CN116178607B - Uranium adsorption resin and its preparation method and application - Google Patents
Uranium adsorption resin and its preparation method and application Download PDFInfo
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- CN116178607B CN116178607B CN202310222776.7A CN202310222776A CN116178607B CN 116178607 B CN116178607 B CN 116178607B CN 202310222776 A CN202310222776 A CN 202310222776A CN 116178607 B CN116178607 B CN 116178607B
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- adsorption resin
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- 229910052770 Uranium Inorganic materials 0.000 title claims abstract description 73
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 58
- 229920005989 resin Polymers 0.000 title claims abstract description 41
- 239000011347 resin Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 26
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000005576 amination reaction Methods 0.000 claims abstract description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 17
- 239000011574 phosphorus Substances 0.000 claims abstract description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000002378 acidificating effect Effects 0.000 claims abstract description 15
- 239000002270 dispersing agent Substances 0.000 claims abstract description 14
- 238000002156 mixing Methods 0.000 claims abstract description 13
- 239000002351 wastewater Substances 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 8
- 230000008961 swelling Effects 0.000 claims abstract description 7
- -1 hydrogen ions Chemical class 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008098 formaldehyde solution Substances 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920001444 polymaleic acid Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 150000008301 phosphite esters Chemical class 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 2
- JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical group C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 102100040653 Tryptophan 2,3-dioxygenase Human genes 0.000 description 1
- 101710136122 Tryptophan 2,3-dioxygenase Proteins 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- NMRIWJZVFRZDSS-UHFFFAOYSA-N amino dihydrogen phosphite Chemical compound NOP(O)O NMRIWJZVFRZDSS-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- NWTUPGIBLHOQQV-UHFFFAOYSA-N bis(3-methylbutyl) hydrogen phosphite Chemical compound CC(C)CCOP(O)OCCC(C)C NWTUPGIBLHOQQV-UHFFFAOYSA-N 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000777 hematopoietic system Anatomy 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/16—Halogens
- C08F212/18—Chlorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
-
- 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
- C02F2101/006—Radioactive compounds
-
- 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
- C02F2101/10—Inorganic compounds
- C02F2101/105—Phosphorus compounds
-
- 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)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Engineering & Computer Science (AREA)
- Hydrology & Water Resources (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
本发明公开了一种铀吸附树脂及其制备方法和应用。制备方法包括以下步骤：(1)将100～150重量份的氯化苯乙烯、9.5～15重量份的二乙烯苯和1.2～2.0重量份的引发剂混合，然后与11～20重量份的C5‑C9链烷烃混合，得到有机相；将有机相与500～700重量份的分散剂溶液混合，在60～90℃下反应7～12h，得到聚合产物；(2)将聚合产物溶胀，然后加入50～80重量份的乙二胺或三甲胺，在60～80℃下反应12～18h，得到胺化产物；(3)将胺化产物与300～500重量份的含醛溶液、300～400重量份的亚磷酸酯和80～150重量份的酸性催化剂混合，在80～95℃下反应12～24h，得到铀吸附树脂。本发明的树脂对酸性含磷含铀废水中的铀具有良好的吸附效果。The invention discloses a uranium adsorption resin and a preparation method and application thereof. The preparation method comprises the following steps: (1) mixing 100 to 150 parts by weight of chlorostyrene, 9.5 to 15 parts by weight of divinylbenzene and 1.2 to 2.0 parts by weight of an initiator, and then mixing with 11 to 20 parts by weight of C5-C9 chain alkane to obtain an organic phase; mixing the organic phase with 500 to 700 parts by weight of a dispersant solution, and reacting at 60 to 90° C. for 7 to 12 hours to obtain a polymer product; (2) swelling the polymer product, and then adding 50 to 80 parts by weight of ethylenediamine or trimethylamine, and reacting at 60 to 80° C. for 12 to 18 hours to obtain an amination product; (3) mixing the amination product with 300 to 500 parts by weight of an aldehyde-containing solution, 300 to 400 parts by weight of a phosphite and 80 to 150 parts by weight of an acidic catalyst, and reacting at 80 to 95° C. for 12 to 24 hours to obtain a uranium adsorption resin. The resin of the invention has a good adsorption effect on uranium in acidic phosphorus-containing and uranium-containing wastewater.
Description
Technical Field
The invention relates to uranium adsorption resin, a preparation method and application thereof.
Background
Most of the waste liquid of uranium ore hydrometallurgy is acid leaching liquid. If the uranyl ions in the acid leaching solution cannot be recycled, not only is the waste of uranium resources caused, but also the life and health of people are greatly threatened. Uranium is a harmful substance that causes radioactive contamination of the environment, and is absorbed by green plants and enters biological chains to accumulate in the living body, damaging the hematopoietic system, and causing many diseases.
At present, a solvent extraction method is mainly adopted at home and abroad to extract uranium from wet phosphoric acid, kerosene is used as a diluent, D2EHPA and TOPO/TRPO are used for synergistic extraction or trilaurin is used as an extractant, and a uranium product meeting the standard is obtained through secondary back extraction. Because the complexing ability of uranyl ions and P is extremely strong, uranium is difficult to effectively remove in a high phosphoric acid environment. Therefore, the development of an effective solid adsorption material for recycling uranium from wet-process phosphoric acid has great practical significance.
CN106507795B discloses a sulfuric acid-resistant and chloridized uranium extraction-resistant chelate resin and a synthesis method thereof, and the method comprises the following steps of (1) swelling a styrene-divinylbenzene skeleton chlorine ball in a dichloromethane solvent, adding hexamethylenetetramine for ammoniation, adjusting the pH value to 9-10, heating to 60-80 ℃ for reaction for 10-15 h, (2) filtering, washing with water, hydrolyzing with an HCl aqueous solution to obtain ammonia balls, (3) reacting the ammonia balls with formaldehyde solution and phosphorous acid, acidifying to the pH value of 1-2, stirring for 40-60 h at 90-95 ℃ to obtain an amino-phosphoric acid resin, (4) reacting the amino-phosphoric acid resin with fatty alcohol in a hydrochloric acid aqueous solution, and stirring for reaction for 10-15 h at 75-85 ℃. The resin has better tolerance to sulfuric acid and chlorella, although the resin can be used for adsorbing uranium, the traditional chlorella adopted in the synthetic method of the resin is obtained after chloromethylation, a cancerogenic substance chloromethyl ether can be used in the chloromethylation process, certain risks and injuries can be brought, and phosphorous acid is adopted in the synthetic resin process, the resin is obtained through multi-step reaction, and the reaction process is complicated.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a method for preparing a uranium adsorption resin, which has a good tolerance to acid and phosphorus, can selectively adsorb uranium, and has a good adsorption effect. Another object of the present invention is to provide a uranium adsorption resin prepared according to the preparation method described above. It is a further object of the present invention to provide the use of a uranium adsorbent resin. The invention realizes the aim through the following technical scheme.
In one aspect, the invention provides a method for preparing uranium adsorption resin, comprising the following steps:
(1) Mixing 100-150 parts by weight of chlorinated styrene, 9.5-15 parts by weight of divinylbenzene and 1.2-2.0 parts by weight of an initiator, and then mixing with 11-20 parts by weight of C5-C9 alkane to obtain an organic phase, mixing the organic phase with 500-700 parts by weight of a dispersing agent solution, and reacting for 7-12 hours at 60-90 ℃ to obtain a polymerization product;
(2) Swelling a polymerization product, adding 50-80 parts by weight of ethylenediamine or trimethylamine, and reacting for 12-18 hours at 60-80 ℃ to obtain an amination product;
(3) Mixing the aminated product with 300-500 parts by weight of aldehyde-containing solution, 300-400 parts by weight of phosphite ester and 80-150 parts by weight of acid catalyst, and reacting for 12-24 hours at 80-95 ℃ to obtain the uranium adsorption resin.
In the step (1), after uniformly mixing the chlorinated styrene, the divinylbenzene, the initiator, the C5-C9 alkane and the aqueous solution containing the dispersing agent, suspension polymerization reaction is carried out to obtain a polymerization product.
In the present invention, the amount of the chlorinated styrene may be 100 to 150 parts by weight, preferably 110 to 130 parts by weight. The amount of divinylbenzene may be 9.5 to 15 parts by weight, preferably 10 to 12 parts by weight. The initiator may be used in an amount of 1.2 to 2.0 parts by weight, preferably 1.4 to 1.8 parts by weight.
The amount of C5-C9 alkane may be 11 to 20 parts by weight, preferably 13 to 15 parts by weight. The invention discovers that the proportion of the alkane of C5-C9 has important influence on the pore structure of the polymerization product, the alkane of C5-C9 can be added to carry out pore canal design in the process of synthesizing the polymerization product, the macroporous polymerization product can be obtained, and the subsequent amination reaction and the synthesis of the resin with the amino phosphite ester group are more facilitated.
The dispersant solution may be used in an amount of 500 to 700 parts by weight, preferably 550 to 650 parts by weight.
In step (1), the reaction temperature may be 60 to 90 ℃, preferably 70 to 80 ℃. The reaction time may be 7 to 12 hours, preferably 10 to 12 hours. The polymerization reaction is carried out with stirring. The stirring speed can be 100-200 r/min, and is preferably 130-150 r/min.
After the reaction is finished, the reaction product is filtered, washed and dried to obtain a polymerization product. The filtration may be carried out by filtration means conventional in the art. Alternatively, methanol and tap water may be used for washing. The drying temperature can be 40-60 ℃.
According to the preparation method of the present invention, preferably, the chlorinated styrene is p-chlorostyrene.
According to the preparation method, the initiator is preferably selected from one of benzoyl peroxide, azodiisobutyronitrile and lauroyl peroxide, more preferably the initiator is benzoyl peroxide, the dispersing agent solution contains 0.1-1wt% of dispersing agent, more preferably the dispersing agent contains 0.4-0.6wt% of dispersing agent, the dispersing agent is selected from one of polyvinyl alcohol, oxidized polyvinyl alcohol and polymaleic acid, and more preferably the dispersing agent is polyvinyl alcohol.
According to the preparation process of the present invention, preferably, the C5-C9 alkane is a mixture of linear and branched alkanes. The weight ratio of linear alkane to branched alkane in the mixture may be 1:1 to 3, preferably 1:1. According to the preparation method of the present invention, preferably, the linear alkane is one or more of n-pentane, n-hexane, n-heptane and n-octane, and more preferably, the linear alkane is n-hexane or n-heptane. The branched alkane is selected from one or more of branched alkanes with methyl, dimethyl or trimethyl groups, more preferably the branched alkane is selected from branched alkanes with methyl groups, which may be 2-methylpentane, 2-methylhexane or 2-methylheptane, according to a specific embodiment of the invention the branched alkane is 2-methylheptane.
In the step (2), the pH value of the system is regulated to be more than 9 after the polymerization product is swelled, and then the amination reaction is carried out with ethylenediamine or trimethylamine, so as to obtain an amination product. The invention discovers that the amination reagent in the amination reaction has great influence on the adsorption capacity due to different reactivity and the number of bonded amino groups, and in the invention, the amination reagent can be ethylenediamine or trimethylamine, preferably ethylenediamine, so that the amination reaction is more favorable to be carried out, and the adsorption capacity of the resin is improved. The swelling agent may be one or more of toluene, dichloroethane, carbon tetrachloride, tetrahydrofuran, preferably toluene or carbon tetrachloride, more preferably toluene. The swelling agent may be used in an amount of 120 to 200 parts by weight, preferably 140 to 160 parts by weight. The swelling time may be 30 to 60 minutes, preferably 40 to 50 minutes. The amount of ethylenediamine or trimethylamine may be 50 to 80 parts by weight, 60 to 70 parts by weight. The temperature of the amination reaction may be 60 to 80 ℃, preferably 60 to 70 ℃. The reaction time may be 12 to 18 hours, preferably 12 to 14 hours.
After the reaction is finished, the reaction product is filtered, washed and dried to obtain an aminated product. The filtration may be carried out by filtration means conventional in the art. The aqueous solution can be washed to neutrality by using dilute hydrochloric acid and water.
In the step (3), the amination product is mixed and reacted with aldehyde-containing solution, phosphite ester and acid catalyst to obtain uranium adsorption resin. The invention discovers that the phosphite ester can be directly synthesized into the amino phosphite ester by a one-step method through introducing an acid catalyst, so that the traditional multi-step synthesis is avoided, and the reaction process is simplified.
The aldehyde-containing solution may be used in an amount of 300 to 500 parts by weight, preferably 400 to 480 parts by weight. The phosphite may be used in an amount of 300 to 400 parts by weight, preferably 300 to 350 parts by weight, and the acid catalyst may be used in an amount of 80 to 150 parts by weight, preferably 100 to 120 parts by weight.
In step (3), the reaction temperature may be 80 to 95 ℃, preferably 85 to 90 ℃. The reaction time may be 12 to 24 hours, preferably 14 to 16 hours. The synthesis of the phosphoramidate is more facilitated under the above-mentioned dosage and reaction conditions.
According to the preparation method of the present invention, preferably, the phosphite is selected from dialkyl phosphites, and the alkyl group in the dialkyl phosphites has 1 to 5 carbon atoms. The alkyl group can be an alkyl group, and the alkyl group can be one or more of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl and isopentyl, preferably one or more of methyl, ethyl, n-propyl and n-butyl. According to the preparation method of the invention, preferably, the alkyl in the dialkyl phosphite is selected from linear alkyl with 1-3 carbon atoms, and the linear alkyl can be methyl, ethyl or n-propyl, preferably ethyl.
According to the preparation method of the present invention, preferably, the aldehyde in the aldehyde-containing solution is selected from one of formaldehyde, acetaldehyde and propionaldehyde. In certain embodiments, the aldehyde is formaldehyde, and in other embodiments, the aldehyde is acetaldehyde. The acidic catalyst is selected from citric acid or hydrochloric acid, more preferably concentrated hydrochloric acid.
On the other hand, the invention also provides the uranium adsorption resin prepared by the preparation method, which has better tolerance to acid and phosphorus, can selectively adsorb uranium, has good adsorption effect, and has the adsorption quantity of more than 40 mg/g. Preferably, the adsorption quantity of uranium by the uranium adsorption resin is 50-61.6 mg/g.
In a further aspect, the invention also provides the use of a uranium adsorption resin according to the above described uranium in adsorbing acidic phosphorus-containing uranium-containing wastewater. The concentration of hydrogen ions in the acidic uranium-containing phosphorus-containing wastewater is 0.2-2.0 mol/L, and the concentration of phosphate radical is not higher than 45g/L.
According to the invention, phosphite ester is utilized to react with p-chloropolystyrene-divinylbenzene copolymer with amino under an acidic condition to obtain uranium adsorption resin, which has good tolerance to acid and phosphorus and good adsorption effect to uranium in acidic phosphorus-containing uranium-containing wastewater. The adsorption quantity of uranium by the uranium adsorption resin is more than 40 mg/g.
Detailed Description
The present invention will be further described with reference to the following specific embodiments, but the scope of the present invention is not limited thereto.
The test method is described as follows:
infrared spectroscopic analysis
Analysis was performed using a fourier transform infrared absorption spectrometer model TENSOR II manufactured by bruke, germany.
Adsorption performance test of uranium
And (3) placing the uranium adsorption resin in acidic uranium-bearing phosphorus wastewater (solid-liquid ratio is 1:200) for adsorption test. The different acidic uranium-bearing phosphate waste water is obtained by diluting stock solution, wherein the stock solution is from a certain uranium-bearing phosphorite land immersion liquid in Guizhou, the phosphate radical concentration is 40-50 g/L, the sulfate radical concentration is 20-30 g/L, the uranium concentration is 100-150 mg/L, and the H + concentration is 2.8-3.6 mol/L. Wherein the hydrogen ion concentration and the phosphate concentration are adjusted by adding phosphoric acid, sulfuric acid and sodium phosphate. The adsorption temperature is 15-40 ℃ and the adsorption time is 6-10 h. After adsorption, the supernatant was analyzed for uranium ion concentration. Uranium ion concentrations were tested as specified by HJ 840-2017.
The uranium adsorption capacity is calculated as follows:
Adsorption capacity = (V 1 x initial uranium ion concentration-V 2 x concentration of uranium ions in adsorption tail liquid)/mass of adsorption resin.
Wherein V 1 is the volume of acidic phosphorus-containing uranium-containing wastewater, the unit is mL, and V 2 is the volume of adsorption tail liquid, the unit is mL. The uranium ion concentration unit is g/L. The mass unit of the adsorption resin is g.
Example 1
1.5G of benzoyl peroxide and 120g of p-chlorostyrene are mixed, 10.5g of divinylbenzene, 6.5g of 2-methylheptane and 6.5g of n-hexane are then added to obtain an organic phase, 600ml of 0.6wt% aqueous polyvinyl alcohol solution are mixed with the organic phase and reacted for 10 hours at a temperature of 80 ℃ and a stirring speed of 155r/min to obtain a reaction product, and the reaction product is filtered, washed alternately with methanol/water and dried at 50 ℃ to obtain a polymerization product.
116G of the polymerization product, 150g of toluene and 65g of ethylenediamine were mixed and reacted at 65℃for 12 hours to obtain an aminated product.
160G of an amination product, 450g of formaldehyde solution, 300g of diethyl phosphite and 100ml of concentrated hydrochloric acid are mixed and reacted for 15 hours at 85 ℃, the solid is filtered out, and the uranium adsorption resin is obtained by washing with water until the mixture is neutral.
Comparative example 1
1.0G of benzoyl peroxide and 90g of p-chlorostyrene are mixed, 9g of divinylbenzene, 7.5g of 2-methylheptane and 2.5g of n-hexane are then added to obtain an organic phase, the organic phase is mixed with 400ml of 0.5wt% polyvinyl alcohol aqueous solution and reacted for 10 hours at a temperature of 75 ℃ and a stirring speed of 120r/min to obtain a reaction product, the reaction product is filtered, methanol/water is alternately washed, and the reaction product is dried at 50 ℃ to obtain a polymerization product.
80G of the polymerization product, 100g of methylene chloride and 40g of hexamethylenetetramine are mixed, the pH value of the system is adjusted to 9 by using NaOH solution, and then the mixture is reacted for 12 hours at 50 ℃ to obtain an amination product.
120G of an amination product, 200g of formaldehyde solution, 250g of diisoamyl phosphite and 50g of citric acid are mixed and reacted for 15 hours at 85 ℃, the solid is filtered out, and the uranium adsorption resin is obtained by washing with water until the mixture is neutral.
Comparative example 2
The difference from example 1 is that diethyl phosphite is replaced with phosphorous acid.
The adsorption performance of the adsorption resins of example 1 and comparative examples 1 to 2 was tested in different acidic uranium-containing phosphorus-containing wastewater, and the results are shown in table 1.
TABLE 1
As is clear from the above table, the adsorption amount of uranium by the uranium adsorption resin is 40mg/g or more, and the maximum adsorption amount reaches 61.6mg/g. The uranium adsorption resin provided by the invention has a good adsorption effect on uranium in acidic phosphorus-containing uranium-containing wastewater.
When the concentration of phosphate radical is 3.22g/L and the concentration of hydrogen ion is 0.2mol/L, the equilibrium adsorption quantity of uranium is 61.6mg/g, and when the concentration of hydrogen ion is increased to 2.0mol/L, the equilibrium adsorption quantity of uranium can still reach 51.5mg/g, which shows that the uranium adsorption resin has good tolerance to acid.
When the concentration of hydrogen ions is 1.0mol/L and the concentration of phosphate radical is 3.22g/L (converted into the content of phosphorus to be 1.05 g/L), the equilibrium adsorption quantity of uranium is 54.9mg/g, and when the concentration of phosphate radical is increased to 44.4g/L (converted into the content of phosphorus to be 14.5 g/L), the equilibrium adsorption quantity of uranium can still reach more than 40mg/g, which indicates that the uranium adsorption resin has good tolerance to phosphorus.
The present invention is not limited to the above-described embodiments, and any modifications, improvements, substitutions, and the like, which may occur to those skilled in the art, fall within the scope of the present invention without departing from the spirit of the invention.
Claims (5)
1. The preparation method of the uranium adsorption resin for adsorbing acidic uranium-containing phosphorus wastewater is characterized by comprising the following steps of:
(1) Mixing 100-150 parts by weight of p-chlorostyrene, 9.5-15 parts by weight of divinylbenzene and 1.2-2.0 parts by weight of an initiator, and then mixing with 11-20 parts by weight of C5-C9 alkane to obtain an organic phase, mixing the organic phase with 500-700 parts by weight of a dispersing agent solution, and reacting for 7-12 hours at 60-90 ℃ to obtain a polymerization product, wherein the C5-C9 alkane is a mixture of linear alkane and branched alkane, and the weight ratio of the linear alkane to the branched alkane is 1:1-3;
(2) Swelling the polymerization product, adding 50-80 parts by weight of ethylenediamine, and reacting for 12-18 hours at 60-80 ℃ to obtain an amination product;
(3) Mixing an amination product with 300-500 parts by weight of formaldehyde solution, 300-400 parts by weight of diethyl phosphite and 80-150 parts by weight of concentrated hydrochloric acid, and reacting for 12-24 hours at 80-95 ℃ to obtain uranium adsorption resin;
The concentration of hydrogen ions in the acidic uranium-containing phosphorus-containing wastewater is 0.2-2.0 mol/L, and the concentration of phosphate radical is not higher than 45g/L.
2. The method of manufacturing according to claim 1, characterized in that:
the initiator is selected from one of benzoyl peroxide, azodiisobutyronitrile and lauroyl peroxide;
The dispersing agent solution contains 0.1-1wt% of dispersing agent, wherein the dispersing agent is selected from one of polyvinyl alcohol, oxidized polyvinyl alcohol and polymaleic acid.
3. The method of manufacturing according to claim 1, characterized in that:
The straight-chain alkane is selected from one or more of n-pentane, n-hexane, n-heptane and n-octane;
the branched alkane is selected from one or more of branched alkanes with methyl, dimethyl or trimethyl groups.
4. The uranium adsorption resin obtained by the preparation method according to any one of claims 1 to 3, wherein an adsorption amount of uranium by the uranium adsorption resin is 40mg/g or more.
5. Use of the uranium adsorption resin according to claim 4 for adsorbing uranium in acidic phosphorus-containing uranium-containing wastewater.
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