JP6688406B2 - 高選択性促進輸送膜およびオレフィン/パラフィン分離のためのその使用 - Google Patents
高選択性促進輸送膜およびオレフィン/パラフィン分離のためのその使用 Download PDFInfo
- Publication number
- JP6688406B2 JP6688406B2 JP2018561934A JP2018561934A JP6688406B2 JP 6688406 B2 JP6688406 B2 JP 6688406B2 JP 2018561934 A JP2018561934 A JP 2018561934A JP 2018561934 A JP2018561934 A JP 2018561934A JP 6688406 B2 JP6688406 B2 JP 6688406B2
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- hydrophilic polymer
- membrane
- support membrane
- hydrophilic
- nanoporous support
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Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Description
本出願は、2016年6月9日に提出された米国特許出願第62/348112号に対する優先権を主張するものであり、すべての記載内容が本明細書に参考として組み込まれる。
以下の実施例は、本発明の1つ以上の好ましい実施形態を説明するために提供されるが、それらの実施形態に限定されるわけではない。本発明の範囲内の以下の実施例には多くの変形形態が可能である。
UFTM−1促進輸送膜
プロピレン/プロパン選択性の高い促進輸送膜(UFTM−1)は、支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーを含む相対的に親水性の微細孔のナノ多孔性支持膜および硝酸銀を含浸した該膜の表面に被覆された他の親水性ポリマーから作製した。非対称の相対的に親水性の微細孔ナノ多孔性ポリエーテルスルホン支持膜は、相反転法によって作製した。重量%換算で、ポリエーテルスルホン(BASF社E6020P)18〜25%、N−メチルピロリドン60〜65%、1,3−ジオキソラン10〜15%、グリセリン1〜10%、n−デカン0.5〜2%を含む膜キャスティング液を、ナイロン繊維上にキャストし、10分間1℃の水浴中に浸漬することによってゲル化させ、次いで、5分間85℃の湯浴中で熱処理した。アルギン酸ナトリウムの希釈水溶液を、非対称の相対的に親水性の微細孔ナノ多孔性ポリエーテルスルホン含浸支持膜の表面にニップ法によって塗布した。前記膜スキン層表面の微細なナノ細孔内部にアルギン酸ナトリウムを含む含浸膜に、希釈した酢酸水溶液中にキトサンを溶解させた溶液を塗布し、次いで、50℃で乾燥し、前記膜表面に無孔性のキトサン薄層を形成した。次いで、前記膜を塩基性の水酸化ナトリウム溶液で処理し、水で洗浄し、前記膜スキン層表面に微細なナノ細孔内部のアルギン酸と、前記膜表面に無孔性のキトサン薄層とを含むポリエーテルスルホン支持膜を形成した。次いで、前記膜を硝酸銀水溶液(H2O中に3M)に含浸した。次いで、前記含浸膜を、50℃、791kPa(100psig)下で、加湿した(相対湿度80〜100%)プロピレン/プロパン(C3=/C3)ガス混合物(70%C3=/30%C3)によって試験した。UFTM−1の性能は、表1に示される。UFTM−1は、3時間の試験後、99.9%を超えるプロピレン純度の浸透流に対して39.8GPUのプロピレン透過性および1000を超えるプロピレン/プロパン選択性を示した。UFTM−1膜を、さらに、33%C3=と残りがC3の供給流によって試験し、その結果を前記供給流中に70%のプロピレンを有するものと比較した。比較結果を表2に示す。UFTM−1膜は、33%C3=と残りがC3の供給流で非常に高いプロピレン透過性を示し、より低いプロピレン/プロパン選択性を示した。
COMP−FTM−1促進輸送膜
アルギン酸ナトリウムのニップ溶液を塗布しない以外は実施例1と同じ方法で促進輸送膜(COMP−FTM−1)を作製した。前記ポリエーテルスルホン支持膜のスキン層表面の微細なナノ細孔内部にアルギン酸を含まない場合、COMP−FTM−1膜は、3時間の試験後、45.3GPUのプロピレン透過性と67.6の低いプロピレン/プロパン選択性を示し、この選択性は時間の経過とともに減少し続けた。
UFTM−2促進輸送膜
キトサンコーティング層にキトサンのニップ溶液を追加で塗布した以外は、実施例1と同じ方法で促進輸送膜(UFTM−2)を作製した。前記膜では、3時間の試験後、プロピレン/プロパン選択性が152、透過性はUFTM−1と類似した39.6GPUを示した。
UFTM−3促進輸送膜
アルギン酸ナトリウム溶液を支持膜表面の塗布に使用し、その後アルギン酸ナトリウムでニップした以外は実施例1と同じ方法で促進輸送膜(UFTM−3)を作製した。このアルギン酸ナトリウム塗布膜を、希釈した酢酸溶液で処理し、水で洗浄し、硝酸銀に含浸した。
COMP−FTM−2促進輸送膜
市販のミクロ細孔の限外ろ過ポリスルホン支持膜(DSS社GR51PP)に希釈した酢酸水溶液中にキトサンを溶解させた溶液を塗布し、次いで室温で乾燥した。次いで、前記膜を塩基性の水酸化ナトリウム溶液で処理し、水で洗浄し、硝酸銀水溶液(H2O中に3M)に含浸した。次いで、前記含浸COMP−FTM−2膜を、50℃、791kPa(100psig)下で、加湿した(相対湿度80〜100%)プロピレン/プロパン(C3=/C3)ガス混合物(70%C3=)によって試験した。UFTM−1との比較結果を表3に示す。前記ミクロ細孔のポリスルホン支持膜に作製された膜は、1GPU未満と言う非常に低い透過性を示し、透過速度が低かったために選択性を測定できなかった。
膜スキン層表面の細孔内部に親水性ポリマーを含まない(すなわち、ニップ法によって細孔中に親水性ポリマーが導入されていない)COMP−FTM−1およびCOMP−FTM−2促進輸送膜は、時間の経過とともに前記細孔から銀担体が損失し、プロピレン透過性およびプロピレン/プロパン選択性が徐々に悪くなる一方で、本発明に記載された非対称の相対的に親水性の微細孔ナノ多孔性ポリエーテルスルホン支持膜の膜スキン層表面の微細なナノ細孔内部のアルギン酸、前記膜表面の無孔性のキトサン薄層、およびキトサンコーティング層と微細なナノ細孔内部のアルギン酸ポリマーに導入された硝酸銀(I)を含むUFTM−1促進輸送膜は、120時間を超える安定性を示し、プロピレン生成物のプロピレン透過性も純度も目立った低下が見られなかった。99.7%を超えるプロプレン純度が、35GPU超のプロピレン透過性を持つ浸透流で維持された。時間を軸とした浸透流のプロピレン透過性および純度のプロット図を図1に示す。
特定の実施形態について以下に記載するが、当然のことだが、本説明は例示を目的としており、前述の説明および添付の特許請求の範囲を限定するものではない。
Claims (5)
- 99〜1モル%の1種以上のC2〜C8オレフィン類および1〜99モル%の1種以上のC1〜C8パラフィン類を含む気体状の供給流の処理方法であって、
親水性の微細孔のナノ多孔性支持膜、前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマー、前記ナノ多孔性支持膜表面に被覆された無孔性の親水性ポリマー薄層、および前記ナノ多孔性支持膜の表面に被覆された親水性ポリマー層と前記微細なナノ細孔内部の親水性ポリマーに導入された金属塩を含む促進輸送膜の供給側に前記気体状の供給流を送り、これにより前記供給流中の80モル%以上のオレフィンが前記膜を通過するようにすること、及び、
90モル%以上のオレフィンおよび10モル%以下のパラフィンを含む浸透流を回収すること、を含み、
前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーが前記ナノ多孔性支持膜の表面に被覆された無孔性の親水性ポリマー薄層と異なり、
前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーがアルギン酸であり、前記ナノ多孔性支持膜の表面に被覆された無孔性の親水性ポリマー薄層の親水性ポリマーがキトサンまたはヒアルロン酸である、
方法。 - 親水性の微細孔のナノ多孔性支持膜、前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマー、前記ナノ多孔性支持膜表面に被覆された無孔性の親水性ポリマー薄層、及び、前記ナノ多孔性支持膜の表面に被覆された親水性ポリマー層と前記微細なナノ細孔内部の親水性ポリマーに導入された金属塩、を含み、
前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーが前記ナノ多孔性支持膜の表面に被覆された無孔性の親水性ポリマー薄層と異なり、
前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーがアルギン酸であり、前記ナノ多孔性支持膜の表面に被覆された無孔性の親水性ポリマー薄層の親水性ポリマーがキトサンまたはヒアルロン酸である、
促進輸送膜。 - 前記ナノ多孔性支持膜が、ポリエーテルスルホン、ポリエーテルスルホンとポリイミドのブレンド、酢酸セルロース、三酢酸セルロース、および酢酸セルロースと三酢酸セルロースのブレンドからなる群から選択される親水性のポリマーを含む、請求項2に記載の膜。
- 前記ナノ多孔性支持膜の表面に被覆された親水性ポリマー層と前記微細なナノ細孔内部の親水性ポリマーに導入された金属塩が、銀塩類または銅塩類である、請求項2に記載の膜。
- 親水性の微細孔のナノ多孔性支持膜、前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマー、前記ナノ多孔性支持膜表面に被覆された無孔性の親水性ポリマー薄層、及び、前記ナノ多孔性支持膜の表面に被覆された親水性ポリマー層と前記微細なナノ細孔内部の親水性ポリマーに導入された金属塩を含む促進輸送膜の作製方法であって、該方法は、
(a)相反転膜キャスティングプロセスまたは紡糸作製プロセスにより、前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部に親水性ポリマーを含む親水性の微細孔のナノ多孔性支持膜を作製すること、ここで、前記親水性ポリマーは、相反転膜キャスティングプロセスまたは紡糸作製プロセス中またはそれらプロセスの終わりに、前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部に導入される、
(b)前記ナノ多孔性支持膜のスキン層表面に無孔性の親水性ポリマー薄層を塗布すること、及び
(c)前記ナノ多孔性支持膜のスキン層表面の無孔性の親水性ポリマー薄層を金属塩水溶液に浸漬することによって前記促進輸送膜を作製すること、
を含み、
前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーが前記ナノ多孔性支持膜の表面に被覆された無孔性の親水性ポリマー薄層と異なり、
前記ナノ多孔性支持膜のスキン層表面の微細なナノ細孔内部の親水性ポリマーがアルギン酸であり、前記ナノ多孔性支持膜の表面に被覆された無孔性の親水性ポリマー薄層の親水性ポリマーがキトサンまたはヒアルロン酸である、
方法。
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Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10471381B2 (en) | 2016-06-09 | 2019-11-12 | Uop Llc | High selectivity facilitated transport membranes and their use for olefin/paraffin separations |
US10328386B2 (en) | 2017-05-18 | 2019-06-25 | Uop Llc | Co-cast thin film composite flat sheet membranes for gas separations and olefin/paraffin separations |
US10569233B2 (en) * | 2017-06-06 | 2020-02-25 | Uop Llc | High permeance and high selectivity facilitated transport membranes for olefin/paraffin separations |
US10751670B2 (en) | 2017-08-24 | 2020-08-25 | Uop Llc | High selectivity facilitated transport membrane comprising polyethersulfone/polyethylene oxide-polysilsesquioxane blend membrane for olefin/paraffin separations |
US10683246B2 (en) * | 2017-09-30 | 2020-06-16 | Uop Llc | Method and system for light olefin separation |
US10427997B2 (en) | 2017-12-27 | 2019-10-01 | Uop Llc | Modular membrane system and method for olefin separation |
US10507405B1 (en) * | 2018-06-29 | 2019-12-17 | Uop Llc | Process for separation of propylene from a liquefied petroleum gas stream |
US11083992B2 (en) * | 2018-09-27 | 2021-08-10 | Uop Llc | Methods of making high selectivity facilitated transport membranes, high selectivity facilitated transport membrane elements and modules |
EP3866952A4 (en) * | 2018-10-19 | 2022-07-13 | Imtex Membranes Corp. | GAS PERMEATION PROCESS THROUGH A RETICULATED MEMBRANE |
JP2022505412A (ja) * | 2018-10-19 | 2022-01-14 | イムテックス メンブレインズ コーポレイション | マルチモジュールシステム中の膜への液体材料の補給 |
CN111111477B (zh) * | 2018-11-01 | 2021-04-13 | 中国科学院过程工程研究所 | 一种烯烃/烷烃分离膜及其制备方法 |
US11471839B2 (en) * | 2019-08-06 | 2022-10-18 | Uop Llc | High selectivity membranes for hydrogen sulfide and carbon dioxide removal from natural gas |
US11447436B2 (en) * | 2020-06-30 | 2022-09-20 | Uop Llc | Method and system to control and maintain product quality for an olefin membrane separation |
US20220134292A1 (en) * | 2020-11-04 | 2022-05-05 | Uop Llc | Ionically conductive thin film composite membranes for energy storage applications |
WO2023022847A1 (en) | 2021-08-19 | 2023-02-23 | Exxonmobil Chemical Patents Inc. | Membrane-based separation processes enhanced with an absorption device |
Family Cites Families (75)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL271831A (ja) | 1960-11-29 | |||
US3758603A (en) | 1972-05-12 | 1973-09-11 | Standard Oil Co | Process for separation of unsaturated hydrocarbons |
GB1431946A (en) * | 1972-05-12 | 1976-04-14 | Standard Oil Co | Process for separation of unsaturated hydrocarbons |
CA2040798A1 (en) | 1990-05-25 | 1991-11-26 | Dean T. Tsou | Facilitated liquid membranes for olefin/paraffin gas separations and related process |
US5198316A (en) | 1990-08-17 | 1993-03-30 | Ciba-Geigy Corporation | Copolyimides, their preparation and the use thereof |
US5256295A (en) | 1990-12-28 | 1993-10-26 | Membrane Technology & Research | Two-stage membrane process and apparatus |
US5670051A (en) | 1996-05-23 | 1997-09-23 | Membrane Technology And Research, Inc. | Olefin separation membrane and process |
CA2402841C (en) | 2000-03-22 | 2009-11-24 | Victrex Manufacturing Limited | Ion exchange materials |
US6339182B1 (en) * | 2000-06-20 | 2002-01-15 | Chevron U.S.A. Inc. | Separation of olefins from paraffins using ionic liquid solutions |
US6896796B2 (en) | 2001-02-16 | 2005-05-24 | W. R. Grace & Co.-Conn. | Membrane separation for sulfur reduction |
KR100444325B1 (ko) | 2001-07-16 | 2004-08-16 | 한국과학기술연구원 | 안정성이 향상된 은염이 함유된 올레핀 촉진수송 고분자 분리막 및 이의 제조방법 |
JP3996390B2 (ja) | 2001-12-26 | 2007-10-24 | 住友ゴム工業株式会社 | タイヤの成形金型、及びそれによって製造された空気入りタイヤ |
EP1375459A1 (en) | 2002-06-28 | 2004-01-02 | Nederlandse Organisatie voor toegepast-natuurwetenschappelijk Onderzoek TNO | Separation of unsaturated hydrocarbons from a fluid mixture |
CA2426629C (en) | 2003-04-25 | 2012-09-25 | Nova Chemicals Corporation | Process for the separation of olefins from paraffins using membranes |
US20080063917A1 (en) | 2003-07-31 | 2008-03-13 | Masahiro Yamashita | Electrolyte Membrane-Electrode Assembly, Fuel Cell Using The Same, And Method For Producing Electrolyte Membrane-Electrode Assembly |
US7604746B2 (en) | 2004-04-27 | 2009-10-20 | Mcmaster University | Pervaporation composite membranes |
BRPI0516161A (pt) * | 2004-09-30 | 2008-08-26 | Univ Mcmaster | material compósito, e, aparelho de filtração |
KR100709190B1 (ko) | 2005-08-31 | 2007-04-18 | 삼성에스디아이 주식회사 | 연료 전지용 막-전극 어셈블리 및 이를 포함하는 연료 전지시스템 |
KR100717745B1 (ko) | 2005-10-06 | 2007-05-11 | 삼성에스디아이 주식회사 | 연료전지용 바인더, 이를 이용한 촉매층 형성용 조성물, 및 이를 이용한 연료전지용 막-전극 어셈블리와 이의 제조방법 |
KR100813242B1 (ko) | 2006-02-14 | 2008-03-13 | 삼성에스디아이 주식회사 | 고분자 전해질막, 이의 제조 방법 및 이를 구비한 연료전지 |
US7803275B2 (en) | 2006-07-14 | 2010-09-28 | Exxonmobil Research And Engineering Company | Membrane separation process using mixed vapor-liquid feed |
KR20080020259A (ko) | 2006-08-31 | 2008-03-05 | 삼성에스디아이 주식회사 | 연료 전지용 막-전극 어셈블리, 이의 제조방법 및 이를포함하는 연료 전지 시스템 |
AU2008209499A1 (en) * | 2007-01-24 | 2008-07-31 | Whatman Inc. | Modified porous membranes, methods of membrane pore modification, and methods of use thereof |
US20090071334A1 (en) | 2007-06-22 | 2009-03-19 | Aspen Systems, Inc. | Convenient Substance-Recovery System and Process |
US20090277837A1 (en) | 2008-05-06 | 2009-11-12 | Chunqing Liu | Fluoropolymer Coated Membranes |
US20100018926A1 (en) | 2008-06-25 | 2010-01-28 | Chunqing Liu | Mixed Matrix Membranes Containing Ion-Exchanged Molecular Sieves |
CN102131568B (zh) | 2008-06-30 | 2014-02-12 | 3M创新有限公司 | 形成可再润湿非对称膜的方法和可再润湿非对称膜 |
WO2010002501A2 (en) | 2008-06-30 | 2010-01-07 | 3M Innovative Properties Company | Method of forming an asymmetric membrane |
US8337598B2 (en) | 2008-09-05 | 2012-12-25 | Honeywell International Inc. | Photo-crosslinked gas selective membranes as part of thin film composite hollow fiber membranes |
US8114191B2 (en) | 2008-12-11 | 2012-02-14 | General Electric Company | Energy efficient approach to CO2 capture process |
US8561812B2 (en) | 2009-03-27 | 2013-10-22 | Uop Llc | Blend polymer membranes comprising thermally rearranged polymers derived from aromatic polyimides containing ortho-positioned functional groups |
US8444749B2 (en) | 2009-06-10 | 2013-05-21 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Method and system for membrane-based gas recovery |
CN101612527B (zh) * | 2009-07-21 | 2011-11-30 | 清华大学 | 一种对聚合物多孔膜表面及膜孔表面进行修饰的方法 |
CN102770197B (zh) | 2009-12-28 | 2015-07-01 | 可乐丽股份有限公司 | 荷电镶嵌多层膜及其制造方法 |
US8366804B2 (en) | 2010-05-28 | 2013-02-05 | Uop Llc | High permeance polyimide membranes for air separation |
US9216390B2 (en) | 2010-07-15 | 2015-12-22 | Ohio State Innovation Foundation | Systems, compositions, and methods for fluid purification |
WO2012036550A1 (en) | 2010-09-13 | 2012-03-22 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Antimicrobial membrane containing silver nanoparticles |
EP2661317B1 (en) | 2011-01-04 | 2021-11-17 | The Research Foundation for The State University of New York | Functionalization of nanofibrous microfiltration membranes for water purification |
RU2465951C1 (ru) * | 2011-03-01 | 2012-11-10 | Закрытое Акционерное Общество "Аквафор Продакшн" (Зао "Аквафор Продакшн") | Композиционный материал для фильтрационной очистки жидкости |
US8912288B2 (en) | 2011-06-17 | 2014-12-16 | Uop Llc | Separation process using a polyimide membrane |
EP2545985A1 (en) | 2011-07-15 | 2013-01-16 | Gambro Lundia AB | Composite membrane |
JP2013075264A (ja) | 2011-09-30 | 2013-04-25 | Fujifilm Corp | ガス分離膜、その製造方法、それを用いたガス分離膜モジュール |
KR101361704B1 (ko) | 2012-03-08 | 2014-02-11 | 한국과학기술연구원 | 수처리용 분리막 및 그 제조 방법 |
WO2013136336A1 (en) | 2012-03-15 | 2013-09-19 | Advanced Mem-Tech Ltd. | Enhancement of membrane robustness by treatment with ionic materials |
US9017451B2 (en) | 2012-03-16 | 2015-04-28 | Membrane Technology And Research, Inc. | Membrane-based gas separation process using ejector-driven gas recycle |
WO2013165866A1 (en) | 2012-05-01 | 2013-11-07 | Dow Global Technologies Llc | A hollow fiber carbon molecular sieve membrane and preparation and use thereof |
US8829059B2 (en) | 2012-06-27 | 2014-09-09 | Membrane Technology And Research, Inc. | Processes for the production of methanol using sweep-based membrane separation steps |
US20140137734A1 (en) | 2012-11-20 | 2014-05-22 | Uop Llc | Cross-linked polyimide membranes for separations |
US20140290478A1 (en) | 2013-03-27 | 2014-10-02 | Uop Llc | High performance cross-linked polyimide asymmetric flat sheet membranes |
US9126154B2 (en) | 2013-06-28 | 2015-09-08 | Uop Llc | High hydrocarbon resistant chemically cross-linked aromatic polyimide membrane for separations |
CN104275094A (zh) | 2013-07-08 | 2015-01-14 | 南京理工大学 | 季铵盐壳聚糖htcc/聚醚砜复合纳滤膜及其制备 |
WO2015009969A1 (en) | 2013-07-18 | 2015-01-22 | Cms Technologies Holdings, Inc. | Membrane separation of olefin and paraffin mixtures |
US9211508B2 (en) | 2013-09-27 | 2015-12-15 | Uop Llc | Polybenzoxazole membranes from self-cross-linkable aromatic polyimide membranes |
US9126152B2 (en) | 2013-09-27 | 2015-09-08 | Uop Llc | Polybenzoxazole membranes from self-cross-linkable aromatic polyimide membranes |
US9126156B2 (en) | 2013-09-27 | 2015-09-08 | Uop Llc | Self cross-linkable and self cross-linked aromatic polyimide membranes for separations |
EP3055052A2 (en) | 2013-10-07 | 2016-08-17 | Praxair Technology Inc. | Ceramic oxygen transport membrane array reactor and reforming method |
JP6067649B2 (ja) * | 2013-12-26 | 2017-01-25 | 富士フイルム株式会社 | 酸性ガス分離モジュール |
EP3089813B1 (en) | 2013-12-30 | 2019-03-27 | 3M Innovative Properties Company | Use of an asymmetric composite membrane for pervaporation and cartridge comprising said membrane |
KR101561503B1 (ko) * | 2014-01-29 | 2015-10-20 | 충남대학교산학협력단 | 다공성 박막의 제조방법 및 그로부터 제조되는 수처리용 여과막 |
CN103894073A (zh) * | 2014-04-21 | 2014-07-02 | 哈尔滨工业大学 | 一种利用稀溶液界面聚合行为的多孔滤膜亲水化改性方法 |
EP3197591A1 (en) | 2014-09-26 | 2017-08-02 | 3M Innovative Properties Company | Separation modules, systems, and methods |
KR101695793B1 (ko) | 2014-10-21 | 2017-01-23 | 한국과학기술연구원 | 사다리형 폴리실세스퀴옥산을 이용한 기체분리막 및 그 제조방법 |
US9327248B1 (en) * | 2014-12-04 | 2016-05-03 | Uop Llc | Copolyimide membranes with high permeability and selectivity for olefin/paraffin separations |
US9567436B2 (en) | 2014-12-17 | 2017-02-14 | Uop Llc | Super high selectivity aromatic block copolyimide membranes for separations |
US10478778B2 (en) | 2015-07-01 | 2019-11-19 | 3M Innovative Properties Company | Composite membranes with improved performance and/or durability and methods of use |
CN105195026B (zh) * | 2015-07-17 | 2017-10-27 | 南京佳乐净膜科技有限公司 | 有机/无机杂化亲水改性中空纤维聚合物膜及其制备方法 |
US10471381B2 (en) | 2016-06-09 | 2019-11-12 | Uop Llc | High selectivity facilitated transport membranes and their use for olefin/paraffin separations |
US10258929B2 (en) * | 2016-06-30 | 2019-04-16 | Uop Llc | Stable facilitated transport membranes for olefin/paraffin separations |
US10322382B2 (en) | 2016-06-30 | 2019-06-18 | Uop Llc | High performance facilitated transport membranes for olefin/paraffin separations |
US10328386B2 (en) | 2017-05-18 | 2019-06-25 | Uop Llc | Co-cast thin film composite flat sheet membranes for gas separations and olefin/paraffin separations |
US10569233B2 (en) | 2017-06-06 | 2020-02-25 | Uop Llc | High permeance and high selectivity facilitated transport membranes for olefin/paraffin separations |
EP3428142A1 (en) * | 2017-07-14 | 2019-01-16 | Basf Se | Process for separating paraffins and olefins |
US10751670B2 (en) | 2017-08-24 | 2020-08-25 | Uop Llc | High selectivity facilitated transport membrane comprising polyethersulfone/polyethylene oxide-polysilsesquioxane blend membrane for olefin/paraffin separations |
US10683246B2 (en) * | 2017-09-30 | 2020-06-16 | Uop Llc | Method and system for light olefin separation |
US10427997B2 (en) * | 2017-12-27 | 2019-10-01 | Uop Llc | Modular membrane system and method for olefin separation |
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US10471381B2 (en) | 2019-11-12 |
SA518390116B1 (ar) | 2022-01-24 |
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