CN115386136A - Preparation method and application of aminated polyacrylamide foam adsorbent - Google Patents
Preparation method and application of aminated polyacrylamide foam adsorbent Download PDFInfo
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- CN115386136A CN115386136A CN202211052722.2A CN202211052722A CN115386136A CN 115386136 A CN115386136 A CN 115386136A CN 202211052722 A CN202211052722 A CN 202211052722A CN 115386136 A CN115386136 A CN 115386136A
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- aminated
- polyacrylamide
- adsorbent
- aminated polyacrylamide
- foam adsorbent
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- 229920002401 polyacrylamide Polymers 0.000 title claims abstract description 114
- 239000003463 adsorbent Substances 0.000 title claims abstract description 80
- 239000006260 foam Substances 0.000 title claims abstract description 75
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000001179 sorption measurement Methods 0.000 claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000000463 material Substances 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims abstract description 11
- 238000010304 firing Methods 0.000 claims abstract description 9
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims abstract description 9
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000002791 soaking Methods 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 238000004108 freeze drying Methods 0.000 claims abstract description 3
- 238000007789 sealing Methods 0.000 claims abstract description 3
- 238000007493 shaping process Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 21
- 239000011521 glass Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000693 micelle Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 abstract description 5
- 239000003651 drinking water Substances 0.000 abstract description 4
- 235000020188 drinking water Nutrition 0.000 abstract description 4
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 31
- 230000000694 effects Effects 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229920000767 polyaniline Polymers 0.000 description 12
- 239000011148 porous material Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 230000007613 environmental effect Effects 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000036632 reaction speed Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 239000003814 drug Substances 0.000 description 2
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- 238000003912 environmental pollution Methods 0.000 description 2
- 239000006261 foam material Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 lubrication Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
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- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 101001136034 Homo sapiens Phosphoribosylformylglycinamidine synthase Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000005857 PFAS Chemical class 0.000 description 1
- 102100036473 Phosphoribosylformylglycinamidine synthase Human genes 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
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- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
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- 239000003864 humus Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MCPLVIGCWWTHFH-UHFFFAOYSA-L methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
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- 239000002349 well water Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
-
- 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
- B01J20/26—Synthetic macromolecular compounds
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
-
- 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
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
-
- 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
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
-
- 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
- C02F2101/12—Halogens or halogen-containing compounds
- C02F2101/14—Fluorine or fluorine-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/24—Homopolymers or copolymers of amides or imides
- C08J2333/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/02—Polyamines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a preparation method and application of an aminated polyacrylamide foam adsorbent, wherein the preparation method of the aminated polyacrylamide foam adsorbent comprises the following steps: (1) Adding an ammonium persulfate solution and tetramethylethylenediamine into the acrylamide and N-N methylene bisacrylamide monomer raw solution, rotating, introducing into a mold, sealing the liquid level, and reacting and shaping to obtain polyacrylamide; (2) Soaking polyacrylamide in a hydrochloric acid solution, adding aniline, then adding an ammonium persulfate solution, and soaking overnight to obtain an aminated polyacrylamide gel material; (3) And freeze-drying the obtained aminated polyacrylamide gel and then firing to obtain the aminated polyacrylamide foam adsorbent. The adsorbent material prepared by the invention realizes the efficient selective adsorption removal of trace perfluorinated compounds in water through electrostatic adsorption, hydrophobic effect and formation of micelles in the adsorbent and semi-micelles on the surface of the adsorbent, and the material is low in cost and suitable for trace perfluorinated compound pollution in drinking water.
Description
Technical Field
The invention belongs to the field of pollutant degradation, and particularly relates to a preparation method and application of an aminated polyacrylamide foam adsorbent.
Background
Perfluorinated compounds (PFCs) are a new class of organofluoro compounds that were synthesized at the end of the 40 th 20 th century and consist of hydrophobic perfluoroalkyl chains and hydrophilic ionic heads (Key B D, howell R D, criddle C S, et al&Technology,2007,31,2445-2454.Fujii S, polprasert C, tanaka S, et al.New POPs in the Water environment distribution, biological interaction and treatment of fluorinated compounds-a review paper. Journal of Water Supply Research and Technology-aqua,2007,56, 313-326.). Owing to their amphiphilic nature and high stability, they have been widely used since their synthesis in various industries, such as textile, lubrication, surfactants, food packaging, non-stick coatings, electronic products, fire-fighting foams, etc., causing serious environmental pollution (Lindstrom A B, strynar M J, delinsky A D, et al. Application of WWTP bioloids and solutions of fire fighting and well water in the destination, alabama, USA. Environmental Science& Technology,2011,45(19):8015-8021.Wang Z Y,DeWitt J C,Higgins C P,et al.A never-ending story of per-and polyfluoroalkyl substances(PFASs).Environmental Science&Technology,2017, 51 (5): 2508-2518). In 2009 and 2015, perfluorooctanesulfonic acid (PFOS), perfluorooctanoic acid (PFOA) and salts thereof were listed in the stockholm convention persistent organic pollutants priority control list, in 2016, the U.S. environmental protection agency EPA in turn stipulates that the health restriction concentrations of PFOA and PFOS in drinking water are 70ng/L (Boone J S, sight C, boone T, et al. Per-and polyfluoroalkyl substations in water and treated driving waters of the United states, science of the Total Environment,2019,653 359-369. Water, wave Y w, liao C Y, et al. Perspective on the interaction of perfluorooctanesulfonic acid and perfluorooctanoic acid&Technology,2009, 43. Nevertheless, PFCs may persist in the environment due to their high thermal and chemical stability, and are hardly biodegradable, resulting in PFCs concentrations in the environment that remain high (Liu Y, zhang Y, li J, et al distribution, partial repair and reactive growth-based source analysis of legacy and engineered fluorinated alkyl residues in the dispersed phase, surface and supplemented particulate matter array area of Bohai Bay, china. Environmental Pollution,2019, 246. Research shows that PFCs in the environment mainly enter human bodies through drinking water, dietary intake and other ways, and have certain organ, nerve, reproduction, immune toxicity and carcinogenicity. The production and use of PFCs with high water solubility, such as PFOA, leads to the most severe form of PFCs contamination in water environment, making drinking water one of the most important routes for PFCs intake in human (Buck R C, franklin J, berger U, et al. Perfluor and polyfluoro alkyl subsistences in the environment: research, classification, and orientation. Integrated Environmental Assessment and Management,2011,7 (4): 513-541.). The adsorption technology has the advantages of simple and convenient operation, low energy consumption and the like, and is widely applied to the removal of PFCs in water, and the currently commonly used adsorbent mainly comprises activated carbon and ion exchange resin. But in the practical application of the method,the adsorption effect of activated carbon on hydrophobic and lipophobic PFCs is poor, and ion exchange resins have the defects of poor selectivity, high price, poor reusability and the like (Sun M, zhou H, xu B, et al 3 2 Process.environmental Science and Pollution Research,2018,25 (8): 7443-7453.Yu Q, zhang R Q, deng S B, et al.Source of perfluor and perfluor on activated carbon and resin. In addition, in the environmental water body, different types of humus, salt ions and micromolecular acid are contained, and the adsorption effect of the traditional material is greatly influenced. Therefore, the development of a novel adsorbent which is low in price and can efficiently and selectively remove PFCs is the key for treating the water body polluted by the PFCs.
In recent years, there have been increasing studies on focusing sunlight on materials having aminated structures, which can increase electrostatic adsorption of PFCs by the material through rearrangement effect of electrons, and thus, selective adsorption of PFCs is expected (Klems M J, ling Y H, ching C, et al. Reduction of a biochemical and fluorinated alkyl substituents from water, organic chemistry Edition,2019,58 (35): 12049-12053. Kawai S, kida T, takemine S, 201et al. Influence removal and conversion of microorganisms) 394.3. Composite of water and chemical chemistry, 394.42. Polyacrylamide material as an organic polymer has the characteristics of high mass transfer rate, large load capacity and good regeneration capacity, but the polyacrylamide material has the phenomenon of shrinkage or swelling in some solvents, which results in poor regeneration capacity and mechanical stability (Wei L, xu Z, wu Y L, et al.progress on hydrogels for the removal of heavymethyl from water. Journal of Hubei University (Natural Science), 2017,39 (1): 30-15.Wu M, WU R, zhang Z, et al.preparation and application of organic-silicon aqueous slurry emission. Polyaniline can be compounded with other materials due to the adjustable chemical structure and high stability of the polyaniline and the fact that the skeleton contains a large number of amino groups, the specific surface area is effectively increased, and adsorption sites are increased. However, polyaniline materials are complex to synthesize and difficult to control in morphology (mansource M S, ossman M E, farag H a, et al. Removal of Cd (II) ion from water by absorption on to polyaniline coated on sawdust. Degradation, 2011,272 (1): 301-305.Gupta V K, pathania D, kothiyal N C, et al, polyurethane zirconia (IV) silicophosphosilicate nanocomposite for the redistribution of methyl blue dye from water. Journal of Molecular Liquids,2014,190: 139-145.Shao D, hou G, li J, et al, PANI/GO as a super absorbent for the selected absorption of magnesium (VI). Chemical Engineering Journal,2014,255, 604-612.. Therefore, the development of an adsorbing material which is simple in synthesis operation, low in cost, stable in structure and capable of realizing rapid selective enrichment of PFCs in water is urgently needed.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the problems in the prior art, the invention provides a preparation method of an aminated polyacrylamide foam adsorbent, and the aminated polyacrylamide foam adsorbent prepared by the method can obviously improve the problems of poor selective adsorption effect of the conventional adsorbent on perfluorinated compounds, low reusability, high cost and easiness in influence of coexisting substances.
The invention also provides application of the aminated polyacrylamide foam adsorbent.
The technical scheme is as follows: in order to achieve the above object, the present invention provides a method for preparing an aminated polyacrylamide foam adsorbent, comprising the steps of:
(1) Preparing a raw solution of acrylamide and N-N methylene bisacrylamide monomers under a greenhouse, adding an ammonium persulfate solution and tetramethylethylenediamine, rotating, introducing into a mold, sealing the liquid level, and reacting and shaping to obtain polyacrylamide;
(2) Soaking polyacrylamide in a hydrochloric acid solution, adding aniline, then adding an ammonium persulfate solution for oxidation, and soaking overnight to obtain an aminated polyacrylamide gel material;
(3) And freeze-drying the obtained aminated polyacrylamide gel and then firing to obtain the aminated polyacrylamide foam adsorbent.
Furthermore, in the step (1), the mass fraction of the acrylamide is 10-20%, and the mass fraction of the N-N methylene bisacrylamide is 1-10%.
Further, in the step (1), the mass fraction of the ammonium persulfate solution is 10-20%, the adding amount is 5-10 μ L per ml of the reaction solution, and the adding amount of the tetramethylethylenediamine is 0.5-2 μ L per ml of the reaction solution.
Preferably, in the step (1), the mass fraction of the ammonium persulfate solution is 10%, the adding amount is 5 μ L per ml of the reaction solution, and the adding amount of the tetramethylethylenediamine is 0.5 μ L per ml of the reaction solution.
Wherein, in the step (2), the liquid surface is sealed by water or organic solvent, and the organic solvent is any one of isoamyl alcohol, water saturated isobutanol and acetone.
Further, the mass ratio of the acrylamide to the aniline is 1-5.
Preferably, the mass ratio of acrylamide to aniline is 1.
Further, the firing in the step (3) is performed by firing the material in N using a tube furnace 2 Firing for 2-4 h at 300-400 ℃ in the atmosphere.
Preferably, in step (3), the material is in N 2 Firing at 300 ℃ for 2h under the atmosphere.
The invention also provides application of the aminated polyacrylamide foam adsorbent in removing trace perfluorinated compounds in water.
Further, the process of the application is as follows: placing the aminated polyacrylamide foam adsorbent and a water solution containing a perfluorinated compound into a glass bottle, and placing the glass bottle into a constant-temperature oscillator until the adsorption is balanced.
Wherein the dosage of the aminated polyacrylamide foam adsorbent is 1-5 g/L, and the concentration of the perfluorinated compound is 1-5 mu g/L.
Preferably, the amount of the aminated polyacrylamide foam adsorbent is 1g/L and the concentration of the perfluorinated compound is 1. Mu.g/L.
Wherein the adsorption temperature is 25 +/-1 ℃, and the adsorption equilibrium time is 1-2 h.
Preferably, the adsorption temperature is 25 ℃ and the adsorption equilibrium time is 1h.
The invention obtains Polyacrylamide (PAM) through the polymerization reaction of Acrylamide (AM) and N-N Methylene Bisacrylamide (MBA), then changes the molecular structure of the polymer through composite Polyaniline (PANI), enhances the adsorption effect and the material stability, and improves the adsorption effect and the material stability of the polymer through the polymerization reaction in N 2 Heating in the atmosphere to change the surface functional groups of the material, improve the water absorption of the material, fully utilize the pore channels and finally synthesize the aminated polyacrylamide foam composite material capable of efficiently and selectively adsorbing the PFCs.
Compared with the prior art, the invention has the following remarkable advantages:
(1) The invention relates to an aminated polyacrylamide foam adsorbent for treating trace perfluorinated compounds in water, which is prepared by the steps of generating polyaniline through the polymerization reaction of aniline, aminating and compounding the polyaniline on polyacrylamide foam under the oxidation of ammonium persulfate, and performing N-type amination on the polyaniline foam 2 Heating in the atmosphere to change the surface functional groups of the material, improve the water absorption of the material and fully utilize the pore channels, so that the composite foam material has a porous structure and a higher specific surface area, and the surface amine groups can increase the electrostatic adsorption effect on the perfluorinated compounds.
(2) The aminated polyacrylamide foam adsorbent prepared by the invention can achieve adsorption balance within 15min by virtue of electrostatic adsorption and hydrophobic effect and formation of micelles inside the adsorbent and semi-micelles on the surface of the adsorbent, the adsorption rate can reach 99.5%, the high-efficiency selective adsorption removal of trace perfluorochemicals in water is realized, and the influence on the perfluorochemicals in water is small even in the presence of micromolecular acid, salts and organic matters.
(3) The aminated polyacrylamide foam adsorbent prepared by the invention can effectively remove perfluorinated compounds in water in a pH range of 2-10, has a wide pH value for adsorption, can still keep a good adsorption effect under the influence of various environmental factors, and has a good application prospect.
(4) The aminated polyacrylamide foam adsorbent provided by the invention overcomes the defects of weak adsorption action force of activated carbon on perfluorinated compounds, extremely long adsorption balance time of ion exchange resin, and poor selectivity and reusability in the traditional adsorption material, and is simple to synthesize, green, economic, nontoxic and harmless.
Drawings
FIG. 1 is a schematic diagram of the process for synthesizing an aminated polyacrylamide foam adsorbent according to the present invention;
FIG. 2 is a schematic diagram of the mechanism of adsorption of perfluorinated compounds by the aminated polyacrylamide foam adsorbent of the present invention;
FIG. 3 is a graph showing the adsorption kinetics of a perfluorinated compound in water for an aminated polyacrylamide foam adsorbent of the present invention and a control polyacrylamide, unfired aminated polyacrylamide;
FIG. 4 is a scanning electron microscope image of polyacrylamide and aminated polyacrylamide foam adsorbents, respectively, wherein 4a is polyacrylamide and 4b is aminated polyacrylamide foam adsorbent;
FIG. 5 is a graph showing the graph of mercury intrusion porosimetry mean pore size distribution of an aminated polyacrylamide foam sorbent of the present invention, along with control polyacrylamide, unfired aminated polyacrylamide;
FIG. 6 is a graph showing the adsorption kinetics of the aminated polyacrylamide foam adsorbent of the present invention to perfluorinated compounds in water under the influence of small molecular acids;
FIG. 7 is a graph showing the adsorption kinetics of the aminated polyacrylamide foam adsorbent of the present invention to perfluorinated compounds in water under the influence of natural organic substances and salts;
FIG. 8 is a graph of the reusability of the aminated polyacrylamide foam adsorbents of the present invention to adsorb perfluorochemicals in water;
FIG. 9 is a graph showing the effect of the aminated polyacrylamide foam adsorbents of the present invention on the adsorption rate of perfluorochemicals in solutions of different pH values.
Detailed Description
The invention is further illustrated by the following examples in conjunction with the drawings.
The experimental procedures described in the examples are, unless otherwise specified, conventional. The drugs and reagents are conventional drugs unless otherwise specified.
Example 1
The preparation method of the aminated polyacrylamide foam adsorbent is shown in figure 1 and comprises the following specific steps:
(1) Preparing a raw solution of acrylamide and N-N methylene bisacrylamide monomers under a greenhouse, and dissolving 3g of acrylamide and 0.3g of cross-linking agent N-N methylene bisacrylamide in 30mL of deionized water; degassing for 15min under the nitrogen atmosphere, and adding 150uL of ammonium persulfate solution with the mass fraction of 10% and 15uL of tetramethyl ethylenediamine into the reaction solution. The solution was rotated 10 cycles, taking care not to introduce air, introduced into a mold, and the liquid surface was sealed with 1mL of water to obtain polyacrylamide after setting reaction.
(2) After the polymerization reaction in the step (1) is completed, soaking the solidified polyacrylamide into 1mol/L hydrochloric acid solution, adding aniline according to the mass ratio of acrylamide to aniline of 1.
(3) In N 2 In the atmosphere, the aminated polyacrylamide gel is lyophilized and then fired in a tubular furnace for 2h at 300 ℃ to obtain the aminated polyacrylamide foam adsorbent.
The application of the aminated polyacrylamide foam adsorbent is that the aminated polyacrylamide foam adsorbent and a perfluorinated compound solution are placed in a glass bottle, so that the concentration of the aminated polyacrylamide foam adsorbent is 1g/L, the perfluorinated compound is 1 mu g/L, the glass bottle is placed in a constant-temperature oscillator, the reaction rotating speed is set to be 150r/min, the experimental temperature is 25 +/-1 ℃, and the adsorption balance is carried out for 1h.
The aminated polyacrylamide foam adsorbent prepared by the invention realizes rapid selective adsorption enrichment of trace perfluorinated compounds in water. As shown in FIG. 2, the synthesized aminated polyacrylamide foam adsorbent has a porous structure and a high specific surface area, the surface amination groups can increase the electrostatic adsorption effect on perfluorinated compounds, the adsorption mechanism of the aminated polyacrylamide foam adsorbent on perfluorinated compounds comprises electrostatic adsorption and hydrophobic effect, and the formation of micelles inside the adsorbent and semi-micelles on the surface of the adsorbent, and the material is simple to synthesize, low in cost, strong in adsorption effect compared with the traditional adsorption material, good in reusability and free of secondary pollution.
Example 2
In this embodiment, the adsorption equilibrium time and the adsorption rate of the synthesized aminated polyacrylamide foam adsorbent and the control group (polyacrylamide, aminated polyacrylamide gel) to perfluorooctanoic acid (PFOA) in water are mainly considered, and the specific steps are as follows:
respectively adding the aminated polyacrylamide foam adsorbent prepared in example 1, polyacrylamide and aminated polyacrylamide gel at a final concentration of 1g/L into a 20mL glass bottle with a cover; and adjusting the pH value of each reaction solution to 6 +/-0.1 by using 1M NaOH/HCl in PFOA solution with the final concentration of 1 mu g/L, placing a glass bottle in a constant-temperature oscillator, setting the reaction speed to be 150r/min, and setting the experiment temperature to be 25 +/-1 ℃.
The aminated polyacrylamide foam adsorbent and the control group (polyacrylamide, aminated polyacrylamide gel) were sampled at 1mL for 0, 1,2, 3,4, 7, 15, 30, 40, 60min from the start of the experiment, and the PFOA content in the water sample was measured by LC-MS/MS to calculate the remaining proportion of PFOA in the solution by the following formula (1).
As can be seen from FIG. 3, compared with the control group (polyacrylamide and aminated polyacrylamide gel), the synthesized aminated polyacrylamide foam adsorbent can reach the adsorption balance within 15min for PFOA with the concentration of 1 μ g/L in water, the effect is obviously better than that of the control group, the adsorption rate is 99.5%, and the removal effect meets the requirements of United states EPA.
Example 3
In this example, changes in surface morphology and microstructure of polyacrylamide before and after the aminated polyacrylamide foam adsorbent is obtained by compounding polyaniline are mainly examined. The method comprises the following specific steps:
the polyacrylamide and aminated polyacrylamide foam adsorbents obtained in example 1 were sliced and then observed on a Scanning Electron Microscope (SEM) QUANTA FEG 250.
As can be seen from fig. 4a and 4b, after the composition, the polyaniline chain forms a pore channel on the surface of the material, so that the structure and specific surface area of the material can be effectively stabilized, and the adsorption effect can be enhanced.
Example 4
This example mainly considers the aminated polyacrylamide foam adsorbent and the pore size of the surface of the blank polyacrylamide and the unfired aminated polyacrylamide of the control group. The method comprises the following specific steps:
2 to 3g of the aminated polyacrylamide foam adsorbent obtained in example 1 and a control group (polyacrylamide, aminated polyacrylamide gel) were taken, and the average pore diameter of the sample was measured using an Autopore IV 9510 automatic mercury porosimeter.
As can be seen from FIG. 5, the aminated polyacrylamide foam adsorbent has richer pore sizes, the maximum value of the average pore size is about 61 μm, the amination process increases the porosity of the material, and the firing process reduces the pore size of the material, so that the material has higher specific surface area and higher adsorption potential.
Example 5
This example mainly examines the influence of the adsorption equilibrium time and adsorption rate of the aminated polyacrylamide foam adsorbent on PFOA in water in the presence of small molecular acid. The method comprises the following specific steps:
to a 20mL glass bottle with a cap were added 1g/L of the aminated polyacrylamide foam adsorbent prepared in example 1 and 1. Mu.g/L of an aqueous PFOA solution, and oxalic acid (H) was added to each glass bottle 2 C 2 O 4 ) Or formic acid (HCOOH) to a concentration of 5mg/L and 10mg/L, adjusting the pH of each reaction solution to 6. + -. 0.1 with 1M NaOH/HCl, and placing the glass bottle in a constant temperature shaker, settingThe reaction speed is 150r/min, and the experimental temperature is 25 +/-1 ℃.
Sampling 1mL at 0, 1,2, 3,4, 7, 15, 30, 40 and 60min from the beginning of the experiment, measuring the PFOA content in the water sample by LC-MS/MS, calculating the residual proportion of PFOA in the solution by formula (1), and comparing the residual proportion in H 2 C 2 O 4 (5 mg/L,10 mg/L) and HCOOH (5 mg/L,10 mg/L) adsorption kinetics of the material to PFOA in water.
As can be seen from FIG. 6, H 2 C 2 O 4 And HCOOH slightly slows down the adsorption speed of the material to PFOA, the equilibrium time is prolonged to about 30min, but the adsorption percentage is not changed greatly, so that the influence of the small molecular acid on the aminated polyacrylamide foam adsorbent is small.
Example 6
This example mainly examines the influence of the aminated polyacrylamide foam adsorbent on the adsorption equilibrium time and adsorption rate of PFOA in water in the presence of salts and organic matters. The method comprises the following specific steps:
a20 mL glass bottle with a cover was charged with 1g/L of the aminated polyacrylamide foam adsorbent prepared in example 1 and 1. Mu.g/L of PFOA aqueous solution to a final concentration, naCl was added to 5mM and 10mM and Natural Organic Matter (NOM) was added to 1mg/L and 5mg/L, respectively, the pH of each reaction solution was adjusted to 6. + -. 0.1 using 1M NaOH/HCl, and the glass bottle was placed in a constant temperature shaker at a reaction rotation speed of 150r/min at an experimental temperature of 25. + -. 1 ℃.
Samples were taken at 1mL each at 0, 1,2, 3,4, 7, 15, 30, 40, 60min from the start of the experiment, PFOA content in the water sample was measured by LC-MS/MS, the remaining proportion of PFOA in the solution was calculated, and the adsorption kinetics of PFOA in the water by the material in the presence of NaCl (5 mM,10 mM) and NOM (1 mg/L,5 mg/L), respectively, were compared.
As can be seen from FIG. 7, the existence of NaCl and NOM slightly slows down the adsorption speed of the material to PFOA, the equilibrium time is prolonged to about 35min, and the adsorption percentage is slightly reduced under the influence of NaCl but still reaches the standard required by the United states environmental protection agency, so the influence of salts and natural organic matter aminated polyacrylamide foam adsorbent is not large.
Example 7
This example mainly examines the recycling effect of the aminated polyacrylamide foam adsorbent. The method comprises the following specific steps:
adding 1g/L of the aminated polyacrylamide foam adsorbent prepared in example 1 and PFOA solution with the final concentration of 1 mu g/L into a 20mL glass bottle with a cover, adjusting the pH value of each reaction solution to 6 +/-0.1 by using 1M NaOH/HCl, placing the glass bottle in a constant-temperature oscillator, setting the reaction speed to be 150r/min, setting the experiment temperature to be 25 +/-1 ℃, sampling 1mL after 1h, and measuring the PFOA content in a water sample by using LC-MS/MS.
And (3) placing the reacted aminated polyacrylamide foam material into 5mL of methanol (MeOH), oscillating for 10 hours in a constant-temperature oscillator at the rotating speed of 150r/min, taking out the desorbed aminated polyacrylamide, cleaning, drying, re-adsorbing PFOA with the concentration of 1 mu g/L, and repeating the desorption process for 5 times.
As can be seen from FIG. 8, after 5 times of recycling, the removal rate of the aminated polyacrylamide foam adsorbent to 1 mu g/L PFOA is still over 92%, and the aminated polyacrylamide foam adsorbent has good reusability.
Example 8
This example mainly examines the influence of the aminated polyacrylamide foam adsorbent on the adsorption rate of PFOA in solutions with different pH values. The method comprises the following specific steps:
adding 1g/L of the aminated polyacrylamide foam adsorbent prepared in example 1 and PFOA solution with the final concentration of 1 mu g/L into a 20mL glass bottle with a cover, respectively adjusting the pH value of each reaction solution to 2, 4, 6, 8 and 10 by using 1M NaOH/HCl, placing the glass bottle in a constant temperature oscillator, setting the reaction speed to be 150r/min, setting the experiment temperature to be 25 +/-1 ℃, sampling 1mL after 1h, and measuring the PFOA content in a water sample by using LC-MS/MS.
As can be seen from figure 9, the aminated polyacrylamide foam adsorbent has a good PFOA removing effect under a wide pH range.
Claims (10)
1. The preparation method of the aminated polyacrylamide foam adsorbent is characterized by comprising the following steps:
(1) Preparing acrylamide and N-N methylene bisacrylamide monomer original solution, adding ammonium persulfate solution and tetramethyl ethylene diamine, rotating, introducing into a mold, sealing the liquid level, and reacting and shaping to obtain polyacrylamide;
(2) Soaking polyacrylamide in a hydrochloric acid solution, adding aniline, then adding an ammonium persulfate solution, and soaking overnight to obtain an aminated polyacrylamide gel material;
(3) And freeze-drying the obtained aminated polyacrylamide gel and then firing to obtain the aminated polyacrylamide foam adsorbent.
2. The method for preparing aminated polyacrylamide foam adsorbent according to claim 1, wherein the mass fraction of acrylamide in step (1) is 10-20%, and the mass fraction of N-N methylene-bis-acrylamide is 1-10%.
3. The method for preparing aminated polyacrylamide foam adsorbent according to claim 1, wherein in step (1), water or organic solvent is used to seal the liquid surface, and the organic solvent is any one of isoamyl alcohol, water-saturated isobutanol and acetone.
4. The method for preparing aminated polyacrylamide foam adsorbent of claim 1, wherein the mass fraction of ammonium persulfate solution in step (1) is 10-20%, the amount added is 5-10 μ L per ml of reaction solution, and the amount added of tetramethylethylenediamine is 0.5-2 μ L per ml of reaction solution.
5. The method for preparing the aminated polyacrylamide foam adsorbent of claim 1, wherein aniline is added in step (2) in a mass ratio of acrylamide to aniline of 1-5.
6. The method for preparing aminated polyacrylamide foam adsorbent according to claim 1, characterized in that,in the step (3), the material is fired in a tube furnace in the presence of N 2 Firing for 2-4 h at 300-400 ℃ in the atmosphere.
7. Use of the aminated polyacrylamide foam adsorbent prepared by the preparation method of claim 1 for removing trace perfluorochemicals from water.
8. The application according to claim 7, wherein the process of applying is: placing the aminated polyacrylamide foam adsorbent and an aqueous solution containing a perfluorinated compound into a glass bottle, and placing the glass bottle into a constant-temperature oscillator until adsorption is balanced.
9. The use of the aminated polyacrylamide foam adsorbent of claim 8 for removing trace amounts of perfluorochemicals from water, wherein the aminated polyacrylamide foam adsorbent is dosed in an amount of 1-5 g/L and the concentration of perfluorochemicals is 1-5 μ g/L.
10. The use of the aminated polyacrylamide foam adsorbent of claim 8 for removing trace perfluorochemicals from water, wherein the adsorption temperature is 25 ± 1 ℃ and the adsorption equilibrium time is 1-2 h.
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