JP5963874B2 - 多様な溶媒中で高活性を示す無機/ポリマーハイブリッド触媒材料 - Google Patents
多様な溶媒中で高活性を示す無機/ポリマーハイブリッド触媒材料 Download PDFInfo
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- JP5963874B2 JP5963874B2 JP2014536025A JP2014536025A JP5963874B2 JP 5963874 B2 JP5963874 B2 JP 5963874B2 JP 2014536025 A JP2014536025 A JP 2014536025A JP 2014536025 A JP2014536025 A JP 2014536025A JP 5963874 B2 JP5963874 B2 JP 5963874B2
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- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000001523 electrospinning Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- OJRHLZXQEXLUGU-UHFFFAOYSA-N methyl 3-(2-acetamidophenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=CC=C1NC(C)=O OJRHLZXQEXLUGU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000005324 oxide salts Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 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
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Description
式中、Rは水素、炭素原子数が1〜約30のアルキル、炭素原子数が約6〜18のアリールであり、R1、R2およびR3は互いに同一あるいは異なっており、水素、炭素原子数が1〜約30のアルキル、炭素原子数が1〜約30のアルケニル、炭素原子数が1〜約30のアルキニル、炭素原子数が約6〜18のアリール、アミド、アミン、炭素原子数が1〜約30のアルコキシド、炭素原子数が1〜約30のエステル、炭素原子数が1〜約30のケトンを含む。アリール置換基も二環式であるか、融合種であるか、あるいは硫黄、酸素、窒素、リンなどのヘテロ原子を含んでよい。オレフィンは、好適な溶媒、限定するものではないが好ましくはメタノール中の溶液として触媒膜を含有する反応器に、導入される。水素化反応は、0.1bar〜50barの水素圧下、温度範囲−40℃〜150℃で0.5〜48時間行う。好ましいオレフィンとしては:メチル2‐アセトアミドアクリル酸塩、2‐アセトアミドアクリル酸、イタコン酸ジメチル、イタコン酸、メチル2‐アセトアミド桂皮酸塩、2‐アセトアミド桂皮酸が挙げられるがこれらに限定されるものではない。
式中、R1は水素、炭素原子数が1〜約30のアルキル、炭素原子数が約6〜18のアリール、アミド、アミン、炭素原子数が1〜約30のアルコキシド、炭素原子数が1〜約30のエステルである。アリール置換基も二環式であるか、融合種であるか、あるいは硫黄、酸素、窒素、リンなどのヘテロ原子を含んでよい。アルキンは、好適な溶媒、限定するものではないが好ましくはメタノール中の溶液として触媒膜を含有する反応器に、導入される。水素化反応は、0.1bar〜50barの水素圧下、温度範囲−40℃〜150℃で0.5〜48時間行う。好ましいアルキンとしては3‐ヘキシン‐1‐オールが挙げられるがこれに限定されるものではない。
式中、R1、R2、R3、R4は水素、炭素原子数が1〜約30のアルキル、炭素原子数が約6〜18のアリールである。ジエンは、好適な溶媒、限定するものではないが好ましくはメタノール中の溶液として触媒膜を含有する反応器に、導入される。水素化反応は、0.1bar〜50barの水素圧下、温度範囲−40℃〜150℃で0.5〜48時間行う。好ましいジエンとしては1,5‐シクロオクタジエン(1,5COD)が挙げられるがこれに限定されるものではない。
式中、R1は水素、炭素原子数が1〜約30のアルキル、炭素原子数が約6〜18のアリールである。α,β−不飽和ケトンは、好適な溶媒、限定するものではないが好ましくはメタノール中の溶液として触媒膜を含有する反応器に、導入される。水素化反応は、0.1bar〜50barの水素圧下、温度範囲−40℃〜150℃で0.5〜48時間行う。好ましいケトンとしては4‐フェニル‐ブテン‐2‐オンが挙げられるがこれに限定されるものではない。
Claims (14)
- 化学反応の際に触媒活性を示し、ケイ酸化合物、タングステン酸化合物およびジルコン酸化合物から選択される少なくとも1種とポリビニルアルコールまたはその誘導体で構成されるハイブリッド化合物から成る触媒材料であって、ハイブリッド化合物に金属粒子触媒が包埋されていること、およびハイブリッド化合物が‐CH 2 ‐CH 2 ‐O‐の単位と分岐構造を有するか、あるいはケイ素原子の一部にカルボキシル基が付加された‐Si(CH 3 ) 2 ‐O‐の単位を有するポリマー添加剤を含むことを特徴とする触媒材料。
- ‐CH2‐CH2‐O‐の単位と分岐構造を有するポリマー添加剤がポリオキシエチレン/ポリグリセリルエーテルであることを特徴とする請求項1に記載の触媒材料。
- 金属粒子触媒が、鉄、コバルト、ニッケル、銅、ルテニウム、ロジウム、パラジウム、銀、オスミウム、イリジウム、プラチナおよび金から選択される少なくとも1種であることを特徴とする請求項1または2に記載の触媒材料。
- 金属粒子触媒が、ルテニウム、ロジウム、パラジウム、銀、イリジウム、プラチナおよび金から選択される少なくとも1種であることを特徴とする請求項1または2に記載の触媒材料。
- 金属粒子触媒がパラジウムであることを特徴とする請求項1または2に記載の触媒材料。
- 触媒材料が膜であることを特徴とする請求項1または2に記載の触媒材料。
- 化学反応が水素化であることを特徴とする請求項1に記載の触媒材料。
- 水素化反応が下記式のオレフィンの水素化であることを特徴とする請求項7に記載の触媒材料。
式中、Rは水素、炭素原子数が1〜約30のアルキル、炭素原子数が約6〜18のアリールであり、R1、R2およびR3は互いに同一あるいは異なっており、水素、炭素原子数が1〜約30のアルキル、炭素原子数が1〜約30のアルケニル、炭素原子数が1〜約30のアルキニル、炭素原子数が約6〜18のアリール、アミド、アミン、炭素原子数が1〜約30のアルコキシド、炭素原子数が1〜約30のエステル、炭素原子数が1〜約30のケトンを含み、アリール置換基は二環式であるか、融合種であるか、あるいは硫黄、酸素、窒素、リンなどのヘテロ原子を含んでもよい。 - 水素化がオレフィン、イミン、エナミン、ケトン、α,β‐不飽和アルコール、ケトン、エステルまたは酸を含むプロキラル基質のエナンチオ選択的水素化であることを特徴とする請求項7に記載の触媒材料。
- 請求項1に記載の触媒材料を提供する方法であって:
1)ポリビニルアルコールまたはその誘導体およびポリマー添加剤を含む溶液中で、ケイ酸塩および/またはタングステン酸塩を酸で中和することによってハイブリッド化合物を合成した後、溶媒を除去し、
2)この様に合成したハイブリッド化合物を、金属粒子触媒の塩溶液に浸漬するか、あるいはそれを塗り付けた後、還元し、吸収した塩を金属粒子に変える:
ことを特徴とする方法。 - 請求項1に記載の触媒材料を提供する方法であって:
1)ポリビニルアルコールもしくはその誘導体およびポリマー添加剤を含む溶液中で、金属粒子触媒の塩、ジルコニウム塩および/もしくはオキシジルコニウム塩をアルカリで中和する方法で、ハイブリッド化合物を合成した後、溶媒を除去し、
2)あるいは、ポリビニルアルコールもしくはその誘導体、ポリマー添加剤、金属粒子触媒の塩、ならびにジルコニウム塩および/もしくはオキシジルコニウム塩の固体混合物をアルカリ溶液に浸漬するか、あるいはそれを塗り付け、中和し、
3)このように合成したハイブリッド化合物を還元し、金属粒子触媒の酸化物および/もしくは水酸化物を金属粒子に変える:
ことを特徴とする方法。
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BR112014019004A2 (ja) | 2017-06-20 |
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CN104125860A (zh) | 2014-10-29 |
EP2814607A4 (en) | 2015-11-11 |
BR112014019004A8 (pt) | 2017-07-11 |
US9884317B2 (en) | 2018-02-06 |
RU2014137160A (ru) | 2016-04-10 |
KR20140122224A (ko) | 2014-10-17 |
CN104125860B (zh) | 2017-03-08 |
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