UA68409C2 - Method of producing organic disulfides - Google Patents
Method of producing organic disulfides Download PDFInfo
- Publication number
- UA68409C2 UA68409C2 UA2001064424A UA2001064424A UA68409C2 UA 68409 C2 UA68409 C2 UA 68409C2 UA 2001064424 A UA2001064424 A UA 2001064424A UA 2001064424 A UA2001064424 A UA 2001064424A UA 68409 C2 UA68409 C2 UA 68409C2
- Authority
- UA
- Ukraine
- Prior art keywords
- organic
- stage
- amine
- disulfide
- mercaptan
- Prior art date
Links
- 150000008427 organic disulfides Chemical class 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 35
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 33
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000011593 sulfur Substances 0.000 claims abstract description 28
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 28
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 21
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 15
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical group CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 24
- 239000012071 phase Substances 0.000 claims description 19
- 238000009835 boiling Methods 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 16
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 230000003993 interaction Effects 0.000 claims description 8
- 229920001021 polysulfide Polymers 0.000 claims description 8
- 239000005077 polysulfide Substances 0.000 claims description 8
- 150000008117 polysulfides Polymers 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000005191 phase separation Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 4
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000012876 topography Methods 0.000 claims 1
- -1 alkane sulfonic acids Chemical class 0.000 abstract description 4
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 16
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- YWHLKYXPLRWGSE-UHFFFAOYSA-N Dimethyl trisulfide Chemical compound CSSSC YWHLKYXPLRWGSE-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000008116 organic polysulfides Chemical class 0.000 description 4
- 239000005373 porous glass Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002019 disulfides Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 2
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical class SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical class C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical class CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19854427A DE19854427A1 (de) | 1998-11-25 | 1998-11-25 | Verfahren zur Herstellung von organischen Disulfiden |
| PCT/EP1999/009145 WO2000031029A1 (de) | 1998-11-25 | 1999-11-25 | Verfahren zur herstellung von organischen disulfiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA68409C2 true UA68409C2 (en) | 2004-08-16 |
Family
ID=7889012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001064424A UA68409C2 (en) | 1998-11-25 | 1999-11-25 | Method of producing organic disulfides |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6686506B1 (ja) |
| EP (1) | EP1133472B1 (ja) |
| JP (1) | JP4460780B2 (ja) |
| KR (1) | KR100626185B1 (ja) |
| CN (1) | CN1188393C (ja) |
| AT (1) | ATE289591T1 (ja) |
| AU (1) | AU765463B2 (ja) |
| BR (1) | BR0102243A (ja) |
| CA (1) | CA2352385C (ja) |
| DE (2) | DE19854427A1 (ja) |
| ES (1) | ES2237958T3 (ja) |
| HU (1) | HUP0201439A2 (ja) |
| ID (1) | ID29243A (ja) |
| IN (1) | IN2001CH00727A (ja) |
| MX (1) | MXPA01005200A (ja) |
| PL (1) | PL196872B1 (ja) |
| SK (1) | SK7262001A3 (ja) |
| UA (1) | UA68409C2 (ja) |
| WO (1) | WO2000031029A1 (ja) |
| ZA (1) | ZA200104296B (ja) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10116817A1 (de) * | 2001-04-04 | 2002-10-17 | Basf Ag | Verfahren zur Herstellung eines organischen Disulfids |
| DE10323839B3 (de) * | 2003-05-23 | 2004-10-21 | Thioplast Chemicals Gmbh & Co.Kg | Oxidation von Mercaptoethanol |
| EP1994126A4 (en) * | 2006-02-01 | 2011-08-24 | Fluor Tech Corp | CONFIGURATIONS AND METHODS FOR REMOVING MERCAPTANS FROM GAS SUPPLY |
| CN100349961C (zh) * | 2006-06-22 | 2007-11-21 | 广州大学 | 一种聚双苯胺基二硫化物及其制备方法 |
| JP5414529B2 (ja) * | 2006-11-11 | 2014-02-12 | エコスプレイ リミテッド | ニンニクの処理 |
| MX2011006728A (es) * | 2008-12-23 | 2011-07-13 | Basf Se | Metodo para comprimir gases que contienen sulfuro de hidrogeno. |
| CN101475517B (zh) * | 2009-01-15 | 2012-08-15 | 河南大学 | 一种对称的含二硫键化合物的制备方法 |
| FR3023287B1 (fr) * | 2014-07-04 | 2016-07-22 | Arkema France | Procede de preparation de methylmercaptan |
| FR3023288B1 (fr) * | 2014-07-04 | 2016-07-15 | Arkema France | Procede de preparation de disulfure de dimethyle |
| CN104592071B (zh) * | 2015-01-13 | 2016-12-07 | 湖北兴发化工集团股份有限公司 | 一种二甲基二硫生产过程溶解状态硫磺加入方法 |
| CN104557642B (zh) * | 2015-01-19 | 2017-02-01 | 湖北兴发化工集团股份有限公司 | 一种利用超声波促进二甲基二硫生产的方法及装置 |
| WO2017018095A1 (ja) * | 2015-07-24 | 2017-02-02 | 味の素株式会社 | フレーバー組成物 |
| JP6200124B1 (ja) * | 2016-03-18 | 2017-09-20 | 三井化学株式会社 | （ポリ）スルフィド化合物の製造方法およびエピスルフィド化合物の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820062A (en) | 1954-08-11 | 1958-01-14 | Pure Oil Co | Preparation of organic thiols |
| FR1358398A (fr) | 1962-11-20 | 1964-04-17 | Aquitaine Petrole | Fabrication de disulfures organiques |
| DE1250430B (ja) * | 1963-05-20 | |||
| US3314999A (en) * | 1963-11-15 | 1967-04-18 | Aquitaine Petrole | Process for the preparation of organic disulphides |
| US3277180A (en) * | 1964-01-15 | 1966-10-04 | Aquitaine Petrole | Process for the manufacture of organic disulphides |
| DE3572657D1 (en) | 1985-04-26 | 1989-10-05 | Pennwalt Corp | Preparation of dialkyl disulfides |
| DE3676344D1 (de) | 1985-05-13 | 1991-02-07 | Atochem North America | Verfahren zur herstellung von dialkyldisulfiden. |
| US5026915A (en) * | 1985-05-13 | 1991-06-25 | Atochem North America, Inc. | Process for the manufacture of dialkyl disulfides |
| US5202494A (en) | 1990-05-31 | 1993-04-13 | Phillips Petroleum Company | Continuous process for the production of disulfides |
| US5659086A (en) * | 1995-06-06 | 1997-08-19 | Phillips Petroleum Company | Production of organic disulfides |
| FR2742144B1 (fr) * | 1995-12-11 | 1998-01-16 | Elf Aquitaine | Procede de preparation de disulfures et de polysulfures organiques en presence de resines polystyrene-divinylbenzene possedant des groupes amine primaire |
| AU5714698A (en) * | 1997-02-10 | 1998-08-26 | Innochem Inc. | Preparation of alkane sulfonic acids and sulfonyl chlorides by oxidation of alkanethiols and dialkyl disulfides |
| FR2773799B1 (fr) * | 1998-01-22 | 2000-02-18 | Elf Aquitaine Exploration Prod | Synthese de disulfures et polysulfures organiques |
-
1998
- 1998-11-25 DE DE19854427A patent/DE19854427A1/de not_active Withdrawn
-
1999
- 1999-11-25 WO PCT/EP1999/009145 patent/WO2000031029A1/de active IP Right Grant
- 1999-11-25 EP EP99961004A patent/EP1133472B1/de not_active Expired - Lifetime
- 1999-11-25 US US09/831,914 patent/US6686506B1/en not_active Expired - Lifetime
- 1999-11-25 UA UA2001064424A patent/UA68409C2/uk unknown
- 1999-11-25 DE DE59911664T patent/DE59911664D1/de not_active Expired - Lifetime
- 1999-11-25 PL PL348774A patent/PL196872B1/pl unknown
- 1999-11-25 CN CNB998157546A patent/CN1188393C/zh not_active Expired - Lifetime
- 1999-11-25 MX MXPA01005200 patent/MXPA01005200A/es active IP Right Grant
- 1999-11-25 AU AU17772/00A patent/AU765463B2/en not_active Ceased
- 1999-11-25 CA CA002352385A patent/CA2352385C/en not_active Expired - Fee Related
- 1999-11-25 HU HU0201439A patent/HUP0201439A2/hu unknown
- 1999-11-25 SK SK726-2001A patent/SK7262001A3/sk unknown
- 1999-11-25 JP JP2000583857A patent/JP4460780B2/ja not_active Expired - Fee Related
- 1999-11-25 ES ES99961004T patent/ES2237958T3/es not_active Expired - Lifetime
- 1999-11-25 ID IDW00200101393A patent/ID29243A/id unknown
- 1999-11-25 KR KR1020017006583A patent/KR100626185B1/ko active IP Right Grant
- 1999-11-25 AT AT99961004T patent/ATE289591T1/de active
-
2001
- 2001-05-25 ZA ZA200104296A patent/ZA200104296B/xx unknown
- 2001-05-25 IN IN727CH2001 patent/IN2001CH00727A/en unknown
- 2001-05-31 BR BR0102243-1A patent/BR0102243A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA01005200A (es) | 2002-01-01 |
| WO2000031029A1 (de) | 2000-06-02 |
| SK7262001A3 (en) | 2002-01-07 |
| AU1777200A (en) | 2000-06-13 |
| ES2237958T3 (es) | 2005-08-01 |
| KR100626185B1 (ko) | 2006-09-20 |
| CN1188393C (zh) | 2005-02-09 |
| CA2352385A1 (en) | 2000-06-02 |
| BR0102243A (pt) | 2003-02-18 |
| US6686506B1 (en) | 2004-02-03 |
| JP4460780B2 (ja) | 2010-05-12 |
| AU765463B2 (en) | 2003-09-18 |
| EP1133472B1 (de) | 2005-02-23 |
| KR20010080584A (ko) | 2001-08-22 |
| HUP0201439A2 (en) | 2002-08-28 |
| ZA200104296B (en) | 2002-09-25 |
| CN1333749A (zh) | 2002-01-30 |
| IN201881B (ja) | 2007-02-23 |
| MX230560B (ja) | 2005-09-13 |
| ATE289591T1 (de) | 2005-03-15 |
| EP1133472A1 (de) | 2001-09-19 |
| DE59911664D1 (de) | 2005-03-31 |
| DE19854427A1 (de) | 2000-05-31 |
| JP2002530371A (ja) | 2002-09-17 |
| ID29243A (id) | 2001-08-16 |
| PL196872B1 (pl) | 2008-02-29 |
| PL348774A1 (en) | 2002-06-17 |
| IN2001CH00727A (en) | 2005-09-16 |
| CA2352385C (en) | 2008-01-22 |
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