TW201223962A - Process for producing a carbon-comprising composite - Google Patents
Process for producing a carbon-comprising composite Download PDFInfo
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- TW201223962A TW201223962A TW100131559A TW100131559A TW201223962A TW 201223962 A TW201223962 A TW 201223962A TW 100131559 A TW100131559 A TW 100131559A TW 100131559 A TW100131559 A TW 100131559A TW 201223962 A TW201223962 A TW 201223962A
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- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000002131 composite material Substances 0.000 title claims abstract description 23
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 32
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000011593 sulfur Substances 0.000 claims abstract description 23
- 239000012621 metal-organic framework Substances 0.000 claims abstract description 20
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 8
- 230000001681 protective effect Effects 0.000 claims abstract description 7
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000000197 pyrolysis Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 238000013270 controlled release Methods 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 238000007654 immersion Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 89
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 43
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- -1 Sr2 + Chemical compound 0.000 description 29
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 26
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 22
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 18
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 239000003205 fragrance Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JZKNMIIVCWHHGX-UHFFFAOYSA-N adamantane-1,2,2,3-tetracarboxylic acid Chemical compound C1C(C2)CC3CC1(C(=O)O)C(C(O)=O)(C(O)=O)C2(C(O)=O)C3 JZKNMIIVCWHHGX-UHFFFAOYSA-N 0.000 description 12
- XIEPJMXMMWZAAV-UHFFFAOYSA-N cadmium nitrate Inorganic materials [Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XIEPJMXMMWZAAV-UHFFFAOYSA-N 0.000 description 12
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000007824 aliphatic compounds Chemical class 0.000 description 9
- 150000001491 aromatic compounds Chemical class 0.000 description 9
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 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 8
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Inorganic materials [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 150000003628 tricarboxylic acids Chemical class 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 239000011148 porous material Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- QMKYBPDZANOJGF-UHFFFAOYSA-N trimesic acid Natural products OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 6
- 239000011592 zinc chloride Substances 0.000 description 6
- 235000005074 zinc chloride Nutrition 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
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- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HIHKYDVSWLFRAY-UHFFFAOYSA-N thiophene-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=CSC=1C(O)=O HIHKYDVSWLFRAY-UHFFFAOYSA-N 0.000 description 4
- 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
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- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000013148 Cu-BTC MOF Substances 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000013206 MIL-53 Substances 0.000 description 3
- 239000013132 MOF-5 Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
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- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 150000003463 sulfur Chemical class 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
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- 229910052719 titanium Inorganic materials 0.000 description 3
- NOSIKKRVQUQXEJ-UHFFFAOYSA-H tricopper;benzene-1,3,5-tricarboxylate Chemical compound [Cu+2].[Cu+2].[Cu+2].[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1.[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 NOSIKKRVQUQXEJ-UHFFFAOYSA-H 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
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- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- 241000723346 Cinnamomum camphora Species 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000013142 Zn-HKUST-1 Substances 0.000 description 2
- 239000013236 Zn4O(BTB)2 Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
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- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
- C04B38/0022—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof obtained by a chemical conversion or reaction other than those relating to the setting or hardening of cement-like material or to the formation of a sol or a gel, e.g. by carbonising or pyrolysing preformed cellular materials based on polymers, organo-metallic or organo-silicon precursors
-
- 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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
- B01J20/041—Oxides or hydroxides
-
- 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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
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Description
201223962 六、發明說明: 【發明所屬之技術領域】 本發明係關於一種製備含碳複合物之方法。本發明另外 係關於可以此方法獲得之複合物及包含此等複合物 極及其用途。 _
【先前技掏J 複合物係包括兩種或多種結合材料之材料。其精確化學 組成經常係未知,此使得其通常不得不以其製備方法及^ 始材料為特徵。 此等材料可具有無法自其起始材料預期(如果可以預期) 至相同程度之特性。 ’ 只例係自由銘離子及含氮配位基(1,3,5_三嗓4 6二 基卷甘賴,TTG)組成之多孔金屬錢架構製得之複合 物。此複合物係藉由熱解製得,且由於其氮含量而具有良 好的分離特性以分離c〇2/CH4(Y Shen等人,ckm
Commun. 46(2010),1308-1310) 〇 儘管存在先前技術中已知之複合物,但仍需要其他材 因此,本發明之一目標係提供此等材料及其製備方法。 【發明内容】 ' 該目標可藉由製備含碳複合物之方法實現,該方法包括 以下步驟: ⑷在保護性氣體氣氛下,使包含與至少-種金屬離子配 位之至少-種至少雙牙有機化合物之多孔金屬有機架構熱 158295.doc , 5 201223962 解’其中該至少一種、 v又牙有機化合物不含氮。 本發明方法可包括另一 ⑷中所獲得之複n^ ( )°此處’進行自於步舉 ° 乂σΡ份移除一或多種金屬組分。 匕金屬組分或此等金屬組分係來自 架構中之至少一種金屬離子之轉化。 金屬有機 二:卜’本發明方法可包括步驟⑷,其中用硫浸 (a)或(b)中所獲得之複合物。 顿 可藉由先前技術已知之方法進行該熱解。 較佳在至少5GG°C (較佳係至少6⑼。c )之溫度下進行步顿 ⑷中之熱解。更佳在崎至觸。。之溫度範圍内,甚至 更佳在600。〇至80(TC之範圍内,進行該熱解。 ,在保護性氣體氣氛下,進行製程步驟⑷。該保護性氣體 乳氛較佳係氮氣氛。其他—般已知之保護性氣體(如惰性 氣體)亦可。 多孔金屬有機架構係用作起始材料。此包括與至少一種 金屬離子配位之至少一種至少雙牙有機化合物,其中該至 少一種至少雙牙有機化合物不含氮。 此等金屬有機架構(MOF)係先前技術中已知且係描述於
(例如)US 5,648,508、ΕΡ-Α-0 790 253、M. O'Keeffe等人, J. Sol. State Chem.,152(2000),第 3至 20頁;H. Li等人, Nature 402,(1999),第 276 頁;M. Eddaoudi 等人,Topics in Catalysis 9, (1999),第 105 至 111 頁;β· Chen 等人, Science 291,(2001),第 1021 至 1023 頁;DE-A-101 li 230、DE-A10 2005 053430、W0-A 2007/054581、W0-A 158295.doc 201223962 2005/049892及 WO-A 2007/023134 中。 關於此等金屬有機架構之一具體群組,最近的文獻已描 述「限制」架構,其中由於該有機化合物之特定選擇,網 絡不無限延伸,而是形成多面體。A c Sudik等人,j Am.
Chem· Soc. 127(2005),711〇-7118摇述此等具體架構。在 本文中,此等將被稱為金屬有機多面體(M〇p)以區別其 等。 ’、 根據本發明之金屬有機架構包括孔隙,特定言之係微孔 及/或介孔。彳政孔係定義為具有2 nm或更小直徑之孔隙, 且介孔係定義為直徑在2至50 nm範圍内,在各情況下,對 應於在 Pure & Applied Chem. 57(1983),603-619,特定 έ之第606頁中提供之定義。可藉由吸附測量法(其根據 DIN 66131及/或DIN 66134,測定MOF在77 Κ下對氮氣之 吸收能力),檢測微孔及/或介孔之存在。 對於呈粉末形式之MOF而言,根據朗繆爾(Langmuir)模 型(0^66131、66134)算得之比表面積係大於10〇1112/§, 更佳係在300 m2/g以上’更佳係大於7〇〇 m2/g,甚至更佳 係大於800 m2/g,甚至更佳係大於1〇〇〇 m2/g,且特佳係大 於 1200 m2/g。 包含金屬有機架構之成形主體可具有相對較低的活性表 面積’但此較佳係大於150 m2/g,更佳係大於300 m2/g, 甚至更佳係大於700 m2/g。 根據本發明之架構中之金屬組分較佳係選自Ia、IIa、 Ilia、IVa至 Villa 及lb 至 乂几族。特佳係Mg、Ca、Sr、Ba、 s 158295.doc 201223962
Sc、Υ、Ln、Ti、Zr、Hf、V、Nb、Ta、Cr、Mo、W、 Mn、Re、Fe、Ro、〇s、c〇、Rh、lr、Ni、Pd、Pt、Cu、
Ag、An、Zn、Cd、Hg、A卜 Ga、In、ΊΠ、Si、Ge、Sn、
Pb、As、Sb及Bi,其中Ln表示鋼系元素。 鋼系元素係 La、Ce、Pr、Nd、Pm、Sm、En、Gd、Tb、 Dy、Ho、Er、Tm、Yb。 就此等元素之離子而言,尤其可述及Mg2+、Ca2+、Sr2 + 、Ba2+、Sc3+、Y3+、Ln3+、Ti4+、Zr4+、Hf4.、V4+、V3 + 、V2+、Nb3+、Ta3+、Cr3+、Mo3+、W3+、Mn3+、Mn2 + 、Re3+、Re2+、Fe3+、Fe2+ ' RU3+、ru2+、〇s3+、〇s2 + 、Co3+、Co2+、Rh2+、Rh+、Ir2+、Ir+、Ni2+、Ni+、Pd2 + 、Pd+、Pt2+、Pt+、Cu2+、Cu+、Ag+、Au+、Zn2+、Cd2 + 、Hg2+、Al3+ ' Ga3+、ln3+、Tl3+、Si4+、Si2+、Ge4+、 Ge2+、Sn4+、Sn2+、Pb4+、Pb2+、As5+、As3+、As+、Sb5 + 、Sb3+、Sb+、Bi5+、Bi3+及Bi+。 更特定言之,以 Mg、A1、Zr、Ti、V、Cr、Mo、Fe、 Co、Cu、Ni ' Zn較佳。以 A1、Ti、Mg、Fe、Cu及 Zn 更 佳。以Mg、A卜Cu及Zn極佳。 術s吾「至少雙牙有機化合物」係指包括至少一個可與特 定金屬離子形成至少兩個配位鍵及/或與兩個或多個(較佳 係兩個)金屬原子中之各者形成一個配位鍵之官能基之有 機化合物。 關於可形成上述配位鍵之官能基,舉例而言,尤其可述 及下列官能基:-C〇2H、-cs2h、-no2、-B(OH)2 ' -so3h、 158295.doc ,6 - c 201223962 -Si(〇H)3、-Ge(〇H)3、_Sn(〇H)3、-Si(SH)4、-Ge(SH)4、 -Sn(SH)3、-P〇3H、-As03H、-As04H、-P(SH)3、-As(SH)3 -ch(rsh)2、-c(rsh)3-ch(roh)2、-C(ROH)3,其中 R較 佳係(例如)具有1、2、3、4或5個碳原子之伸烷基(例如, 亞曱基Μ申乙基、伸正丙基、伸異丙基、伸正丁基、伸異 丁基、伸第二丁基、或伸正戊基),或包含個芳族環 (例如,2個C6%)之芳基,該等環可視需要經稠合或可在各 隋况下相互獨A地經至少一個取代基適當取代及/或可在 各情況下相互獨立地包括至少一個雜原子(如〇及/或s)。 在同樣較佳的實施例中,可述及其中不存在上述自由基&之 B月b基此荨基團尤其係CH(SH)2、-C(SH)3、-CH(OH)2、 或-C(OH)3。 該至少兩個官能基原則上可結合至任何適宜的有機化合 物’只要確保具有此等官能基之有機化合物能形成配位鍵 及產生架構即可。 包含該至少兩個官能基之有機化合物較佳係衍生自飽和 或不飽和脂族化合物或芳族化合物或脂族及芳族化合物。 該脂族化合物或該脂族及芳族化合物之脂族部份可係直 鏈及/或分支鏈及/或環狀,且每分子化合物具有複數個環 亦可。該脂族化合物或該脂族及芳族化合物之脂族部份更 佳包括1至15個’更佳係!至14個,更佳係】至13個,更佳 係1至12個,更佳係!至u個且特佳係!至個碳原子,例 如1 2、3、4、5、6、7、8、9或1〇個碳原子。在本文 中,尤其以T烷、類金剛烷、乙炔、乙烯或丁二烯特佳。
S I58295.doc 201223962 K族化合物㈣芳族及脂族化合物之芳 :=,例如2、3、4或5個環,其中該等獨: ί及/或至少兩個環係經稍合。該芳族化合物或該脂族及 芳私化合物之芳族部份特佳 " ' 2個产^ 行^、有1、2或3個環,其中以】或 Γ:;?:。、所述化合物之各環亦可獨立地包括至少-個 芳族0、S B、P、Sl、^’較佳係Ν、0及/或S)。該 2化,物或該芳族及脂族化合物之芳族部份更佳包括ι 或2個。環,其中該等環可單獨存在或以稠合形式存在。 尤其可述及苯、萘及/或聯苯作為芳族化合物。 該至少雙牙有機化合物更佳係脂族或芳族、無環或環狀 烴’其具有!至18個,較佳H0個且特定言之_碳原子 且另外僅具有2、3或4個致基作為官能基。 例如,該至少雙牙有機化合物係衍生自二羧酸,如草 酸、琥轴酸、酒石酸、M_丁烷二缓酸、丨,4_丁烯二羧 酸' 4-側氧基哌喃_2,6_二羧酸、!,6•己烷二 «、一烧二缓酸、…院二㈣、十七二 羧酸、乙炔二羧酸、1,2-苯二羧酸、丨,3_苯二羧酸、-丁 二烯-M-二羧酸、i,4-苯二羧酸、p—笨二羧酸、噻吩_3,4_ 二羧酸、四氫吡喃-4,4-二羧酸、並_3,9_二羧酸、花二羧 酸、PlUri〇lE 200-二羧酸、3,6-二氧雜辛烷二羧酸、3,5_環 己二烯-1,2-二羧酸、辛二酸、戊烷_3,3_羧酸、丨,^二萘基 一羧酸、聚四氫呋喃-250-二羧酸、1,4,5,6,7,7_六氯_5_降 冰片稀-2,3-二敌酸、苯基節滿二後酸、丨,4_環己烧二羧 酸、萘-1,8-二羧酸、2-笨曱醯基笨4,3-:羧酸、3,6,9_三 158295.doc 201223962 氧雜Η 烧二竣酸、經基二苯甲嗣二繞酸、卩1111*丨〇1£ 300-二 羧酸、pluriol Ε 400-二羧酸、pluri〇l Ε 600-二羧酸、ι,4- 萘二羧酸、2,6-萘二羧酸、ι,3-金剛烷二羧酸' i,8_萘二羧 酸、2,3-萘二竣酸、8-甲氧基-2,3-萘二竣酸、8-硫-2,3-萘 二羧酸、蒽-2,3-二羧酸、2,,3,-二苯基-對莊烯基_4,4"-二羧 酸、(二苯基醚)-4,4"-二羧酸、4(ih)-側氧基硫咣烯_2,二 羧酸、5-第三丁基_ι,3-笨二羧酸、4-環己烯_ι,2-二羧酸、 三十六烷二羧酸、十四烷二羧酸、丨,7_庚烷二羧酸、5_羥 基-1,3-苯二羧酸、2,5-二羥基-1,4-二羧酸、呋喃_2,5_二羧 酸、1-壬烯-6,9-二羧酸、二十烯二羧酸、4,4,_二羥基二苯 基甲烷-3,3·-二羧酸、環己稀_2,3_二羧酸、2,4_二氯二苯曱 酮-2’,5’-二羧酸、丨,3·苯二羧酸、蒽醌_丨,5_二羧酸、2_硝基 苯-1’4_二羧酸、庚烷-1,7·二羧酸、環丁烷-1,1-二羧酸、 1,14-十四烷二羧酸、5,6_去氫降冰片烷_2,3_二羧酸或樟腦 二羧酸。 °亥至y又牙有機化合物甚至更佳係如上舉例而言所述及 之二羧酸中之一者。 該至少雙牙有機化合物可(例如)衍生自三羧酸,如 2-羥基-1,2,3-丙烷三羧酸、…u,4_苯三羧酸、 1,2,4-丁烷二羧酸、2_膦醯基丁烷三羧酸、1,3,^苯 三羧酸、1-殘基+2,3-丙烷三羧酸、5_乙醯基_3_胺基·6_甲 基笨1,2,4 —羧酸、丨,】,;^丙烷三羧酸或金精三羧酸。 肩至v又牙有機化合物甚至更佳係如上舉例而言所述及 之三羧酸中之一者。 S. 158295.doc , 201223962 衍生自四叛酸之至少雙牙有機化合物之實例係: ι,ι-二氧離子基茈并[112_BCD]噻吩_3 4,9,1〇四羧酸、 花四缓酸(如花_3,4,9,1〇-四缓酸或(花1,12-石風)_:3,4,9,1()_㈣ 酸)、丁烷四羧酸(如丁烷四羧酸或内消旋,馭 烷四羧酸)、癸烷_2,4,6,8-四羧酸、1,4,7,10’13,16-六氧雜 環十八烷-2,3,11,12-四羧酸、ι,2,4,5-苯四羧酸、^丨丨12 十二烧四竣酸、己烷四羧酸、ι,2,7,8辛烷四幾 酸、1,4,5,8-萘四羧酸、mi、癸烷四羧酸、二笨曱鲖 缓酸、3,3’,4,4’·:笨甲鋼四叛酸、四氫吱喃四敌酸或環戊 炫四羧酸(如環戊烷],2,3,4_四羧酸)〇 " 該至少雙牙有機化合物甚至更佳係如上舉例而言所述及 之四綾酸中之一者。 以視需要至少經單取代之具W、2、3、4或更多個環之 芳族二羧酸、三羧酸或四羧酸極佳,其中該等環各可包括 至少一個雜原子且兩個或更多個環可包括相同或不同的雜 原子。較佳係(例如)單環二羧酸、單環三羧酸、單環四羧 酸、二環二羧酸、二環三羧酸、二環四羧酸、三環二綾 酸、三環三羧酸、三環四羧酸、四環二羧酸、四環三羧酸 及/或四環四羧酸。適宜的雜原子係(例如)〇、s、B、p且 較佳的雜原子尤其係8及/或〇。關於適宜的取代基,可尤 其述及-0Η、硝基、烷基或烷氧基。 以使用乙炔二羧酸(ADC)、樟腦二羧酸、富馬酸、琥珀 酸、苯二羧酸(如鄰苯二曱酸、間苯二曱酸、對苯二曱酸 (BDC))、萘二羧酸(NDC)、聯笨二羧酸(如4,4,_聯苯二羧酸 158295.doc 201223962 (BPDC))、苯三羧酸(如ι,2,3-、1,2,4-苯三羧酸或i,3,5-苯 二羧酸(BTC))、苯四羧酸、金剛烷四羧酸(ATC)、金剛烷 二苯甲酸鹽(ADB)、苯三苯甲酸鹽(BTB)、甲烷四苯曱酸 鹽(MTB)、金剛烷四苯甲酸鹽或二羥基對苯二甲酸(如2,5_ 二經基對苯二甲酸(DHBDC))、四氫芘·2,7-二羧酸 (HPDC)、聯苯四羧酸(BPTC)作為至少雙牙有機化合物特 別佳。 尤其以鄰苯二甲酸、間苯二甲酸、對苯二曱酸、2,6_萘 二羧酸、1,4-萘二羧酸、丨,5-萘二羧酸、苯三羧酸、 1,2,4-苯三羧酸、苯三羧酸、丨,2,4,弘苯四羧酸、富馬 酋夂%本一叛酸鹽、1,5 -及2,6 -萘二致酸、第三丁基間苯 一甲酸、二罗里基苯甲酸、BTB、HPDC、BPTC極佳。 除此等至少雙牙有機化合物以外,該金屬有機架構亦可 包括或多種單牙配位基及/或非衍生自二幾酸、三缓酸 或四鲮酸之一或多種至少雙牙配位基。 除此等至少雙牙有機化合物以外,該金屬有機架構亦可 包括一或多種單牙配位基。 適用於製備該金屬有機架構之溶劑尤其係乙醇、二甲基 曱醯胺、甲苯、甲醇、氯苯、二乙基甲醯胺、二甲基亞 砜、水、過氧化氫、甲胺、氫氧化鈉溶液、N_甲基吡咯啶 酮趟、乙腈、节基氣、三乙胺、乙二醇及其混合物。用於 製MOF之其他金屬離子、至少雙牙有機化合物及溶劑尤其 係描述於US-A 5,648,508或 DE-A 101 11 230 中。 可藉由選擇適宜的配位基及/或該至少雙牙有機化合 s 158295.doc 201223962 物,控制該金屬有機架構之孔徑。一般而言,該有機化合 物越大,孔徑越大。基於晶體材料,該孔徑較佳係0.2 nm 至30 nm,特佳係0.3 nm至3 nm。 金屬有機架構之實例係如下所示。除該架構之名稱以 外,指示該金屬及該至少雙牙配位基、該溶劑及單元參數 (角α、β及γ,及以A計之間距A、B及C)。藉由X-射線繞射 法,測定後者。 MOF-n 組分 莫耳比 M + L 溶劑 a β Y a b c 空間群 MOF-O Zn(N〇3)2 · 6H20 H3(BTC) 乙醇 90 90 120 16.711 16.711 14.189 P6(3)/ Mem MOF-2 Zn(N〇3)2 · 6H20 (0.246 mmol H2(BDC) 0.241 mmol) DMF 曱苯 90 102.8 90 6.718 15.49 12.43 P2(l)/n MOF-3 Zn(N〇3)2 · 6H20 (1.89 mmol) H2(BDC) (1.93 mmol) DMF MeOH 99.72 111.11 108.4 9.726 9.911 10.45 P-1 MOF-4 Zn(N〇3)2 · 6H20 (1.00 mmol) H3(BTC) (0.5 mmol) 乙醇 90 90 90 14.728 14.728 14.728 P2(l)3 MOF-5 Zn(N03)2 · 6H20 (2.22 mmol) H2(BDC) (2.17 mmol) DMF 氯苯 90 90 90 25.669 25.669 25.669 Fm-3m MOF-38 Zn(N〇3)2 · 6H20 (0.27 mmol) H3(BTC) (0.15 mmol) DMF 氣苯 90 90 90 20.657 20.657 17.84 14cm 158295.doc -12- 201223962 MOF-31 Zn(ADC)2 Zn(N〇3)2 · 6H20 0.4 mmol H2(ADC) 0.8 mmol 乙醇 90 90 90 10.821 10.821 10.821 Pn(-3)m MOF-12 Zn2(ATC) Zn(N03)2 . 6H20 0.3 mmol H4(ATC) 0.15 mmol 乙醇 90 90 90 15.745 16.907 18.167 Pbca MOF-20 ZnNDC Zn(N〇3)2 . 6H20 0.37 mmol H2NDC 0.36 mmol DMF 氯苯 90 92.13 90 8.13 16.444 12.807 P2(l)/c MOF-37 Zn(N〇3)2 · 6H20 0.2 mmol H2NDC 0.2 mmol DEF 氯苯 72.38 83.16 84.33 9.952 11.576 15.556 P-1 MOF-8 Tb2(ADC) Tb(N03)3 . 5H20 0.10 mmol H2ADC 0.20 mmol DMSO MeOH 90 115.7 90 19.83 9.822 19.183 C2/c MOF-9 Tb2(ADC) Tb(N03)3 . 5H20 0.08 mmol H2ADB 0.12 mmol DMSO 90 102.09 90 27.056 16.795 28.139 C2/c MOF-6 Tb(N03)3 · 5H20 0.30 mmol H2(BDC) 0.30 mmol DMF MeOH 90 91.28 90 17.599 19.996 10.545 P21/c MOF-7 rb(N03)3 · 5H20 3.15 mmol H2(BDC) 3.15 mmol h2o 102.3 91.12 101.5 6.142 10.069 10.096 P-1 MOF-69A 乙n(N03)2 · 5H20 3.083 mmol M'bpdc ).041 mmol DEF H2〇2 MeNH2 ?0 111.6 90 23.12 20.92 12 C2/c MOF-69B ( / ζη(Ν〇3)2 · 5H20 ).083 mmol ?,6-NDC ).041 mmol DEF H2〇2 VteNH2 )0 ?5.3 ?0 20.17 18.55 12.16 Z2/c s 158295.doc -13 - 201223962 MOF-ll Cu2(ATC) Cu(N〇3)2 · 2.5H20 0.47 mmol H2ATC 0.22 mmol H20 90 93.86 90 12.987 11.22 11.336 C2/c MOF-ll Cu2(ATC) 無水 90 90 90 8.4671 8.4671 14.44 P42/ mmc MOF-14 Cu3(BTB) Cu(N〇3)2 · 2.5H20 0.28 mmol H3BTB 0.052 mmol h2o DMF EtOH 90 90 90 26.946 26.946 26.946 lm-3 MOF-32 Cd(ATC) Cd(N〇3)2 · 4H20 0.24 mmol h4atc 0.10 mmol H20 NaOH 90 90 90 13.468 13.468 13.468 P(-4)3m MOF-33 Zn2(ATB) ZnCl2 0.15 mmol H4ATB 0.02 mmol H20 DMF EtOH 90 90 90 19.561 15.255 23.404 Imma MOF-34 Ni(ATC) Ni(N〇3)2 · 6H20 0.24 mmol h4atc 0.10 mmol H20 NaOH 90 90 90 10.066 11.163 19.201 P2i2i2i MOF-36 Zn2(MTB) Zn(N〇3)2 · 4H20 0.20 mmol H4MTB 0.04 mmol H20 DMF 90 90 90 15.745 16.907 18.167 Pbca MOF-39 Zn30(HBT B) Zn(N03)2 4H20 0.27 mmol H3BTB 0.07 mmol H20 DMF EtOH 90 90 90 17.158 21.591 25.308 Pnma NO305 FeCl2.4H20 5.03 mmol 曱酸 86.90 mmol DMF 90 90 120 8.2692 8.2692 63.566 R"3c NO306A FeCl2.4H20 5.03 mmol 曱酸 86.90 mmol DEF 90 90 90 9.9364 18.374 18.374 Pbcn 158295.doc •14- 201223962 N029 MOF-O 類似 Mn(Ac)2 . 4H20 0.46 mmol H3BTC 0.69 mmol DMF 120 90 90 14.16 33.521 33.521 P-1 BPR48 A2 Zn(N〇3)2 6H20 0.012 mmol H2BDC 0.012 mmol DMSO 曱苯 90 90 90 14.5 17.04 18.02 Pbca BPR69 B1 Cd(N03)2 4H20 0.0212 mmol H2BDC 0.0428 mmol DMSO 90 98.76 90 14.16 15.72 17.66 Cc BPR92 A2 C〇(N〇3)2 · 6H20 0.018 mmol H2BDC 0.018 mmol NMP 106.3 107.63 107.2 7.5308 10.942 11.025 PI BPR95 C5 Cd(N03)2 4H20 0.012 mmol H2BDC 0.36 mmol NMP 90 112.8 90 14.460 11.085 15.829 P2(l)/n CuC^HtOe Cll(N〇3)2 · 2.5H20 0.370 mmol H2BDC(OH)2 0.37 mmol DMF 氯苯 90 105.29 90 15.259 14.816 14.13 P2(l)/c M(BTC) MOF-O 類似 Co(S04)H20 0.055 mmol H3BTC 0.037 mmol DMF 類似於MOF-O Tb(C6H4〇6) Tb(N03)3 · 5H20 0.370 mmol H2(C6H4〇6) 0.56 mmol DMF 氯苯 104.6 107.9 97.147 10.491 10.981 12.541 P-1 Zn(C204) ZnCl2 0.370 mmol 草酸 0.37 mmol DMF 氣苯 90 120 90 9.4168 ?.4168 8.464 P(-3)lm Co(CHO) :〇(N〇3)2 · 5H20 1043 mmol 曱酸 ί.60 mmol DMF ?0 51.32 ?0 11.328 10.049 14.854 P2(l)/n 158295.doc -15· 201223962
Cd(CHO) Cd(N03)2 · 4H20 0.185 mmol 曱酸 0.185 mmol DMF 90 120 90 8.5168 8.5168 22.674 R-3c Cu(C3H204) Cu(N〇3)2 · 2.5H20 0.043 mmol 丙二酸 0.192 mmol DMF 90 90 90 8.366 8.366 11.919 P43 ΖΠ6 (NDC)s MOF-48 Zn(N〇3)2 · 6H20 0.097 mmol 14NDC 0.069 mmol DMF 氣苯 H2〇2 90 95.902 90 19.504 16.482 14.64 C2/m MOF-47 Zn(N〇3)2 . 6H20 0.185 mmol h2(bdc[ch3]4) 0.185 mmol DMF 氯苯 H2〇2 90 92.55 90 11.303 16.029 17.535 P2(l)/c M025 Cll(N〇3)2 · 2.5H20 0.084 mmol BPhDC 0.085 mmol DMF 90 112.0 90 23.880 16.834 18.389 P2(l)/c Cu-Thio Cu(N〇3)2 . 2_5H20 0.084 mmol 噻吩二羧酸 0.085 mmol DEF 90 113.6 90 15.4747 14.514 14.032 P2(l)/c C1BDC1 Cu(N〇3)2 · 2.5H20 0.084 mmol H2(BDCC12) 0.085 mmol DMF 90 105.6 90 14.911 15.622 18.413 C2/c MOF-101 Cll(N〇3)2 · 2.5H20 0.084 mmol BrBDC 0.085 mmol DMF 90 90 90 21.607 20.607 20.073 Fm3m Zn3(BTC)2 ZnCl2 0.033 mmol H3BTC 0.033 mmol DMF EtOH 添加驗 90 90 90 26.572 26.572 26.572 Fm-3m 158295.doc • 16- 201223962 MOF-j Co(CH3C02)2 • 4H20 (1.65 mmol) H3(BZC) (0.95 mmol) h2o 90 112.0 90 17.482 12.963 6.559 C2 MOF-n Zn(N〇3)2 · 6H20 H3(BTC) 乙醇 90 90 120 16.711 16.711 14.189 P6(3)/mc m PbBDC Pb(N03)2 (0.181 mmol) H2(BDC) (0.181 mmol) DMF 乙醇 90 102.7 90 8.3639 17.991 9.9617 P2(l)/n Znhex Zn(N〇3)2 · 6H20 (0.171 mmol) H3BTB :0.114 mmol) DMF 對二甲 苯 乙醇 90 90 120 37.1165 37.117 30.019 P3(l)c AS16 FeBr2 0.927 mmol H2(BDC) 0.927 mmol 無水 DMF 90 90.13 90 7.2595 8.7894 19.484 P2(l)c AS27-2 FeBr2 0.927 mmol H3(BDC) 0.464 mmol 無水 DMF 90 90 90 26.735 26.735 26.735 Fm3m AS32 FeCl3 1.23 mmol H2(BDC) 1.23 mmol 無水 DMF 乙醇 90 90 120 12.535 12.535 18.479 P6(2)c AS54-3 FeBr2 0.927 BPDC 0.927 mmol 無水 DMF 正丙醇 90 109.98 90 12.019 15286 14.399 C2 AS61-4 FeBr2 0.927 mmol m-BDC 0.927 mmol 無水°比 啶 90 90 120 13.017 13.017 14.896 P6(2)c AS68-7 FeBr2 0.927 mmol m-BDC 1.204 mmol 無水 DMF 吡啶 90 90 90 18.3407 10.036 18.039 Pca2i Zn(ADC) Zn(N〇3)2 · 6H20 0.37 mmol H2(ADC) 0.36 mmol t)MF 氣苯 90 99.85 90 16.764 9.349 9.635 C2/c c 158295.doc -17- 201223962 MOF-12 Zn2(ATC) Zn(N〇3)2 · 6H20 0.30 mmol H4(ATC) 0.15 mmol 乙醇 90 90 90 Ϊ 5.745 16.907 18.167 Pbca MOF-20 ZnNDC Zn(N〇3)2 · 6H20 0.37 mmol H2NDC 0.36 mmol DMF 氯苯 90 92.13 90 8.13 16.444 12.807 P2(l)/c MOF-37 Zn(N03)2 · 6H20 0.20 mmol H2NDC 0.20 mmol DEF 氣苯 72.38 83.16 84.33 9.952 11.576 15.556 P-1 Zn(NDC) (DMSO) Zn(N〇3)2 · 6H20 h2ndc DMSO 68.08 75.33 88.31 8.631 10.207 13.114 P-1 Zn(NDC) Zn(N〇3)2 . 6H20 h2ndc 90 99.2 90 19.289 17.628 15.052 C2/c Zn(HPDC) Zn(N〇3)2 · 4H20 0.23 mmol H2(HPDC) 0.05 mmol DMF H20 107.9 105.06 94.4 8.326 12.085 13.767 P-1 Co(HPDC) C〇(N〇3)2 · 6H20 0.21 mmol H2(HPDC) 0.06 mmol DMF h2o/乙 醇 90 97.69 90 29.677 9.63 7.981 C2/c Zn3(PDC)25 Zn(N03)2 · 4H20 0.17 mmol H2(HPDC) 0.05 mmol pMF/ CIBz h2o/ TEA 79.34 80.8 85.83 8.564 14.046 26.428 P-1 Cd2 (TPDC)2 Cd(N03)2 · 4H20 0.06 mmol H2(HPDC) 0.06 mmol 甲醇/ CHP h2o 70.59 72.75 87.14 10.102 14.412 14.964 P-1 Tb(PDC)IS Tb(N03)3 . 5H20 0.21 mmol H2(PDC) 0.034 mmol DMF H20/ 乙醇 109.8 103.61 100.14 9.829 12.11 14.628 P-1 158295.doc -18- 201223962
ZnDBP Zn(N〇3)2 . 6H20 0.05 mmol ; 磷酸二苄酯 0.10 mmol MeOH 90 93.67 90 9.254 10.762 27.93 P2/n Zn3(BPD C) ZnBr2 0.021 mmol 4,4'BPDC 0.005 mmol DMF 90 102.76 90 11.49 14.79 19.18 P21/n CdBDC Cd(N03)2 · 4H20 0.100 mmol H2(BDC) 0.401 mmol DMF N^Si〇3 (水溶液) 90 95.85 90 11.2 11.11 16.71 P21/n Cd-mBDC Cd(N03)2 · 4H20 0.009 mmol ^2(mBDC) 0.018 mmol DMF MeNH2 90 101.1 90 13.69 18.25 14.91 C2/c Z114OBN DC Zn(N〇3)2 · 6H20 0.041 mmol BNDC DEF MeNH2 H2〇2 90 90 90 22.35 26.05 59.56 Fmmm 甲酸鹽 Ce(N03)3 · 6H20 0.138 mmol 曱酸 0.43 mmol h2o 乙醇 90 90 120 10.668 10.667 4.107 R-3m FeCl2 · 4H20 5.03 mmol 曱酸 86.90 mmol DMF 90 90 120 8.2692 8.2692 63.566 R-3c teCl2 · 4H20 5.03 mmol 甲酸 86.90 mmol DEF 90 90 90 9.9364 18.374 18.374 Pbcn FeCl2 · 4H20 5.03 mmol 曱酸 86.90 mmol DEF 90 90 90 8.335 8.335 13.34 P-31c NO330 teCl2 · 4H20 0.50 mmol 曱酸 8.69 mmol 甲醯胺 90 90 90 8.7749 11.655 8.3297 Prina 158295.doc -19- 201223962 Ν0332 FeCl2 · 4Η20 DIP 90 90 90 10.0313 18.808 18.355 Pbcn 0.50 mmol 曱酸 8.69 mmol N0333 Fe Cl2 · 4H20 0.50 mmol 曱酸 8.69 mmol DBF 90 90 90 45.2754 23.861 12.441 Cmcm N0335 FeCl2 · 4H20 0.50 mmol 曱酸 8.69 mmol CHF 90 91.372 90 11.5964 10.187 14945 p21/n N0336 FeCl2 · 4H20 0.50 mmol 甲酸 8.69 mmol MFA 90 90 90 11.7945 48.843 8.4136 Pbcm N029 MOF-O 類似 Mn(Ac)2 · 4H20 0.46 mmol h3btc 0.69 mmol DMF 120 90 90 14.16 33.521 33.521 P-1 Mn(Hfac)2 (02CC6H5) Mn(Ac)2 · 4H20 0.46 mmol Hfac 0.92 mmol 聯吡啶 0.46 mmol 乙醚 90 95.32 90 9.572 17.162 14.041 C2/c BPR43G2 Zn(N〇3)2 · 6H20 0.0288 mmol H2BDC 0.0072 mmol DMF CH3CN 90 91.37 90 17.96 6.38 7.19 C2/c BPR48A2 Zn(N〇3)2 6H20 0.012 mmol h2bdc 0.012 mmol DMSO 甲笨 90 90 90 14.5 17.04 18.02 Pbca BPR49B1 Zn(N〇3)2 6H20 0.024 mmol H2BDC 0.048 mmol DMSO 甲醇 90 91.172 90 33.181 9.824 17.884 C2/c BPR56E1 Zn(N03)2 6H20 0.012 mmol H2BDC 0.024 mmol DMSO 正丙醇 90 90.096 90 14.5873 14.153 17.183 P2(l)/n 158295.doc -20- (Τ 201223962 BPR68D10 Zn(N03)2 6H20 0.0016 mmol H3BTC 0.0064 mmol DMSO 苯 90 95.316 90 10.0627 10.17 16.413 P2(l)/c BPR69B1 Cd(N03)2 4H20 0.0212 mmol H2BDC 0.0428 mmol DMSO 90 98.76 90 14.16 15.72 17.66 Cc BPR73E4 Cd(N03)2 · 4H20 0.006 mmol H2BDC 0.003 mmol DMSO 曱苯 90 92.324 90 8.7231 7.0568 18.438 P2(l)/n BPR76D5 z_o3)2 6H20 0.0009 mmol H2BzPDC 0.0036 mmol DMSO 90 104.17 90 14.4191 6.2599 7.0611 Pc BPR80B5 Cd(N03)2 . 4H20 0.018 mmol H2BDC 0.036 mmol DMF 90 115.11 90 28.049 9.184 17.837 C2/c BPR80H5 Cd(N03)2 · 4H20 0.027 mmol H2BDC 0.027 mmol DMF 90 119.06 90 11.4746 6.2151 17.268 P2/c BPR82C6 Cd(N03)2 · 4H20 0.0068 mmol H2BDC 0.202 mmol DMF 90 90 90 9.7721 21.142 27.77 Fdd2 BPR86C3 Co(N03)2 · 6H20 0,0025 mmol H2BDC 0.075 mmol DMF 90 90 90 18.3449 10.031 17.983 Pca2(l) BPR86H6 Cd(N03)2 · 6H20 0.010 mmol H2BDC O.OlOmmo ; DMF 80.98 89.69 83.412 9.8752 10.263 15.362 P-1 Co(N03)2 · 6H20 MMP 106.3 107.63 107.2 7.5308 10.942 11.025 PI BPR95A2 乙 n(N03)2 5H20 1012 mmol H2BDC 1012 mmol NfMP 90 102.9 90 7.4502 13.767 12.713 P2(l)/c s 158295.doc -21 - 201223962 CUC6F404 Cu(N〇3)2 · 2.5H20 0.370 mmol H2BDC(OH)2 0.37 mmol DMF 氯苯 90 98.834 90 10.9675 24.43 22.553 P2(l)/n 曱酸Fe FeCl2 · 4H20 0.370 mmol 甲酸 0.37 mmol DMF 90 91.543 90 11.495 9.963 14.48 P2(l)/n 曱酸Mg Mg(N03)2 · 6H20 0.370 mmol 曱酸 0.37 mmol DMF 90 91.359 90 11.383 9.932 14.656 P2(l)/n MgCeH^Oe Mg(N03)2 · 6H20 0.370 mmol H2BDC(OH)2 0.37 mmol DMF 90 96.624 90 17.245 9.943 9.273 C2/c Zn C2H4BDC MOF-38 ZnCl2 0.44 mmol CBBDC 0.261 mmol DMF 90 94.714 90 7.3386 16.834 12.52 P2(l)/n MOF-49 ZnCl2 0.44 mmol tn-BDC 0.261 mmol I)MF CH3CN 90 93.459 90 13.509 11.984 27.039 P2/c MOF-112 Cu(N〇3)2 · 2.5H20 0.084 mmol o-Br-m-BDC 0.085 mmol DMF 乙醇 90 107.49 90 b.3241 21.297 18.069 C2/c MOF-109 Cu(N〇3)2 · 2_5H20 0.084 mmol KDB 0.085 mmol DMF 90 111.98 90 23.8801 16.834 18.389 P2(l)/c MOF-111 Cu(N〇3)2 · 2_5H20 0.084 mmol o-BrBDC 0.085 mmol DMF 乙醇 90 102.16 90 10.6767 18.781 21.052 C2/c MOF-110 Cll(N〇3)2 · 2.5H20 0.084 mmol 噻吩二羧酸 0.085 mmol DMF 90 90 120 20.0652 20.065 20.747 R-3/m -22- 158295.doc 201223962 MOF-107 Cu(N〇3)2 · 2.5H20 0,084 mmol 噻吩二羧酸 0.085 mmol DEF 104.8 97.075 95.206 11.032 18.067 18.452 P-1 MOF-108 Cll(N〇3)2 · 2.5H20 0.084 mmol 噻吩二羧酸 0.085 mmol DBF/ 曱醇 90 113.63 90 15.4747 14.514 14.032 C2/c MOF-102 Cu(N〇3)2 · 2.5H20 0.084 mmol H2(BDCC12) 0.085 mmol DMF 91.63 106.24 112.01 9.3845 10.794 10.831 P-1 Clbdcl Cll(N〇3)2 · 2.5H20 0.084 mmol H2(BDCC12) 0.085 mmol DEF 90 105.56 90 14.911 15.622 18.413 P-1 Tb(BTC) Tb(N03)3 · 5H20 0.033 mmol H3BTC 0.033 mmol DMF 90 106.02 90 18.6986 11.368 19.721 Zn3(BTC)2 Honk ZnCl2 0.033 mmol H3BTC 0.033 mmol DMF 乙醇 90 90 90 26.572 26.572 26.572 ?m-3m Zn4〇(ND C) Zn(N〇3)2 · 4H20 0.066 mmol 14NDC 0.066 mmol DMF 乙醇 90 90 90 41.5594 18.818 17.574 aba2 IRMOF-2 Zn(N03)2 · 4H20 0.160 mmol o-Br-BDC 0.60 mmol DEF 90 90 90 25.772 25.772 25.772 "m-3m 1RMOF-4 乙n(N〇3)2 · 4H20 0.11 mmol [c3h7o]2- BDC [).48 mmol DEF 90 90 90 25.849 25.849 25.849 7m-3m
S 158295.doc •23 201223962 IRMOF-5 Zn(N〇3)2 · 4H20 0.13 mmol [C5H„0]2-BDC 0.50 mmol DEF 90 90 90 12.882 12.882 12.882 Pm-3m IRMOF-6 Zn(N〇3)2 · 4H20 0.20 mmol [C2H4]-BDC 0.60 mmol DEF 90 90 90 25.842 25.842 25.842 Fm-3m IRMOF-7 Zn(N〇3)2 . 4H20 0.07 mmol 1,4NDC 0.20 mmol DEF 90 90 90 12.914 12.914 12.914 Pm-3m IRMOF-8 Zn(N〇3)2 · 4H20 0.55 mmol 2,6NDC 0.42 mmol DEF 90 90 90 30.092 30.092 30.092 Fm-3m IRMOF-9 Zn(N〇3)2 · 4H20 0.05 mmol BPDC 0.42 mmol DEF 90 90 90 17.147 23.322 25.255 Pnnm IRMOF-IO Zn(N〇3)2 · 4H20 0.02 mmol BPDC 0.012 mmol DEF 90 90 90 34.281 34.281 34.281 Fm-3m ERMOF-11 Zn(N〇3)2 · 4H20 0.05 mmol HPDC 0.20 mmol DEF 90 90 90 24.822 24.822 56.734 R-3m [RMOF-12 Zn(N〇3)2 · 4H20 0.017 mmol HPDC 0.12 mmol DEF 90 90 90 34.281 34.281 34.281 Fm-3m ERMOF-13 DEF 90 90 90 24.822 24.822 56.734 R-3m
Zn(N〇3)2 · 4H20 0.048 mmol PDC 0.31 mmol 158295.doc -24- 201223962 ADC 乙炔二羧酸 NDC 萘二羧酸 BDC 苯二羧酸 ATC 金剛烷四羧酸 BTC 苯三羧酸 BTB 苯三苯甲酸 MTB 甲烷四苯曱酸 ATB 金剛烷四苯甲酸 ADB 金剛烷二苯甲酸 IRMOF-14 Zn(N〇3)2 . 4H20 0.17 mmol PDC 0.12 mmol DEF 90 90 90 34.381 34.381 34381 Fm-3m DRMOF-15 Zn(N03)2 . 4H20 0.063 mmol TPDC 0.025 mmol DEF 90 90 90 21.459 21.459 21.459 Im-3m [RMOF-16 Zn(N〇3)2 · 4H20 0.0126 mmol TPDC 0.05 mmol DEF NMP 90 90 90 21.49 21.49 21.49 Pm-3m 其他金屬有機架構係MOF-69至80、MOF103至106、 MOF-177、MOF-235、MOF-236、MOF-501、MOF-502、 MOF-505、IRMOF-1、IRMOF-61、IRMOP-51、MIL-45、 MIL-47、MIL-53、MIL-59、MIL-60、MIL-61、MIL63、 MIL-68、MIL-85,其等係描述於文獻資料中。 特佳的金屬有機架構係MIL-53、Zn-第三丁基-間苯二 酸 ' A1-BDC ' MOF-5 ' MOF-177、MOF-505、IRMOF-8、 IRMOF-11、Cu-BTC、A1-NDC、A1-BTC、Cu-BTC、A1- 158295.doc -25- 201223962 NDC、Mg-NDC、鋁-富馬酸鹽、MOF-74、Sc-對苯二曱酸 鹽。甚至更佳係AhBDC、鋁-富馬酸鹽、Al-NDC、Al-BTC及 Cu-BTC。 該不含氮之至少一種至少雙牙有機化合物較佳係衍生自 二羧酸、三羧酸或四羧酸。 就本發明之目的而言,術語「衍生」意指就羧基官能基 而言,該至少一種至少雙牙有機化合物係以部份或完全去 質子化形式存在。此外,術語「衍生」意指該至少一種至 少雙牙有機化合物可具有其他取代基。因此,除該羧酸官 能基以外,可存在一或多個(彼此獨立)如羥基、甲氧基、 鹵素或曱基之取代基。較佳係無其他取代基,或僅存在F 取代基。就本發明之目的而言,術語「衍生」亦意指該羧 酸官能基可以硫類似物形式存在。硫類似物係-C(=0)SH, 及其互變異構體及-C(S)SH。以不存在硫類似物較佳。 除如(例如)US 5,648,508中所述之製備MOF之習知方法 以外,其亦可藉由電化學途徑製備。就此而言,可參考 DE-A 103 55 087及 WO-A 2005/049892。 在步驟(b)中,進行一或多種金屬組分之至少部份移 除。較佳地,此或此等金屬組分包括至少一種金屬氧化 物。 較佳藉由以驗性液體洗出,進行該至少部份移除。亦可 使用先前技術中已知之其他方法。適宜的鹼性液體係(例 如)NaOH水溶液。其他鹼金屬氫氧化物亦適宜。亦可根據 該金屬化合物進行酸處理。 158295.doc -26- 201223962 在步驟(C)中,進行自步驟(a)或(b)中獲得之複合物之浸 潰。化學品浸潰係已知且可如浸潰多孔金屬有機架構般進 行。此係描述於(例如)國際專利申請案PCT/EP2010/ 053530中。 較佳藉由混合及隨後加熱來實現浸潰。較佳藉由機械混 合,進行該浸潰。可以固體形式,或自懸浮液或溶液,特 定言之有機溶液(如含曱苯溶液(特定言之係甲苯溶液)), 引入硫。 本發明另外提供一種可藉由根據本發明之方法獲得之複 合物。 本發明另外提供一種可藉由本發明方法獲得之根據本發 明之複合物材料之用途,其係用於吸收至少一種物質以用 於該物質之儲存、移除、受控制釋放、化學反應或作為支 持物。 該至少一種物質較佳係氣體或氣體混合物。 使用金屬有機架構之儲存方法一般係描述於WO-A 2005/003622、WO-A 2003/064030、WO-A 2005/049484、 WO-A 2006/089908 及 DE-A 10 2005 012 087 中。彼等所述 之方法亦可用於本發明複合物。 使用金屬有機架構之分離或純化方法一般係描述於EP-A 1 674 555、DE-A 10 2005 000938及 DE-A 10 2005 022 844 中。彼等所述之方法亦可用於本發明複合物。 如果本發明複合物係用於儲存,此較佳係在-200 °C至 + 80°C之溫度範圍内進行。以-40°C至+80°C之溫度範圍更 s 158295.doc -27- 201223962 佳。 就本發明之目的而言,將簡潔使用術語「氣體」及「液 體」,但氣體混合物及液體混合物或液體溶液亦涵蓋於術 s吾「氣體」或「液體J中·。 較佳的氣體係氫氣、天然氣、民用煤氣、烴(特定言之 係曱烷、乙烷、乙炔、電石氣、丙烷、正丁烷及異丁 烷)、一氧化碳、二氧化碳、氮氧化物、氧氣、硫氧化 物、齒素、鹵化烴、NF3、SF6、氨、硼烷、磷烷、硫化 氫、胺 '甲醛、惰性氣體(特定言之係氦氣、氖氣、氬 氣、氪氣及氙氣)。 該氣體特佳係二氧化碳,其係自包含二氧化碳之氣體混 合物中分離出。該氣體混合物較佳包括二氧化碳、及至少 H2、CH4或一氧化碳。特定言之,該氣體混合物除二氧化 碳以外亦包括一氧化碳。以包含至少丨〇體積%但不多於45 體積%之二氧化碳及至少3 0體積%但不多於9〇體積%之一 氧化碳之混合物極佳。 一較佳實施例係使用複數個平行吸附器反應器之變壓式 吸附,其中該吸附劑裝料係全部或部份由根據本發明之材 料組成。用於C〇2/CO分離之吸附階段較佳係在0.6至3 bar 之C〇2分壓及至少20°C但不大於7(TC之溫度下發生。爲了 解吸所吸附之二氧化碳,通常將所關注之吸附器反應器中 之總壓力降低至100 mbar至1 bar範圍内之值。 亦以使用本發明架構在100 bar(絕對值)之最小壓力下儲 存氣體較佳。該最小壓力更佳係200 bar(絕對值),特定言 158295.doc • 28 - c; 201223962 之係300 bar(絕對值)。該氣體特佳係氩氣或曱烷。 然而’該至少一種物質亦可係液體。此等液體之實例係 消毒劑、無機或有機溶劑、燃料(特定言之係汽油或柴 油)、液壓流體、散熱流體、制動液或油(特定言之係機 油)。此外,該液體可係齒化脂族或芳族、環狀或無環烴 或其混合物。特定言之,該液體可係丙酮、乙腈、苯胺、 苯曱醚 '苯、苯甲腈、溴苯、丁醇、第三丁醇、喹啉、氯 笨、氯仿、環己院、二乙二醇、乙趟、二甲基乙醯胺、二 甲基甲醯胺、二甲基亞砜、二噁烷、冰乙酸、乙酸酐、乙 酸乙酯、乙醇、碳酸乙二酯、二氯乙烯、乙二醇、乙二醇 二甲醚、甲醯胺、己烷、異丙醇、甲醇、甲氧基丙醇、3_ 甲基-1-丁醇、二氯甲烷、甲基乙基酮、N_曱基甲醯胺、 N-甲基吡咯啶酮、硝基苯、硝基曱烷、哌啶、丙醇、碳酸 丙二酯、吡啶、二硫化碳、環丁砜、四氯乙烯、四氣化 碳、四氫呋喃、甲苯、三氯乙烷、三氯乙烯、三乙 胺、二乙二醇、三乙二醇二甲醚、水或其混合物。 此外’該至少一種材料可係氣味物質。 s亥氣味物質較佳係揮發性有機或無機化合物(其包括 氮、磷、氧、硫、氟、氯、溴或碘元素中之至少一者), 或係不飽和芳族烴或飽和或不飽和醛或酮。更佳的元素係 氮、氧、磷、硫、氣、漠;以氮、氧、構及硫特佳。 特定S之’該氣味物質係氨、硫化氫、硫氧化物、氮氧 化物、臭氧、環狀或無環胺、硫醇、硫醚及醛'酮、酯、 醚、酸或醇。以氨、硫化氫、有機酸(較佳係醋酸、丙
S 158295.doc -29- 201223962 酸、丁酸、異丁酸、戊酸、異戊酸、己酸、庚酸、月桂 酸、壬酸)及包含氮或硫之環狀或無環烴及飽和或不飽和 醛(如己醛、庚醛、辛醛、壬醛、癸醛、辛烯醛或壬婦醛) 且特定言之揮發性酸(如丁酸、丙醛、己酸及曱醛)及其他 燃料(如汽油、柴油(組分))特別佳。 該氣味物質亦可係用於(例如)製傭香水之香料。關於香 料或釋放此等香料之油,舉例而言可述及:香精油、羅勒 油、天竺葵油、薄荷油、依蘭樹油、菫蔻油、薰衣草油、 薄荷油、肉豆蔻油、甘菊油、桉樹油、迷迭香油、檸檬 油、酸橙油、橙油、香檸檬油、麝香鼠尾草油、聶荽油、 柏樹油、1,1-二曱氧基-2-苯乙烷、2,4_二曱基_4_笨基四氫 呋喃、二曱基四氫苯曱醛、2,6_二曱基_7_辛烯_2_醇、丨,2_ 二乙氧基-3,7-二甲基-2,6-辛二烯、笨乙醛、玫瑰醚、2_甲 基戊酸乙酯、1-(2,6,6-三曱基-^―環己二烯_丨_基)_2_ 丁烯_ 1-酮、乙基香蘭素、2,6-二甲基_2_辛烯醇、3,7_二曱基_2_ 辛烯醇、乙酸第三丁基環己_、乙酸茵香、乙酸烯丙基 環己氧基酯、乙基沈香醇'丁子香酚、香豆素、乙醯乙酸 乙醋、4-苯基-2,4,6-三f基-以二㈣、4_亞甲基_3,5,M_ 四甲基-2-庚_、四氫藏紅花酸乙黯、香葉腈、順式冬己 烯-1-醇 '順式-3-己婦基乙酸醋1式_3_己婦基甲基碳酸 醋、2’6-二曱基-5-庚稀小酸、心(三環[5 2」〇]癸亞基卜8_ 丁齡、5_(2,2,3_三甲基·3_環戊烯基)·%曱基戊·2·醇、對第 三丁基α-甲基氫肉㈣、[山別三環癸烧甲酸乙醋、香 葉醇、香茅醇、檸檬醛、芳樟醇、乙酸芳樟醋、紫羅酮、 158295.doc •30· 201223962 苯乙醇或其混合物。 就本發明之目的而言,揮發性氣味物質較佳具有低於 300°C之沸點或沸點範圍。該氣味物質更佳係易揮發性化 合物或混合物。該氣味物質特佳具有低於250°C,更佳低 於230°C,特佳低於200°C之沸點或沸點範圍。 同樣以具有高揮發性之氣味物質較佳。蒸氣壓可用作揮 發性之衡量值。就本發明之目的而言,揮發性氣味物質較 佳具有大於0.001 kPa(20°C)之蒸氣壓。該氣味物質更佳係 易揮發性化合物或混合物。該氣味物質特佳具有大於〇 . 〇 1 kPa(2〇C)之蒸氣壓,更佳大於〇.〇5 kPa(20°C)之蒸氣壓。 該氣味物質特佳具有大於0.1 kPa(20°C)之蒸氣;t。 其中可在本發明金屬有機架構之存在下發生化學反應的 實例係單元醇及多元醇之烷氧基化作用。進行此等烧氧基 化之方法係描述於W〇-A 03/035717及w〇_A 2〇〇5/〇3〇69 中。同樣地’本發明多孔金屬有機架構可用於聚伸烷基碳 酸酯及過氧化氫之環氧化及製備。此等反應係描述於禪化 A 03/101975、WO-A 2004/037895及 US-A 2004/081611 中。 以催化反應特佳。 此外,本發明金屬有機架構可用作支持物,特定言之係 用作觸媒支持物。 本發明之硫浸潰複合物尤其適宜作為硫電極。 因此’本U另外提供—種包含根據本發明之該複合物 之硫電極。 本發明另外提供-種根據本發明之硫電極於仏硫電池 s J58295.doc •31 - 201223962 中之用途,且亦提供一種包含此硫電極之[卜硫電池。 【實施方式】 實例 實例1 : Α1-對苯二〒酸m〇f之熱解 實驗方法: 將20 g之Al-M〇F(Al-對苯二甲酸M〇F :由朗繆爾 (Langmuir)法測得係1100 mVg)引入熔融矽石管中。將此置 於管式爐中並用氮氣沖诜過夜。隨後,將該管於氮氣流中 歷時2小時加熱至60(rc。在此步驟期間,緩慢旋轉該管 (45 rPm)。使該粉末在6〇(rc下熱解!小時。冷卻之後(約 1.5小時)’將黑色粉末自該管移除。 所獲重量:8.7 g 分析: 表面積:由朗繆爾法測得係387 m2/g 元素分析:3 0重量% A1 實例2 :經熱解之鋁-對苯二甲酸鹽2Na〇H清洗 起始材料:6·47 g實例1之熱解材料 10〇 g氫氧化鈉溶液,濃度係1 〇〇/〇 實驗步驟 a) 合成:於25〇 mi四頸燒瓶中,在8〇cc下,用氫氧化鈉 溶液擾拌實例1之熱解材料10小時。 b) 處理:在室溫下,在4號玻璃料上過濾出固體,以每 次5〇 ml去離子水攪拌3次,靜置5分鐘,過濾;以每次% ml去離子水清洗7次。最後,用25加丨丙酮攪拌,並吸乾。 158295.doc -32- 201223962 C)乾燥:在真空乾燥烘箱中於100t下持續16小時。 顏色:黑色 產量:2.61 g 分析: 體積密度:186 g/1 表面積:由朗繆爾法測得係1620 m2/g 元素分析:0.1重量% A1 ; 〇.61重量% Na 實例3:用硫填充實例1之材料 將1·〇 g實例1之材料及6 g硫均勻混合,並在開玫式骏 中於18(TC下加熱6小時。此獲得5.3 §固體深灰色物質3 藉由球磨法將其研磨成微細粉末。 元素分析: C=6.6重量% S=83重量% 實例4:用硫填充實例2之材料 將1.0 g實例2之材料及6 g硫均勻混合,並在開放式裝置 中於180°C下加熱6小時。此獲得5 7 g多孔深灰色物質,且 猎由球磨法將其研磨成微細粉末。 元素分析: C=12.5 重量 % 呂=86重量% 實例5 :根據本發明之電化學電池之製法(電極)
將 2.3 0 g實例 3 或 4之材料、〇 8〇 ^Super p、〇 ii 0KS 6、0·15 g之Celvol黏合劑混合在一@。將該混合物分散於 65%H2〇、30%異丙醇、5%丨_甲氧基·2_丙醇之溶劑混合物
S 158295.doc 201223962 中。攪拌該分散液ι〇小時。 藉由刮刀將該分散液塗覆於A1箔上,並在減壓及40°c下 乾燥10小時。 實例6:基準電化學電池之製法 將 3.310 g硫、2.39 g之 Super P、0.19 g之KS 6、0.25 g之 Celvol黏合劑混合在一起。將該混合物分散於65% H2〇、 3 0%異丙醇、5% 1-曱氧基-2-丙醇之溶劑混合物中。攪拌 該分散液10小時。 實例7 :本發明電化學電池之測試 爲進行該複合物之電化學特徵分析,製造電化學電池。 陽極·· 50 μιη厚Li箔,1 5 μπι厚分離器Tonen,含有上述複 合材料之陰極。電解質:8重量%之LiTFSI(LiN (S02CF3)2)、4重量°/〇之LiN03、44重量%之二氧戊環及44重 量%之二曱氧基乙烷。 在1.8至2.5之電位範圍内,於7.50 mA電流下,進行該電 池之充電及放電。該電池容量係75.1 mAh。結果係匯總於 表1中。 表1 樣品 容量 第5次循環[mAh/g S] 容量 第50次循環[mAh/g S] 實例6 850 800 實例5(來自實例3 之材料) 1120 950 實例5(來自實例4 之材料) 1130 950 158295.doc -34-
Claims (1)
- 201223962 七、申請專利範圍: 1' 種製備含碳複合物之方法,其包括以下步驟: (a)在保護性氣體氣氛下,使包含與至少一種金屬離子 配位之至少一種至少雙牙有機化合物之多孔金屬有機架 構熱解’其中該至少—種至少雙牙有機化合物不含氮。 2.如咕求項1之方法,其中在至少500°C下進行該熱解。 3·=明求項之方法中該保護性氣體氣氛包括氮 氣。 $疋万法,其中該至少一種金屬離 子係選自由Mg、A卜Zr、τ. v 屬離 Τι、V、Cr、Mo、Fe、Co、 Cu、Ni及211組成之金屬群之離子。 5.如請求項1至4中任一 之方法,其中該不含氮之至少一 種至少雙牙有機化合物 酸。 生自一缓酸、三缓酸或四缓 請求項1至5中任一項 ______之方法,其包括另一步驟: 〇 如 ru, > ,穴仍刀一艾鄉: (b)自於步驟(a)中所 多種金屬組分。 …复合物至少部份移除一或 如請求項ό之方法,中 -種金屬氧化物。、一或多種金屬組分包括至少 8. 如請求項6或7之方法,其 進行該至少部份移除β 9由以驗性或酸性液體洗出 9·如請求項丨至8中任—項之 ⑷用硫浸潰自步驟(a) :,其包括另-步驟: 10·如請求項9之方法,其中中所獲得之複合物。 、藉由混合及隨後加熱進行該浸 158295.doc 201223962 潰。 如請求項9或10之方法,其尹 使用》 該硫係以固體或溶液形式 12.獲一得種複合物’其可藉由如請求項1至11中任 項之方法 13. —種可藉由 物之h b請求項1至U中任一項之方法獲得之複合 途,其係用於吸附至少一種物質以用於該至少一 =質之儲存、移除、受控制釋放、化學反應或作為支 14. 一種硫電極,直白人叮%丄 其包含可藉由如請求項9至u中任 方法獲得之複合物。 15. -種如請求項14之硫電極於Li_硫電池中之用途。 項之 158295.doc 201223962 四、指定代表圖: (一) 本案指定代表圖為:(無) (二) 本代表圖之元件符號簡單說明: 五、本案若有化學式時,請揭示最能顯示發明特徵的化學式: (無) 158295.doc
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CN103456929B (zh) * | 2013-09-04 | 2015-08-12 | 中南大学 | 一种锂硫电池正极材料及其制备方法 |
CN103500819B (zh) * | 2013-09-18 | 2015-11-18 | 中南大学 | 一种表面修饰多孔状碳结构的碳纤维/硫复合正极材料及其制备方法 |
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DE102015215088A1 (de) | 2015-08-07 | 2017-02-09 | Robert Bosch Gmbh | MOF-Silicium-Kohlenstoff-Komposit-Anodenmaterial |
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US10138199B2 (en) | 2016-03-17 | 2018-11-27 | Saudi Arabian Oil Company | High aspect ratio layered double hydroxide materials and methods for preparation thereof |
CN105932230B (zh) * | 2016-04-27 | 2018-10-26 | 长沙矿冶研究院有限责任公司 | 一种纳米棒多孔碳-硫复合正极材料及其制备方法、锂硫电池 |
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US10875092B2 (en) | 2017-05-19 | 2020-12-29 | Saudi Arabian Oil Company | Methods for preparing mixed-metal oxide diamondoid nanocomposites and catalytic systems including the nanocomposites |
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