CN105214686B - Carbon-supported multi-component catalyst and preparation method and application thereof - Google Patents
Carbon-supported multi-component catalyst and preparation method and application thereof Download PDFInfo
- Publication number
- CN105214686B CN105214686B CN201510624141.5A CN201510624141A CN105214686B CN 105214686 B CN105214686 B CN 105214686B CN 201510624141 A CN201510624141 A CN 201510624141A CN 105214686 B CN105214686 B CN 105214686B
- Authority
- CN
- China
- Prior art keywords
- catalyst
- palladium
- charcoal
- presoma
- transition metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 89
- 238000002360 preparation method Methods 0.000 title abstract description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 62
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 50
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 28
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 24
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 23
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 23
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012964 benzotriazole Substances 0.000 claims abstract description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 96
- 238000003756 stirring Methods 0.000 claims description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 35
- 239000003610 charcoal Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000002243 precursor Substances 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 16
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 16
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 14
- 239000012065 filter cake Substances 0.000 claims description 14
- 238000005470 impregnation Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000010792 warming Methods 0.000 claims description 14
- 239000000706 filtrate Substances 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 150000003053 piperidines Chemical class 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229940031098 ethanolamine Drugs 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Inorganic materials [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 claims description 4
- LBVWQMVSUSYKGQ-UHFFFAOYSA-J zirconium(4+) tetranitrite Chemical compound [Zr+4].[O-]N=O.[O-]N=O.[O-]N=O.[O-]N=O LBVWQMVSUSYKGQ-UHFFFAOYSA-J 0.000 claims description 4
- 229910019626 (NH4)6Mo7O24 Inorganic materials 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 238000006073 displacement reaction Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 16
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 22
- 238000006722 reduction reaction Methods 0.000 description 16
- 230000009467 reduction Effects 0.000 description 13
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- 238000007598 dipping method Methods 0.000 description 11
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000005070 sampling Methods 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 8
- 229960003975 potassium Drugs 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 235000015165 citric acid Nutrition 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 7
- 229910002651 NO3 Inorganic materials 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- -1 polypropylene Polymers 0.000 description 6
- 239000001508 potassium citrate Substances 0.000 description 6
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical group [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 6
- 235000011082 potassium citrates Nutrition 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000013528 metallic particle Substances 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010719 annulation reaction Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 229960002635 potassium citrate Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- STLFUWRAUIJKJC-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;zinc Chemical compound [Zn].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O STLFUWRAUIJKJC-BTVCFUMJSA-N 0.000 description 1
- 229910003208 (NH4)6Mo7O24·4H2O Inorganic materials 0.000 description 1
- NAVWVHRQSDHCHD-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;potassium Chemical compound [K].OC(=O)CC(O)(C(O)=O)CC(O)=O NAVWVHRQSDHCHD-UHFFFAOYSA-N 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229910003206 NH4VO3 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001239 high-resolution electron microscopy Methods 0.000 description 1
- VBNTXGMDMADBQF-UHFFFAOYSA-N hydrazine zinc hydrate Chemical compound O.[Zn].NN VBNTXGMDMADBQF-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(II) nitrate Inorganic materials [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 150000003941 n-butylamines Chemical class 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(II) nitrate Inorganic materials [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- DFCYEXJMCFQPPA-UHFFFAOYSA-N scandium(III) nitrate Inorganic materials [Sc+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O DFCYEXJMCFQPPA-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Catalysts (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510624141.5A CN105214686B (en) | 2015-09-25 | 2015-09-25 | Carbon-supported multi-component catalyst and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510624141.5A CN105214686B (en) | 2015-09-25 | 2015-09-25 | Carbon-supported multi-component catalyst and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105214686A CN105214686A (en) | 2016-01-06 |
CN105214686B true CN105214686B (en) | 2018-06-29 |
Family
ID=54984154
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510624141.5A Active CN105214686B (en) | 2015-09-25 | 2015-09-25 | Carbon-supported multi-component catalyst and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105214686B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106179400A (en) * | 2016-06-30 | 2016-12-07 | 浙江工业大学 | Active carbon supported composite metal catalyst and preparation method and application thereof |
CN109382095A (en) * | 2018-11-13 | 2019-02-26 | 江西理工大学 | Second benzene hydrogenation prepares the catalyst and preparation method, application of ethyl cyclohexane |
CN109529820B (en) * | 2018-12-19 | 2021-11-30 | 利安隆科润(浙江)新材料有限公司 | Preparation method of catalyst for preparing benzotriazole ultraviolet absorber by catalytic hydrogenation |
CN112295569B (en) * | 2019-07-26 | 2023-05-12 | 中国石油化工股份有限公司 | Catalyst for preparing aniline by one-step ammoniation of benzene and preparation method thereof |
CN111545240B (en) * | 2020-05-29 | 2023-03-31 | 西安凯立新材料股份有限公司 | In-situ one-pot preparation method of Pt/Fe 3 O 4 Method and application of/C-N catalyst |
CN112138651B (en) * | 2020-09-30 | 2023-03-03 | 西安凯立新材料股份有限公司 | Platinum-carbon catalyst for synthesizing flufenacet intermediate and preparation method and application thereof |
CN115212891A (en) * | 2021-04-21 | 2022-10-21 | 浙江微通催化新材料有限公司 | Preparation method of carbon-supported Pd-Ni bimetallic catalyst and application of carbon-supported Pd-Ni bimetallic catalyst in Suzuki coupling reaction |
CN114345328A (en) * | 2021-12-30 | 2022-04-15 | 利安隆科润(浙江)新材料有限公司 | Catalyst, preparation method and application thereof |
CN114797870B (en) * | 2022-04-14 | 2023-06-09 | 浙江师范大学 | Catalyst for preparing m-xylylenediamine by hydrogenation of m-phthalonitrile, and preparation method and application thereof |
CN115178257B (en) * | 2022-06-13 | 2024-06-07 | 浙江工业大学 | Preparation method and application of Pt-Ru-La/C multi-metal catalyst |
CN115771889B (en) * | 2022-11-22 | 2024-05-10 | 西安英利科电气科技有限公司 | In-situ combustion synthesis method of cobalt-iron loaded porous carbon sponge wave-absorbing material |
CN115920975B (en) * | 2022-12-29 | 2024-06-07 | 浙江工业大学 | Preparation method and application of defect MOFs material encapsulated noble metal Pt catalyst |
CN117210167B (en) * | 2023-11-08 | 2024-01-09 | 广东鑫瑞新材料有限公司 | Nanofiber ceramic high-heat-insulation sun-shading adhesive film and preparation method and application thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5276161A (en) * | 1989-09-20 | 1994-01-04 | Ciba-Geigy Corporation | Process for the preparation of benzotriazoles |
EP0794179A1 (en) * | 1996-03-07 | 1997-09-10 | Eastman Kodak Company | Process for the preparation of benzotriazole derivatives |
CN101703935A (en) * | 2009-11-19 | 2010-05-12 | 浙江工业大学 | Load type metal catalyst and preparation method thereof |
CN102139223A (en) * | 2011-03-02 | 2011-08-03 | 浙江工业大学 | Loaded double-metal catalyst and application thereof |
-
2015
- 2015-09-25 CN CN201510624141.5A patent/CN105214686B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5276161A (en) * | 1989-09-20 | 1994-01-04 | Ciba-Geigy Corporation | Process for the preparation of benzotriazoles |
EP0794179A1 (en) * | 1996-03-07 | 1997-09-10 | Eastman Kodak Company | Process for the preparation of benzotriazole derivatives |
CN101703935A (en) * | 2009-11-19 | 2010-05-12 | 浙江工业大学 | Load type metal catalyst and preparation method thereof |
CN102139223A (en) * | 2011-03-02 | 2011-08-03 | 浙江工业大学 | Loaded double-metal catalyst and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN105214686A (en) | 2016-01-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105214686B (en) | Carbon-supported multi-component catalyst and preparation method and application thereof | |
Liang et al. | Construction of CdS@ UIO-66-NH2 core-shell nanorods for enhanced photocatalytic activity with excellent photostability | |
Shen et al. | Noble-metal-free MoS2 co-catalyst decorated UiO-66/CdS hybrids for efficient photocatalytic H2 production | |
Qi et al. | In-situ synthesis of metal nanoparticles@ metal− organic frameworks: Highly effective catalytic performance and synergistic antimicrobial activity | |
Xia et al. | Construction of ultrathin C3N4/Bi4O5I2 layered nanojunctions via ionic liquid with enhanced photocatalytic performance and mechanism insight | |
CN103949286B (en) | A kind of for the MOFs noble metal MOFs catalyst of selective hydrogenation, preparation method and its usage | |
Pan et al. | Well-constructed Ni@ CN material derived from di-ligands Ni-MOF to catalyze mild hydrogenation of nitroarenes | |
Trivedi et al. | Metal–organic framework MIL-101 supported bimetallic Pd–Cu nanocrystals as efficient catalysts for chromium reduction and conversion of carbon dioxide at room temperature | |
Liu et al. | Mild, selective and switchable transfer reduction of nitroarenes catalyzed by supported gold nanoparticles | |
CN107008290B (en) | Preparation method and catalytic application of monoatomic dispersion palladium-based catalyst | |
CN106732564B (en) | Aromatic hydrogenation rhodium/activated-carbon catalyst preparation method and application | |
Yu et al. | Enhanced visible light photocatalytic non-oxygen coupling of amines to imines integrated with hydrogen production over Ni/CdS nanoparticles | |
US20080220296A1 (en) | PtRu core-shell nanoparticles for heterogeneous catalysis | |
CN111185237B (en) | Selective hydrogenation catalyst, preparation method and application thereof | |
CN1970143A (en) | Method for preparing high-activity hydrogenation catalyst nano Ru/C | |
Filiz | The role of catalyst support on activity of copper oxide nanoparticles for reduction of 4-nitrophenol | |
CN105833864B (en) | A kind of support type nano spherical particle palladium catalyst and its preparation method and application | |
Deka et al. | Influence of Ni on enhanced catalytic activity of Cu/Co 3 O 4 towards reduction of nitroaromatic compounds: studies on the reduction kinetics | |
Wu et al. | Efficient palladium and ruthenium nanocatalysts stabilized by phosphine functionalized ionic liquid for selective hydrogenation | |
Gholinejad et al. | Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions | |
CN109876866A (en) | A kind of catalyst and preparation method thereof for aromatic aldehyde synthesis aromatic amine | |
Cheng et al. | Superfine CoNi alloy embedded in Al 2 O 3 nanosheets for efficient tandem catalytic reduction of nitroaromatic compounds by ammonia borane | |
Zhang et al. | Amine-functionalized MIL-53 (Al) with embedded ruthenium nanoparticles as a highly efficient catalyst for the hydrolytic dehydrogenation of ammonia borane | |
Ma et al. | Preparation of highly active heterogeneous Au@ Pd bimetallic catalyst using plant tannin grafted collagen fiber as the matrix | |
CN107029764B (en) | A kind of preparation method and application of support type P Modification palladium catalyst |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information |
Address after: 310014 Hangzhou city in the lower reaches of the city of Wang Chao Road, Zhejiang University of Technology,, Department of science and technology, 18 Applicant after: Zhejiang University of Technology Applicant after: Zhejiang Changshan Kerun new materials Co. Ltd. Address before: 310014 Hangzhou city in the lower reaches of the city of Wang Chao Road, Zhejiang University of Technology,, Department of science and technology, 18 Applicant before: Zhejiang University of Technology Applicant before: Zhejiang Changshan Kerun Chemicals Co., Ltd. |
|
CB02 | Change of applicant information | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CP01 | Change in the name or title of a patent holder |
Address after: 310014 Department of science and technology, Zhejiang University of Technology, No. 18 Chao Wang Road, Xiacheng District, Zhejiang, Hangzhou Co-patentee after: Li'an longkerun (Zhejiang) new material Co.,Ltd. Patentee after: ZHEJIANG University OF TECHNOLOGY Address before: 310014 Department of science and technology, Zhejiang University of Technology, No. 18 Chao Wang Road, Xiacheng District, Zhejiang, Hangzhou Co-patentee before: ZHEJIANG CHANGSHAN KERUN NEW MATERIAL Co.,Ltd. Patentee before: ZHEJIANG University OF TECHNOLOGY |
|
CP01 | Change in the name or title of a patent holder |