KR20050097550A - 알킬벤젠 하이드로퍼옥사이드 생산방법 - Google Patents
알킬벤젠 하이드로퍼옥사이드 생산방법 Download PDFInfo
- Publication number
- KR20050097550A KR20050097550A KR1020057014920A KR20057014920A KR20050097550A KR 20050097550 A KR20050097550 A KR 20050097550A KR 1020057014920 A KR1020057014920 A KR 1020057014920A KR 20057014920 A KR20057014920 A KR 20057014920A KR 20050097550 A KR20050097550 A KR 20050097550A
- Authority
- KR
- South Korea
- Prior art keywords
- oxidation
- hydroperoxide
- alkylbenzene
- ammonia
- alkali metal
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- -1 alkylbenzene hydroperoxides Chemical class 0.000 title claims abstract description 9
- 230000008569 process Effects 0.000 title claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 113
- 230000003647 oxidation Effects 0.000 claims abstract description 106
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 27
- 230000001590 oxidative effect Effects 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000004996 alkyl benzenes Chemical class 0.000 claims abstract description 17
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 49
- 239000002585 base Substances 0.000 claims description 42
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 22
- 229910021529 ammonia Inorganic materials 0.000 claims description 19
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical group 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 239000002994 raw material Substances 0.000 abstract description 8
- 150000002432 hydroperoxides Chemical class 0.000 abstract description 3
- 239000012074 organic phase Substances 0.000 abstract description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 33
- 238000002474 experimental method Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 13
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- KHADDDTZDWSVIZ-UHFFFAOYSA-N butan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CCC(C)C1=CC=CC=C1 KHADDDTZDWSVIZ-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FTZBYXCNXOPJEL-UHFFFAOYSA-N 2-methyl-1-phenylbutan-2-ol Chemical compound CCC(C)(O)CC1=CC=CC=C1 FTZBYXCNXOPJEL-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—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
- C07C37/08—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
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44752603P | 2003-02-14 | 2003-02-14 | |
| US60/447,526 | 2003-02-14 | ||
| US10/761,641 US7141703B2 (en) | 2003-02-14 | 2004-01-21 | Process for producing phenol and ketone using neutralizing base |
| US10/761,641 | 2004-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050097550A true KR20050097550A (ko) | 2005-10-07 |
Family
ID=32853507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057014920A Ceased KR20050097550A (ko) | 2003-02-14 | 2004-02-11 | 알킬벤젠 하이드로퍼옥사이드 생산방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7141703B2 (enExample) |
| EP (1) | EP1594838A1 (enExample) |
| JP (1) | JP4912870B2 (enExample) |
| KR (1) | KR20050097550A (enExample) |
| BR (1) | BRPI0407404A (enExample) |
| MY (1) | MY139447A (enExample) |
| TW (1) | TW200508188A (enExample) |
| WO (1) | WO2004074241A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007106747A (ja) * | 2005-09-15 | 2007-04-26 | Sumitomo Chemical Co Ltd | アルキルベンゼンハイドロパーオキサイドの製造方法 |
| US7326815B2 (en) * | 2005-12-27 | 2008-02-05 | Exxonmobil Chemical Patents Inc. | Selective oxidation of alkylbenzenes |
| CN101511784A (zh) * | 2006-08-03 | 2009-08-19 | 埃克森美孚化学专利公司 | 烷基芳族化合物的氧化方法 |
| WO2008062644A1 (fr) | 2006-11-21 | 2008-05-29 | Mitsui Chemicals, Inc. | Procédé de fabrication d'un composé aromatique alkylé et procédé de fabrication de phénol |
| TW200846312A (en) * | 2007-02-22 | 2008-12-01 | Exxonmobil Chem Patents Inc | Oxidation of sec-butylbenzene and production of phenol and methyl ethyl ketone |
| JP5072951B2 (ja) * | 2007-02-23 | 2012-11-14 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法 |
| CN101687784B (zh) * | 2007-08-22 | 2014-11-12 | 埃克森美孚化学专利公司 | 烃的氧化 |
| WO2009058527A1 (en) * | 2007-10-31 | 2009-05-07 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| WO2009058531A1 (en) * | 2007-10-31 | 2009-05-07 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| EP2292573B1 (en) | 2008-06-10 | 2018-01-10 | Mitsui Chemicals, Inc. | Method for producing an alkylated aromatic compound and method for producing phenol |
| CN102076648A (zh) * | 2008-08-26 | 2011-05-25 | 埃克森美孚化学专利公司 | 用于生产烷基苯氢过氧化物的方法 |
| WO2010042273A1 (en) * | 2008-10-10 | 2010-04-15 | Exxonmobil Chemical Patents Inc. | Oxidation of hydrocarbons |
| CN102197009B (zh) * | 2008-10-23 | 2014-02-12 | 三井化学株式会社 | 烷基化芳香族化合物的制造方法、枯烯的制造方法以及苯酚的制造方法 |
| KR20140015548A (ko) | 2008-12-15 | 2014-02-06 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 알킬방향족 화합물의 산화 |
| WO2010106967A1 (ja) | 2009-03-19 | 2010-09-23 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法およびフェノールの製造方法 |
| CN102482211A (zh) | 2009-08-28 | 2012-05-30 | 埃克森美孚化学专利公司 | 烃的氧化 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2632773A (en) | 1947-04-01 | 1953-03-24 | Hercules Powder Co Ltd | Manufacture of peroxidic compounds |
| US3187055A (en) * | 1948-03-19 | 1965-06-01 | Hercules Powder Co Ltd | Manufacture of peroxidic compounds |
| US2632026A (en) | 1950-02-18 | 1953-03-17 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
| US2757209A (en) | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
| NL136649C (enExample) * | 1966-11-03 | |||
| US3907901A (en) * | 1969-07-14 | 1975-09-23 | Allied Chem | Continuous process for preparing cumene hydroperoxide |
| US4016213A (en) * | 1971-05-03 | 1977-04-05 | Allied Chemical Corporation | Recovery of phenol, acetone and dimethyl phenyl carbinol from cumene oxidation product |
| DE2300903A1 (de) | 1972-01-10 | 1973-08-02 | Union Carbide Corp | Verfahren zur herstellung von butylbenzolhydroperoxid und dessen verwendung zur herstellung von phenol, acetophenon und methylaethylketon |
| US4358618A (en) | 1981-06-22 | 1982-11-09 | Allied Corporation | Decomposition of cumene oxidation product |
| US4431849A (en) * | 1981-10-21 | 1984-02-14 | The Goodyear Tire & Rubber Company | Process for preparing a methyl phenol |
| JPH0635407B2 (ja) * | 1985-02-21 | 1994-05-11 | 三井石油化学工業株式会社 | ２，６−ジイソプロピルナフタレンの酸化方法 |
| JP2686490B2 (ja) * | 1988-09-05 | 1997-12-08 | 三菱化学株式会社 | クメンヒドロペルオキシドの精製方法 |
| US4950794A (en) | 1989-05-24 | 1990-08-21 | Arco Chemical Technology, Inc. | Ethylbenzene oxidation |
| JP3061394B2 (ja) | 1990-04-02 | 2000-07-10 | 三井化学株式会社 | クメンハイドロパーオキサイドの製造方法 |
| TW226011B (enExample) * | 1991-12-26 | 1994-07-01 | Sumitomo Chemical Co | |
| TW237445B (enExample) * | 1992-07-07 | 1995-01-01 | Sumitomo Chemical Co | |
| US5254751A (en) | 1992-09-14 | 1993-10-19 | General Electric Company | Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone |
| RU2108318C1 (ru) * | 1994-03-01 | 1998-04-10 | Закошанский Владимир Михайлович | СПОСОБ ПОЛУЧЕНИЯ ФЕНОЛА, АЦЕТОНА И α МЕТИЛСТИРОЛА |
| US5767322A (en) * | 1996-06-27 | 1998-06-16 | General Electric Company | Cumene oxidation process |
| JP3391644B2 (ja) * | 1996-12-19 | 2003-03-31 | 住友化学工業株式会社 | ハイドロパーオキシドの抽出方法 |
| US6077977A (en) | 1998-06-01 | 2000-06-20 | General Electric Company | Method for preparing hydroperoxides by oxygenation |
| EP1042264B1 (en) | 1998-09-04 | 2006-03-15 | Illa International L.L.C. | High selective method of phenol and acetone production |
| RU2282621C2 (ru) * | 2000-12-27 | 2006-08-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения органического гидропероксида, содержащего уменьшенное количество примесей |
| US6465695B1 (en) * | 2001-07-27 | 2002-10-15 | General Electric Company | Method and system for manufacturing cumene hydroperoxide |
| US6486365B1 (en) * | 2002-04-04 | 2002-11-26 | General Electric Company | Production and purification of phenol: hydroxyacetone removal by hydrotalcite |
-
2004
- 2004-01-21 US US10/761,641 patent/US7141703B2/en not_active Expired - Fee Related
- 2004-02-11 EP EP04710252A patent/EP1594838A1/en not_active Withdrawn
- 2004-02-11 TW TW093103185A patent/TW200508188A/zh unknown
- 2004-02-11 JP JP2006503496A patent/JP4912870B2/ja not_active Expired - Fee Related
- 2004-02-11 MY MYPI20040415A patent/MY139447A/en unknown
- 2004-02-11 BR BRPI0407404-1A patent/BRPI0407404A/pt not_active IP Right Cessation
- 2004-02-11 KR KR1020057014920A patent/KR20050097550A/ko not_active Ceased
- 2004-02-11 WO PCT/US2004/004010 patent/WO2004074241A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1594838A1 (en) | 2005-11-16 |
| TW200508188A (en) | 2005-03-01 |
| JP2006517968A (ja) | 2006-08-03 |
| MY139447A (en) | 2009-10-30 |
| BRPI0407404A (pt) | 2006-02-21 |
| WO2004074241A1 (en) | 2004-09-02 |
| US7141703B2 (en) | 2006-11-28 |
| US20040162448A1 (en) | 2004-08-19 |
| JP4912870B2 (ja) | 2012-04-11 |
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