JP5165204B2 - パラジウム微粒子の製造方法 - Google Patents
パラジウム微粒子の製造方法 Download PDFInfo
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- JP5165204B2 JP5165204B2 JP2006064813A JP2006064813A JP5165204B2 JP 5165204 B2 JP5165204 B2 JP 5165204B2 JP 2006064813 A JP2006064813 A JP 2006064813A JP 2006064813 A JP2006064813 A JP 2006064813A JP 5165204 B2 JP5165204 B2 JP 5165204B2
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- Prior art keywords
- palladium
- tetrahedral
- catalyst
- fine particles
- reaction
- Prior art date
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims description 251
- 229910052763 palladium Inorganic materials 0.000 title claims description 121
- 239000010419 fine particle Substances 0.000 title claims description 65
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- 239000002245 particle Substances 0.000 claims description 75
- 239000002904 solvent Substances 0.000 claims description 16
- 239000003446 ligand Substances 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
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- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000012456 homogeneous solution Substances 0.000 claims description 4
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- 239000003054 catalyst Substances 0.000 description 95
- 239000000084 colloidal system Substances 0.000 description 62
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 54
- 229910052751 metal Inorganic materials 0.000 description 35
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
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Images
Classifications
-
- B01J35/393—
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
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Description
非特許文献4、5の方法に従って、以下のとおりパラジウム4核錯体(PCA)を製造した。0.40gの酢酸パラジウムPd(OAc)2(エヌ・イー ケムキャット製)を酢酸40mlに溶解させ、一酸化炭素流通下50℃にて2時間攪拌して4核のパラジウム錯体PCA0.24gを黄色結晶として得た。
安息香酸2.2gをトルエン20mlに溶解して得た溶液に上記PCA錯体0.36gを添加し、アルゴン流通下45℃で2時間攪拌し、生成した結晶をトルエンで洗浄後真空乾燥して黄褐色のPCB錯体0.12gを得た。
上記4核パラジウム錯体PCA0.020gをN,N-ジメチルアセトアミド(DMA)1mlに添加し空気中25℃で攪拌した。最初の黄色溶液は1〜2分後に薄い褐色に変わり、5分後には均一な暗褐色コロイドPCA(DMA)5min を得た。このコロイドをカーボングリッドに滴下し乾燥後TEM(Hitachi H800, 加速電圧200kV)およびHR-TEM(Hitachi H9000, 加速電圧300kV)で観察すると、形状の比較的良く揃った三角形のナノ粒子が良く分散した状態で観察され、その他の形状の粒子は非常に少なかった。代表的な視野の中の150個の粒子に関して形状と粒子径(三角形の場合は1辺、球の場合は直径、その他異形の粒子の場合は幾何学的代表径、即ち、面積円相当径)とをリストアップし、形状を三角形、その他の多角形乃至球形、凝集物、形状判別不能の無定形粒子とに分類し、全粒子数で除して、各形状分布を求め、また数平均粒子径を求めた。その結果、三角形75%、その他の多角形乃至球形17%、凝集物2%、無定形6%であった。この結果から、四面体の形状選択性を75%と見積もられた。粒子径は平均6.0nmで、そのばらつき3σは0.7nmであった。
実施例1において、空気中での攪拌を5分で止めないで、延長して70分まで攪拌保持した以外は実施例1と同様に処理して、暗褐色コロイドPCA(DMA)70min を得た。これのTEM観察から、実施例1と同様に図形解析して、四面体の形状選択性は70%と見積もられた。粒子径は平均径15nmで、ばらつき3σは2.5nmであった。
実施例2において、溶媒DMAの代わりに、N,N-ジメチルフォルムアミド(DMF)を用いた以外は実施例2と同様に処理して、四面体パラジウムコロイドPCA(DMF)70min を得た。TEM像から、四面体形状選択性は78%と計算された。粒子径は平均10nmで、ばらつき3σは1.5nmであった。
実施例1において、PCA0.020gの代わりにPCB0.030gを用いた以外は実施例1と同様に処理して攪拌開始直後に、暗褐色のコロイドPCB(DMA)0minを得た。そのTEM観察から、四面体の形状選択性は80%であった。粒子径は平均4nmでそのばらつき3σは0.5nmであった。
実施例2において、PCA0.020gの代わりに、PCB0.030gを用いた以外は実施例2と同様に処理して、暗褐色コロイドPCB(DMA)70min を得た。TEM観察で、四面体の形状選択性は74%を示し、粒子径は平均10nmで、ばらつき3σは1.2nmであった。
上記4核パラジウム錯体PCA0.020gをN,N-ジメチルアセトアミド(DMA)1mlに添加し空気中25℃で攪拌した。5分間攪拌後、0.02gのPVP粉末(アルドリッチ製、分子量40,000)を添加し、なお50分間攪拌保持し、暗褐色均一コロイド溶液を得た。このコロイドのTEM観察から、実施例1と同様、四面体の形状選択性は75%、平均粒子径は6.0nmであった。このコロイドを空気中室温で10日間保存した後、再度TEM観察したが、形状選択率、粒子径ともほとんど変化がなかった。
上記4核パラジウム錯体PCA0.020gと0.154gのチタニア粉末(TiO2, 触媒学会の参照触媒JRC-TIO-2)をN,N-ジメチルアセトアミド(DMA)1mlに添加し空気中25℃で攪拌した。50分間攪拌後、攪拌を止めて静置させると、青灰色の固体と無色透明な上澄液が得られた。固体を濾過分離しDMAで洗浄し真空乾燥させて、6.2重量%パラジウム担持チタニア触媒PCA(DMA)/TiO2 0minを得た。この触媒をHR-TEMおよびFE-SEM(Hitachi S-5000L, 加速電圧18.0kV)で観察すると、チタニア表面に四面体の微粒子が凝集することなく均一に分散された状態で担持されていた。TEM像の三角形の一辺の平均の長さは6.4nmであり、コロイドPCA(DMA)5minとほぼ同様の粒子形状分布並びに粒子径分布を示した。即ち、四面体パラジウム微粒子は担体チタニア粒子の存在下でもチタニアがない場合と同様に反応の初期に生成し直ちに共存するチタニア粒子の表面に、形状と粒子径を保持したまま固定化されたと推測される。
実施例2で得られた四面体パラジウムコロイドに実施例7で用いたのと同じチタニア粉末を0.154g添加し、25℃、空気中で30分攪拌した後、攪拌を止めて静置させて固体と上澄液を得、固体を濾過分離しDMAで洗浄し真空乾燥させて、担持チタニア触媒PCA(DMA)/TiO2 70minを得た。TEM観察から四面体の形状選択性および粒子径分布は実施例2とほぼ同様と確認された。
実施例7において、錯体PCAを用いる代わりに、錯体PCBをPd換算で0.01g用いた以外は実施例7と同様に処理してPCB(DMA)/TiO2 0min を得た。TEM像からチタニアに担持されたパラジウム微粒子の形状選択性は実施例4とほぼ同様80%であった。粒子径は平均4nmでそのばらつき3σは0.5nmであった
実施例5で得られたコロイドPCB(DMA)70min 1mlに、実施例7で用いたチタニア粉末0.154gを添加し空気中25℃で30分間攪拌保持した後、攪拌を止めて静置させて固体と上澄液を得、固体を濾過分離しDMAで洗浄し真空乾燥させて、6.2重量%パラジウム担持チタニア触媒PCB(DMA)/TiO2 70min を得た。TEM像からチタニアに担持されたパラジウム微粒子の形状選択性は実施例5と同様74%で、粒子径は平均10nm、バラツキ3σは1.5nmであった。
実施例7において、溶媒DMAの代わりにN-メチルピロリドン(NMP)1mlを、担体チタニアの代わりに0.154gのアルミナ(ICN ファーマシューティカル製、 N. Akt.I )を用いた以外は、実施例7と同様に処理して、パラジウム担持アルミナ触媒PCA(NMP)/Al2O3 0min を得た。
実施例11において、アルミナ担体としてICN ファーマシューティカル製のアルミナの代わりに、触媒学会の参照触媒JRC-ALO-4を用いた以外は、実施例11と同様に処理してパラジウム担持アルミナ触媒PCA(NMP)/Al2O3 0min を得た。
実施例7において、溶媒DMAの代わりにN-メチルピロリドン1mlを、担体チタニアの代わりに0.154gのヒドロキシアパタイト(和光純薬工業製)を用いた以外、実施例7と同様に処理してパラジウム担持ヒドロキシアパタイト触媒PCA(NMP)/HAP0min を得た。
パイレックス(登録商標)フラスコに溶媒DMF5mlを入れ、これに、臭化ベンゼン(1.0mmol)、フェニルほう酸(1.5mmol)および炭酸カルシウム(2.0mmol)を添加して、フラスコ内部をアルゴンガスで置換し攪拌混合した後、オイルバスで加熱昇温し液温130℃迄昇温し、これに実施例3で得られたパラジウムコロイドを0.11ml (Pd換算0.01mmol)添加した。アルゴン流通下130℃で8時間攪拌保持した。室温まで放冷後、反応液をガスクロマトグラフィーで分析(内部標準法)して目的生成物ビフェニルを収率99%で得た。結果を表1に示す。反応スキームは下記のとおりである。
実施例14において、臭化ベンゼンの代わりに塩化ベンゼン(1.0mmol)を用いて反応時間を24時間とした以外は実施例14と同様に処理してビフェニルを収率31%で得た。結果を表1に示す。
非特許文献7の方法に従って、以下のように球形パラジウムのPVP保護コロイドを製造した。0.09g の塩化パラジウムと6mlの0.2N塩酸を250mlの脱イオン水に入れ、0.07gのポリビニルピロリドンPVP(アルドリッチ製、分子量40,000)と1N塩酸4滴とを加えて加熱沸騰させ、14mlのエタノールを添加して3時間攪拌保持し、暗褐色のパラジウムコロイド(Pd濃度2mmol/l)を得た。TEM観察で四面体微粒子の割合は10%以下で殆どが球形ナノ粒子であり、平均粒子径は3nmであった。実施例14において、実施例3で得た四面体パラジウムコロイドの代わりにこの球形パラジウムPVP保護コロイドを5ml (Pd換算0.01mmol) 用いた以外は、実施例14と同様に処理してビフェニルを収率27%で得た。結果を表1に示す。
実施例15において、実施例3で得た四面体パラジウムコロイドの代わりに比較例1で得た球形パラジウムPVP保護コロイドをPd換算0.01mmol用いた以外は、実施例15と同様に処理してビフェニルを収率5%で得た。結果を表1に示す。
実施例14において、触媒としてパラジウムコロイドを用いる代わりに、実施例7の四面体パラジウム担持チタニア触媒PCA(DMA)/TiO2 0minをPd換算0.01mmol用いる以外は、実施例14と同様に処理して、ビフェニルを収率71%で得た。
実施例14において、触媒としてパラジウムコロイドを用いる代わりに、実施例9および実施例10それぞれのパラジウム担持チタニア触媒、すなわち、PCB(DMA)/TiO2 0minおよびPCB(DMA)/TiO2 70minを用い、反応時間を5時間とした以外は、実施例14と同様に処理して、ビフェニルをそれぞれ、89%および67%の収率で得た。
実施例14において、触媒としてパラジウムコロイドの代わりに実施例11および12の四面体パラジウム担持アルミナ触媒PCA(NMP)/Al2O3 0min を用い、反応時間を3時間とした以外は実施例14と同様に処理して生成物ビフェニルをそれぞれ>99%および92%の収率で得た。
実施例18において、触媒として四面体パラジウム担持アルミナ触媒の代わりに、市販のパラジウム担持アルミナ触媒5%Pd/Al2O3(和光純薬工業製)をPd換算0.01mmol使用した以外は、実施例18と同様に処理して、ビフェニルを収率53%で得た。
実施例14において、触媒としてパラジウムコロイドの代わりに実施例13の担持ヒドロキシアパタイト触媒を用い、反応時間を5時間とした以外は、実施例14と同様に処理してビフェニルの収率75%を得た。
パイレックス(登録商標)フラスコに溶媒DMSO 5mlを入れ、これに、フェニルアセチレン(1.0mmol)を添加して、フラスコ内部を水素ガスで置換し攪拌混合した後、オイルバスで加熱昇温し液温40℃迄昇温し、これに実施例7で得られた四面体パラジウム担持チタニア触媒PCB(DMA)0min/TiO2の5mg (Pd換算2.5μmol)を添加した。常圧水素流通下3時間後、反応液をガスクロマトグラフィーで分析(内部標準法)してC−C三重結合のみが水素化されて生成したスチレンを収率96%で得た。
Claims (6)
- 4核の前駆体パラジウム錯体を溶媒中に溶解して均一溶液を得、この均一溶液中でパラジウム錯体を分解することにより形状選択的に四面体粒子を生成させるパラジウム微粒子の製造方法。
- 該前駆体パラジウム錯体の分解を、酸素含有雰囲気中で行うことを特徴とする請求項1に係る製造方法。
- 該前駆体パラジウム錯体がカルボニル配位子を含む請求項1または2に係る製造方法。
- 該前駆体パラジウム錯体が脂肪族又は芳香族のカルボキシレート配位子を含む請求項1,2、または3に係る製造方法。
- 該前駆体パラジウム錯体を非プロトン性の極性溶媒に溶解することを特徴とする請求項1、2、3、または4に係る製造方法。
- 該極性溶媒がカルボン酸アミドである請求項5に係る製造方法。
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US8246714B2 (en) * | 2009-01-30 | 2012-08-21 | Imra America, Inc. | Production of metal and metal-alloy nanoparticles with high repetition rate ultrafast pulsed laser ablation in liquids |
JP5547428B2 (ja) * | 2009-06-17 | 2014-07-16 | 国立大学法人北海道大学 | 金属微粒子を触媒とする有機化合物の反応方法 |
US8591624B2 (en) * | 2010-02-25 | 2013-11-26 | National Tsing Hua University | Methods for preparing hydrophobic metal nanoparticles and precursors used therein |
JP6159621B2 (ja) * | 2013-08-28 | 2017-07-05 | 石福金属興業株式会社 | コアシェル触媒用コア材料に適した高分散担持されたパラジウム触媒の製造方法 |
CN105531026B (zh) * | 2013-09-10 | 2018-03-20 | 新日铁住金株式会社 | 氧化催化剂、废气处理装置、蓄热燃烧器、气体中的可燃成分的氧化方法和气体中的氮氧化物的去除方法 |
US9388477B1 (en) * | 2015-01-20 | 2016-07-12 | Uchicago Argonne, Llc | Noble metal superparticles and methods of preparation thereof |
JP6413821B2 (ja) * | 2015-02-13 | 2018-10-31 | 新日鐵住金株式会社 | 排ガス浄化用又は燃料電池電極用触媒の製造方法及び排ガス浄化用又は燃料電池電極用触媒 |
JP6464791B2 (ja) * | 2015-02-13 | 2019-02-06 | 新日鐵住金株式会社 | 排ガス浄化用又は燃料電池電極用触媒の製造方法及び排ガス浄化用又は燃料電池電極用触媒 |
TWI824005B (zh) | 2018-09-13 | 2023-12-01 | 日商三菱瓦斯化學股份有限公司 | 含鈀的組成物及過氧化氫之製造方法 |
CN113036169A (zh) * | 2021-03-15 | 2021-06-25 | 电子科技大学 | 一种纳米钯催化剂的制法及其在小分子氧化中的应用 |
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JP2003268424A (ja) * | 2002-03-11 | 2003-09-25 | Rikogaku Shinkokai | 金属粒子およびその製造方法、並びに触媒およびその製造方法 |
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