CN101534947A - 用做多孔金属有机骨架材料的丁基间苯二甲酸镁 - Google Patents
用做多孔金属有机骨架材料的丁基间苯二甲酸镁 Download PDFInfo
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- CN101534947A CN101534947A CNA2007800411685A CN200780041168A CN101534947A CN 101534947 A CN101534947 A CN 101534947A CN A2007800411685 A CNA2007800411685 A CN A2007800411685A CN 200780041168 A CN200780041168 A CN 200780041168A CN 101534947 A CN101534947 A CN 101534947A
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- Prior art keywords
- metal
- gas
- magnesium
- organic framework
- organic
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- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 65
- 239000000463 material Substances 0.000 title claims description 76
- CNHOBDDGTQEBAQ-UHFFFAOYSA-L [Mg+2].CCCCOC(=O)C1=CC=CC(C([O-])=O)=C1.CCCCOC(=O)C1=CC=CC(C([O-])=O)=C1 Chemical compound [Mg+2].CCCCOC(=O)C1=CC=CC(C([O-])=O)=C1.CCCCOC(=O)C1=CC=CC(C([O-])=O)=C1 CNHOBDDGTQEBAQ-UHFFFAOYSA-L 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 32
- -1 Mg2+ ions Chemical class 0.000 claims abstract description 15
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 150000002500 ions Chemical class 0.000 claims abstract description 4
- 238000013270 controlled release Methods 0.000 claims abstract description 3
- 238000003860 storage Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000011777 magnesium Substances 0.000 claims description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 150000002681 magnesium compounds Chemical class 0.000 claims description 9
- 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 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 159000000003 magnesium salts Chemical class 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 28
- 239000000126 substance Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229910001425 magnesium ion Inorganic materials 0.000 abstract description 2
- 230000007775 late Effects 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 150000002894 organic compounds Chemical class 0.000 description 13
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 229910052749 magnesium Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- MFUVDXOKPBAHMC-UHFFFAOYSA-N magnesium;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MFUVDXOKPBAHMC-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
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- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical class CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 2
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- 150000003997 cyclic ketones Chemical class 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
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- 239000002283 diesel fuel Substances 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
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- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
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- 150000004820 halides Chemical class 0.000 description 2
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- 150000002367 halogens Chemical class 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
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- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000765 intermetallic Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
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- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
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- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 239000001296 salvia officinalis l. Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- YUVKTUCPWGPBLJ-UHFFFAOYSA-N tert-butyl 2-cyclohexylacetate Chemical compound CC(C)(C)OC(=O)CC1CCCCC1 YUVKTUCPWGPBLJ-UHFFFAOYSA-N 0.000 description 1
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- 238000005979 thermal decomposition reaction Methods 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
本发明涉及一种多孔金属有机骨架材料,其是通过Mg2+离子与5-叔丁基间苯二甲酸根离子配位产生骨架结构而形成的。本发明还涉及所述骨架材料的制备方法和用途,例如用于物质例如气体或气体混合物的储存、分离或受控释放。
Description
本发明涉及一种多孔金属有机骨架材料、其制备方法和用途。
多孔金属有机骨架材料在现有技术中是公知的。它们的特征特别在于它们的孔隙率,并可以用于与无机沸石相当的应用中。
金属有机骨架材料一般含有与金属离子配位的至少双齿有机化合物,这种有机化合物与金属离子一起形成金属有机骨架材料的骨架。
金属和/或有机化合物的合适选择使得有可能为所需的应用领域而优化金属有机骨架材料。例如,有机化合物的选择会对孔分布有影响。另外,金属可以在吸附工艺中做出贡献。
因此,仍然需要提供特定的金属有机骨架材料,其由于金属和有机化合物的选择而具有特殊的性能。
作为令人感兴趣的金属,可以提到镁,这是因为由于强配位键,可以从相对窄孔的骨架开始,并且由于镁是在生理学和生态学上都相对没有问题的金属。
M.Dinca等在J.Am.Chem.Soc.127(2005),9376-9377页中描述了2,6-萘二羧酸镁作为具有配位结构的微孔固体。这种骨架材料显示与相应的基于锌的金属有机骨架材料相似的结构。在材料的检测中,作者发现此材料具有高的氢吸附焓并显示与氮或一氧化碳相比而言对氢或氧的选择性吸附。
WO-A 2005/049892描述了在马来酸二乙酯存在下电化学制备作为多孔金属有机骨架材料的对苯二甲酸镁的方法。以此方式获得的骨架材料也在其结构方面与相应的基于锌的金属有机骨架材料相当。
尽管使用现有技术已知的基于镁的金属有机骨架材料获得了有利的结果,但是仍然需要能通过合适选择金属和有机化合物实现的其它骨架结构。
所以,本发明的目的是提供这种基于镁的金属有机骨架材料。
此目的通过一种多孔金属有机骨架材料实现,所述骨架材料是通过Mg2+离子与5-叔丁基间苯二甲酸根离子配位产生骨架结构而形成的。
惊奇地发现,与类似的间苯二甲酸镁相比,本发明的骨架材料具有出人意料的高比表面积,并且特别适用于可含有气态水的气体的分离。
本发明的骨架材料是通过Mg2+离子与5-叔丁基间苯二甲酸(5-叔丁基-1,3-苯二羧酸)或其阴离子形式形成的。
本发明的金属有机骨架材料可以是粉末形式或作为聚集体存在。
本发明的多孔金属有机骨架材料可以原样以粉末形式使用,或者被转化成成型体。因此,本发明的另一个方面是本发明多孔金属有机骨架材料作为成型体的一部分存在。
从金属有机骨架材料生产成型体的方法例如描述在WO-A 03/102000中。
生产成型体的优选方法是挤出或压片。在成型体的生产中,本发明的骨架材料可以含有其它材料,例如粘合剂、润滑剂或在生产期间加入的其它添加剂。也能理解的是,本发明的骨架材料含有其它组分,例如吸收剂,如活性碳等。
对这些成型体的可能的几何形状基本上没有任何限制。可以提到的例子特别是粒料(例如盘形粒料)、小丸、珠、颗粒、挤出物(例如棒状挤出物)、蜂窝结构、网格和中空体。
为了生产这些成型体,原则上可以使用所有合适的方法。特别是,优选以下工艺:
-将骨架材料单独或与至少一种粘合剂和/或至少一种糊化剂和/或至少一种模板化合物一起进行捏合/盘磨得到混合物;通过至少一种合适的方法使所得混合物成型,例如挤出;任选洗涤和/或干燥和/或煅烧挤出物;任选进行最后处理。
-与至少一种粘合剂和/或其它助剂一起压片。
-将骨架材料施用到至少一种任选的多孔载体材料上。所得的材料可以然后进一步按照上述方法加工,得到成型体。
-将骨架材料施用到至少一种任选的多孔基材上。
例如,捏合/盘磨和/或成型可以通过以下方式进行:活塞压制,在存在或不存在至少一种粘合剂的情况下进行的辊压,混合,造粒,压片,挤出,共挤出,发泡,纺丝,涂覆,粒化,优选喷雾粒化,喷雾,喷雾干燥,或两种或多种这些方法的组合。
非常特别优选生产粒料和/或片料。
捏合和/或成型可以在高温下进行,例如在室温到300℃的范围内,和/或在升高的压力下进行,例如在大气压到数百巴的范围内,和/或在保护气体气氛中进行,例如在至少一种稀有气体、氮气或两种或多种所述气体的混合物存在下进行。
捏合和/或成型可以根据另一个实施方案在添加至少一种粘合剂的情况下进行,所用的粘合剂原则上是任何能确保捏合和/或成型组合物所需的粘度的那些化合物。因此,在本发明中,粘合剂可以是能增加粘度的化合物,或是能降低粘度的化合物。
优选的粘合剂特别是例如氧化铝或含氧化铝的粘合剂,例如描述在WO94/29408中;二氧化硅,例如描述在EP 0 592 050A1中,二氧化硅和氧化铝的混合物,例如描述在WO 94/13584中;粘土矿物,例如描述在JP03-037156A中,例如蒙脱土、高岭土、膨润土、埃洛石、地开石、珍珠陶土和蠕陶土;烷氧基硅烷,例如描述在EP 0 102 544B1中,例如四烷氧基硅烷,例如四甲氧基硅烷、四乙氧基硅烷、四丙氧基硅烷、四丁氧基硅烷;或例如三烷氧基硅烷,例如三甲氧基硅烷、三乙氧基硅烷、三丙氧基硅烷、三丁氧基硅烷;烷氧基钛酸酯,例如四烷氧基钛酸酯,例如四甲氧基钛酸酯、四乙氧基钛酸酯、四丙氧基钛酸酯、四丁氧基钛酸酯;和例如三烷氧基钛酸酯,例如三甲氧基钛酸酯、三乙氧基钛酸酯、三丙氧基钛酸酯、三丁氧基钛酸酯;烷氧基锆酸酯,例如四烷氧基锆酸酯,例如四甲氧基锆酸酯、四乙氧基锆酸酯、四丙氧基锆酸酯、四丁氧基锆酸酯,和例如三烷氧基锆酸酯,例如三甲氧基锆酸酯、三乙氧基锆酸酯、三丙氧基锆酸酯、三丁氧基锆酸酯;二氧化硅溶胶,两亲性物质和/或石墨。
除了上述化合物之外,作为提高粘度的物质,可以任选地使用有机化合物和/或亲水性聚合物,例如纤维素;或纤维素衍生物,例如甲基纤维素;和/或聚丙烯酸酯和/或聚甲基丙烯酸酯和/或聚乙烯醇和/或聚乙烯基吡咯烷酮和/或聚异丁烯和/或聚四氢呋喃和/或聚氧化乙烯。
作为糊化剂,优选特别使用水或至少一种醇,例如具有1-4个碳原子的一元醇,例如甲醇、乙醇、正丙醇、异丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇或2-甲基-2-丙醇,或水与至少一种所述醇的混合物;或多元醇,例如二醇,优选水混溶性多元醇,它们单独使用,或作为与水和/或至少一种所述一元醇的混合物使用。
其它可以用于捏合和/或成型的添加剂特别是胺或胺衍生物,例如四烷基铵化合物或氨基醇和含有碳酸根的化合物,例如碳酸钙。这些其它添加剂例如描述在EP 0 389 041 A1、EP 0 200 260 A1或WO 95/19222中。
添加剂例如模板化合物、粘合剂、糊化剂、提高粘度的物质在成型和捏合期间的添加次序在原则上不是关键的。
在另一个优选实施方案中,从捏合和/或成型获得的成型体进行至少一个干燥操作,干燥操作通常在25-500℃的温度进行,优选50-500℃,特别优选100-500℃。也可以进行减压干燥或在保护气体气氛中干燥,或通过喷雾干燥进行。
在一个特别优选的实施方案中,在干燥操作期间,至少部分地从成型体除去至少一种作为添加剂的化合物。
本发明的金属有机骨架材料含有孔,特别是微孔和/或中孔。微孔定义为直径等于或小于2nm的那些孔,中孔定义为直径在2-50nm范围内的孔。微孔和/或中孔的存在可以通过吸附方法检测,这些检测根据DIN 66131和/或DIN 66134确定金属有机骨架材料在77K下吸收氮气的吸附容量。
对于粉末形式的MOF(金属有机骨架材料),按照朗缪尔模型(DIN66131,66134)计算的比表面积是优选大于5m2/g,更优选大于10m2/g,更优选大于50m2/g,甚至更优选大于100m2/g,再更优选大于200m2/g,特别优选大于300m2/g。
含有金属有机骨架材料的成型体可以具有较低的比表面积,但优选是大于10m2/g,更优选大于50m2/g,再更优选大于100m2/g,特别是大于200m2/g。
本发明金属有机骨架材料的孔径尺寸优选是0.2-30nm,特别优选0.3-3nm,基于结晶材料计。
但是,尺寸分布能变化的较大孔也可以在本发明金属有机骨架材料的成型体中出现。但是,优选总孔体积的大于50%、特别是大于75%是由孔直径至多为1000nm的孔形成的。但是,孔体积的主要部分优选是由两个直径范围的孔形成的。所以,进一步优选的是,总孔体积的大于25%、特别是大于50%是由在100-800nm的直径范围内的孔形成的,且总孔体积的大于15%、特别是大于25%是由在至多10nm的直径范围内的孔形成的。孔分布可以通过汞孔隙法检测。
本发明进一步提供一种制备本发明多孔金属有机骨架材料的方法,包括以下步骤:
-使镁化合物和5-叔丁基间苯二甲酸或其盐反应。5-叔丁基间苯二甲酸用做本发明多孔金属有机骨架材料的有机组分,并且能与镁化合物反应。也可以使用5-叔丁基间苯二甲酸的衍生物。因此,例如可以考虑5-叔丁基间苯二甲酸以其盐的形式使用。其中5-叔丁基间苯二甲酸作为完全或部分脱质子化的阴离子存在的盐可以具有任何合适的阳离子。这些阳离子可以是例如单价或二价的金属离子。例子特别是钠盐和钾盐。也可以使用铵化合物的阳离子。在这里,可以特别提到铵本身以及烷基铵阳离子。
镁化合物可以通过金属镁的阳极氧化制备。在这种情况下,本发明的多孔金属有机骨架材料是通过电化学途径制备的。多孔金属有机骨架材料的电化学制备方法描述在WO-A 2005/049892中。本发明的多孔金属有机骨架材料也可以通过此途径制备。
在电化学制备本发明多孔金属有机骨架材料的方法中,优选通过至少一种以下措施至少部分地防止镁离子的阴极再沉积:
(i)使用能促进阴极形成氢气的电解质;
(ii)加入至少一种能导致阴极去极化的化合物;
(iii)使用具有合适氢过电压的阴极。
此方法可以在未分隔的电解池中进行。特别有用的电池是间隙池或堆板电池。这些可以按照双极方式连接。合适的反应介质是例如甲醇、乙醇、二甲基甲酰胺、二乙基甲酰胺,或两种或多种这些溶剂的混合物。
此外,一种或多种电解质盐也可以存在于反应介质中。在这里,电解质盐可以具有季铵作为阳离子组分和具有烷氧基硫酸根作为阴离子组分。总固含量应当大于或等于0.5重量%。
在本发明制备多孔金属有机骨架材料的方法中的反应也可以通过常规途径进行。在这里,镁化合物一般是镁盐。
镁盐可以以烷醇盐、丙酮酸盐、卤化物、亚硫酸盐的形式存在,或作为有机或无机含氧酸的盐存在,或作为它们的混合物存在。
烷醇盐是例如甲醇盐、乙醇盐、正丙醇盐、异丙醇盐、正丁醇盐、异丁醇盐、叔丁醇盐或酚盐。
丙酮酸盐是例如乙酰基丙酮酸盐。
卤化物是例如氯化物、溴化物或碘化物。
有机含氧酸是例如甲酸、乙酸、丙酸或其它烷基单羧酸。
无机含氧酸是例如硫酸、亚硫酸、磷酸或硝酸。
在这里,镁作为Mg2+阳离子出现。
其它优选的镁化合物是无机镁盐,例如氯化镁、溴化镁、硫酸氢镁、磷酸二氢镁、磷酸一氢镁、硝酸镁。
镁化合物可以在合适时含有水合的水。
本发明制备多孔金属有机骨架材料的方法中的反应可以在含水介质中进行。在这里,一般可以使用水热条件或溶热条件。为了本发明目的,术语“热”指这样的制备工艺:其中形成本发明多孔金属有机骨架材料的反应是在反应期间关闭的压力容器中进行的,并且向此容器施加高温使得由于所存在溶剂的蒸气压而导致在压力容器内在反应介质中建立压力。
但是,此反应优选不在含水介质中进行,也不在溶热条件下进行。
本发明方法的反应优选在非水性溶剂的存在下进行。
反应优选在不大于2巴的绝对压力下进行。但是,压力优选不超过1230毫巴(绝对)。反应特别优选在大气压下进行。但是,由于装置,压力可以稍微高于或低于大气压。为了本发明目的,术语“大气压”表示包括实际大气压±150毫巴的压力范围。
反应可以在室温进行。但是,此反应优选在高于室温的温度进行。温度优选高于100℃。此外,温度优选不超过180℃,更优选不超过150℃。
上述金属有机骨架材料通常在添加其它碱的情况下在作为溶剂的水中制备。碱特别用于使用作至少双齿有机化合物的多羧酸能溶于水。由于优选使用非水性有机溶剂,所以不是必须使用这种碱。但是,可以选择用于本发明方法的溶剂以使其本身具有碱性反应,但是这对于进行本发明方法而言不是绝对必须的。
也可以使用碱。但是,优选不使用额外的碱。
此外,反应也可以有利地在搅拌下进行,这在规模扩大时也是有利的。
非水性有机溶剂优选是C1-6链烷醇、二甲基亚砜(DMSO)、N,N-二甲基甲酰胺(DMF)、N,N-二乙基甲酰胺(DEF)、乙腈、甲苯、二噁烷、苯、氯苯、甲乙酮(MEK)、吡啶、四氢呋喃(THF)、乙酸乙酯、任选卤代的C1-C200链烷、环丁砜、二醇、N-甲基吡咯烷酮(NMP)、γ-丁内酯,脂环醇例如环己醇,酮例如丙酮或乙酰基丙酮,环状酮例如环己酮,环丁烯砜或它们的混合物。
C1-6链烷醇是具有1-6个碳原子的醇。例子是甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、戊醇、己醇和它们的混合物。
任选卤化的C1-200链烷是具有1-200个碳原子的链烷,且其中一个或多个至所有氢原子可以被卤素代替,优选氯或氟,特别是氯;例子是氯仿、二氯甲烷、四氯甲烷、二氯乙烷、己烷、庚烷、辛烷和它们的混合物。
优选的溶剂是DMF、DEF和NMP。特别优选DMF。
术语“非水性”优选指溶剂的最大水含量是10重量%,更优选5重量%,甚至更优选1重量%,更优选0.1重量%,特别优选0.01重量%,基于溶剂的总重量计。
在反应期间的最大水含量优选是10重量%,更优选5重量%,甚至更优选1重量%。
术语“溶剂”包括纯溶剂和各种溶剂的混合物。
此外,至少一种金属化合物与至少一种至少双齿有机化合物反应的工艺步骤之后优选是煅烧步骤。此时的温度一般高于250℃,优选是300-400℃。
在孔中存在的至少双齿有机化合物可以通过煅烧步骤除去。
除此之外或作为另一种选择,从多孔金属有机骨架材料的孔中除去至少双齿有机化合物(配体)的操作可以通过用非水性溶剂处理所形成的骨架材料进行。在这里,配体在“萃取工艺”中被除去,并可以任选地在骨架材料中被溶剂分子替代。这种温和的方法在配体是高沸点化合物时是特别有效的。
所述处理优选进行至少30分钟,可以通常进行最多2天的时间。这可以在室温或高温进行。优选在高温进行,例如在至少40℃,优选60℃。萃取更优选在所用溶剂的沸点进行(在回流下)。
所述处理可以在简单容器中通过淤浆化并搅拌骨架材料进行。也可以使用萃取装置,例如索格利特装置,特别是工业萃取装置。
可以使用的合适溶剂是上述那些,即,例如C1-6链烷醇、二甲基亚砜(DMSO)、N,N-二甲基甲酰胺(DMF)、N,N-二乙基甲酰胺(DEF)、乙腈、甲苯、二噁烷、苯、氯苯、甲乙酮(MEK)、吡啶、四氢呋喃(THF)、乙酸乙酯、任选卤代的C1-C200链烷、环丁砜、二醇、N-甲基吡咯烷酮(NMP)、γ-丁内酯,脂环醇例如环己醇,酮例如丙酮或乙酰基丙酮,环酮例如环己酮,或它们的混合物。
优选甲醇、乙醇、丙醇、丙酮、MEK和它们的混合物。
非常特别优选的萃取剂是甲醇。
用于萃取的溶剂可以与用于至少一种金属化合物与至少一种至少双齿有机化合物反应中的溶剂相同或不同。在“萃取”的情况下,溶剂不是必须无水的,但是优选是无水的。
本发明进一步提供本发明的多孔金属有机骨架材料用于吸收至少一种物质的用途,用于所述物质的储存、分离、受控释放或化学反应的目的。
所述至少一种物质优选是气体或气体混合物,其中气体或气体混合物优选含有气态水。
以此方式,可以特别在水的存在下分离出气体或气体混合物,且代替气体或气体混合物被分离出的水不会干扰分离。
本发明进一步提供本发明的多孔金属有机骨架材料作为载体或前体材料用于制备相应金属氧化物(MgO)的用途。
金属有机骨架材料用于储存的方法一般描述在WO-A 2005/003622、WO-A 2003/064030、WO-A 2005/049484、WO-A 2006/089908和DE-A 102005 012 087中。所述的这些方法也可以用于本发明的金属有机骨架材料。
金属有机骨架材料用于分离或提纯的方法一般描述在EP-A 1 674555、DE-A 10 2005 000938和DE-A 10 2005 022 844中。所述的这些方法也可以用于本发明的金属有机骨架材料。
如果本发明的多孔金属有机骨架材料用于储存,则优选在-200℃至+80℃的温度进行。更优选温度是-40℃至+80℃。
所述至少一种物质可以是气体或液体。所述物质优选是气体。
为了本发明目的,为了简洁,使用术语“气体”和“液体”,但是这里的术语“气体”或“液体”也分别涵盖气体混合物以及液体混合物或液体溶液。
优选的气体是氢气;天然气;城市煤气;烃,特别是甲烷、乙烷、乙烯、乙炔、丙烷、正丁烷和异丁烷;一氧化碳,二氧化碳,氮氧化物,氧气,硫氧化物,卤素,卤代烃,NF3,SF6,氨,硼烷,磷烷,硫化氢,胺,甲醛;稀有气体,特别是氦、氖、氩、氪和氙。
但是,所述至少一种物质也可以是液体。液体的例子是消毒剂,无机或有机溶剂,燃料,特别是汽油或柴油;水力流体,散热器流体,制动流体或油,特别是机油。另外,液体可以是卤代的脂族或芳族、环状或无环的烃或其混合物。特别是,液体可以是丙酮、乙腈、苯胺、茴香醚、苯、苯甲腈、溴苯、丁醇、叔丁醇、喹啉、氯苯、氯仿、环己烷、二甘醇、***、二甲基乙酰胺、二甲基甲酰胺、二甲基亚砜、二噁烷、冰醋酸、乙酸酐、乙酸乙酯、乙醇、碳酸亚乙酯、二氯乙烷、乙二醇、乙二醇二甲醚、甲酰胺、己烷、异丙醇、甲醇、甲氧基丙醇、3-甲基-1-丁醇、二氯甲烷、甲乙酮、N-甲基甲酰胺、N-甲基吡咯烷酮、硝基苯、硝基甲烷、哌啶、丙醇、碳酸亚丙酯、吡啶、二硫化碳、环丁砜、四氯乙烯、四氯化碳、四氢呋喃、甲苯、1,1,1-三氯乙烷、三氯乙烯、三乙胺、三甘醇、三甘醇二甲醚、水或它们的混合物。
所述至少一种物质也可以是有气味的物质。
优选,有气味的物质是挥发性的有机或无机化合物,它们含有元素氮、磷、氧、硫、氟、氯、溴或碘中的至少一种,或是不饱和或芳族的烃,或饱和或不饱和的醛或酮。更优选的元素是氮、氧、磷、硫、氯、溴;特别优选氮、氧、磷和硫。
特别是,有气味的物质是氨、硫化氢、硫氧化物、氮氧化物、臭氧、环状或无环的胺、硫醇、硫醚,以及醛、酮、酯、醚、酸或醇。特别优选氨、硫化氢、有机酸(优选乙酸、丙酸、丁酸、异丁酸、戊酸、异戊酸、己酸、庚酸、月桂酸、壬酸)以及含有氮或硫的环状或无环的烃;饱和或不饱和的醛,例如己醛、庚醛、辛醛、壬醛、癸醛、辛烯醛或壬烯醛,特别是挥发性醛,例如丁醛、丙醛、乙醛和甲醛;以及燃料例如汽油、柴油(组分)。
有气味的物质也可以是香料,它们用于例如生产香水。香料或能释放这种香料的油的例子是:精油,罗勒油,香叶油,薄荷油,衣兰油,小豆蔻油,鳄梨油,辣椒油,肉豆蔻油,春黄菊油,桉叶油,玫瑰油,柠檬油,白柠檬油,橙油,香柠檬油,香紫苏油,芫荽子油,丝柏精油,1,1-二甲氧基-2-苯基乙烷,2,4-二甲基-4-苯基四氢呋喃,二甲基四氢苯甲醛,2,6-二甲基-7-辛烯-2-醇,1,2-二乙氧基-3,7-二甲基-2,6-辛二烯,苯基乙醛,玫瑰醚,2-甲基戊酸乙酯,1-(2,6,6-三甲基-1,3-环己二烯-1-基)-2-丁烯-1-酮,乙基香草醛,2,6-二甲基-2-辛烯醇,3,7-二甲基-2-辛烯醇,环己基乙酸叔丁酯,乙酸茴香酯,环己基氧基乙酸烯丙酯,乙基里哪醇,丁子香酚,香豆素,乙酰乙酸乙酯,4-苯基-2,4,6-三甲基-1,3-二噁烷,4-亚甲基-3,5,6,6-四甲基-2-庚酮,四氢藏花酸乙酯,香叶基腈,顺-3-己烯-1-醇,乙酸顺-3-己烯基酯,碳酸顺-3-己烯基甲基酯,2,6-二甲基-5-庚烯-1-醛,4-(三环[5.2.1.0]亚癸基)-8-丁醛,5-(2,2,3-三甲基-3-环戊烯基)-3-甲基戊-2-醇,对-叔丁基-α-甲基氢化肉桂醛,[5.2.1.0]三环癸烷羧酸乙酯,香叶醇,橙花醇,柠檬醛,里哪醇,乙酸里哪基酯,紫罗酮,苯基乙醇,和它们的混合物。
为了本发明目的,挥发性的有气味物质优选具有低于300℃的沸点或沸程。更优选,有气味的物质是挥发性化合物或混合物。特别优选,有气味的物质具有低于250℃的沸点或沸程,更优选低于230℃,特别优选低于200℃。
优选具有高挥发性的有气味物质。蒸气压可以用作挥发性的衡量手段。在本发明中,挥发性的有气味物质优选具有大于0.001kPa(20℃)的蒸气压。更优选,有气味的物质是挥发性化合物或混合物。特别优选,有气味的物质具有大于0.01kPa(20℃)的蒸气压,更优选大于0.05kPa(20℃)。特别优选,有气味的物质具有大于0.1kPa(20℃)的蒸气压。
另外,发现有利的是本发明的多孔金属有机骨架材料可以用于制备氧化镁。在这里,将本发明的金属有机骨架材料加热到高于其完全分解温度的温度。
加热可以通过本领域技术人员公知的方法进行。加热一般在适用于此目的的炉中进行,例如马弗炉。当使用炉时,也有利的是使用能在合适气氛的存在下进行加热的装置。为此,可以在炉中或炉上安装用于合适气体或气体混合物的进料管线,使得含有多孔金属有机骨架材料的炉室能用合适的气体或气体混合物吹扫。
将多孔金属有机骨架材料加热到使金属有机骨架材料转化成相应氧化物所必需的温度。所以加热到比金属有机骨架材料的完全分解温度高的温度。
为了本发明的目的,“完全分解温度”是金属有机骨架材料开始被转化成相应金属氧化物时的温度。但是,金属有机骨架材料也可以经由中间体被转化成金属氧化物。例如,可以在形成金属氧化物之前已经形成碳酸盐。在这种情况下,“完全分解温度”是在每种情况下将最后的中间体转化成金属氧化物所必需的温度。
完全分解温度的测定可以通过本领域技术人员公知的方法进行。例如,此温度可以通过热重法检测,其中也能通过伴随的分析确认相应金属氧化物的形成。
从多孔金属有机骨架材料制备相应金属氧化物所必需的完全分解温度通常在250-1000℃的范围内。完全分解温度更优选在350-800℃的范围内。完全分解温度非常优选在450-650℃的范围内。
所以,多孔金属有机骨架材料的加热在含有供氧组分的氧化气氛的存在下进行。以此方式,可以确保存在能将多孔金属有机骨架材料转化成相应金属氧化物的足够的氧。这也可以特别对上述“蛙跳式”中间体做出贡献。这种氧化气氛可以通过合适的供氧性气体或气体混合物获得。作为最简单和最优选的气体混合物,可以提到一般含有足够高比例的分子氧的空气。如果合适的话,所用的空气可以富含其它氧。最后,当然也可以用纯氧作为氧化气氛。另外,也可以使用例如富含分子氧的其它气体或气体混合物。在这里,特别优选惰性气体。因此,在每种情况下富含氧的氦、氩、氮气或它们的混合物可以作为气体混合物用于生产在加热多孔金属有机骨架材料期间的氧化气氛。
本发明的多孔金属有机骨架材料可以暴露于氧化气氛,使得此气氛不会在加热期间变化。因此,在多孔金属有机骨架材料周围的气体或气体混合物不会被替换,使得此气氛的供氧组分浓度在加热期间降低。
另外,可以通过进一步引入至少此组分而使此气氛中的供氧组分浓度在加热期间大约保持恒定。
但是,优选供氧组分的浓度在加热期间增加。这可以例如通过用具有更高比例供氧组分的气体或气体混合物替换所述气氛进行。这可以特别通过在开始加热后将氧引入气氛中直到最终存在纯氧气氛来实现。增加可以逐步或连续地进行。
可以在本发明金属有机骨架材料的存在下进行的化学反应的例子是一元醇和多元醇的烷氧基化反应。进行这种烷氧基化反应的工序描述在WO-A 03/035717和WO-A 2005/03069中。本发明的多孔金属有机骨架材料也可以用于环氧化反应和用于制备聚亚烷基碳酸酯和过氧化氢。这些反应描述在WO-A 03/101975、WO-A 2004/037895和US-A 2004/081611中。
实施例1:
将9.5g的硝酸镁六水合物、2.78g的5-叔丁基间苯二甲酸和283g的二乙基甲酰胺(DEF)的混合物在500ml烧瓶中在氮气气氛中在130℃搅拌24小时。然后将混合物冷却到室温,过滤出沉淀的产物,每次用50ml的丙酮洗涤,共洗涤四次,随后用N2在带有玻璃料的洗涤瓶中吹干2天。
这得到2.60g的干骨架材料。
图1显示了相关的X-射线衍射图(XRD),其中I表示强度(Lin(计数)),2θ表示2θ角。
通过朗缪尔法测得比表面积是326m2/g。在约470℃发生热分解。
对比实施例2:
将11.0g的硝酸镁六水合物、5.00g的1,3-苯二甲酸(间苯二甲酸)和二乙基甲酰胺(DEF)的混合物在具有Teflon内涂层的200ml不锈钢高压釜中在130℃搅拌24小时。然后将混合物冷却到室温,过滤出沉淀的产物,用N,N-二甲基甲酰胺(2 x 30ml)和氯仿(2 x 30ml)洗涤,随后在空气中干燥。
这得到7.80g的干骨架材料。
不能通过朗缪尔法测得比表面积。
实施例3:
图2显示了用实施例1的骨架材料在313K吸附CO2和CO的吸附等温线。上面的曲线代表CO2,下面的曲线代表CO。这些曲线证明能分离CO2/CO。
Claims (10)
1.一种多孔金属有机骨架材料,其是通过Mg2+离子与5-叔丁基间苯二甲酸根离子配位产生骨架结构而形成的。
2.权利要求1的骨架材料,其作为成型体的一部分存在。
3.一种制备如权利要求1或2所述的金属有机骨架材料的方法,包括以下步骤:
-使镁化合物与5-叔丁基间苯二甲酸或其盐反应。
4.权利要求3的方法,其中镁化合物是通过金属镁的阳极氧化制备的。
5.权利要求3的方法,其中镁化合物是镁盐。
6.如权利要求1或2所述的金属有机骨架材料用于吸收至少一种物质以用于其储存、分离、受控释放或化学反应目的的用途。
7.权利要求6的用途,其中所述物质是气体或气体混合物。
8.权利要求7的用途,其中所述气体或气体混合物含有气态水。
9.如权利要求1或2所述的金属有机骨架材料用作载体的用途。
10.如权利要求1或2所述的金属有机骨架材料作为前体材料用于制备氧化镁的用途。
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EP2242557B1 (de) * | 2008-01-24 | 2011-11-23 | Basf Se | Poröse metallorganische gerüstmaterialien als trockenmittel |
CN102105421B (zh) * | 2008-07-21 | 2013-09-25 | 巴斯夫欧洲公司 | 工业分离丙烯的方法 |
JP5491504B2 (ja) * | 2008-07-30 | 2014-05-14 | ビーエーエスエフ ソシエタス・ヨーロピア | リチウム系金属有機フレーム構造物 |
US8425662B2 (en) | 2010-04-02 | 2013-04-23 | Battelle Memorial Institute | Methods for associating or dissociating guest materials with a metal organic framework, systems for associating or dissociating guest materials within a series of metal organic frameworks, and gas separation assemblies |
WO2011127468A2 (en) * | 2010-04-09 | 2011-10-13 | Lehigh University | Organonitridic frameworks with hierarchical pore structures and high gas selectivity |
US9386869B2 (en) | 2012-12-07 | 2016-07-12 | Koninklijke Philps N.V. | Cover device for a drink container |
WO2015066693A1 (en) * | 2013-11-04 | 2015-05-07 | The Regents Of Thd University Of California | Metal-organic frameworks with a high density of highly charged exposed metal cation sites |
CN104667876B (zh) * | 2013-11-29 | 2018-02-13 | 北京思达安新材料科技有限公司 | 系列MOF型多级孔材料IPD‑mesoMOF‑1~8及其制备方法,以及介孔大小的调节方法 |
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US9139600B2 (en) | 2012-09-19 | 2015-09-22 | Basf Se | Acetylene bridged linkers and metal-organic frameworks (MOFs) produced thereof |
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