilatos en la hidrolisis catalitica de oxidos de alquileno |
| US6211419B1 (en) * | 2000-04-24 | 2001-04-03 | The Dow Chemical Company | Process for the preparation of alkylene glycols |
| JP2002030112A (ja) * | 2000-07-18 | 2002-01-31 | Mitsubishi Chemicals Corp | アニオン交換樹脂、その製法及びこれを用いるクランピング防止方法 |
| JP2005060289A (ja) * | 2003-08-11 | 2005-03-10 | Mitsui Chemicals Inc | フェノール類の製造方法 |
-
2007
- 2007-10-15 US US11/872,318 patent/US8053609B2/en active Active
-
2008
- 2008-10-03 EP EP08838859.0A patent/EP2212023B1/en active Active
- 2008-10-03 JP JP2010528950A patent/JP2011501692A/ja active Pending
- 2008-10-03 CN CN200880111607.XA patent/CN101821002B/zh active Active
- 2008-10-03 CA CA2702498A patent/CA2702498A1/en not_active Abandoned
- 2008-10-03 RU RU2010119451/04A patent/RU2470706C2/ru active
- 2008-10-03 BR BRPI0818057-1A patent/BRPI0818057B1/pt active IP Right Grant
- 2008-10-03 KR KR1020107010705A patent/KR101502921B1/ko active Active
- 2008-10-03 MX MX2010004077A patent/MX2010004077A/es active IP Right Grant
- 2008-10-03 WO PCT/US2008/078654 patent/WO2009051972A1/en not_active Ceased
- 2008-10-09 TW TW097139098A patent/TWI527625B/zh active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0741683A1 (en) * | 1994-01-31 | 1996-11-13 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of alkylene glycols |
| EP0929503A1 (en) * | 1996-10-04 | 1999-07-21 | The Dow Chemical Company | A method for producing glycols |
| RU2211211C2 (ru) * | 1997-12-18 | 2003-08-27 | Дау Глобал Текнолоджиз Инк. | Способ получения алкиленгликолей |
| US6156942A (en) * | 1998-12-14 | 2000-12-05 | Shell Oil Company | Catalyst stabilizing additive in the hydrolysis of alkylene oxides |
| US6730816B2 (en) * | 2000-12-29 | 2004-05-04 | Rohm And Haas Company | High productivity bisphenol-A catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0818057B1 (pt) | 2022-05-17 |
| KR20100090260A (ko) | 2010-08-13 |
| BRPI0818057A2 (pt) | 2015-03-31 |
| EP2212023B1 (en) | 2016-05-11 |
| CN101821002B (zh) | 2014-11-05 |
| TWI527625B (zh) | 2016-04-01 |
| US20090099393A1 (en) | 2009-04-16 |
| RU2010119451A (ru) | 2011-11-27 |
| CN101821002A (zh) | 2010-09-01 |
| KR101502921B1 (ko) | 2015-03-16 |
| MX2010004077A (es) | 2010-05-24 |
| US8053609B2 (en) | 2011-11-08 |
| WO2009051972A1 (en) | 2009-04-23 |
| CA2702498A1 (en) | 2009-04-23 |
| EP2212023A4 (en) | 2010-12-01 |
| TW200934586A (en) | 2009-08-16 |
| EP2212023A1 (en) | 2010-08-04 |
| JP2011501692A (ja) | 2011-01-13 |
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