JP5746634B2 - 3,7−ジアザ−ビシクロ[3.3.1]ノナン金属錯体の製造方法 - Google Patents
3,7−ジアザ−ビシクロ[3.3.1]ノナン金属錯体の製造方法 Download PDFInfo
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- JP5746634B2 JP5746634B2 JP2011541179A JP2011541179A JP5746634B2 JP 5746634 B2 JP5746634 B2 JP 5746634B2 JP 2011541179 A JP2011541179 A JP 2011541179A JP 2011541179 A JP2011541179 A JP 2011541179A JP 5746634 B2 JP5746634 B2 JP 5746634B2
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- nonane
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- -1 3,7-diaza-bicyclo [3.3.1] nonane metal complex Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002184 metal Substances 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical group Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HIOSLGKLKMELKG-UHFFFAOYSA-N 2-butylheptanedioic acid Chemical compound CCCCC(C(O)=O)CCCCC(O)=O HIOSLGKLKMELKG-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
[MaLkZn]Ym (2)
(式中、Mは、次の金属:Mn(II)−(III)−(IV)、Cu(I)−(II)−(III)、Fe(II)−(III)−(IV)−(V)及びCo(I)−(II)−(III)を示し;
Lは、次式(1)で表される配位子、又はそのプロトン化形又は脱プロトン化形、
Zは、一価、二価又は三価のアニオン、又は中性分子から選択される、金属に一座、二座又は三座で配位できる、配位化合物、例えば、OH−、NO3 −、NO、S2−、RS−、PO4 3−、H2O、CO3 2−、ROH、Cl−、Br−、CN−、ClO4 −、RCOO−、SO4 2−であり;
Yは、錯体の電荷を相殺するアニオンであり;
aは、1〜10、好ましくは1〜4の整数であり;
kは、1〜10の整数であり;
nは、1〜10、好ましくは1〜4の整数であり;
mは、1〜20、好ましくは1〜8の整数である。)
反応容器中に、水を33.6kg(2,000モル)及び2,4ジ−(2−ピリジル)−3−メチル−7−(ピリジン−2−イルメチル)−3,7−ジアザビシクロ[3.3.1]ノナン−9−オン−1,5−ジメチル−ジカルボキシレート(N2Py3o)を20.6kg(40モル)を装填し、そして30分以内で均質な溶液になるまで撹拌した。反応容器を閉じて、窒素を充填した。窒素で不活性化した後、水性の塩化鉄(II)溶液(30.2%濃度)17kg(40.6モル)を30分以内で加え、そしてその滴下漏斗を水5kgで後洗浄した。この反応溶液を室温で5時間撹拌し、その後、好ましくは噴霧乾燥法により乾燥させた。この方法で、鉄(1+),クロロ[ジメチル 9,9−ジヒドロキシ−3−メチル−2,4−ジ(2−ピリジニル−ΚN)−7−[(2−ピリジニル−ΚN)メチル]−3,7−ジアザビシクロ[3.3.1]ノナン−1,5−ジカルボキシレート−ΚN3,Κn7]−,クロリド(1:1)の名称の化合物が得られた。
例1におけるのと同じ3,7−ジアザビシクロ[3.3.1]ノナン化合物64.45g(0.125モル)を粉末化し、そしてこの形態で水107.5g(5.97モル)中に懸濁させた。それから、30.2%濃度の塩化鉄(II)溶液52.28gを加え、そしてその反応混合物を3時間室温で撹拌した。生成物の微細な懸濁物は、ここで、ろ過及び真空乾燥棚中での乾燥によって、粉末状の黄色い最終生成物にした。この方法で、>95%の純度(HPLC)で81gの収量(98%)で、例1におけるのと同じ生成物が得られた。
Claims (7)
- 次式(2)で表される3,7−ジアザ−ビシクロ[3.3.1]ノナン−金属錯体の製造方法、
[MaLkZn]Ym (2)
(式中、
Mは次の金属、Mn(II)−(III)−(IV)、Cu(I)−(II)−(III)、Fe(II)−(III)−(IV)−(V)又はCo(I)−(II)−(III)を示し;
Lは、次式(1)で表される配位子、又はそのプロトン化形又は脱プロトン化形、
Zは、一価、二価又は三価のアニオン、又は中性分子から選択される、金属に一座、二座又は三座で配位できる、配位化合物であり;
Yは、錯体の電荷を相殺するアニオンであり;
aは、1〜10の整数であり;
kは、1〜10の整数であり;
nは、1〜10の整数であり;
mは、1〜20の整数である。)、
であって、該配位子Lを水中に溶解または懸濁し、そして金属塩で錯化することを特徴とする、上記の方法。 - Zが、OH−、NO3 −、NO、S2−、RS−、PO4 3−、H2O、CO3 2−、ROH、Cl−、Br−、CN−、ClO4 −、RCOO− 又はSO4 2− であり、この場合Rは請求項1に定義した通りであることを特徴とする、請求項1に記載の方法。
- aが1〜4の整数であり、nが1〜4の整数であり、そしてmが1〜8の整数であることを特徴とする、請求項1又は2に記載の方法。
- 前記金属塩が、塩化Fe(II)であることを特徴とする、請求項1〜3のいずれか一つに記載の方法。
- 鉄(1+),クロロ[ジメチル9,9−ジヒドロキシ−3−メチル−2,4−ジ(2−ピリジニル−N)−7−[(2−ピリジニル−N)メチル]−3,7−ジアザビシクロ[3.3.1]ノナン−1,5−ジカルボキシレート−N3,N7]−,クロリドが製造されることを特徴とする、請求項1〜4のいずれか一つに記載の方法。
- 前記配位子Lを錯化させるために、前記金属塩を固体としてかあるいは水性の金属塩溶液として、該配位子Lの水性の溶液又は懸濁液に加えることを特徴とする、請求項1〜5のいずれか一つに記載の方法。
- 室温で遂行されることを特徴とする、請求項1〜6のいずれか一つに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008064009.3 | 2008-12-19 | ||
DE102008064009A DE102008064009A1 (de) | 2008-12-19 | 2008-12-19 | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Metall-Komplexen |
PCT/EP2009/008907 WO2010069524A1 (de) | 2008-12-19 | 2009-12-12 | Verfahren zur herstellung von 3,7-diaza-bicyclo[3.3.1]nonan-metall-komplexen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012512210A JP2012512210A (ja) | 2012-05-31 |
JP5746634B2 true JP5746634B2 (ja) | 2015-07-08 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2011541179A Active JP5746634B2 (ja) | 2008-12-19 | 2009-12-12 | 3,7−ジアザ−ビシクロ[3.3.1]ノナン金属錯体の製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8536334B2 (ja) |
EP (1) | EP2380152B1 (ja) |
JP (1) | JP5746634B2 (ja) |
DE (1) | DE102008064009A1 (ja) |
ES (1) | ES2477546T3 (ja) |
WO (1) | WO2010069524A1 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005027619A1 (de) * | 2005-06-15 | 2006-12-28 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
DE102008038376A1 (de) * | 2008-08-19 | 2010-02-25 | Clariant International Ltd. | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
DE102008045207A1 (de) * | 2008-08-30 | 2010-03-04 | Clariant International Limited | Bleichkatalysatormischungen bestehend aus Mangansalzen und Oxalsäure oder deren Salze |
DE102010007058A1 (de) | 2010-02-06 | 2011-08-11 | Clariant International Limited | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Metallkomplex-Lösungen |
DE102010007059A1 (de) * | 2010-02-06 | 2011-08-11 | Clariant International Limited | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Metallkomplexen |
JP5897583B2 (ja) * | 2010-10-11 | 2016-03-30 | ウェイルケム・スウィッツァーランド・アクチエンゲゼルシャフト | 3,7−ジアザ−ビシクロ[3.3.1]ノナン−金属錯体の製造方法 |
DE102010053380B4 (de) | 2010-12-03 | 2019-05-09 | Johannes Kiehl Kg | Pflegemittel für Holzoberflächen, Verfahren zum Ölen von Echtholzflächen und Verwendung bestimmter Eisen Komplexe als Trockenstoff in oxidativ trocknenden Holzpflegemitteln auf Leinölbasis |
JP6117583B2 (ja) * | 2013-03-26 | 2017-04-19 | 株式会社Nttファシリティーズ | 空調システム |
CN103602268B (zh) * | 2013-10-10 | 2015-09-02 | 中钞油墨有限公司 | 环保型催干剂及其油墨组合物 |
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GB1182143A (en) | 1966-03-01 | 1970-02-25 | United States Borax Chem | Bleaching Compositions and Methods. |
US4414127A (en) | 1981-07-06 | 1983-11-08 | Syntex (U.S.A.) Inc. | Contact lens cleaning solutions |
GR76237B (ja) | 1981-08-08 | 1984-08-04 | Procter & Gamble | |
US4481129A (en) | 1981-12-23 | 1984-11-06 | Lever Brothers Company | Bleach compositions |
GB8329762D0 (en) | 1983-11-08 | 1983-12-14 | Unilever Plc | Manganese adjuncts |
GB8405189D0 (en) | 1984-02-28 | 1984-04-04 | Interox Chemicals Ltd | Peroxide activation |
US4728455A (en) | 1986-03-07 | 1988-03-01 | Lever Brothers Company | Detergent bleach compositions, bleaching agents and bleach activators |
AU2614895A (en) | 1994-06-13 | 1996-01-05 | Unilever N.V. | Bleach activation |
DE4443177A1 (de) | 1994-12-05 | 1996-06-13 | Henkel Kgaa | Aktivatormischungen für anorganische Perverbindungen |
US6734155B1 (en) | 1997-07-09 | 2004-05-11 | The Procter & Gamble Company | Cleaning compositions comprising an oxidoreductase |
CA2248476A1 (en) | 1997-10-01 | 1999-04-01 | Unilever Plc | Bleach activation |
DE19909546C1 (de) | 1999-03-04 | 2000-06-29 | Consortium Elektrochem Ind | Mehrkomponentensystem zur enzymkatalysierten Oxidation von Substraten sowie Verfahren zur enzymkatalysierten Oxidation |
WO2000060045A1 (en) * | 1999-04-01 | 2000-10-12 | The Procter & Gamble Company | Transition metal bleaching agents |
GB9930422D0 (en) | 1999-12-22 | 2000-02-16 | Unilever Plc | Bleach catalysts |
GB0030673D0 (en) | 2000-12-15 | 2001-01-31 | Unilever Plc | Ligand and complex for catalytically bleaching a substrate |
GB0104980D0 (en) * | 2001-02-28 | 2001-04-18 | Unilever Plc | Liquid cleaning compositions and their use |
BR0306912A (pt) | 2002-02-28 | 2004-11-09 | Unilever Nv | Composição de branqueamento, e, processo para o branqueamento de uma mancha |
CA2488213A1 (en) | 2002-06-06 | 2003-12-18 | Unilever Plc | Ligand and complex for catalytically bleaching a substrate |
DE10304131A1 (de) | 2003-02-03 | 2004-08-05 | Clariant Gmbh | Verwendung von Übergangsmetallkomplexen als Bleichkatalysatoren |
DE10345273A1 (de) | 2003-09-30 | 2005-04-21 | Clariant Gmbh | Verwendung von Übergangsmetallkomplexen mit Lactamliganden als Bleichkatalysatoren |
GB0411304D0 (en) | 2004-05-21 | 2004-06-23 | Fellows Adrian N | An antimicrobial composition |
DE102005027619A1 (de) | 2005-06-15 | 2006-12-28 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
DE102008038376A1 (de) | 2008-08-19 | 2010-02-25 | Clariant International Ltd. | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
DE102008045215A1 (de) | 2008-08-30 | 2010-03-04 | Clariant International Ltd. | Verwendung von Mangan-Oxalatenn als Bleichkatalysatoren |
DE102008045207A1 (de) | 2008-08-30 | 2010-03-04 | Clariant International Limited | Bleichkatalysatormischungen bestehend aus Mangansalzen und Oxalsäure oder deren Salze |
-
2008
- 2008-12-19 DE DE102008064009A patent/DE102008064009A1/de not_active Withdrawn
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2009
- 2009-12-12 WO PCT/EP2009/008907 patent/WO2010069524A1/de active Application Filing
- 2009-12-12 ES ES09774843.8T patent/ES2477546T3/es active Active
- 2009-12-12 JP JP2011541179A patent/JP5746634B2/ja active Active
- 2009-12-12 US US13/140,589 patent/US8536334B2/en active Active
- 2009-12-12 EP EP09774843.8A patent/EP2380152B1/de active Active
Also Published As
Publication number | Publication date |
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EP2380152B1 (de) | 2014-04-16 |
ES2477546T3 (es) | 2014-07-17 |
EP2380152A1 (de) | 2011-10-26 |
US20110263857A1 (en) | 2011-10-27 |
US8536334B2 (en) | 2013-09-17 |
WO2010069524A1 (de) | 2010-06-24 |
DE102008064009A1 (de) | 2010-06-24 |
JP2012512210A (ja) | 2012-05-31 |
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