JP2012516846A - 脱イソブテン塔 - Google Patents
脱イソブテン塔 Download PDFInfo
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- JP2012516846A JP2012516846A JP2011548005A JP2011548005A JP2012516846A JP 2012516846 A JP2012516846 A JP 2012516846A JP 2011548005 A JP2011548005 A JP 2011548005A JP 2011548005 A JP2011548005 A JP 2011548005A JP 2012516846 A JP2012516846 A JP 2012516846A
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 164
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 123
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 106
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000004508 fractional distillation Methods 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004821 distillation Methods 0.000 claims description 16
- 230000003197 catalytic effect Effects 0.000 claims description 15
- -1 C 4 hydrocarbon Chemical class 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 9
- 239000000498 cooling water Substances 0.000 claims description 7
- 239000000112 cooling gas Substances 0.000 claims 2
- 239000003507 refrigerant Substances 0.000 claims 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 17
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 238000005649 metathesis reaction Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 238000005336 cracking Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical class CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 238000004231 fluid catalytic cracking Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 235000013844 butane Nutrition 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 235000013847 iso-butane Nutrition 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012809 cooling fluid Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Images
Classifications
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- 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
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
- C07C11/09—Isobutene
-
- 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
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- 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
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
-
- 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
- Y02P20/10—Process efficiency
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/06—Reactor-distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
【選択図】図1
Description
Claims (20)
- イソブテンをノルマルブテンから分別蒸留する方法であって、
イソブテン、1−ブテンおよび2−ブテンを含む供給流と、水素とを、接触蒸留反応システムを有する第一カラムに導入する工程と、
接触蒸留反応システムは、水素異性化触媒を有する少なくとも一つの反応ゾーンを含んでおり、
第一カラムは、
第一圧力で、同時に、
(i)1−ブテンの少なくとも一部を2−ブテンへと変換させ、
(ii)分別蒸留によってイソブテンを2−ブテンから分離する機能を有しており、
前記第一カラムから、イソブテンを含む第一塔頂留分を回収する工程と、
前記第一カラムから、イソブテン、2−ブテンおよび未反応の1−ブテンを含む第一底部留分を回収する工程と、
前記第一底部留分を、前記第一圧力よりも低圧の第二圧力で動作する分別蒸留カラムを有する第二カラムの上部に導入する工程と、
前記第一底部留分を、イソブテンと1−ブテンを含む第二塔頂留分と、2−ブテンを含む第二底部留分とに分離する工程と、
前記第二塔頂留分を圧縮し、その圧縮された第二塔頂留分を、第一カラムの下部に導入する工程と、を備える方法。 - 前記第二底部留分の少なくとも一部を前記第一底部留分と前記第一塔頂留分の少なくとも一方との間接熱交換により加熱することによって、前記第二カラムのための再沸騰蒸気を発生させる工程を更に含む請求項1に記載の方法。
- 前記第一塔頂留分との前記間接熱交換が、前記第一塔頂留分の少なくとも一部を凝縮させる請求項2に記載の方法。
- 前記凝縮された第一塔頂留分の少なくとも一部を、還流として第一カラムに戻す工程を更に含む請求項3に記載の方法。
- 冷却水、冷却ガス、冷媒の少なくとも一つとの間接熱交換により、前記第一塔頂留分の少なくとも一部を凝縮させる工程を更に含む請求項3に記載の方法。
- 前記第一カラムが、約5バールを超える圧力で操作される請求項1に記載の方法。
- 前記第一カラムが、約5.5バール〜約10バールの圧力で操作される請求項6に記載の方法。
- 前記第二カラムが、約5バール未満の圧力で操作される請求項6に記載の方法。
- 前記第二カラムが、約2バール〜約4.5バールの圧力で操作される請求項8に記載の方法。
- 前記第二底部留分が、イソブテン、1−ブテンおよび2−ブテンの総重量を基準として、イソブテンを3重量%未満含む請求項1に記載の方法。
- 混合C4炭化水素流を分別蒸留する方法であって、
n−ブテン類、イソブテンおよびパラフィン類を含む混合C4流と、水素とを、接触蒸留反応システムを有する第一カラムに導入する工程と、
接触蒸留反応システムは、水素異性化触媒を有する少なくとも一つの反応ゾーンを含んでおり、
第一カラムは、
第一圧力で、同時に
(i)1−ブテンの少なくとも一部を2−ブテンへと変換させ、
(ii)分別蒸留によってイソブテンを2−ブテンから分離する機能を有しており、
前記第一カラムから、イソブテンを含む第一塔頂留分を回収する工程と、
前記第一カラムから、イソブテン、2−ブテンおよび未反応の1−ブテンを含む第一底部留分を回収する工程と、
前記第一底部留分を、前記第一圧力よりも低圧の第二圧力で動作する分別蒸留カラムを有する第二カラムの上部に導入する工程と、
前記第一底部留分を、イソブテンと1−ブテンを含む第二塔頂留分と、2−ブテンを含む第二底部留分とに分離する工程と、
前記第二塔頂留分を圧縮し、その圧縮された第二塔頂留分を、第一カラムの下部に導入する工程と、を備える方法。 - 前記第二底部留分の少なくとも一部を前記第一底部留分と前記第一塔頂留分の少なくとも一方との間接熱交換により加熱することによって、前記第二カラムのための再沸騰蒸気を発生させる工程を更に含む請求項11に記載の方法。
- 前記第一塔頂留分との前記間接熱交換が、前記第一塔頂留分の少なくとも一部を凝縮させる請求項12に記載の方法。
- 前記凝縮された第一塔頂留分の少なくとも一部を、還流として前記第一カラムに戻す工程を更に含む請求項13に記載の方法。
- 冷却水、冷却ガス、冷媒の少なくとも一つとの間接熱交換により、前記第一塔頂留分の少なくとも一部を凝縮させる工程を更に含む請求項13に記載の方法。
- 前記第一カラムが、約5バールを超える圧力で操作される請求項11に記載の方法。
- 前記第一カラムが、約5.5バール〜約10バールの圧力で操作される請求項16に記載の方法。
- 前記第二カラムが、約5バール未満の圧力で操作される請求項16に記載の方法。
- 前記第二カラムが、約2バール〜約4.5バールの圧力で操作される請求項18に記載の方法。
- 前記第二底部留分が、イソブテン、1−ブテンおよび2−ブテンの総重量を基準として、イソブテンを3重量%未満含む請求項11に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/364,961 US7982086B2 (en) | 2009-02-03 | 2009-02-03 | Deisobutenizer |
US12/364,961 | 2009-02-03 | ||
PCT/US2010/020585 WO2010090790A1 (en) | 2009-02-03 | 2010-01-11 | Deisobutenizer |
Publications (2)
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JP2012516846A true JP2012516846A (ja) | 2012-07-26 |
JP5323948B2 JP5323948B2 (ja) | 2013-10-23 |
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JP2011548005A Active JP5323948B2 (ja) | 2009-02-03 | 2010-01-11 | 脱イソブテン塔 |
Country Status (10)
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US (1) | US7982086B2 (ja) |
JP (1) | JP5323948B2 (ja) |
KR (1) | KR101351164B1 (ja) |
CN (1) | CN101792363B (ja) |
BR (1) | BRPI1008827B1 (ja) |
EA (1) | EA020352B1 (ja) |
MY (1) | MY152010A (ja) |
SG (1) | SG173508A1 (ja) |
TW (1) | TWI503156B (ja) |
WO (1) | WO2010090790A1 (ja) |
Cited By (4)
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JP2018514502A (ja) * | 2015-05-13 | 2018-06-07 | エルジー・ケム・リミテッド | 異性化反応を用いたノルマルブテンの分離方法及びノルマルブテンを分離するための工程システム |
JP6360982B1 (ja) * | 2017-06-29 | 2018-07-18 | 住友化学株式会社 | イソブチレンの製造方法 |
JP2020524155A (ja) * | 2017-07-31 | 2020-08-13 | エルジー・ケム・リミテッド | ラフィネート−2の精製方法 |
JP2020528003A (ja) * | 2017-08-25 | 2020-09-17 | エルジー・ケム・リミテッド | 沸点差の小さい混合物の分離精製方法 |
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EP2560737B1 (en) * | 2010-04-21 | 2016-08-24 | Saudi Basic Industries Corporation | Distillation process and multi-column heat-integrated distillation system |
KR101458404B1 (ko) * | 2013-01-17 | 2014-11-05 | 대림산업 주식회사 | 폴리부텐의 제조 방법 |
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JP6140591B2 (ja) | 2013-11-21 | 2017-05-31 | 東洋エンジニアリング株式会社 | 蒸留装置 |
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EA020352B1 (ru) | 2014-10-30 |
BRPI1008827B1 (pt) | 2017-12-12 |
JP5323948B2 (ja) | 2013-10-23 |
CN101792363B (zh) | 2013-01-23 |
US7982086B2 (en) | 2011-07-19 |
TW201031458A (en) | 2010-09-01 |
EA201171005A1 (ru) | 2012-04-30 |
MY152010A (en) | 2014-08-15 |
KR101351164B1 (ko) | 2014-01-14 |
KR20110102381A (ko) | 2011-09-16 |
CN101792363A (zh) | 2010-08-04 |
TWI503156B (zh) | 2015-10-11 |
US20100197987A1 (en) | 2010-08-05 |
WO2010090790A1 (en) | 2010-08-12 |
BRPI1008827A2 (pt) | 2016-02-23 |
SG173508A1 (en) | 2011-09-29 |
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