JP5443592B2 - レニウムで促進されたエポキシ化触媒並びにその製造及び使用方法 - Google Patents
レニウムで促進されたエポキシ化触媒並びにその製造及び使用方法 Download PDFInfo
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- JP5443592B2 JP5443592B2 JP2012507260A JP2012507260A JP5443592B2 JP 5443592 B2 JP5443592 B2 JP 5443592B2 JP 2012507260 A JP2012507260 A JP 2012507260A JP 2012507260 A JP2012507260 A JP 2012507260A JP 5443592 B2 JP5443592 B2 JP 5443592B2
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- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910001648 diaspore Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
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- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 238000007037 hydroformylation reaction Methods 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical group O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910001682 nordstrandite Inorganic materials 0.000 description 1
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- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical class [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
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- 150000003281 rhenium Chemical class 0.000 description 1
- 150000003282 rhenium compounds Chemical class 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000009490 roller compaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 238000007569 slipcasting Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
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- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Description
気孔率(百分率)=100%×(総細孔容積(cc/g))/(0.25cc/g+総細孔容積(cc/g))
2つの成形多孔体のサンプルを、以下の手順にしたがって調製した。
担体Aは、本発明による、小板の形態のアルファ−アルミナ成形多孔体である。高かさ密度の擬ベーマイトと低かさ密度の擬ベーマイトとの配合物が約90%でありガンマ−アルミナ粉末が約10%である乾燥混合物を用意し、そして、前記の開始乾燥混合物の重量に対するパーセントで表して、5.0%のギ酸と4.6%の重フッ化アンモニウムを水溶液として、押出し可能な混練物を形成するのに十分な量の水とともに添加する。混合の後に混和物を押出し、乾燥し、約1000〜1400℃の温度で焼成して、アルミナ成分が完全にアルファ−アルミナに転化されるようにする。担体Aの特性を表1に示す。
担体Bは、ケイ酸ジルコニウムを2重量%混ぜた小板の形態のアルファ−アルミナ成形多孔体である。高かさ密度の擬ベーマイト約78.7%と、ガンマ−アルミナ粉末約19.7%と、粒状ケイ酸ジルコニウム約1.6%との乾燥混合物を用意し、そして、前記の開始乾燥混合物の重量に対するパーセントで表して、5.0%のギ酸と4.6%の重フッ化アンモニウムを水溶液として、押出し可能な混練物を形成するのに十分な量の水とともに添加する。混合の後に、混和物を押出し、乾燥し、約1000〜1400℃の温度で焼成して、アルミナ成分が完全にアルファ−アルミナに転化されるようにする。担体Bの特性を表2に示す。
担体Aと担体Bを基材として、同じ標的(target)促進剤濃度を有するエチレンエポキシ化触媒を、次の手順により調製した。
米国特許出願公開第2009/177000号明細書、その全開示はここで参照することによりあらゆる目的について本明細書中に組み込まれる、の「触媒調製」のところに記載されるようにして調製された、銀−アミン−シュウ酸塩(25.89重量%Ag)およそ140mLを用いて、担体A(60.39g)の第1の含浸を行う。担体は、減圧下で担体に含浸を行うための栓を備えたほぼ標準サイズのガラス容器中で、含浸される。含浸溶液を入れるために使用される分液漏斗が、ゴム栓を介して含浸容器の頂部にはめ込まれる。担体が入った含浸容器は、水銀柱約1〜2”(25〜50mm)の絶対圧まで15分間真空引きし、その後、分液漏斗と含浸容器の間の栓を開いて、含浸溶液を担体にゆっくり加える。すべての溶液が含浸容器に出た後(約15秒)、減圧を開放して圧力を大気圧に戻す。溶液の添加の後に、担体を周囲環境で15分間含浸溶液に浸漬したままにしておき、その後に過剰の溶液を15分間で排出する。
米国特許出願公開第2009/177000号明細書、その全開示はここで参照することによりあらゆる目的について本明細書中に組み込まれる、の「触媒調製」のところに記載されるようにして調製された、銀−アミン−シュウ酸塩(25.89重量%Ag)およそ140mLを用いて、担体B(60.96g)の第1の含浸を行う。担体は、減圧下で担体に含浸を行うための栓を備えたほぼ標準サイズのガラス容器中で、含浸される。含浸溶液を入れるために使用される分液漏斗が、ゴム栓を介して含浸容器の頂部にはめ込まれる。担体が入った含浸容器は、水銀柱約1〜2”(25〜50mm)の絶対圧まで15分間真空引きし、その後、分液漏斗と含浸容器の間の栓を開いて、含浸溶液を担体にゆっくり加える。すべての溶液が含浸容器に出た後(約15秒)、減圧を開放して圧力を大気圧に戻す。溶液の添加の後に、担体を周囲環境で15分間含浸溶液に浸漬したままにしておき、その後に過剰の溶液を15分間で排出する。
触媒A−1と触媒B−1は、標準的なガスリサイクル式の逆混合(back−mixed)オートクレーブ(J.M Berty、「Reactor for vapor PhaseCatalytic Studies」、Chemical Engineering Progress、第70巻、第5号、第78−84頁、1974年、の図2に記載された、よく知られた、逆混合、底部攪拌式の「マグネドライブ(Magnedrive)」オートクレーブに類似のもの)中において試験される。供給材料の組成は次のとおりである:30モル%のエチレン、8モル%の酸素、3.0モル%の二酸化炭素、0.5モル%のエタン、及び種々のppmvレベルの塩化エチル。各触媒供給の容積(volume)は0cm3である。流速は、約640リットル/時である。システム圧力は、約1900KPa−ゲージ圧である。本明細書に記載された手順に従って得られた触媒活性についての、単一の試験の標準偏差は、約1.2℃である。標準偏差は、当然に、装置の質及び試験を行う際に用いられる技法の正確さに依存し、したがって変化する。これらの標準偏差は、本明細書で報告される試験結果に当てはまると考えられる。
次の手順に従って、2つの成形多孔体のサンプルを調製した。
担体Cは、本発明による、小板の形態のアルファ−アルミナ成形多孔体である。高かさ密度の擬ベーマイトと低かさ密度の擬ベーマイトとの配合物が約78.7%であり、ガンマ−アルミナ粉末が約19.7%であり、粒状ケイ酸ジルコニウムが約1.6%である、乾燥混合物を用意し、そして、前記の開始乾燥混合物の重量に対するパーセントで表して、5.0%のギ酸と4.6%の重フッ化アンモニウムを水溶液として、押出し可能な混練物を形成するのに十分な量の水とともに添加する。混合の後に、混和物を押出し、乾燥し、約1000〜1400℃の温度で焼成して、アルミナ成分が完全にアルファ−アルミナに転化されるようにする。担体Cの特性を表4に示す。
担体Dは、小板の形態のアルファ−アルミナ成形多孔体である。高かさ密度の擬ベーマイト約78.7%と、ガンマ−アルミナ粉末約19.7%と、粒状ケイ酸ジルコニウム約1.6%との乾燥混合物を用意し、そして、前記の開始乾燥混合物の重量に対するパーセントで表して、5.0%のギ酸と4.6%の重フッ化アンモニウムを、水溶液として、押出し可能な混練物を形成するのに十分な量の水とともに添加する。混合の後に、混和物を押出し、乾燥し、約1000〜1400℃の温度で焼成して、アルミナ成分が完全にアルファ−アルミナに転化されるようにする。担体Bの特性を表2に示す。
担体Cと担体Dを基材として、同じ標的促進剤濃度を有するエチレンエポキシ化触媒を、次の手順により調製した。
米国特許出願公開第2009/177000号明細書、その全開示はここで参照することによりあらゆる目的について本明細書中に組み込まれる、の「触媒調製」のところに記載されるようにして調製された、銀−アミン−シュウ酸塩(25.89重量%Ag)およそ50mLを用いて、担体C(20.45g)の第1の含浸を行う。担体は、減圧下で担体に含浸を行うための栓を備えたほぼ標準サイズのガラス容器中で、含浸される。含浸溶液を入れるために使用される分液漏斗が、ゴム栓を介して含浸容器の頂部にはめ込まれる。担体が入った含浸容器は、水銀柱約1〜2”の絶対圧まで15分間真空引きし、その後、分液漏斗と含浸容器の間の栓を開いて、含浸溶液を担体にゆっくり加える。すべての溶液が含浸容器に出た後(約15秒)、減圧を開放して圧力を大気圧に戻す。溶液の添加の後に、担体を周囲環境で15分間含浸溶液に浸漬したままにしておき、その後に過剰の溶液を15分間で排出する。
米国特許出願公開第2009/177000号明細書、その全開示はここで参照することによりあらゆる目的について本明細書中に組み込まれる、の「触媒調製」のところに記載されるようにして調製された、銀−アミン−シュウ酸塩(25.89重量%Ag)およそ50mLを用いて、担体D(20.25g)の第1の含浸を行う。担体は、減圧下で担体に含浸を行うための栓を備えたほぼ標準サイズのガラス容器中で、含浸される。含浸溶液を入れるために使用される分液漏斗が、ゴム栓を介して含浸容器の頂部にはめ込まれる。担体が入った含浸容器は、水銀柱約1〜2”の絶対圧まで15分間真空引きし、その後、分液漏斗と含浸容器の間の栓を開いて、含浸溶液を担体にゆっくり加える。すべての溶液が含浸容器に出た後(約15秒)、減圧を開放して圧力を大気圧に戻す。溶液の添加の後に、担体を周囲環境で15分間含浸溶液に浸漬したままにしておき、その後に過剰の溶液を15分間で排出する。
触媒C−1と触媒D−1は、1/4インチ(外径)のステンレススチール反応管(ワンススルー操作)中において試験される。破砕した触媒(30/50メッシュの大きさにされる)0.7gを、同じ粒径画分のDenstone(米国Norton社の不活性物)と重量比1:1で徹底的に混合し、そして反応管内に入れる。供給材料の組成は次のとおりである:30モル%のエチレン、8モル%の酸素、1.5モル%の二酸化炭素、0.7モル%のエタン、及び種々のppmvレベルの塩化エチル。全体の入口ガス流速は、ガスの毎時空間速度が、未破砕触媒について算出して、10000h−1となるように調節する。反応器圧力は、約1950KPa−ゲージ圧である。本明細書に記載された手順に従って得られた触媒活性についての、単一の試験の標準偏差は、約0.33℃である。
Claims (5)
- 成形多孔体上に堆積させた少なくとも1種の触媒種と促進量のレニウムと追加的な促進剤とを含む、レニウムによって促進されたエポキシ化触媒であって、前記成形多孔体が、1ミクロン未満の直径を有する細孔を、その総細孔容積対して20%未満の割合で含み、かつ、少なくとも1.0m2/gの表面積を有しており、前記追加的促進剤が、モリブデン、タングステン、リチウム、硫黄、マンガン、ルビジウム、セシウム、ナトリウム、又はこれらの組合せを含むものである、触媒。
- 前記成形多孔体が、1.3m 2 /gを超える表面積を含むものである、請求項1に記載の触媒。
- レニウムで促進されたエポシキ化触媒を製造する方法であって、
a)1ミクロン未満の直径を有する細孔を、総細孔容積に対して20%未満の割合で含み、かつ、少なくとも1.0m 2 /gの表面積を有している、成形多孔体を選択すること;及び
b)前記成形多孔体の上に、少なくとも1種の触媒種と促進量のレニウムとを堆積させること、
を含む方法。 - 1種以上のアルキレンと酸素とを含む供給材料を、請求項1に記載の触媒の存在下で反応させることを含む、アルキレンのエポキシ化方法。
- 1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネート、又はアルカノールアミンを調製する方法であって、請求項4に記載の方法によって調製されたアルキレンオキシドを、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネート、又はアルカノールアミンに転換することを含む方法。
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TW201100171A (en) | 2011-01-01 |
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