JP6979056B2 - 遷移金属系触媒用の担体としての表面修飾炭酸カルシウム - Google Patents
遷移金属系触媒用の担体としての表面修飾炭酸カルシウム Download PDFInfo
- Publication number
- JP6979056B2 JP6979056B2 JP2019503674A JP2019503674A JP6979056B2 JP 6979056 B2 JP6979056 B2 JP 6979056B2 JP 2019503674 A JP2019503674 A JP 2019503674A JP 2019503674 A JP2019503674 A JP 2019503674A JP 6979056 B2 JP6979056 B2 JP 6979056B2
- Authority
- JP
- Japan
- Prior art keywords
- transition metal
- calcium carbonate
- pdcl
- metal compound
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 title claims description 479
- 239000003054 catalyst Substances 0.000 title claims description 77
- 229910052723 transition metal Inorganic materials 0.000 title claims description 66
- 150000003624 transition metals Chemical class 0.000 title claims description 47
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 146
- 239000000203 mixture Substances 0.000 claims description 129
- 150000003623 transition metal compounds Chemical class 0.000 claims description 116
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 105
- 101150003085 Pdcl gene Proteins 0.000 claims description 100
- 229940088417 precipitated calcium carbonate Drugs 0.000 claims description 86
- 239000007788 liquid Substances 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 73
- 239000002245 particle Substances 0.000 claims description 60
- 159000000007 calcium salts Chemical class 0.000 claims description 49
- 230000003197 catalytic effect Effects 0.000 claims description 49
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 44
- 239000007787 solid Substances 0.000 claims description 42
- 239000000243 solution Substances 0.000 claims description 41
- 239000000725 suspension Substances 0.000 claims description 40
- 239000011148 porous material Substances 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 238000006557 surface reaction Methods 0.000 claims description 33
- -1 transition metal salt Chemical class 0.000 claims description 32
- 229910021532 Calcite Inorganic materials 0.000 claims description 29
- 229910052763 palladium Inorganic materials 0.000 claims description 28
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 23
- 229910052753 mercury Inorganic materials 0.000 claims description 23
- 229910052697 platinum Inorganic materials 0.000 claims description 22
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 19
- VEJOYRPGKZZTJW-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;platinum Chemical compound [Pt].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VEJOYRPGKZZTJW-FDGPNNRMSA-N 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 238000006880 cross-coupling reaction Methods 0.000 claims description 16
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims description 15
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims description 15
- 238000004438 BET method Methods 0.000 claims description 15
- 238000005259 measurement Methods 0.000 claims description 15
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 14
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims description 14
- 238000001704 evaporation Methods 0.000 claims description 13
- 230000008020 evaporation Effects 0.000 claims description 13
- 239000002798 polar solvent Substances 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- 239000008187 granular material Substances 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- 239000012454 non-polar solvent Substances 0.000 claims description 11
- 150000002941 palladium compounds Chemical class 0.000 claims description 10
- 150000003058 platinum compounds Chemical class 0.000 claims description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 229910052709 silver Inorganic materials 0.000 claims description 9
- 239000004332 silver Substances 0.000 claims description 9
- HWZRXCHJIQVTPX-UHFFFAOYSA-N acetic acid;triphenylphosphanium;acetate Chemical compound CC(O)=O.CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 HWZRXCHJIQVTPX-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- CGMRCMMOCQYHAD-UHFFFAOYSA-J dicalcium hydroxide phosphate Chemical compound [OH-].[Ca++].[Ca++].[O-]P([O-])([O-])=O CGMRCMMOCQYHAD-UHFFFAOYSA-J 0.000 claims description 6
- 229910052762 osmium Inorganic materials 0.000 claims description 6
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 229910052586 apatite Inorganic materials 0.000 claims description 4
- 229910052589 chlorapatite Inorganic materials 0.000 claims description 4
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 claims description 4
- 229910052587 fluorapatite Inorganic materials 0.000 claims description 4
- 229910000392 octacalcium phosphate Inorganic materials 0.000 claims description 4
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 claims description 4
- YIGWVOWKHUSYER-UHFFFAOYSA-F tetracalcium;hydrogen phosphate;diphosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].OP([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O YIGWVOWKHUSYER-UHFFFAOYSA-F 0.000 claims description 4
- 238000006757 chemical reactions by type Methods 0.000 claims description 3
- 235000012438 extruded product Nutrition 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 150000001502 aryl halides Chemical class 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 136
- 239000002609 medium Substances 0.000 description 64
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 62
- 150000002500 ions Chemical class 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 239000011734 sodium Substances 0.000 description 45
- 239000010949 copper Substances 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 29
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 29
- 239000002002 slurry Substances 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000002156 mixing Methods 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 229910052802 copper Inorganic materials 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000007900 aqueous suspension Substances 0.000 description 15
- 238000009826 distribution Methods 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 10
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 9
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical group [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 9
- 239000005749 Copper compound Substances 0.000 description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 150000001880 copper compounds Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000011065 in-situ storage Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 238000004062 sedimentation Methods 0.000 description 8
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 7
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 7
- 229910001424 calcium ion Inorganic materials 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000004579 marble Substances 0.000 description 6
- 238000003801 milling Methods 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 229910016509 CuF 2 Inorganic materials 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 239000012876 carrier material Substances 0.000 description 5
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 5
- SFJMFSWCBVEHBA-UHFFFAOYSA-M copper(i)-thiophene-2-carboxylate Chemical compound [Cu+].[O-]C(=O)C1=CC=CS1 SFJMFSWCBVEHBA-UHFFFAOYSA-M 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000003842 bromide salts Chemical class 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 150000004673 fluoride salts Chemical class 0.000 description 3
- 238000007210 heterogeneous catalysis Methods 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 150000004694 iodide salts Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 238000002459 porosimetry Methods 0.000 description 3
- 239000003586 protic polar solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000004763 sulfides Chemical class 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 150000003567 thiocyanates Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000019738 Limestone Nutrition 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000003991 Rietveld refinement Methods 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 150000001243 acetic acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- JQOREDBDOLZSJY-UHFFFAOYSA-H bis(2,2-dioxo-1,3,2,4-dioxathialumetan-4-yl) sulfate hexahydrate Chemical compound O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O JQOREDBDOLZSJY-UHFFFAOYSA-H 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000014653 Carica parviflora Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000243321 Cnidaria Species 0.000 description 1
- 241000264877 Hippospongia communis Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101710156645 Peptide deformylase 2 Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical group [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 229910052915 alkaline earth metal silicate Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- KCHCWJJLJMJMJU-UHFFFAOYSA-K aluminum hydrogen sulfate sulfate hydrate Chemical compound S(=O)(=O)([O-])[O-].O.S(=O)(=O)([O-])O.[Al+3] KCHCWJJLJMJMJU-UHFFFAOYSA-K 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000007885 magnetic separation Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KVOIJEARBNBHHP-UHFFFAOYSA-N potassium;oxido(oxo)alumane Chemical compound [K+].[O-][Al]=O KVOIJEARBNBHHP-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Classifications
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/226—Sulfur, e.g. thiocarbamates
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/635—0.5-1.0 ml/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/638—Pore volume more than 1.0 ml/g
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0063—Granulating
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0209—Impregnation involving a reaction between the support and a fluid
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/28—Phosphorising
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/04—Substitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/02—Compounds of alkaline earth metals or magnesium
- C09C1/021—Calcium carbonates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/02—Compounds of alkaline earth metals or magnesium
- C09C1/021—Calcium carbonates
- C09C1/022—Treatment with inorganic compounds
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0027—Powdering
- B01J37/0036—Grinding
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/024—Multiple impregnation or coating
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
- B01J37/088—Decomposition of a metal salt
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/14—Pore volume
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/16—Pore diameter
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/20—Carbon compounds
- C07C2527/232—Carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/20—Carbon compounds
- C07C2527/232—Carbonates
- C07C2527/236—Hydroxy carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/08—Ethanol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/202—Ethylene glycol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/205—1,3-Propanediol; 1,2-Propanediol
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)1:99〜99:1の範囲の、少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比、
を示す。
(a)粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)及び炭酸カルシウム以外の少なくとも1つの水不溶性カルシウム塩を含む少なくとも1つの表面反応炭酸カルシウムを提供する工程;
(b)少なくとも1つの遷移金属化合物を提供する工程;及び
(c)液体媒体中、工程(a)で提供される表面反応炭酸カルシウム及び工程(b)で提供される遷移金属化合物を接触させて、表面反応炭酸カルシウム及び遷移金属化合物を含む混合物を得る工程、
を含み、
この表面反応炭酸カルシウムは、
(i)窒素及びISO9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)1:99〜99:1の範囲の、少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比、
を示す。
(a)1つ以上の反応物を提供する工程;
(b)本発明の触媒系を提供する工程;
(c)工程(b)で提供される触媒系の存在下で、工程(a)で提供される1つ以上の反応物を化学反応に供する工程、
を含む方法におけるこの触媒系の使用に関する。
本発明の意味において「粉砕天然炭酸カルシウム」(GNCC)は、天然源、例えば石灰岩、大理石、又はチョークから得られ、湿式及び/又は乾式処理、例えば粉砕、スクリーニング及び/又は分別、例えばサイクロン又は分類機によるものを通して加工処理された炭酸カルシウムである。
(i)窒素及びISO 9277:2010によるBET法を用いて測定される場合27〜180m2/g、好ましくは25〜160m2/g、より好ましくは30〜150m2/gの範囲の比表面積;
(ii)1〜75μm、好ましくは2〜50μm、より好ましくは3〜40μm、さらにより好ましくは4〜30μm、最も好ましくは5〜15μmの範囲のd50(体積);
(iii)2〜150μm、好ましくは4〜100μm、より好ましくは6〜80μm、さらにより好ましくは8〜60μm、最も好ましくは10〜30μmの範囲のd98(体積);及び/又は
(iv)水銀ポロシメトリー測定から計算される場合0.2〜2.0cm3/g、好ましくは0.4〜1.8cm3/g、最も好ましくは0.6〜1.6cm3/gの範囲の粒子内圧入比細孔容積。
(i)工程(a)の少なくとも1つの表面反応炭酸カルシウムは懸濁液の形態で液体媒体中に提供される;及び/又は
(ii)工程(b)の少なくとも1つの遷移金属化合物は、溶液又は懸濁液の形態で、好ましくは溶液の形態で液体媒体中に提供される。
本発明の方法の工程(a)によれば、表面反応炭酸カルシウムが提供される。表面反応炭酸カルシウムはまた、官能化炭酸カルシウム(FCC)とも呼ばれる。
(a)粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)の懸濁液を提供する工程;
(b)工程(a)で提供される懸濁液に、20℃で0以下のpKa値を有する又は20℃で0〜2.5のpKa値を有する少なくとも1つの酸を添加する工程;及び
(c)工程(a)で提供される懸濁液を工程(b)の前、工程(b)の間又は工程(b)の後にCO2で処理する工程。
(a)粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)を提供する工程;
(b)少なくとも1つの水溶性酸を提供する工程;
(c)ガス状のCO2を提供する工程;及び
(d)工程(a)で提供されるこのGNCC又はPCC、工程(b)で提供される少なくとも1つの酸及び工程(c)で提供されるガス状CO2を接触させる工程;
(i)工程(b)で提供される少なくとも1つの酸が、その第1の利用可能な水素のイオン化に関連して、20℃で2.5を超えて7以下のpKaを有し、対応するアニオンが、水溶性カルシウム塩を形成でき、この第1の利用可能な水素の損失時に形成されること;及び(ii)工程(b)で提供される少なくとも1つの水溶性酸と工程(a)で提供されるGNCC又はPCCとを接触させた後、水素含有塩の場合この第1の利用可能な水素のイオン化に関連して、20℃で7を超えるpKaを有し、その塩アニオンが水不溶性カルシウム塩を形成できる少なくとも1つの水溶性塩がさらに提供されることを特徴とする。
本発明による製造方法の工程(b)において、少なくとも1つの遷移金属化合物が提供される。
本発明による製造方法の工程(c)では、工程(a)で提供される表面反応炭酸カルシウム及び工程(b)で提供される遷移金属化合物を液体媒体中で接触させて、表面反応炭酸カルシウム及び遷移金属化合物を含む混合物を得る。
本発明による方法は、工程(c)で得られる混合物から液体媒体を除去する工程(d)を任意選択的に含んでもよい。
本発明の触媒系を製造する方法の工程(e)によれば、工程(c)の混合物又は任意の工程(d)の濃縮混合物は、400℃以下、好ましくは約170℃〜400℃、より好ましくは200℃〜300℃、さらにより好ましくは250〜310℃、最も好ましくは280℃〜320℃の温度で熱処理される。
本発明による触媒系は固体担体上の遷移金属化合物を含み、ここで固体担体は粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)及び炭酸カルシウム以外の少なくとも1つの水不溶性カルシウム塩を含む表面反応炭酸カルシウムである。この表面反応炭酸カルシウムは、CO2及び1つ以上のH3O+イオン供与体で処理された粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)の反応生成物であり、ここでこのCO2は、H3O+イオン供与体処理によってインサイチュで形成され及び/又は外部供給源から供給される。
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)重量で、1:99〜99:1の範囲の、少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比。
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)重量で1:99〜99:1の範囲の、少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比。
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)重量で、1:99〜99:1の範囲の、少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比、
ここで遷移金属化合物は、パラジウム化合物、白金化合物、銅化合物及びそれらの混合物からなる群から選択され、好ましくは遷移金属化合物は遷移金属塩又は遷移金属錯体である。
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)重量で1:99〜99:1の範囲の、少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比、
遷移金属化合物は、パラジウム化合物、白金化合物、銅化合物及びそれらの混合物からなる群から選択され、好ましくは遷移金属化合物は、遷移金属塩又は遷移金属錯体である。
本発明の触媒系は、多くの触媒反応において特に有用であることがわかった。例えば、C−Cクロスカップリング反応におけるより高い転化率及びグリセロール水素化分解におけるより高い収率が達成された。
(a)1つ以上の反応物を提供する工程;
(b)本発明の触媒系を提供する工程;
(c)工程(b)で提供される触媒系の存在下で、工程(a)で提供される1つ以上の反応物を化学反応に供する工程。
本願を通じて定義され、以下の実施例において決定されるパラメータは、以下の測定方法に基づく:
固形分含有量
懸濁液固形分含有量(「乾燥重量」としても知られている)を、以下の設定を伴ったMoisture Analyser MJ33(Mettler−Toledo,Switzerland)を使用して決定した:150℃の乾燥温度、質量が30秒間にわたって1mg超えて変化しない場合に自動でスイッチオフ、5gの懸濁液の標準乾燥。
本明細書における表面反応炭酸カルシウムの粒径は、体積に基づく粒径分布dx(体積)として記載される。Malvern Mastersizer 2000 Laser Diffraction System(Malvern Instruments Plc.,Great Britain)を用いて、体積で決定されたメジアン粒径d50(体積)及び体積で決定されたトップカット粒径d98(体積)を評価した。d50(体積)又はd98(体積)の値は、粒子のそれぞれ50体積%又は98体積%がこの値未満の直径を有するような直径値を示す。測定によって得られた生データは、1.57の粒子屈折率及び0.005の吸収指数で、ミー理論を使用して分析された。方法及び機器は、当業者に既知であり、充填剤及び顔料の粒径分布を決定するために一般に使用される。
比細孔容積は、ラプラススロート直径0.004μm(〜nm)に等しい水銀414MPa(60000psi)の最大印加圧力を有するMicromeritics Autopore V 9620水銀ポロシメータを使用する水銀圧入ポロシメトリー測定を用いて測定される。各圧力工程で使用される平衡時間は20秒である。サンプル材料を、分析のために3cm3チャンバ粉末ペネトロメータに密封する。データは、ソフトウェアPore−Compを用いて、水銀圧縮、ペネトロメータ拡張及びサンプル材料圧縮について補正する(Gane,P.A.C.,Kettle,J.P.,Matthews,G.P.and Ridgway,C.J.,「Void Space Structure of Compressible Polymer Spheres and Consolidated Calcium Carbonate Paper−Coating Formulations」,Industrial and Engineering Chemistry Research,35(5),1996,p1753−1764)。
本明細書を通して、表面反応炭酸カルシウム又は他の材料の比表面積(m2/g)は、当業者に周知のBET法(吸着ガスとして窒素を使用)を用いて決定する(ISO 9277:2010)。次いで、充填剤材料の総表面積(m2単位)は、処理対応サンプルの比表面積及び質量(g単位)との乗算によって得られる。
XRD実験は、回転可能なPMMAホルダーリングを用いてサンプルに対して実施される。サンプルは、Braggの法則に従うBruker D8 Advance粉末回折計で分析される。この回折計は、2.2kWのX線管、サンプルホルダー、θ−θゴニオメータ及びVANTEC−1検出器からなる。ニッケルフィルタCu Kα線をすべての実験に用いる。プロファイルは2θで毎分0.7°の走査速度を用いて自動的に記録されたチャートである。得られた粉末回折パターンを、ICDD PDF 2データベースの基準パターンに基づいて、DIFFRACsuiteソフトウェアパッケージEVA及びSEARCHを用いて鉱物含有量によって容易に分類できる。
Suzuki反応:サンプルを、Dionex UVD3400検出器、Dionex ASi−100オートサンプラ(10μL注入)、Dionex TCC−100 HPLCカラムサーモスタット(40℃)及びDG1210脱ガス装置を備えたDionex P680 HPLCポンプ(1.0ml・分−1)を用いて、Waters Symmetry Shield(商標)カラム(RP−8、3.5μM、4.6x50mM)で分析した。水相中の0〜100%のアセトニトリルの勾配(脱塩水中の0.1%ギ酸及び5%アセトニトリル)を溶離剤として使用した。
SRCC1(d 50 (体積)=4.4μm、d 98 (体積)=8.6μm、SSA=39.9m 2 g −1 )
SRCC1は、沈降法によって決定される場合に2μm未満の90%の質量基準の粒径分布を有するHustadmarmor,Norwayからの粉砕大理石炭酸カルシウムの固形分含有量を、水性懸濁液の総重量に基づいて15重量%の固形分含有量が得られるように調整することによって、混合容器中で粉砕炭酸カルシウムの水性懸濁液10リットルを調製することによって得られた。加えて、30重量%のリン酸を含有する溶液を調製した。スラリーを混合しながら、0.83kgのリン酸溶液を70℃の温度で10分間かけてこの懸濁液に添加した。最後に、リン酸を添加した後、スラリーを容器から取り出し、濾過し、乾燥する前に、スラリーをさらに5分間撹拌した。
SRCC2は、沈降法によって決定される場合に2μm未満の90%の質量基準の粒径分布を有するHustadmarmor,Norwayからの粉砕大理石炭酸カルシウムの固形分含有量を、水性懸濁液の総重量に基づいて15重量%の固形分含有量が得られるように調整することによって、混合容器中で粉砕炭酸カルシウムの水性懸濁液10リットルを調製することによって得られた。加えて、希リン酸と硫酸アルミニウム十六水和物とをブレンドすることによって溶液を調製したが、ここで、リン酸は30重量%の濃度を有し、硫酸アルミニウム十六水和物はニートなリン酸の質量5%で投与した。スラリーを混合しながら、1.7kgのリン酸/硫酸アルミニウム溶液を70℃の温度で10分間かけてこの懸濁液に添加した。最後に、リン酸を添加した後、スラリーを容器から取り出し、濾過し、乾燥する前に、スラリーをさらに5分間撹拌した。
SRCC3は、沈降法によって決定される場合に2μm未満の90%の質量基準の粒径分布を有するHustadmarmor,Norwayからの粉砕大理石炭酸カルシウムの固形分含有量を、水性懸濁液の総重量に基づいて10重量%の固形分含有量が得られるように調整することによって、混合容器中で粉砕炭酸カルシウムの水性懸濁液10リットルを調製することによって得られた。加えて、希リン酸とクエン酸とをブレンドすることによって溶液を調製し、ここでリン酸は29重量%の濃度を有し、クエン酸はニートなリン酸の質量10%で投与された。スラリーを混合しながら、1.65kgのリン酸/クエン酸溶液を70℃の温度で10分間かけてこの懸濁液に添加した。最後に、リン酸を添加した後、スラリーを容器から取り出し、濾過し、乾燥する前に、スラリーをさらに5分間撹拌した。
SRCC4は、沈降法によって決定される場合に2μm未満の90%の質量基準の粒径分布を有するHustadmarmor,Norwayからの粉砕大理石炭酸カルシウムの固形分含有量を、水性懸濁液の総重量に基づいて10重量%の固形分含有量が得られるように調整することによって、混合容器中で粉砕炭酸カルシウムの水性懸濁液10lを調製することによって得られた。加えて、30重量%のリン酸を含有する溶液を調製し、一方5重量%のクエン酸を含有する別の溶液を調製した。スラリーを混合しながら、1.60kgのリン酸溶液を70℃の温度で10分間かけてこの懸濁液に添加した。また、リン酸添加開始から2分後から0.05kgのクエン酸溶液もスラリーに添加した。最後に、リン酸を添加した後、スラリーを容器から取り出し、濾過し、乾燥する前に、スラリーをさらに5分間撹拌した。
SRCC5は、沈降法によって決定される場合に2μm未満の90%の質量基準の粒径分布を有するHustadmarmor,Norwayからの粉砕大理石炭酸カルシウムの固形分含有量を、水性懸濁液の総重量に基づいて10重量%の固形分含有量が得られるように調整することによって、混合容器中で粉砕炭酸カルシウムの水性懸濁液10リットルを調製することによって得られた。加えて、30重量%のリン酸を含有する溶液を調製し、一方5重量%のクエン酸を含有する別の溶液を調製した。スラリーを混合しながら、1.60kgのリン酸溶液を70℃の温度で10分間かけてこの懸濁液に添加した。また、リン酸添加開始から3分後から0.05kgのクエン酸溶液もスラリーに添加した。最後に、リン酸を添加した後、スラリーを容器から取り出し、濾過し、乾燥する前に、スラリーをさらに5分間撹拌した。
方法1:エタノール中の非水性含浸
担体(0.5g)のスラリーを、金属塩が既に溶解している有機溶媒(20ml)中で調製する。次いでスラリーを撹拌し(18時間)、濾過し、真空下に周囲温度で18時間乾燥する。この手順は、触媒充填量を増やすために一度繰り返すことができる。
担体(2g)のスラリーを、金属塩も溶解している有機溶媒(25ml)中で調製する。次いで、溶媒を一定の撹拌下で蒸発させて触媒を担体上に含浸させ、均一な粉末を得る。次いで、この材料を周囲温度で18時間真空下で乾燥し、300℃で焼成する。
金属の水溶性塩を最初に水(4ml)に溶解し、NaHCO3(飽和)を使用することによりpHを5.5〜6に調整する。溶液を水(8〜12ml)中の担体(1.8〜2.0g)のスラリーに添加する。混合物を30〜90分間70℃に加熱し、次いで室温に冷却する。触媒を濾別し、水(3×4ml)ですすぎ、周囲温度で18時間真空乾燥し、次いで300℃で3時間焼成する。この手順は、触媒充填量を増やすために数回繰り返すことができる。
水性含浸物C19(SRCC4)からの濾液溶液を、すべての可溶性金属塩が黒色物質として沈殿するまで(すなわち、溶液の完全な脱色まで)静置した。沈殿物を計量し、触媒充填量をこの値から計算して4.6重量%のPtとした。計算は金属白金から行った。
Suzuki反応(実施例A1〜A10、比較例CA1〜CA5)
ヨードベンゼンとフェニルボロン酸との間のカップリング反応は、様々な触媒充填量及び触媒タイプを用いて、Letters in Organic Chemistry,4,2007,13−15に従って行われた。典型的な反応では、0.45gのフェニルボロン酸(1.5当量、3.7mmol)を100mlの丸底フラスコに計量した。炭酸カリウム(2.9当量、7.3mmol、1.0g)を80mLの溶媒(水中40%エタノール)と共に混合物に添加した。フラスコをセプタムで閉じ、撹拌を開始し、フラスコを窒素流でパージした。次いでヨードベンゼン(0.50g、2.5mmol)を添加し、続いて予め計量した触媒を加えた(密閉バイアル中)。窒素パージを10〜15分間続けた。アリコート(約0.5ml)を混合物から一定間隔で取り出し、1mlのヘプタンで抽出し、UVダイオードアレイ検出器(238nm)を用いてHPLCによって分析した。転化率を表4にまとめる。
反応は、Catalysis Communications,13,2011,1−5に従って実施した。水(100mM)中の触媒(グリセロールに対して5モル%の活性金属)と20mlのグリセロールとの混合物を40バールの水素圧下に置き、次いで800rpmで撹拌しながら18時間200℃に加熱した。室温に冷却した後、サンプルを分析のために採取した。サンプルを濾過し、等量の5mMのH2SO4と混合した。触媒を濾別し、水(3×1ml)ですすぎ、真空乾燥した。反応混合物をHPLCにより分析して、出発材料(グリセロール)の量及び4つの主要反応生成物;乳酸(LA)、1,2−プロパンジオール(12−PD)、エチレングリコール(EG)及びエタノール(EtOH)の量を決定した。すべての場合において、これらの化合物は総ピーク面積の95%以上を占める。結果を表6にまとめる。
Claims (21)
- 固体担体上に遷移金属化合物を含む触媒系であって、前記触媒系は、不均一触媒作用下の水素化分解反応及びC−Cクロスカップリング反応から選択される反応を触媒し、前記固体担体は、粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)及び炭酸カルシウム以外の少なくとも1つの水不溶性カルシウム塩を含む表面反応炭酸カルシウムであり、前記表面反応炭酸カルシウムが、
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)重量で、1:99〜99:1の範囲の、前記少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比、
を示し、前記遷移金属が、チタン、ジルコニウム、ルテニウム、パラジウム、銀、オスミウム、パラジウム、金及びそれらの混合物から選択され、並びに前記遷移金属化合物が、分子遷移金属化合物、遷移金属塩、元素状遷移金を含む金属性遷移金属化合物又は遷移金属錯体である、触媒系。 - 前記少なくとも1つの水不溶性カルシウム塩が、リン酸オクタカルシウム、ヒドロキシルアパタイト、クロルアパタイト、フルオロアパタイト、カーボネートアパタイト及びそれらの混合物からなる群から選択される、請求項1に記載の触媒系。
- 前記少なくとも1つの水不溶性カルシウム塩と、カルサイト、アラゴナイト及び/又はバテライトとの前記比が、重量で、1:9〜9:1の範囲である、請求項1又は2に記載の触媒系。
- 前記遷移金属化合物が、パラジウム化合物、白金化合物及びそれらの混合物からなる群から選択される、請求項1〜3のいずれか一項に記載の触媒系。
- 前記遷移金属化合物が、元素状パラジウム、Pd(acac)2、Na2PdCl4、Pd(OAc)2、Pd(PPh3)4、PdCl2(PPh3)2、(dppf)PdCl2、(dppe)PdCl2、(dppp)PdCl2、(dppb)PdCl2、PdCl2、(C3H5PdCl)2、ビス(アセテート)−トリフェニル−ホスフィン−パラジウム(II)、Pd(dba)2、Pd(H2NCH2CH2NH2)Cl2、元素状白金、Na2PtCl6Pt(acac)2、Na2PtCl4、H2PtCl6、(NH4)2[PtCl6]、PtO2・H2O、PtCl4及びそれらの混合物からなる群から選択される、請求項1〜4のいずれか一項に記載の触媒系。
- 前記表面反応炭酸カルシウムが、
(i)窒素及びISO 9277:2010に従うBET法を用いて測定される場合27〜180m2/gの範囲の比表面積;
(ii)1〜75μmの範囲の体積メジアン粒径d50(体積);
(iii)2〜150μmの範囲のトップカット粒径d98(体積);及び/又は
(iv)水銀ポロシメトリー測定から計算される場合0.2〜2.0cm3/gの範囲の粒子内圧入比細孔容積、
を有する、請求項1〜5のいずれか一項に記載の触媒系。 - 前記触媒系が、遷移金属化合物と表面反応炭酸カルシウムとの反応生成物1つ以上をさらに含む、請求項1〜6のいずれか一項に記載の触媒系。
- 前記遷移金属化合物及び/又は前記1つ以上の反応生成物の含有量が、前記触媒系の総重量あたりの前記遷移金属化合物の重量に基づいて、0.1〜60重量%の範囲である、請求項1〜7のいずれか一項に記載の触媒系。
- 固体担体上に遷移金属化合物を含む触媒系を製造するための方法であって、
(a)粉砕天然炭酸カルシウム(GNCC)又は沈降炭酸カルシウム(PCC)及び炭酸カルシウム以外の少なくとも1つの水不溶性カルシウム塩を含む少なくとも1つの表面反応炭酸カルシウムを提供する工程;
(b)少なくとも1つの遷移金属化合物を提供する工程;及び
(c)液体媒体中、工程(a)で提供される前記表面反応炭酸カルシウム及び工程(b)で提供される前記遷移金属化合物を接触させて、表面反応炭酸カルシウム及び遷移金属化合物を含む混合物を得る工程;
を含み、
前記表面反応炭酸カルシウムは、
(i)窒素及びISO9277:2010に従うBET法を用いて測定される場合15〜200m2/gの比表面積;
(ii)水銀ポロシメトリー測定から計算される場合0.1〜2.3cm3/gの範囲の粒子内圧入比細孔容積;及び
(iii)重量で1:99〜99:1の範囲の、前記少なくとも1つの水不溶性カルシウム塩とカルサイト、アラゴナイト及び/又はバテライトとの比
を示し、前記遷移金属が、チタン、ジルコニウム、ルテニウム、パラジウム、銀、オスミウム、パラジウム、金及びそれらの混合物から選択され、並びに前記遷移金属化合物が、分子遷移金属化合物、遷移金属塩、元素状遷移金を含む金属性遷移金属化合物又は遷移金属錯体である、方法。 - (i)工程(a)の前記少なくとも1つの表面反応炭酸カルシウムが、懸濁液の形態で液体媒体中に提供される;及び/又は
(ii)工程(b)の前記少なくとも1つの遷移金属化合物が、溶液又は懸濁液の形態で液体媒体中に提供される、
請求項9に記載の方法。 - 前記方法が、工程(c)の前記混合物に含有される前記液体媒体の少なくとも一部を蒸発及び/又は濾過によって除去して濃縮混合物を得る工程(d)をさらに含む、請求項9又は10に記載の方法。
- 前記方法が、工程(c)の混合物又は工程(d)の濃縮混合物を、400℃未満の温度で熱処理する工程(e)をさらに含む、請求項9〜11のいずれか一項に記載の方法。
- 前記遷移金属化合物が、パラジウム化合物、白金化合物及びそれらの混合物からなる群から選択される、請求項9〜12のいずれか一項に記載の方法。
- 前記遷移金属化合物が、元素状パラジウム、Pd(acac)2、Na2PdCl4、Pd(OAc)2、Pd(PPh3)4、PdCl2(PPh3)2、(dppf)PdCl2、(dppe)PdCl2、(dppp)PdCl2、(dppb)PdCl2、PdCl2、(C3H5PdCl)2、ビス(アセテート)−トリフェニル−ホスフィン−パラジウム(II)、Pd(dba)2、Pd(H2NCH2CH2NH2)Cl2、元素状白金、Na2PtCl6Pt(acac)2、Na2PtCl4、H2PtCl6、(NH4)2[PtCl6]、PtO2・H2O、PtCl4及びそれらの混合物からなる群から選択される、請求項9〜13のいずれか一項に記載の方法。
- 前記液体媒体が、非極性溶媒、極性溶媒又はそれらの混合物である、請求項9〜14のいずれか一項に記載の方法。
- 前記遷移金属化合物が、Na2PdCl4及び/又はNa2PtCl4であり、前記液体媒体が極性溶媒であり;及び/又は前記遷移金属化合物がPd(acac)2及び/又はPt(acac)2であり、前記液体媒体は非極性溶媒である、請求項9〜15のいずれか一項に記載の方法。
- (a)1つ以上の反応物を提供する工程;
(b)請求項1〜8のいずれか一項に記載の前記触媒系を提供する工程;
(c)工程(b)で提供される前記触媒系の存在下で、工程(a)で提供される前記1つ以上の反応物を化学反応に供する工程、
を含む方法における請求項1〜8のいずれか一項に記載の触媒系の使用。 - 前記方法が、工程(c)の前記化学反応の後に前記触媒系を回収し、前記遷移金属をリサイクルする工程(d)をさらに含む、請求項17に記載の使用。
- 工程(c)の前記化学反応が、水素化分解反応、C−Cカップリング及びC−Cクロスカップリング、C−Nクロスカップリング、C−Oクロスカップリング、C−Sクロスカップリング、付加環化反応、アルケン水素化及びアルキン水素化、アリル置換、ニトロ基の還元及びハロゲン化アリールのヒドロカルボニル化の反応タイプの1つ以上から選択される、請求項17又は18に記載の使用。
- 遷移金属系触媒用の担体としての、請求項1〜3又は6のいずれか一項に記載の表面反応炭酸カルシウムの使用。
- 請求項1〜8のいずれか一項に記載の触媒系を含む顆粒、成形品又は押出物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16181100.5 | 2016-07-25 | ||
EP16181100.5A EP3275537A1 (en) | 2016-07-25 | 2016-07-25 | Surface-modified calcium carbonate as carrier for transition metal-based catalysts |
US201662369290P | 2016-08-01 | 2016-08-01 | |
US62/369,290 | 2016-08-01 | ||
PCT/EP2017/067974 WO2018019630A1 (en) | 2016-07-25 | 2017-07-17 | Surface-modified calcium carbonate as carrier for transition metal-based catalysts |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2019523127A JP2019523127A (ja) | 2019-08-22 |
JP2019523127A5 JP2019523127A5 (ja) | 2020-07-30 |
JP6979056B2 true JP6979056B2 (ja) | 2021-12-08 |
Family
ID=56551222
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019503674A Active JP6979056B2 (ja) | 2016-07-25 | 2017-07-17 | 遷移金属系触媒用の担体としての表面修飾炭酸カルシウム |
Country Status (14)
Country | Link |
---|---|
US (1) | US10875014B2 (ja) |
EP (2) | EP3275537A1 (ja) |
JP (1) | JP6979056B2 (ja) |
KR (1) | KR102401444B1 (ja) |
CN (1) | CN109475849A (ja) |
AU (1) | AU2017304362B2 (ja) |
BR (1) | BR112019001472B1 (ja) |
CA (1) | CA3030065A1 (ja) |
DK (1) | DK3487619T3 (ja) |
FI (1) | FI3487619T3 (ja) |
MX (1) | MX2019001061A (ja) |
PL (1) | PL3487619T3 (ja) |
RU (1) | RU2742335C2 (ja) |
WO (1) | WO2018019630A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL2386682T3 (pl) * | 2010-04-27 | 2014-08-29 | Omya Int Ag | Sposób wytwarzania materiałów strukturalnych z użyciem nanowłóknistych żeli celulozowych |
US20230347325A1 (en) * | 2019-09-26 | 2023-11-02 | Omya International Ag | Gncc and/or pcc as a catalytic carrier for metal species |
KR20220069988A (ko) * | 2019-09-26 | 2022-05-27 | 옴야 인터내셔널 아게 | 금속 화학종을 위한 촉매 담체로서의 srcc |
CN110743582B (zh) * | 2019-10-23 | 2020-10-02 | 广东海洋大学 | 海洋生物废弃物牡蛎壳负载钯催化剂的制备及应用 |
BR112023024758A2 (pt) * | 2021-07-12 | 2024-02-15 | Omya Int Ag | Processo para preparar um álcool através de uma reação de autocondensação de guerbet na fase gasosa, e, uso de um carbonato de cálcio reagido em superfície |
EP4306210A1 (en) * | 2022-07-12 | 2024-01-17 | Omya International AG | High surface area pcc as a catalyst carrier for platinum compounds |
CN116351476A (zh) * | 2022-12-18 | 2023-06-30 | 石河子大学 | 一种用于催化乙炔氢氯化反应的配体-铜基催化剂及其制备方法和应用 |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992021613A1 (en) * | 1991-06-04 | 1992-12-10 | Minerals Technologies, Inc. | Precipitated calcium carbonate particles from basic calcium carbonate |
DE4423738A1 (de) | 1994-07-06 | 1996-01-11 | Basf Ag | Verfahren und Katalysator zur Selektivhydrierung von Butindiol zu Butendiol |
US5625084A (en) * | 1996-01-31 | 1997-04-29 | Arco Chemical Technology, L.P. | Vapor phase oxidation of propylene to propylene oxide |
US5703254A (en) | 1996-10-02 | 1997-12-30 | Arco Chemical Technology, L.P. | Propylene oxide process using mixed precious metal catalyst supported on alkaline earth metal carbonate |
US5780657A (en) | 1997-06-23 | 1998-07-14 | Arco Chemical Technology, L.P. | Propylene epoxidation using chloride-containing silver catalysts |
CH692506A5 (de) * | 1997-12-18 | 2002-07-15 | Eprova Ag | Verfahren zur Herstellung von Aminocyanacetamid. |
FR2787802B1 (fr) | 1998-12-24 | 2001-02-02 | Pluss Stauffer Ag | Nouvelle charge ou pigment ou mineral traite pour papier, notamment pigment contenant du caco3 naturel, son procede de fabrication, compositions les contenant, et leurs applications |
JP2000271488A (ja) * | 1999-03-25 | 2000-10-03 | Maruo Calcium Co Ltd | 光触媒性ウィスカー及び光触媒性組成物 |
CN100457258C (zh) | 2002-09-30 | 2009-02-04 | 国际壳牌研究有限公司 | 制备银基环氧化催化剂的碳酸钙载体 |
FR2852600B1 (fr) | 2003-03-18 | 2005-06-10 | Nouveau pigment mineral contenant du carbonate de calcium, suspension aqueuse le contenant et ses usages | |
US20050027134A1 (en) * | 2003-07-29 | 2005-02-03 | Saudi Basic Industries Corporation | Support for a catalyst for direct oxidation of propylene to propylene oxide, method of making and method of using catalyst |
FR2871474B1 (fr) | 2004-06-11 | 2006-09-15 | Omya Development Ag | Nouveau pigment mineral sec contenant du carbonate de calcium, suspension aqueuse le contenant et ses usages |
US9632665B2 (en) * | 2004-09-08 | 2017-04-25 | Universal Electronics Inc. | System and method for flexible configuration of a controlling device |
PT2070991E (pt) | 2007-12-12 | 2010-10-25 | Omya Development Ag | Processo para produção de carbonato de cálcio precipitado reagido em superfície |
CN101811042A (zh) * | 2009-02-25 | 2010-08-25 | 中国中化股份有限公司 | 一种选择性加氢催化剂及其制备方法与应用 |
ME01449B (me) | 2009-06-15 | 2014-04-20 | Omya Development Ag | POSTUPAK ZA DOBIJANJE POVRŠINSKI IZREAGOVANOG KALCIJUM KARBONATA l NJEGOVA UPOTREBA |
ATE545682T1 (de) | 2009-06-15 | 2012-03-15 | Omya Development Ag | Verfahren zur herstellung eines an der oberfläche reagierten calciumcarbonats, das eine schwache säure anwendet |
DK2371766T3 (da) | 2010-04-01 | 2013-05-06 | Omya Development Ag | Fremgangsmåde til at opnå præcipiteret calciumcarbonat |
ES2540248T3 (es) | 2010-10-26 | 2015-07-09 | Omya Development Ag | Producción de carbonato de calcio precipitado de alta pureza |
PL2524898T3 (pl) | 2011-05-16 | 2016-02-29 | Omya Int Ag | Sposób wytwarzania strącanego węglanu wapnia z odpadów ze ścieralni |
CN102553578A (zh) * | 2012-02-22 | 2012-07-11 | 西安凯立化工有限公司 | 一种Pt/CaCO3负载型催化剂的制备方法 |
US9428398B2 (en) | 2012-03-23 | 2016-08-30 | Omya International Ag | Process for preparing scalenohedral precipitated calcium carbonate |
JP6279564B2 (ja) | 2012-06-22 | 2018-02-14 | ディーエスエム アイピー アセッツ ビー.ブイ. | リンドラー型触媒の部分水素化のための使用 |
EP2719376B1 (en) * | 2012-10-12 | 2015-03-04 | Omya International AG | Gastroretentive drug formulation and delivery systems and their method of preparation using functionalized calcium carbonate |
ES2628371T3 (es) * | 2012-10-12 | 2017-08-02 | Omya International Ag | Formulación de forma farmacéutica sólida de disgregación rápida que comprende carbonato de calcio funcionalizado y método para su fabricación |
JP5839722B2 (ja) * | 2013-02-25 | 2016-01-06 | 株式会社宇宙環境保全センター | 金属イオン配合炭酸カルシウム含有光触媒性複合組成物の製造方法 |
PT2840065T (pt) | 2013-08-20 | 2017-01-31 | Omya Int Ag | Processo para obtenção de carbonato de cálcio precipitado |
EP2921173A1 (en) * | 2014-03-21 | 2015-09-23 | Omya International AG | Surface-reacted calcium carbonate for desensitizing teeth |
US10351710B2 (en) * | 2014-05-30 | 2019-07-16 | Omya International Ag | Method for the production of granules comprising surface-reacted calcium carbonate |
HUE034663T2 (hu) * | 2014-06-20 | 2018-02-28 | Omya Int Ag | Eljárás szagtalanításra |
EP2997833B1 (en) * | 2014-09-22 | 2018-01-31 | Omya International AG | Surface-reacted calcium carbonate for use as anti-caking agent |
EP3034070A1 (en) * | 2014-12-18 | 2016-06-22 | Omya International AG | Method for the production of a pharmaceutical delivery system |
EP3045042A1 (en) * | 2015-01-15 | 2016-07-20 | Omya International AG | Use of surface-reacted calcium carbonate as carrier for agrochemical compounds |
EP3176222A1 (en) | 2015-12-01 | 2017-06-07 | Omya International AG | Method for the production of granules comprising surface-reacted calcium carbonate |
-
2016
- 2016-07-25 EP EP16181100.5A patent/EP3275537A1/en not_active Withdrawn
-
2017
- 2017-07-17 PL PL17739291.7T patent/PL3487619T3/pl unknown
- 2017-07-17 EP EP17739291.7A patent/EP3487619B1/en active Active
- 2017-07-17 FI FIEP17739291.7T patent/FI3487619T3/fi active
- 2017-07-17 CN CN201780045749.XA patent/CN109475849A/zh active Pending
- 2017-07-17 MX MX2019001061A patent/MX2019001061A/es unknown
- 2017-07-17 RU RU2019104891A patent/RU2742335C2/ru active
- 2017-07-17 BR BR112019001472-1A patent/BR112019001472B1/pt active IP Right Grant
- 2017-07-17 JP JP2019503674A patent/JP6979056B2/ja active Active
- 2017-07-17 AU AU2017304362A patent/AU2017304362B2/en not_active Ceased
- 2017-07-17 US US16/307,819 patent/US10875014B2/en active Active
- 2017-07-17 WO PCT/EP2017/067974 patent/WO2018019630A1/en unknown
- 2017-07-17 KR KR1020197005327A patent/KR102401444B1/ko active IP Right Grant
- 2017-07-17 DK DK17739291.7T patent/DK3487619T3/da active
- 2017-07-17 CA CA3030065A patent/CA3030065A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
KR20190033583A (ko) | 2019-03-29 |
US20190262807A1 (en) | 2019-08-29 |
BR112019001472B1 (pt) | 2022-10-04 |
DK3487619T3 (da) | 2023-11-06 |
CA3030065A1 (en) | 2018-02-01 |
BR112019001472A2 (pt) | 2019-05-07 |
WO2018019630A1 (en) | 2018-02-01 |
AU2017304362B2 (en) | 2021-08-05 |
AU2017304362A1 (en) | 2019-01-03 |
RU2019104891A3 (ja) | 2020-08-25 |
JP2019523127A (ja) | 2019-08-22 |
RU2019104891A (ru) | 2020-08-25 |
PL3487619T3 (pl) | 2024-02-19 |
US10875014B2 (en) | 2020-12-29 |
KR102401444B1 (ko) | 2022-05-25 |
EP3487619B1 (en) | 2023-10-04 |
EP3487619A1 (en) | 2019-05-29 |
MX2019001061A (es) | 2019-04-25 |
EP3275537A1 (en) | 2018-01-31 |
FI3487619T3 (fi) | 2023-10-18 |
CN109475849A (zh) | 2019-03-15 |
RU2742335C2 (ru) | 2021-02-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6979056B2 (ja) | 遷移金属系触媒用の担体としての表面修飾炭酸カルシウム | |
WO2021058508A1 (en) | Srcc as a catalytic carrier for metal species | |
EP3487939B1 (en) | Process for preparing surface-reacted calcium carbonate | |
RU2729612C1 (ru) | Гранулированный активный оксид алюминия | |
EP4222134A1 (en) | Method for performing a condensation reaction using a surface-reacted calcium carbonate catalyst | |
WO2021058558A1 (en) | Gncc and/or pcc as a catalytic carrier for metal species | |
EP4306210A1 (en) | High surface area pcc as a catalyst carrier for platinum compounds | |
US20240042421A1 (en) | Srcc as a catalytic carrier for metal species | |
CN117398993A (zh) | 作为铂化合物的催化剂载体的高表面积pcc | |
CA3218416A1 (en) | Process for preparing an alcohol using a surface-reacted calcium carbonate catalyst | |
KR20210153658A (ko) | 표면 반응된 탄산칼슘의 제조 방법 | |
Farhangb et al. | Palladium nanoparticles supported on natural nanozeolite clinoptilolite as a catalyst for ligand and copper-free C–C and C–O cross coupling reactions in aqueous medium | |
GB1559917A (en) | Process for preparing shaped particles from rehydratable alumina |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200622 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200622 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20210308 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210323 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210524 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210706 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210924 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20211102 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20211112 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6979056 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |