JPWO2020046768A5 - - Google Patents
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- JPWO2020046768A5 JPWO2020046768A5 JP2021510794A JP2021510794A JPWO2020046768A5 JP WO2020046768 A5 JPWO2020046768 A5 JP WO2020046768A5 JP 2021510794 A JP2021510794 A JP 2021510794A JP 2021510794 A JP2021510794 A JP 2021510794A JP WO2020046768 A5 JPWO2020046768 A5 JP WO2020046768A5
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- metal
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- organic framework
- liquid stream
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- 239000007788 liquid Substances 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000001768 cations Chemical class 0.000 claims description 14
- 150000004706 metal oxides Chemical class 0.000 claims description 14
- QCWXUUIWCKQGHC-UHFFFAOYSA-N zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052726 zirconium Inorganic materials 0.000 claims description 12
- 230000000536 complexating Effects 0.000 claims description 10
- 241000894007 species Species 0.000 claims description 9
- 239000011324 bead Substances 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 6
- 239000004743 Polypropylene Substances 0.000 claims description 5
- -1 polypropylene Polymers 0.000 claims description 5
- 229920001155 polypropylene Polymers 0.000 claims description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- 239000001116 FEMA 4028 Substances 0.000 claims description 2
- PYPQFOINVKFSJD-UHFFFAOYSA-N S[S] Chemical compound S[S] PYPQFOINVKFSJD-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 238000000231 atomic layer deposition Methods 0.000 claims description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 2
- 229960004853 betadex Drugs 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- CNRZQDQNVUKEJG-UHFFFAOYSA-N oxo-bis(oxoalumanyloxy)titanium Chemical compound O=[Al]O[Ti](=O)O[Al]=O CNRZQDQNVUKEJG-UHFFFAOYSA-N 0.000 claims description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N β-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 101700059654 KAT8 Proteins 0.000 description 11
- 206010028154 Multi-organ failure Diseases 0.000 description 11
- 101700059482 mof Proteins 0.000 description 11
- 239000002245 particle Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
Description
例えば、支持構造上にＭＯＦを配置することにより、処理される所与の液体をＭＯＦに効率的に接触させて、除去される化学種のＭＯＦによる取込みを可能にする能力が得られる。ＭＯＦによる、ポリプロピレンビーズなどの不活性ビーズのコーティングは、ＭＯＦと、ビーズが展開している任意の液体流との間での、高度な表面積接触を可能にする。したがって、ポリプロピレンビーズの表面にＭＯＦを配置することにより、液体流がＭＯＦ構造を通して濾過されるときにＭＯＦ粒子が液体流中の化合物と結合する能力が得られる。さらに、ポリプロピレンビーズなどのＭＯＦコーティング付き不活性構造の使用は、他のＭＯＦ粒子から離れる対流なしに、ＭＯＦと流動する液体流との液体接触を可能にする。
本発明の実施形態において、例えば以下の項目が提供される。
（項目１）
液相オキシアニオンおよび液相カチオンの両方と錯体化するための化合物であって、前記化合物は、式Ｒ
１
－ＳＯ
２
－Ｓ－Ｒ
２
－ＳＨを有する化合物を含み、式中、Ｒ
１
は、ジルコニウムベースの金属有機構造体を含み、Ｒ
２
はアルキルを含む、化合物。
（項目２）
前記ジルコニウムベースの金属有機構造体が、有機リンカーに結合されたペンダントベンジル基を含む、項目１に記載の化合物。
（項目３）
液体流からのオキシアニオンおよびカチオンの濃度を低減させるための方法であって、前記方法が、
オキシアニオンおよびカチオンを含む液体流を、式Ｒ
１
－ＳＯ
２
－Ｓ－Ｒ
２
－ＳＨ（式中、Ｒ
１
は、有機リンカーに結合されたペンダント基を有する、ジルコニウムベースの金属有機構造体を含み、Ｒ
２
はアルキルを含む）を有する化合物と接触させるステップ、
前記オキシアニオンと、前記ジルコニウムベースの金属有機構造体とを錯体化し、それによって、前記液体流中の前記オキシアニオンの濃度を低減させるステップ、ならびに
前記カチオンと前記化合物とを錯体化し、それによって、前記液体流中の前記カチオンの濃度を低減させるステップ
を含む、方法。
（項目４）
前記ペンダント基がペンダントベンジル基を含み、前記オキシアニオンと前記ジルコニウムベースの金属有機構造体とを錯体化する前記ステップが、前記オキシアニオンと、前記ジルコニウムベースの金属有機構造体のノードとを錯体化することを含み、前記カチオンと前記化合物とを錯体化する前記ステップが、前記カチオンと、前記化合物のチオ－スルホニル部分のメルカプト－硫黄および前記化合物の末端メルカプタンとを錯体化して、環状幾何形状を形成することを含む、項目３に記載の方法。
（項目５）
金属有機構造体を基材に結合するための方法であって、前記方法は、
金属酸化物を基材の表面に結合させるステップ、
前記基材と、流体からの少なくとも１つの種およびセチル－トリメチルアンモニウムブロミドを除去することが可能な金属有機構造体とを接触させ、それによって、前記金属有機構造体を前記基材に結合して、金属有機構造体－基材を生成するステップ
を含む、方法。
（項目６）
結合させる前記ステップが、
原子層堆積を使用して前記金属酸化物を前記基材の前記表面に結合させることを含み、前記金属酸化物が、酸化アルミニウム、酸化チタン、酸化亜鉛、およびこれらの組合せからなる群から選択される、項目５に記載の方法。
（項目７）
前記金属有機構造体がＮＵ－１０００を含む、項目５に記載の方法。
（項目８）
前記基材が不活性ポリプロピレンビーズを含む、項目５に記載の方法。
（項目９）
前記基材が巨視的ファブリックを含む、項目５に記載の方法。
（項目１０）
前記基材が分子状ファブリックを含む、項目５に記載の方法。
（項目１１）
少なくとも１つの化合物を液体流から除去するために、基材に結合された複数の金属有機構造体を利用するための方法であって、前記方法は、
複数の金属酸化物構造体を含む基材を、液体流から除去される１つの液体種を含む前記液体流に接触するように位置決めするステップであって、前記複数の金属酸化物構造体が、セチル－トリメチルアンモニウムブロミドまたはベータ－シクロデキストリンを介して前記基材に結合される、ステップ
前記液体流と、前記複数の金属酸化物構造体を含む前記基材とを接触させるステップ、
前記１つの液体種の少なくとも一部を、前記複数の金属酸化物構造体に結合させ、それによって前記液体から前記１つの液体種の前記一部を除去するステップ
を含む、方法。
For example, placing the MOF on a support structure provides the ability to efficiently contact a given liquid to be processed with the MOF to allow uptake by the MOF of species to be removed. Coating inert beads, such as polypropylene beads, with MOFs allows a high degree of surface area contact between the MOFs and any liquid stream in which the beads are developing. Thus, placing MOFs on the surface of polypropylene beads provides the ability of MOF particles to bind compounds in a liquid stream as the liquid stream is filtered through the MOF structure. Additionally, the use of MOF-coated inert structures, such as polypropylene beads, allows liquid contact between the MOF and the flowing liquid stream without convection away from other MOF particles.
In embodiments of the present invention, for example, the following items are provided.
(Item 1)
Compounds for complexing both liquid phase oxyanions and liquid phase cations, said compounds comprising compounds having the formula R 1 —SO 2 —S—R 2 —SH, wherein R 1 is , comprising a zirconium-based metal-organic framework, wherein R 2 comprises an alkyl.
(Item 2)
The compound of item 1, wherein said zirconium-based metal-organic framework comprises pendant benzyl groups attached to an organic linker.
(Item 3)
A method for reducing the concentration of oxyanions and cations from a liquid stream, said method comprising:
A liquid stream containing oxyanions and cations is prepared according to the formula R 1 —SO 2 —S—R 2 —SH, where R 1 is a zirconium-based metal-organic framework having pendant groups attached to an organic linker. wherein R 2 comprises alkyl;
complexing the oxyanion with the zirconium-based metal-organic framework, thereby reducing the concentration of the oxyanion in the liquid stream;
complexing said cations with said compound, thereby reducing the concentration of said cations in said liquid stream;
A method, including
(Item 4)
wherein said pendant group comprises a pendant benzyl group, and said step of complexing said oxyanion with said zirconium-based metal-organic framework complexes said oxyanion with a node of said zirconium-based metal-organic framework; wherein said step of complexing said cation with said compound complexes said cation with a mercapto-sulfur of the thio-sulfonyl moiety of said compound and a terminal mercaptan of said compound to form a cyclic geometry 4. The method of item 3, comprising forming.
(Item 5)
A method for bonding a metal-organic framework to a substrate, the method comprising:
bonding the metal oxide to the surface of the substrate;
contacting the substrate with a metal-organic framework capable of removing at least one species and cetyl-trimethylammonium bromide from a fluid, thereby bonding the metal-organic framework to the substrate; , producing a metal-organic framework-substrate
A method, including
(Item 6)
the step of combining
bonding the metal oxide to the surface of the substrate using atomic layer deposition, wherein the metal oxide is selected from the group consisting of aluminum oxide, titanium oxide, zinc oxide, and combinations thereof. 6. The method of item 5.
(Item 7)
6. The method of item 5, wherein the metal-organic framework comprises NU-1000.
(Item 8)
6. The method of item 5, wherein the substrate comprises inert polypropylene beads.
(Item 9)
6. The method of item 5, wherein the substrate comprises a macroscopic fabric.
(Item 10)
6. The method of item 5, wherein the substrate comprises a molecular fabric.
(Item 11)
A method for utilizing a plurality of metal-organic frameworks bonded to a substrate to remove at least one compound from a liquid stream, said method comprising:
positioning a substrate comprising a plurality of metal oxide structures in contact with the liquid stream comprising one liquid species to be removed from the liquid stream, the plurality of metal oxide structures comprising: attached to said substrate via cetyl-trimethylammonium bromide or beta-cyclodextrin;
contacting the liquid stream with the substrate comprising the plurality of metal oxide structures;
binding at least a portion of said one liquid species to said plurality of metal oxide structures, thereby removing said portion of said one liquid species from said liquid;
A method, including
Claims (16)
オキシアニオンおよびカチオンを含む液体流を、式Ｒ１－ＳＯ２－Ｓ－Ｒ２－ＳＨ（式中、Ｒ１は、有機リンカーに結合されたペンダント基を有する、ジルコニウムベースの金属有機構造体を含み、Ｒ２はアルキルを含む）を有する化合物と接触させるステップ、
前記オキシアニオンと、前記ジルコニウムベースの金属有機構造体とを錯体化し、それによって、前記液体流中の前記オキシアニオンの濃度を低減させるステップ、ならびに
前記カチオンと前記化合物とを錯体化し、それによって、前記液体流中の前記カチオンの濃度を低減させるステップ
を含む、方法。 A method for reducing the concentration of oxyanions and cations from a liquid stream, said method comprising:
A liquid stream containing oxyanions and cations is prepared according to the formula R 1 —SO 2 —S—R 2 —SH, where R 1 is a zirconium-based metal-organic framework having pendant groups attached to an organic linker. wherein R 2 comprises alkyl;
complexing the oxyanion with the zirconium-based metal-organic framework, thereby reducing the concentration of the oxyanion in the liquid stream; and complexing the cation with the compound, thereby A method comprising reducing the concentration of said cations in said liquid stream.
金属酸化物を基材の表面に結合させるステップ、
前記基材と、流体からの少なくとも１つの種およびセチル－トリメチルアンモニウムブロミドを除去することが可能な金属有機構造体とを接触させ、それによって、前記金属有機構造体を前記基材に結合して、金属有機構造体－基材を生成するステップ
を含む、方法。 A method for bonding a metal-organic framework to a substrate, the method comprising:
bonding the metal oxide to the surface of the substrate;
contacting the substrate with a metal-organic framework capable of removing at least one species and cetyl-trimethylammonium bromide from a fluid, thereby bonding the metal-organic framework to the substrate; , a method comprising producing a metal-organic framework-substrate.
原子層堆積を使用して前記金属酸化物を前記基材の前記表面に結合させることを含み、前記金属酸化物が、酸化アルミニウム、酸化チタン、酸化亜鉛、およびこれらの組合せからなる群から選択される、請求項５に記載の方法。 the step of combining
bonding the metal oxide to the surface of the substrate using atomic layer deposition, wherein the metal oxide is selected from the group consisting of aluminum oxide, titanium oxide, zinc oxide, and combinations thereof. 6. The method of claim 5, wherein
複数の金属酸化物構造体を含む基材を、液体流から除去される１つの液体種を含む前記液体流に接触するように位置決めするステップであって、前記複数の金属酸化物構造体が、セチル－トリメチルアンモニウムブロミドまたはベータ－シクロデキストリンを介して前記基材に結合される、ステップ
前記液体流と、前記複数の金属酸化物構造体を含む前記基材とを接触させるステップ、
前記１つの液体種の少なくとも一部を、前記複数の金属酸化物構造体に結合させ、それによって前記液体から前記１つの液体種の前記一部を除去するステップ
を含む、方法。 A method for utilizing a plurality of metal-organic frameworks bonded to a substrate to remove at least one compound from a liquid stream, said method comprising:
positioning a substrate comprising a plurality of metal oxide structures in contact with the liquid stream comprising one liquid species to be removed from the liquid stream, the plurality of metal oxide structures comprising: contacting the liquid stream with the substrate comprising the plurality of metal oxide structures, bound to the substrate via cetyl-trimethylammonium bromide or beta-cyclodextrin;
binding at least a portion of said one liquid species to said plurality of metal oxide structures, thereby removing said portion of said one liquid species from said liquid.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862723121P | 2018-08-27 | 2018-08-27 | |
| US62/723,121 | 2018-08-27 | ||
| US201862751646P | 2018-10-28 | 2018-10-28 | |
| US62/751,646 | 2018-10-28 | ||
| PCT/US2019/048051 WO2020046768A1 (en) | 2018-08-27 | 2019-08-25 | Metal-organic frameworks for the removal of multiple liquid phase compounds and methods for using and making same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021536451A JP2021536451A (en) | 2021-12-27 |
| JPWO2020046768A5 true JPWO2020046768A5 (en) | 2022-08-12 |
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| JP2021510794A Pending JP2021536451A (en) | 2018-08-27 | 2019-08-25 | Metal-organic frameworks for removing multiple liquid phase compounds and methods for using and making them |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US11168006B2 (en) |
| EP (1) | EP3843877A4 (en) |
| JP (1) | JP2021536451A (en) |
| KR (1) | KR20210044879A (en) |
| CN (2) | CN117282416A (en) |
| WO (1) | WO2020046768A1 (en) |
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| JP2018502704A (en) | 2014-12-12 | 2018-02-01 | エクソンモービル リサーチ アンド エンジニアリング カンパニーＥｘｘｏｎ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｅｎｇｉｎｅｅｒｉｎｇ Ｃｏｍｐａｎｙ | Coating method using organosilica material and use thereof |
| US10723635B2 (en) * | 2015-04-11 | 2020-07-28 | Northwestern University | Metal-organic frameworks for adsorption of liquid phase compounds |
| US10308527B2 (en) | 2015-04-11 | 2019-06-04 | Northwestern University | Metal-organic frameworks for adsorption of liquid phase compounds |
| CN104892656A (en) * | 2015-06-16 | 2015-09-09 | 广东工业大学 | Metal-organic framework material and synthetic method thereof |
| CN105175295B (en) * | 2015-09-24 | 2017-09-26 | 南昌航空大学 | A kind of preparation of mercapto-functionalized MOFs materials and its application of Adsorption Heavy Metals in Waters ion |
| WO2017184991A1 (en) * | 2016-04-22 | 2017-10-26 | The Regents Of The University Of California | Post-synthetically modified metal-organic frameworks for selective binding of heavy metal ions in water |
| CN106268652B (en) * | 2016-08-29 | 2019-08-30 | 张少强 | A kind of preparation method of the heavy metal chelating agent based on MOFs |
| JP2020508297A (en) | 2017-02-21 | 2020-03-19 | ノヴム スペロ リミテッドＮｏｖｕｍ Ｓｐｅｒｏ Ｌｔｄ． | New polyiminoketoaldehyde |
| EP3843877A4 (en) * | 2018-08-27 | 2022-08-24 | Electric Power Research Institute, Inc. | Metal-organic frameworks for the removal of multiple liquid phase compounds and methods for using and making same |
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2019
- 2019-08-25 EP EP19856031.0A patent/EP3843877A4/en active Pending
- 2019-08-25 WO PCT/US2019/048051 patent/WO2020046768A1/en unknown
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- 2019-08-25 KR KR1020217008893A patent/KR20210044879A/en active Search and Examination
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2021
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