JP4778517B2 - 断熱反応器での未精製メタノールからのジメチルエーテルの製造方法 - Google Patents
断熱反応器での未精製メタノールからのジメチルエーテルの製造方法 Download PDFInfo
- Publication number
- JP4778517B2 JP4778517B2 JP2007536604A JP2007536604A JP4778517B2 JP 4778517 B2 JP4778517 B2 JP 4778517B2 JP 2007536604 A JP2007536604 A JP 2007536604A JP 2007536604 A JP2007536604 A JP 2007536604A JP 4778517 B2 JP4778517 B2 JP 4778517B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- dimethyl ether
- group
- adiabatic reactor
- zeolite
- 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.)
- Expired - Fee Related
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 210
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title claims description 164
- 238000004519 manufacturing process Methods 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 31
- 239000003054 catalyst Substances 0.000 claims description 171
- 239000010457 zeolite Substances 0.000 claims description 115
- 229910021536 Zeolite Inorganic materials 0.000 claims description 108
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 108
- 230000002209 hydrophobic effect Effects 0.000 claims description 60
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 238000006297 dehydration reaction Methods 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000001768 cations Chemical class 0.000 claims description 23
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 18
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 description 39
- 150000002430 hydrocarbons Chemical class 0.000 description 39
- 239000006227 byproduct Substances 0.000 description 33
- 239000002253 acid Substances 0.000 description 22
- 238000011049 filling Methods 0.000 description 18
- 229910001593 boehmite Inorganic materials 0.000 description 15
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 229910017604 nitric acid Inorganic materials 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 239000010419 fine particle Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052680 mordenite Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 235000010344 sodium nitrate Nutrition 0.000 description 5
- 239000004317 sodium nitrate Substances 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 3
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- -1 USY Chemical compound 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Chemical compound [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2004-0082721 | 2004-10-15 | ||
| KR1020040082721A KR100629939B1 (ko) | 2004-10-15 | 2004-10-15 | 단열반응기에서 미정제 메탄올로부터 디메틸에테르의제조방법 |
| PCT/KR2005/002751 WO2006041253A1 (en) | 2004-10-15 | 2005-08-19 | Process for preparing dimethyl ether from crude methanol in an adiabatic reactor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008516943A JP2008516943A (ja) | 2008-05-22 |
| JP2008516943A5 JP2008516943A5 (enExample) | 2008-08-07 |
| JP4778517B2 true JP4778517B2 (ja) | 2011-09-21 |
Family
ID=36148529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007536604A Expired - Fee Related JP4778517B2 (ja) | 2004-10-15 | 2005-08-19 | 断熱反応器での未精製メタノールからのジメチルエーテルの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20090023958A1 (enExample) |
| EP (1) | EP1799630A4 (enExample) |
| JP (1) | JP4778517B2 (enExample) |
| KR (1) | KR100629939B1 (enExample) |
| CN (1) | CN101119952A (enExample) |
| AU (1) | AU2005294990A1 (enExample) |
| TW (1) | TW200621697A (enExample) |
| WO (1) | WO2006041253A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5632438B2 (ja) * | 2006-08-30 | 2014-11-26 | 日揮株式会社 | ジメチルエーテルまたはメタノールを原料とする低級炭化水素合成用カルシウム化合物含有ゼオライト触媒の調製方法 |
| JP2008080301A (ja) * | 2006-08-30 | 2008-04-10 | Jgc Corp | アルカリ土類金属化合物含有ゼオライト触媒およびその調製方法、並びに、低級炭化水素の製造方法 |
| TWI406707B (zh) | 2006-08-30 | 2013-09-01 | Jgc Corp | 含鹼土類金屬化合物之沸石催化劑及其調製方法與再生方法、以及低級烴之製造方法 |
| EP2167452A1 (en) * | 2007-06-25 | 2010-03-31 | Mcneff Research Consultants, Inc. | Catalysts, systems and methods for ether synthesis |
| US8697893B2 (en) | 2008-12-22 | 2014-04-15 | Sartec Corporation | Systems and methods for producing fuels and fuel precursors from carbohydrates |
| CN101550067B (zh) * | 2009-05-15 | 2013-03-20 | 新奥新能(北京)科技有限公司 | 两段式二甲醚生产方法 |
| EP2292578A1 (en) | 2009-09-03 | 2011-03-09 | BP Chemicals Limited | Process for producing acetic acid and dimethyl ether using a zeolite catalyst |
| CN102666460A (zh) | 2009-11-17 | 2012-09-12 | 鲁奇有限责任公司 | 由粗甲醇制备二甲醚 |
| EP2322494B1 (de) | 2009-11-17 | 2013-01-09 | Lurgi GmbH | Herstellung von Dimethylether aus Rohmethanol |
| DE102009053357A1 (de) * | 2009-11-17 | 2011-05-26 | Lurgi Gmbh | Herstellung von Dimethylether aus Rohmethanol |
| US9595186B2 (en) * | 2010-01-04 | 2017-03-14 | Samsung Electronics Co., Ltd. | Electronic device combining functions of touch screen and remote control and operation control method thereof |
| WO2011095270A1 (en) * | 2010-02-04 | 2011-08-11 | Haldor Topsøe A/S | Process for the preparation of dimethyl ether |
| CN102463134B (zh) * | 2010-11-04 | 2013-08-28 | 中国石油化工股份有限公司 | 一种甲醇脱水制二甲醚催化剂及其制备方法和应用 |
| JP2012120977A (ja) * | 2010-12-08 | 2012-06-28 | Mitsubishi Chemicals Corp | 珪質固体触媒の製造方法及び低級炭化水素の製造方法 |
| DE102011114228A1 (de) | 2011-09-23 | 2013-03-28 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Gekühlter Reaktor zur Herstellung von Dimethylether aus Methanol |
| EP2817283A1 (en) * | 2012-02-23 | 2014-12-31 | BP Chemicals Limited | Process for the production of acetic acid and diemthyl ether |
| DE102012018341A1 (de) * | 2012-09-15 | 2014-05-15 | Thyssenkrupp Uhde Gmbh | Verfahren zur Herstellung von Dimethylether und dafür geeignete Vorrichtung |
| US9247281B2 (en) | 2013-01-11 | 2016-01-26 | Htc Corporation | Handheld electronic device having universal remote control mechanism and operation method of the same |
| HK1221351A1 (zh) * | 2013-09-24 | 2017-05-26 | Fibar Group S.A. | 无触摸滑动控制 |
| DE102014118966A1 (de) | 2014-12-18 | 2015-12-31 | L’AIR LIQUIDE Société Anonyme pour l’Etude et l’Exploitation des Procédés Georges Claude | Anlage, Verfahren und Katalysator zur Herstellung von Dimethylether |
| KR102467394B1 (ko) * | 2016-05-24 | 2022-11-15 | 에스케이이노베이션 주식회사 | 단열 반응기를 이용하여 2,3-부탄디올로부터 1,3-부타디엔 및 메틸에틸케톤을 제조하는 방법 |
| US10239812B2 (en) | 2017-04-27 | 2019-03-26 | Sartec Corporation | Systems and methods for synthesis of phenolics and ketones |
| CN109092349A (zh) * | 2017-06-20 | 2018-12-28 | 高化学技术株式会社 | 用于制备乙二醇二甲醚的催化剂及其制备方法和应用 |
| JP2021508286A (ja) * | 2017-12-20 | 2021-03-04 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | ジメチルエーテルを製造するための触媒システムおよび方法 |
| US10696923B2 (en) | 2018-02-07 | 2020-06-30 | Sartec Corporation | Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids |
| US10544381B2 (en) | 2018-02-07 | 2020-01-28 | Sartec Corporation | Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid |
| CN115368375B (zh) * | 2021-05-19 | 2024-01-26 | 中国石油化工股份有限公司 | 一种制备氧杂-降冰片烯的方法 |
| KR102834277B1 (ko) | 2023-06-22 | 2025-07-17 | (주)송천이앤씨 | 모듈러 보강대용 체결판 지그 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123448A (en) * | 1977-06-01 | 1978-10-31 | Continental Oil Company | Adiabatic reactor |
| BR8303437A (pt) * | 1982-07-01 | 1984-02-07 | Du Pont | Processo para a preparacao de eter dimetilico pela desidratacao catalitica de metanol |
| AU603070B2 (en) * | 1986-11-18 | 1990-11-08 | Rwe-Dea Aktiengesellschaft Fur Mineraloel Und Chemie | Process for the purification of dimethylether |
| US4885405A (en) * | 1987-12-10 | 1989-12-05 | Horst Dornhagen | Process for the production of pure dimethylether and a catalyst used in the process |
| US5684213A (en) * | 1996-03-25 | 1997-11-04 | Chemical Research & Licensing Company | Method for the preparation of dialkyl ethers |
| US6608114B1 (en) * | 2002-03-13 | 2003-08-19 | Air Products And Chemicals, Inc. | Process to produce DME |
| KR100454091B1 (ko) * | 2002-12-11 | 2004-10-26 | 한국화학연구원 | 미정제 메탄올로부터 디메틸에테르의 제조방법 |
| KR100501922B1 (ko) * | 2003-02-19 | 2005-07-18 | 에스케이 주식회사 | 메탄올로부터 디메틸에테르의 제조방법 |
-
2004
- 2004-10-15 KR KR1020040082721A patent/KR100629939B1/ko not_active Expired - Fee Related
-
2005
- 2005-08-19 US US11/665,112 patent/US20090023958A1/en not_active Abandoned
- 2005-08-19 EP EP05825764A patent/EP1799630A4/en not_active Withdrawn
- 2005-08-19 WO PCT/KR2005/002751 patent/WO2006041253A1/en not_active Ceased
- 2005-08-19 JP JP2007536604A patent/JP4778517B2/ja not_active Expired - Fee Related
- 2005-08-19 AU AU2005294990A patent/AU2005294990A1/en not_active Abandoned
- 2005-08-19 CN CNA2005800347590A patent/CN101119952A/zh active Pending
- 2005-10-14 TW TW094135885A patent/TW200621697A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101119952A (zh) | 2008-02-06 |
| WO2006041253A1 (en) | 2006-04-20 |
| TW200621697A (en) | 2006-07-01 |
| KR100629939B1 (ko) | 2006-09-28 |
| EP1799630A1 (en) | 2007-06-27 |
| EP1799630A4 (en) | 2009-12-02 |
| JP2008516943A (ja) | 2008-05-22 |
| AU2005294990A1 (en) | 2006-04-20 |
| US20090023958A1 (en) | 2009-01-22 |
| KR20060033551A (ko) | 2006-04-19 |
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