JP2009506991A - 主族金属イオンを含有する金属有機骨格材料の製造方法 - Google Patents
主族金属イオンを含有する金属有機骨格材料の製造方法 Download PDFInfo
- Publication number
- JP2009506991A JP2009506991A JP2008527449A JP2008527449A JP2009506991A JP 2009506991 A JP2009506991 A JP 2009506991A JP 2008527449 A JP2008527449 A JP 2008527449A JP 2008527449 A JP2008527449 A JP 2008527449A JP 2009506991 A JP2009506991 A JP 2009506991A
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- Prior art keywords
- acid
- metal
- dicarboxylic acid
- framework material
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 79
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 title claims description 78
- 229910021645 metal ion Inorganic materials 0.000 title description 2
- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 239000002184 metal Substances 0.000 claims abstract description 33
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 32
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 238000003756 stirring Methods 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 19
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- -1 cycloketone Chemical compound 0.000 claims description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 6
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 6
- 238000001354 calcination Methods 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 238000013270 controlled release Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 229910052790 beryllium Inorganic materials 0.000 abstract description 2
- 229910052791 calcium Inorganic materials 0.000 abstract description 2
- 229910052733 gallium Inorganic materials 0.000 abstract 1
- 229910052738 indium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910052712 strontium Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
- 239000000047 product Substances 0.000 description 43
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 40
- 239000012065 filter cake Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000011148 porous material Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- 239000002904 solvent Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- 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 10
- 239000007789 gas Substances 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000004898 kneading Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 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 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 229920002266 Pluriol® Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 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 description 4
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- ZEVWQFWTGHFIDH-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1N=CNC=1C(O)=O ZEVWQFWTGHFIDH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- 239000004809 Teflon Substances 0.000 description 3
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- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- 239000013122 aluminium-based metal-organic framework Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
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- 239000003795 chemical substances by application Substances 0.000 description 3
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- 229910000071 diazene Inorganic materials 0.000 description 3
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical compound OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 239000013138 trimesic acid-based metal-organic framework Substances 0.000 description 3
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 2
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- BJLUCDZIWWSFIB-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(O)=O)=C1 BJLUCDZIWWSFIB-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C01B3/0005—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes
- C01B3/001—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes characterised by the uptaking medium; Treatment thereof
- C01B3/0026—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes characterised by the uptaking medium; Treatment thereof of one single metal or a rare earth metal; Treatment thereof
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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 System
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- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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- 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
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- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
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Abstract
Description
多孔質の金属有機骨格材料の製造方法によって解決される。
シュウ酸、コハク酸、酒石酸、1,4−ブタンジカルボン酸、1,4−ブテンジカルボン酸、4−オキソ−ピラン−2,6−ジカルボン酸、1,6−ヘキサンジカルボン酸、デカンジカルボン酸、1,8−ヘプタデカンジカルボン酸、1,9−ヘプタデカンジカルボン酸、ヘプタデカンジカルボン酸、アセチレンジカルボン酸、1,2−ベンゼンジカルボン酸、1,3−ベンゼンジカルボン酸、2,3−ピリジンジカルボン酸、ピリジン−2,3−ジカルボン酸、1,3−ブタジエン−1,4−ジカルボン酸、1,4−ベンゼンジカルボン酸、p−ベンゼンジカルボン酸、イミダゾール−2,4−ジカルボン酸、2−メチル−キノリン−3,4−ジカルボン酸、キノリン−2,4−ジカルボン酸、キノキサリン−2,3−ジカルボン酸、6−クロロキノキサリン−2,3−ジカルボン酸、4,4′−ジアミンフェニルメタン−3,3′−ジカルボン酸、キノリン−3,4−ジカルボン酸、7−クロロ−4−ヒドロキシキノリン−2,8−ジカルボン酸、ジイミドジカルボン酸、ピリジン−2,6−ジカルボン酸、2−メチルイミダゾール−4,5−ジカルボン酸、チオフェン−3,4−ジカルボン酸、2−イソプロピルイミダゾール−4,5−ジカルボン酸、テトラヒドロピラン−4,4−ジカルボン酸、ペリレン−3,9−ジカルボン酸、ペリレンジカルボン酸、Pluriol E 200−ジカルボン酸、3,6−ジオキサオクタンジカルボン酸、3,5−シクロヘキサジエン−1,2−ジカルボン酸、オクタジカルボン酸、ペンタン−3,3−カルボン酸、4,4′−ジアミノ−1,1′−ジフェニル−3,3′−ジカルボン酸、4,4′−ジアミノジフェニル−3,3′−ジカルボン酸、ベンジジン−3,3′−ジカルボン酸、1,4−ビス−(フェニルアミノ)−ベンゼン−2,5−ジカルボン酸、1,1′−ジナフチルジカルボン酸、7−クロロ−8−メチルキノリン−2,3−ジカルボン酸、1−アニリノアントラキノン−2,4′−ジカルボン酸、ポリテトラヒドロフラン−250−ジカルボン酸、1,4−ビス−(カルボキシメチル)−ピペラジン−2,3−ジカルボン酸、7−クロロキノリン−3,8−ジカルボン酸、1−(4−カルボキシ)−フェニル−3−(4−クロロ)−フェニルピラゾリン−4,5−ジカルボン酸、1,4,5,6,7,7,−ヘキサクロロ−5−ノルボルネン−2,3−ジカルボン酸、フェニルインダンジカルボン酸、1,3−ジベンジル−2−オキソ−イミダゾリジン−4,5−ジカルボン酸、1,4−シクロヘキサンジカルボン酸、ナフタレン−1,8−ジカルボン酸、2−ベンゾイルベンゼン−1,3−ジカルボン酸、1,3−ジベンジル−2−オキソイミダゾリジン−4,5−シス−ジカルボン酸、2,2′−ビキノリン−4,4′−ジカルボン酸、ピリジン−3,4−ジカルボン酸、3,6,9−トリオキサウンデカンジカルボン酸、ヒドロキシベンゾフェノンジカルボン酸、Pluriol E 300−ジカルボン酸、Pluriol E 400−ジカルボン酸、Pluriol E 600−ジカルボン酸、ピラゾール−3,4−ジカルボン酸、2,3−ピラジンジカルボン酸、5,6−ジメチル−2,3−ピラジンジカルボン酸、4,4′−ジアミノジフェニルエーテルジイミドジカルボン酸、4,4′−ジアミノジフェニルメタンジイミドジカルボン酸、4,4′−ジアミノジフェニルスルホンジイミドジカルボン酸、1,4−ナフタレンジカルボン酸、2,6−ナフタレンジカルボン酸、1,3−アダマンタンジカルボン酸、1,8−ナフタレンジカルボン酸、2,3−ナフタレンジカルボン酸、8−メトキシ−2,3−ナフタレンジカルボン酸、8−ニトロ−2,3−ナフタレンカルボン酸、8−スルホ−2,3−ナフタレンジカルボン酸、アントラセン−2,3−ジカルボン酸、2′,3′−ジフェニル−p−テルフェニル−4,4″−ジカルボン酸、ジフェニルエーテル−4,4′−ジカルボン酸、イミダゾール−4,5−ジカルボン酸、4(1H)−オキソチオクロメン−2,8−ジカルボン酸、5−t−ブチル−1,3−ベンゼンジカルボン酸、7,8−キノリンジカルボン酸、4,5−イミダゾールジカルボン酸、4−シクロヘキセン−1,2−ジカルボン酸、ヘキサトリアコンタンジカルボン酸、テトラデカンジカルボン酸、1,7−ヘプタジカルボン酸、5−ヒドロキシ−1,3−ベンゼンジカルボン酸、2,5−ジヒドロキシ−1,4−ジカルボン酸、ピラジン−2,3−ジカルボン酸、フラン−2,5−ジカルボン酸、1−ノネン−6,9−ジカルボン酸、エイコセンジカルボン酸、4,4′−ジヒドロキシジフェニルメタン−3,3′−ジカルボン酸、1−アミノ−4−メチル−9,10−ジオキソ−9,10−ジヒドロアントラセン−2,3−ジカルボン酸、2,5−ピリジンジカルボン酸、シクロヘキセン−2,3−ジカルボン酸,2,9−ジクロロフルオルビン−4,11−ジカルボン酸、7−クロロ−3−メチルキノリン−6,8−ジカルボン酸、2,4−ジクロロベンゾフェノン−2′,5′−ジカルボン酸、1,3−ベンゼンジカルボン酸、2,6−ピリジンジカルボン酸、1−メチルピロール−3,4−ジカルボン酸、1−ベンジル−1H−ピロール−3,4−ジカルボン酸、アントラキノン−1,5−ジカルボン酸、3,5−ピラゾールジカルボン酸、2−ニトロベンゼン−1,4−ジカルボン酸、ヘプタン−1,7−ジカルボン酸、シクロブタン−1,1−ジカルボン酸、1,14−テトラデカンジカルボン酸、5,6−デヒドロノルボルナン−2,3−ジカルボン酸、5−エチル−2,3−ピリジンジカルボン酸又はカンファージカルボン酸、
トリカルボン酸、例えば
2−ヒドロキシ−1,2,3−プロパントリカルボン酸、7−クロロ−2,3,8−キノリントリカルボン酸、1,2,3−、1,2,4−ベンゼントリカルボン酸、1,2,4−ブタントリカルボン酸、2−ホスホノ−1,2,4−ブタントリカルボン酸、1,3,5−ベンゼントリカルボン酸、1−ヒドロキシ−1,2,3−プロパントリカルボン酸、4,5−ジヒドロ−4,5−ジオキソ−1H−ピロロ[2,3−F]キノリン−2,7,9−トリカルボン酸、5−アセチル−3−アミノ−6−メチルベンゼン−1,2,4−トリカルボン酸、3−アミノ−5−ベンゾイル−6−メチルベンゼン−1,2,4−トリカルボン酸、1,2,3−プロパントリカルボン酸又はアウリントリカルボン酸、
又はテトラカルボン酸、例えば
1,1−ジオキシドペリロ[1,12−BCD]チオフェン−3,4,9,10−テトラカルボン酸、ペリレンテトラカルボン酸、例えばペリレン−3,4,9,10−テトラカルボン酸又はペリレン−1,12−スルホン−3,4,9,10−テトラカルボン酸、ブタンテトラカルボン酸、例えば1,2,3,4−ブタンテトラカルボン酸又はメソ−1,2,3,4−ブタンテトラカルボン酸、デカン−2,4,6,8−テトラカルボン酸、1,4,7,10,13,16−ヘキサオキサシクロオクタデカン−2,3,11,12−テトラカルボン酸、1,2,4,5−ベンゼンテトラカルボン酸、1,2,11,12−ドデカンテトラカルボン酸、1,2,5,6−ヘキサンテトラカルボン酸、1,2,7,8−オクタン−テトラカルボン酸、1,4,5,8−ナフタレンテトラカルボン酸、1,2,9,10−デカンテトラカルボン酸、ベンゾフェノンテトラカルボン酸、3,3′,4,4′−ベンゾフェノンテトラカルボン酸、テトラヒドロフランテトラカルボン酸又はシクロペンタンテトラカルボン酸、例えばシクロペンタン−1,2,3,4−テトラカルボン酸
を挙げることができる。
・骨格材料を、単独で又は少なくとも1つの結合剤及び/又は少なくとも1つのペースト化剤(Anteigungsmittel)及び/又は少なくとも1つのテンプレート化合物と共に混練/エッジミル粉砕(Kneten/Kollern)して、混合物を得る;
得られた混合物を、適した少なくとも1つの方法、例えば押出しにより成形する;
場合により押出物を洗浄する及び/又は乾燥する及び/又はか焼する;
場合により仕上げ加工する(Konfektionieren)。
・骨格材料を、少なくとも1つの場合により多孔質の担持材料上に施与する。得られた材料は、ついで、前記の方法に従い、成形体にさらに加工されることができる。
・骨格材料を、少なくとも1つの場合により多孔質の基体上に施与する。
テレフタル酸(BDC)5.8g及びAl(NO3)3×9H2O 26gを、DMF 100ml中に懸濁させ、混合物を133℃で還流下に16h撹拌する。引き続いて、固体をろ別し、メタノール20mlで洗浄し、真空乾燥器中で200℃で16hにわたって乾燥させる。最終的に、粉末を3日間にわたってマッフル炉(空気100l/h)中で330℃で後処理する(約75℃/hで加熱)。
テレフタル酸(BDC)19.9g及びAl2(SO4)3×18H2O 23.3gを、DMF 100ml中に懸濁させ、混合物を130℃で還流下に16h撹拌する(350rpm)。引き続いて、固体をろ別し、DMF 3×20ml及びメタノール20mlで洗浄し、真空乾燥器中で200℃で16hにわたって乾燥させる。最終的に、粉末を3日間にわたってマッフル炉(空気100l/h)中で330℃で後処理する(約75℃/hで加熱)。
テレフタル酸(BDC)19.9g及びAl2(SO4)3×18H2O 23.3gを、DEF 100ml中に懸濁させ、混合物を130℃の油浴の外部温度で130℃で16h撹拌する(290rpm)。バッチをまず最初に室温で約60h静置する。引き続いて、固体をろ別し、DMF 7×20ml及びメタノール2×20mlで洗浄し、真空乾燥器中で200℃で16hにわたって乾燥させる。最終的に、粉末を3日間にわたってマッフル炉(空気100l/h)中で330℃で後処理する(約75℃/hで加熱)。
テレフタル酸(BDC)5.8g及びAl2(SO4)3×18H2O 23.3gを、水100ml中に懸濁させ、混合物を100℃で還流下に3日間撹拌する(500rpm)。バッチをまず最初に室温で約60h静置する。引き続いて、固体をろ別し、水3×20ml及びメタノール3×20mlで洗浄し、真空乾燥器中で200℃で16hにわたって乾燥させる。最終的に、粉末を3日間にわたってマッフル炉(空気100l/h)中で330℃で後処理する(約75℃/hで加熱)。
テレフタル酸(BDC)5.76g及びAl(NO3)3×9H2O 26gを、水100ml中に懸濁させ、混合物を周囲条件で30min撹拌する。引き続いて、バッチを、Berghoffオートクレーブ("Teflonライナー")中で220℃で3日間保持する。ろ過後に、水5×20mlで洗浄し、マッフル炉(空気100l/h)中で330℃で3日間にわたって乾燥させる。
テレフタル酸(BDC)5.8g及びAl(NO3)3×9H2O 26gを、DMF 100ml中に懸濁させ、混合物を周囲条件で10min撹拌する。引き続いて、バッチを、Berghoffオートクレーブ("Teflonライナー")中で170℃で1日間保持する。ろ過後に、何度もDMFで及び引き続き何度もアセトンで洗浄する。生成物を、まず最初に真空乾燥器中で130℃で20h予備乾燥させ、マッフル炉(空気100l/h)中で330℃で3日間にわたってで乾燥させる。
テレフタル酸(BDC)292.9g及びAl2(SO4)3×18H2O 250.1gをDMF 1257g中に懸濁させ、撹拌しながら130℃に24h加熱する。引き続いて、懸濁液をろ過し、ろ過ケークを何度もDMFで後洗浄する。ろ過ケークをまず最初に、空気中で2日間予備乾燥させ、引き続きマッフル炉中で空気雰囲気下に320℃で72h乾燥させる。
テレフタル酸(BDC)19.9g及びAl2(SO4)3×18H2O 23.3gをNMP 100g中に懸濁させ、撹拌しながら130℃に24h加熱する。引き続いて、懸濁液をろ過し、ろ過ケークを何度もNMPで後洗浄する。ろ過ケークをまず最初に、空気中で2日間予備乾燥させ、引き続きマッフル炉中で空気雰囲気下に320℃で72h乾燥させる。
骨格材料5gを、300ml鋼オートクレーブ中に装入し、トルエン100gと混合する。密閉したオートクレーブ中に、液状イソブテン82mlを圧入する。オートクレーブを、170℃で3h保持した。冷却後に、液相をGCにより分析する(GC面積%):とりわけC4 68%、C8 26%が含まれている。それに加えて、高級オレフィン、例えばC16 2.3%及びC20 1.7%も見出される。
例7からのAl−MOFを、測定前に、1mbar未満の圧力で80℃で5時間、真空排気する。乾燥させた生成物161.96gを空の容器へ移す。この容器を引き続き77Kに冷却し、真空排気する。気体計量供給装置を経て、少しずつ水素を添加し、その都度取り込まれた量を重量分析によって決定する。50.3barで、Al−MOFは約3質量%の水素取り込みを達成する。
例7からのAl−MOFを、測定前に、1mbar未満の圧力で80℃で5時間、真空排気する。乾燥させた生成物161.96gを空の容器へ移す。この容器を引き続き25℃に温度調節し、真空排気する。気体計量供給装置を経て、少しずつメタンを添加し、その都度取り込まれた量を重量分析によって決定した。50.4barで、MOFの充填されたびん中にメタン40.3g/L、99.7barでそれどころか79.8g/Lが貯蔵されることができる。
テレフタル酸(BDC)398.7g及びAl2(SO4)3×18H2O 466.5gをDMF 2000ml中に懸濁させ、撹拌しながら115℃に24h加熱する。引き続いて、懸濁液をろ過し、ろ過ケークを何度もDMF 3×400ml及びメタノール400mlで後洗浄する。ろ過ケークを、まず最初にN2で96hドライブローイング(trockengeblasen)する。生成物375gが得られた。
ベンゼントリカルボン酸(BTC)7.8g及びAl(NO3)3×9H2O 22.9gをDMF 520.5g中に懸濁させ、撹拌しながら130℃に4日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをDMF 2×100ml及びメタノール4×100mlで後洗浄する。ろ過ケークを、まず最初に真空乾燥器中で200℃で16時間乾燥させる。最終的に、粉末を3日間にわたってマッフル炉(空気100l/h)中で330℃で後処理する(約75℃/hで加熱)。
ベンゼントリカルボン酸(BTC)7.8g及びAlCl3×6H2O 14.7gをDMF 520.5g中に懸濁させ、撹拌しながら130℃に4日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをDMF 2×100ml及びメタノール4×100mlで後洗浄する。ろ過ケークを、まず最初に真空乾燥器中で200℃で16時間乾燥させる。最終的に、粉末を3日間にわたってマッフル炉(空気100l/h)中で330℃で後処理する(約75℃/hで加熱)。
ベンゼントリカルボン酸(BTC)7.8g及びAl(NO3)3×9H2O 22.9gを水130.8g中に懸濁させ、撹拌しながら100℃に4日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークを水で後洗浄する。ろ過ケークを、真空乾燥器中で150℃で2日間乾燥させる。
ベンゼントリカルボン酸(BTC)7.8g及びAl(NO3)3×9H2O 22.9gを水 130.8g中に懸濁させ、Berghoffオートクレーブ(Teflonライナー)中で130℃に4日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークを水で後洗浄する。ろ過ケークを、真空乾燥器中で150℃で2日間乾燥させる。
テレフタル酸(BDC)250.1g及びAl2(SO4)3×18H2O 292.9gをDMF 1257g中に懸濁させ、撹拌しながら130℃に24h加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをDMFで後洗浄する。ろ過ケークを、乾燥器中で120℃で2h乾燥させる。
(+)−カンファー二酸7.4g及びAl(SO4)3×18H2O 24gをDEF 520.5g中に懸濁させ、撹拌しながら130℃に4日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをDEF 2×100ml及びメタノール4×100mlで後洗浄する。ろ過ケークを、真空乾燥器中で200℃で16時間乾燥させる。429m2/gの表面積(ラングミュアによる)を有する生成物11.8gが生じる。回折図形(XRD)は図4に示されている。生成物1.5gを、ソックスレー装置中で沸騰メタノール中で16h抽出し、引き続き室温で真空中で乾燥させる。表面積は555m2/gに改善される。
1,2,3,4−ブタンテトラカルボン酸8.7g及びAl(SO4)3×18H2O 48gをDEF 520.5g中に懸濁させ、撹拌しながら130℃に4日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをDEF 2×100ml及びメタノール4×100mlで後洗浄する。ろ過ケークを、真空乾燥器中で200℃で16時間乾燥させる。518m2/gの表面積(ラングミュアによる)を有する生成物14.9gが生じる。
メルカプトコハク酸5.6g及びAl(NO3)3×9H2O 27.8gをDEF 520.5g中に懸濁させ、撹拌しながら130℃に3日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをDEF 2×100ml及びメタノール4×100mlで後洗浄する。ろ過ケークを、真空乾燥器中で200℃で16時間乾燥させる。488m2/gの表面積(ラングミュアによる)を有する生成物7.8gが生じる。回折図形(XRD)は図5に示されている。
1,4−ナフタレンジカルボン酸8g及びAl(NO3)3×9H2O 27.8gをDMF 520.5g中に懸濁させ、撹拌しながら130℃に3日間加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをメタノール3×100mlで後洗浄する。ろ過ケークを、真空乾燥器中で200℃で16時間乾燥させる。生成物8.7gが生じる。引き続いて、1.5gをソックスレー抽出器中で16h、メタノールで抽出し、真空中で室温で16h乾燥させる。
2,6−ナフタレンジカルボン酸4.9g及びMg(NO3)2×6H2O 8.16gをDEF 1686g中に懸濁させ、撹拌しながら105℃に24h加熱する。引き続いて、懸濁液をろ過し、ろ過ケークをまず最初にDMFで及び引き続きクロロホルムで後洗浄する。ろ過ケークを空気中で乾燥させる。生成物4.8gが生じる。乾燥させた生成物を、マッフル炉中で330℃で2日間か焼する。
1,2,4,5−ベンゼンテトラカルボン酸9.4g及びAl(NO3)3×9H2O 30.5gを、1l撹拌フラスコ中でDMF 520.5g中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で72h保持する。沈殿した生成物をろ別し、DMF 2×100ml及びメタノール4×100mlで洗浄し、真空乾燥器中で200℃で16h乾燥させる。最終的に、生成物をマッフル炉中で空気雰囲気下に330℃で72hか焼する。
メルカプトコハク酸13.6g及びAl(NO3)3×9H2O 67.6gを、2l撹拌フラスコ中でDMF 1246g中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で72h保持する。沈殿した生成物をろ別し、DMF 1×200ml及びメタノール3×200mlで洗浄し、真空乾燥器中で200℃で16h乾燥させる。
テレフタル酸239kg及びAl2(SO4)3×18H2O 279kgを、DMF 1500kg中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で18h保持する。沈殿した生成物をろ別し、アセトン3×500lで洗浄する。引き続いて、ろ過ケークを2回メタノール500l中に60℃で3h再懸濁させ、引き続きメタノールを再びろ別する。引き続きろ過ケークを、真空中で初めに50℃、後に100℃で乾燥させる。
イソフタル酸7.23g及びAlCl3×6H2O 7.0gを、撹拌フラスコ中でDMF 300ml中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で20.5h保持する。沈殿した生成物をろ別し、DMF 3×50ml及びメタノール4×50mlで洗浄し、真空乾燥器中で110℃で16h乾燥させる。
4,5−イミダゾールジカルボン酸5.17g及びAlCl3×6H2O 5.33gを、撹拌フラスコ中でDMF 300ml中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で20.5h保持する。沈殿した生成物をろ別し、DMF 3×50ml及びメタノール4×50mlで洗浄し、真空乾燥器中で110℃で72h乾燥させる。
シクロヘキサンジカルボン酸(シス/トランス混合物)1.33g及びAl(NO3)3×9H2O 5.95gを、撹拌フラスコ中でDMF 111g中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で17h保持する。沈殿した生成物をろ別し、DMF 2×50ml及びメタノール4×50mlで洗浄し、真空乾燥器中で130℃で16h乾燥させる。
2,6−ナフタレンジカルボン酸6.66g及びMg(NO3)2×6H2O 10.98gを、撹拌フラスコ中でDMF 137g中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で48h保持する。反応中に生じた水を、N2流と共に蒸留連結管(Destillationsbruecke)を経て追い出す。沈殿した生成物をろ別し、DMFで2回及びクロロホルムで2回洗浄する。ろ過ケークを、まず最初に室温で乾燥させ、最終的に250℃で48hか焼する。
5−t−ブチル−イソフタル酸4.95g及びCaCl2×6H2O 9.75gを、撹拌フラスコ中でDMF 312.3g中に懸濁させ、130℃に加熱し、撹拌しながらこれらの条件で20h保持する。沈殿した生成物をろ別し、DMF 1×50ml及びメタノール3×50mlで洗浄し、真空乾燥器中で200℃で10h乾燥させる。
Claims (13)
- 多孔質の金属有機骨格材料の製造方法であって、
非水系有機溶剤の存在で、少なくとも1つの金属化合物を、金属に配位結合できる少なくとも二座の少なくとも1つの有機化合物と反応させる工程を含み、その際に金属がBeII、MgII、CaII、SrII、BaII、AlIII、GaIII又はInIIIであり、かつ有機化合物が、酸素、硫黄及び窒素からなる群からその都度独立して選択され、有機化合物が金属に配位結合できる少なくとも2個の原子を有し、その際にこの反応を、撹拌しながら及び高くとも2bar(絶対)の圧力で行うことを特徴とする、
多孔質の金属有機骨格材料の製造方法。 - 反応を高くとも1230mbar(絶対)で、好ましくは大気圧で実施する、請求項1記載の方法。
- 反応を、付加的な塩基を用いずに行う、請求項1又は2記載の方法。
- 少なくとも二座の有機化合物がジカルボン酸、トリカルボン酸又はテトラカルボン酸である、請求項1から3までのいずれか1項記載の方法。
- 金属がAlIIIである、請求項1から4までのいずれか1項記載の方法。
- 非水系有機溶剤が、C1-6−アルカノール、DMSO、DMF、DEF、アセトニトリル、トルエン、ジオキサン、ベンゼン、クロロベンゼン、MEK、ピリジン、THF、酢酸エチルエステル、場合によりハロゲン化されたC1-200−アルカン、スルホラン、グリコール、NMP、γ−ブチロラクトン、脂環式アルコール、ケトン、シクロケトン、スルホレン又はそれらの混合物である、請求項1から5までのいずれか1項記載の方法。
- 反応後に、形成された骨格材料を有機溶剤で後処理する、請求項1から6までのいずれか1項記載の方法。
- 反応後にか焼工程を行う、請求項1から7までのいずれか1項記載の方法。
- 金属化合物が非イオン性であり、及び/又は金属カチオンに対する対イオンが、プロトン性溶剤から誘導されている、請求項1から8までのいずれか1項記載の方法。
- 請求項1から8までのいずれか1項記載の方法から得ることができる、多孔質の金属有機骨格材料。
- ラングミュアによる10m2/gを上回る比表面積を有する、請求項10記載の骨格材料。
- 少なくとも1つの物質をその貯蔵、分離、制御放出又は化学反応のために取り込むための、並びに担持材料としての、請求項10記載の多孔質の金属有機骨格材料の使用。
- 金属がAlIII又はMgIIであり、かつ骨格材料を水素貯蔵に使用する、請求項12記載の使用。
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JP7049595B2 (ja) | 2017-12-21 | 2022-04-07 | 株式会社豊田中央研究所 | アルミニウム有機構造体、それを用いた吸着材料、及びそれらの製造方法 |
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JP7180522B2 (ja) | 2019-04-22 | 2022-11-30 | トヨタ自動車株式会社 | 有機金属構造体 |
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JP5455368B2 (ja) | 2014-03-26 |
ES2356258T3 (es) | 2011-04-06 |
WO2007023134A1 (de) | 2007-03-01 |
CA2620113A1 (en) | 2007-03-01 |
EP1922299A1 (de) | 2008-05-21 |
CN101248034B (zh) | 2012-07-04 |
DE102005039623A1 (de) | 2007-03-01 |
ATE489354T1 (de) | 2010-12-15 |
US20100166644A1 (en) | 2010-07-01 |
US9878906B2 (en) | 2018-01-30 |
EP1922299B1 (de) | 2010-11-24 |
CA2620113C (en) | 2015-05-05 |
DE502006008395D1 (de) | 2011-01-05 |
CN101248034A (zh) | 2008-08-20 |
KR20080039985A (ko) | 2008-05-07 |
KR101422854B1 (ko) | 2014-07-24 |
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