EP2611766A1 - Process for producing carbon-comprising composite - Google Patents
Process for producing carbon-comprising compositeInfo
- Publication number
- EP2611766A1 EP2611766A1 EP11821197.8A EP11821197A EP2611766A1 EP 2611766 A1 EP2611766 A1 EP 2611766A1 EP 11821197 A EP11821197 A EP 11821197A EP 2611766 A1 EP2611766 A1 EP 2611766A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- process according
- composite
- sulfur
- metal
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000002131 composite material Substances 0.000 title claims abstract description 29
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 32
- 239000012621 metal-organic framework Substances 0.000 claims abstract description 31
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 26
- 239000011593 sulfur Substances 0.000 claims abstract description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 8
- 230000001681 protective effect Effects 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000000197 pyrolysis Methods 0.000 claims description 8
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 8
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 8
- 238000005470 impregnation Methods 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052804 chromium Inorganic materials 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
- 238000005406 washing Methods 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000013270 controlled release Methods 0.000 claims description 2
- 238000010438 heat treatment 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
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- -1 Sr Chemical compound 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000126 substance Substances 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
- 150000001491 aromatic compounds Chemical class 0.000 description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-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
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 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
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 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 6
- 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
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229920002266 Pluriol® Polymers 0.000 description 4
- 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 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000013148 Cu-BTC MOF Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000013206 MIL-53 Substances 0.000 description 3
- 239000013132 MOF-5 Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 150000003463 sulfur Chemical class 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
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 2
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 description 2
- LQWVYIRHSBXGBX-UHFFFAOYSA-N 2-[2,2,3-tris(2-carboxyphenyl)-1-adamantyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1(C(C(C2)(C=3C(=CC=CC=3)C(O)=O)C3)(C=4C(=CC=CC=4)C(O)=O)C=4C(=CC=CC=4)C(O)=O)CC3CC2C1 LQWVYIRHSBXGBX-UHFFFAOYSA-N 0.000 description 2
- PAMBMUOTYPLTQG-UHFFFAOYSA-N 2-[2,3-bis(2-carboxyphenyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC(C=2C(=CC=CC=2)C(O)=O)=C1C1=CC=CC=C1C(O)=O PAMBMUOTYPLTQG-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical class OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 2
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013236 Zn4O(BTB)2 Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- ZWWLLYJRPKYTDF-UHFFFAOYSA-N thiophene-3,4-dicarboxylic acid Chemical compound OC(=O)C1=CSC=C1C(O)=O ZWWLLYJRPKYTDF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
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- 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
- B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
-
- 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
- B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
- B01J20/08—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04 comprising aluminium oxide or hydroxide; comprising bauxite
-
- 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
- B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3234—Inorganic material layers
-
- 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
- B01J6/00—Heat treatments such as Calcining; Fusing ; Pyrolysis
-
- 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
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
- C04B35/52—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite
-
- 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
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/00853—Uses not provided for elsewhere in C04B2111/00 in electrochemical cells or batteries, e.g. fuel cells
-
- 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
- C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
- C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
- C04B2235/30—Constituents and secondary phases not being of a fibrous nature
- C04B2235/44—Metal salt constituents or additives chosen for the nature of the anions, e.g. hydrides or acetylacetonate
- C04B2235/449—Organic acids, e.g. EDTA, citrate, acetate, oxalate
-
- 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
- C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
- C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
- C04B2235/30—Constituents and secondary phases not being of a fibrous nature
- C04B2235/48—Organic compounds becoming part of a ceramic after heat treatment, e.g. carbonising phenol resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Definitions
- the present invention relates to a process for producing a carbon-comprising composite.
- the invention further relates to composites which can be obtained in this way and sulfur electrodes comprising these and also their uses.
- Composites are materials which comprise two or more bonded materials. Their precise chemical composition is frequently unknown, so that they usually have to be characterized by the process for producing them and also the starting materials.
- An example is a composite produced from a porous metal-organic framework made up of cobalt ions and a nitrogen-comprising ligand (1 ,3,5-triazine-2,4,6-triyltrisglycine, TTG).
- This composite is produced by pyrolysis and, owing to its nitrogen content, has good separation properties for the separation of C0 2 /CH 4 (Y. Shen et al., Chem. Commun. 46 (2010), 1308-1310).
- the object is achieved by a process for producing a carbon-comprising composite, which comprises the step (a) Pyrolysis of a porous metal-organic framework comprising at least one at least bidentate organic compound coordinated to at least one metal ion under a protective gas atmosphere, where the at least one at least bidentate organic compound is nitrogen-free.
- the process of the invention can comprise a further step (b).
- a further step (b) an at least partial removal of one or more metal components from the composite obtained in step (a) is carried out.
- This metal component or these metal components result from the transformation of the at least one metal ion comprised in the porous metal-organic framework.
- the process of the invention can comprise a step (c) in which the composite obtained from step (a) or (b) is impregnated with sulfur.
- the pyrolysis can be carried out by processes known in the prior art.
- the pyrolysis in step (a) is preferably carried out at a temperature of at least 500°C, preferably at least 600°C.
- the pyrolysis is more preferably carried out in a temperature range from 600°C to 1000°C, even more preferably in the range from 600°C to 800°C.
- Process step (a) is carried out under a protective gas atmosphere.
- the protective gas atmosphere is preferably an atmosphere of nitrogen.
- Other generally known protective gases such as noble gases are also possible.
- a porous metal-organic framework is used as starting material. This comprises at least one at least bidentate organic compound coordinated to at least one metal ion, where the at least one at least bidentate organic compound is nitrogen-free.
- MOFs metal-organic frameworks
- the metal-organic frameworks according to the present invention comprise pores, in particular micropores and/or mesopores.
- Micropores are defined as pores having a diameter of 2 nm or less and mesopores are defined by a diameter in the range from 2 to 50 nm, in each case, corresponding to the definition given in Pure & Applied Chem. 57 (1983), 603 - 619, in particular on page 606.
- the presence of micropores and/or misopores can be checked by means of sorption measurements which determine the uptake capacity for nitrogen of the MOF at 77 kelvin in accordance with DIN 66131 and/or DIN 66134.
- the specific surface area, calculated according to the Langmuir model (DIN 66131 , 66134) for an MOF in powder form is greater than 100 m 2 /g, more preferably above 300 m 2 /g, more preferably greater than 700 m 2 /g, even more preferably greater than 800 m 2 /g, even more preferably greater than 1000 m 2 /g and particularly preferably greater than 1200 m 2 /g.
- Shaped bodies comprising metal-organic frameworks can have a relatively low active surface area, but this is preferably greater than 150 m 2 /g, more preferably greater than 300 m 2 /g, even more preferably greater than 700 m 2 /g.
- the metal component in the framework according to the present invention is preferably selected from groups la, lla, Ilia, IVa to Villa and lb to Vlb. Particular preference is given to Mg, Ca, Sr, Ba, Sc, Y, Ln, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ro, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Zn, Cd, Hg, Al, Ga, In, TI, Si, Ge, Sn, Pb, As, Sb and Bi, where Ln denotes lanthanides.
- Lanthanides are La, Ce, Pr, Nd, Pm, Sm, En, Gd, Tb, Dy, Ho, Er, Tm, Yb.
- At least bidentate organic compound refers to an organic compound which comprises at least one functional group which is able to form at least two coordinate bonds to a given metal ion and/or to form one coordinate bond to each of two or more, preferably two, metal atoms.
- radical R is not present.
- groups are, inter alia, CH(SH) 2 , -C(SH) 3 , -CH(OH) 2 , or -C(OH) 3 .
- the at least two functional groups can in principle be bound to any suitable organic compound as long as it is ensured that the organic compound bearing these functional groups is capable of forming the coordinate bond and of producing the framework.
- the organic compounds comprising the at least two functional groups are preferably derived from a saturated or unsaturated aliphatic compound or an aromatic compound or a both aliphatic and aromatic compound.
- the aliphatic compound or the aliphatic part of the both aliphatic and aromatic compound can be linear and/or branched and/or cyclic, with a plurality of rings per compound also being possible.
- the aliphatic compound or the aliphatic part of the both aliphatic and aromatic compound more preferably comprises from 1 to 15, more preferably from 1 to 14, more preferably from 1 to 13, more preferably from 1 to 12, more preferably from 1 to 1 1 1 and particularly preferably from 1 to 10, carbon atoms, for example 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Particular preference is given here to, inter alia, methane, adamantine, acetylene, ethylene or butadiene.
- the aromatic compound or the aromatic part of the both aromatic and aliphatic compound can have one or more rings, for example two, three, four or five rings, with the rings being able to be present separately and/or with at least two rings being fused.
- the aromatic compound or the aromatic part of the both aliphatic and aromatic compound particularly preferably has one, two or three rings, with one or two rings being particularly preferred.
- Each ring of the compound mentioned can also independently comprise at least one heteroatom such as O, S, B, P, Si, Al, preferably N, O and/or S.
- the aromatic compound or the aromatic part of the both aromatic and aliphatic compound more preferably comprises one or two C 6 rings, with the rings being present either separately or in a fused form. Particular mention may be made of benzene, naphthalene and/or biphenyl as aromatic compounds.
- the at least bidentate organic compound is more preferably an aliphatic or aromatic, acyclic or cyclic hydrocarbon which has from 1 to 18, preferably from 1 to 10 and in particular 6, carbon atoms and additionally has exclusively 2, 3 or 4 carboxyl groups as functional groups.
- the at least bidentate organic compound is derived from a dicarboxylic acid such as oxalic acid, succinic acid, tartaric acid, 1 ,4-butanedicarboxylic acid, 1 ,4- butenedicarboxylic acid, 4-oxopyran-2,6-dicarboxylic acid, 1 ,6-hexanedicarboxylic acid, decanedicarboxylic acid, 1 ,8-heptadecanedicarboxylic acid, 1 ,9-hepta- decanedicarboxylic acid, heptadecanedicarboxylic acid, acetylenedicarboxylic acid, 1 ,2-benzenedicarboxylic acid, 1 ,3-benzenedicarboxylic acid, 1 ,3-butadiene-1 ,4- dicarboxylic acid, 1 ,4-benzenedicarboxylic acid, p-benzenedicarboxylic acid, thiophen
- the at least bidentate organic compound is even more preferably one of the dicarboxylic acids mentioned by way of example above as such.
- the at least bidentate organic compound can, for example, be derived from a tricarboxylic acid such as
- the at least bidentate organic compound is even more preferably one of the tricarboxylic acids mentioned by way of example above as such.
- Examples of an at least bidentate organic compound derived from a tetracarboxylic acid are 1 ,1 -dioxidoperylo[1 ,12-BCD]thiophene-3,4,9,10-tetracarboxylic acid, perylene- tetracarboxylic acids such as perylene-3,4,9,10-tetracarboxylic acid or (perylene 1 ,12- sulfone)-3,4,9,10-tetracarboxylic acid, butanetetracarboxylic acids such as 1 ,2,3,4- butanetetracarboxylic acid or meso-1 ,2,3,4-butanetetracarboxylic acid, decane-2, 4,6,8- tetracarboxylic acid , 1 ,4,7,10,13,16-hexaoxacyclooctadecane-2,3, 1 1 , 12-tetracarboxylic acid, 1 ,2,4,5-benz
- the at least bidentate organic compound is even more preferably one of the tetracarboxylic acids mentioned by way of example above as such.
- Very particular preference is given to optionally at least monosubstituted aromatic dicarboxylic, tricarboxylic or tetracarboxylic acids having one, two, three, four or more rings with each of the rings being able to comprise at least one heteroatom and two or more rings being able to comprise identical or different heteroatoms.
- Suitable heteroatoms are, for example, O, S, B, P, and preferred heteroatoms among these are S and/or O.
- suitable substituents mention may be made of, inter alia, -OH, a nitro group, an alkyl or alkoxy group.
- acetylenedicarboxylic acid ADC
- camphordicarboxylic acid fumaric acid
- succinic acid benzenedicarboxylic acids
- phthalic acid isophthalic acid, terephthalic acid (BDC)
- naphthalenedicarboxylic acids NDC
- biphenyldicarboxylic acids such as 4,4'-biphenyldicarboxylic acid (BPDC)
- benzenetricarboxylic acids such as 1 ,2,3-, 1 ,2,4-benzenetricarboxylic acid or 1 ,3,5- benzenetricarboxylic acid (BTC), benzenetetracarboxylic acid, adamantanetetracarboxylic acid (ATC), adamantanedibenzoate (ADB), benzenetribenzoate (BTB), methanetetrabenzoate (MTB), adamantanetetrabenzoate or di
- phthalic acid isophthalic acid, terephthalic acid, 2,6-naphthalenedicarboxylic acid, 1 ,4-naphthalenedicarboxylic acid, 1 ,5-naphthalenedicarboxylic acid, 1 ,2,3-benzenetricarboxylic acid, 1 ,2,4- benzenetricarboxylic acid, 1 ,3,5-benzenetricarboxylic acid, 1 ,2,4,5- benzenetetracarboxylic acid, fumaric acid, biphenyldicarboxylate, 1 ,5- and 2,6- naphthalenedicarboxylic acid, tert-butylisophthalic acid, dihydroxybenzoic acid, BTB, HPDC, BPTC.
- the metal-organic framework can also comprise one or more monodentate ligands and/or one or more at least bidentate ligands which are not derived from a dicarboxylic, tricarboxylic or tetracarboxylic acid.
- the metal-organic framework can also comprise one or more monodentate ligands.
- Suitable solvents for preparing the metal-organic framework are, inter alia, ethanol, dimethylformamide, toluene, methanol, chlorobenzene, diethylformamide, dimethyl sulfoxide, water, hydrogen peroxide, methylamine, sodium hydroxide solution, N- methylpyrrolidone ether, acetonitrile, benzyl chloride, triethylamine, ethylene glycol and mixtures thereof.
- Further metal ions, at least bidentate organic compounds and solvents for the preparation of MOF are described, inter alia in US-A 5,648,508 or DE-A 101 1 1 230.
- the pore size of the metal-organic framework can be controlled by selection of the suitable ligand and/or the at least bidentate organic compound. In general, the larger the organic compound, the greater the pore size.
- the pore size is preferably from 0.2 nm to 30 nm, particularly preferably in the range from 0.3 nm to 3 nm, based on the crystalline material.
- metal-organic frameworks examples are given below.
- the metal and the at least bidentate ligand, the solvent and the cell parameters are indicated. The latter were determined by X-ray diffraction.
- metal-organic frameworks are MOF-69 to 80, MOF103 to 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 , MIL-63, MIL-68, MIL-85, which are described in the literature.
- metal-organic frameworks are MIL-53, Zn-tBu-isophthalic acid, AI-BDC, MOF-5, MOF-177, MOF-505, IRMOF-8, IRMOF-1 1 , Cu-BTC, AI-NDC, AI-BTC, Cu-BTC, AI-NDC, Mg-NDC, Al-fumarate, MOF-74, Sc-terephthalate. Even greater preference is given to AI-BDC, Al-fumarate, AI-NDC, AI-BTC and Cu-BTC.
- the nitrogen-free at least one at least bidentate organic compound is preferably derived from a dicarboxylic, tricarboxylic or tetracarboxylic acid.
- the term “derived” means that the at least one at least bidentate organic compound is present in partially or fully deprotonated form, as far as the carboxy functions are concerned.
- the term “derived” means that the at least one at least bidentate organic compound can have further substituents.
- substituents such as hydroxyl, methoxy, halogen or methyl groups can be present in addition to the carboxylic acid function. It is preferred that no further substituent, or only F substituents, is/are present.
- the term "derived" also means that the carboxylic acid function can be present as sulfur analogues.
- step (b) an at least partial removal of one or more metal components is carried out. It is preferred that this or these comprise at least one metal oxide.
- the at least partial removal is preferably carried out by washing out by means of an alkaline liquid.
- an alkaline liquid is, for example, an aqueous NaOH solution.
- alkali metal hydroxides are also suitable.
- an acid treatment is also possible.
- step (c) an impregnation of the composite obtained from step (a) or (b) is carried out. Impregnation with chemicals is known and can be carried out as in the impregnation of porous metal-organic frameworks. This is described, for example, in the international patent application PCT/EP2010/053530.
- the impregnation is preferably effected by mixing and subsequent heating.
- the impregnation is preferably carried out by mechanical mixing.
- Sulfur can be introduced as a solid or from a suspension or solution, in particular an organic solution such as a toluene-comprising solution, in particular a toluene solution.
- the present invention further provides a composite which can be obtained by a process according to the present invention.
- the present invention further provides for the use of a composite material according to the invention which can be obtained by a process according to the invention for absorption of at least one material for the purposes of storage, removal, controlled release, chemical reaction of the material or as support.
- the at least one material is preferably a gas or gas mixture.
- the composite of the invention is used for storage, this is preferably carried out in a temperature range from -200°C to +80°C. A temperature range of from -40°C to +80°C is more preferred.
- gas and liquid will be used in the interests of simplicity, but gas mixtures and liquid mixtures or liquid solutions are also encompassed by the term “gas” or "liquid”.
- Preferred gases are hydrogen, natural gas, town gas, hydrocarbons, in particular methane, ethane, ethyne, acetylene, propane, n-butane and also i-butane, carbon monoxide, carbon dioxide, nitrogen oxides, oxygen, sulfur oxides, halogens, halogenated hydrocarbons, NF 3 , SF 6 , ammonia, boranes, phosphanes, hydrogen sulfide, amines, formaldehyde, noble gases, in particular helium, neon, argon, krypton and xenon.
- the gas is particularly preferably carbon dioxide which is separated off from a gas mixture comprising carbon dioxide.
- the gas mixture preferably comprises carbon dioxide together with at least H 2 , CH 4 or carbon monoxide.
- the gas mixture comprises carbon monoxide in addition to carbon dioxide.
- Very particular preference is given to mixtures which comprise at least 10 and not more than 45% by volume of carbon dioxide and at least 30 and not more than 90% by volume of carbon monoxide.
- a preferred embodiment is pressure swing adsorption using a plurality of parallel adsorber reactors, with the adsorbent charge consisting entirely or partly of the material according to the invention.
- the adsorption phase for the C0 2 /CO separation preferably takes place at a C0 2 partial pressure of from 0.6 to 3 bar and a temperature of at least 20°C but not more than 70°C.
- the total pressure in the adsorber reactor concerned is usually reduced to values in the range from 100 mbar to 1 bar.
- the minimum pressure is more preferably 200 bar (absolute), in particular 300 bar (absolute).
- the gas is particularly preferably hydrogen or methane.
- the at least one material can also be a liquid.
- liquids are disinfectants, inorganic or organic solvents, fuels, in particular gasoline or diesel, hydraulic fluid, radiator fluid, brake fluid or an oil, in particular machine oil.
- the liquid can be a halogenated aliphatic or aromatic, cyclic or acyclic hydrocarbon or a mixture thereof.
- the liquid can be acetone, acetonitrile, aniline, anisole, benzene, benzonitrile, bromobenzene, butanol, tert-butanol, quinoline, chlorobenzene, chloroform, cyclohexane, diethylene glycol, diethyl ether, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, dioxane, glacial acetic acid, acetic anhydride, ethyl acetate, ethanol, ethylene carbonate, ethylene dichloride, ethylene glycol, ethylene glycol dimethyl ether, formamide, hexane, isopropanol, methanol, methoxypropanol, 3-methyl-1 -butanol, methylene chloride, methyl ethyl ketone, N- methylformamide, N-methylpyrrolidone, nitrobenzene, nitromethane, piperidine, propan
- the odorous substance is preferably a volatile organic or inorganic compound which comprises at least one of the elements nitrogen, phosphorus, oxygen, sulfur, fluorine, chlorine, bromine or iodine, or is an unsaturated or aromatic hydrocarbon or a saturated or unsaturated aldehyde or a ketone. More preferred elements are nitrogen, oxygen, phosphorus, sulfur, chlorine, bromine; particular preference is given to nitrogen, oxygen, phosphorus and sulfur.
- the odorous substance is ammonia, hydrogen sulfide, sulfur oxides, nitrogen oxides, ozone, cyclic or acyclic amines, thiols, thioethers and also aldehydes, ketones, esters, ethers, acids or alcohols.
- ammonia hydrogen sulfide
- organic acids preferably acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, caproic acid, heptanoic acid, lauric acid, pelargonic acid
- cyclic or acyclic hydrocarbons comprising nitrogen or sulfur and also saturated or unsaturated aldehydes such as hexanal, heptanal, octanal, nonanal, decanal, octenal or nonenal and in particular volatile aldehydes such as butyraldehyde, propionaldehyde, acetaldehyde and formaldehyde and additionally fuels such as gasoline, diesel (constituents).
- the odorous substances can also be fragrances which are used, for example, for producing perfumes.
- fragrances or oils which liberate such fragrances mention may be made by way of example of: essential oils, basil oil, geranium oil, mint oil, cananga tree oil, cardamom oil, lavender oil, peppermint oil, nutmeg oil, chamomile oil, eucalyptus oil, rosemary oil, lemon oil, lime oil, orange oil, bergamot oil, muscat sage oil, coriander oil, cypress oil, 1 ,1 -dimethoxy-2-phenylethane, 2,4-dimethyl-4- phenyltetrahydrofuran, dimethyltetrahydrobenzaldehyde, 2,6-dimethyl-7-octen-2-ol, 1 ,2-diethoxy-3,7-dimethyl-2,6-octadiene, phenylacetaldehyde, rose oxide, ethyl-2- methylpent
- a volatile odorous substance preferably has a boiling point or boiling point range of less than 300°C.
- the odorous substance is more preferably a readily volatile compound or mixture.
- the odorous substance particularly preferably has a boiling point or boiling range of less than 250°C, more preferably less than 230°C, particularly preferably less than 200°C.
- a volatile odorous substance preferably has a vapor pressure of more than 0.001 kPa (20°C).
- the odorous substance is more preferably a readily volatile compound or mixture.
- the odorous substance particularly preferably has a vapor pressure of more than 0.01 kPa (20°C), more preferably a vapor pressure of more than 0.05 kPa (20°C).
- the odorous substances particularly preferably have a vapor pressure of more than 0.1 kPa (20°C).
- Examples in which a chemical reaction can take place in the presence of the metal- organic framework of the invention are the alkoxylation of monools and polyols.
- the method of carrying out such alkoxylations is described in WO-A 03/035717 and WO-A 2005/03069.
- the porous metal-organic framework of the invention can be used for the epoxydation and also preparation of polyalkylene carbonates and hydrogen peroxide. Such reactions are described in WO-A 03/101975, WO-A 2004/037895 and US-A 2004/08161 1.
- the metal-organic framework of the invention can serve as support, in particular as support for a catalyst.
- the sulfur-impregnated composites of the present invention are suitable as sulfur electrode.
- the present invention therefore further provides a sulfur electrode comprising such a composite according to the invention.
- the present invention further provides for the use of a sulfur electrode according to the invention in an Li-sulfur battery and also provides an Li-sulfur battery comprising such a sulfur electrode.
- AI-MOF Al-terephthalic acid MOF: 1 100 m 2 /g determined by the Langmuir method
- Example 2 NaOH washing of the pyrolyzed Al-terephthalate
- Elemental analysis Al 0.1 % by weight; Na 0.61 % by weight
- Example 3 Loading of the material from Example 1 with sulfur. 1 .0 g of material from Example 1 and 6 g of sulfur are homogeneously mixed and heated at 180°C in an open apparatus for 6 hours. This gives 5.3 g of a solid dark gray substance which was milled to a fine powder by means of a ball mill.
- Example 4 Loading of the material from Example 2 with sulfur.
- Example 5 Production of an electrochemical cell according to the invention (electrode)
- the dispersion is applied by means of a doctor blade to Al foil and dried at 40°C under reduced pressure for 10 hours.
- Example 6 Production of a benchmark electrochemical cell 3.310 g of sulfur, 2.39 g of Super P, 0.19 g of KS 6, 0.25 g of Celvol binder are mixed together. The mixture is dispersed in a solvent mixture of 65% of H 2 0, 30% of isopropanol, 5% of 1 -methoxy-2-propanol. The dispersion is stirred for 10 hours.
- Example 7 Testing of the electrochemical cell according to the invention
- An electrochemical cell is built.
- Anode Li foil 50 ⁇ thick, separator Tonen 15 ⁇ thick, cathode with composite material as described above.
- Electrolyte 8% by weight of LiTFSI (LiN(S0 2 CF 3 ) 2 ), 4% by weight of LiN0 3 , 44% by weight of dioxolane and 44% by weight of dimethoxyethane.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP11821197.8A EP2611766A4 (en) | 2010-09-01 | 2011-08-18 | Process for producing carbon-comprising composite |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP10174939 | 2010-09-01 | ||
PCT/IB2011/053646 WO2012028989A1 (en) | 2010-09-01 | 2011-08-18 | Process for producing carbon-comprising composite |
EP11821197.8A EP2611766A4 (en) | 2010-09-01 | 2011-08-18 | Process for producing carbon-comprising composite |
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EP2611766A1 true EP2611766A1 (en) | 2013-07-10 |
EP2611766A4 EP2611766A4 (en) | 2014-04-30 |
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EP11821197.8A Withdrawn EP2611766A4 (en) | 2010-09-01 | 2011-08-18 | Process for producing carbon-comprising composite |
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EP (1) | EP2611766A4 (en) |
JP (1) | JP2013537877A (en) |
KR (1) | KR20130101038A (en) |
CN (1) | CN103180282A (en) |
AU (1) | AU2011298030A1 (en) |
BR (1) | BR112013004984A2 (en) |
CA (1) | CA2809928A1 (en) |
MX (1) | MX2013002219A (en) |
RU (1) | RU2013114186A (en) |
TW (1) | TW201223962A (en) |
WO (1) | WO2012028989A1 (en) |
Cited By (1)
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CN113488654A (en) * | 2021-07-27 | 2021-10-08 | 深圳齐锂纳米科技有限公司 | Graphene composite layered conductive agent supported by carbon nano tube |
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US9099744B2 (en) | 2011-03-31 | 2015-08-04 | Basf Se | Particulate porous carbon material and use thereof in lithium cells |
US9527751B2 (en) | 2011-11-11 | 2016-12-27 | Basf Se | Organotemplate-free synthetic process for the production of a zeolitic material of the CHA-type structure |
CN103456929B (en) * | 2013-09-04 | 2015-08-12 | 中南大学 | A kind of lithium sulfur battery anode material and preparation method thereof |
CN103500819B (en) * | 2013-09-18 | 2015-11-18 | 中南大学 | Carbon fiber/sulphur composite positive pole of a kind of finishing cellular carbon structure and preparation method thereof |
EP3049185B1 (en) * | 2013-09-23 | 2019-12-11 | Basf Se | Process for the recovery of components forming a metal-organic framework material |
WO2015137272A1 (en) * | 2014-03-11 | 2015-09-17 | 国立大学法人京都大学 | Porous structure and method for producing same, and method for producing composite metal nanoparticle |
WO2015171613A1 (en) * | 2014-05-05 | 2015-11-12 | Nivo Systems, Inc. | Carbon-enriched open framework composites, methods for producing and using such composites |
DE102015215088A1 (en) | 2015-08-07 | 2017-02-09 | Robert Bosch Gmbh | MOF-silicon-carbon composite anode material |
SG11201807928SA (en) * | 2016-03-17 | 2018-10-30 | Saudi Arabian Oil Co | Synthesis of transition-metal adamantane carboxylic salts and oxide nanocomposites |
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 (en) * | 2016-04-27 | 2018-10-26 | 长沙矿冶研究院有限责任公司 | A kind of nanometer rods porous carbon-sulphur composite positive pole and preparation method thereof, lithium-sulfur cell |
CN108336308A (en) * | 2017-01-20 | 2018-07-27 | 华为技术有限公司 | A kind of lithium-sulphur cell positive electrode protection materials and its application |
KR101969410B1 (en) * | 2017-02-28 | 2019-08-13 | 가천대학교 산학협력단 | Porous carbon composite structure and manufacturing method for the same |
CN110678419B (en) | 2017-05-19 | 2022-03-29 | 沙特***石油公司 | Synthesis of transition metal adamantane salt and oxide nanocomposites |
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 |
CN107768652A (en) * | 2017-10-25 | 2018-03-06 | 北京理工大学 | A kind of lithium sulfur battery anode material based on middle micro-diplopore metal oxide or spinelle and preparation method thereof |
CN109888236B (en) * | 2019-03-07 | 2021-09-28 | 南京邮电大学 | Preparation method of lithium-sulfur battery positive electrode material |
CN111302476B (en) * | 2020-02-27 | 2021-12-17 | 南京大学 | Preparation and application of magnetic material capable of activating persulfate and allowing MOF (metal-organic framework) in-situ growth of CNT (carbon nano tube) |
CN113725434B (en) * | 2021-08-06 | 2023-05-16 | 九江学院 | Nickel-based metal organic frame derived composite electrode and preparation method thereof |
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US5648508A (en) * | 1995-11-22 | 1997-07-15 | Nalco Chemical Company | Crystalline metal-organic microporous materials |
DE102005039654A1 (en) * | 2005-08-22 | 2007-03-01 | Basf Ag | Mesoporous organometallic framework |
WO2007118843A1 (en) * | 2006-04-18 | 2007-10-25 | Basf Se | Metal oxides produced from metal-organic framework materials |
AU2009223442B2 (en) * | 2008-03-12 | 2014-01-30 | Toyota Jidosha Kabushiki Kaisha | Sulfur-carbon material |
CN101587951A (en) * | 2008-05-23 | 2009-11-25 | 中国人民解放军63971部队 | Novel carbon-sulfur compound for lithium-sulfur battery |
CN101604580B (en) * | 2009-04-03 | 2011-10-05 | 中国科学院上海硅酸盐研究所 | Method for preparing porous carbon electrode material by method decomposing monophyletic compound at one step |
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- 2011-08-18 JP JP2013526572A patent/JP2013537877A/en not_active Withdrawn
- 2011-08-18 KR KR1020137007878A patent/KR20130101038A/en not_active Application Discontinuation
- 2011-08-18 RU RU2013114186/04A patent/RU2013114186A/en not_active Application Discontinuation
- 2011-08-18 WO PCT/IB2011/053646 patent/WO2012028989A1/en active Application Filing
- 2011-08-18 BR BR112013004984A patent/BR112013004984A2/en not_active IP Right Cessation
- 2011-08-18 MX MX2013002219A patent/MX2013002219A/en not_active Application Discontinuation
- 2011-08-18 AU AU2011298030A patent/AU2011298030A1/en not_active Abandoned
- 2011-08-18 CA CA2809928A patent/CA2809928A1/en not_active Abandoned
- 2011-08-18 EP EP11821197.8A patent/EP2611766A4/en not_active Withdrawn
- 2011-09-01 TW TW100131559A patent/TW201223962A/en unknown
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Cited By (2)
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CN113488654A (en) * | 2021-07-27 | 2021-10-08 | 深圳齐锂纳米科技有限公司 | Graphene composite layered conductive agent supported by carbon nano tube |
CN113488654B (en) * | 2021-07-27 | 2022-04-19 | 深圳齐锂纳米科技有限公司 | Graphene composite layered conductive agent supported by carbon nano tube |
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TW201223962A (en) | 2012-06-16 |
CA2809928A1 (en) | 2012-03-08 |
BR112013004984A2 (en) | 2016-05-31 |
RU2013114186A (en) | 2014-10-10 |
KR20130101038A (en) | 2013-09-12 |
WO2012028989A1 (en) | 2012-03-08 |
CN103180282A (en) | 2013-06-26 |
EP2611766A4 (en) | 2014-04-30 |
AU2011298030A1 (en) | 2013-03-21 |
JP2013537877A (en) | 2013-10-07 |
MX2013002219A (en) | 2013-06-03 |
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