JP2012509360A - 金属有機構造体型結晶性ポーラスアルミニウムカルボキシラートの水熱製造方法 - Google Patents
金属有機構造体型結晶性ポーラスアルミニウムカルボキシラートの水熱製造方法 Download PDFInfo
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- JP2012509360A JP2012509360A JP2011543803A JP2011543803A JP2012509360A JP 2012509360 A JP2012509360 A JP 2012509360A JP 2011543803 A JP2011543803 A JP 2011543803A JP 2011543803 A JP2011543803 A JP 2011543803A JP 2012509360 A JP2012509360 A JP 2012509360A
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- solid
- mil
- metal
- carboxylate
- iii
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- -1 aluminum carboxylate Chemical class 0.000 title claims abstract description 52
- 229910052782 aluminium Inorganic materials 0.000 title claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 37
- 239000002184 metal Substances 0.000 title claims abstract description 37
- 238000001027 hydrothermal synthesis Methods 0.000 title abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 89
- 238000003860 storage Methods 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000011148 porous material Substances 0.000 claims description 24
- 229910001868 water Inorganic materials 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000004913 activation Effects 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 claims description 5
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003367 polycyclic group Polymers 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 claims description 2
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 claims description 2
- QPBGNSFASPVGTP-UHFFFAOYSA-N 2-bromoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Br)=C1 QPBGNSFASPVGTP-UHFFFAOYSA-N 0.000 claims description 2
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 claims description 2
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 claims description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-L 4-(4-carboxylatophenyl)benzoate Chemical compound C1=CC(C(=O)[O-])=CC=C1C1=CC=C(C([O-])=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-L 0.000 claims description 2
- PEQRGMPXYDIZSX-UHFFFAOYSA-N 4-[4-[3,5-bis[4-(4-carboxyphenyl)phenyl]phenyl]phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=2C=C(C=C(C=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(O)=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1 PEQRGMPXYDIZSX-UHFFFAOYSA-N 0.000 claims description 2
- QURGMSIQFRADOZ-UHFFFAOYSA-N 5-(3,5-dicarboxyphenyl)benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C=2C=C(C=C(C=2)C(O)=O)C(O)=O)=C1 QURGMSIQFRADOZ-UHFFFAOYSA-N 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- ZLKNTGYYEIQDNX-UHFFFAOYSA-N carboxy 4-(4-carboxyoxycarbonylphenyl)benzoate Chemical compound C1=CC(C(=O)OC(=O)O)=CC=C1C1=CC=C(C(=O)OC(O)=O)C=C1 ZLKNTGYYEIQDNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- OLAPPGSPBNVTRF-UHFFFAOYSA-J naphthalene-1,4,5,8-tetracarboxylate Chemical compound C1=CC(C([O-])=O)=C2C(C(=O)[O-])=CC=C(C([O-])=O)C2=C1C([O-])=O OLAPPGSPBNVTRF-UHFFFAOYSA-J 0.000 claims description 2
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 claims description 2
- QUMITRDILMWWBC-UHFFFAOYSA-N nitroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QUMITRDILMWWBC-UHFFFAOYSA-N 0.000 claims description 2
- GMIOYJQLNFNGPR-UHFFFAOYSA-L pyrazine-2,5-dicarboxylate Chemical compound [O-]C(=O)C1=CN=C(C([O-])=O)C=N1 GMIOYJQLNFNGPR-UHFFFAOYSA-L 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 2
- 239000003021 water soluble solvent Substances 0.000 claims description 2
- SVAJWMFPXLZPHL-UHFFFAOYSA-N 2-[3,5-bis(2-carboxyphenyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC(C=2C(=CC=CC=2)C(O)=O)=CC(C=2C(=CC=CC=2)C(O)=O)=C1 SVAJWMFPXLZPHL-UHFFFAOYSA-N 0.000 claims 1
- ZBWJNGCWUAUFTI-UHFFFAOYSA-N 4-(4-carboxyphenyl)-2,3,5,6-tetramethylbenzoic acid Chemical compound CC1=C(C(O)=O)C(C)=C(C)C(C=2C=CC(=CC=2)C(O)=O)=C1C ZBWJNGCWUAUFTI-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- BKRIRZXWWALTPU-UHFFFAOYSA-N methyl 4-(4-methoxycarbonylphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)OC)C=C1 BKRIRZXWWALTPU-UHFFFAOYSA-N 0.000 claims 1
- YCGAZNXXGKTASZ-UHFFFAOYSA-L thiophene-2,5-dicarboxylate Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-L 0.000 claims 1
- 239000012621 metal-organic framework Substances 0.000 abstract description 39
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- 239000013291 MIL-100 Substances 0.000 description 38
- 235000010210 aluminium Nutrition 0.000 description 35
- 239000000463 material Substances 0.000 description 22
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 17
- 238000001228 spectrum Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000013206 MIL-53 Substances 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000005004 MAS NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- CYIDZMCFTVVTJO-UHFFFAOYSA-J benzene-1,2,4,5-tetracarboxylate Chemical compound [O-]C(=O)C1=CC(C([O-])=O)=C(C([O-])=O)C=C1C([O-])=O CYIDZMCFTVVTJO-UHFFFAOYSA-J 0.000 description 3
- QMKYBPDZANOJGF-UHFFFAOYSA-K benzene-1,3,5-tricarboxylate(3-) Chemical compound [O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-K 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000013110 organic ligand Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 238000004438 BET method Methods 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 239000013177 MIL-101 Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- SWRBZMNVPSRIKF-UHFFFAOYSA-K aluminum;benzene-1,3,5-tricarboxylate Chemical compound [Al+3].[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 SWRBZMNVPSRIKF-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000013254 iso-reticular metal–organic framework Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000013336 microporous metal-organic framework Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 230000009897 systematic effect Effects 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MBJVVOOZVAMSIT-UHFFFAOYSA-N CC1=C(C(=C(C(=C1C1=CC=C(C=C1)C(=O)O)C)C)C(=O)O)C.COC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OC Chemical compound CC1=C(C(=C(C(=C1C1=CC=C(C=C1)C(=O)O)C)C)C(=O)O)C.COC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OC MBJVVOOZVAMSIT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000013148 Cu-BTC MOF Substances 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000013132 MOF-5 Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- QPGJEXWQNJCCSN-UHFFFAOYSA-K [Cu+3].[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 Chemical compound [Cu+3].[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 QPGJEXWQNJCCSN-UHFFFAOYSA-K 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- NDDSLRBEFUQGFB-UHFFFAOYSA-K aluminum;naphthalene-1-carboxylate Chemical compound [Al+3].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 NDDSLRBEFUQGFB-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- XTUBPKVLOAIMQY-UHFFFAOYSA-H chromium(3+);terephthalate Chemical compound [Cr+3].[Cr+3].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 XTUBPKVLOAIMQY-UHFFFAOYSA-H 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013141 crystalline metal-organic framework Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- BFPVXOYPQMBHDJ-UHFFFAOYSA-H dialuminum;terephthalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 BFPVXOYPQMBHDJ-UHFFFAOYSA-H 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004405 heteroalkoxy group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000013337 mesoporous metal-organic framework Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007783 nanoporous material Substances 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000013384 organic framework Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000013259 porous coordination polymer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- ZMQKJSOLVPOQHR-UHFFFAOYSA-N prop-1-yne Chemical compound CC#[C] ZMQKJSOLVPOQHR-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/3085—Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Gas Separation By Absorption (AREA)
Abstract
Description
特に、再生可能な、環境にやさしい、産業上利用可能な、かつ金属有機構造体、MOF型の結晶性ポーラスなアルミニウムカルボキシラートの製造を可能とする方法に対して実際の要求が存在する。
(i)水溶液中で、
金属Al、金属塩Al3+又は金属イオンAl3+を含む配位化合物の形での少なくとも金属無機前駆体と;及び
少なくとも前記配位子Lの有機前駆体とを混合するステップと;
(ii)前記混合物のpHを3よりも低く調節するステップと;
(iii)前記(ii)で得られた前記混合物を130℃よりも高い温度で加熱して前記固体を得る
ステップとを、含む。
(ここでLは、式Ro(COO−)qの、ジ−、トリ−又はテトラカルボキシラートリガンドであり、Roは、モノ−又はポリ−サイクリック、縮合又は非縮合のアリールラジカルであり、6から50、例えば6から27の炭素数を持ち、又モノ−又はポリ−サイクリック、縮合又は非縮合のヘテロアリールラジカルであり、4から50、例えば4から20の炭素数を持ち、Roは、C1−10アルキル、C2−10アルキレン、C2−10アルキン、C3−10シクロアルキル、C1−10ヘテロアルキル、C1−10ハロアルキル、C6−10アリール、C3−20ヘテロサイクリック、C6−10アリールC1−10アルキル、C3−10ヘテロアリールC1−10アルキル、F、Cl、Br、I、−NO2、−CN、−CF3、−CH2CF3、−OH、−CH2OH、−CH2CH2OH、−NH2、−CH2NH2、−NHCHO、−COOH、−CONH2、−SO3H、−PO3H2を含む群から選択される、独立した少なくともひとつ又はそれ以上により置換されてもよく、q=2から4である)。
ステップ(ii)で適切な酸は、MOFの構造にも製造方法にも影響を与えないものが有利である。例示により、HCl、HNO3、H2SO4を含む群から選択される鉱酸が挙げられる。特に酸としてはHNO3が挙げられる。
ここで、
Alは、Al3+;
mは、1から15、例えば1から8;
kは、0から15、例えば1から8;
lは、0から10、例えば1から8;
pは、1から10、例えば1から5;
m、k、l及びpは、前記パターンの荷電が中和されるように選択される;
Xは、OH−、Cl−、F−、Br−、SO4 2−、NO3 −、ClO4 −、PF6 −、BF3 −、R1−(COO−)n、R1−(SO3 −)n、R1−(PO3 −)nを含む群から選択されるアニオンであり、R1は水素、直鎖又は分枝、場合により置換されていてもよいC1−12アルキルであり、n=1から4を表す。
Lは、上で定義されたものである。
結晶性固体である(結晶化は与えられたpHで実施される)、
高純度である(例えば水酸化アルミニウムなどの副生成物は見出されない)、及び
十分な多孔性を示し(3500m2.g−1までのLangmuir比表面積)、特に、特定の分子の吸収特性を制御することを可能にする。
化合物MIL−100(Al)は、我々の実験室で既に記載されたクロミウム(III)及び鉄(III)の類似物である。この相は、1.314gのアルミニウムナイトラート(Al(NO3)3.9H2O)、0.596gのトリメチルベンゼン−1,3,5−トリカルボキシラート、4.4mlの硝酸(HNO31M)及び16mlの水の混合物を125mlのテフロン(登録商標)セルに入れ、それをParr(商品名)スチールオートクレーブに挿入した。反応は、210°Cで3時間、オーブン(温度上昇:1時間)中で行い、0.55gのMIL−100(Al)を得る。反応pHは1.8である。
を持つ立方単位の結晶である。
MIL−100(Al)の固体1HNMR(図19a)により、3つの主なエコーシグナル、4.8、8.0及び9.1ppmは水、H3btc、及びbtc構造にそれぞれ帰属されることが分かる。水は存在して、Al3トリマー単位構造に結合する末端リガンドだけでなく、化合物のポアにも吸収されている。結合された水分子とAl構造との近接性を確立するために、1H/27AlTRAPDOR実験を行った[29]。TRAPDOR実験の目的は、マジックアングルスピニング(MAS)条件で2つの異なるスピン間のダイポール相互作用を測定することである。
化合物MIL−120(Al)は、3.2gのアルミニウムナイトラート(Al(NO3)3.9H2O)、0.5gのベンゼン−1,2,4,5−テトラカルボキシラート、3.2mlの水酸化ナトリウム(NaOH4M)及び20mlの水の混合物を125mlのテフロン(登録商標)セルに入れ、それをParr(商品名)スチールオートクレーブ に挿入した。反応は、210°Cで24時間、オーブン中で行い、0.68gのMIL−120(Al)を得る。反応pHは1.85である。生成物を一夜還流しながら蒸留水で洗浄した。200℃で一夜加熱して活性化した。
化合物MIL−121(Al)は、9.6gのアルミニウムナイトラート(Al(NO3)3.9H2O)、3.2gのベンゼン−1,2,4,5−テトラカルボキシラート及び40mlの水の混合物を125mlのテフロン(登録商標)セルに入れ、それをParr(商品名)スチールオートクレーブ に挿入した。反応は、210°Cで24時間、オーブン中で行った。反応pHは0.2である。3.45gのMIL−121(Al)を得る。380℃で4時間加熱して活性化した。
文献リスト
[1]
Reticular Synthesis and the Design of New Materials, O.M. Yaghi, M. O’Keeffe, N.W. Ockwig, H.K.
Chae, M. Eddaoudi and J. Kim, Nature, 423, 705-14(2003).
[2]
Functional Porous Coordination Polymers, S. Kitagawa, R. Kitaura and S.-l.
Noro, Angew. Chem. Int. Ed., 43, 2334-75 (2004).
[3] Hybrid
Porous Solids: Past, Present, Future, G. Ferey, Chem. Soc. Rev., 37, 191-214 (2008).
[4]
Hydrogen Storage in Microporous Metal-Organic Frameworks, N.L. Rosi, J. Eckert,
M. Eddaoudi, D.T. Vodak, J. Kim, M. O’Keeffe and O.M. Yaghi, Science, 300, 1127-9 (2003).
[5]
Hydrogen Adsorption in the Nanoporous Metal-benzenedicarboxylate
M(OH)(O2C-C6H4-CO2) (M = Al3+, Cr3+), MIL-53, G. Ferey, M. Latroche, C. Serre,
F. Millange, T. Loiseau and A. Percheron-Gueegan, Chem. Commun., 2976-7 (2003).
[6]
Hydrogen Storage in the Giant-Pore Metal-Organic Frameworks MIL-100 and
MIL-101, M. Latroche, S. Surble, C. Serre, C. Mellot-Draznieks, P.L. Llewellyn, J.-H. Lee, J.-S.
Chang, S.H. Jhung and G. Ferey, Angew. Chem. Int. Ed., 45, 8227 (2006).
[7]
Systematic Design of Pore Size and Functionality in Isoreticular MOFs and their
Application in Methane Storage, M. Eddaoudi, J. Kim, N. Rosi, D. Vodak, J. Wachter,
M. O’Keeffe and
O.M. Yaghi, Nature, 295,469-72 (2002).
[8]
Different Adsorption Behaviors of Methane and Carbon Dioxide in the Isotypic
Nanoporous Metal Terephthalates MIL-53 and MIL-47, S. Bourrelly, P. L.
Llewellyn, C. Serre, F. Millange, T. Loiseau and G. Ferey, J. Am. Chem. Soc, 127,
13519-21 (2005).
[9]
Metal-Organic Frameworks as Efficient Materials for Drug Delivery, P.
Horcajada, C. Serre, M. Vallet-Regi, M. Sebban, F. Taulelle and G. Ferey, Angew. Chem. Int. Ed.,
45, 5974 (2006).
[10] High
Gas Adsorption in a Microporous Metal-Organic Framework with Open-Framework,
O.M. Yaghi, WO 2006/110740 (2006).
[11]
Isoreticular Metal-Organic Framework Process for Forming the Same and
Systematic Design of Pore size and Functionality therein, with Application for
Gas Storage, WO 02/088148 (2002).
[12]
Metal-Organic Frameworks - Prospective Industrial Applications, U. Muller, M. Schubert, F. Teich,
H. Putter, K.
Schierle-Arndt and J. Pastre, J. Mater. Chem., 16, 626-36 (2006).
[13] Shaped
Bodies Containing Metal-Organic Frameworks, M. Hesse, U. Muller, O.M. Yaghi, WO
2006/050898 (2006).
[14] A
Rationale for the Large Breathing of the Porous Aluminum Terephthalate (MIL-53)
Upon Hydration, T. Loiseau, C. Serre, C. Huguenard, G. Fink, F. Taulelle, M.
Henry, T. Bataille and G. Ferey, Chem. Eur. J., 10, 1373-82 (2004).
[15]
Hydrothermal Synthesis and Crystal Structure of a New Three-Dimensional
Aluminum-Organic Framework MIL-69 with
2,6-Naphthalenedicarboxylate (ndc), AI(OH)(ndc)QH20, T. Loiseau, C.
Mellot-Draznieks, H. Muguerra, G. Ferey, M. Haouas and F. Taulelle, C. R. Chimie, Special Issue on
Crystalline and Organized Porous Solids, 8, 765-72 (2005).
[16] MIL-96, a Porous Aluminum Trimesate 3D
Structure Constructed from a Hexagonal Network of 18-Membered Rings and μ3-0x0- Centered Trinuclear
Units, T. Loiseau, L. Lecroq, C. Volkringer, J. Marrot, G. Ferey, M. Haouas, F. Taulelle,
S. Bourrelly, P. L. Llewellyn and M. Latroche, J. Am. Chem. Soc, 128, 10223-30
(2006).
[17] A
Microdiffraction Set-up for Nanoporous Metal-Organ ic-Framework-Type Solids, C.
Volkringer, D. Popov, T. Loiseau, N. Guillou, G. Ferey, M. Haouas, F. Taulelle,
C. Mellot-Draznieks, M. Burghammer and C. Riekel, Nature Matehals, 6, 760-4
(2007).
[18] Design
and Synthesis of an Exceptionally Stable and Highly Porous Metal-Organic
Framework. H. Li, M. Eddaoudi, M. O’Keeffe, O.M. Yaghi, Nature, 402, 276-9 (1999).
[19] A
Chemically Functionalizable Nanoporous Material [Cu3(TMA)2(H2O)3]n, S.S.-Y.
Chui, S.M.-F. Lo, J.P.H. Charmant, A. Guy Orpen and I.D. Williams, Science,
283, 1148 (1999).
[20]
Method for Producing
Organometallic Framework Materials Containing Main Group Metal
Ions, M. Schubert, U. Muller, M. Tonigold, R. Ruetz, WO 2007/023134 (2007).
[21]
Mesoporous Metal-Organic Framework, M. Schubert, U. Muller, H. Mattenheimer, M.
Tonigold, WO 2007/023119 (2007).
[22]
Organometallic Aluminum Fumarate Backbone Material, C. Kiener, U. Muller, M. Schubert, WO 2007/118841
(2007).
[23]
Dotierte Metallorganische Gerustmaterialien, M. Schubert, U. Muller, R. Ruetz, S. Hatscher, DE 10 2005 053 430 (2005).
[24]
MOF-Compounds as Gas Adsorbers, K.O. Kongshaug, R.H. Heyn, H. Fjellvag, R.
Blom, WO 2007/128994 (2007).
[25] <<
Handbook of Hydrothermal Technology, Editors : K. Byrappa & M. Yoshimura,
William Andrew publishing, Noyes Publications Norwich, New Yordk, USA (2001)
[26]
Rabeneau et al., Angew. Chem. Int. Ed. 24 1026-40 (1985).
[27] <<How
hydration drastically improves adsorption selectivity for CO2 over CH4 in the
flexible Chromium terephthalate MIL-53>>, P.L. Llewellyn, S. Bourrelly,
C. Serre, Y. Filinchuk and G. Ferey, Angew. Chem. Int. Ed. 45 7751-4 (2006).
[28] <<
Synthesis and catalysis properties of MIL-100(Fe), an iron(lll) carboxylate
with large pores >> P. Horcajada, S. Surble, C. Serre, D.-Y. Hong, Y.-K. Seo, J.-S Chang,
J.-M. Greneche, I. Margiolaki and G. Ferey, Chem. Commun. 2820-2 (2007); << Catalytic properties of
MIL-101 >> A. Henschel, K. Gedrich, R. Kraehnert and S. Kaskel, Chem.
Commun. 4192-4 (2008); <<Amine grafting on coordinatively unsaturated
metal centers of MOFs: consequences for catalytis and metal encapsulation >>
Y.K. Hwang, D.-Y. Hong, J.-S. Chang, S.H. Jhung, Y.-K. Seo, J. Kim, A. Vimont,
M. Daturi, C. Serre and G. Ferey, Angew. Chem. Int. Ed. 47 4144-8 (2008).
[29] E.R.H
van Eck, R. Janssen, W.E.J.R. Maas, W.S. Veeman, Chem.Phys. Letters, 1990, 174,
428.
[30] Medek
A, Harwood JS, Frydman L, J. Am. Chem. soc. 1995, 117, 12779.
Claims (25)
- 結晶性のポーラスなアルミニウムカルボキシラートの金属有機構造体(MOF)からなる固体の水熱製造方法であり、本発明は次のステップ:
(i)水溶液中で、
金属Al、金属塩Al3+又は金属イオンAl3+を含む配位化合物の形での少なくとも金属無機前駆体と;及び
少なくとも前記配位子L(ここでLは、式Ro(COO−)qの、ジ−、トリ−又はテトラカルボキシラートリガンドであり、Roは、モノ−又はポリ−サイクリック、縮合又は非縮合のアリールラジカルであり、6から50、例えば6から27の炭素数を持ち、又モノ−又はポリ−サイクリック、縮合又は非縮合のヘテロアリールラジカルであり、4から50、例えば4から20の炭素数を持ち、Roは、C1−10アルキル、C2−10アルキレン、C2−10アルキン、C3−10シクロアルキル、C1−10ヘテロアルキル、C1−10ハロアルキル、C6−10アリール、C3−20ヘテロサイクリック、C6−10アリールC1−10アルキル、C3−10ヘテロアリールC1−10アルキル、F、Cl、Br、I、−NO2、−CN、−CF3、−CH2CF3、−OH、−CH2OH、−CH2CH2OH、−NH2、−CH2NH2、−NHCHO、−COOH、−CONH2、−SO3H、−PO3H2を含む群から選択される、独立した少なくともひとつ又はそれ以上により置換されていてもよく、q=2から4である)の有機前駆体とを混合するステップと;
(ii)前記混合物のpHを3よりも低く調節するステップと;
(iii)前記(ii)で得られた前記混合物を130℃よりも高い温度で加熱して前記固体を得るステップとを含む方法。 - 請求項1に記載の方法であり、前記水溶性溶媒が水である、方法。
- 前記1または2もいずれか1項に記載の方法であり、ステップ(i)において前記金属無機前駆体及び前記リガンドLの前記有機前駆体がモル比1から5の間を含む、方法。
- 請求項1乃至3のいずれか一項に記載の方法であり、前記金属無機前駆体が、金属Al又はAl3+塩である、方法。
- 請求項1乃至4のいずれか一項に記載の方法であり、前記Lが、C2H2(CO2 −)2(フマレート),C2H4(CO2 −)2(スクシネート),C3H6(CO2 −)2(グルタレート),C4H4(CO2 −)2(ムコネート),C4H8(CO2 −)2(アジペート),C5H3S(CO2 −)2(チオフェン−2,5−ジカルボキシラート),C6H4(CO2 −)2(テレフタレート),C6H2N2(CO2 −)2(ピラジン−2,5−ジカルボキシラート),C10H6(CO2 −)2(2,6−ナフタレンジカルボキシレート),C12H8(CO2 −)2(4,4’−ビフェニルジカルボキシレート),C6H3(CO2 −)3(ベンゼン−1,2,4−トリカルボキシレート),C6H3(CO2 −)3(ベンゼン−1,3,5−トリカルボキシレート),C24H15(CO2 −)3(ベンゼン−1,3,5−トリベンゾエート),C42H27(CO2 −)3(1,3,5−トリ[4’カルボキシ(1,1’−ビフェニル−4−イル)]ベンゼン),C6H2(CO2 −)4(ベンゼン−1,2,4,5−テトラカルボキシレート),C10H4(CO2 −)4(ナフタレン−2,3,6,7−テトラカルボキシレート),C10H4(CO2 −)4(ナフタレン−1,4,5,8−テトラカルボキシレート),C12H6(CO2 −)4(ビフェニル−3,5,3’,5’−テトラカルボキシレート)を含む群から選択される配位子及びジ−,トリ−又はテトラカルボキシラート配位子、及び2−アミノテレフタレート,2−ニトロテレフタレート,2−メチルテレフタレート,2−クロロテレフタレート,2−ブロモテレフタレート,2,5−ジヒドロキシテレフタレート,テトラフルオロテレフタレート,2,5−ジカルボキシテレフタレート,ジメチルビフェニル−4,4’−ジカルボキシラート,テトラメチルビフェニル−4,4’−ジカルボキレート,ジカルボキシビフェニル−4,4’−ジカルボキシレートを含む群から選択される変性された類似の配位子である、方法。
- 請求項1乃至5のいずれか一項に記載の方法であり、ステップ(ii)において前記混合物のpHが0.4及び2.9の間に含まれるように調節される、方法。
- 請求項1乃至6のいずれか一項に記載の方法であり、ステップ(iii)において前記混合物のpHを、酸又は塩基を添加して調節する、方法。
- 請求項1乃至7のいずれか一項に記載の方法であり、ステップ(iii)において前記混合物を140℃から220℃で加熱する、方法。
- 請求項1乃至8のいずれか一項に記載の方法であり、ステップ(iii)で、前記混合物が1から48時間加熱される、方法。
- 請求項1乃至9のいずれか一項に記載の方法であり、前記ステップ(iii)で、105Paよりも高い自原的圧力で実施される、方法。
- 請求項1乃至10のいずれか一項に記載の方法であり、さらに、ステップ(iii)で得られる個体を80℃から350℃で加熱することで活性化するステップ(iv)を含む、方法。
- 請求項11に記載の方法であり、前記活性化ステップ(iv)が、DMF、DEF、メタノール、エタノール、DMSOを含む群から選択される溶媒中で実施される、方法。
- 請求項11又は12のいずれか一項に記載の方法であり、ステップ(iii)で得られる個体を1から36時間加熱する活性化ステップ(iv)を含む、方法。
- 純度が少なくとも95質量%である単一相の結晶性ポーラスアルミニウムカルボキシラートの金属有機構造体(MOF)からなる固体であり、請求項1乃至13のいずれか一項の本発明の製造方法で得られるものであり、式(I)で表される3次元に連続するパターンを含む固体。
AlmOkXlLp (I)
(Alは、Al3+;
mは、1から15、例えば1から8;
kは、0から15、例えば1から8;
lは、0から10、例えば1から8;
pは、1から10、例えば1から5;
m、k、l及びpは、前記パターンの荷電が中和されるように選択される;
Xは、OH−、Cl−、F−、Br−、SO4 2−、NO3 −、ClO4 −、PF6 −、BF3 −、R1−(COO−)n、R1−(SO3 −)n、R1−(PO3 −)nを含む群から選択されるアニオンであり、R1は水素、直鎖又は分枝、場合により置換されていてもよいC1−12アルキルであり、n=1から4を表し、Lは請求項1で定義されたものである) - 請求項14に記載の固体であり、アニオンXが、OH−、Cl−、F−、ClO4 −を含む群から選択される、固体。
- 請求項14又は15のいずれか一項に記載の方法であり、Alの質量%が5から50%である、固体。
- 請求項14乃至16のいずれか一項に記載の固体であり、BET比表面積が100から2500m2/gである、固体。
- 請求項14乃至17のいずれか一項に記載の固体であり、 Langmuir表面積が150から3500m2/gである、固体。
- 請求項14乃至18のいずれか一項に記載の固体であり、前記固体のポア直径が0.2から6mmである、固体。
- 請求項14乃至19のいずれか一項に記載の固体であり、前記固体のポア容量が0.1から4cm3/gである、固体。
- 請求項14乃至20のいずれか一項に記載の固体であり、前記固体が、500℃までの熱安定性を有する、固体。
- 請求項14乃至21のいずれか一項に記載の固体であり、前記固体が、0.1μmから150μmの範囲の長さを持つ結晶形である、個体。
- 液体又はガスの貯蔵のための、請求項14乃至22のいずれか一項に記載の固体の使用。
- ガス分離のための、請求項14乃至22のいずれか一項に記載の固体の使用。
- 触媒のための、請求項14乃至22のいずれか一項に記載の固体の使用。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016185534A (ja) * | 2015-03-27 | 2016-10-27 | 新日鐵住金株式会社 | ガス吸着材ならびにガス分離装置及びガス貯蔵装置 |
WO2023080247A1 (ja) * | 2021-11-08 | 2023-05-11 | Eneos株式会社 | 複合体、二酸化炭素捕捉剤、及び複合体の製造方法 |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8343261B2 (en) * | 2008-03-17 | 2013-01-01 | Basf Se | Use of formate-based porous metal organic frameworks for methane storage |
CA2812032A1 (en) * | 2010-09-30 | 2012-04-05 | Basf Se | Process for preparing porous metal-organic frameworks based on aluminum fumarate |
US8524932B2 (en) * | 2010-09-30 | 2013-09-03 | Basf Se | Process for preparing porous metal-organic frameworks based on aluminum fumarate |
RU2014103959A (ru) * | 2011-07-06 | 2015-08-20 | Басф Се | Способ получения пористой металлорганической каркасной структуры, состоящей из метилимидазолята цинка |
US9096616B2 (en) | 2011-07-06 | 2015-08-04 | Basf Se | Process for preparing a porous metal-organic framework composed of zinc methylimidazolate |
EP2578593A1 (en) | 2011-10-04 | 2013-04-10 | Fundació Privada Institut Català de Nanotecnologia | Method for the preparation of metal organic frameworks |
CN102731537A (zh) * | 2011-11-09 | 2012-10-17 | 长春工业大学 | 一种具有穿插结构的呋喃二甲酸锌金属有机骨架材料及制备方法 |
JP5829924B2 (ja) * | 2012-01-16 | 2015-12-09 | 東洋紡株式会社 | 多孔性複合材料とその製造方法、及び硫化水素ガス除去材 |
CN105050699A (zh) * | 2012-10-22 | 2015-11-11 | 得克萨斯A&M大学体系 | 使用热诱导的自组装在载体上快速沉积多微孔材料薄膜(或涂层)的方法 |
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GB201414114D0 (en) | 2013-11-26 | 2014-09-24 | Texas A & M Univ Sys | Aluminium metal organic framework materials |
CA2951200A1 (en) | 2014-06-10 | 2015-12-17 | Cambridge Enterprise Limited | Metal-organic frameworks |
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JP7165491B2 (ja) * | 2017-02-23 | 2022-11-04 | 住友化学株式会社 | 光学フィルム及びその製造方法 |
ES2682056B1 (es) | 2017-03-16 | 2019-06-28 | Univ Zaragoza | Material hibrido poroso organico - inorganico, metodo de obtencion y usos |
WO2019152962A2 (en) | 2018-02-05 | 2019-08-08 | The Regents Of The University Of California | Atmospheric moisture harvester |
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CN114073987B (zh) * | 2020-08-17 | 2023-05-26 | 中国科学院大连化学物理研究所 | 具有存储-氧化串联消除甲醛的催化剂及其制备和应用 |
KR20240026218A (ko) * | 2021-06-28 | 2024-02-27 | 엑손모빌 테크놀로지 앤드 엔지니어링 컴퍼니 | 전구체 및 결정화 보조제를 사용하여 금속-유기 골격을 제조하는 방법 |
WO2023002141A1 (fr) | 2021-07-23 | 2023-01-26 | Centre National De La Recherche Scientifique | Procede de preparation d'un tetracarboxylate d'aluminium poreux cristallise de type mof, et utilisations de celui-ci |
CN113666822B (zh) * | 2021-08-24 | 2022-08-09 | 桂林医学院 | 用于铝离子检测与细胞成像的小分子荧光探针及其应用 |
DE102022106916A1 (de) | 2022-03-23 | 2023-09-28 | Christian-Albrechts-Universität zu Kiel, Körperschaft des öffentlichen Rechts | Poröse, kristalline verbindung |
CN116143618B (zh) * | 2023-04-19 | 2023-08-01 | 吉林省卓材新研科技有限公司 | 水系锌离子电池用金属有机框架材料及配体和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06220067A (ja) * | 1990-12-14 | 1994-08-09 | Aluminum Co Of America <Alcoa> | アルミノ有機化合物及びその製造方法 |
WO2007023119A1 (de) * | 2005-08-22 | 2007-03-01 | Basf Aktiengesellschaft | Mesoporöses metallorganisches gerüstmaterial |
CN101269317A (zh) * | 2007-03-23 | 2008-09-24 | 中国科学院大连化学物理研究所 | 一种负载型多孔金属有机化合物储氢材料 |
CN101289161A (zh) * | 2007-04-20 | 2008-10-22 | 中国科学院大连化学物理研究所 | 一种储氢材料的制备方法 |
JP2011520592A (ja) * | 2008-04-22 | 2011-07-21 | ユニヴェルシテ ドゥ モンス | ガス吸着剤 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1383775B1 (en) | 2001-04-30 | 2006-08-02 | The Regents of The University of Michigan | Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein,with application for gas storage |
US7524444B2 (en) | 2004-11-09 | 2009-04-28 | Basf Aktiengesellschaft | Shaped bodies containing metal-organic frameworks |
EP1874459B1 (en) | 2005-04-07 | 2015-10-14 | The Regents of The University of Michigan | High gas adsorption in a microporous metal-organic framework with open-metal sites |
DE102005039623A1 (de) | 2005-08-22 | 2007-03-01 | Basf Ag | Verfahren zur Herstellung von metallorganischen Gerüstmaterialien Hauptgruppen Metallionen enthaltend |
DE102005053430A1 (de) | 2005-11-09 | 2007-05-16 | Basf Ag | Dotierte metallorganische Gerüstmaterialien |
GB2437063A (en) | 2006-04-10 | 2007-10-17 | Uni I Oslo | A process for oxide gas capture |
EP2010315A2 (de) | 2006-04-18 | 2009-01-07 | Basf Se | Metallorganisches gerüstmaterial aus aluminiumfumarat |
CN101337192B (zh) * | 2007-07-04 | 2010-07-21 | 中国科学院大连化学物理研究所 | 一种中微孔金属有机化合物及其制备 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06220067A (ja) * | 1990-12-14 | 1994-08-09 | Aluminum Co Of America <Alcoa> | アルミノ有機化合物及びその製造方法 |
WO2007023119A1 (de) * | 2005-08-22 | 2007-03-01 | Basf Aktiengesellschaft | Mesoporöses metallorganisches gerüstmaterial |
CN101269317A (zh) * | 2007-03-23 | 2008-09-24 | 中国科学院大连化学物理研究所 | 一种负载型多孔金属有机化合物储氢材料 |
CN101289161A (zh) * | 2007-04-20 | 2008-10-22 | 中国科学院大连化学物理研究所 | 一种储氢材料的制备方法 |
JP2011520592A (ja) * | 2008-04-22 | 2011-07-21 | ユニヴェルシテ ドゥ モンス | ガス吸着剤 |
Non-Patent Citations (3)
Title |
---|
JPN5012006757; LOISEAU, THIERRY: 'MIL-96, A POROUS ALUMINUM TRIMESATE 3D STRUCTURE CONSTRUCTED FROM A HEXAGONAL NETWORK 以下備考' JOURNAL OF THE AMERICAN CHEMICAL SOCIETY V128 N31, 2006, P10223-10230 * |
JPN5012006758; VOLKRINGER, C.: 'A MICRODIFFRACTION SET-UP FOR NANOPOROUS METAL-ORGANIC-FRAMEWORK-TYPE SOLIDS' NATURE MATERIALS V6, 2007, P760-764 * |
JPN5012006759; LOISEAU, T.: 'A RATIONALE FOR THE LARGE BREATHING OF THE POROUS ALUMINUM TEREPHTHALATE (MIL-53) UPON HYDRATION' CHEMISTRY-A EUROPEAN JOURNAL V10, 2004, P1373-1382 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016185534A (ja) * | 2015-03-27 | 2016-10-27 | 新日鐵住金株式会社 | ガス吸着材ならびにガス分離装置及びガス貯蔵装置 |
WO2023080247A1 (ja) * | 2021-11-08 | 2023-05-11 | Eneos株式会社 | 複合体、二酸化炭素捕捉剤、及び複合体の製造方法 |
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JP2016155879A (ja) | 2016-09-01 |
US8658562B2 (en) | 2014-02-25 |
EP2376503B1 (fr) | 2018-07-04 |
WO2010058123A1 (fr) | 2010-05-27 |
FR2938540B1 (fr) | 2017-08-11 |
EP2376503A1 (fr) | 2011-10-19 |
FR2938540A1 (fr) | 2010-05-21 |
JP6004650B2 (ja) | 2016-10-12 |
US20120055880A1 (en) | 2012-03-08 |
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