CN113000036B - Bis-thiourea modified Zr-MOF adsorption material, preparation method and application - Google Patents

Bis-thiourea modified Zr-MOF adsorption material, preparation method and application Download PDF

Info

Publication number
CN113000036B
CN113000036B CN202110333858.XA CN202110333858A CN113000036B CN 113000036 B CN113000036 B CN 113000036B CN 202110333858 A CN202110333858 A CN 202110333858A CN 113000036 B CN113000036 B CN 113000036B
Authority
CN
China
Prior art keywords
bis
uio
mof
thiourea
thiourea modified
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202110333858.XA
Other languages
Chinese (zh)
Other versions
CN113000036A (en
Inventor
郭军康
范小虎
张蕾
王家园
王磊
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shaanxi University of Science and Technology
Original Assignee
Shaanxi University of Science and Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shaanxi University of Science and Technology filed Critical Shaanxi University of Science and Technology
Priority to CN202110333858.XA priority Critical patent/CN113000036B/en
Publication of CN113000036A publication Critical patent/CN113000036A/en
Application granted granted Critical
Publication of CN113000036B publication Critical patent/CN113000036B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
    • 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
    • B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
    • B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B11/00—Obtaining noble metals
    • C22B11/04—Obtaining noble metals by wet processes
    • C22B11/042—Recovery of noble metals from waste materials
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B7/00—Working up raw materials other than ores, e.g. scrap, to produce non-ferrous metals and compounds thereof; Methods of a general interest or applied to the winning of more than two metals
    • C22B7/006—Wet processes
    • 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)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

The invention discloses a bis-thiourea modified Zr-MOF adsorption material, a preparation method and application. The preparation method of the bis-thiourea modified Zr-MOF adsorption material disclosed by the invention grafts bis-thiourea molecules on a metal organic framework through an amine aldehyde condensation reaction, and is simple in synthesis method and low in cost, and is used for mass production. According to the bis-thiourea modified Zr-MOF adsorption material, the adsorption performance of MOF is greatly improved by introducing bis-thiourea molecules. The application of the bisthiourea modified Zr-MOF adsorption material is not interfered by metal ions such as Cu (II), fe (III), zn (II), mn (II) and the like, has extremely high selectivity on Au (III), has extremely high reducibility on UiO-66-BTU, preferentially reduces the Au (III) into simple substances, and saves a large number of complex subsequent steps compared with the traditional gold recovery process.

Description

Bis-thiourea modified Zr-MOF adsorption material, preparation method and application
Technical Field
The invention belongs to the field of Zr-MOF modification, and particularly relates to a bis-thiourea modified Zr-MOF adsorption material, a preparation method and application.
Background
Gold has played a role as jewelry and currency in human society. In the last decade, the need for gold has grown drastically, in particular, with irreplaceability due to the explosive increase in the high-tech fields of catalysis, electrical and electronic equipment, aerospace, medical, etc. However, the current gold supply does not meet the increasing demand and the reserves of gold ores continue to decrease, so developing efficient and economical methods for recovering gold from industrial waste, mine tailings and leaching residues has been of great interest.
At present, various technologies such as extraction, electrodeposition, membrane separation, adsorption and the like are developed and adopted to recover gold ions in wastewater. Among these methods, adsorption is an attractive option because of its simplicity of operation, economy and environmental friendliness. The application of traditional adsorbents such as chitosan resin, porous carbon, nano materials and the like in waste gold recovery is studied. However, gold recovery is severely hampered by low adsorption capacity, poor selectivity, weak binding affinity, high energy consumption in industrial production.
Disclosure of Invention
The invention aims to overcome the defects of low adsorption capacity and poor selectivity of the existing gold adsorbent and provides a bis-thiourea modified Zr-MOF adsorption material, a preparation method and application thereof.
In order to achieve the purpose, the invention is realized by adopting the following technical scheme:
preparation method of bis-thiourea modified Zr-MOF adsorption material by using UiO-66-NH 2 Is a metal organic framework, glyoxal is used as a cross-linking agent, and the dithiourea molecule is grafted on UiO-66-NH through an amine aldehyde condensation reaction 2 UiO-66-BTU was obtained.
Further, the specific operation is as follows:
UiO-66-NH 2 And the dithiourea is dispersed in deionized water, glyoxal is added, the mixture is reacted under the conditions of heating in water bath and stirring, and the reaction is washed and dried after the completion of the reaction, so that the UiO-66-BTU is obtained.
Further, 3g of UiO-66-NH 2 And 3g of dithiourea are uniformly dispersed in 100mL of deionized water, heated and stirred at 60 ℃ for 20min, 16mL of glyoxal is added dropwise, and the mixture is reacted for 6h under the condition of water bath heating and stirring at 60 ℃.
Further, the UiO-66-NH 2 The preparation method of (2) comprises the following steps:
ZrCl is added to 4 And NH 2 Dissolving BDC in DMF, adding hydrochloric acid and acetic acid to obtain a reaction solution, transferring the reaction solution into a polytetrafluoroethylene high-pressure tank, heating in a microwave extraction instrument, and obtaining a reactant after completion; then washing and drying to obtain UIO-66-NH 2 。
Further, 699mg of ZrCl was added to 70mL of DMF in the reaction mixture 4 、543mg NH 2 -BDC, 0.5mL hydrochloric acid and 3mL acetic acid;
wherein the concentration of hydrochloric acid is concentrated hydrochloric acid, and the concentration of acetic acid is 36%.
Further, the reaction conditions are: heating at 120deg.C with microwave for 45min.
Further, the washing operation is as follows: wash with DMF, methanol and dichloromethane.
The bis-thiourea modified Zr-MOF adsorption material is prepared by the preparation method.
Further, the catalyst is used for selectively adsorbing gold ions and reducing the gold ions into gold simple substances.
Compared with the prior art, the invention has the following beneficial effects:
the preparation method of the bis-thiourea modified Zr-MOF adsorption material disclosed by the invention grafts bis-thiourea molecules on a metal organic framework through an amine aldehyde condensation reaction, and is simple in synthesis method and low in cost, and is used for mass production.
According to the bis-thiourea modified Zr-MOF adsorption material, the adsorption performance of MOF is greatly improved by introducing bis-thiourea molecules.
The application of the bis-thiourea modified Zr-MOF adsorption material is not interfered by metal ions of Cu (II), fe (III), zn (II) and Mn (II), has extremely high selectivity to Au (III), has extremely high reducibility to UiO-66-BTU, can preferentially reduce the Au (III) into simple substances, and saves a large number of complex subsequent steps compared with the traditional gold recovery process.
Drawings
FIG. 1 is UiO-66-NH of example 1 2 The field emission scanning electron microscope image, the projection electron microscope image and the EDS energy spectrum analysis of the UiO-66-BTU are shown in the specification, wherein (a) is a field emission scanning electron microscope image of the UiO-66-NH2, (b) is a field emission scanning electron microscope image of the UiO-66-BTU, (c) is a transmission electron microscope image of the UiO-66-NH2, (d) is a transmission electron microscope image of the UiO-66-BTU, and (e) is an EDS energy spectrum analysis of the UiO-66-BT;
FIG. 2 is UiO-66-NH of example 1 2 Adsorption performance diagram of UiO-66-BTU to Au (III);
FIG. 3 is UiO-66-NH of example 1 2 Results of selective adsorption of Au (III) by UiO-66-BTU.
Wherein UiO-66-NH 2 Namely Zr-MOF.
Detailed Description
In order that those skilled in the art will better understand the present invention, a technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in which it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, shall fall within the scope of the present invention.
It should be noted that the terms "first," "second," and the like in the description and the claims of the present invention and the above figures are used for distinguishing between similar objects and not necessarily for describing a particular sequential or chronological order. It is to be understood that the data so used may be interchanged where appropriate such that the embodiments of the invention described herein may be implemented in sequences other than those illustrated or otherwise described herein. Furthermore, the terms "comprises," "comprising," and "having," and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
The invention is described in further detail below with reference to the attached drawing figures:
example 1
Preparation of bis-thiourea modified Zr-MOF adsorbent Material (UiO-66-BTU)
699mg ZrCl 4 、543mg NH 2 Dissolving BDC mixture in 70mL DMF, adding 0.5mL hydrochloric acid and 3mL acetic acid, stirring to obtain reaction solution, transferring the reaction solution into polytetrafluoroethylene high pressure tank, heating with microwave at 120deg.C for 45min, washing precipitate with DMF, methanol and dichloromethane respectively at least three times, and drying solid powder with oven to obtain UiO-66-NH 2 ；
3g of UiO-66-NH 2 And 3g of dithiourea are uniformly dispersed in 100mL of deionized water, heated and stirred at 60 ℃ for 20min, 16mL of glyoxal is slowly added, heated and stirred in a water bath at 60 ℃ for 6h, the obtained precipitate is washed with deionized water for multiple times, and finally the UiO-66-BTU is obtained after drying in an oven.
As shown in FIG. 1, uiO-66-NH was obtained by observation with FE-SEM and TEM 2 And UiO-66-BTU surface morphology. As shown in FIGS. 1 (a) - (d), uiO-66-NH 2 And UiO-66-BTU are both octahedral in shape, formed from tiny particles on the nanometer scale. UiO-66-NH 2 And UiO-66-BTU were not significantly different in size and shape, indicating that the ingress of bis-thiourea did not destroy UiO-66-NH 2 Is a microstructure of (a). In addition, the degree of modification was evaluated using the results of the energy spectrum (EDS) analysis of UiO-66-BTU, as shown in FIG. 1 (e), in which UiO-66-BTU mainly contains carbon (57.6% by weight), oxygen (25.4% by weight), zirconium (10.7% by weight), nitrogen (4.9% by weight) and sulfur (1.4% by weight), demonstrating that bis-thiourea was successfully crosslinked in UiO-66-NH 2 On the framework.
Example 2
Adsorption experiments on Au (III)
10mg of UiO-66-BTU sample was mixed with 20mL of 400mg/L Au (III) solution, and the mixture was shaken at pH 2.0 and 25℃for 20-1440min, respectively, and the filtrate was measured at each time period by a flame atomic absorption spectrometer after filtration.
As shown in FIG. 2, the adsorption of Au (III) was very fast, accounting for about 93% of the total Au (III) during the initial 240 min. During this time, the UiO-66-BTU surface has sufficient adsorption sites to bind with Au (III) ions. Then, since most adsorption sites are occupied, the adsorption process is slowly performed with the extension of the contact time, and the equilibrium adsorption amount is reached after 300 min. The adsorption quantity of the UiO-66-BTU to Au (III) is 657.45mg/g, which is higher than that of the UiO-66-NH 2 (253.45 mg/g). The high adsorption rate within the initial 240min is due to the porous MOF structure, which penetrates deeper and deeper into the internal pores.
Example 3
Selective adsorption experiments on Au (III)
The selectivity was measured by adding 10mg UiO-66-BTU to a solution of metal ions coexisting with Zn (II), fe (III), cu (II), mn (II) and Au (III) (10 mg/L) at a concentration of 50mg/L. The residual amount of the solution was analyzed by Atomic Absorption Spectrophotometry (AAS). The adsorption amount was calculated from the difference in Au (III) concentration before and after adsorption.
In order to explore the selectivity of UiO-66-BTU in practical applications, selective adsorption experiments were performed in laboratory simulated gold mining wastewater. In this study, the concentration of Au (III) was 50mg/L and the concentration of other coexisting metal ions was 50mg/L. As shown in FIG. 3, the UiO-66-BTU preferentially captures Au (III), for Cu 2+ 、Zn 2+ And Mn of 2+ The capture capacity of (a) is negligible. Impressively, even the concentration of Au (III) was reduced to one fifth (10 mg/L) of the interfering metal, and the affinity (III) and selectivity to Au were evaluated by measuring the distribution coefficient value (Kd) of UiO-66-BTU, giving Table 1, it can be seen that the distribution coefficient value (K d ) 9998mL/g, far higher than the original UiO-66-NH 2 Distribution coefficient value (183.18 mL/g). Thus, these results indicate that UiO-66-BTU has good selectivity for Au (III) and other co-existing interfering metals. Furthermore, the high K value of the coexisting ions further illustrates the superior affinity between Au (III) and the adsorbent. In summary, uiO-66-BTU has good prospects in gold recovery applications.
TABLE 1UiO-66-NH 2 Selective adsorption results of UiO-66-BTU on Au (III)
The above is only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited by this, and any modification made on the basis of the technical scheme according to the technical idea of the present invention falls within the protection scope of the claims of the present invention.

Claims (9)

1. A preparation method of a bis-thiourea modified Zr-MOF adsorption material is characterized by comprising the steps of 2 Is a metal organic frameGlyoxal is used as a cross-linking agent, and the dithiourea is grafted on UiO-66-NH through an amine aldehyde condensation reaction 2 UiO-66-BTU was obtained.
2. The method for preparing the bis-thiourea modified Zr-MOF adsorption material according to claim 1, wherein the specific operation is as follows:
UiO-66-NH 2 And the dithiourea is dispersed in deionized water, glyoxal is added, the mixture is reacted under the conditions of heating in water bath and stirring, and after the reaction is finished, the mixture is washed and dried to obtain the UiO-66-BTU.
3. The method for preparing the bis-thiourea modified Zr-MOF adsorbent material as claimed in claim 2, wherein 3g of UiO-66-NH 2 And 3g of dithiourea are uniformly dispersed in 100mL of deionized water, heated and stirred at 60 ℃ for 20min, 16mL of glyoxal is added dropwise, and the mixture is reacted for 6h under the condition of water bath heating and stirring at 60 ℃.
4. The method for preparing a bis-thiourea modified Zr-MOF adsorbing material according to claim 1, wherein said UiO-66-NH 2 The preparation method of (2) comprises the following steps:
ZrCl is added to 4 And NH 2 Dissolving BDC in DMF, adding hydrochloric acid and acetic acid to obtain a reaction solution, transferring the reaction solution into a polytetrafluoroethylene high-pressure tank, heating in a microwave extraction instrument, and obtaining a reactant after completion; then washing and drying to obtain UIO-66-NH 2 。
5. The method for preparing a bis-thiourea modified Zr-MOF adsorbent material according to claim 4, wherein 699mg ZrCl is added to each 70mL DMF in the reaction solution 4 、543mg NH 2 -BDC, 0.5mL hydrochloric acid and 3mL acetic acid;
wherein the concentration of hydrochloric acid is concentrated hydrochloric acid, and the concentration of acetic acid is 36%.
6. The method for preparing the bis-thiourea modified Zr-MOF adsorption material according to claim 4, wherein the reaction conditions are as follows: heating at 120deg.C with microwave for 45min.
7. The method for preparing the bis-thiourea modified Zr-MOF adsorbing material according to claim 4, wherein the washing operation is: wash with DMF, methanol and dichloromethane.
8. A bis-thiourea modified Zr-MOF adsorbing material, characterized by being prepared according to the preparation method of any one of claims 1-7.
9. Use of a bis-thiourea modified Zr-MOF adsorbing material according to claim 8 for selectively adsorbing gold ions and reducing them to elemental gold.
CN202110333858.XA 2021-03-29 2021-03-29 Bis-thiourea modified Zr-MOF adsorption material, preparation method and application Active CN113000036B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110333858.XA CN113000036B (en) 2021-03-29 2021-03-29 Bis-thiourea modified Zr-MOF adsorption material, preparation method and application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110333858.XA CN113000036B (en) 2021-03-29 2021-03-29 Bis-thiourea modified Zr-MOF adsorption material, preparation method and application

Publications (2)

Publication Number Publication Date
CN113000036A CN113000036A (en) 2021-06-22
CN113000036B true CN113000036B (en) 2023-09-05

Family

ID=76408712

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110333858.XA Active CN113000036B (en) 2021-03-29 2021-03-29 Bis-thiourea modified Zr-MOF adsorption material, preparation method and application

Country Status (1)

Country Link
CN (1) CN113000036B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105289552A (en) * 2015-12-02 2016-02-03 天津工业大学 Method for rapidly adsorbing mercury ion in water based on bis-thiourea functionalized superfine fibers
CN110813244A (en) * 2019-11-17 2020-02-21 中山大学 Modified zirconium-based organic metal framework adsorbent for adsorbing lead ions and preparation method and application thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105289552A (en) * 2015-12-02 2016-02-03 天津工业大学 Method for rapidly adsorbing mercury ion in water based on bis-thiourea functionalized superfine fibers
CN110813244A (en) * 2019-11-17 2020-02-21 中山大学 Modified zirconium-based organic metal framework adsorbent for adsorbing lead ions and preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Junkang Guo，et al."Highly efficient and selective recovery of Au(III) from aqueous solution by bisthiourea immobilized UiO-66-NH2: Performance and mechanisms".《Chemical Engineering Journal》.130588（1-12）. *

Also Published As

Publication number Publication date
CN113000036A (en) 2021-06-22

Similar Documents

Publication Publication Date Title
Ahmad et al. A membrane‐supported bifunctional poly (amidoxime‐ethyleneimine) network for enhanced uranium extraction from seawater and wastewater
Guo et al. Highly efficient and selective recovery of Au (III) from aqueous solution by bisthiourea immobilized UiO-66-NH2: Performance and mechanisms
Velempini et al. Carboxymethyl cellulose thiol-imprinted polymers: Synthesis, characterization and selective Hg (II) adsorption
Li et al. Removal U (VI) from artificial seawater using facilely and covalently grafted polyacrylonitrile fibers with lysine
Morcali et al. Investigation of adsorption parameters for platinum and palladium onto a modified polyacrylonitrile-based sorbent
Liu et al. Persimmon tannin functionalized polyacrylonitrile fiber for highly efficient and selective recovery of Au (III) from aqueous solution
Fallah et al. Selective adsorption of Mo (VI) ions from aqueous solution using a surface-grafted Mo (VI) ion imprinted polymer
Zhang et al. Bacterial cellulose hybrid membrane grafted with high ratio of adipic dihydrazide for highly efficient and selective recovery of gold from e-waste
Li et al. A novel composite adsorbent for the separation and recovery of indium from aqueous solutions
Li et al. Experimental and DFT studies on highly selective separation of indium ions using silica gel/graphene oxide based ion-imprinted composites as a sorbent
Li et al. Ensuring high selectivity for preconcentration and detection of ultra-trace cadmium using a phage-functionalized metal–organic framework
Hussein et al. Nanoporous colorant sensors and captors for simultaneous recognition and recovery of gold from E-wastes
Wang et al. Cr-based MOF for efficient adsorption of Au at low concentrations
Sakti et al. Adsorption of gold (III) on ionic imprinted amino-silica hybrid prepared from rice hull ash
Xiong et al. Superior adsorption of Re (VII) by anionic imprinted chitosan-silica composite: Adsorption performance, selectivity and mechanism study
CN113000036B (en) Bis-thiourea modified Zr-MOF adsorption material, preparation method and application
Poursaberi et al. Application of Rh (III)-metalloporphyrin grafted Fe3O4 nanoparticles for the extraction of thiocyanate ions from aqueous solutions
Cheng et al. Efficient gold (Au)(III) recovery from wastewater using a mercapto-1, 3, 4-thiodiazole modified Zn-MOF
Gui et al. Selective enrichment of low concentration Au (III) from acidic chloride media by poly ionic liquid sorbent
Wang et al. An imprinted organic–inorganic hybrid sorbent for selective separation of copper ion from aqueous solution
CN111437891A (en) Anion exchange resin and preparation method and application thereof
Li et al. Targeting of platinum capture under 1+ 1 aqua regia using robust and recyclable polymeric polyamine resin: Adsorption performance and mechanism
Bayen et al. Synthesis of chromatographic material by immobilization of thioacetamide onto silica gel for easy detection and removal of mercury
Geng et al. Facile Synthesis of Cross-linked Hyperbranched Polyamidoamines Dendrimers for Efficient Hg (Ⅱ) Removal From Water
Xiang et al. Modified phenolic resin for the removal and reduction of Au (III) and simultaneously as the nano-Au (0) immobilized carrier for catalysis

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant