JP2020531249A - 二酸化炭素回収のために環状ジアミンを付加した金属有機骨格 - Google Patents
二酸化炭素回収のために環状ジアミンを付加した金属有機骨格 Download PDFInfo
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- JP2020531249A JP2020531249A JP2020505866A JP2020505866A JP2020531249A JP 2020531249 A JP2020531249 A JP 2020531249A JP 2020505866 A JP2020505866 A JP 2020505866A JP 2020505866 A JP2020505866 A JP 2020505866A JP 2020531249 A JP2020531249 A JP 2020531249A
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims description 14
- 239000012621 metal-organic framework Substances 0.000 title claims description 11
- 239000001569 carbon dioxide Substances 0.000 title claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims description 7
- -1 cyclic diamine Chemical class 0.000 title abstract description 52
- 238000001179 sorption measurement Methods 0.000 claims abstract description 124
- 239000003463 adsorbent Substances 0.000 claims abstract description 49
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 36
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000004985 diamines Chemical group 0.000 claims abstract description 27
- 239000003546 flue gas Substances 0.000 claims abstract description 27
- 238000003795 desorption Methods 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 36
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 23
- 239000003446 ligand Substances 0.000 claims description 21
- 229910021645 metal ion Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims description 10
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- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000304 alkynyl group Chemical group 0.000 claims description 3
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
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- RHPBLLCTOLJFPH-UHFFFAOYSA-N piperidin-2-ylmethanamine Chemical compound NCC1CCCCN1 RHPBLLCTOLJFPH-UHFFFAOYSA-N 0.000 abstract description 3
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- 239000011777 magnesium Substances 0.000 description 51
- 125000001424 substituent group Chemical group 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 21
- 238000002474 experimental method Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 16
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- 125000005647 linker group Chemical group 0.000 description 13
- 238000011084 recovery Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000004404 heteroalkyl group Chemical group 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 150000002390 heteroarenes Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 description 5
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- 238000011068 loading method Methods 0.000 description 5
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- 230000000670 limiting effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical group [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- 238000002411 thermogravimetry Methods 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 230000004913 activation Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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Abstract
Description
本出願は、2017年8月4日に出願された米国仮特許出願第62/541,616号、名称「Metal−Organic Frameworks Appended with Cyclic Diamines for CO2 Capture」に対する優先権を主張するものであり、参照により本明細書に組み込まれる。
ジアミン2−(アミノメチル)ピペリジン(2−ampd)を金属有機骨格Mg2(dobpdc)(dobpdc4−=4,4´−ジオキシドビフェニル−3,3´−ジカルボキシレート、Mg2(dotpdc)(dotpdc4−=4,4´´−ジオキシド−[1,1´:4´,1´´−テルフェニル]−3,3´´−ジカルボキシレート)、またはMg2(pc−dobpdc)(pc−dobpdc4−=ジオキシドビフェニル−4,4´−ジカルボキシレートの開いたMg2+部位に付加することで、それぞれ、天然ガス火力発電所の煙道排出物からCO2を回収するための有望な吸着剤EMM−44、EMM−45、およびEMM−46を生成する(図1)。この吸着剤には、天然ガス火力発電所からの炭素回収に有望となる多数の特徴が存在する。
置換基が、左から右に書かれたそれらの従来の化学式によって明記される場合、その構造は、任意選択的に、右から左へ構造を書くことによって生じることになる化学的に同一の置換基も包含し、例えば、−CH2O−は、任意選択的に−OCH2−とも列挙することが意図される。
本開示の一態様は、吸着材料を提供する。吸着材料は、複数の金属イオンおよび複数のポリトピック有機リンカーを備える金属有機骨格を備える。複数のポリトピック有機リンカーにおける各ポリトピック有機リンカーは、複数の金属イオンにおける少なくとも2つの金属イオンに接続されている。吸着材料は、複数の配位子をさらに備える。複数の配位子における各それぞれの配位子は、金属有機骨格の複数の金属イオンにおける金属イオンにアミン付加される。複数の配位子における各それぞれの配位子は、下式を有し、
本開示の一態様では、開示された吸着材料に関するいくつかの技術用途を提供する。
本明細書に記載した実施例および実施形態は、単に例示を目的とし、それを踏まえた様々な修正または変更が当業者に示唆され、本出願の趣旨および権限ならびに添付の特許請求の範囲内に含まれることが理解される。本明細書で引用したすべての刊行物、特許、および特許出願は、あらゆる目的のためにそれらの全体が参照により本明細書に組み込まれる。
Claims (26)
- 吸着材料であって、
複数の金属イオンおよび複数のポリトピック有機リンカーを含む金属有機骨格であって、前記複数のポリトピック有機リンカーにおける各ポリトピック有機リンカーが、前記複数の金属イオンにおける少なくとも2つの金属イオンに接続されている、金属有機骨格と、
複数の配位子であって、前記複数の配位子における各それぞれの配位子が、前記金属有機骨格の前記複数の金属イオンにおける金属イオンにアミン付加され、前記複数の配位子における各それぞれの配位子が、下式を有し、
Xが、前記金属有機骨格の前記複数の金属イオンにおける金属イオンであり、
Zが、炭素、ケイ素、ゲルマニウム、硫黄、またはセレニウムであり、
R1、R2、R3、R4、R5、R6、R7、R8、R9、およびR10が各々独立して、H、ハロゲン、メチル、ハロゲン置換メチル、およびヒドロキシルから選択される、複数の配位子と、を含む、吸着材料。 - 前記複数の金属イオンにおける各金属イオン(X)が、Mg、Ca、Mn、Cr、Fe、Co、Ni、Cu、またはZnである、請求項1に記載の吸着材料。
- R1、R2、R3、R4、R5、R6、R7、R8、R9、およびR10が各々、水素である、請求項1または2の吸着材料。
- Zが、炭素である、請求項1〜3のいずれか一項に記載の吸着材料。
- 前記複数の金属イオンにおける各金属イオン(X)が、Mgである、請求項1〜4のいずれか一項に記載の吸着材料。
- 前記ポリトピック有機リンカーが、4,4´−ジオキシドビフェニル−3,3´−ジカルボキシレート(dobpdc4−)である、請求項1〜5のいずれか一項に記載の吸着材料。
- 前記ポリトピック有機リンカーが、4,4´´−ジオキシド−[1,1´:4´,1´´−テルフェニル]−3,3´´−ジカルボキシレート(dotpdc4−)である、請求項1〜5のいずれか一項に記載の吸着材料。
- 前記ポリトピック有機リンカーが、ジオキシドビフェニル−4,4´−ジカルボキシレート(パラ−カルボキシレート−dobpdc4−、pc−dobpdc4−とも称される)である、請求項1〜5のいずれか一項に記載の吸着材料。
- 前記吸着材料が、CO2吸着時に複数のCO2吸着ステップを示す、請求項1〜8のいずれか一項に記載の吸着材料。
- 前記吸着材料が、CO2脱着時に複数のCO2脱着ステップを示す、請求項1〜8のいずれか一項に記載の吸着材料。
- 前記吸着材料が、CO2吸着時に単一のCO2吸着ステップを示す、請求項1〜8のいずれか一項に記載の吸着材料。
- 前記吸着材料が、CO2脱着時に単一のCO2脱着ステップを示す、請求項1〜8のいずれか一項に記載の吸着材料。
- R1、R2、R3、R4、R5、R6、R7、R8、R9、およびR10が各々、水素であり、
Zが、炭素であり、
Xが、Mgである、請求項17に記載の吸着材料。 - R1、R2、R3、R4、R5、およびR6が各々、水素であり、
Zが、炭素であり、
Xが、Mgであり、ジアミンが、前記Mgとも配位結合する、請求項19に記載の吸着材料。 - 煙道ガスからCO2を減少させるための方法であって、
(a)前記煙道ガスを、請求項1〜20のいずれか一項に記載の吸着材料と接触させて、前記煙道ガスからCO2を可逆的に吸着し、それによりCO2に富む吸着材料を生成することと、
(b)温度スイング吸着法、真空スイング吸着法、圧力スイング吸着法、濃度スイング吸着法、またはそれらの組み合わせを使用して、前記CO2に富む吸着材料から前記CO2の大部分をストリッピングすることと、を含む、方法。 - 煙道ガスが、4%(40mbar)以下のCO2を含み、前記吸着プロセスが、0.4%(4mbar)以下の濃度まで、前記煙道ガスから前記CO2の90%超を除去する、請求項21に記載の方法。
- バイオガスからCO2を除去するための方法であって、前記バイオガスを、請求項1〜20のいずれか一項に記載の吸着材料と接触させて、前記バイオガスからCO2を可逆的に吸着することを含み、前記接触させることは、それによりCO2に富む吸着材料と、2%以下のCO2を有する精製メタンを含む残留ガスとを生成する、方法。
- 前記方法が、ターゲットガスストリームから前記CO2の90パーセント超を吸着することと、温度スイング吸着法、真空スイング吸着法、圧力スイング吸着法、濃度スイング吸着法、またはそれらの組み合わせを使用して、前記CO2に富む吸着材料から前記CO2をストリッピングすることと、をさらに含む、請求項23に記載の方法。
- 供給源によって生成された二酸化炭素を捕捉する方法であって、請求項1〜20のいずれか一項に記載の吸着材料に前記二酸化炭素を曝露することを含み、それにより前記二酸化炭素が、前記吸着材料中に可逆的に捕捉される、方法。
- 前記方法が、温度スイング吸着法、真空スイング吸着法、圧力スイング吸着法、濃度スイング吸着法、またはそれらの組み合わせを使用して、前記CO2に富む吸着材料を再生させることをさらに含む、請求項25に記載の方法。
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