JP2007100117A - 金属ナノ粒子、それを含む触媒及びアルキン化合物の水素化方法 - Google Patents
金属ナノ粒子、それを含む触媒及びアルキン化合物の水素化方法 Download PDFInfo
- Publication number
- JP2007100117A JP2007100117A JP2005287439A JP2005287439A JP2007100117A JP 2007100117 A JP2007100117 A JP 2007100117A JP 2005287439 A JP2005287439 A JP 2005287439A JP 2005287439 A JP2005287439 A JP 2005287439A JP 2007100117 A JP2007100117 A JP 2007100117A
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- Prior art keywords
- compound
- diol
- nanoparticles
- metal
- alkyne
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- 239000002082 metal nanoparticle Substances 0.000 title claims abstract description 69
- 239000003054 catalyst Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000003223 protective agent Substances 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 14
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 14
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 14
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 12
- 229910052737 gold Inorganic materials 0.000 claims abstract description 9
- 239000002105 nanoparticle Substances 0.000 claims description 102
- 230000002776 aggregation Effects 0.000 claims description 49
- 238000004220 aggregation Methods 0.000 claims description 47
- 150000002736 metal compounds Chemical class 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000463 material Substances 0.000 abstract description 9
- 230000001681 protective effect Effects 0.000 abstract description 6
- 230000016615 flocculation Effects 0.000 abstract 4
- 238000005189 flocculation Methods 0.000 abstract 4
- 229910000765 intermetallic Inorganic materials 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000002441 X-ray diffraction Methods 0.000 description 10
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- 101150003085 Pdcl gene Proteins 0.000 description 9
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
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- 239000012535 impurity Substances 0.000 description 6
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- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 4
- IRUCBBFNLDIMIK-FPLPWBNLSA-N (z)-oct-4-ene Chemical compound CCC\C=C/CCC IRUCBBFNLDIMIK-FPLPWBNLSA-N 0.000 description 4
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 4
- 229910004013 NO 2 Inorganic materials 0.000 description 4
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- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
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- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910003771 Gold(I) chloride Inorganic materials 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- BTDWSZJDLLLTMI-UHFFFAOYSA-N hex-2-yn-1-ol Chemical compound CCCC#CCO BTDWSZJDLLLTMI-UHFFFAOYSA-N 0.000 description 3
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- 150000002430 hydrocarbons Chemical class 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 3
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
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- DGXZDQFYFRCMJB-UHFFFAOYSA-N prop-1-yne-1,3-diol Chemical compound OCC#CO DGXZDQFYFRCMJB-UHFFFAOYSA-N 0.000 description 1
- GHUURDQYRGVEHX-UHFFFAOYSA-N prop-1-ynylbenzene Chemical group CC#CC1=CC=CC=C1 GHUURDQYRGVEHX-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
【解決手段】 アルキン化合物またはアルケン化合物を含む凝集保護剤と、Ru、Co、Rh、Ni、Pd、Pt、Os、Ag又はAuから選択される1種または2種以上の金属化合物(ただし、金属化合物が1種の場合はPdを除く)と、還元剤を反応させて金属ナノ粒子を製造する。また、上記方法により製造した金属ナノ粒子を触媒として用い、水素又は水素を供与する化合物の存在下、反応基質であるアルキン化合物を水素化した、アルカン化合物またはアルケン化合物を製造する。
【選択図】 なし
Description
さらに、上記記載の金属ナノ粒子を含む、触媒を提供し、
さらに、上記記載の触媒を用いて、水素又は水素を供与する化合物の存在下、反応基質であるアルキン化合物またはアルケン化合物を水素化する、アルケン化合物またはアルカン化合物の製造方法を提供するものである。
アルキン化合物は、金属1モル当たり0.1〜100当量用いることが好ましいが、0.5〜50当量がより好ましく、1〜10当量が最も好ましい。
アルケン化合物は、金属1モル当たり0.1〜100当量用いることが好ましいが、0.5〜50当量がより好ましく、1〜10当量が最も好ましい。
(MXmLn)−p(Yk)+P …(2)
(MXmLn)+p(Zk)―P …(3)
(一般式(1)〜(3)中、MはRu、Co、Rh、Ni、Pd、Pt、Os、Ag又はAuから選択される1種または2種以上を示し(ただし、用いる金属化合物が一種類の場合にはPdを除く。)、Xは各々独立して同じでも異なってもよいアニオン性基、Lは各々独立して同じでも異なってもよい、単座若しくは多座配位子、又は水、Yはカチオン性基、Zはアニオン性基、mは0〜6のいずれかの整数、nは0〜6のいずれかの整数、kは1〜4の何れかの整数、pは1または2の整数を表す。)
アニオン性基Zとしては、例えばフッ素、塩素、臭素、ヨウ素などのハロゲン、硫黄、NO2、NO3、CN、OH、SO4、S2O3、アセテート、アセチルアセトン、π−アリル基、プロピオネート基、カルボキシル基、CF3COO基等が挙げられる。
カチオン性基Yとしては、(NH4)+基、(Li)+基、(Na)+基、(K)+基、[H]+基等が挙げられる。
mは0から6、nは0から6、kは1から4、pは1または2を示す。
RuCl3・nH2O、RuBr3・nH2O、[RuCl(p−cymene)]2、Ru(methylallyl)2(COD)、RuCl2(PPh3)3、Co(OAc)2・nH2O、Co(acac)2・nH2O、Co(acac)3・nH2O、CoF2、CoF3、CoCl2・nH2O、CoBr2・nH2O、Co(NO3)2・nH2O、Co(ClO4)2・nH2O、[RhCl(COD)]2、Rh2(OAc)4、Rh(acac)3、RhCl3・nH2O、RhBr3・nH2O、Rh(NO3)2・nH2O、NiCl2・nH2O、NiBr2・nH2O、Ni(OAc)2・nH2O、NiCl2(PPh3)2、NiCl2(dppe)、Ni(NO3)2、Ni(ClO4)2・nH2O、PdF2、PdCl2、PdBr2、PdI2、Pd(OAc)2、Pd(NO3)2、Pd(OH)2、PdSO4、Pd(CN)2、PdS、Pd(OCOCF3)2、ビス(アセチルアセトン)パラジウム、アリルパラジウムクロリド、PdCl2(NH3)2、PdBr2(NH3)2、PdI2(NH3)2、Pd(NO2)2(NH3)2、Pd(PhCN)2Cl2、Pd(CH3CN)2Cl2、(2,2−ビピリジン)パラジウムジクロリド、(1,5−シクロオクタジエン)パラジウムジクロリド、エチレンジアミンパラジウムジクロリド、N,N,N’,N’,−テトラメチルエチレンジアミンパラジウムジクロリド、及び(1,10−フェナントロリン)パラジウムジクロリド、PtCl2、PtCl4、PtBr2、PtI2、Pt(CN)2、Pt(COD)Br2、Pt(PhCN)2Cl2、Pt(PPh3)2Cl2、Pt(acac)2、Ag(OAc)、AgF、AgF2,AgCl、AgBr、AgI、AgCN、AgNO3、AgNO2、AgClO4、AgBF4、AuCl3・nH2O、AuBr3・nH2O、AuCN、AuI等が挙げられる。
還元性基を有するアルキン化合物または還元性基を有するアルケン化合物としては、具体的に、アルキニルアルコール、アルケニルアルコール、アルキニルアミン、アルケニルアミン、アルキニルアルデヒド、アルケニルアルデヒドなどであり、さらに具体的には、前記したアルキニルアルコールやアルケニルアルコールなどである。これら化合物の使用量は、前記アルキン化合物およびアルケン化合物と同様である。
このうち、好ましい溶媒としてはアミド系溶媒であり、DMF及びDMAがナノ粒子を安定化させるため特に好ましい。使用する溶媒の量には特に制限はなく、金属1モル当たり、1〜1000リットル程度を目安とするが、好ましくは10〜100リットルである。
なお、アルキン化合物、アルケン化合物の具体例は前記同様であり、本明細書ではアルキン化合物はアルキニルアルコール化合物を含む上位概念の用語として用いる。
なお、本発明の触媒には、本発明のナノ粒子を2種以上含んでいる場合も当然に含まれる。
塩基と還元剤の含有効果は、ナノ粒子を構成する金属種類や基質構造によって変化するため一概に論ずることはできないが、基質構造中に、還元剤と直接反応を起こすような置換基が含まれていない場合には、還元剤及び/又は塩基を含有させることができる。このような場合には、還元剤び/又は塩基の含有効果を得ることができる。
すなわち、本発明のアルケン化合物またはアルカン化合物の製造方法は、上述した触媒を用いて、反応溶媒中、水素又は水素を供与する化合物の存在下、反応基質であるアルキン化合物またはアルケン化合物を水素化することに行われる。
ここで、反応基質に内部アルキンを用いた場合は、高選択的に対応するシスアルケン化合物を得ることができる。
触媒の使用量は、ナノ粒子を構成する金属の種類、反応基質の種類、反応容器や経済性などによって異なるが、反応基質であるアルキン化合物とのS/Cが10〜100,000で用いることができる。より実用的には、50〜1,000の範囲で用いることが好ましい。なお、本明細書では、S/Cを算出するにあたり、「C」を触媒に含まれる金属量と定義した。
本発明のアルキン化合物の水素化反応で用いる、水素を供与する化合物は、具体的には重水素、アルコール、ギ酸、金属ヒドリドが挙げられ、好ましくは重水素または水素が用いられる。かかる化合物の使用量は、アルキン基質に対して大過剰量が好ましい。
本発明のアルキン化合物の水素化方法においては、反応系内に他の更なる添加物を加えてもよい。
撹拌子を備えた20mlシュレンク型反応管に、ルテニウム化合物としてRuCl3・2.5H2O(266.4mg、1.054mmol)を量り取り、アルゴン雰囲気下でDMF(10.5ml)、凝集保護剤として4−オクチン(1.55ml,10.5mmol)を加えて攪拌した。続いて還元剤であるNaBH4(79.8mg,2.11mmol,Ruに対して2.0当量)を加えて攪拌すると、反応が開始して溶液の色調が濃茶色に変化していった。この様子は、Ruナノ粒子が生成していることを示すものと考えられる。その後、室温で3時間攪拌し、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=40(deg)付近にRuに由来する回折が認められ、生成した化合物が0価Ruナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は2.5nmと計算された。
金属化合物としてCoCl2・6H2Oを用いたほかは実施例1と同条件で反応を行い、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=44(deg)付近にCoに由来する回折が認められ、生成した化合物が0価Coナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は3.0nmと計算された。
金属化合物としてRhCl3・2.4H2Oを用いたほかは実施例1と同条件で反応を行い、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=40(deg)付近にRhに由来する回折が認められ、生成した化合物が0価Rhナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は1.3nmと計算された。
金属化合物としてNiBr2・3H2Oを用いたほかは実施例1と同条件で反応を行い、濃赤褐色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、測定中に試料の酸化が生起したため明瞭な回折パターンは得られなかったが、NiBr2のパターンは認められないうえ、ナノ粒子に特有の濃赤褐色の色調が認められ、Niナノ粒子が生成したものと推定された。
金属化合物としてPtCl4を用いたほかは実施例1と同条件で反応を行い、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=39(deg)付近にPtに由来する回折が認められ、生成したナノ粒子が0価Ptナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は1.6nmと計算された。
凝集保護剤としてジフェニルアセチレンを用いたほかは実施例5と同条件で反応を行い、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=38(deg)付近にPtに由来する回折が認められ、生成したナノ粒子が0価Ptナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は2.7nmと計算された。
金属化合物としてAuCl3を用いたほかは実施例1と同条件で反応を行い、濃青色のDMF溶液を得た。若干の凝集した粒子が認められた。
得られた化合物のX線回折測定を行ったところ、2θ=38(deg)、44(deg)、64(deg)、77(deg)、81(deg)付近にAuに由来する回折が認められ、生成した化合物が0価Auナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は11.0nmと計算された。
撹拌子を備えた20mlシュレンク型反応管に、銀化合物としてAg(OAc)(170.7mg,1.023mmol)を量り取り、アルゴン雰囲気下でDMF(10.2ml)を加えて攪拌した。続いて、還元剤兼凝集保護剤である2−ブチン−1,4−ジオール(881mg,10.23mmol,Agに対して10.0当量)を加えて攪拌すると、反応が開始して溶液の色調が少しずつ濃茶色に変化していった。この様子は、Agナノ粒子が生成していることを示すものと考えられる。その後、室温で12時間攪拌し、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=38(deg)、64(deg)、77(deg)付近にAgに由来する回折が認められ、生成した化合物が0価Agナノ粒子であると同定された。また、回折ピークの半値幅から、結晶径の平均値は13.5nmと計算された。
金属化合物としてRh2(OAc)4を用い、反応温度を100℃としたほかは実施例8と同条件で反応を行い、濃赤褐色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、明瞭な回折パターンは得られなかったが、Rh2(OAc)4のパターンは認められないうえ、ナノ粒子に特有の濃赤褐色の色調が認められ、Rhナノ粒子が生成したものと推定された。
撹拌子を備えた20mlシュレンク型反応管に、金属化合物としてPd(OAc)2(105mg、0.468mmol)とRh2(OAc)4(103mg、0.468mmol)を量り取り、アルゴン雰囲気下でDMF(9.4ml)、還元剤兼凝集保護剤である2−ブチン−1,4−ジオール(806mg,9.36mmol,PdとRhの合算値に対して10.0当量)を加えて攪拌すると、反応が開始して溶液の色調が濃茶色に変化していった。この様子は、ナノ粒子が生成していることを示すものと考えられる。その後、100℃で1時間攪拌し、濃茶色のDMF溶液を得た。凝集した粒子は認められなかった。
得られた化合物のX線回折測定を行ったところ、2θ=39.8(deg)、65.3(deg)付近に回折が認められ、ナノ粒子が生成したと同定された。また、回折ピークの半値幅から、結晶径の平均値は2.3nmと計算された。
[参考例]
実施例8で調製したAgナノ粒子を含むDMF溶液を、ガラス板上に塗布し、溶媒及び凝集保護剤を室温で減圧留去した。溶媒及び凝集保護剤を留去した後には、銀白色を呈する薄膜が得られた。
Claims (10)
- アルキン化合物またはアルケン化合物を含む凝集保護剤と、Ru、Co、Rh、Ni、Pd、Pt、Os、Ag又はAuから選択される1種または2種以上の金属化合物(ただし、金属化合物が一種類の場合はPdを除く。)と、還元剤を反応させる、金属ナノ粒子の製造方法。
- 還元性基を有するアルキン化合物または還元性基を有するアルケニル化合物を含む凝集保護剤と、Ru、Co、Rh、Ni、Pd、Pt、Os、Ag又はAuから選択される1種または2種以上の金属化合物(ただし、金属化合物が一種類の場合はPdを除く。)を反応させる、金属ナノ粒子の製造方法。
- 前記還元性基が水酸基である、請求項2に記載の金属ナノ粒子の製造方法。
- アルキン化合物またはアルケン化合物を含む凝集保護剤を有する、Ru、Co、Rh、Ni、Pd、Pt、Os、Ag又はAuから選択される1種または2種以上の金属ナノ粒子(ただし、Pdナノ粒子の場合を除く。)。
- 前記アルキン化合物またはアルケン化合物が炭素数2〜25の化合物である、請求項4に記載の金属ナノ粒子。
- 請求項4または5に記載の金属ナノ粒子を含む、触媒。
- 請求項4または5に記載の金属ナノ粒子と塩基及び/又は還元剤とを含む、触媒。
- 前記還元剤がボロヒドリド化合物である、請求項7に記載の触媒。
- 請求項6〜8のいずれかに記載の触媒を用いて、水素又は水素を供与する化合物の存在下、反応基質であるアルキン化合物またはアルケン化合物を水素化する、アルケン化合物またはアルカン化合物の製造方法。
- 前記アルキン化合物が内部アルキン化合物である、請求項9に記載のアルケン化合物の製造方法。
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Cited By (13)
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WO2009090767A1 (ja) * | 2008-01-17 | 2009-07-23 | Applied Nanoparticle Laboratory Corporation | 複合銀ナノ粒子、複合銀ナノペースト、その製法、製造装置、接合方法及びパターン形成方法 |
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US9732015B2 (en) | 2015-05-29 | 2017-08-15 | Uop Llc | Process for the selective hydrogenation of acetylene to ethylene |
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JP2010162443A (ja) * | 2009-01-13 | 2010-07-29 | Furuya Kinzoku:Kk | 白金ブラック粉末及び白金ブラックのコロイド並びにそれらの製造方法 |
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JP2015034347A (ja) * | 2009-04-24 | 2015-02-19 | 独立行政法人科学技術振興機構 | 固溶体型合金微粒子およびその製造方法 |
JP2011026665A (ja) * | 2009-07-27 | 2011-02-10 | National Institute For Materials Science | 樹枝状部分を有する金属ナノ粒子及びその製法 |
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JP2012116790A (ja) * | 2010-12-01 | 2012-06-21 | Daicel Corp | エポキシ化合物の脱酸素によるアルケンの製造方法 |
CN103370153A (zh) * | 2011-03-04 | 2013-10-23 | 丰田自动车株式会社 | 金属粒子和含有该金属粒子的排气净化用催化剂、以及它们的制造方法 |
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JP2017012999A (ja) * | 2015-07-01 | 2017-01-19 | 国立大学法人大阪大学 | 金−セリウム酸化物複合体触媒および該触媒を用いた選択的水素化方法 |
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WO2021029389A1 (ja) * | 2019-08-15 | 2021-02-18 | Nsマテリアルズ株式会社 | 量子ドット、及び、その製造方法 |
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