CN114656455B - Triazole modified ferric oxide photocatalyst and preparation method thereof - Google Patents
Triazole modified ferric oxide photocatalyst and preparation method thereof Download PDFInfo
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- CN114656455B CN114656455B CN202210567818.6A CN202210567818A CN114656455B CN 114656455 B CN114656455 B CN 114656455B CN 202210567818 A CN202210567818 A CN 202210567818A CN 114656455 B CN114656455 B CN 114656455B
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- -1 Triazole modified ferric oxide Chemical class 0.000 title claims abstract description 93
- 239000011941 photocatalyst Substances 0.000 title claims abstract description 78
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims abstract description 31
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000010525 oxidative degradation reaction Methods 0.000 claims abstract description 9
- 239000002957 persistent organic pollutant Substances 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 63
- 238000001035 drying Methods 0.000 claims description 44
- 239000007787 solid Substances 0.000 claims description 42
- 238000003756 stirring Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 15
- 229910021641 deionized water Inorganic materials 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- 239000002105 nanoparticle Substances 0.000 claims description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims description 8
- 238000005303 weighing Methods 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 7
- 239000012498 ultrapure water Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000009210 therapy by ultrasound Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001354 calcination Methods 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- 229910000859 α-Fe Inorganic materials 0.000 claims description 4
- WEBVDBDZSOJGPB-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-carbaldehyde Chemical compound O=CC1=CC=C2OCCC2=C1 WEBVDBDZSOJGPB-UHFFFAOYSA-N 0.000 claims description 3
- JAHIPDTWWVYVRV-UHFFFAOYSA-N 4-chloro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O JAHIPDTWWVYVRV-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- FTKASJMIPSSXBP-UHFFFAOYSA-N ethyl 2-nitroacetate Chemical compound CCOC(=O)C[N+]([O-])=O FTKASJMIPSSXBP-UHFFFAOYSA-N 0.000 claims description 3
- 238000012544 monitoring process Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000004809 thin layer chromatography Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001699 photocatalysis Effects 0.000 abstract description 16
- 230000015556 catabolic process Effects 0.000 abstract description 12
- 238000006731 degradation reaction Methods 0.000 abstract description 12
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 abstract description 12
- 229940012189 methyl orange Drugs 0.000 abstract description 12
- 230000007613 environmental effect Effects 0.000 abstract description 5
- 239000005416 organic matter Substances 0.000 abstract description 5
- 238000005286 illumination Methods 0.000 abstract description 3
- 238000011160 research Methods 0.000 abstract description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 12
- 238000002835 absorbance Methods 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 8
- 239000002351 wastewater Substances 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 7
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000013033 photocatalytic degradation reaction Methods 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 238000002336 sorption--desorption measurement Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 1
- IWAKWOFEHSYKSI-UHFFFAOYSA-N 1-chloro-2-methylbutane Chemical compound CCC(C)CCl IWAKWOFEHSYKSI-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- CXHHAWACKSPTFF-UHFFFAOYSA-N iodomethylcyclohexane Chemical compound ICC1CCCCC1 CXHHAWACKSPTFF-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000985 reflectance spectrum Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
-
- 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
- B01J35/39—Photocatalytic properties
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/30—Treatment of water, waste water, or sewage by irradiation
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/308—Dyes; Colorants; Fluorescent agents
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/30—Nature of the water, waste water, sewage or sludge to be treated from the textile industry
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2305/00—Use of specific compounds during water treatment
- C02F2305/08—Nanoparticles or nanotubes
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2305/00—Use of specific compounds during water treatment
- C02F2305/10—Photocatalysts
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- 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
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W10/00—Technologies for wastewater treatment
- Y02W10/30—Wastewater or sewage treatment systems using renewable energies
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Abstract
The invention provides a triazole modified ferric oxide photocatalyst and a preparation method thereof, belonging to the technical field of environmental management, wherein the triazole modified ferric oxide photocatalyst is obtained by modifying ferric oxide with a triazole compound; in addition, the invention also screens the photocatalytic activity of the triazole modified ferric oxide photocatalyst, and simultaneously researches the relation between the illumination time of the triazole modified ferric oxide photocatalyst and the degradation rate of methyl orange; the triazole modified ferric oxide photocatalyst prepared by the invention has high light utilization rate, photocatalytic activity and organic matter oxidative degradation capability, and can be used for oxidative degradation of organic pollutants in the technical field of environmental management.
Description
Technical Field
The invention relates to a triazole modified ferric oxide photocatalyst and a preparation method thereof, belonging to the technical field of environmental management.
Background
The waste water produced by processing cotton, hemp, fiber and blended products in a printing and dyeing mill is called printing and dyeing waste water, the concentration of organic matters in the printing and dyeing waste water is high, the chromaticity of the printing and dyeing waste water is large, and the printing and dyeing waste water has the characteristic of huge discharge because the printing and dyeing industry is a water consumption industry. The printing and dyeing wastewater not only pollutes the water environment, but also destroys the ecological balance of the water, poses threats to the survival of aquatic organisms, and simultaneously affects the safety of human drinking water sources, thereby becoming a difficult point or hot point for environmental management. The photocatalytic oxidation method uses a photocatalyst to absorb specific light to generate active oxygen to degrade pollutants in organic wastewater, is a deep oxidation technology, and has been applied to the degradation of various organic wastewater. Ferric oxide is a commonly used semiconductor photocatalyst, and has a narrow band gap width of 2.2 eV, but the low light utilization rate of sunlight leads to low photocatalytic activity and poor degradation efficiency of organic matters.
Disclosure of Invention
The invention solves the technical problem of low light utilization rate of the ferric oxide photocatalyst.
The invention provides a triazole modified ferric oxide photocatalyst and a preparation method thereof, which comprises the steps of sensitizing ferric oxide by synthesizing a substance triazole compound with optical activity, extending the excitation wavelength of ferric oxide, improving the light utilization rate and further improving the degradation rate of organic matters.
The triazole compound is characterized by having a chemical structural general formula shown as a formula I:
wherein: r 1 And R 2 Are all selected from alkyl, phenyl and benzyl with 2-10 carbon atoms.
The synthesis method of the triazole compound of the invention is shown as follows,
wherein, the specific synthetic route of A5 is as follows:
the specific experimental steps are as follows:
sequentially adding 2, 3-dihydrobenzofuran-5-formaldehyde, ethyl nitroacetate, sodium azide and DMSO (dimethyl sulfoxide) into a round-bottom flask, uniformly stirring, adding aluminum trichloride, carrying out water bath and stirring, monitoring the reaction by TLC (thin layer chromatography), adding deionized water and concentrated hydrochloric acid to inhibit AlCl after the reaction is completed 3 Extracting with ethyl acetate for 3 times, mixing organic layers, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing ethyl acetate under reduced pressure, purifying with column, and drying to obtain A2 solid.
Sequentially adding A2 solid and acetonitrile into a three-neck flask, stirring, adding potassium carbonate, dropwise adding a halogenated compound, water bathing, cooling, filtering, desolventizing, purifying by column chromatography, and drying to obtain A3 solid, wherein the halogenated compound has a general formula R 1 X。
Preferably, R 1 R in X 1 Selected from alkyl with 2-10 carbon atoms, phenyl and benzyl, X is selected from fluorine, chlorine, bromine,Iodine.
Adding methanol, THF and deionized water into a round-bottom flask, stirring, adding A3 and sodium hydroxide, stirring at room temperature, removing solvent under reduced pressure, adding dichloromethane for dissolving, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing solvent under reduced pressure, purifying and drying by column chromatography to obtain A4 solid.
Preferably, the mass of the sodium hydroxide is 1.1 times that of A3.
Adding A4 solid, toluene and thionyl chloride into a three-necked flask, heating and refluxing, cooling, desolventizing and drying to obtain A5 solid.
In addition, the specific synthetic route of B4 is as follows:
the specific experimental steps are as follows:
adding 4-chloro-2-nitrobenzoic acid and acetic acid into a three-neck flask, heating, adding iron powder for three times, carrying out water bath reaction, filtering while hot, neutralizing a solution system with saturated sodium carbonate solution, extracting for 3 times with ethyl acetate, combining an organic layer, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing ethyl acetate under reduced pressure, and drying to obtain a B2 solid.
Adding liquid phosgene, THF and pyridine into a round-bottom flask, dropwise adding a THF solution containing B2, introducing nitrogen to remove phosgene after reaction, removing THF under reduced pressure, heating and refluxing ethyl acetate, cooling, desolventizing and drying to obtain a B3 solid.
Adding B3 solid and ethyl acetate into a three-necked flask, dripping acetic acid, stirring, dripping a primary amine compound for reaction, adding deionized water, stirring, separating liquid, washing with deionized water for 3 times, combining organic layers, drying with anhydrous sodium sulfate, and desolventizing to obtain B4 solid, wherein the primary amine compound has R 2 NH 2 General formula (VII).
Preferably, said R 2 NH 2 In R 2 Selected from alkyl of 2-10 carbon atoms, phenyl and benzyl.
The specific experimental steps for synthesizing the triazole compound from A5 and B4 are as follows:
adding A5 solid, dichloromethane and B4 solid into a three-necked flask, dropwise adding Triethylamine (TEA), stirring, adding deionized water, adjusting the pH of a solution system to about 9.5 by using a sodium hydroxide solution, extracting for 3 times by using ethyl acetate, merging an organic layer, washing by using saturated sodium chloride, drying by using anhydrous sodium sulfate, decompressing, removing the solvent, and drying to obtain a triazole compound (C), wherein the structural formula of the triazole compound is shown as a formula I.
In addition, the experimental steps for synthesizing the triazole modified ferric oxide photocatalyst are as follows:
adding urea aqueous solution into a high-pressure reaction kettle, putting a polytetrafluoroethylene gasket, adding normal butanol solution containing ferric nitrate into a weighing bottle, putting the weighing bottle on the gasket, carrying out oven reaction, cooling, alternately cleaning absolute ethyl alcohol and ultrapure water, centrifuging, drying in an oven, and calcining in a muffle furnace to obtain the ferric oxide nano particles (alpha-Fe) 2 O 3 ）。
Adding the triazole compound (C) into absolute ethyl alcohol, stirring and carrying out ultrasonic treatment to obtain a triazole compound (C) dispersion liquid; adding ferric oxide nano particles into absolute ethyl alcohol, stirring and carrying out ultrasonic treatment to obtain ferric oxide nano particle dispersion liquid. And dripping the triazole compound (C) dispersion liquid into the ferric oxide nano particle dispersion liquid, stirring in a water bath until the ferric oxide nano particle dispersion liquid is evaporated to dryness, washing twice with ultrapure water, and drying in a drying oven to obtain the triazole modified ferric oxide photocatalyst (T).
Preferably, the mass ratio of the triazole compound (C) to the ferric oxide nanoparticles is 3: 5.
The invention has the beneficial effects that:
according to the invention, the triazole modified ferric oxide photocatalyst is synthesized, the photocatalytic activity screening is carried out, the relation research of the illumination time and the methyl orange degradation rate of the triazole modified ferric oxide photocatalyst is carried out, and the result shows that the light utilization rate, the photocatalytic activity and the organic matter oxidative degradation capability of the triazole modified ferric oxide photocatalyst are high, and the methyl orange degradation rate and the illumination time of the triazole modified ferric oxide photocatalyst are positively correlated, so that the triazole modified ferric oxide photocatalyst can be used for oxidative degradation of organic pollutants in the technical field of environmental management.
Drawings
FIG. 1 is a UV-VIS diffuse reflectance spectrum of example 13.
FIG. 2 is a statistical line graph of the degradation rate of methyl orange of example 14.
FIG. 3 is a hydrogen spectrum of sample C11, wherein the solvent is CDCl3 [ 10-11 ppm: CONH; 7-8.2 ppm: Ar-H; 2.9 to 3ppm, 4.25 to 4.28 ppm: OCH2CH 2; 4.98 ppm: N-H-Ar ].
Detailed Description
The synthesis and photocatalytic activity of the triazole modified ferric oxide photocatalyst are more specifically illustrated by specific preparation and photocatalytic activity measurement examples, which are only used for specifically illustrating the invention and not limiting the invention, especially the photocatalytic activity is only illustrated and not limiting the invention, and the specific implementation modes are as follows:
the following examples are provided to illustrate the present invention in detail, but they should not be construed as limiting the scope of the present invention.
Example 1
(1) adding 7.41 g of 2, 3-dihydrobenzofuran-5-formaldehyde, 9.98 g of ethyl nitroacetate, 1.95 g of sodium azide and 150 mL of DMSO into a round bottom flask in sequence, stirring uniformly, adding 0.67 g of aluminum trichloride, carrying out water bath at 70 ℃ and stirring, monitoring the reaction by TLC, adding 80 mL of deionized water and 3 drops of concentrated hydrochloric acid to inhibit AlCl after the reaction is completed 3 The hydrolysis is carried out, 50 mL of ethyl acetate is used for extraction for 3 times, organic layers are combined, saturated sodium chloride is used for washing, anhydrous sodium sulfate is used for drying, ethyl acetate is removed under reduced pressure, and column chromatography purification and drying are carried out, so that A2 solid is obtained.
(2) In a three-necked flask, 10.74 g of 10.74 g A2 solid and 50 mL of acetonitrile were sequentially added and stirred, 5.80 g (0.042 mol) of potassium carbonate was added, and 5.72 g of bromoethane (R) was added dropwise 1 X), water bath at 60 ℃ for 12 h, cooling, filtering and desolventizing,purifying by column chromatography and drying to obtain A3 solid.
(3) Adding 30 mL of methanol, 30 mL of THF and 30 mL of deionized water into a round-bottom flask, stirring, adding 10 g A3 and 11 g of sodium hydroxide, stirring at room temperature for 5 hours, decompressing to remove the solvent, adding 40 mL of dichloromethane to dissolve, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, decompressing to remove the solvent, purifying and drying by passing through a column to obtain the A4 solid.
(4) Adding 5 g A4 solid, 100 mL toluene and 20 mL thionyl chloride into a three-neck flask, heating and refluxing for 8 h, cooling, desolventizing and drying to obtain A5 solid.
(5) Adding 6.04 g (0.03 mol) of 4-chloro-2-nitrobenzoic acid and 70 mL of acetic acid into a three-neck flask, heating to 50 ℃, adding 5 g of iron powder for three times, reacting in a water bath at 65 ℃ for 4 hours, filtering while hot, neutralizing a solution system with a saturated sodium carbonate solution, extracting with 50 mL of ethyl acetate for 3 times, merging an organic layer, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing ethyl acetate under reduced pressure, and drying to obtain a B2 solid.
(6) Adding 6 g of liquid phosgene, 50 mL of THF and 2 drops of pyridine into a round-bottom flask, dropwise adding 50 mL of THF solution containing 4 g B2 at 28 ℃, reacting for 6 h, introducing nitrogen for 1.5 h to remove phosgene, removing THF under reduced pressure, heating and refluxing for 2 h by 200 mL of ethyl acetate, cooling, desolventizing and drying to obtain B3 solid.
(7) In a three-necked flask, 3.5 g B3 solid and 100 mL of ethyl acetate were added dropwise, and 2.3 g of acetic acid, stirring at 37 ℃ for 2 hours, and 2 g of ethylamine (R) 2 NH 2 ) And reacting for 4 h, then adding 100 mL of deionized water, stirring and separating liquid, washing for 3 times by using 100 mL of deionized water, combining organic layers, drying by using anhydrous sodium sulfate, and desolventizing to obtain B4 solid.
(8) Adding 3 g A5 solid, 100 mL of dichloromethane and 2.7 g B4 solid into a three-neck flask, dropwise adding 1.5 g of Triethylamine (TEA), stirring for 1.5 h, adding 100 mL of deionized water, adjusting the solution system to pH about 9.5 by 10% sodium hydroxide solution, extracting for 3 times by 40 mL of ethyl acetate, merging an organic layer, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, decompressing, removing the solvent, and drying to obtain the triazole compound C1.
(9) Adding 11 mL of 0.4 mol/L urea aqueous solution into a high-pressure reaction kettle, placing a polytetrafluoroethylene gasket, adding 8 mL of n-butyl alcohol solution containing 1.2 g of ferric nitrate into a 10 mL weighing bottle, placing the weighing bottle on the gasket, carrying out oven reaction at 140 ℃ for 6 h, cooling, alternately cleaning with absolute ethyl alcohol and ultrapure water for 3 times, centrifuging, drying in an oven at 80 ℃, and calcining in a muffle furnace at 400 ℃ for 2 h to obtain the ferric oxide nanoparticles.
(10) Adding 0.3 g of triazole compound C1 into 10 mL of absolute ethyl alcohol, stirring for 15 min, and performing ultrasonic treatment for 15 min to obtain a triazole compound C1 dispersion liquid; adding 0.5 g of ferric oxide nanoparticles into 10 mL of absolute ethanol, stirring for 15 min, and performing ultrasonic treatment for 15 min to obtain ferric oxide nanoparticle dispersion liquid. Dripping the triazole compound C1 dispersion liquid into the ferric oxide nanoparticle dispersion liquid, stirring in a water bath at 80 ℃ until the ferric oxide nanoparticle dispersion liquid is dried by distillation, washing twice with 20 mL of ultrapure water, and drying in an oven at 80 ℃ to obtain the triazole modified ferric oxide photocatalyst T1.
Example 2
replacement of bromoethane (R) in example 1 (2) with 1-chloroisobutane 1 X) to synthesize triazole compound C2 modified triazole modified ferric oxide photocatalyst T2.
Example 3
1-chloro-2-methylbutane was used in place of ethyl bromide (R) in example 1 (2) 1 X) to synthesize triazole compound C3 modified triazole modified ferric oxide photocatalyst T3.
Example 4
bromocyclohexane was used in place of bromoethane (R) in example 1 (2) 1 X) to synthesize triazole compound C4 modified triazole modified ferric oxide photocatalyst T4.
Example 5
(iodomethyl) cyclohexane was used in place of bromoethane (R) in example 1 (2) 1 X) to synthesize triazole compound C5 modified triazole modified ferric oxide photocatalyst T5.
Example 6
bromoethane (R) from example 1 (2) was replaced by bromobenzene 1 X) to synthesize triazole compound C6 modified triazole modified ferric oxide photocatalyst T6.
Example 7
bromotoluene was used in place of bromoethane (R) in example 1 (2) 1 X) to synthesize triazole compound C7 modified triazole modified ferric oxide photocatalyst T7.
Example 8
bromotoluene was used in place of bromoethane (R) in example 1 (2) 1 X) isopropylamine was used instead of ethylamine (R) in example 1 (7) 2 NH 2 ) Synthesizing triazole compound C8 modified triazole modified ferric oxide photocatalyst T8.
Example 9
bromotoluene was substituted for bromoethane (R) in example 1 (2) 1 X) replacement of ethylamine (R) from example 1 (7) with tert-butylamine 2 NH 2 ) Synthesizing triazole compound C9 modified triazole modified ferric oxide photocatalyst T9.
Example 10
bromotoluene was substituted for bromoethane (R) in example 1 (2) 1 X) cyclohexylamine is used instead of ethylamine (R) in example 1 (7) 2 NH 2 ) Synthesizing triazole compound C10 modified triazole modified ferric oxide photocatalyst T10.
Example 11
bromotoluene was substituted for bromoethane (R) in example 1 (2) 1 X) Aniline instead of ethylamine (R) in example 1 (7) 2 NH 2 ) Synthesizing triazole compound C11 modified triazole modified ferric oxide photocatalyst T11.
Example 12
bromotoluene was substituted for bromoethane (R) in example 1 (2) 1 X) benzylamine instead of ethylamine (R) in example 1 (7) 2 NH 2 ) Synthesizing triazole compound C12 modified triazole modified ferric oxide photocatalyst T12.
Comparative example 1 Synthesis of iron sesquioxide photocatalyst
Adding 11 mL of 0.4 mol/L urea aqueous solution into a high-pressure reaction kettle, placing a polytetrafluoroethylene gasket, adding 8 mL of n-butyl alcohol solution containing 1.2 g of ferric nitrate into a 10 mL weighing bottle, placing the weighing bottle on the gasket, carrying out oven reaction at 140 ℃ for 6 h, cooling, alternately cleaning with absolute ethyl alcohol and ultrapure water for 3 times, centrifuging, drying in an oven at 80 ℃, and calcining in a muffle furnace at 400 ℃ for 2 h to obtain the ferric oxide photocatalyst.
Example 13 determination of photocatalytic Activity
(1) Measurement method
Adding 50 mL of 12 mg/mL methyl orange solution into a beaker, adding 300 mg of a photocatalyst to be tested, taking the ferric oxide photocatalyst prepared in comparative example 1 as a negative control, taking the photocatalyst to be tested as the triazole modified ferric oxide photocatalyst T1-T12 prepared in examples 1-12, adding 0.3 mL of hydrogen peroxide, and oscillating on a multi-purpose oscillator for 30 min to form suspension so as to achieve adsorption/desorption balance. The sun was irradiated for 30 min, sampled, centrifuged, and the absorbance was measured with an ultraviolet-visible spectrophotometer and the experiment was repeated 3 times. The blank control was a methyl orange solution without any photocatalyst added.
Methyl orange photocatalytic degradation rate (%) = (absorbance of blank control-absorbance of experimental group)/absorbance of blank control × 100%.
(2) Results of the experiment
The photocatalytic activity results of the photocatalyst of the present invention are shown in table 1.
TABLE 1 photocatalytic activity of the inventive photocatalyst for oxidative degradation of methyl orange
| Photocatalyst and process for producing the same | Methyl orange degradation rate (%) | Photocatalyst and process for producing the same | Methyl orange degradation rate (%) |
| Ferric oxide photocatalyst | 30.28±0.78 | — | — |
| T1 | 78.54±1.15 | T7 | 81.83±1.98 |
| T2 | 77.82±1.32 | T8 | 82.74±2.61 |
| T3 | 88.41±1.58 | T9 | 85.77±2.36 |
| T4 | 86.89±2.35 | T10 | 86.85±2.46 |
| T5 | 85.76±2.84 | T11 | 98.56±1.71 |
| T6 | 90.21±2.31 | T12 | 88.76±2.43 |
From table 1, it can be seen that the methyl orange degradation rate of the triazole modified ferric oxide photocatalyst prepared by the invention is greater than that of the ferric oxide photocatalyst, and that the light utilization rate, the photocatalytic activity and the organic matter oxidative degradation capability of the triazole modified ferric oxide photocatalyst are greater than that of TiO 2 A photocatalyst; as can be seen from the ultraviolet-visible diffuse reflection spectra of the triazole modified ferric oxide photocatalyst T11 and ferric oxide shown in fig. 1, the triazole compound with photoactivity synthesized by the present invention has the advantages that the excitation wavelength range of ferric oxide is extended by sensitizing ferric oxide, the wavelength is red-shifted, and the light utilization rate of ferric oxide is improved, so that both the photocatalytic activity and the organic matter oxidative degradation capability of the triazole modified ferric oxide photocatalyst are greater than those of TiO 2 A photocatalyst.
Example 14 determination of photocatalytic Activity of triazole-modified ferric oxide photocatalyst T11 of the present invention
(1) Measurement method
50 mL of 12 mg/mL methyl orange solution was added to the beaker, 300 mg of triazole-modified ferric oxide photocatalyst T11 was added, the ferric oxide photocatalyst prepared in example 13 was used as a negative control, 0.3 mL of hydrogen peroxide was added, and the mixture was shaken on a multi-purpose shaker for 30 min to form a suspension, which reached equilibrium of adsorption/desorption. The sunlight is irradiated for 5, 10, 15, 20, 25 and 30 min respectively, sampling and centrifuging are carried out, the absorbance is measured by an ultraviolet-visible spectrophotometer, and the experiment is repeated for 3 times. The blank control was a methyl orange solution without any photocatalyst added.
Methyl orange photocatalytic degradation rate (%) = (absorbance of blank control-absorbance of experimental group)/absorbance of blank control × 100%.
(2) Results of the experiment
As shown in fig. 2, as the sunlight irradiation time increases, the methyl orange degradation rate of triazole modified ferric oxide photocatalyst T11 increases, and is in positive correlation with the sunlight irradiation time, and is greater than the methyl orange degradation rate of ferric oxide photocatalyst, which indicates that the light utilization rate, the photocatalytic activity and the organic matter oxidative degradation capability of triazole modified ferric oxide photocatalyst are greater than that of ferric oxide photocatalyst.
Claims (5)
1. The triazole compound is characterized by having a chemical structural general formula shown as a formula I:
wherein: r 1 One selected from ethyl, isopropyl, cyclohexane methyl, phenyl and benzyl; r 2 Is selected from one of ethyl, isopropyl, tertiary butyl, cyclohexane, phenyl and benzyl.
2. The preparation method of the triazole modified ferric oxide photocatalyst is characterized by comprising the following preparation steps:
(1) sequentially adding 2, 3-dihydrobenzofuran-5-formaldehyde, ethyl nitroacetate, sodium azide and DMSO (dimethyl sulfoxide) into a round-bottom flask, uniformly stirring, adding aluminum trichloride, carrying out water bath and stirring, monitoring the reaction by TLC (thin layer chromatography), adding deionized water and concentrated hydrochloric acid to inhibit AlCl after the reaction is completed 3 Extracting with ethyl acetate for 3 times, mixing organic layers, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing ethyl acetate under reduced pressure, purifying with column, and drying to obtain A2 solid with the following structure:
(2) adding A2 solid and acetonitrile in sequence into a three-neck flask, stirring, adding potassium carbonate, dropwise adding a halogenated compound, performing water bath, cooling, filtering, desolventizing, and purifying and drying by column chromatography to obtain A3 solid with the following structure:
the halogenated compound has the general formula R 1 X；
(3) Adding methanol, THF and deionized water into a round-bottom flask, stirring, adding A3 solid and sodium hydroxide, stirring at room temperature, removing solvent under reduced pressure, adding dichloromethane for dissolving, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing solvent under reduced pressure, purifying and drying by column chromatography to obtain A4 solid with the following structure:
(4) adding A4 solid, toluene and thionyl chloride into a three-neck flask, heating and refluxing, cooling, desolventizing and drying to obtain A5 solid, which has the following structure:
(5) adding 4-chloro-2-nitrobenzoic acid and acetic acid into a three-neck flask, heating, adding iron powder for three times, carrying out water bath reaction, filtering while hot, neutralizing a solution system with saturated sodium carbonate solution, extracting for 3 times with ethyl acetate, combining an organic layer, washing with saturated sodium chloride, drying with anhydrous sodium sulfate, removing ethyl acetate under reduced pressure, and drying to obtain a B2 solid, wherein the solid has the following structure:
(6) adding liquid phosgene, THF and pyridine into a round-bottom flask, dropwise adding a THF solution containing B2 solid, introducing nitrogen to remove phosgene after reaction, removing THF under reduced pressure, heating ethyl acetate to reflux, cooling to remove solvent and drying to obtain B3 solid, wherein the B3 solid has the following structure:
(7) adding B3 solid and ethyl acetate into a three-necked flask, dripping acetic acid, stirring, dripping a primary amine compound, reacting, adding deionized water, stirring, separating liquid, washing with deionized water for 3 times, combining organic layers, drying with anhydrous sodium sulfate, and desolventizing to obtain B4 solid, wherein the solid has the following structure:
the primary amine compound has R 2 NH 2 General formula (VII);
(8) adding A5 solid, dichloromethane and B4 solid into a three-necked flask, dropwise adding triethylamine, stirring, adding deionized water, adjusting the pH of a solution system to about 9.5 by using a sodium hydroxide solution, extracting by using ethyl acetate for 3 times, merging an organic layer, washing by using saturated sodium chloride, drying by using anhydrous sodium sulfate, decompressing, dissolving and drying to obtain a triazole compound;
(9) adding a urea aqueous solution into a high-pressure reaction kettle, putting a polytetrafluoroethylene gasket, adding a normal butanol solution containing ferric nitrate into a weighing bottle, putting the weighing bottle on the gasket, carrying out oven reaction, cooling, alternately cleaning absolute ethyl alcohol and ultrapure water, centrifuging, drying in an oven, and calcining in a muffle furnace to obtain ferric oxide nanoparticles;
(10) adding a triazole compound into absolute ethyl alcohol, stirring and carrying out ultrasonic treatment to obtain a triazole compound dispersion liquid; adding alpha-Fe into absolute ethyl alcohol 2 O 3 Stirring and ultrasonic treating to obtain alpha-Fe 2 O 3 A dispersion liquid; dripping the triazole compound dispersion liquid into alpha-Fe 2 O 3 Stirring in a water bath until the dispersion liquid is evaporated to dryness, washing with ultrapure water twice, and drying in an oven to obtain the triazole modified ferric oxide photocatalyst;
the R is 1 R in X 1 Selected from alkyl, phenyl and benzyl with 2-10 carbon atoms, and X is selected from fluorine, chlorine, bromine and iodine;
the R is 2 NH 2 In R 2 Selected from alkyl of 2-10 carbon atoms, phenyl and benzyl.
3. The preparation method of the triazole modified ferric oxide photocatalyst according to claim 2, wherein the mass of the sodium hydroxide in the step (3) is 1.1 times that of the A3 solid.
4. The preparation method of the triazole modified ferric oxide photocatalyst according to claim 2, wherein the mass ratio of the triazole compound to the ferric oxide nanoparticles in the step (10) is 3: 5.
5. The application of the triazole modified ferric oxide photocatalyst obtained by the preparation method of any one of claims 2 to 4 is characterized in that the triazole modified ferric oxide photocatalyst is used as a photocatalyst for oxidative degradation of organic pollutants.
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