CN115624957B - Modified functional silica gel material and preparation method and application thereof - Google Patents
Modified functional silica gel material and preparation method and application thereof Download PDFInfo
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- CN115624957B CN115624957B CN202211553724.XA CN202211553724A CN115624957B CN 115624957 B CN115624957 B CN 115624957B CN 202211553724 A CN202211553724 A CN 202211553724A CN 115624957 B CN115624957 B CN 115624957B
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- silica gel
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000000741 silica gel Substances 0.000 title claims abstract description 41
- 229910002027 silica gel Inorganic materials 0.000 title claims abstract description 41
- 239000000463 material Substances 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 19
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 150000002739 metals Chemical class 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003463 adsorbent Substances 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- -1 aromatics Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000012501 chromatography medium Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 239000010970 precious metal Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004115 Sodium Silicate Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052911 sodium silicate Inorganic materials 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 7
- 238000011068 loading method Methods 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 8
- 239000010949 copper Substances 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
- 229960005305 adenosine Drugs 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
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 2
- 229940045145 uridine Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UGHWFYKQWZHCHK-UHFFFAOYSA-N 2-(chloromethyl)-1h-imidazole Chemical compound ClCC1=NC=CN1 UGHWFYKQWZHCHK-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 1
- MPDNOXDKZZVEKF-UHFFFAOYSA-N 3-(3-chloropropylsulfanyl)propyl-trimethoxysilane Chemical compound ClCCCSCCC[Si](OC)(OC)OC MPDNOXDKZZVEKF-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- IPKKDQOUBFUVGT-UHFFFAOYSA-N 5-(chloromethyl)-1h-pyrazole;hydrochloride Chemical compound Cl.ClCC=1C=CNN=1 IPKKDQOUBFUVGT-UHFFFAOYSA-N 0.000 description 1
- ARUYSNCZGGNUCN-UHFFFAOYSA-N 6-(chloromethyl)imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC(CCl)=CN21 ARUYSNCZGGNUCN-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 description 1
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 229960000306 zinc gluconate Drugs 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
-
- 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
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
-
- 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
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
Abstract
The invention discloses a modified functional silica gel material and a preparation method and application thereof; the modified functional silica gel material is obtained by reacting a multifunctional amino functional silica gel material with an aromatic heterocyclic compound or a derivative thereof; the modified functional silica gel material has good chelating capacity with metal ions, good selectivity to polar components, high loading rate, high adsorption capacity and good adsorption effect.
Description
Technical Field
The invention belongs to the technical field of material synthesis, and particularly relates to a modified functional silica gel material, and a preparation method and application thereof.
Background
The technological development of many different industries and market applications has gradually increased the demand for chemical purity, which is precisely the cornerstone of these technologies. For example, the pharmaceutical and biotechnological industries must control organic and inorganic impurities to lower levels as much as possible, while the metal residues (e.g., ca, zn, mg) common in electronic chemicals must be below 0.1ppm.
The increasing social and legislative pressures for environmental protection have led to a further increasing demand for cleaning processes and efforts to avoid or reduce the production of waste, especially the residual amounts of toxic metals and compounds in the environment.
Precious metals (including platinum, rhodium, palladium, ruthenium, iridium, and gold) are widely used in many different applications in different industries, and are a limited resource. In the smelting and purification processes of the mining industry, very low concentrations of high value metals (e.g., precious metals) often coexist with other metals, which in some cases are very high. To avoid the loss of high value metals in large quantities, a better technique is needed to achieve: a) Reducing the desired metal to very low residual concentrations; b) The high-efficiency action is carried out on the extremely low ppm metal concentration; c) Selectively acting only on high value metals in the presence of higher concentrations of other metals.
The aromatic heterocyclic ring and the derivative thereof are good electron donors, are one of common and important ligands of metal ion complexes, have good adsorption effect on metal ions, particularly divalent metal ions, and can be used for separating noble metals if the aromatic heterocyclic ring and the derivative thereof are loaded on an inorganic carrier. In addition, the nanometer composite material has good selectivity to polar components and strong retention capacity, is loaded on an inorganic carrier, and can be used as a chromatography medium for purification and separation of metals, metal complexes, organic compounds and biological compounds or used for solid phase extraction.
At present, there are few reports about aromatic heterocycles and derivatives thereof loaded on inorganic carriers, and the loading rate is not high due to poor planar structure and poor framework flexibility, if any.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a modified functional silica gel material, and a preparation method and application thereof. The modified functional silica gel material is prepared by introducing aromatic heterocyclic compounds or derivatives thereof into a multifunctional amino functional silica gel material serving as a carrier, has good chelating capacity with metal ions, has good selectivity on polar components, and is high in loading rate, high in adsorption capacity and good in adsorption effect.
In order to achieve the technical purpose and achieve the technical effect, the invention is realized by the following technical scheme:
a modified functional silica gel material is a compound shown in a structural formula I;
the compound shown in the structural formula I is obtained by reacting a compound shown in a structural formula II with an aromatic heterocyclic compound or a derivative thereof;
structural formula II is:
B、B 0 Each is H or another polyamine
But B, B 0 Not both can be H; v is a substituent group and is selected from C 1-22 Alkyl radical, C 2-22 Alkenyl or C 1-22 An alkylaryl group; w is a substituent and is selected from C 1-20 Mercaptoalkyl radical, C 2-20 Alkyl sulfide group, C 1-22 Alkylthiothioalkyl or C 2-20 Alkylene thioether alkyl, C 2-20 Alkyl thioether aryl, C 2-20 Alkylene thioether aryl or C 2-6 Alkyl group SC 2-6 Alkyl NHC (= S) NHR 1 (ii) a By silicon atoms, hydrogen, straight or branched C, of other groups in formula II 1-22 Alkyl, terminal group (R) 2 ) 3 SiO 1/2 Crosslinking agent or chain R 2 q Si(OR 3 ) g O k/2 Or one or more of the silicon atoms of the other groups in formula II saturate the free valences of the silicate oxygen atoms; r 1-3 Are independently selected from straight chain or branched chain C 1-12 Alkyl, aryl and C 1-22 An alkylaryl group; k is an integer from 1 to 3; q is an integer from 1 to 2; g is an integer from 0 to 2, and satisfies g + k + q =4; m is an integer from 2 to 12; p is an integer from 2 to 99; t is an integer from 1 to 49; a. b, c, d, e are integers, and [ a + b ]]C is in the range of 0.00001 to 100000; a. c are all always present; when b, d or e is greater than 0, the ratio of d + e to a + b + c is between 0.00001 and 100000;
the structural formula I is:
wherein Z is 1 Is thatOr->,B 1 、B 2 Is Y or->But B is 1 、B 2 Not both can be Y; y is one of the following structural formulas:
wherein the variable group on the structural formula is R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 (ii) a In the above formula, at least one of the variable groups is-CH 2 -or-CH = CCH 2 -, the other variable groups in the structural formula are respectively and independently selected from H and C 1-3 Alkyl radical, C 2-6 Alkenyl radical, C 3-6 Alkynyl, aryl, C 1-6 Alkylaryl, cl, br, I or-NO 2 。
Further, p is an integer from 2 to 30; the t is an integer of 1 to 14.
The invention further provides a preparation method of the modified functional silica gel material, which comprises the following steps:
1) Will (R) 3 O) 3 Si(CH 2 ) m S(CH 2 ) 3 X 1 With the corresponding amine NH 2 [C 2 H 4 NH] p Reaction of H to silane (R) 3 O) 3 Si(CH 2 ) m S(CH 2 ) 3 NH[C 2 H 4 NH] p H,X 1 Is a halide;
2) Reacting the silane obtained in step 1) with 1, 2-dichloroethane and an amine NH 2 [C 2 H 4 NH] p H, reacting the mixture;
3) Adding silane VSi (OR) to the reactant of the step 1) OR the step 2) as required 3 ) 3 and/OR WSi (OR) 3 ) 3 Then grafted onto silica gel, either in a solvent or with sodium silicate or tetraalkyl [ C ] 1-6 ]Carrying out sol-gel reaction on orthosilicate to obtain a compound shown as a structural formula II; wherein the solvent includes, but is not limited to, hydrocarbons, aromatics, alcohols, or water;
4) Mixing a compound shown in a structural formula II and an aromatic heterocyclic compound or a derivative thereof in a solvent, stirring and reacting for a certain time at a certain temperature, filtering, washing and drying to obtain a compound shown in a structural formula I;
wherein, the aromatic heterocyclic compound or the derivative thereof is YX, X is Cl, br or I, and Y is selected from one of the following structural formulas:
wherein the variable group on the structural formula is R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 (ii) a In the above formula, at least one of the variable groups is-CH 2 -or-CH = CCH 2 -, the other variable groups in the structural formula are independently selected from H and C 1-3 Alkyl radical, C 2-6 Alkenyl radical, C 3-6 Alkynyl, aryl, C 1-6 Alkylaryl, cl, br, I or-NO 2 。
In the preparation method, the reaction temperature of the step 1) is 20-160 ℃, the reaction time is 0.5-24h, (R) 3 O) 3 Si(CH 2 ) m S(CH 2 ) 3 X 1 With amines NH 2 [C 2 H 4 NH] p The molar ratio of H is 1:1.5 to 6, X 1 Preferably chlorine or bromine.
In the preparation method, the reaction temperature of the step 2) is 20-160 ℃, and the reaction time is 0.5-24h.
In the preparation method, the silica gel grafting reaction temperature in the step 3) is 20-160 ℃, and the reaction time is 0.5-24h; among them, typical solvents include toluene, xylene, heptane, ethanol and methanol; at the end of the reaction, the composition is separated by filtration or centrifugation, then washed thoroughly to remove any residual reactants, and finally dried. The silica gel grafting reaction process can be widely applied to commercially available silica gel (amorphous or spherical silica gel, preferably spherical silica gel); silica gel particle size ranges from the nanoparticle grade to 5 to 30 millimeters; and the silica gel has a widely distributed known pore size, preferably a pore diameter between 40 and 250 a. The sol-gel reaction is carried out in a solvent under an acidic or basic catalyst, the reaction temperature is 20-160 ℃, the reaction time is 0.5-48 hours, and after the reaction is finished, the solid is ground, washed to remove any residual reactant and dried. Typical acids and bases used in the sol-gel reaction process are hydrochloric acid and aqueous ammonia, respectively, but are not limited thereto, and solvents used include, but are not limited to, methanol, ethanol, and water, and mixtures thereof.
Further, the solvent in step 4) is preferably at least one of methanol, dimethyl sulfoxide, dichloromethane, acetonitrile, chloroform and N, N-dimethylformamide; the organic solvent is preferably at least one of methanol, dimethyl sulfoxide, dichloromethane, acetonitrile, chloroform and N, N-dimethylformamide.
Further, in the step (4), the ratio of the mass gram of the compound represented by the structural formula II to the amount of the substance of the heteroaromatic compound or a derivative thereof is 1.
Further, in the step (4), a certain amount of alkali solution can be added for reaction; the alkali solution is preferably at least one of triethylamine, saturated sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate and sodium hydroxide solution.
Further, the reaction temperature in the step (4) is 30 to 150 ℃, and the reaction time is 0.5 to 12h.
The invention further provides an application of the modified functional silica gel material, and specifically, the compound shown in the structural formula I can be used as an adsorbent for adsorbing metal ions.
Furthermore, the compound shown in the structural formula I is used as an adsorbent for removing impurities of electronic chemicals, removing impurities of medicines and intermediate metals, recovering precious metals and removing heavy metals.
The invention further provides another application of the modified functional silica gel material, and particularly relates to a compound shown in a structural formula I as an adsorbent, which can be used as a chromatography medium or a solid phase extraction material.
Furthermore, the compounds of formula I are useful as adsorbents, as chromatographic media for the purification and separation of metals, metal complexes, organic compounds or biological compounds, or as solid phase extraction materials.
The invention has the beneficial effects that:
the invention takes a multifunctional amino-functional silica gel material shown in a structural formula II as a carrier, and utilizes a plurality of amino groups contained in the carrier and-CH contained in an aromatic heterocyclic compound or a derivative thereof 2 X or-CH = CCH 2 The X group reacts, so that a plurality of aromatic heterocyclic compounds or derivatives thereof are introduced, and the load rate of the aromatic heterocyclic compounds or the derivatives thereof is greatly improved. Moreover, the aromatic heterocyclic ring or the derivative thereof has very good chelating capacity for metal ions, especially divalent metal ions due to the plane structure and steric hindrance; the modified functional silica gel material loaded with the aromatic heterocyclic compound or the derivative thereof can effectively and selectively adsorb metal ions. In addition, the modified functional silica gel material loaded with the aromatic heterocyclic compound or the derivative thereof has good selectivity on polar components and strong retention capacity, and can be used as a chromatography medium for purification and separation of metals, metal complexes, organic compounds or biological compounds or a solid phase extraction material.
The modified functional silica gel material greatly improves the loading rate of the aromatic heterocyclic compound or the derivative thereof, improves the adsorption capacity and the adsorption effect, and can solve the problems that the aromatic heterocyclic compound and the derivative thereof are difficult to load on an inorganic carrier and the loading rate is low in the prior art.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to specific embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparing a multifunctional amino-functionalized silica gel represented by structural formula II: adding polyethylene polyamine (0.4 mol) and 3- (3-chloropropyl) thiopropyl trimethoxy silane (0.4 mol) into a 500mL three-neck flask provided with a glass plug and a condensation reflux device, refluxing for 2.5h at 150 ℃, cooling to 70 ℃, adding methanol (40 mL), refluxing for 1h, cooling, adding the reacted substance and 3-mercaptopropyl trimethoxy silane (0.2 mol) into a mixed solution of xylene (125 mL) and spherical silica gel (90g, 200-500 mu m), refluxing for 7h at 150 ℃, cooling, filtering, washing with ethanol for 5 times and drying to obtain the compound shown in the structural formula II, wherein m is 3, p is 9, W is 3-mercaptopropyl, a, c and e exist, and b and d are all zero.
Example 1-1
10g of the compound represented by the structural formula II in example 1 was accurately weighed, 100ml of methanol solution was added, then 2-chloromethylimidazole (3.5 g, 0.03mol) and 5.5ml of triethylamine were added, stirred and refluxed at 120 ℃ for 4 hours, cooled, filtered, washed with deionized water for 5 times, and dried to obtain the compound represented by the structural formula I.
Examples 1 to 2
10g of the compound of the formula II prepared in example 1 were weighed out accurately, 90ml of dichloromethane solution were added, followed by 2-chloromethylpyridine (10.2 g, 0.08mol) and 10ml of triethylamine, stirred at 30 ℃ for 1.5h, filtered and diluted with saturated NaHCO 3 The solution is washed, and then the solution is washed,and washing the mixture for 5 times by using deionized water, and drying the mixture to obtain the compound shown in the structural formula I.
Examples 1 to 3
10g of the compound of formula II of example 1 was weighed accurately, 50ml of acetonitrile solution was added, then 6-chloromethyl-imidazo [2,1-B ] thiazole (3.5g, 0.02mol) was added and stirred at 30 ℃ for 1h, filtered, washed with 0.001M NaOH solution, washed with deionized water for 5 times and dried to give the compound of formula I.
Example 2
Preparing a multifunctional amino-functionalized silica gel represented by structural formula II: a solution of 3-chloropropylthiopropyltrimethoxysilane (0.3 mol) and diethylenetriamine (0.6 mol) was heated to 70 ℃ with stirring for 2 hours, a 1, 2-dichloroethane solution (0.3 mol) was added, the solution was heated with stirring at 100 to 110 ℃ for 3 hours, methanol (150 mL) was added and the solution was heated with stirring for 1 hour, and then cooled. This solution was added to a stirred mixture of silica gel (200g, 60-200 μm, 100-140) and toluene (400 mL), the mixture was stirred and refluxed for 6 hours, the solid was cooled and filtered, washed centrifugally with ethanol (3 × 400 mL) and dried to give the compound of formula II, where m is 3, p is 2,a, b and c are all present, and d and e are both zero.
Example 2-1
20g of the compound of the formula II prepared in example 2 were weighed out accurately, 120ml of methanol were added, and 5-bromo-2 (chloromethyl) -imidazo [2,1-A ] was added]Pyridine (9.2g, 0.04mol) was stirred at 65 ℃ for 8h, filtered and diluted with saturated NaKCO 3 Washing the solution, washing the solution with deionized water for 5 times, and drying the solution to obtain the compound shown in the structural formula I.
Examples 2 to 2
Accurately weigh 20g of the compound of formula II prepared in example 2, add 150ml N, N-dimethylformamide, then 2-chloro-5-chloromethylthiazole (16.8g, 0.1mol) and 10ml triethylamine, stir at 120 ℃ for 0.5h, filter, and add 1M Na 2 CO 3 Washing the solution, washing the solution for 5 times by using deionized water, and drying the solution to obtain the compound shown in the structural formula I.
Examples 2 to 3
20g of the compound of formula II prepared in example 2 were weighed accurately, added to 200 ml of dimethylsulfoxide solution, then added with 3- (chloromethyl) pyrazole hydrochloride (18.5 g, 0.12mol) and 15ml of triethylamine, stirred at 90 ℃ for 1.5h, filtered, washed with 0.02M NaOH solution, washed with deionized water for 5 times and dried to give the compound of formula I.
Application example 1
5g of the compound represented by the structural formula I obtained in example 1-1 was added to 100ml of a 1M hydrochloric acid system having concentrations of 200 ppm each of Pd (II), rh (III) and Ir (III), and the mixture was stirred at room temperature for 30 minutes, and the filtrate was analyzed by ICP-MS, whereby the removal rate of Pd was 99% and the removal rate of Rh and Ir was less than 5%. The same experiment was performed using the compounds represented by the formula I obtained in examples 1 to 2,1 to 3,2 to 1,2 to 2,2 to 3, and the results were the same. The material has very good adsorption rate to divalent palladium, and can selectively adsorb palladium from rhodium and iridium.
Application example 2
An electronic grade reagent methanol containing 1.05 pmm Ni, 0.73ppm Cu, 0.5ppm Zn, 0.48ppm Ca, 0.22 ppm Mg was added to 100ml of this methanol reagent, 2g of the compound represented by the formula I obtained in example 1-2 was added thereto, and the mixture was stirred at room temperature for 1 hour to analyze the concentration of the filtrate, whereby it was found that the concentrations of Ni, cu, zn, ca and Mg were all less than 0.001ppm.
Application example 3
A certain zinc gluconate solution contains 1.28ppm Cd and 0.5ppm Pb, 100ml of the solution is taken, added with the compound shown in the structural formula I obtained in the example 2-3, stirred at normal temperature for 2 hours, and the concentration of the filtrate is analyzed, so that neither Cd nor Pb is detected.
Application example 4
1g of the product of formula I obtained in examples 1-3 was added to 100mL of a waste solution containing 50ppm of ferrous and ferric iron. The mixture was stirred at 30 ℃ for 6h and then filtered. Analysis of the filtrate showed that ferrous iron had been removed. The products from examples 1-1,1-2,2-1,2-2,2-3 have the same effect in this test.
Application example 5
The product of formula I from example 2-1 (10 g) was loaded into a 20mL adsorption column, a waste stream of pH 6 containing 6ppm copper, 2 pmm nickel and 5ppm cobalt was passed through the column at a flow rate of 1mL/min, and after 2h the filtrate was analyzed for copper, nickel and cobalt adsorption rates of > 99%. Eluting the adsorption column with 10ml of nitric acid solution with pH of 5, analyzing to completely elute cobalt, retaining copper and nickel in the adsorption column, eluting the adsorption column with 10ml of nitric acid solution with pH of 3, analyzing to completely elute nickel and copper, eluting the adsorption column with nitric acid solution with pH of 0, analyzing to completely elute copper. The products from examples 1-1,1-2,1-3,2-2,2-3 have the same effect in this test. The material is shown to be capable of separating copper, nickel and cobalt very well through chromatographic separation.
Application example 6
A sample containing uracil, uridine, adenosine, and adenosine was packed into a 4.6 × 250mM column using the product of formula I obtained in example 1-1, and the column was purified using acetonitrile/10 mM ammonium acetate =10:90 as mobile phase, with flow rate of 0.5ml/min, separating by chromatography, uracil at retention time of 5.6min, uridine at retention time of 9.4min, adenosine at retention time of 11.2min, and adenosine at retention time of 22.5 min. It is thus understood that the material of the present invention is effective for chromatographic separation of a biological compound.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications and equivalents made by the contents of the present invention or directly or indirectly applied to other related technical fields are included in the scope of the present invention.
Claims (10)
1. A modified functionalized silica gel material is characterized in that: is a compound shown in a structural formula I;
the compound shown in the structural formula I is obtained by reacting a compound shown in a structural formula II with an aromatic heterocyclic compound or a derivative thereof;
structural formula II is:
(ii) a Wherein Z is->Or,B、B 0 Each is H or another polyamineBut B, B 0 Not both can be H; v is a substituent group and is selected from C 1-22 Alkyl radical, C 2-22 Alkenyl or C 1-22 An alkylaryl group; w is a substituent and is selected from C 1-20 Mercaptoalkyl radical, C 2-20 Alkyl sulfide group, C 1-22 Alkylthiothioalkyl or C 2-20 Alkylene thioether alkyl, C 2-20 Alkyl thioether aryl, C 2-20 Alkylene thioether aryl or C 2-6 Alkyl group SC 2-6 Alkyl radicals or alkyl radicals>(ii) a By silicon atoms, hydrogen, straight or branched C, of other groups in formula II 1-22 Alkyl, terminal group (R) 2 ) 3 SiO 1/2 Crosslinking agents or chains>Or one or more of the silicon atoms of the other groups in formula II saturate the free valences of the silicate oxygen atoms; r is 1-3 Are independently selected from straight chain or branched chain C 1-12 Alkyl, aryl and C 1-22 An alkylaryl group; k is an integer from 1 to 3; q is an integer from 1 to 2; g is an integer from 0 to 2 and satisfies->(ii) a m is an integer from 2 to 12; p is an integer from 2 to 99; t is an integer from 1 to 49; a. b, c, d, e are integers and [ a + b]C is in the range of 0.00001 to 100000; a. c are all always present; when b, d or e is greater than 0, the ratio of d + e to a + b + c is between 0.00001 and 100000;
the structural formula I is:
wherein Z is 1 Is->OrAre Y or->But B is 1 、B 2 Not both can be Y; y is one of the following structural formulas: />
Wherein the variable group on the structural formula is R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 (ii) a In the above formula, at least one of the variable groups isThe other variable groups in the structural formula are respectively and independently selected from H and C 1-3 Alkyl radical, C 2-6 Alkenyl radical, C 3-6 Alkynyl, aryl, C 1-6 Alkylaryl, cl, br, I or-NO 2 。
2. The modified functionalized silica gel material of claim 1, wherein p is an integer from 2 to 30; the t is an integer of 1 to 14.
3. The method for preparing a modified functionalized silica gel material according to claim 1 or 2,
a process for the preparation of a compound of formula I comprising the steps of:
1) Will be provided withIs associated with the corresponding amine->Reaction to form silaneIs a halide;
2) Reacting the silane obtained in step 1) with 1, 2-dichloroethane and an amineReacting the mixture of (a);
3) Adding silane to the reaction of step 1) or 2) as requiredThen, grafting on silica gel in a solvent, or carrying out sol-gel reaction with sodium silicate or tetraalkyl orthosilicate to obtain a compound shown in a structural formula II; wherein the solvent comprises hydrocarbons, aromatics, alcohols or water; wherein the alkyl group in the tetraalkylorthosilicate is selected from C 1-6 An alkyl group;
4) Mixing a compound shown as a structural formula II and an aromatic heterocyclic compound or a derivative thereof in a solvent, stirring and reacting for a certain time at a certain temperature, filtering, washing and drying to obtain a compound shown as a structural formula I;
wherein, the aromatic heterocyclic compound or the derivative thereof is YX, X is Cl, br or I, and Y is selected from one of the following structural formulas:
wherein the variable group on the structural formula is R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 (ii) a In the above formula, at least one of the variable groups isThe other variable groups in the structural formula are respectively and independently selected from H and C 1-3 Alkyl radical, C 2-6 Alkenyl radical, C 3-6 Alkynyl, aryl, C 1-6 Alkylaryl, cl, br, I or-NO 2 。
4. The method for preparing a modified functionalized silica gel material according to claim 3,
the solvent in the step 4) is at least one of methanol, dimethyl sulfoxide, dichloromethane, acetonitrile, chloroform and N, N-dimethylformamide.
5. The method for preparing the modified functionalized silica gel material according to claim 3,
the ratio of the gram mass of the compound shown in the structural formula II to the mass of the substance of the aromatic heterocyclic compound or the derivative thereof is 1g (0.001 to 10) mol.
6. The preparation method of the modified functional silica gel material as claimed in claim 3, wherein the reaction temperature in the step (4) is 30 to 150 ℃ and the reaction time is 0.5 to 12h.
7. The use of the modified functionalized silica gel material according to claim 1 or 2, wherein the compound of formula I is used as an adsorbent for adsorbing metal ions.
8. The use of the modified functionalized silica gel material according to claim 7, wherein the compound represented by the structural formula I is used as an adsorbent for electronic chemical metal impurity removal, medical and intermediate metal impurity removal, and precious metal recovery.
9. The use of the modified functionalized silica gel material according to claim 1 or 2, wherein the compound of formula I is used as an adsorbent as a chromatography medium.
10. The use of the modified functionalized silica gel material according to claim 9, characterized in that the compound of formula I is used as an adsorbent as a chromatography medium for the purification and separation of metals, metal complexes, organic compounds or biological compounds.
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