ZA200505813B - Method of making high purity phenol - Google Patents
Method of making high purity phenol Download PDFInfo
- Publication number
- ZA200505813B ZA200505813B ZA200505813A ZA200505813A ZA200505813B ZA 200505813 B ZA200505813 B ZA 200505813B ZA 200505813 A ZA200505813 A ZA 200505813A ZA 200505813 A ZA200505813 A ZA 200505813A ZA 200505813 B ZA200505813 B ZA 200505813B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenol
- product
- contaminant
- product stream
- sec
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 157
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000000047 product Substances 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 43
- 239000000356 contaminant Substances 0.000 claims description 43
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 239000007795 chemical reaction product Substances 0.000 claims description 38
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 36
- 238000007254 oxidation reaction Methods 0.000 claims description 36
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 32
- 230000002378 acidificating effect Effects 0.000 claims description 27
- 239000006227 byproduct Substances 0.000 claims description 24
- 239000010457 zeolite Substances 0.000 claims description 21
- 238000000746 purification Methods 0.000 claims description 20
- 238000003776 cleavage reaction Methods 0.000 claims description 19
- 238000000354 decomposition reaction Methods 0.000 claims description 17
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 12
- GFAZHVHNLUBROE-UHFFFAOYSA-N 1-hydroxybutan-2-one Chemical group CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 claims description 9
- KHADDDTZDWSVIZ-UHFFFAOYSA-N butan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CCC(C)C1=CC=CC=C1 KHADDDTZDWSVIZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003456 ion exchange resin Substances 0.000 claims description 9
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 37
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 15
- 238000000926 separation method Methods 0.000 description 15
- 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 description 13
- 229910021536 Zeolite Inorganic materials 0.000 description 13
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 12
- 239000003729 cation exchange resin Substances 0.000 description 11
- 229910052750 molybdenum Inorganic materials 0.000 description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 239000011733 molybdenum Substances 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 3
- KJHYAEZMOHLVCH-UHFFFAOYSA-N 2-ethyl-1-benzofuran Chemical compound C1=CC=C2OC(CC)=CC2=C1 KJHYAEZMOHLVCH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001907 coumarones Chemical class 0.000 description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- YGBXXWTZWLALGR-UHFFFAOYSA-N 2,3-Dimethylbenzofuran Chemical compound C1=CC=C2C(C)=C(C)OC2=C1 YGBXXWTZWLALGR-UHFFFAOYSA-N 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910001657 ferrierite group Inorganic materials 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052680 mordenite Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 238000004438 BET method Methods 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229910000873 Beta-alumina solid electrolyte Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- MHWARLQBKUPZMN-UHFFFAOYSA-N butylbenzene;hydrogen peroxide Chemical compound OO.CCCCC1=CC=CC=C1 MHWARLQBKUPZMN-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- -1 methyl ethyl Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44552803P | 2003-02-06 | 2003-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505813B true ZA200505813B (en) | 2006-03-29 |
Family
ID=32869374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505813A ZA200505813B (en) | 2003-02-06 | 2006-02-13 | Method of making high purity phenol |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7205442B2 (ko) |
| EP (1) | EP1594829A1 (ko) |
| JP (1) | JP4651612B2 (ko) |
| KR (1) | KR20050098885A (ko) |
| CN (1) | CN100378053C (ko) |
| BR (1) | BRPI0407115A (ko) |
| MY (1) | MY136990A (ko) |
| TW (1) | TWI355374B (ko) |
| WO (1) | WO2004072008A1 (ko) |
| ZA (1) | ZA200505813B (ko) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7034192B2 (en) * | 2004-03-24 | 2006-04-25 | Sunoco Inc. (R&M) | Method for removal of acetol from phenol |
| US7544845B2 (en) * | 2006-04-18 | 2009-06-09 | Ineos Phenol Gmbh & Co. Kg | Process for treating phenol |
| US8884067B2 (en) | 2009-02-26 | 2014-11-11 | Exxonmobil Chemical Patents Inc. | Phenol and cyclohexanone mixtures |
| CN105646156B (zh) | 2010-09-14 | 2018-07-13 | 埃克森美孚化学专利公司 | 用于制备苯酚的方法 |
| SG187647A1 (en) * | 2010-09-14 | 2013-03-28 | Exxonmobil Chem Patents Inc | Phenol compositions |
| SG10201509481UA (en) | 2010-09-14 | 2015-12-30 | Exxonmobil Chem Patents Inc | Processes for producing phenol |
| WO2012036824A1 (en) | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Oxidation of alkylbenzenes and cycloalkylbenzenes |
| US9242918B2 (en) * | 2010-09-14 | 2016-01-26 | Exxonmobil Chemical Patents Inc. | Dehydrogenation processes and phenol compositions |
| SG186345A1 (en) | 2010-09-14 | 2013-01-30 | Exxonmobil Chem Patents Inc | Processes for producing phenol |
| BR112014014294B1 (pt) | 2011-12-28 | 2020-10-27 | Dow Global Technologies Llc | catalisador na forma de contas de polímero vinil aromático reticulado |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB676770A (en) | 1948-06-05 | 1952-08-06 | Distillers Co Yeast Ltd | Improvements in or relating to phenol production |
| US2948758A (en) * | 1954-07-08 | 1960-08-09 | Hercules Powder Co Ltd | Purification of phenol by adsorption of impurities |
| GB777961A (en) | 1954-07-14 | 1957-07-03 | British Tar Products Ltd | Improvements relating to the desulphurisation of phenolic materials |
| US3029294A (en) * | 1959-02-27 | 1962-04-10 | Hercules Powder Co Ltd | Purification of phenol |
| GB920864A (en) | 1960-08-19 | 1963-03-13 | Distillers Co Yeast Ltd | Purification of phenol |
| FR1445829A (fr) | 1964-08-05 | 1966-07-15 | Universal Oil Prod Co | Nouveau procédé de purification de phénols |
| CH473751A (de) | 1965-06-29 | 1969-06-15 | Pecka Karel | Verfahren zur Feinstreinigung von nach dem Cumolverfahren hergestelltem Phenol |
| GB1148907A (en) * | 1965-11-26 | 1969-04-16 | Ici Ltd | Purification of phenol |
| US4097367A (en) * | 1977-07-25 | 1978-06-27 | Mobil Oil Corporation | Conversion of olefinic naphtha |
| JPS5865234A (ja) | 1981-10-12 | 1983-04-18 | Mitsui Petrochem Ind Ltd | フエノ−ル類の精製方法 |
| JPS62114922A (ja) | 1985-11-13 | 1987-05-26 | 大日本インキ化学工業株式会社 | フエノ−ルとアセトンおよびメチルエチルケトンとの製造法 |
| JPH05286879A (ja) * | 1992-04-03 | 1993-11-02 | Mitsui Petrochem Ind Ltd | 高純度フェノールの製造方法 |
| TW237445B (ko) | 1992-07-07 | 1995-01-01 | Sumitomo Chemical Co | |
| RU2111203C1 (ru) * | 1993-12-01 | 1998-05-20 | Закошанский Владимир Михайлович | Способ очистки фенола от органических примесей |
| US5414154A (en) * | 1994-06-06 | 1995-05-09 | Alliedsignal Inc. | Phenol with low levels of methylbenzofuran |
| US5491268A (en) * | 1994-09-23 | 1996-02-13 | General Electric Company | Process for removal of acidic compounds from phenol process streams |
| DE19946887A1 (de) | 1999-09-30 | 2001-04-05 | Phenolchemie Gmbh & Co Kg | Verfahren zur Herstellung von Phenol, Methylethylketon und Aceton |
| DE19946888A1 (de) | 1999-09-30 | 2001-04-05 | Phenolchemie Gmbh & Co Kg | Verfahren zur Herstellung von Phenol, Aceton und Methylethylketon |
| DE19951373A1 (de) * | 1999-10-26 | 2001-05-03 | Phenolchemie Gmbh & Co Kg | Verfahren zur Entfernung von Verunreinigungen aus Phenol mittels zumindest eines sauren Katalysators |
| RU2217408C2 (ru) * | 2002-02-08 | 2003-11-27 | Общество с ограниченной ответственностью "Петрофенол" | Способ и катализатор очистки фенола |
-
2004
- 2004-01-21 US US10/761,591 patent/US7205442B2/en not_active Expired - Fee Related
- 2004-02-04 JP JP2006503299A patent/JP4651612B2/ja not_active Expired - Fee Related
- 2004-02-04 WO PCT/US2004/003106 patent/WO2004072008A1/en active Search and Examination
- 2004-02-04 MY MYPI20040333A patent/MY136990A/en unknown
- 2004-02-04 KR KR1020057014300A patent/KR20050098885A/ko active IP Right Grant
- 2004-02-04 BR BR0407115-8A patent/BRPI0407115A/pt not_active IP Right Cessation
- 2004-02-04 EP EP04708153A patent/EP1594829A1/en not_active Withdrawn
- 2004-02-04 CN CNB2004800036313A patent/CN100378053C/zh not_active Expired - Fee Related
- 2004-02-04 TW TW093102507A patent/TWI355374B/zh not_active IP Right Cessation
-
2006
- 2006-02-13 ZA ZA200505813A patent/ZA200505813B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7205442B2 (en) | 2007-04-17 |
| KR20050098885A (ko) | 2005-10-12 |
| EP1594829A1 (en) | 2005-11-16 |
| JP4651612B2 (ja) | 2011-03-16 |
| TW200424161A (en) | 2004-11-16 |
| MY136990A (en) | 2008-12-31 |
| BRPI0407115A (pt) | 2006-01-10 |
| US20040158105A1 (en) | 2004-08-12 |
| CN1747919A (zh) | 2006-03-15 |
| TWI355374B (en) | 2012-01-01 |
| JP2006517229A (ja) | 2006-07-20 |
| CN100378053C (zh) | 2008-04-02 |
| WO2004072008A1 (en) | 2004-08-26 |
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