JP2013523648A - 高い選択率のクメン製造 - Google Patents
高い選択率のクメン製造 Download PDFInfo
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- JP2013523648A JP2013523648A JP2013501423A JP2013501423A JP2013523648A JP 2013523648 A JP2013523648 A JP 2013523648A JP 2013501423 A JP2013501423 A JP 2013501423A JP 2013501423 A JP2013501423 A JP 2013501423A JP 2013523648 A JP2013523648 A JP 2013523648A
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- alkylation
- reaction zone
- cumene
- benzene
- propylene
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- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 title claims abstract description 220
- 238000004519 manufacturing process Methods 0.000 title description 24
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 284
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 246
- 230000029936 alkylation Effects 0.000 claims abstract description 185
- 239000003054 catalyst Substances 0.000 claims abstract description 121
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 63
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000006227 byproduct Substances 0.000 claims abstract description 43
- 230000008569 process Effects 0.000 claims abstract description 36
- 238000010555 transalkylation reaction Methods 0.000 claims description 68
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 66
- 239000010457 zeolite Substances 0.000 claims description 53
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 49
- 229910021536 Zeolite Inorganic materials 0.000 claims description 49
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 31
- 239000000047 product Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 6
- 238000007599 discharging Methods 0.000 claims description 2
- 238000010791 quenching Methods 0.000 abstract description 8
- 238000009835 boiling Methods 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 24
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 14
- 238000004821 distillation Methods 0.000 description 14
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000011027 product recovery Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 230000006872 improvement Effects 0.000 description 7
- 238000011144 upstream manufacturing Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000012084 conversion product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000004951 benzene Polymers 0.000 description 3
- 150000001555 benzenes Polymers 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- -1 fluorinated benzene compound Chemical class 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/085—Isopropylbenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
【選択図】図1
Description
[02]本発明は、プロピレンによるベンゼンのアルキル化からのクメンの製造方法に関し、特に、アルキル化反応区域へ戻す流出流再循環比をより低くし、及び/又はアルキル化反応区域へ供給するベンゼンのモル過剰量をより低くすることによってクメン選択率を増加させる方法に関する。
Me2/nO:Al2O3:xSiO2:yH2O
によって表すことができる。
[49]アルキル化反応区域、トランスアルキル化反応区域、及び生成物回収セクションを用いるパイロットスケールプロセスを用いて、プロピレンによるベンゼンのアルキル化から得られるクメンへの選択率に対する複数のプロセスパラメーターの影響を評価した。アルキル化反応区域は、アルキル化触媒を含む直列の3つの反応器を含んでいた。(i)アルキル化反応器への混合アルキル化供給原料中のベンゼン:プロピレンのモル比(B/P比)、及び(ii)アルキル化流出流再循環:アルキル化反応器へのアルキル化供給原料の重量比(再循環比)の下表1に示す以下の組合せを、異なる運転段階において研究した。
Claims (10)
- (a)ベンゼン及びプロピレンを含むアルキル化供給原料を、24〜35の骨格Si/Al2モル比を有するUZM−8ゼオライトを含むアルキル化触媒の少なくとも1つの床を含むアルキル化反応区域(100)に流入させ;そして
(b)アルキル化反応区域(100)からクメンを含むアルキル化流出流(10)を排出する;
ことを含み;
アルキル化供給原料中のプロピレンを、アルキル化反応区域(100)内において少なくとも85%の選択率でクメンに転化させる、プロピレンによるベンゼンのアルキル化からクメンを製造する方法。 - (d)アルキル化流出流(10)の再循環部分(10a)をアルキル化反応区域(100)に再循環する;
ことを更に含み、再循環部分(10a)の流速とアルキル化供給原料の流速との比が重量基準で3:1未満である、請求項1に記載の方法。 - アルキル化流出流(10)をアルキル化反応区域(100)に再循環しない、請求項1又は2に記載の方法。
- アルキル化反応区域(100)が直列の複数のアルキル化触媒床を含み、それぞれのアルキル化触媒床を横切る温度差が15℃(27°F)〜60℃(108°F)である、請求項3に記載の方法。
- UZM−8ゼオライトが27〜33の骨格Si/Al2モル比を有する、請求項1〜4のいずれかに記載の方法。
- (a)ベンゼン及びプロピレンを含むアルキル化供給原料を、直列の複数のアルキル化触媒床を含むアルキル化反応区域(100)の入口に、最大で2.5のベンゼン:プロピレンのモル比で流入させ;
(b)アルキル化反応区域(100)内の隣接する床の少なくとも1つの対の間から熱を除去し;そして
(c)アルキル化反応区域(100)からクメンを含むアルキル化流出流(10)を排出し、アルキル化流出流(10)の再循環部分(10a)をアルキル化反応区域(100)に再循環する;
ことを含み;
再循環部分(10a)の流速とアルキル化供給原料の流速との比が重量基準で3:1未満であり、アルキル化供給原料中のプロピレンを、アルキル化反応区域(100)内において少なくとも85%の選択率でクメンに転化させる、プロピレンによるベンゼンのアルキル化からクメンを製造する方法。 - アルキル化反応区域(100)が直列の複数のアルキル化触媒床を含み、アルキル化流出流(10)の再循環部分(10a)を隣接する床の少なくとも1つの対の間を含む位置に再循環し、それぞれの複数のアルキル化触媒床を横切る温度差が15℃(27°F)〜45℃(81°F)である、請求項6に記載の方法。
- (d)アルキル化流出流(10)の少なくとも非再循環部分(10b)から、クメン生成物(24)、重質副生成物(20)、ベンゼンフラクション(6)、及びジイソプロピルベンゼンフラクション(16)を回収し;
(e)トランスアルキル化区域(200)において、ベンゼンフラクション(6)の少なくとも一部及びジイソプロピルベンゼンフラクション(16)の少なくとも一部を、β−ゼオライトを含むゼオライトトランスアルキル化触媒と接触させて、ジイソプロピルベンゼンの少なくとも80%を転化させる;
ことを更に含む、請求項6又は7に記載の方法。 - 取り出される正味のトリイソプロピルベンゼン及びより高分子量の化合物に対する加えられる正味のベンゼン及びプロピレンの収率損失が0.5重量%未満である、請求項6〜8のいずれかの記載の方法。
- ベンゼン及びプロピレンを含むアルキル化供給原料を、UZM−8ゼオライトアルキル化触媒を含むアルキル化反応区域(100)に流入させて、アルキル化反応区域(100)内においてプロピレンを少なくとも85%の選択率でクメンに転化させることを含む、プロピレンによるベンゼンのアルキル化からクメンを製造する方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/751,132 | 2010-03-31 | ||
US12/751,132 US8242320B2 (en) | 2010-03-31 | 2010-03-31 | Cumene production with high selectivity |
PCT/US2011/029552 WO2011123302A2 (en) | 2010-03-31 | 2011-03-23 | Cumene production with high selectivity |
Publications (2)
Publication Number | Publication Date |
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JP2013523648A true JP2013523648A (ja) | 2013-06-17 |
JP5688132B2 JP5688132B2 (ja) | 2015-03-25 |
Family
ID=44710409
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2013501423A Active JP5688132B2 (ja) | 2010-03-31 | 2011-03-23 | 高い選択率のクメン製造 |
Country Status (14)
Country | Link |
---|---|
US (1) | US8242320B2 (ja) |
EP (1) | EP2552865B1 (ja) |
JP (1) | JP5688132B2 (ja) |
KR (1) | KR101511830B1 (ja) |
CN (1) | CN102811981B (ja) |
BR (1) | BR112012024024B1 (ja) |
ES (1) | ES2728477T3 (ja) |
MY (1) | MY152384A (ja) |
PL (1) | PL2552865T3 (ja) |
RU (1) | RU2517145C1 (ja) |
SA (1) | SA111320337B1 (ja) |
SG (1) | SG184282A1 (ja) |
TW (1) | TWI530476B (ja) |
WO (1) | WO2011123302A2 (ja) |
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US8609916B2 (en) | 2012-03-12 | 2013-12-17 | Uop Llc | Processes for preparing alkylated aromatic compounds |
US8609915B2 (en) | 2012-03-12 | 2013-12-17 | Uop Llc | Processes for preparing alkylated aromatic compounds |
US8853481B2 (en) | 2012-10-26 | 2014-10-07 | Uop Llc | Highly selective alkylation process with low zeolite catalyst composition |
US9593056B2 (en) | 2012-12-11 | 2017-03-14 | Exxonmobil Chemical Patents Inc. | Process for producing cumene with alkylation effluent recycle |
TWI510452B (zh) * | 2012-12-11 | 2015-12-01 | Exxonmobil Chem Patents Inc | 以烷化流出物循環製造異丙苯之方法 |
BR102014026858B1 (pt) * | 2013-10-28 | 2020-12-22 | China Petroleum & Chemical Corporation | método para produzir isopropilbenzeno a partir de benzeno e propileno |
KR101727362B1 (ko) | 2014-05-22 | 2017-04-14 | 주식회사 엘지화학 | 큐멘 정제장치 및 정제방법 |
KR101790391B1 (ko) | 2014-05-22 | 2017-10-26 | 주식회사 엘지화학 | 큐멘 정제장치 및 정제방법 |
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WO2017001284A1 (en) | 2015-06-29 | 2017-01-05 | Sabic Global Technologies B.V. | Process for producing cumene and/or ethylbenzene from a mixed hydrocarbon feedstream |
EP3512822A4 (en) | 2016-09-16 | 2020-08-26 | Lummus Technology LLC | INTEGRATED PROPAND DEHYDRATION PROCESS |
US11578278B2 (en) | 2020-08-01 | 2023-02-14 | Honeywell International Inc. | Renewable transportation fuel process with thermal oxidation system |
US11578020B2 (en) | 2020-08-04 | 2023-02-14 | Honeywell International Inc. | Naphtha complex with thermal oxidation system |
US11780795B2 (en) | 2020-08-04 | 2023-10-10 | Honeywell International Inc. | Cumene-phenol complex with thermal oxidation system |
US11492306B2 (en) | 2020-09-30 | 2022-11-08 | Honeywell International Inc. | Alkylation process with thermal oxidation system |
RU2770585C1 (ru) * | 2021-06-08 | 2022-04-18 | Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") | Способ получения изопропилбензола алкилированием бензола пропиленом |
US20230183153A1 (en) * | 2021-12-10 | 2023-06-15 | Kellogg Brown & Root Llc | Thermally coupled distillation scheme for purification of cumene |
KR102507523B1 (ko) * | 2022-04-28 | 2023-03-08 | 이주선 | 알킬화공정시스템 및 알킬화방법 |
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BR112012024024A2 (pt) | 2016-08-30 |
US8242320B2 (en) | 2012-08-14 |
TW201141814A (en) | 2011-12-01 |
ES2728477T3 (es) | 2019-10-24 |
JP5688132B2 (ja) | 2015-03-25 |
KR20130008595A (ko) | 2013-01-22 |
CN102811981B (zh) | 2015-06-10 |
RU2517145C1 (ru) | 2014-05-27 |
EP2552865A4 (en) | 2014-10-29 |
TWI530476B (zh) | 2016-04-21 |
SA111320337B1 (ar) | 2014-09-10 |
RU2012145104A (ru) | 2014-05-20 |
BR112012024024B1 (pt) | 2018-08-07 |
EP2552865B1 (en) | 2019-05-08 |
WO2011123302A3 (en) | 2012-01-12 |
MY152384A (en) | 2014-09-15 |
WO2011123302A2 (en) | 2011-10-06 |
SG184282A1 (en) | 2012-11-29 |
KR101511830B1 (ko) | 2015-04-13 |
CN102811981A (zh) | 2012-12-05 |
PL2552865T3 (pl) | 2019-10-31 |
EP2552865A2 (en) | 2013-02-06 |
US20110245558A1 (en) | 2011-10-06 |
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