JP2005527531A5 - - Google Patents
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- Publication number
- JP2005527531A5 JP2005527531A5 JP2003576556A JP2003576556A JP2005527531A5 JP 2005527531 A5 JP2005527531 A5 JP 2005527531A5 JP 2003576556 A JP2003576556 A JP 2003576556A JP 2003576556 A JP2003576556 A JP 2003576556A JP 2005527531 A5 JP2005527531 A5 JP 2005527531A5
- Authority
- JP
- Japan
- Prior art keywords
- mol
- cyanomethyl
- synthesis
- yield
- stirred
- 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.)
- Pending
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- -1 cyanomethyl Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PTMNLAPQVWUAFM-UHFFFAOYSA-N 2-(dihexylamino)acetonitrile Chemical compound CCCCCCN(CC#N)CCCCCC PTMNLAPQVWUAFM-UHFFFAOYSA-N 0.000 description 4
- LRPJNWSVHROUBK-UHFFFAOYSA-N 2-(dioctylamino)acetonitrile Chemical compound CCCCCCCCN(CC#N)CCCCCCCC LRPJNWSVHROUBK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VIRVEVLKEQMVBV-UHFFFAOYSA-M benzenesulfonate;cyanomethyl-dihexyl-methylazanium Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1.CCCCCC[N+](C)(CC#N)CCCCCC VIRVEVLKEQMVBV-UHFFFAOYSA-M 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- AXBLTSBRRWKMHE-UHFFFAOYSA-M cyanomethyl-dihexyl-methylazanium;chloride Chemical compound [Cl-].CCCCCC[N+](C)(CC#N)CCCCCC AXBLTSBRRWKMHE-UHFFFAOYSA-M 0.000 description 2
- YAQZZWFGTXBDAD-UHFFFAOYSA-M cyanomethyl-methyl-dioctylazanium;2-propan-2-ylbenzenesulfonate Chemical compound CC(C)C1=CC=CC=C1S([O-])(=O)=O.CCCCCCCC[N+](C)(CC#N)CCCCCCCC YAQZZWFGTXBDAD-UHFFFAOYSA-M 0.000 description 2
- FPJCWZGEZJXYKL-UHFFFAOYSA-M cyanomethyl-methyl-dioctylazanium;phenylmethanesulfonate Chemical compound [O-]S(=O)(=O)CC1=CC=CC=C1.CCCCCCCC[N+](C)(CC#N)CCCCCCCC FPJCWZGEZJXYKL-UHFFFAOYSA-M 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- COHOXCGHYWNNFN-UHFFFAOYSA-N methyl 2-propan-2-ylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1C(C)C COHOXCGHYWNNFN-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- BAYSWZWSDIQWSM-UHFFFAOYSA-N cyanomethyl-dihexyl-methylazanium Chemical compound CCCCCC[N+](C)(CC#N)CCCCCC BAYSWZWSDIQWSM-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- POMGZMHIXYRARC-UHFFFAOYSA-N n-hexyl-n-methylhexan-1-amine Chemical compound CCCCCCN(C)CCCCCC POMGZMHIXYRARC-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940079842 sodium cumenesulfonate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- QEKATQBVVAZOAY-UHFFFAOYSA-M sodium;4-propan-2-ylbenzenesulfonate Chemical compound [Na+].CC(C)C1=CC=C(S([O-])(=O)=O)C=C1 QEKATQBVVAZOAY-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10211389A DE10211389A1 (de) | 2002-03-15 | 2002-03-15 | Ammoniumnitrile und deren Verwendung als hydrophobe Bleichaktivatoren |
| PCT/EP2003/002543 WO2003078561A1 (de) | 2002-03-15 | 2003-03-12 | Ammoniumnitrile und deren verwendung als hydrophobe bleichaktivatoren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005527531A JP2005527531A (ja) | 2005-09-15 |
| JP2005527531A5 true JP2005527531A5 (enExample) | 2006-04-20 |
Family
ID=27771315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003576556A Pending JP2005527531A (ja) | 2002-03-15 | 2003-03-12 | アンモニウムニトリル及び疎水性漂白活性化剤としてそれを使用する方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7015185B2 (enExample) |
| EP (1) | EP1487955B1 (enExample) |
| JP (1) | JP2005527531A (enExample) |
| KR (1) | KR20050002804A (enExample) |
| AU (1) | AU2003219043B2 (enExample) |
| BR (1) | BR0305214A (enExample) |
| CA (1) | CA2456927A1 (enExample) |
| DE (2) | DE10211389A1 (enExample) |
| ES (1) | ES2303895T3 (enExample) |
| WO (1) | WO2003078561A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004028494A1 (de) * | 2004-06-11 | 2005-12-29 | Clariant Gmbh | Mischungen von Ammoniumnitril-Bleichaktivatoren und Aminosäuren |
| DE102005005016A1 (de) | 2005-02-03 | 2006-08-10 | Basf Ag | Polymere hydrophobe Aminonitrilquats zur Bleichaktivierung |
| DE102005009137A1 (de) * | 2005-03-01 | 2006-09-07 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von bifunktionellen Ammoniumnitrilen |
| DE102005009136A1 (de) * | 2005-03-01 | 2006-09-07 | Clariant Produkte (Deutschland) Gmbh | Verbessertes Verfahren zur Herstellung von bifunktionellen Ammoniumnitrilen |
| JP2007172716A (ja) * | 2005-12-20 | 2007-07-05 | Sony Corp | 再生装置、再生方法および再生プログラム、記録媒体およびデータ構造、ならびに、オーサリング装置、オーサリング方法およびオーサリングプログラム |
| WO2007111899A2 (en) * | 2006-03-22 | 2007-10-04 | The Procter & Gamble Company | Liquid treatment composition |
| DE102006013665A1 (de) * | 2006-03-24 | 2007-09-27 | Clariant International Limited | Verbessertes Verfahren zur Herstellung von natriumchloridfreien Ammoniumnitrilen |
| DE102006013666A1 (de) * | 2006-03-24 | 2007-09-27 | Clariant International Limited | Verbessertes Verfahren zur Herstellung von natriumchloridfreien Ammoniumnitrilen |
| DE102006028032A1 (de) * | 2006-06-14 | 2007-12-20 | Henkel Kgaa | Aufhell- und/oder Färbemittel mit Nitrilen |
| WO2009020767A1 (en) * | 2007-08-07 | 2009-02-12 | Arkema Inc. | Hard surface cleaner containing polysulfonic acid |
| US8124793B2 (en) * | 2007-11-27 | 2012-02-28 | Gail Marie Cronyn, legal representative | Derivatives of ethylene methanedisulfonate as cancer chemotherapeutic agents |
| EP2417237A1 (en) * | 2009-04-10 | 2012-02-15 | Danisco US Inc. | Cellulase-containing dish detergents |
| CN115494184B (zh) * | 2022-05-09 | 2023-07-28 | 浙江海正药业股份有限公司 | 一种同时检测药物中异丙苯磺酸甲酯、异丙苯磺酸乙酯的方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1382594A (en) | 1971-06-04 | 1975-02-05 | Unilever Ltd | Quaternary ammonium compounds for use in bleaching systems |
| US4144226A (en) * | 1977-08-22 | 1979-03-13 | Monsanto Company | Polymeric acetal carboxylates |
| US4146495A (en) * | 1977-08-22 | 1979-03-27 | Monsanto Company | Detergent compositions comprising polyacetal carboxylates |
| US4751015A (en) * | 1987-03-17 | 1988-06-14 | Lever Brothers Company | Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions |
| US4933103A (en) * | 1987-03-23 | 1990-06-12 | Kao Corporation | Bleaching composition |
| US4915863A (en) * | 1987-08-14 | 1990-04-10 | Kao Corporation | Bleaching composition |
| GB9011618D0 (en) * | 1990-05-24 | 1990-07-11 | Unilever Plc | Bleaching composition |
| GB9012001D0 (en) * | 1990-05-30 | 1990-07-18 | Unilever Plc | Bleaching composition |
| DE4041752A1 (de) | 1990-12-24 | 1992-06-25 | Henkel Kgaa | Enzymzubereitung fuer wasch- und reinigungsmittel |
| DE4216774A1 (de) * | 1992-05-21 | 1993-11-25 | Henkel Kgaa | Verfahren zur kontinuierlichen Herstellung eines granularen Wasch und/oder Reinigungsmittels |
| DE4310506A1 (de) | 1993-03-31 | 1994-10-06 | Cognis Bio Umwelt | Enzymzubereitung für Wasch- und Reinigungsmittel |
| US6313081B1 (en) * | 1995-04-28 | 2001-11-06 | Henkel Kommanditgesellschaft Auf Aktien (Kgaa) | Detergents comprising cellulases |
| US5856165A (en) * | 1995-04-28 | 1999-01-05 | Genencor International | Alkaline cellulase and method of producing same |
| DE19605526A1 (de) | 1996-02-15 | 1997-08-21 | Hoechst Ag | Ammoniumnitrile und deren Verwendung als Bleichaktivatoren |
| DE19649375A1 (de) * | 1996-11-29 | 1998-06-04 | Henkel Kgaa | Acetonitril-Derivate als Bleichaktivatoren in Reinigungsmitteln |
| DE19649384A1 (de) * | 1996-11-29 | 1998-06-04 | Basf Ag | Textilwaschmittel-Formulierung auf Basis von quaternierten Glycinnitrilen, Bleichmitteln, nichtionischen und/oder anionischen Tensiden und Calcium- und/oder Magnesiumionen sequestierenden Verbindungen |
| WO2000036061A2 (de) * | 1998-12-15 | 2000-06-22 | Henkel Kommanditgesellschaft Auf Aktien | Teilchenförmig konfektionierte acetonitril-derivate als bleichaktivatoren in festen reinigungsmitteln |
| DE19908069A1 (de) * | 1999-02-25 | 2000-08-31 | Henkel Kgaa | Compoundierte Acetonitril-Derivate als Bleichaktivatoren in Reinigungsmitteln |
| US20010046951A1 (en) * | 2000-02-02 | 2001-11-29 | Kao Corporation | Bleaching detergent composition |
-
2002
- 2002-03-15 DE DE10211389A patent/DE10211389A1/de not_active Withdrawn
-
2003
- 2003-03-12 KR KR10-2004-7003126A patent/KR20050002804A/ko not_active Ceased
- 2003-03-12 AU AU2003219043A patent/AU2003219043B2/en not_active Ceased
- 2003-03-12 DE DE50309882T patent/DE50309882D1/de not_active Expired - Fee Related
- 2003-03-12 BR BR0305214-1A patent/BR0305214A/pt not_active IP Right Cessation
- 2003-03-12 JP JP2003576556A patent/JP2005527531A/ja active Pending
- 2003-03-12 CA CA002456927A patent/CA2456927A1/en not_active Abandoned
- 2003-03-12 EP EP03714809A patent/EP1487955B1/de not_active Expired - Lifetime
- 2003-03-12 ES ES03714809T patent/ES2303895T3/es not_active Expired - Lifetime
- 2003-03-12 US US10/486,939 patent/US7015185B2/en not_active Expired - Fee Related
- 2003-03-12 WO PCT/EP2003/002543 patent/WO2003078561A1/de not_active Ceased
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