CN115041026B - Preparation method of organic solvent nanofiltration membrane with introduced macrocyclic molecules - Google Patents
Preparation method of organic solvent nanofiltration membrane with introduced macrocyclic molecules Download PDFInfo
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- CN115041026B CN115041026B CN202210655900.4A CN202210655900A CN115041026B CN 115041026 B CN115041026 B CN 115041026B CN 202210655900 A CN202210655900 A CN 202210655900A CN 115041026 B CN115041026 B CN 115041026B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
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- 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
- C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
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- 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
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/22—Treatment or purification of solutions, e.g. obtained by leaching by physical processes, e.g. by filtration, by magnetic means, or by thermal decomposition
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- 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
- C22B60/00—Obtaining metals of atomic number 87 or higher, i.e. radioactive metals
- C22B60/02—Obtaining thorium, uranium, or other actinides
- C22B60/0204—Obtaining thorium, uranium, or other actinides obtaining uranium
- C22B60/0217—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes
- C22B60/0252—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/006—Radioactive compounds
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- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
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- Manufacturing & Machinery (AREA)
- Environmental & Geological Engineering (AREA)
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- General Life Sciences & Earth Sciences (AREA)
- Mechanical Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Geology (AREA)
- Materials Engineering (AREA)
- Water Supply & Treatment (AREA)
- Geochemistry & Mineralogy (AREA)
- Hydrology & Water Resources (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention discloses a preparation method of a novel organic solvent nanofiltration membrane with introduced macrocyclic molecules. Dissolving macrocyclic molecules in an alkaline solution to obtain a macrocyclic molecule solution; adding an amine monomer solution, a phenol monomer solution and a buffer solution to obtain a mixed solution; and (3) placing the polymer porous carrier membrane on the mixed solution, and performing cross-linking and curing on a shaking table to obtain the novel organic solvent nanofiltration membrane with the introduced macrocyclic molecules. The polyphenol polyamine system has the advantages of rapid reaction and mild condition, and the obtained organic solvent nanofiltration membrane has good separation performance on dyes.
Description
Technical Field
The invention relates to a preparation method of an organic membrane, in particular to a preparation method of an organic solvent nanofiltration membrane with macrocyclic molecules introduced.
Background
On the one hand, with economic progress and industrial rapid development, the water demand is growing increasingly. On the other hand, the organic solvent is widely applied to the fields of petrochemical industry, medicine, textile and printing, and large-area water pollution is caused by dye sewage, industrial wastewater and the like. At present, three methods for wastewater treatment exist: physicochemical, chemical, and biological processes. The membrane separation method in the physicochemical method can effectively separate water resources and dye molecules according to the size screening effect and the daonan effect, and the water treatment of the membrane preparation method has the advantages of high efficiency, low energy consumption, various types of applicable matrix carrier membranes and the like. The nanofiltration membrane has good interception performance on substances with relative molecular mass of 200-2000, and can meet the application requirements of organic solvent separation and recovery. The flux can be effectively increased by introducing macrocyclic molecules into the nanofiltration membrane of the organic solvent. The interior of the macrocyclic molecule has a good pore structure, increases the contact surface of the solution, can provide a channel, and is favorable for polymerization of other groups due to rich groups.
For example, chinese patent publication No. CN109133306a discloses a high-efficiency precipitant for sewage treatment and a preparation method thereof, wherein the precipitant comprises polydimethyldiallyl ammonium chloride, an aqueous solution of sodium hydroxyethyl cellulose, and an aqueous solution of sodium silicate, wherein the mass ratio of sodium carboxyethyl cellulose to sodium silicate is 1: 8-1: 10, wherein the mass ratio of the polydimethyl diallyl ammonium chloride to the hydroxyethyl cellulose sodium is 1:1.7-1:2. The invention has the characteristics of larger floccules, lower dosage, no toxicity, lower synthesis price and higher precipitation efficiency.
Chinese patent publication No. CN111252842a discloses a corrosion-resistant sewage treatment membrane comprising: the base layer is made of polyvinylidene fluoride material; the impact-resistant layer is a quartz sand layer; a filter layer; the filter layer is a non-woven fabric layer; the adsorption layer is made of carbon materials; the corrosion-resistant layer is made of polytetrafluoroethylene. When the corrosion-resistant sewage treatment membrane and the sewage treatment membrane filtration separation equipment face sewage with larger impulse force, the impulse force of the sewage is reduced through the reinforced impact-resistant layer, after the impulse force is reduced through the impact-resistant layer, the sewage is highly purified after being adsorbed by the adsorption layer with strong adsorption capacity, and finally polytetrafluoroethylene is adopted as the wear-resistant layer and the corrosion-resistant layer, so that the corrosion-resistant capacity of the sewage treatment membrane is greatly improved when the sewage treatment membrane is contacted with the sewage, and the service life of the membrane is prolonged.
The Chinese patent with publication number of CN111732208A discloses a composite water purifying agent and a preparation method thereof, wherein the water purifying agent is formed by compositing a microbial water purifying agent and a chemical water purifying agent, and the microbial water purifying agent is prepared from the following components in parts by weight: 20-30 parts of bifidobacterium, 20-25 parts of spirulina, 20-40 parts of clostridium acetate and 45-50 parts of nitrifying bacillus; the chemical water purifying agent is prepared from the following components in parts by weight: 15-20 parts of ferric chloride and 6-12 parts of aluminum chloride.
The Chinese patent with publication number of CN105060441A discloses a novel sewage treatment agent which contains polymeric ferric trichloride, potassium persulfate, aluminum sulfate, polyacrylamide, polyethylenimine and bentonite, and comprises the following components in percentage by weight: 20-30% of polymeric ferric trichloride, 15-25% of potassium persulfate, 5-15% of aluminum sulfate, 20-35% of polyacrylamide, 10-25% of polyethylenimine and the balance of water. The water treatment agent aims at the waste water of the oil extraction plant, has good precipitation effect, good effluent quality and low treatment cost, and is suitable for oily sewage of the oil extraction plant. After the agent is added into sewage, suspended matters are flocculated immediately, the generated alum is large, the precipitation is quick, the efficiency is high, the strength of the flocculate is high, the hydrophobicity is good, the filter pressing is facilitated, and the sewage treatment agent has high purity, no impurity and no dust.
Among the reported methods for sewage treatment, membrane separation methods are widely used in social production, including forward osmosis membranes, microfiltration membranes, nanofiltration membranes, reverse osmosis membranes, and less methods are specifically directed to nanofiltration membranes of organic solvents.
Disclosure of Invention
In order to solve the problems in the background art, the invention provides a preparation method of an organic solvent nanofiltration membrane with introduced macrocyclic molecules, and solves the problems of complex method, high cost and low dye retention rate of the existing preparation method of the organic solvent nanofiltration membrane.
The technical scheme of the invention comprises the following steps:
1. the preparation method of the organic solvent nanofiltration membrane introducing the macrocyclic molecules comprises the following steps:
1) Dissolving macrocyclic molecules in an alkaline solution to obtain a macrocyclic molecule solution with a concentration of 0.01-90 wt%;
2) Adding an amine monomer solution with the concentration of 1.0-90 wt% and a phenol monomer solution with the concentration of 0.01-90 wt% and a buffer solution into a macrocyclic molecule solution to obtain a mixed solution;
3) Transferring the mixed solution to a weighing bottle, placing a polymer porous carrier film on the surface of the mixed solution, transferring to a shaking table for cross-linking and curing, and taking down the polymer porous carrier film to obtain the organic solvent nanofiltration membrane with the macrocyclic molecules introduced.
The alkaline solution is at least one of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium bicarbonate and ammonia water; the PH of the alkaline solution is 8-14.
The macrocyclic molecule is at least one of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, calixarene and Noria, and the concentration of the macrocyclic molecule is 0.1-90.0wt%. Noria is a bicyclic ladder-type macrocyclic molecule having a central lumen and a plurality of phenolic hydroxyl groups.
The amine monomer is at least one of polyethylenimine, dimethylformamide, hexamethylenediamine, ethylenediamine, propylenediamine, butylenediamine, pentylene diamine, triethylamine, piperazine, m-phenylenediamine, p-phenylenediamine, monoethanolamine and diethanolamine. The concentration of the amine monomer is 1.0-90.0 wt%.
The phenolic monomer is at least one of phloroglucinol, o-cresol, m-cresol, catechol, resorcinol, hydroquinone, eugenol and guaiacol. The concentration of the phenolic monomer is 0.1-90.0 wt%.
The buffer solution specifically comprises the following components: tris-HCl buffer (Tris-hydroxymethyl aminomethane hydrochloride), 0.2mol/L,25 ℃. The pH was adjusted to 8.5 with 0.1mol/L hydrochloric acid.
The polymer porous carrier membrane is at least one of polyacrylonitrile, polysulfone, polyether sulfone, polyamide, polyimide, polypropylene, polyethylene, polyvinylidene fluoride and polyvinyl chloride.
2. An organic solvent nanofiltration membrane introduced with macrocyclic molecules is obtained by the preparation method.
The organic solvent nanofiltration membrane is applied to extracting uranium from seawater.
Adding macrocyclic molecules into a polyphenol polyamine reaction system, covering a carrier film on the mixed solution, and standing to obtain the organic solvent nanofiltration membrane.
The polyphenol polyamine system has the advantages of rapid reaction and mild condition, and the obtained organic solvent nanofiltration membrane has good separation performance on dyes.
The beneficial effects of the invention are as follows:
the polyphenol polyamine system used in the invention reacts rapidly to generate a cross-linked polymer chain, so that the stability of the membrane can be improved. In addition, the inside of the macrocyclic molecule has a good pore structure, and the obtained organic solvent nanofiltration membrane has good flux and separation performance and has great application prospect.
The method solves the problems that the method not only has excellent filtering performance, but also is beneficial to realizing accurate chemical separation in industry, and greatly improves the separation and purification performance of the nanofiltration membrane.
The simple process preparation process and low-cost materials make the method have the prospect of mass production in industry and the potential of wide application in real life.
By introducing macrocyclic molecules into the interfacial polymerization reaction monomer, the microporosity of the separation layer is increased, and the water flux and other performances of the nanofiltration membrane are further improved. The discovery of this approach addresses to some extent the trade-off effect between water flux and retention efficiency.
In addition, it will inspire the search for other molecules with macrocyclic molecular chemical structures in order to assemble high performance nanofiltration membranes in the future.
Detailed Description
The invention is further described in connection with the following detailed description.
Embodiments of the invention are as follows:
example 1:
(1) Dissolving macrocyclic molecules Noria in an alkaline sodium hydroxide solution having a pH of 11 to obtain a Noria solution having a concentration of 1 wt%;
(2) Adding a polyethyleneimine monomer solution with the concentration of 2 weight percent and a phloroglucinol monomer solution with the concentration of 1 weight percent into a container, and 20ml of tris (hydroxymethyl) aminomethane-hydrochloric acid buffer solution;
(3) Transferring the mixed solution to a weighing bottle, placing a polymer porous carrier film on the mixed solution covered on the weighing bottle, standing for film formation, transferring into glutaraldehyde solution, and crosslinking and curing for 30min at the temperature of 25 ℃ in a 50-turn table to obtain the organic solvent nanofiltration membrane introducing macrocyclic molecules.
Specific embodiments 2 to 5: the alkaline solution was replaced with potassium hydroxide, calcium hydroxide, sodium bicarbonate, and aqueous ammonia, respectively, and the other conditions were the same as those in embodiment 1.
Specific embodiments 6 to 11: the alkaline solution PH was replaced with 8, 9, 10, 11, 12, 14, respectively, and the other conditions were the same as in embodiment 1.
Specific embodiments 12 to 15: the macrocyclic molecules are replaced by alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin and calixarene respectively, and the rest conditions are the same as those of the embodiment 1.
Specific embodiments 16 to 20: the macrocyclic molecule concentrations were replaced with 10, 20, 30,50,60wt% respectively, the remainder being the same as in embodiment 1.
Specific embodiments 21 to 26: amine monomers are replaced by propylene diamine, butylene diamine, triethylamine, piperazine and m-phenylenediamine respectively, and the rest conditions are the same as in the embodiment 1.
Specific embodiments 27 to 31: the amine monomer concentrations were replaced with 10, 20, 30,50,60wt% respectively, with the remainder being the same as in embodiment 1.
Specific embodiments 32 to 37: the phenolic monomers are respectively replaced by o-cresol, catechol, resorcinol, hydroquinone and eugenol, and the rest conditions are the same as those of the embodiment 1.
Specific embodiments 37 to 41: the phenolic monomer concentrations were replaced with 10, 20, 30,50,60wt% respectively, with the remainder being the same as in embodiment 1.
Specific embodiments 42 to 46: the carrier membrane types were replaced with polysulfone, polyethersulfone, polyamide, polyethylene, polyvinyl chloride, respectively, and the other conditions were the same as in embodiment 1.
Therefore, the organic solvent nanofiltration membrane has the characteristics of high flux and high dye retention rate, and can be applied to nanofiltration and dye separation; the preparation method is simple to operate.
Claims (7)
1. A preparation method of an organic solvent nanofiltration membrane introducing macrocyclic molecules is characterized by comprising the following steps: the method comprises the following steps:
1) Dissolving macrocyclic molecules in an alkaline solution to obtain a macrocyclic molecule solution with the concentration of 0.01-90 wt%;
2) Adding an amine monomer solution with the concentration of 1.0-90 wt% and a phenol monomer solution with the concentration of 0.01-90 wt% into a macrocyclic molecule solution to obtain a mixed solution;
3) Transferring the mixed solution to a weighing bottle, placing a polymer porous carrier film on the surface of the mixed solution, transferring to a shaking table for cross-linking and curing, and taking down the polymer porous carrier film to obtain an organic solvent nanofiltration membrane introduced with macrocyclic molecules;
the alkaline solution is at least one of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium bicarbonate and ammonia water; the PH of the alkaline solution is 8-14;
the macrocyclic molecule is at least one of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, calixarene and Noria.
2. The method for preparing the organic solvent nanofiltration membrane with the introduced macrocyclic molecules as claimed in claim 1, wherein the method comprises the following steps: the amine monomer is at least one of polyethylenimine, dimethylformamide, hexamethylenediamine, ethylenediamine, propylenediamine, butylenediamine, pentylene diamine, triethylamine, piperazine, m-phenylenediamine, p-phenylenediamine, monoethanolamine and diethanolamine.
3. The method for preparing the organic solvent nanofiltration membrane with the introduced macrocyclic molecules as claimed in claim 1, wherein the method comprises the following steps: the phenolic monomer is at least one of phloroglucinol, o-cresol, m-cresol, catechol, resorcinol, hydroquinone, eugenol and guaiacol.
4. The method for preparing the organic solvent nanofiltration membrane with the introduced macrocyclic molecules as claimed in claim 1, wherein the method comprises the following steps: the buffer solution specifically comprises the following components: tris-HCl buffer.
5. The method for preparing the organic solvent nanofiltration membrane with the introduced macrocyclic molecules as claimed in claim 1, wherein the method comprises the following steps: the polymer porous carrier membrane is at least one of polyacrylonitrile, polysulfone, polyether sulfone, polyamide, polyimide, polypropylene, polyethylene, polyvinylidene fluoride and polyvinyl chloride.
6. An organic solvent nanofiltration membrane incorporating macrocyclic molecules, characterized in that it is obtained by the preparation process of any one of claims 1-5.
7. The use of the macrocyclic molecule-introduced organic solvent nanofiltration membrane of claim 6, wherein: the method is applied to extracting uranium from seawater.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8895104B2 (en) * | 2011-07-01 | 2014-11-25 | International Business Machines Corporation | Thin film composite membranes embedded with molecular cage compounds |
| CN102327746B (en) * | 2011-08-23 | 2014-04-02 | 复旦大学 | Anti-pollution cyclodextrin-polymer composite nano-filtration membrane and preparation method thereof |
| CN104128102B (en) * | 2014-08-04 | 2016-03-09 | 郑州大学 | A kind of cyclo-dextrin-modified compounded organic solvent NF membrane and preparation method thereof |
| CN106731841B (en) * | 2016-12-29 | 2018-08-14 | 南京膜材料产业技术研究院有限公司 | A kind of supermolecule composite nanometer filtering film and its preparation method and application |
| CN107158980B (en) * | 2017-06-07 | 2020-04-28 | 浙江大学 | Thin-layer composite membrane based on gas/liquid interface reaction and preparation method and application thereof |
| CN107875868B (en) * | 2017-09-26 | 2020-02-21 | 浙江大学 | Composite nanofiltration membrane alternately assembled by phenol and amine and preparation method thereof |
| CN108654396A (en) * | 2018-05-25 | 2018-10-16 | 南京佳乐净膜科技有限公司 | Polymer film and preparation method with absorption heavy metal and organic pollution function |
| CN108744974B (en) * | 2018-06-26 | 2020-11-03 | 郑州大学 | Cyclodextrin grafted nano material modified organic solvent nanofiltration membrane and preparation method thereof |
| CN110314559B (en) * | 2019-07-31 | 2021-11-19 | 朱军勇 | Preparation method of interfacial polymerization composite membrane |
| EP4171787B1 (en) * | 2020-06-29 | 2024-05-22 | Aquaporin A/S | A hollow fiber and a process for preparation thereof |
| CN111871234B (en) * | 2020-07-13 | 2022-09-16 | 广东溢达纺织有限公司 | Loose nanofiltration membrane and preparation method and application thereof |
| CN113663529B (en) * | 2021-08-24 | 2022-07-22 | 北京工业大学 | Novel macrocyclic aromatic hydrocarbon composite nanofiltration membrane and preparation method thereof |
| CN114272767B (en) * | 2022-01-06 | 2022-10-21 | 天津工业大学 | Biphenyl compound organic solvent nanofiltration composite membrane and preparation method thereof |
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