JP5542655B2 - パラジウム(0)−ジベンジリデンアセトン錯体 - Google Patents
パラジウム(0)−ジベンジリデンアセトン錯体 Download PDFInfo
- Publication number
- JP5542655B2 JP5542655B2 JP2010503380A JP2010503380A JP5542655B2 JP 5542655 B2 JP5542655 B2 JP 5542655B2 JP 2010503380 A JP2010503380 A JP 2010503380A JP 2010503380 A JP2010503380 A JP 2010503380A JP 5542655 B2 JP5542655 B2 JP 5542655B2
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- dibenzylideneacetone
- dba
- complex
- product
- 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.)
- Active
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims description 93
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003849 aromatic solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 101150003085 Pdcl gene Proteins 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- -1 PdCl 2 Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method 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
-
- 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Description
1.)Inorganic Synthesis, 28, 110 (1990)による合成
合成を不活性ガス下に実施する。PdCl2 2.096g(11.73mmol)及びNaCl 0.686g(11.73mmol)をアルゴン下に装入し、メタノール59mlと混合する。
外観:暗褐色の固体。
生成物1.00gをクロロホルム150ml中に溶解させ、室温で30分撹拌する。この溶液をメンブレンフィルターを通して吸引する。水30ml及びアセトン30mlで、前記フィルターを後洗浄し、引き続き一晩にわたって45℃で真空下に乾燥させる。残留物は1.4%である。
m(生成物):6.4g
Pdを基準とした収率:94%
CHCl3に不溶の成分:1.4%
合成を不活性ガス下に実施する。
ジベンジリデンアセトン1.55kg(6616mmol)、Na2PdCl4 657.9g(2208mmol)及びメタノール56lを、反応フラスコ中で57℃に加熱する。ついで、酢酸ナトリウム1.47kg(17920mmol)の添加を行う。嵩張った帯赤色の固体が沈殿する。
外観:暗褐色の固体。
生成物1.00gをクロロホルム150ml中に溶解させ、室温で30分撹拌した。この溶液をメンブレンフィルターを通して吸引した。水30ml及びアセトン30mlで、前記フィルターを後洗浄し、引き続き一晩にわたって45℃で真空下に乾燥させた。残留物は1.1%である。
m(生成物):1053g
Pdを基準とした収率:93%
CHCl3に不溶の成分:1.1質量%
合成を不活性ガス下に実施した。メタノール300mlを、アルゴン下に反応フラスコ中に装入し、57℃に加熱した。ついで、ジベンジリデンアセトン8.245g(35.2mmol)及びNa2[PdCl4] 3.495g(Pd 1.248g、Pd 11.7mmol)をアルゴンフロー下にそれに添加した。
外観:帯赤褐色の固体。
生成物1.00gをクロロホルム150ml中に溶解させ、室温で30分撹拌した。この溶液をメンブレンフィルターを通して吸引した。水30ml及びアセトン30mlで、前記フィルターを後洗浄し、引き続き前記フィルターを一晩にわたって45℃で真空下に乾燥させた。残留物は0%であった。
m(生成物):6.4g
Pdを基準とした収率:95.4%
CHCl3に不溶の成分:0%
合成を実験1のように実施したが、しかしながら反応を50℃の開始温度で実施した。
m(生成物):7.05g
Pdを基準とした収率:92.4%
CHCl3に不溶の成分:0.2%
合成を実験1のように実施したが、しかしながら四倍のバッチサイズを選択した。反応を60℃の開始温度で実施した。
m(生成物):24.682g
Pdを基準とした収率:96.4%
CHCl3に不溶の成分:0.2%
合成を実験3のように実施した。反応を60℃の開始温度で実施した。
m(生成物):25.0g
Pdを基準とした収率:96.2%
CHCl3に不溶の成分:0%
合成を実験1のように実施したが、しかしながら、反応を60℃の開始温度で実施し、前記温度を5分間維持し;その後はじめて冷却した。
m(生成物):6.15g
Pdを基準とした収率:99.5%
CHCl3に不溶の成分:0.1%
Claims (11)
- パラジウム(0)−ジベンジリデンアセトン錯体Pdx(dba)y[ここでy/xは1.5〜3である]であって、
該錯体は、塩素化炭化水素に不溶の含分を基準として、少なくとも99.5質量%の純度であり、かつ
該錯体は、当該錯体に付加された芳香族溶剤又は塩素含有炭化水素を実質的に不含であること
を特徴とする、パラジウム(0)−ジベンジリデンアセトン錯体Pdx(dba)y。 - 該錯体が、塩素化炭化水素に不溶の含分を基準として、少なくとも99.9質量%の純度である、請求項1記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- 1質量‰未満のハロゲン化炭化水素を含有する、請求項1又は2記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- 100ppm未満のハロゲン化炭化水素を含有する、請求項3記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- 10ppm未満のハロゲン化炭化水素を含有する、請求項4記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- パラジウム対ジベンジリデンアセトンのモル比が1:1.5〜1:1.8の範囲内である、請求項1から5までのいずれか1項記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- パラジウム対ジベンジリデンアセトンのモル比が1:1.8〜1:2.2の範囲内である、請求項1から5までのいずれか1項記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- パラジウム対ジベンジリデンアセトンのモル比が1:1.9〜1:2.1の範囲内である、請求項7記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- パラジウム対ジベンジリデンアセトンのモル比が1:2.5〜1:3の範囲内である、請求項1から5までのいずれか1項記載のパラジウム(0)−ジベンジリデンアセトン錯体。
- 請求項1から9までのいずれか1項記載のPdx(dba)y錯体の、元素分析を用いてその化学量論を決定するための、使用。
- アルコール中でPd塩及びジベンジリデンアセトン(dba)からPdx(dba)y錯体[ここでy/xは1.5〜3である]を製造する方法において、
まず最初にdbaをアルコール中で40℃を上回る温度に予熱し、かつ
その後にPd塩を予熱した溶液に添加し、それに続き前記錯体を塩基で沈殿させること
を特徴とする、方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102007018703.5 | 2007-04-18 | ||
DE102007018703A DE102007018703A1 (de) | 2007-04-18 | 2007-04-18 | Palladium(0)-Dibenzylidenaceton-Komplexe |
PCT/EP2008/002785 WO2008128644A1 (de) | 2007-04-18 | 2008-04-09 | Palladium(0)-dibenzylidenaceton-komplexe |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010524870A JP2010524870A (ja) | 2010-07-22 |
JP5542655B2 true JP5542655B2 (ja) | 2014-07-09 |
Family
ID=39544989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010503380A Active JP5542655B2 (ja) | 2007-04-18 | 2008-04-09 | パラジウム(0)−ジベンジリデンアセトン錯体 |
Country Status (12)
Country | Link |
---|---|
US (1) | US7999126B2 (ja) |
EP (1) | EP2134733B1 (ja) |
JP (1) | JP5542655B2 (ja) |
KR (1) | KR101464015B1 (ja) |
CN (1) | CN101663311A (ja) |
BR (1) | BRPI0810450A8 (ja) |
DE (1) | DE102007018703A1 (ja) |
DK (1) | DK2134733T3 (ja) |
RU (1) | RU2470029C2 (ja) |
SA (1) | SA08290234B1 (ja) |
WO (1) | WO2008128644A1 (ja) |
ZA (1) | ZA200907200B (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011101665A1 (en) | 2010-02-16 | 2011-08-25 | Johnson Matthey Plc | Process |
CN102010445B (zh) * | 2010-11-30 | 2013-06-12 | 金川集团有限公司 | 一种双(二亚苄基丙酮)钯(0)的制备方法 |
RU2645680C1 (ru) * | 2016-12-28 | 2018-02-27 | Федеральное государственное унитарное предприятие "Институт химических реактивов и особо чистых химических веществ Национального исследовательского центра "Курчатовский институт" (НИЦ "Курчатовский институт"- ИРЕА) | Дихлорид ди(фенилацетонитрил) палладия и способ его получения |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4347232A (en) * | 1981-06-17 | 1982-08-31 | Fmc Corporation | Preparation of hydrogen peroxide from its elements |
DE10105751B4 (de) * | 2001-02-08 | 2005-09-29 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Octen |
AU2003296175A1 (en) * | 2002-12-24 | 2004-07-22 | The Honjo Chemical Corporation | Organic platinum-group element compound of fullerenol and/or fullerenol hydrogen sulfate ester, utilization of the same, and process for producing the same |
JP2004217626A (ja) * | 2002-12-24 | 2004-08-05 | Honjo Chemical Corp | フラレノール及び/又はフラレノール硫酸水素エステルの有機白金族元素化合物とその利用とその製造方法 |
-
2007
- 2007-04-18 DE DE102007018703A patent/DE102007018703A1/de not_active Withdrawn
-
2008
- 2008-04-09 DK DK08735101.1T patent/DK2134733T3/da active
- 2008-04-09 US US12/595,628 patent/US7999126B2/en active Active
- 2008-04-09 KR KR1020097019880A patent/KR101464015B1/ko active IP Right Grant
- 2008-04-09 JP JP2010503380A patent/JP5542655B2/ja active Active
- 2008-04-09 EP EP08735101.1A patent/EP2134733B1/de not_active Revoked
- 2008-04-09 RU RU2009142427/04A patent/RU2470029C2/ru active
- 2008-04-09 CN CN200880012529A patent/CN101663311A/zh active Pending
- 2008-04-09 WO PCT/EP2008/002785 patent/WO2008128644A1/de active Application Filing
- 2008-04-09 BR BRPI0810450A patent/BRPI0810450A8/pt not_active Application Discontinuation
- 2008-04-16 SA SA08290234A patent/SA08290234B1/ar unknown
-
2009
- 2009-10-15 ZA ZA2009/07200A patent/ZA200907200B/en unknown
Also Published As
Publication number | Publication date |
---|---|
BRPI0810450A8 (pt) | 2015-12-01 |
CN101663311A (zh) | 2010-03-03 |
KR20100014549A (ko) | 2010-02-10 |
RU2470029C2 (ru) | 2012-12-20 |
BRPI0810450A2 (pt) | 2014-10-14 |
EP2134733A1 (de) | 2009-12-23 |
JP2010524870A (ja) | 2010-07-22 |
SA08290234B1 (ar) | 2012-02-12 |
EP2134733B1 (de) | 2013-07-17 |
ZA200907200B (en) | 2010-11-24 |
US20100167408A1 (en) | 2010-07-01 |
DK2134733T3 (da) | 2013-10-14 |
WO2008128644A1 (de) | 2008-10-30 |
KR101464015B1 (ko) | 2014-11-20 |
RU2009142427A (ru) | 2011-05-27 |
US7999126B2 (en) | 2011-08-16 |
DE102007018703A1 (de) | 2008-10-23 |
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