ZA200504274B - Process for the purification of crude propene oxide - Google Patents
Process for the purification of crude propene oxide Download PDFInfo
- Publication number
- ZA200504274B ZA200504274B ZA200504274A ZA200504274A ZA200504274B ZA 200504274 B ZA200504274 B ZA 200504274B ZA 200504274 A ZA200504274 A ZA 200504274A ZA 200504274 A ZA200504274 A ZA 200504274A ZA 200504274 B ZA200504274 B ZA 200504274B
- Authority
- ZA
- South Africa
- Prior art keywords
- propene oxide
- methanol
- acetaldehyde
- propene
- crude
- Prior art date
Links
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims description 75
- 238000000034 method Methods 0.000 title claims description 39
- 238000000746 purification Methods 0.000 title claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 58
- 239000002904 solvent Substances 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 21
- 238000000605 extraction Methods 0.000 claims description 21
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 14
- 238000000895 extractive distillation Methods 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000006735 epoxidation reaction Methods 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- -1 hydroxide ions Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- 238000001577 simple distillation Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02026240A EP1424332A1 (en) | 2002-11-26 | 2002-11-26 | Process for the purification of crude propene oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504274B true ZA200504274B (en) | 2006-11-29 |
Family
ID=34354407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504274A ZA200504274B (en) | 2002-11-26 | 2005-05-25 | Process for the purification of crude propene oxide |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7049450B2 (es) |
| EP (2) | EP1424332A1 (es) |
| JP (1) | JP4705373B2 (es) |
| KR (1) | KR100938788B1 (es) |
| CN (2) | CN100500659C (es) |
| AU (1) | AU2003294723A1 (es) |
| BR (1) | BR0316554B1 (es) |
| CA (1) | CA2507071C (es) |
| ES (1) | ES2427541T3 (es) |
| MY (1) | MY145599A (es) |
| PL (1) | PL215260B1 (es) |
| RU (1) | RU2330032C2 (es) |
| WO (1) | WO2004048355A1 (es) |
| ZA (1) | ZA200504274B (es) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7323579B2 (en) | 2004-07-07 | 2008-01-29 | Basf Aktiengesellschaft | Separation of propylene oxide from a mixture comprising propylene oxide and methanol |
| US20060006054A1 (en) | 2004-07-07 | 2006-01-12 | Basf Aktiengesellshaft | Separation of propylene oxide from a mixture comprising propylene oxide and methanol |
| CN101084176B (zh) * | 2004-12-20 | 2012-12-05 | 赢创德固赛有限公司 | 回收甲醇的方法 |
| KR100866452B1 (ko) | 2004-12-20 | 2008-10-31 | 에보니크 데구사 게엠베하 | 메탄올 회수 방법 |
| JP4963022B2 (ja) * | 2005-11-25 | 2012-06-27 | 株式会社日本触媒 | エポキシ化合物の製造方法 |
| EP1973891B2 (en) * | 2005-12-27 | 2015-11-04 | Basf Se | A process for epoxidizing propene |
| ITMI20052491A1 (it) | 2005-12-27 | 2007-06-28 | Basf Ag | Un procedimento per la epossidazione del propene |
| DE102006025821A1 (de) | 2006-06-02 | 2007-12-06 | Degussa Gmbh | Ein Enzym zur Herstellung von Mehylmalonatsemialdehyd oder Malonatsemialdehyd |
| US8080678B2 (en) * | 2010-04-01 | 2011-12-20 | Lyondell Chemical Technology, L.P. | Purification of propylene oxide |
| DE102010015807A1 (de) | 2010-04-20 | 2011-10-20 | Evonik Degussa Gmbh | Biokatalytisches Oxidationsverfahren mit alkL-Genprodukt |
| JP2011246423A (ja) * | 2010-05-31 | 2011-12-08 | Sumitomo Chemical Co Ltd | オレフィンオキサイドの製造方法 |
| US8389750B2 (en) * | 2010-09-28 | 2013-03-05 | Lyondell Chemical Technology, L.P. | Purification of propylene oxide |
| US8859791B2 (en) * | 2010-10-11 | 2014-10-14 | China Petroleum & Chemical Corporation | Process for producing an alkylene oxide by olefin epoxidation |
| CN102093316B (zh) * | 2010-12-17 | 2013-06-12 | 中国海洋石油总公司 | 一种分离提纯环氧丙烷与甲醇的方法 |
| UA112980C2 (uk) | 2011-02-16 | 2016-11-25 | Евонік Дегусса Гмбх | Рідкі катіоніти |
| JP2012224608A (ja) * | 2011-04-08 | 2012-11-15 | Sumitomo Chemical Co Ltd | プロピレンオキサイドの取得方法 |
| WO2013011018A1 (de) | 2011-07-20 | 2013-01-24 | Evonik Degussa Gmbh | Oxidation und aminierung von primären alkoholen |
| EP2602328A1 (de) | 2011-12-05 | 2013-06-12 | Evonik Industries AG | Verfahren zur Oxidation von Alkanen unter Verwendung einer AlkB Alkan 1-Monooxygenase |
| EP2607479A1 (en) | 2011-12-22 | 2013-06-26 | Evonik Industries AG | Biotechnological production of alcohols and derivatives thereof |
| EP2607490A1 (de) | 2011-12-22 | 2013-06-26 | Evonik Industries AG | Verfahren zur verbesserten Abtrennung einer hydrophoben organischen Lösung von einem wässrigen Kulturmedium |
| EP2631298A1 (en) | 2012-02-22 | 2013-08-28 | Evonik Industries AG | Biotechnological method for producing butanol and butyric acid |
| EP2639308A1 (de) | 2012-03-12 | 2013-09-18 | Evonik Industries AG | Enzymatische omega-Oxidation und -Aminierung von Fettsäuren |
| EP2700448A1 (de) | 2012-08-21 | 2014-02-26 | Evonik Industries AG | Verzweigte Fettsäuren als flüssige Kationenaustauscher |
| EP2730655A1 (de) | 2012-11-12 | 2014-05-14 | Evonik Industries AG | Verfahren zur Umsetzung eines Carbonsäureesters unter Verwendung BioH-defizienter Zellen |
| EP2746400A1 (de) | 2012-12-21 | 2014-06-25 | Evonik Industries AG | Herstellung von Aminen und Diaminen aus einer Carbonsäure oder Dicarbonsäure oder eines Monoesters davon |
| EP2746397A1 (de) | 2012-12-21 | 2014-06-25 | Evonik Industries AG | Herstellung von Omega-Aminofettsäuren |
| US9593090B2 (en) | 2013-07-29 | 2017-03-14 | Lyondell Chemical Technology, L.P. | Alkylene oxide separation systems, methods, and apparatuses |
| CN104926759A (zh) * | 2014-03-17 | 2015-09-23 | 中国石油化工股份有限公司 | 制备环氧丙烷的方法 |
| WO2016113193A1 (en) | 2015-01-14 | 2016-07-21 | Evonik Degussa Gmbh | Integrated process for making propene oxide and an alkyl tert-butyl ether |
| CN107428712A (zh) | 2015-01-14 | 2017-12-01 | 赢创德固赛有限公司 | 用于制备氧化丙烯和烷基叔丁基醚的整合方法 |
| CN106397366B (zh) * | 2015-08-03 | 2019-06-11 | 中国石油化工股份有限公司 | 环氧丙烷的纯化方法 |
| CN106397364B (zh) * | 2015-08-03 | 2019-06-11 | 中国石油化工股份有限公司 | 环氧丙烷的纯化装置 |
| WO2017089075A1 (de) | 2015-11-25 | 2017-06-01 | Evonik Degussa Gmbh | Verfahren zur herstellung von 1,2-propandiol aus propen und wasserstoffperoxid |
| TWI707847B (zh) | 2015-11-26 | 2020-10-21 | 德商贏創運營有限公司 | 丙烯之環氧化方法 |
| HUE054720T2 (hu) | 2015-11-26 | 2021-09-28 | Evonik Operations Gmbh | Eljárás és reaktor propén epoxidálására |
| EA033968B1 (ru) | 2015-11-26 | 2019-12-16 | Эвоник Дегусса Гмбх | Способ эпоксидирования олефина |
| WO2017089080A1 (en) | 2015-11-26 | 2017-06-01 | Evonik Degussa Gmbh | Process for purifying propene oxide |
| PL3383856T3 (pl) * | 2015-12-02 | 2020-10-19 | Evonik Operations Gmbh | Sposób epoksydowania propenu |
| CN108473453B (zh) | 2016-01-19 | 2020-08-04 | 赢创运营有限公司 | 烯烃的环氧化方法 |
| CN105906584B (zh) * | 2016-03-01 | 2018-07-06 | 江苏怡达化学股份有限公司 | 脱除环氧丙烷反应混合物中的醛类的方法 |
| HUE052019T2 (hu) | 2016-03-21 | 2021-04-28 | Evonik Operations Gmbh | Eljárás propén epoxidálására |
| CN107286118A (zh) * | 2016-04-12 | 2017-10-24 | 中国石油化工股份有限公司 | 环氧丙烷的精制装置 |
| CN107286119B (zh) * | 2016-04-12 | 2020-10-16 | 中国石油化工股份有限公司 | 环氧丙烷的精制方法 |
| EP3246323A1 (en) | 2016-05-17 | 2017-11-22 | Evonik Degussa GmbH | Integrated process for making propene oxide from propane |
| MX2019000853A (es) | 2016-07-20 | 2019-09-19 | Basf Se | Un proceso para purificar oxido de propileno. |
| RU2740188C1 (ru) * | 2016-07-20 | 2021-01-12 | Басф Се | Способ очистки пропиленоксида |
| CN106496163B (zh) * | 2016-10-21 | 2019-01-22 | 中国天辰工程有限公司 | 一种环氧丙烷的分离提纯方法 |
| CN108017597B (zh) * | 2016-11-04 | 2021-06-22 | 中国石油化工股份有限公司 | 环氧丁烷组合物 |
| CN108017598B (zh) * | 2016-11-04 | 2021-06-22 | 中国石油化工股份有限公司 | 环氧丁烷组合物及其制备方法 |
| WO2018205244A1 (en) * | 2017-05-12 | 2018-11-15 | Evonik Degussa Gmbh | Process for the epoxidation of propene |
| EP3406603A1 (en) | 2017-05-22 | 2018-11-28 | Evonik Degussa GmbH | Process for the epoxidation of propene |
| EP3438101A1 (en) | 2017-08-01 | 2019-02-06 | Evonik Degussa GmbH | Process for the epoxidation of propene |
| CN107686469A (zh) * | 2017-09-28 | 2018-02-13 | 万华化学集团股份有限公司 | 一种通过反应精馏精制环氧丙烷的方法 |
| CN109970686B (zh) * | 2019-04-26 | 2021-05-25 | 江苏扬农化工集团有限公司 | 一种低温等离子体改性材料脱除环氧丙烷反应液中醛酮酯类杂质的方法 |
| RU2722835C9 (ru) * | 2019-10-30 | 2020-09-03 | Акционерное общество "Химтэк Инжиниринг" | Способ очистки оксида пропилена от примесей карбонильных и карбоксильных соединений |
| CN113801076A (zh) * | 2020-06-16 | 2021-12-17 | 江苏怡达化学股份有限公司 | 环氧丙烷精馏工艺 |
| WO2022167284A1 (en) | 2021-02-03 | 2022-08-11 | Evonik Operations Gmbh | Process for the epoxidation of propene |
| EP4063355A1 (en) | 2021-03-22 | 2022-09-28 | Evonik Operations GmbH | Integrated process and plant for making styrene and propene oxide |
| EP4337645A1 (en) | 2021-05-10 | 2024-03-20 | Evonik Operations GmbH | An integrated plant and an integrated process for making propene oxide |
| CN113651776B (zh) * | 2021-08-06 | 2023-10-17 | 中触媒新材料股份有限公司 | 一种含醛类杂质的化合物的纯化剂及其应用 |
| CN113512014B (zh) * | 2021-08-06 | 2022-11-25 | 中触媒新材料股份有限公司 | 一种含醛类杂质的环氧丙烷纯化方法 |
| EP4166545A1 (en) | 2021-10-14 | 2023-04-19 | Evonik Operations GmbH | Process for making propene oxide |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE681866C (de) * | 1935-12-05 | 1939-10-03 | I G Farbenindustrie Akt Ges | Verfahren zur Reinigung von aldehydhaltigen Alkylenoyden |
| US2622060A (en) * | 1950-01-26 | 1952-12-16 | Celanese Corp | Purification of 1,2-propylene oxide |
| US3149131A (en) * | 1960-07-15 | 1964-09-15 | Pittsburgh Plate Glass Co | Purification of oxiranes by reduction of carbonyl impurittes with trivalent nitrogencompounds |
| DE2810662C3 (de) * | 1978-03-11 | 1982-03-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Reinigung eines Epoxids oder eines solches enthaltenden Gemisches |
| IT1152299B (it) * | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'espossidazione di composti olefinici |
| US4691035A (en) * | 1986-04-14 | 1987-09-01 | Texaco Inc. | Purification of propylene oxide by treatment with a selected base and inert salt |
| US5116466A (en) * | 1991-11-01 | 1992-05-26 | Texaco Chemical Company | Propylene oxide purification by extractive distillation |
| US5116465A (en) * | 1991-11-01 | 1992-05-26 | Texaco Chemical Company | Removal of water, methanol and acetone from propylene oxide by extractive distillation |
| DE69306607D1 (de) * | 1992-02-20 | 1997-01-30 | Arco Chem Tech | Reinigung von niedrigem Alkylenoxyd |
| US5958192A (en) * | 1997-08-27 | 1999-09-28 | Huntsman Specialty Chemicals Corporation | Purification of propylene oxide using ethylene glycol monomethyl ether as an extractive distillation agent |
| US5849938A (en) * | 1997-09-02 | 1998-12-15 | Arco Chemical Technology, L.P. | Separation of methanol and propylene oxide from a reaction mixture |
| DE69929415T2 (de) * | 1999-08-06 | 2006-09-21 | Repsol Quimica S.A. | Verfahren zur kontinuierlichen Herstellung von Propylenoxid und weiteren Alkenoxiden |
| IT1318680B1 (it) * | 2000-08-11 | 2003-08-27 | Enichem Spa | Processo per la produzione in continuo di ossidi olefinici. |
-
2002
- 2002-11-26 EP EP02026240A patent/EP1424332A1/en not_active Withdrawn
-
2003
- 2003-11-20 MY MYPI20034465A patent/MY145599A/en unknown
- 2003-11-25 WO PCT/EP2003/013212 patent/WO2004048355A1/en active Application Filing
- 2003-11-25 CA CA2507071A patent/CA2507071C/en not_active Expired - Fee Related
- 2003-11-25 PL PL376948A patent/PL215260B1/pl unknown
- 2003-11-25 BR BRPI0316554-0A patent/BR0316554B1/pt not_active IP Right Cessation
- 2003-11-25 RU RU2005120163/04A patent/RU2330032C2/ru active
- 2003-11-25 AU AU2003294723A patent/AU2003294723A1/en not_active Abandoned
- 2003-11-25 ES ES03785659T patent/ES2427541T3/es not_active Expired - Lifetime
- 2003-11-25 JP JP2004554449A patent/JP4705373B2/ja not_active Expired - Fee Related
- 2003-11-25 CN CNB2003801039865A patent/CN100500659C/zh not_active Expired - Lifetime
- 2003-11-25 KR KR1020057009390A patent/KR100938788B1/ko active IP Right Grant
- 2003-11-25 CN CN2008101302018A patent/CN101298443B/zh not_active Expired - Lifetime
- 2003-11-25 EP EP03785659.8A patent/EP1567512B1/en not_active Expired - Lifetime
- 2003-11-26 US US10/723,270 patent/US7049450B2/en not_active Expired - Fee Related
-
2005
- 2005-05-25 ZA ZA200504274A patent/ZA200504274B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2427541T3 (es) | 2013-10-30 |
| JP4705373B2 (ja) | 2011-06-22 |
| CN100500659C (zh) | 2009-06-17 |
| CA2507071A1 (en) | 2004-06-10 |
| RU2330032C2 (ru) | 2008-07-27 |
| CN101298443B (zh) | 2011-07-27 |
| EP1424332A1 (en) | 2004-06-02 |
| EP1567512A1 (en) | 2005-08-31 |
| US20040106811A1 (en) | 2004-06-03 |
| US7049450B2 (en) | 2006-05-23 |
| MY145599A (en) | 2012-02-29 |
| BR0316554A (pt) | 2005-10-04 |
| AU2003294723A1 (en) | 2004-06-18 |
| KR20050086795A (ko) | 2005-08-30 |
| PL376948A1 (pl) | 2006-01-09 |
| EP1567512B1 (en) | 2013-06-12 |
| CN101298443A (zh) | 2008-11-05 |
| BR0316554B1 (pt) | 2014-04-15 |
| AU2003294723A8 (en) | 2004-06-18 |
| KR100938788B1 (ko) | 2010-01-27 |
| RU2005120163A (ru) | 2006-05-10 |
| CA2507071C (en) | 2011-07-05 |
| WO2004048355A1 (en) | 2004-06-10 |
| JP2006513174A (ja) | 2006-04-20 |
| PL215260B1 (pl) | 2013-11-29 |
| CN1714087A (zh) | 2005-12-28 |
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