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CN107417838A - A kind of macroporous ion exchange resin and its preparation method and application - Google Patents

A kind of macroporous ion exchange resin and its preparation method and application Download PDF

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Publication number
CN107417838A
CN107417838A CN201710264623.3A CN201710264623A CN107417838A CN 107417838 A CN107417838 A CN 107417838A CN 201710264623 A CN201710264623 A CN 201710264623A CN 107417838 A CN107417838 A CN 107417838A
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ion exchange
exchange resin
macroporous ion
preparation
polystyrene
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CN201710264623.3A
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Inventor
姚能平
将大庆
魏士明
樊致娟
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Anhui Wandong Chemical Co Ltd
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Anhui Wandong Chemical Co Ltd
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Priority to CN201710264623.3A priority Critical patent/CN107417838A/en
Publication of CN107417838A publication Critical patent/CN107417838A/en
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/30Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26Synthetic macromolecular compounds
    • B01J20/265Synthetic macromolecular compounds modified or post-treated polymers
    • B01J20/267Cross-linked polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054Solid 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 surface properties or porosity
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16Organic material
    • B01J39/18Macromolecular compounds
    • B01J39/20Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/28Working-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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2325/00Characterised 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 at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02Homopolymers or copolymers of hydrocarbons
    • C08J2325/04Homopolymers or copolymers of styrene
    • C08J2325/08Copolymers of styrene

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a kind of macroporous ion exchange resin preparation method, comprise the following steps:Polystyrene divinyl benzene-type macroporous ion exchange resin is prepared, perforating agent is added in preparation process;To the polystyrene divinyl benzene-type macroporous ion exchange resin chloromethylation of preparation;Obtained product is placed in solvent and is swelled, the three pungent aminated reactions of decyl tertiary amine is added, obtains macroporous ion exchange resin.The invention also discloses a kind of macroporous ion exchange resin of the present invention.The invention also discloses a kind of application of macroporous ion exchange resin.Selective adsorption of the present invention is fabulous, can be effectively used for adsorbing separation rhenium metal, can deal with the dissolving environment of complexity, and can realize and be repeatedly circulated.

Description

A kind of macroporous ion exchange resin and its preparation method and application
Technical field
The present invention relates to macroporous ion exchange resin technical field, more particularly to a kind of macroporous ion exchange resin and its system Preparation Method and application.
Background technology
Rhenium is a kind of valuable and rare metal.With excellent physical property such as:High intensity, high-melting-point, excellent prolong Malleability and mechanical stability.It is widely used in the high-new industry such as space flight, automobile, electronics.But rhenium is distributed not in nature Balanced and simultaneously discomfort presence in the form of simple substance.Rhenium is present in mostly in copper-sulphide ores, molybdenite and Rare Earth Mine and content is very low About 10-4Below the order of magnitude.These problems bring many problems to the extraction process of rhenium.
Currently, have for the separating and extracting process of rhenium:Solvent extraction and separation method of purification, oxidation-reduction method, charcoal absorption Method, ion-exchange, separation by precipitation, liquid-film method.But adsorption and separation material of these methods used in application process All have some limitations as:Ion exchange capacity is low, poor selectivity, is difficult to recycle and is difficult to deal with the molten of complexity Agent environment.
At present for the visible following research of adsorbing separation resin of rhenium:
CN102268547A is reported using epoxy resin as skeleton, and silica is load, and extractant N235, it contains Measure effectively can carry out adsorbing separation for 40-50%, the resin to molybdenum-rhenium.But there are many limitations in it:Such as extractant Adhesion with resin be difficult deal with complexity dissolving environment, while silica as load after using failure it is difficult to enter Row post processing.
《Non-ferrous metal》(the 6th phase in 2009) is reported using domestic 201*7,312, D301,213, D296 resin adsorptions Separation of Rhenium metal.But its selective absorption effect is not fine.Simultaneously this several domestic common resins to other metals from Son also has a suction-operated, antijamming capability and weaker in face of complicated solion antijamming capability.
The content of the invention
The present invention proposes a kind of macroporous ion exchange resin and its preparation method and application, product Selective adsorption pole It is good, adsorbing separation rhenium metal can be effectively used for, the dissolving environment of complexity can be dealt with, and can realize and be repeatedly circulated, and Simplicity is prepared, is easy to practical operation.
A kind of preparation method of macroporous ion exchange resin proposed by the present invention, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin is prepared, perforating agent is added in preparation process;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin chloromethylation prepared to S1;
S3, the obtained products of step S2 are placed in solvent be swelled, add the three pungent aminated reactions of decyl tertiary amine, obtain Macroporous ion exchange resin.
Preferably, in S1, polystyrene-divinylbenzene type macropore amberlite is prepared using the method for suspension polymerisation Fat.
Preferably, in S1, the degree of cross linking of the polystyrene-divinylbenzene type macroporous ion exchange resin is 5-9%.
Preferably, in S1, the perforating agent is made up of one or more in isobutanol, toluene, hexamethylene.
Preferably, in S2, during chloromethylation, using ferric trichloride as catalyst, by polystyrene-divinylbenzene Type macroporous ion exchange resin and chloromethyl ether reaction.
Preferably, in S3, the solvent is DMF and/or isobutanol.
Preferably, in S3, swelling time 2-12h.
Preferably, in S3, aminated reaction is carried out under the conditions of condensing reflux, and aminated reaction temperature is 70-140 DEG C, the aminated reaction time is 7-16h.
Preferably, in S3, the mass ratio of three pungent decyl tertiary amines and the obtained products of step S2 is 1-2:1-2.
A kind of macroporous ion exchange resin that the present invention also proposes, using the preparation method of the macroporous ion exchange resin It is made.
The application for a kind of macroporous ion exchange resin that the present invention also proposes, using the system of the macroporous ion exchange resin Macroporous ion exchange resin prepared by Preparation Method can be used for absorption and Separation of Rhenium.
The present invention has bigger serface and high porosity, enough adsorption sites can be provided for sorbing material, one Will be with selective three pungent decyl tertiary amines and resin-bonded under fixed condition, made exchanger resins with reference to the advantages of both Adsorbing separation rhenium metal can be effectively selected, exchange adsorption is occurred in specific rhenium metal, there is specific choosing for rhenium Adsorptivity is selected, and the solvent environment of complexity can be dealt with, use is simple to operate, advantages of good adsorption effect.
Polystyrene-divinylbenzene type macroporous ion exchange resin is prepared using the method for suspension polymerisation in addition, and rationally The degree of cross linking of polystyrene-divinylbenzene type macroporous ion exchange resin is controlled, and specific drilling is added in preparation process Agent, obtained resin specific surface area is high, and uniform pore diameter is suitable, improves the exchange capacity of resin;During rationally control swelling Between with aminated reaction condition, obtained resin property is stable, synthesis yield is high and environment-friendly.
The present invention has following features:
1st, ion exchange resin preparation process is simple, quick, controllable.
2nd, the novel ion exchanger resin prepared using the method for chemical graft, is firmly combined between carrier, after absorption It can elute completely, and easily desorption, easily regeneration, and can realize repeatedly, recycle.
3rd, prepared novel ion exchanger resin is as adsorption and separation material, and adsorption operations are simple, the rate of adsorption is fast, choosing Selecting property is high, and easy to use, has recuperability.
Embodiment
Below, technical scheme is described in detail by specific embodiment.
Embodiment 1
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin is prepared, perforating agent is added in preparation process;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin chloromethylation prepared to S1;
S3, the obtained products of step S2 are placed in solvent be swelled, add the three pungent aminated reactions of decyl tertiary amine, obtain Macroporous ion exchange resin.
Embodiment 2
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, the polyphenyl are prepared using the method for suspension polymerisation The degree of cross linking of ethene-divinyl benzo-type macroporous ion exchange resin is 5%, and perforating agent isobutanol is added in preparation process;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin prepared to S1 are under the conditions of ferric trichloride catalytic With chloromethyl ether chloromethylation;
S3, the obtained products of 100 parts of step S2 are placed in isobutanol be swelled by weight, swelling time 12h, added 100 part of three pungent decyl tertiary amine aminated reaction under the conditions of condensing reflux, aminated reaction temperature are 70 DEG C, aminated reaction Time is 16h, obtains macroporous ion exchange resin.
Embodiment 3
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, the polyphenyl are prepared using the method for suspension polymerisation The degree of cross linking of ethene-divinyl benzo-type macroporous ion exchange resin is 9%, and perforating agent, the drilling are added in preparation process Agent is made up of isobutanol, toluene;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin prepared to S1 are under the conditions of ferric trichloride catalytic With chloromethyl ether chloromethylation;
S3, the obtained products of 100 parts of step S2 are placed in DMF be swelled by weight, swelling time For 2h, 50 part of three pungent decyl tertiary amine aminated reaction under the conditions of condensing reflux is added, aminated reaction temperature is 140 DEG C, The aminated reaction time is 7h, obtains macroporous ion exchange resin.
Embodiment 4
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, the polyphenyl are prepared using the method for suspension polymerisation The degree of cross linking of ethene-divinyl benzo-type macroporous ion exchange resin is 7%, and perforating agent, the drilling are added in preparation process Agent is made up of isobutanol, toluene, hexamethylene;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin prepared to S1 are under the conditions of ferric trichloride catalytic With chloromethyl ether chloromethylation;
S3, the obtained products of 50 parts of step S2 are placed in solvent be swelled by weight, solvent is by DMF Formed with isobutanol, swelling time 10h, add 100 part of three pungent decyl tertiary amine aminated reaction under the conditions of condensing reflux, Aminated reaction temperature is 120 DEG C, and the aminated reaction time is 12h, obtains macroporous ion exchange resin.
Embodiment 5
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, the polyphenyl are prepared using the method for suspension polymerisation The degree of cross linking of ethene-divinyl benzo-type macroporous ion exchange resin is 7%, and perforating agent, the drilling are added in preparation process Agent is made up of isobutanol, toluene, hexamethylene;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin prepared to S1 are under the conditions of ferric trichloride catalytic With chloromethyl ether chloromethylation;
S3, the obtained products of step S2 are placed in solvent being swelled, solvent is DMF and/or isobutanol, Swelling time is 8h, adds three pungent decyl tertiary amine aminated reactions under the conditions of condensing reflux, and aminated reaction temperature is 90 DEG C, the aminated reaction time is 14h, obtains macroporous ion exchange resin.
Embodiment 6
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, its degree of cross linking are prepared using the method for suspension polymerisation For 5-9%, and perforating agent is added during the course of the reaction, isobutanol;
S2, by macroporous type styrene ions exchanger resin carry out chloromethylation;
S3, the product for obtaining S2 take 100g to be placed in DMF and are swelled 2h, then add the tri- pungent last of the ten Heavenly stems of 100g Alkyl tertiary amine, aminated reaction is carried out under conditions of condensing reflux, 90 DEG C, reaction time 12h of reaction temperature, reaction is produced Thing is cleaned, dried repeatedly, obtains macroporous ion exchange resin.
Embodiment 7
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, its degree of cross linking are prepared using the method for suspension polymerisation For 7%, and perforating agent isobutanol is added during the course of the reaction;
S2, by macroporous type styrene ions exchanger resin carry out chloromethylation;
S3, the product for obtaining S2 take 100g to be placed in DMF and are swelled 4h, then add the tri- pungent last of the ten Heavenly stems of 80g Alkyl tertiary amine, aminated reaction is carried out under conditions of condensing reflux, 100 DEG C of reaction temperature, reaction time 12h, will be reacted Product is cleaned, dried repeatedly, obtains macroporous ion exchange resin.
Embodiment 8
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, its degree of cross linking are prepared using the method for suspension polymerisation For 7%, and perforating agent isobutanol is added during the course of the reaction;
S2, by macroporous type styrene ions exchanger resin carry out chloromethylation;
S3, the product for obtaining S2 take 100g to be placed in isobutanol and are swelled 4h, then add the pungent decyl tertiary amines of 80g tri-, Aminated reaction is carried out under conditions of condensing reflux, 90 DEG C of reaction temperature is reaction time 12h, repeatedly clear by reaction product Wash, dry, obtain macroporous ion exchange resin.
Embodiment 9
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, its degree of cross linking are prepared using the method for suspension polymerisation For 7%, and perforating agent isobutanol is added during the course of the reaction;
S2, by macroporous type styrene ions exchanger resin carry out chloromethylation;
S3, the product for obtaining S2 take 100g to be placed in DMF and are swelled 4h, then add the tri- pungent last of the ten Heavenly stems of 80g Alkyl tertiary amine, aminated reaction is carried out under conditions of condensing reflux, 120 DEG C of reaction temperature, reaction time 12h, will be reacted Product is cleaned, dried repeatedly, obtains macroporous ion exchange resin.
Embodiment 10
A kind of preparation method of macroporous ion exchange resin, comprises the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin, its degree of cross linking are prepared using the method for suspension polymerisation For 7%, and perforating agent is added during the course of the reaction, perforating agent is made up of dimethylbenzene, isobutanol;
S2, by macroporous type styrene ions exchanger resin carry out chloromethylation;
S3, the product for obtaining S2 take 100g to be placed in DMF and are swelled 4h, then add the tri- pungent last of the ten Heavenly stems of 80g Alkyl tertiary amine, aminated reaction is carried out under conditions of condensing reflux, 120 DEG C of reaction time of reaction temperature are 12h, and reaction is produced Thing is cleaned, dried repeatedly, obtains macroporous ion exchange resin.
Macroporous ion exchange resin described in embodiment 1-10 can be used for absorption and Separation of Rhenium metal.
Macroporous ion exchange resin described in embodiment 1-10 is detected, test average result is as shown in the table:
Lab work Character
Outward appearance It is faint yellow
Dispatch from the factory form Unhindered amina
Water content % 50.08
Full exchange capacity mmol/g 0.91
Rate of small round spheres % after mill 98.3
Ooze mill rate of small round spheres % 96.6
Granularity (0.63-1.10) mm% 98.2
The foregoing is only a preferred embodiment of the present invention, but protection scope of the present invention be not limited thereto, Any one skilled in the art the invention discloses technical scope in, technique according to the invention scheme and its Inventive concept is subject to equivalent substitution or change, should all be included within the scope of the present invention.

Claims (10)

1. a kind of preparation method of macroporous ion exchange resin, it is characterised in that comprise the following steps:
S1, polystyrene-divinylbenzene type macroporous ion exchange resin is prepared, perforating agent is added in preparation process;
S2, the polystyrene-divinylbenzene type macroporous ion exchange resin chloromethylation prepared to S1;
S3, the obtained products of step S2 are placed in solvent be swelled, add the three pungent aminated reactions of decyl tertiary amine, obtain macropore Ion exchange resin.
2. the preparation method of macroporous ion exchange resin according to claim 1, it is characterised in that in S1, using outstanding The method of floating polymerization prepares polystyrene-divinylbenzene type macroporous ion exchange resin.
3. the preparation method of macroporous ion exchange resin according to claim 1 or 2, it is characterised in that described in S1 The degree of cross linking of polystyrene-divinylbenzene type macroporous ion exchange resin is 5-9%.
4. the preparation method of the macroporous ion exchange resin according to claim any one of 1-3, it is characterised in that in S1 In, the perforating agent is made up of one or more in isobutanol, toluene, hexamethylene.
5. the preparation method of the macroporous ion exchange resin according to claim any one of 1-4, it is characterised in that in S2 In, during chloromethylation, using ferric trichloride as catalyst, by polystyrene-divinylbenzene type macroporous ion exchange resin Reacted with chloromethyl ether.
6. the preparation method of the macroporous ion exchange resin according to claim any one of 1-5, it is characterised in that in S3 In, the solvent is DMF and/or isobutanol.
7. the preparation method of the macroporous ion exchange resin according to claim any one of 1-6, it is characterised in that in S3 In, carry out aminated reaction under the conditions of condensing reflux, and aminated reaction temperature is 70-140 DEG C, the aminated reaction time is 7-16h。
8. the preparation method of the macroporous ion exchange resin according to claim any one of 1-7, it is characterised in that in S3 In, the mass ratio of three pungent decyl tertiary amines and the obtained products of step S2 is 1-2:1-2.
9. a kind of macroporous ion exchange resin, it is characterised in that using the system of macroporous ion exchange resin described in claim 1-8 Preparation Method is made.
10. a kind of application of macroporous ion exchange resin, it is characterised in that using macropore ion exchange described in claim 1-8 Macroporous ion exchange resin prepared by the preparation method of resin can be used for absorption and Separation of Rhenium.
CN201710264623.3A 2017-04-21 2017-04-21 A kind of macroporous ion exchange resin and its preparation method and application Pending CN107417838A (en)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
CN109174208A (en) * 2018-08-30 2019-01-11 深圳市纯水号水处理科技有限公司 A kind of resin adsorption removal trace metal ion solution
CN111437891A (en) * 2020-03-03 2020-07-24 东华理工大学 Anion exchange resin and preparation method and application thereof
CN114453032A (en) * 2020-11-02 2022-05-10 中国石油化工股份有限公司 Modified ion exchange resin, preparation method thereof and application thereof in polyhydric alcohol dehydration reaction
CN115991501A (en) * 2023-01-10 2023-04-21 陕西亿杰博顺环保科技有限公司 Method for recycling molybdenum from molybdic acid-containing wastewater and comprehensive treatment process of molybdic acid-containing wastewater

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CN103755846A (en) * 2013-12-27 2014-04-30 宁波争光树脂有限公司 Synthetic method of high temperature-resistant strongly basic anion exchange resin

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109174208A (en) * 2018-08-30 2019-01-11 深圳市纯水号水处理科技有限公司 A kind of resin adsorption removal trace metal ion solution
CN111437891A (en) * 2020-03-03 2020-07-24 东华理工大学 Anion exchange resin and preparation method and application thereof
CN114453032A (en) * 2020-11-02 2022-05-10 中国石油化工股份有限公司 Modified ion exchange resin, preparation method thereof and application thereof in polyhydric alcohol dehydration reaction
CN114453032B (en) * 2020-11-02 2024-02-13 中国石油化工股份有限公司 Modified ion exchange resin, preparation method thereof and application thereof in polyol dehydration reaction
CN115991501A (en) * 2023-01-10 2023-04-21 陕西亿杰博顺环保科技有限公司 Method for recycling molybdenum from molybdic acid-containing wastewater and comprehensive treatment process of molybdic acid-containing wastewater

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Application publication date: 20171201