JP6755872B2 - 芳香族水素化触媒およびその使用 - Google Patents
芳香族水素化触媒およびその使用 Download PDFInfo
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- JP6755872B2 JP6755872B2 JP2017531182A JP2017531182A JP6755872B2 JP 6755872 B2 JP6755872 B2 JP 6755872B2 JP 2017531182 A JP2017531182 A JP 2017531182A JP 2017531182 A JP2017531182 A JP 2017531182A JP 6755872 B2 JP6755872 B2 JP 6755872B2
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Classifications
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- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
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- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
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Description
本発明は、芳香族を含有する炭化水素供給流の加工用の触媒およびその触媒の使用に関する。
多孔性無機固体は、工業的応用のための触媒および分離媒体として大いに有益であることが見出されている。特に、メソ細孔の周期的配列を有するシリカおよびアルミナなどのメソポーラス材料は、それらの均一かつ調整可能な細孔、高い表面積および大きい細孔体積のため、触媒プロセスでの使用に魅力的な材料である。そのようなメソポーラス材料は、大きい比表面積(例えば、1000m2/g)および大きい細孔体積(例えば、1cm3/g)を有することが知られている。これらの理由のため、そのようなメソポーラス材料は、反応性触媒を可能にする。
望ましい細孔直径(pore diameter)、細孔体積(pore volume)および表面積を有するオルガノシリカ材料を含む触媒支持体を達成し得ることが見出された。さらに、そのようなオルガノシリカ材料支持体は、構造指向剤(structure directing agent)、ポロゲン(porogen)または界面活性剤を必要とせずに問題なく調製することができる。
水素化触媒が、
(i)式[Z1OZ2OSiCH2]3(I)
[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基または別のモノマーのケイ素原子への結合を表す]
のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体と、
(ii)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属と
を含む、炭化水素供給流のための芳香族水素化プロセスを提供する。
本発明の様々な態様において、水素化触媒、水素化触媒を調製する方法および芳香族水素化プロセスが提供される。
本発明およびそれに対する特許請求の範囲の目的のため、周期表の命番方式は、IUPAC元素周期表による。
本発明は、特に芳香族水素化のための水素化触媒に関する。第1の実施形態において、(i)各Z1およびZ2が、独立して、水素原子、C1〜C4アルキル基または別のモノマーのケイ素原子への結合であり得る、式[Z1OZ2OSiCH2]3(I)のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体と、(ii)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属とを含む、水素化触媒が提供される。
1.式(I)のモノマー
種々の実施形態において、オルガノシリカ材料支持体は、各Z1および/またはZ2が水素原子であり得る、式[Z1OZ2OSiCH2]3(I)のモノマーの独立単位を含むポリマーであり得る。
種々の実施形態において、オルガノシリカ材料支持体は、式(I)の独立単位と組み合わせて、各Z3が、水素原子、C1〜C4アルキル基または別のモノマーのケイ素原子への結合を表し、各Z4が、C1〜C6アルキル基を表すモノマーなどの別のモノマーをさらに含んでいてもよい。
種々の実施形態において、オルガノシリカ材料支持体は、式(I)の独立単位および任意選択的に式(II)の独立単位と組み合わせて、各Z5が、水素原子、C1〜C4アルキル基または別のモノマーのケイ素原子への結合を表すことができ、Z6、Z7およびZ8が、それぞれ独立して、ヒドロキシル基、C1〜C4アルキル基、C1〜C4アルコキシ基、窒素含有C1〜C10アルキル基、窒素含有ヘテロアラルキル基、および窒素を含有する任意選択的に置換されたヘテロシクロアルキル基、ならびに別のモノマーのケイ素原子に結合した酸素原子からなる群から選択され得る、少なくとも1種の式Z5OZ6Z7Z8Si(III)の独立単位を有するモノマーなどの別のモノマーをさらに含んでいてもよい。
種々の実施形態において、オルガノシリカ材料支持体は、式(I)の独立単位および任意選択的に式(II)および/または式(III)の独立単位と組み合わせて、各Z9が、独立して、ヒドロキシル基、C1〜C4アルコキシ基または別のモノマーのケイ素原子に結合した酸素原子であり得、各Z10およびZ11が、独立して、ヒドロキシル基、C1〜C4アルコキシ基、C1〜C4アルキル基または別のモノマーのケイ素原子に結合した酸素原子であり得、各Rが、C1〜C8アルキレン基、C2〜C8アルケニレン基、C2〜C8アルキニレン基、窒素含有C1〜C10アルキレン基、任意選択的に置換されたC6〜C20アラルキルおよび任意選択的に置換されたC4〜C20ヘテロシクロアルキル基からなる群から選択され得る、少なくとも1種の式Z9Z10Z11Si−R−SiZ9Z10Z11(IV)の独立単位を有するモノマーなどの別のモノマーをさらに含んでいてもよい。
種々の実施形態において、オルガノシリカ材料は、式(I)の独立単位および任意選択的に式(II)、(III)、(IV)および/または(V)の独立単位と組み合わせて、M1が、第13族金属を表し、各Z12が、独立して、水素原子、C1〜C6アルキルまたは別のモノマーのケイ素原子への結合を表す、少なくとも1種の式M1(OZ12)3(V)の独立単位を有するモノマーなどの別のモノマーをさらに含んでいてもよい。
種々の実施形態において、オルガノシリカ材料は、式(I)の独立単位および任意選択的に式(II)、(III)および/または(IV)の独立単位と組み合わせて、M2が、第13族金属を表し、各Z13およびZ14が、独立して、水素原子、C1〜C6アルキルまたは別のモノマーのケイ素原子への結合を表す、少なくとも1種の式(Z13O)2M2−O−Si(OZ14)3(VI)の独立単位を有するモノマーなどの別のモノマーをさらに含んでいてもよい。
本明細書に記載のオルガノシリカ材料支持体は、約1〜約4度2θの1つのブロードピーク、特に約1〜約3度2θの1つのブロードピークを有する粉末X線回折パターンを示すことができる。追加的にまたは代わりに、オルガノシリカ材料は、約0.5〜約10度2θ、約0.5〜約12度2θ、約0.5〜約15度2θ、約0.5〜約20度2θ、約0.5〜約30度2θ、約0.5〜約40度2θ、約0.5〜約50度2θ、約0.5〜約60度2θ、約0.5〜約70度2θ、約2〜約10度2θ、約2〜約12度2θ、約2〜約15度2θ、約2〜約20度2θ、約2〜約30度2θ、約2〜約40度2θ、約2〜約50度2θ、約2〜約60度2θ、約2〜約70度2θ、約3〜約10度2θ、約3〜約12度2θ、約3〜約15度2θ、約3〜約20度2θ、約3〜約30度2θ、約3〜約40度2θ、約3〜約50度2θ、約3〜約60度2θまたは約3〜約70度2θの範囲においてピークを実質的に示さないことができる。
本明細書に記載のオルガノシリカ材料支持体は、合成溶液の組成次第で広範囲に変動するシラノール含有量を有することができる。シラノール含有量は、固体状態シリコンNMRによって好都合に決定することができる。
本明細書に記載のオルガノシリカ材料支持体は、有利にメソポーラス形態である。上記の通り、メソポーラスという用語は、約2nm〜約50nmの範囲の直径を有する細孔を有する固体材料を指す。オルガノシリカ材料の平均細孔直径は、例えば、BET(ブルナウアー−エメット−テラー)法などの当業者の専門知識の範囲内の窒素吸着−脱着等温線技術を使用して決定することができる。
オルガノシリカ材料の表面積は、例えば、BET(ブルナウアー−エメット−テラー)法などの当業者の専門知識の範囲内の窒素吸着−脱着等温線技術を使用して決定することができる。この方法により、全表面積、外部表面積およびミクロポーラス表面積が決定され得る。本明細書で使用される場合、および他に明示されない限り、「全表面積」は、BET法によって決定される全表面積を指す。本明細書で使用される場合、および他に明示されない限り、「ミクロポーラス表面積」は、BET法によって決定されるミクロポーラス表面積を指す。
本明細書に記載の方法によって製造されたオルガノシリカ材料の細孔体積は、例えば、BET(ブルナウアー−エメット−テラー)法などの当業者の専門知識の範囲内の窒素吸着−脱着等温線技術を使用して決定することができる。
水素化触媒は、少なくとも1種の触媒金属をさらに含んでいてもよい。少なくとも1種の触媒金属は、オルガノシリカ材料の細孔内に組み込まれてもよい。代表的な触媒金属としては、限定されないが、第6族金属、第8族金属、第9族金属、第10族金属またはそれらの組合せを含むことができる。代表的な第6族金属としては、限定されないが、クロム、モリブデンおよび/またはタングステンが含まれ、特にモリブデンおよび/またはタングステンを含むことができる。代表的な第8族金属としては、限定されないが、鉄、ルテニウムおよび/またはオスミウムを含むことができる。代表的な第9族金属としては、限定されないが、コバルト、ロジウムおよび/またはイリジウムが含まれ、特にコバルトを含むことができる。代表的な第10族金属としては、限定されないが、ニッケル、パラジウムおよび/または白金を含むことができる。
種々の態様において、水素化触媒は、結合剤をさらに含み得るか、または自己結合し得る。適切な結合剤としては、限定されないが、活性および不活性材料、合成または天然由来ゼオライト、ならびに無機材料、例えば、クレーおよび/または酸化物、例えば、シリカ、アルミナ、ジルコニア、チタニア、シリカ−アルミナ、酸化セリウム、酸化マグネシウム、またはそれらの組合せが含まれる。特に、結合剤は、活性および不活性材料、無機材料、クレー、アルミナ、シリカ、シリカ−アルミナ、チタニア、ジルコニアまたはそれらの組合せから選択されてよい。特に、結合剤は、シリカ−アルミナ、アルミナおよび/またはジルコニア、特にアルミナであってよい。シリカ−アルミナは、天然由来であり得るか、またはシリカおよび酸化金属の混合物を含む、ゼラチン状沈殿物またはゲルの形態のいずれかであり得る。本明細書において、ゼオライト結合剤材料と関連する、すなわち、それと組み合わせて、またはその合成中に存在する、それ自体が触媒的に活性である材料の使用は、最終触媒の変換および/または選択性を変更し得ることが認識されることに留意すべきである。本明細書において、不活性材料は、本発明がアルキル化プロセスに利用され、および反応速度を制御するための他の手段を利用せずに経済的にかつ秩序的にアルキル化製品を得ることができる場合、変換の量を制御するための希釈剤として適切に役立ち得ることも認識される。これらの不活性材料は、商業的な作動条件下での触媒の粉砕強度を改善するため、および触媒のための結合剤またはマトリックスとして機能するために、天然由来のクレー、例えば、ベントナイトおよびカオリン中に組み込まれてよい。本明細書に記載される触媒は、複合化された形態で、約100部の支持体材料対約0部の結合剤材料、約99部の支持体材料対約1部の結合剤材料、約95部の支持体材料対約5部の結合剤材料の支持体材料対結合剤材料の比率を含むことができる。追加的にまたは代わりに、本明細書に記載の触媒は、典型的に、複合化された形態で、約90部の支持体材料対約10部の結合剤材料〜約10部の支持体材料対約90部の結合剤材料、約85部の支持体材料対約15部の結合剤材料〜約15部の支持体材料対約85部の結合剤材料、約80部の支持体材料対20部の結合剤材料〜20部の支持体材料対80部の結合剤材料の支持体材料対結合剤材料の比率を含むことができる。全ての比率は重量によるものであり、典型的に、80:20〜50:50、好ましくは65:35〜35:65の支持体材料:結合剤材料である。複合化は、材料を一緒に混練することを含む従来の手段により、およびそれに続いて所望の最終触媒粒子へとペレット化する押出成形により実行され得る。
いくつかの実施形態において、オルガノシリカ材料支持体は、網目構造に組み込まれたカチオン性金属部位をさらに含むことができる。そのようなカチオン性金属部位は、有機前駆体による表面への含浸もしくは錯化などのいずれかの好都合な方法により、またはいずれかの他の方法により組み込まれ得る。このようなオルガノ金属材料は、石油精製または石油化学製品製造において実行される多くの炭化水素分離において使用され得る。石油化学製品/燃料から望ましく分離される、そのような化合物の例としては、オレフィン、パラフィン、芳香族などを含むことができる。
別の実施形態において、芳香族飽和のための本明細書中に記載の水素化触媒を製造する方法が提供される。この方法は、
(a)構造指向剤および/またはポロゲンを本質的に含有しない水性混合物を供給すること(又は工程もしくはステップ)と、
(b)式[Z15Z16SiCH2]3(VII)
[式中、各Z15は、C1〜C4アルコキシ基であってもよく、各Z16は、C1〜C4アルコキシ基またはC1〜C4アルキル基であってもよい]
の少なくとも1種の化合物を水性混合物に添加して、溶液を形成すること(又は工程もしくはステップと、
(c)溶液をエイジング(又は老化)させて、プリプロダクト(又は半製品)を製造すること(又は工程もしくはステップ)と、
(d)プリプロダクト(又は半製品)を乾燥させて、本明細書に記載の式[Z1OZ2OSiCH2]3(I)のモノマーの独立単位を含むポリマーであるオルガノシリカ材料支持体を得ること(又は工程もしくはステップ)と、
(e)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属でオルガノシリカ材料支持体を含浸させること(又は工程もしくはステップ)と
を含む。
本明細書に記載のオルガノシリカ材料は、構造指向剤またはプロゲンを本質的に使用せずに製造され得る。したがって、水性混合物は、添加された構造指向剤および/または添加されたプロゲンを本質的に含有しない。
構造指向剤の例としては、限定されないが、非イオン性界面活性剤、イオン性界面活性剤、カチオン性界面活性剤、ケイ素界面活性剤、両性界面活性剤、ポリアルキレンオキシド界面活性剤、フルオロ界面活性剤、コロイド性結晶、ポリマー、ハイパー分枝状分子、星型分子、巨大分子、デンドリマーおよびそれらの組合せを含むことができる。追加的にまたは代わりに、表面指向剤は、ポロキサマー、トリブロックポリマー、テトラアルキルアンモニウム塩、非イオン性ポリオキシエチレンアルキル、ジェミニ界面活性剤、またはそれらの混合物を含むことができるか、またはそれらであり得る。テトラアルキルアンモニウム塩の例としては、限定されないが、セチルトリメチルアンモニウムクロリド(CTAC)、セチルトリメチルアンモニウムブロミド(CTAB)およびオクタデシルトリメチルアンモニウムクロリドなど、セチルトリメチルアンモニウムハライドを含むことができる。他の代表的な表面指向剤は、追加的にまたは代わりに、ヘキサデシルトリメチルアンモニウムクロリドおよび/またはセチルピリジニウムブロミドを含むことができる。
ポロゲン材料は、オルガノシリカ材料において、ドメイン、離散的領域、空隙および/または細孔を形成することができる。ポロゲンの例は、ブロックコポリマー(例えば、ジブロックポリマー)である。本明細書で使用される場合、ポロゲンとしては水を含まない。ポリマーポロゲンの例としては、限定されないが、ポリビニル芳香族、例えば、ポリスチレン、ポリビニルピリジン、水素化ポリビニル芳香族、ポリアクリロニトリル、ポリアルキレンオキシド、例えば、ポリエチレンオキシドおよびポリプロピレンオキシド、ポリエチレン、ポリ乳酸、ポリシロキサン、ポリカプロラクトン、ポリカプロラクタム、ポリウレタン、ポリメタクリレート、例えば、ポリメチルメタクリレートまたはポリメタクリルさん、ポリアクリレート、例えば、ポリメタクリレートおよびポリアクリル酸、ポリジエン、例えば、ポリブタジエンおよびポリイソプレン、ポリビニルクロリド、ポリアセタールおよびアミンキャップアルキレンオキシド、ならびにそれらの組合せを含むことができる。
種々の実施形態において、本明細書で提供される方法で使用される水性混合物は、塩基および/または酸を含むことができる。
本明細書で提供される方法は、各Z15がC1〜C4アルコキシ基であり得、各Z16がC1〜C4アルコキシ基またはC1〜C4アルキル基であり得る、式[Z15Z16SiCH2]3(VII)の少なくとも1種の化合物を水性混合物に添加して、溶液を形成するステップを含む。
追加的な実施形態において、本明細書で提供される方法は、水性溶液に、各Z17が、C1〜C6アルキル基であり得、Z18、Z19およびZ20が、それぞれ独立して、C1〜C6アルキル基、C1〜C6アルコキシ基、窒素含有C1〜C10アルキル基、窒素含有ヘテロアラルキル基、および窒素を含有する任意選択的に置換されたヘテロシクロアルキル基からなる群から選択され得る、式Z17OZ18Z19Z20Si(VIII)の化合物を添加して、本明細書に記載の式(I)の少なくとも1種の独立単位、本明細書に記載の式(III)の少なくとも1種の独立単位および任意選択的に本明細書に記載の式(II)の少なくとも1種の独立単位を含むコポリマーである、オルガノシリカ材料を得ること(又は工程もしくはステップ)をさらに含むことができる。
追加的な実施形態において、本明細書で提供される方法は、水性溶液に、各Z21が、独立して、C1〜C4アルコキシ基であり得、各Z22およびZ23が、独立して、C1〜C4アルコキシ基またはC1〜C4アルキル基であり得、各R1が、C1〜C8アルキレン基、C2〜C8アルケニレン基、C2〜C8アルキニレン基、窒素含有C2〜C10アルキレン基、任意選択的に置換されたC6〜C20アラルキル基、および任意選択的に置換されたC4〜C20ヘテロシクロアルキル基からなる群から選択され得る、式Z21Z22Z23Si−R1−SiZ21Z22Z23(IX)の化合物を添加して、本明細書に記載の式(I)の少なくとも1種の独立単位、本明細書に記載の式(IV)の少なくとも1種の独立単位および任意選択的に本明細書に記載の式(II)および/または(III)の少なくとも1種の独立単位を含むコポリマーである、オルガノシリカ材料を得ること(又は工程もしくはステップ)をさらに含むことができる。
追加的な実施形態において、本明細書で提供される方法は、水性溶液に三価金属酸化物の供給源を添加すること(又は工程もしくはステップ)を含むことができる。
追加的な実施形態において、本明細書で提供される方法は、水性溶液に金属キレート化合物の供給源を添加すること(又は工程もしくはステップ)をさらに含むことができる。
本明細書に記載の方法において、約99:1〜約1:99、約75:1〜約1:99、約50:1〜約1:99、約25:1〜約1:99、約15:1〜約1:99、約50:1〜約1:50、約25:1〜約1:25または約15:1〜約1:15の式(VII):式(VII)、式(VII):式(VIII)、式(VII):式(IX)、式(IX):式(VIII)、式(VII):式(X)および式(VII):式(XI)のモル比が使用されてよい。例えば、約3:2、約4:1、約4:3、約5:1、約2:3、約1:1約5:2および約15:1のモル比が使用されてよい。例えば、式(VII):式(VII)のモル比は、約3:2であり得る。式(VII):式(VIII)のモル比は、約2:3、約4:3、約4:1または約3:2であり得る。式(VII):式(IX)のモル比は、約2:3および約4:1であり得る。式(IX):式(VIII)のモル比は、約5:2、約1:1、約1:2または約2:3であり得る。式(VII):式(X)および式(VII):式(XI)のモル比は、約15:1または約5:1であり得る。
本明細書に記載の方法において形成された溶液は、少なくとも約4時間、少なくとも約6時間、少なくとも約12時間、少なくとも約18時間、少なくとも約24時間(1日)、少なくとも約30時間、少なくとも約36時間、少なくとも約42時間、少なくとも約48時間(2日)、少なくとも約54時間、少なくとも約60時間、少なくとも約66時間、少なくとも約72時間(3日)、少なくとも約96時間(4日)、少なくとも約120時間(5日)または少なくとも約144時間(6日)にわたり老化され得る。
本明細書に記載の方法は、プリプロダクト(又は半製品)(例えば、ゲル)を乾燥させて、オルガノシリカ材料支持体を製造すること(又は工程もしくはステップ)を含む。
追加的な実施形態において、本水素化触媒を製造する方法は、本明細書に記載される少なくとも1種の触媒金属でオルガノシリカ材料支持体を含浸させること(又は工程もしくはステップ)をさらに含むことができる。特に、少なくとも1種の触媒金属は、第6族元素、第8族元素、第9族元素、第10族元素またはそれらの組合せ、特に第8、9および/または10族金属(例えば、Pt、Pd、Ir、Rh、Osまたはそれらの組合せ)からなる群から選択され得る。別の好ましい実施形態において、金属水素化成分は、非貴金属の第VIII族金属と第VI族金属との組合せであり得る。適切な組合せとしては、Ni、CoまたはFeとMoまたはWとの組合せ、好ましくは、NiとMoまたはWとの組合せを含むことができる。オルガノシリカ材料支持体は、インシピエントウェットネスによって触媒金属で含浸されるか、またはイオン交換され得る。
追加的な実施形態において、本水素化触媒を製造する方法は、本明細書に記載される結合剤材料を添加すること(又は工程もしくはステップ)をさらに含むことができる。特に、結合剤材料は、活性および不活性材料、無機材料、クレー、アルミナ、シリカ、シリカ−アルミナ、チタニア、ジルコニアまたはそれらの組合せからなる群から選択されてよい。特に、結合剤は、シリカ−アルミナ、アルミナおよび/またはジルコニアあってよい。
追加的な実施形態において、本水素化触媒を製造する方法は、オルガノシリカ材料支持体の細孔内に組み込まれた、本明細書に記載される表面金属を添加すること(又は工程もしくはステップ)をさらに含むことができる。表面金属の添加は、触媒金属によるオルガノシリカ材料支持体の含浸より前に行うことができる。表面金属は、上記の通り、第1族元素、第2族元素、第13族元素およびそれらの組合せからなる群から選択することができる。追加的にまたは代わりに、表面金属の供給源は、本明細書に記載の式(X)および/または(XI)の化合物であってよい。特に、本明細書に記載の方法は、オルガノシリカ材料支持体の含浸の前に、オルガノシリカ材料支持体の表面上でアルミニウムをグラフト化させること(又は工程もしくはステップ)をさらに含むことができる。
いくつかの実施形態において、本方法は、シリカ材料を得るために、オルガノシリカ材料支持体を焼成すること(又は工程もしくはステップ)をさらに含むことができる。焼成は、空気、または窒素もしくは窒素が豊富な空気などの不活性気体中で実行することができる。焼成は、少なくとも約300℃、少なくとも約350℃、少なくとも約400℃、少なくとも約450℃、少なくとも約500℃、少なくとも約550℃、少なくとも約600℃または少なくとも約650℃、例えば、少なくとも約400℃の温度で実行可能である。追加的にまたは代わりに、焼成は、約300℃〜約650℃、約300℃〜約600℃、約300℃〜約550℃、約300℃〜約400℃、約300℃〜約450℃、約300℃〜約400℃、約300℃〜約350℃、約350℃〜約650℃、約350℃〜約600℃、約350℃〜約550℃、約350℃〜約400℃、約350℃〜約450℃、約350℃〜約400℃、約400℃〜約650℃、約400℃〜約600℃、約400℃〜約550℃、約400℃〜約500℃、約400℃〜約450℃、約450℃〜約650℃、約450℃〜約600℃、約450℃〜約550℃、約450℃〜約500℃、約500℃〜約650℃、約500℃〜約600℃、約500℃〜約550℃、約550℃〜約650℃、約550℃〜約600℃または約600℃〜約650℃の温度で実行可能である。
水素化触媒は、本明細書に記載の方法から製造することができる。別の特定の実施形態において、水素化触媒は、本明細書に記載のオルガノシリカ材料支持体を形成するために本明細書に記載の構造指向剤またはポロゲンを本質的に含有しない、本明細書に記載の水性混合物、および本明細書に記載の少なくとも1種の触媒金属から製造することができ、オルガノシリカ材料支持体は、
(i)本明細書に記載の式(I)の単位を含むホモポリマー;または
(ii)本明細書に記載の式(I)の独立単位と、本明細書に記載の式(II)、(III)、(IV)、(V)および/または(VI)の単位を含む少なくとも1種の他のモノマーとを含むコポリマー
であってよい。
種々の実施形態において、炭化水素供給流の芳香族水素化プロセスが本明細書に提供される。芳香族水素化プロセスは、芳香族含有量の減少した反応生成物を製造するために有効な芳香族水素化条件下で操作される第1の反応段階において、水素含有処理気体の存在下、芳香族を含む炭化水素供給流と、本明細書に記載の水素化触媒とを接触させること(又は工程もしくはステップ)を含むことができる。本明細書で理解されるように、水素化触媒は、供給流の水素化および芳香族飽和の両方のために使用され得る。同様に、水素化プロセスは、供給流の水素化または芳香族飽和を示すことができる。
本発明は、追加的にまたは代わりに、以下の実施形態の1つ以上を含むことができる。
(a)芳香族含有量が低下した反応生成物を製造するために有効な芳香族水素化条件下で操作される反応段階(又は反応ステージ)において、水素含有処理気体の存在下、芳香族を含む炭化水素供給流を水素化触媒と接触させること(又は工程もしくはステップ)を含み、前記水素化触媒が、
(i)式[Z1OZ2OSiCH2]3(I)
[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表す]
のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体と、
(ii)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属と
を含む、炭化水素供給流のための芳香族水素化プロセス(又は芳香族水素化工程もしくは芳香族水素化処理)。
各Z1およびZ2が、独立して、水素原子、C1〜C2アルキル基、または別のモノマーのケイ素原子への結合を表す、実施形態1のプロセス。
各Z1およびZ2が、独立して、水素原子、エチル、または別のモノマーのケイ素原子への結合を表す、実施形態1または2のプロセス。
前記オルガノシリカ材料支持体が、
(i)式[Z3OZ4SiCH2]3(II)
[式中、各Z3は、水素原子、C1〜C4アルキル基または別のモノマーのケイ素原子への結合を表し、各Z4は、C1〜C6アルキル基を表す]
の独立単位(independent unit)、
(ii)式Z5OZ6Z7Z8Si(III)
[式中、各Z5は、水素原子またはC1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表し、Z6、Z7およびZ8は、それぞれ独立して、ヒドロキシル基、C1〜C4アルキル基、C1〜C4アルコキシ基、窒素含有C1〜C10アルキル基、窒素含有ヘテロアルキル基、窒素を含有する任意選択的に置換されたヘテロシクロアルキル基および別のモノマーのケイ素原子に結合した酸素原子からなる群から選択される]
の独立単位、
(iii)式Z9Z10Z11Si−R−SiZ9Z10Z11(IV)
[式中、各Z9は、独立して、ヒドロキシル基、C1〜C4アルコキシ基、または別のコモノマーのケイ素原子に結合した酸素を表し、各Z10およびZ11は、独立して、ヒドロキシル基、C1〜C4アルコキシ基、C1〜C4アルキル基、または別のモノマーのケイ素原子に結合した酸素を表し、Rは、C1〜C8アルキレン基、C2〜C8アルケニレン基、C2〜C8アルキニレン基、窒素含有C1〜C10アルキレン基、任意選択的に置換されたC6〜C20アラルキルおよび任意選択的に置換されたC4〜C20ヘテロシクロアルキル基からなる群から選択される]
の独立単位、
(iv)式M1(OZ12)3(V)
[式中、M1は、第13族金属を表し、各Z12は、独立して、水素原子、C1〜C6アルキル、または別のモノマーのケイ素原子への結合を表す]
の独立単位、
(v)式(Z13O)2M2−O−Si(OZ14)3(VI)
[式中、M2は、第13族金属を表し、各Z13および各Z14は、独立して、水素原子、C1〜C6アルキル基、または別のモノマーのケイ素原子への結合を表す]
の独立単位、および
(vi)それらの組合せ
からなる群から選択される少なくとも1種の他のモノマーをさらに含む、上記実施形態のいずれか1つのプロセス。
式(II)の少なくとも1種の独立単位が存在し、前記式中、各Z3が、水素原子、C1〜C2アルキル基、または別のシロキサンモノマーのケイ素原子への結合を表し、各Z4が、C1〜C2アルキル基を表す、実施形態4のプロセス。
各Z3が、水素原子、エチル、または別のシロキサンモノマーのケイ素原子への結合を表し、各Z4が、メチルを表す、実施形態4または5のプロセス。
式(III)の少なくとも1種の独立単位が存在し、前記式中、各Z5が、水素原子、C1〜C2アルキル基、または別のコモノマーのケイ素原子への結合を表し、Z6、Z7およびZ8が、それぞれ独立して、ヒドロキシル基、C1〜C2アルキル基、C1〜C2アルコキシ基、窒素含有C3〜C10アルキル基、窒素含有C4〜C10ヘテロアルキル基、窒素を含有する任意選択的に置換されたC4〜C10ヘテロシクロアルキル基、および別のモノマーのケイ素原子に結合した酸素からなる群から選択される、実施形態4〜6のいずれか1つのプロセス。
Z6、Z7およびZ8が、それぞれ独立して、ヒドロキシル基、C1〜C2アルキル基、C1〜C2アルコキシ基、および別のモノマーのケイ素原子に結合した酸素からなる群から選択される、実施形態7のプロセス。
各Z5が、水素原子、メチル、エチル、または別のコモノマーのケイ素原子への結合を表し、Z6、Z7およびZ8が、それぞれ独立して、ヒドロキシル基、メチル、メトキシ、エトキシ、
式(IV)の少なくとも1種の独立単位が存在し、前記式中、各Z9が、ヒドロキシル基、C1〜C2アルコキシ基、または別のコモノマーのケイ素原子に結合した酸素を表し、各Z10およびZ11が、独立して、ヒドロキシル基、C1〜C2アルコキシ基、C1〜C2アルキル基、または別のモノマーのケイ素原子に結合した酸素を表し、Rが、C1〜C4アルキレン基、C2〜C4アルケニレン基、C2〜C4アルキニレン基、窒素含有C4〜C10アルキレン基、任意選択的に置換されたC6〜C10アラルキルおよび任意選択的に置換されたC4〜C12ヘテロシクロアルキル基からなる群から選択される、実施形態4〜9のいずれか1つのプロセス。
各Z9が、ヒドロキシル基、メトキシ、エトキシ、または別のコモノマーのケイ素原子に結合した酸素を表し、各Z10およびZ11が、それぞれ独立して、ヒドロキシル基、メトキシ、エトキシ、メチル、または別のモノマーのケイ素原子に結合した酸素を表し、Rが、−CH2−、−CH2CH2−、−HC=CH−、
式(V)の少なくとも1種の独立単位が存在し、前記式中、M1が、AlまたはBであり、各Z12が、水素原子、C1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表す、実施形態4〜11のいずれか1つのプロセス。
式(VI)の少なくとも1種の単位が存在し、前記式中、M2が、AlまたはBであり、各Z13および各Z14が、独立して、水素原子、C1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表す、実施形態4〜12のいずれか1つのプロセス。
前記オルガノシリカ材料支持体が、約500m2/g〜約2000m2/gの全表面積を有する、上記実施形態のいずれか1つのプロセス。
前記オルガノシリカ材料支持体が、約0.5cm3/g〜約3.0cm3/gの細孔体積(又はポアボリューム)を有する、上記実施形態のいずれか1つのプロセス。
前記オルガノシリカ材料支持体が、2.5nm〜5nmの平均細孔直径を有する、上記実施形態のいずれか1つのプロセス。
前記少なくとも1種の触媒金属が、Pt、Pd、Ir、Rh、Re、Ru、Osおよびそれらの組合せからなる群から選択される、上記実施形態のいずれか1つのプロセス。
前記少なくとも1種の触媒金属が、Pt、Pdおよびそれらの混合物からなる群から選択される、実施形態17のプロセス。
前記触媒金属が、約0.1〜約2.0重量%の範囲の量で存在する、上記実施形態のいずれか1つのプロセス。
前記水素化触媒が、活性材料および不活性材料、無機材料、クレー、アルミナ、シリカ、シリカ−アルミナ、チタニア、ジルコニア、酸化イットリウム、酸化タンタル、酸化ニオブ、活性炭、セラミックス、軽石、シーライトおよびそれらの組合せからなる群から選択される結合剤材料(又はバインダー材料)をさらに含む、上記実施形態のいずれか1つのプロセス。
前記結合剤材料が、シリカ−アルミナ、アルミナ、チタニア、ジルコニアおよび活性炭からなる群から選択される、実施形態20のプロセス。
前記炭化水素供給流が、炭化水素流体、ディーゼル沸騰範囲供給流、潤滑油沸騰範囲供給流、全石油原油もしくは減少石油原油(whole or reduced petroleum crude)、大気残留物(atmospheric residua)、真空残留物(vacuum residua)、プロパン脱アスファルト化残留物(propane deasphalted residua)、脱蝋油、スラックワックス、ラフィネートまたはそれらの混合物である、上記実施形態のいずれか1つのプロセス。
前記炭化水素供給流が、全て前記炭化水素供給流に基づき、0.2重量%までの窒素、3.0重量%までの硫黄および約50重量%までの芳香族を含有する、上記実施形態のいずれか1つのプロセス。
前記炭化水素供給流が、約100wppm未満の硫黄含有量を有する、上記実施形態のいずれか1つのプロセス。
前記有効な芳香族水素化条件が、約350℃以下の温度を含む、上記実施形態のいずれか1つのプロセス。
芳香族水素化のための水素化触媒を製造する方法であって、
(a)構造指向剤(structure directing agent)および/またはポロゲンを本質的に含有しない水性混合物(aqueous mixture)を供給すること(又は工程もしくはステップ)と、
(b)式[Z15Z16SiCH2]3(VII)
[式中、各Z15は、C1〜C4アルコキシ基を表し、各Z16は、C1〜C4アルコキシ基またはC1〜C4アルキル基を表す]
の少なくとも1種の化合物を前記水性混合物に添加して、溶液を形成すること(又は工程もしくはステップ)と、
(c)前記溶液をエイジング(又は老化)させて、プリプロダクト(又は半製品)を製造すること(又は工程もしくはステップ)と、
(d)前記プリプロダクトを乾燥させて、式[Z1OZ2OSiCH2]3(I)[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表す]のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体を得ること(又は工程もしくはステップ)と、
(e)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属で前記オルガノシリカ材料支持体を含浸させること(又は工程もしくはステップ)と
を含む方法。
各Z15が、C1〜C2アルコキシ基を表す、実施形態26の方法。
各Z16が、C1〜C4アルコキシ基を表す、実施形態26または27の方法。
各Z16が、C1〜C2アルコキシ基を表す、実施形態26〜28のいずれか1つの方法。
前記式(VII)の少なくとも1種の化合物が、1,1,3,3,5,5−ヘキサエトキシ−1,3,5−トリシラシクロヘキサンである、実施形態26〜29のいずれか1つの方法。
各Z1およびZ2が、独立して、水素原子、C1〜C2アルキル基、または別のモノマーのケイ素原子への結合を表す、実施形態26〜30のいずれか1つの方法。
各Z1およびZ2が、独立して、水素原子、エチル、または別のモノマーのケイ素原子に結合した酸素を表す、実施形態26〜31のいずれか1つの方法。
前記オルガノシリカ材料支持体を含浸する前に、前記オルガノシリカ材料支持体表面上でアルミニウムをグラフト化すること(又は工程もしくはステップ)をさらに含む、実施形態26〜32のいずれか1つの方法。
前記水性混合物に、
(i)式(VII)のさらなる化合物、
(ii)式Z17OZ18Z19Z20Si(VIII)
[式中、各Z17は、C1〜C6アルキル基を表し、Z18、Z19およびZ20は、それぞれ独立して、C1〜C6アルキル基、C1〜C6アルコキシ基、窒素含有C1〜C10アルキル基、窒素含有ヘテロアラルキル基および窒素を含有する任意選択的に置換されたヘテロシクロアルキル基からなる群から選択される]
の化合物、
(iii)式Z21Z22Z23Si−R1−SiZ21Z22Z23(IX)
[式中、各Z21は、独立して、C1〜C4アルコキシ基を表し、各Z22およびZ23は、独立して、C1〜C4アルコキシ基またはC1〜C4アルキル基を表し、R1は、C1〜C8アルキレン基、C2〜C8アルケニレン基、C2〜C8アルキニレン基、窒素含有C1〜C10アルキレン基、任意選択的に置換されたC6〜C20アラルキルおよび任意選択的に置換されたC4〜C20ヘテロシクロアルキル基からなる群から選択される]
の化合物、
(iv)三価金属酸化物の供給源、および
(v)それらの組合せ
からなる群から選択される少なくとも1種の化合物を添加すること(又は工程もしくはステップ)をさらに含む、実施形態26〜33のいずれか1つの方法。
前記少なくとも1種の化合物が、式(VII)のさらなる化合物であり、式中、各Z15は、C1〜C2アルコキシ基を表し、各Z16は、C1〜C2アルコキシ基またはC1〜C2アルキル基を表す、実施形態34の方法。
前記式(VII)の化合物が、1,3,5−トリメチル−1,3,5−トリエトキシ−1,3,5−トリシラシクロヘキサンである、実施形態35の方法。
前記少なくとも1種の化合物が、式(VII)の化合物であり、前記式中、各Z17は、C1〜C2アルキル基を表し、Z18、Z19およびZ20は、それぞれ独立して、C1〜C2アルキル基、C1〜C2アルコキシ基、窒素含有C3〜C10アルキル基、窒素含有C4〜C10ヘテロアラルキル基または窒素を含有する任意選択的に置換されたC4〜C10ヘテロシクロアルキル基からなる群から選択される、実施形態34〜36のいずれか1つの方法。
前記式(VIII)の化合物が、テトラエチルオルトシリケート、メチルトリエトキシシラン、(N,N−ジメチル−アミノプロピル)トリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリエトキシシラン、4−メチル−1−(3−トリエトキシシリルプロピル)−ピペラジン、4−(2−(トリエトキシシリル)エチル)ピリジン、1−(3−(トリエトキシシリル)プロピル)−4,5−ジヒドロ−1H−イミダゾールおよび(3−アミノプロピル)トリエトキシシランからなる群から選択される、実施形態37の方法。
前記少なくとも1種の化合物が、式(IX)の化合物であり、前記式中、各Z21は、C1〜C2アルコキシ基を表し、各Z22およびZ23は、独立して、C1〜C2アルコキシ基またはC1〜C2アルキル基を表し、R1は、C1〜C4アルキレン基、C2〜C4アルケニレン基、C2〜C4アルキニレン基および窒素含有C4〜C10アルキレン基からなる群から選択される、実施形態34〜38のいずれか1つの方法。
前記式(IX)の化合物が、1,2−ビス(メチルジエトキシシリル)エタン、ビス(トリエトキシシリル)メタン、1,2−ビス(トリエトキシシリル)エチレン、N,N’−ビス[(3−トリメトキシシリル)プロピル]エチレンジアミン、ビス[(メチルジエトキシシリル)プロピル]アミンおよびビス[(メチルジメトキシシリル)プロピル]−N−メチルアミンからなる群から選択される、実施形態39の方法。
前記少なくとも1種の化合物が、三価金属酸化物の供給源であり、三価金属酸化物の供給源が、
a.式M3(OZ24)3(X)
[式中、M3は、第13族金属を表し、各Z24は、独立して、C1〜C6アルキル基を表す]
の化合物、または
b.式(Z25O)2M4−O−Si(OZ26)3(XI)
[式中、M4は、第13族金属を表し、各Z25および各Z26は、独立して、C1〜C6アルキル基を表す]
の化合物
の少なくとも1種である、実施形態34〜40のいずれか1つの方法。
三価金属酸化物の供給源が、式(X)の化合物であり、前記式中、M3は、AlまたはBであり、各Z24は、C1〜C4アルキル基を表す、実施形態41の方法。
三価金属酸化物の供給源が、式(XI)の化合物であり、前記式中、M4は、AlまたはBであり、各Z25および各Z26は、独立して、C1〜C4アルキル基を表す、実施形態41または42の方法。
前記三価金属酸化物の供給源が、アルミニウムトリメトキシド、アルミニウムトリエトキシド、アルミニウムイソプロポキシドおよびアルミニウム−トリ−sec−ブトキシドからなる群から選択される、実施形態34〜43のいずれか1つの方法。
前記水性混合物が塩基を含み、約8〜約14のpHを有する、実施形態26〜44のいずれか1つの方法。
塩基が、アンモニウムヒドロキシド(又は水酸化アンモニウム)または金属ヒドロキシドである、実施形態45の方法。
水性混合物が酸を含み、約0.01〜約6.0のpHを有する、実施形態26〜44のいずれか1つの方法。
酸が、無機酸である、実施形態47の方法。
無機酸が、塩酸である、実施形態48の方法。
前記工程(c)において、前記溶液が、144時間までにわたり約50℃〜約200℃の温度でエイジング(又は老化)される、実施形態26〜49のいずれか1つの方法。
前記プリプロダクトが、約70℃〜約200℃の温度で乾燥される、実施形態26〜50のいずれか1つの方法。
前記少なくとも1種の触媒金属が、Pt、Pd、Ir、Rh、Re、Ru、Osおよびそれらの組合せからなる群から選択される、実施形態26〜51のいずれか1つの方法。
少なくとも1種の触媒金属が、Pt、Pdおよびそれらの混合物からなる群から選択される、実施形態52の方法。
活性材料および不活性材料、無機材料、クレー、アルミナ、シリカ、シリカ−アルミナ、チタニア、ジルコニア、酸化イットリウム、酸化タンタル、酸化ニオブ、活性炭、セラミックス、軽石、シーライトまたはそれらの組合せからなる群から選択される結合剤材料を添加すること(又は工程もしくはステップ)をさらに含む、実施形態26〜53のいずれか1つの方法。
前記結合剤材料が、シリカ−アルミナ、アルミナ、シリカ、チタニアおよびジルコニア 活性炭からなる群から選択される、実施形態54の方法。
実施形態26〜55のいずれか1つの方法に従って製造された水素化触媒。
(i)式[Z1OZ2OSiCH2]3(I)
[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表す]
のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体と、
(ii)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属と
を含む、芳香族水素化のための水素化触媒。
前記オルガノシリカ材料支持体が、
(i)式[Z3OZ4SiCH2]3(II)
[式中、各Z3は、水素原子、C1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表し、各Z4は、C1〜C6アルキル基を表す]
の独立単位、
(ii)式Z5OZ6Z7Z8Si(III)
[式中、各Z5は、水素原子またはC1〜C4アルキル基、または別のモノマーのケイ素原子への結合を表し、Z6、Z7およびZ8は、それぞれ独立して、ヒドロキシル基、C1〜C4アルキル基、C1〜C4アルコキシ基、窒素含有C1〜C10アルキル基、窒素含有ヘテロアルキル基、窒素を含有する任意選択的に置換されたヘテロシクロアルキル基および別のモノマーのケイ素原子に結合した酸素原子からなる群から選択される]
の独立単位、
(iii)式Z9Z10Z11Si−R−SiZ9Z10Z11(IV)
[式中、各Z9は、独立して、ヒドロキシル基、C1〜C4アルコキシ基、または別のコモノマーのケイ素原子に結合した酸素を表し、各Z10およびZ11は、独立して、ヒドロキシル基、C1〜C4アルコキシ基、C1〜C4アルキル基、または別のモノマーのケイ素原子に結合した酸素を表し、Rは、C1〜C8アルキレン基、C2〜C8アルケニレン基、C2〜C8アルキニレン基、窒素含有C1〜C10アルキレン基、任意選択的に置換されたC6〜C20アラルキルおよび任意選択的に置換されたC4〜C20ヘテロシクロアルキル基からなる群から選択される]
の独立単位、
(iv)式M1(OZ12)3(V)
[式中、M1は、第13族金属を表し、各Z12は、独立して、水素原子、C1〜C6アルキル、または別のモノマーのケイ素原子への結合を表す]
の独立単位、
(v)式(Z13O)2M2−O−Si(OZ14)3(VI)
[式中、M2は、第13族金属を表し、各Z13および各Z14は、独立して、水素原子、C1〜C6アルキル基、または別のモノマーのケイ素原子への結合を表す]
の独立単位、および
(vi)それらの組合せ
からなる群から選択される少なくとも1種の他のモノマーをさらに含む、実施形態57の水素化触媒。
アルミニウムが、オルガノシリカ材料支持体表面上にグラフト化されている、実施形態57または58の水素化触媒。
小角X線回折分析
エックス線粉末回折(XRD)パターンは、低角度測定用アクセサリーを備えたPANalytical X’pert回折計上で収集した。XRD分析は、0.0167°のステップサイズおよび1.2秒の集計時間で、0.5〜10°の2θ範囲内のCuKa(=1.5405980Å)を使用して記録した。
29Si MAS NMRスペクトルは、それぞれ、79.4MHzおよび99.2MHzの29Siラーモア回転数に相当するVarian InfinityPlus−400分光計(9.4Tで操作)およびVarian InfinityPlus−500(11.74Tで操作)上で、5kHzのスピニング、4.0μsの90°パルスおよび少なくとも60秒のリサイクル遅延を使用して、7.5mmのMASプローブヘッドを用いて、プロトンがデータ取得中に非干渉化するという状態で記録された。29Si化学シフトは、外部テトラメチルシラン(δSi=0.0ppm)に関して参照される。13C CPMAS NMRスペクトルは、125MHzの13Cラーモア回転数に相当するVarian InfinityPlus−500分光計上で、40kHzのスピニング、少なくとも1m秒の1H−13C直交偏波(CP)接触時間、少なくとも1秒のリサイクル遅延を使用して、1.6mmのMASプローブヘッドを用いて、プロトンがデータ取得中に非干渉化するという状態で記録された。13C化学シフトは、外部テトラメチルシラン(δC=0.0ppm)に関して参照される。27Al MAS NMRスペクトルは、130.1MHzの27Alラーモア回転数に相当するVarian InfinityPlus−500上で、12kHzのスピニング、π/12ラジアンパルス長さおよび0.3秒のリサイクル遅延を使用して、4mmのMASプローブヘッドを用いて、プロトンがデータ取得中に非干渉化するという状態で記録された。化学シフトは、Al(H2O)6 3+(δAl=0.0ppm)の外部溶液に関して参照される。全てのNMRスペクトルは、スピニング用空気を使用して室温で記録された。
熱安定性結果は、Q5000 TGA上で記録された。ランプレートは5℃/分であり、温度範囲は25℃〜800℃でであった。全ての試料は、空気および窒素の両方で試験された。
Quantchrom autosorb iQ2を用いて作業を行った。異なる温度におけるCO2等温線を収集する前に、全ての試料を3時間、真空中で120℃において前処理した。
窒素吸着/脱着分析は、種々の道具、例えば、TriStar 3000、TriStar II 3020およびAutosorb−1で実行した。N2等温線を収集する前、全ての試料は、4時間、真空中で120℃において前処理した。分析プログラムによって実験データを計算し、およびBET表面積(全表面積)、ミクロポーラス表面積(S)、全細孔体積、ミクロ細孔の細孔体積、平均細孔直径(または半径)などを報告する。
オルガノシリカ材料支持体
31.5gの30% NH4OHおよび39.6gの脱イオン水(DI)の溶液を製造した。この溶液のpHは12.55であった。この溶液に、20gの1,1,3,3,5,5−ヘキサエトキシ−1,3,5−トリシラシクロヘキサン([(EtO)2SiCH2]3)を添加して、
1.0[(EtO)2SiCH2]3:21 OH:270 H2O
のモル組成を有する混合物を製造し、これを1日、室温(20〜25℃)で攪拌した。この溶液をオートクレーブに移し、80〜90℃で1日老化させ、ゲルを製造した。ゲルを真空中80℃で乾燥させ、ほとんどの水を除去し、次いで、120℃で一晩(16〜24時間)完全に乾燥させた。これにより、透明固体としてオルガノシリカ材料支持体が得られ、およびそれは、粉砕後、白色粉末に変換された。この調製では、表面指向剤またはプロゲンは使用されなかった。
0.141gのAl(O−i−Pr)3を30mlの無水トルエン中に溶解し、および6gのオルガノシリカ材料支持体を添加して溶液を形成した。溶液を1日(16〜24時間)、110℃で攪拌した。固体を遠心分離によって収集し、次いで、トルエンおよびメタノールで洗浄した。収集した固体を120℃で真空下、オーブン中で乾燥させ、Al−オルガノシリカ材料支持体を形成した。
Al−オルガノシリカ材料支持体を、アルミナ結合剤および水と混合し、押出成形した。押出成形は、湿潤しているか、または部分的に乾燥された材料上で実行可能である。適切な触媒は、400〜2メッシュサイズ(Tylerスケール)に適合する粒径を有する、粉末、顆粒、または成形製品の形態であり得る。表面積の損失を防ぐため、押出物を不活性雰囲気(例えば、N2)下で約400℃において焼成し、焼成された押出物を得た。
焼成された押出物は、インシピエントウェットネスによってPdおよびPt塩で含浸され、触媒1が製造された。金属塩分は、押出成形の前に、支持体+結合剤+水溶液中に添加することができる。金属は、混合および押出成形の前に、支持体に含浸することもできる。含浸された材料は、N2雰囲気下で焼成され、化学吸着によって定義される良好な金属分散をもたらす温度において、金属塩を分解することができる。例えば、分散助剤が使用される場合、焼成は必要ではない。
窒素吸着/脱着分析は触媒1において実行され、および結果を表1に示す。
触媒1の芳香族飽和活性は、高スループット実験試験ユニットにおいて、以下の表2に記載される石油化学供給物において試験された。
Claims (17)
- (a)芳香族含有量が低下した反応生成物を製造するために有効な芳香族水素化条件下で操作される反応段階において、水素含有処理気体の存在下、芳香族を含む炭化水素供給流を水素化触媒と接触させることを含み、前記水素化触媒が、
(i)式[Z1OZ2OSiCH2]3(I)
[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基またはケイ素原子への結合を表す]
のモノマーの独立単位を含むポリマーであるオルガノシリカ材料支持体と、
(ii)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属と
を含み、
アルミニウムが、オルガノシリカ材料支持体表面上にグラフト化されている、
炭化水素供給流のための芳香族水素化プロセス。 - 各Z1およびZ2が、独立して、水素原子、エチル、またはケイ素原子への結合を表す、請求項1に記載のプロセス。
- (i)前記オルガノシリカ材料支持体が、500m2/g〜2000m2/gの全表面積を有すること、
(ii)前記オルガノシリカ材料支持体が、0.5cm3/g〜3.0cm3/gの細孔体積を有すること、および
(iii)前記オルガノシリカ材料支持体が、2.5nm〜5nmの平均細孔直径を有すること
の1つ以上が満たされる、請求項1又は2に記載のプロセス。 - 前記少なくとも1種の触媒金属が、Pt、Pd、Ir、Rh、Re、Ru、Osおよびそれらの組合せからなる群から選択され、前記少なくとも1種の触媒金属が、0.1〜2.0重量%の範囲の量で存在する、請求項1〜3のいずれか1項に記載のプロセス。
- 前記水素化触媒が、活性材料および不活性材料、無機材料、クレー、アルミナ、シリカ、シリカ−アルミナ、チタニア、ジルコニア、酸化イットリウム、酸化タンタル、酸化ニオブ、活性炭、セラミックス、軽石、シーライトおよびそれらの組合せからなる群から選択される結合剤材料をさらに含む、請求項1〜4のいずれか1項に記載のプロセス。
- (i)前記炭化水素供給流が、炭化水素流体、ディーゼル沸騰範囲供給流、潤滑油沸騰範囲供給流、全石油原油もしくは減少石油原油、大気残留物、真空残留物、プロパン脱アスファルト化残留物、脱蝋油、スラックワックス、ラフィネートまたはそれらの混合物であること、
(ii)前記炭化水素供給流が、全て前記炭化水素供給流に基づき、0.2重量%までの窒素、3.0重量%までの硫黄および50重量%までの芳香族を含有すること、および
(iii)前記炭化水素供給流が、100wppm未満の硫黄含有量を有すること
の1つ以上が満たされる、請求項1〜5のいずれか1項に記載のプロセス。 - 前記有効な芳香族水素化条件が、350℃以下の温度を含む、請求項1〜6のいずれか1項に記載のプロセス。
- 芳香族水素化のための水素化触媒を製造する方法であって、
(a)構造指向剤および/またはポロゲンを本質的に含有しない水性混合物を供給することと、
(b)式[Z15Z16SiCH2]3(VII)
[式中、各Z15は、C1〜C4アルコキシ基を表し、各Z16は、C1〜C4アルコキシ基またはC1〜C4アルキル基を表す]
の少なくとも1種の化合物を前記水性混合物に添加して、溶液を形成することと、
(c)前記溶液をエイジングさせて、プリプロダクトを製造することと、
(d)前記プリプロダクトを乾燥させて、式[Z1OZ2OSiCH2]3(I)
[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基、またはケイ素原子への結合を表す]
のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体を得ることと、
(e)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属で前記オルガノシリカ材料支持体を含浸させることと
を含み、
前記オルガノシリカ材料支持体を含浸する前に、前記オルガノシリカ材料支持体表面上でアルミニウムをグラフト化することをさらに含む、
方法。 - 前記式(VII)の少なくとも1種の化合物が、1,1,3,3,5,5−ヘキサエトキシ−1,3,5−トリシラシクロヘキサンであり、前記式中、各Z1およびZ2が、独立して、水素原子、エチル、またはケイ素原子に結合した酸素を表す、請求項8に記載の方法。
- 前記水性混合物が、アンモニウムヒドロキシドまたは金属ヒドロキシドなどの塩基を含み、8〜14のpHを有する、請求項8又は9に記載の方法。
- 前記水性混合物が、塩酸などの酸を含み、0.01〜6.0のpHを有する、請求項8又は9に記載の方法。
- 前記工程(c)において、前記溶液が、144時間までにわたり50℃〜200℃の温度でエイジングされる、請求項8〜11のいずれか1項に記載の方法。
- 前記プリプロダクトが、70℃〜200℃の温度で乾燥される、請求項8〜12のいずれか1項に記載の方法。
- 前記少なくとも1種の触媒金属が、Pt、Pd、Ir、Rh、Re、Ru、Osおよびそれらの組合せからなる群から選択される、請求項8〜13のいずれか1項に記載の方法。
- 活性材料および不活性材料、無機材料、クレー、アルミナ、シリカ、シリカ−アルミナ、チタニア、ジルコニア、酸化イットリウム、酸化タンタル、酸化ニオブ、活性炭、セラミックス、軽石、シーライトおよびそれらの組合せからなる群から選択される結合剤材料を添加することをさらに含む、請求項8〜14のいずれか1項に記載の方法。
- 前記結合剤材料が、シリカ−アルミナ、アルミナ、シリカ、チタニアおよびジルコニア 活性炭からなる群から選択される、請求項15に記載の方法。
- (i)式[Z1OZ2OSiCH2]3(I)
[式中、各Z1およびZ2は、独立して、水素原子、C1〜C4アルキル基、またはケイ素原子への結合を表す]
のモノマーの独立単位を含むポリマーである、オルガノシリカ材料支持体と、
(ii)第8族金属、第9族金属、第10族金属およびそれらの組合せからなる群から選択される少なくとも1種の触媒金属と
を含み、
アルミニウムが、オルガノシリカ材料支持体表面上にグラフト化されている、
芳香族水素化のための水素化触媒。
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- 2015-12-11 US US15/526,512 patent/US10239967B2/en not_active Expired - Fee Related
- 2015-12-11 EP EP15828704.5A patent/EP3230409A1/en not_active Withdrawn
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JP2018501227A (ja) | 2018-01-18 |
CA2964969C (en) | 2022-11-15 |
SG11201702452UA (en) | 2017-06-29 |
EP3230325A1 (en) | 2017-10-18 |
DK3230410T3 (da) | 2019-07-01 |
CN107001945A (zh) | 2017-08-01 |
SG11201702538PA (en) | 2017-06-29 |
US20160229959A1 (en) | 2016-08-11 |
SG11201702541XA (en) | 2017-06-29 |
CA2964385C (en) | 2021-06-01 |
US20170320971A1 (en) | 2017-11-09 |
US10544239B2 (en) | 2020-01-28 |
EP3229944A1 (en) | 2017-10-18 |
EP3230410A1 (en) | 2017-10-18 |
EP3230410B1 (en) | 2019-04-10 |
CN107001945B (zh) | 2020-12-18 |
CA2964409A1 (en) | 2016-06-16 |
EP3230409A1 (en) | 2017-10-18 |
US10239967B2 (en) | 2019-03-26 |
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