CN107652461B - Preparation technology and application of new imprinting material of composite metal polyphenol co-preparation - Google Patents
Preparation technology and application of new imprinting material of composite metal polyphenol co-preparation Download PDFInfo
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- CN107652461B CN107652461B CN201711114179.3A CN201711114179A CN107652461B CN 107652461 B CN107652461 B CN 107652461B CN 201711114179 A CN201711114179 A CN 201711114179A CN 107652461 B CN107652461 B CN 107652461B
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- C08F120/00—Homopolymers 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
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Abstract
The invention discloses a microwave irradiation preparation technology and application of a new imprinting material of a complex metal polyphenol co-product, the method takes a chlorogenic acid-caffeic acid-vanillic acid-protocatechuic acid mixture as a template molecule, the new imprinting material of the complex metal polyphenol co-product is prepared by microwave assistance, the reaction time is short, the imprinting efficiency of the obtained new imprinting material is high, imprinting sites are stable, the molecular acting force with the polyphenol compound is unique and stronger, the molecular recognition efficiency and the application capacity of extracting plant active parts are far higher than those of a conventional imprinting polymer, the technological progress is promoted strongly, a selectable high-efficiency adsorbent is provided for separating the active parts of the polyphenol compound, the recovery rate of a target product used once is high, the target molecule has stronger selectivity, and the method has many advantages which are not available in other methods, and the practical value is very high.
Description
Technical Field
The invention relates to a microwave irradiation preparation technology and application of a new imprinting material of a composite metal polyphenol co-preparation.
Background
When the traditional Chinese medicine is used for treating diseases, the traditional Chinese medicine is usually based on comprehensive treatment and conditioning of a Chinese medicine compound on a human body, and has synergistic regulation and treatment effects which are not possessed by western medicines. The analysis of the medicinal components shows that the strong treatment effect of the Chinese medicinal compound is mainly obtained from the active parts in the Chinese medicinal herbs, namely the synergistic mechanism of the compounds of the same category in the Chinese medicinal herbs in the treatment of diseases. The therapeutic effect of multiple components is often much greater than that of a single component biologically active compound. In order to show the curative effect of traditional Chinese medicines, the development trend that traditional Chinese medicines are different from western medicines is probably to obtain active parts from the traditional Chinese medicines. The traditional Chinese medicine achieves the purposes of treating diseases and preserving health by means of the synergistic application of multiple components. Therefore, it is of great importance to selectively extract active sites from Chinese herbs. The development of new high selectivity separation materials is an important step in achieving high efficiency separations. The molecularly imprinted polymer is a high molecular polymer which is completely matched with a target molecule in space and a binding site and is obtained by removing the target molecule after polymerizing the target molecule, a functional monomer and a cross-linking agent in a solution. The imprinted polymer can specifically identify target molecules when extracting complex samples, and therefore, the imprinted polymer is a separation medium with important application prospects.
Molecularly imprinted polymers often use a single template to create an imprint, which has a high selective extraction capacity for individual compounds. However, as many compounds, especially compounds of the same class, often have similar functional groups and similar chemical properties, molecular imprinting also shows higher selectivity for certain structurally similar compounds in recognition, in addition to high selective recognition capability for template molecules, which is the cross recognition performance of molecular imprinting. By using this property, the imprinted sites created can exhibit selective recognition of such compounds if multiple structural analogs are used as a common template.
In order to further improve the fidelity of the multi-template molecular imprinting and the stability of the imprinting sites, the molecular recognition action force of the imprinting sites can be properly enhanced by means of metal coordination bonds, and target compounds adsorbed on the imprinting sites cannot be removed. Particularly, the effective generation of multi-template imprinting sites can be enhanced by adopting composite metal ions, and the simultaneous extraction efficiency of the obtained molecularly imprinted polymer material on various molecules is improved. Through continuous experiment and repeated exploration, composite metal ions with higher coordination effect on the polyphenol compounds are searched, the combination proportion is optimized, and the coordination efficiency is improved. The microwave-assisted chemical synthesis has the advantages of high synthesis speed, simple operation, high yield and the like in the synthesis of organic compounds, but the microwave is less used in the preparation process of molecular imprinting polymers.
In the past, the single polyphenol compound imprinted polymer is prepared in bulk polymerization and in situ, chromatographic identification and solid phase extraction efficiency of the single polyphenol compound imprinted polymer are discussed, and the selective identification capability of the single polyphenol compound imprinted polymer is not high.
Disclosure of Invention
In order to obtain a new imprinting material of a composite metal-polyphenol co-preparation, the technical scheme of the invention is as follows:
(1) the molar ratio of the components is 3-10: 1 weighing Tb (NO)3)3·6H2O and MnSO4Dissolving in 100mL of deionized water, slowly dripping NaOH solution while stirring until the pH is 8.5-11, stirring, aging at room temperature for 5-8h, filtering, washing the precipitate with deionized water to neutrality, and drying at 60 deg.C for 24 h;
(2) in a container, the molar ratio of 1: 2: 2: 1 adding 0.5-1.0mmol of chlorogenic acid-caffeic acid-vanillic acid-protocatechuic acid mixture, 0.4mL of dimethyl sulfoxide (DMSO) and 6.0mL of acetonitrile-tetrahydrofuran mixed solvent (volume ratio is 1: 2), ultrasonically mixing, slightly heating, adding 1.0-2.0g of precipitate obtained in the step (1) and 0.6-2.4mL of adjuvant (0.34 mol/L of HF-NaF buffer solution), stirring and standing for 2-3h to obtain a composite metal-polyphenol complex solution;
(3) adding 0.6-2.0 mmol of acrylamide-dopamine mixed functional monomer (the molar ratio is 1: 3-10) into the solution obtained in the step (2), performing ultrasonic treatment for 10 minutes, adding 9mg of Azobisisobutyronitrile (AIBN), introducing argon for 20 minutes, performing ultrasonic mixing, and sealing a preservative film;
(4) and (3) placing the mixture solution obtained in the step (3) in a water bath, intermittently irradiating the mixture by microwaves through a preservative film (irradiation is 0.5 min-is stopped for 1.5 min), setting the microwave power to be 600-fold, stopping irradiation after reaction for 4h, taking out the generated polymer, grinding, sieving, taking solid particles of 200-fold 400 meshes, eluting the mixed template molecules by a methanol-acetic acid mixed solvent with the volume ratio of 9:1, soaking for 24h by using 50mL0.5mol/L of sodium ethylene diamine tetracetate aqueous solution, filtering, and drying the solid for 24h in vacuum, thus obtaining the new imprinting material of the composite metal-polyphenol co-complex.
The polymer obtained by the method is used as a solid phase extracting agent, added into the gutta alcohol extract solution, filtered after being extracted for a certain time, the solid is eluted by acetic acid-methanol mixed solution, eluent is collected, and the solvent is removed under reduced pressure to obtain the required product. 60-80% of polyphenol compounds in the eucommia ulmoides crude extract can be extracted by single use, and the method is suitable for extraction and purification of plant active parts and has wide application prospect.
Compared with the prior art, the invention has the beneficial effects that:
the method for preparing the composite metal-polyphenol coordination compound imprinting new material by microwave assistance is disclosed, the chemical synthesis time is greatly shortened, the imprinting efficiency of the obtained material is high, the purity of imprinting sites generated by target compound molecules is greatly improved, the imprinting sites are stable and have stronger molecular acting force with polyphenol compounds, the molecular recognition efficiency and the application capacity of extracting plant active parts are far higher than those of conventional imprinting polymers, the technological progress is forcefully promoted, a selectable high-efficiency adsorbent is provided for separating the polyphenol compound active parts, the recovery rate of target products used once is high, the target molecules have stronger selectivity, many advantages which are unavailable in other methods are possessed, and the practical value is very high.
Detailed Description
The preparation technology and application of the new imprinting material of the complex metal polyphenol compounds are explained in detail below.
Example 1:
(1) the molar ratio of the raw materials is 4: 1 weighing Tb (NO)3)3·6H2O and MnSO4Dissolving in 100mL of deionized water, slowly dripping NaOH solution while stirring until the pH is 8.5-11, stirring, aging at room temperature for 5-8h, filtering, washing the precipitate with deionized water to neutrality, and drying at 60 deg.C for 24 h;
(2) in a container, the molar ratio of 1: 2: 2: 1 adding 0.5-1.0mmol of chlorogenic acid-caffeic acid-vanillic acid-protocatechuic acid mixture, 0.4mL of dimethyl sulfoxide (DMSO) and 6.0mL of acetonitrile-tetrahydrofuran mixed solvent (volume ratio is 1: 2), carrying out ultrasonic mixing and slight heating, adding 1.2g of precipitate obtained in the step (1) and 2.0mL of assistant agent (0.34 mol/L of HF-NaF buffer solution), stirring and standing for 2-3h to obtain a composite metal-polyphenol complex solution;
(3) adding 1.6 mmol of acrylamide-dopamine mixed functional monomer (the molar ratio is 1: 8) into the solution obtained in the step (2), performing ultrasonic treatment for 10 minutes, adding 9mg of Azobisisobutyronitrile (AIBN), introducing argon for 20 minutes, performing ultrasonic mixing, and sealing a preservative film;
(4) and (3) placing the mixture solution obtained in the step (3) in a water bath, intermittently irradiating the mixture with microwaves through a preservative film (irradiation time is 0.5 min-1.5 min), setting microwave power to be 700W, stopping irradiation after reaction for 4h, taking out, grinding and sieving the generated polymer, taking solid particles of 200-400 meshes, eluting mixed template molecules with a methanol-acetic acid mixed solvent with a volume ratio of 9:1, soaking the mixed template molecules with 50mL0.5mol/L of sodium ethylene diamine tetracetate aqueous solution for 24h, filtering, and drying the solid in vacuum for 24h to obtain the new imprinting material of the composite metal-polyphenol co-formulation.
The polymer obtained by the method is used as a solid phase extracting agent, added into the gutta alcohol extract solution, filtered after being extracted for a certain time, the solid is eluted by acetic acid-methanol mixed solution, eluent is collected, and the solvent is removed under reduced pressure to obtain the required product. 60-80% of polyphenol compounds in the eucommia ulmoides crude extract can be extracted by single use, and the method is suitable for extraction and purification of plant active parts and has wide application prospect.
Example 2:
(1) the molar ratio of the components is 6: 1 weighing Tb (NO)3)3·6H2O and MnSO4Dissolving in 100mL of deionized water, slowly dripping NaOH solution while stirring until the pH is 8.5-11, stirring, aging at room temperature for 5-8h, filtering, washing the precipitate with deionized water to neutrality, and drying at 60 deg.C for 24 h;
(2) in a container, the molar ratio of 1: 2: 2: 1 adding 0.5-1.0mmol of chlorogenic acid-caffeic acid-vanillic acid-protocatechuic acid mixture, 0.4mL of dimethyl sulfoxide (DMSO) and 6.0mL of acetonitrile-tetrahydrofuran mixed solvent (volume ratio is 1: 2), carrying out ultrasonic mixing and slight heating, adding 1.5g of precipitate obtained in the step (1) and 1.7mL of assistant agent (0.34 mol/L of HF-NaF buffer solution), stirring and standing for 2-3h to obtain a composite metal-polyphenol complex solution;
(3) adding 1.6 mmol of acrylamide-dopamine mixed functional monomer (the molar ratio is 1: 9) into the solution obtained in the step (2), performing ultrasonic treatment for 10 minutes, adding 9mg of Azobisisobutyronitrile (AIBN), introducing argon for 20 minutes, performing ultrasonic mixing, and sealing a preservative film;
(4) and (3) placing the mixture solution obtained in the step (3) in a water bath, intermittently irradiating the mixture with microwaves through a preservative film (irradiation time is 0.5 min-1.5 min), setting microwave power to be 800W, stopping irradiation after reaction for 4h, taking out, grinding and sieving the generated polymer, taking solid particles of 200-400 meshes, eluting mixed template molecules with a methanol-acetic acid mixed solvent with a volume ratio of 9:1, soaking the mixed template molecules with 50mL0.5mol/L of sodium ethylene diamine tetracetate aqueous solution for 24h, filtering, and drying the solid in vacuum for 24h to obtain the new imprinting material of the composite metal-polyphenol co-formulation.
The polymer obtained by the method is used as a solid phase extracting agent, added into the gutta alcohol extract solution, filtered after being extracted for a certain time, the solid is eluted by acetic acid-methanol mixed solution, eluent is collected, and the solvent is removed under reduced pressure to obtain the required product. 60-80% of polyphenol compounds in the eucommia ulmoides crude extract can be extracted by single use, and the method is suitable for extraction and purification of plant active parts and has wide application prospect.
The above-described embodiments are not intended to limit the present invention in any manner, and those skilled in the art can make many possible variations and modifications to the technical solution of the present invention using the above-disclosed technical contents, or modify equivalent embodiments with equivalent variations, without departing from the scope of the technical solution of the present invention. Therefore, any simple modification, equivalent change and modification made to the above embodiments according to the technical spirit of the present invention should fall within the protection scope of the technical scheme of the present invention, unless the technical spirit of the present invention departs from the content of the technical scheme of the present invention.
Claims (4)
1. A method for preparing a composite metal polyphenol coditional substance imprinting material by microwave assistance is characterized by comprising the following steps:
(1) the molar ratio of the components is 3-10: 1 weighing Tb (NO)3)3·6H2O and MnSO4Dissolving the mixture in 100mL of deionized water,slowly dripping NaOH solution while stirring until the pH value is 8.5-11, stirring, aging at room temperature for 5-8h, filtering, washing precipitate with deionized water to neutrality, and drying at 60 deg.C for 24 h;
(2) in a container, the molar ratio of 1: 2: 2: 1 chlorogenic acid-caffeic acid-vanillic acid-protocatechuic acid mixture with a total substance amount of 0.5-1.0mmol, 0.4mL of dimethyl sulfoxide (DMSO), 6.0mL of volume ratio of 1: 2, ultrasonically mixing and slightly heating the acetonitrile-tetrahydrofuran mixed solvent, adding 1.0-2.0g of the precipitate obtained in the step (1) and 0.6-2.4mL of 0.34mol/L HF-NaF buffer solution as auxiliary agents, stirring and standing for 2-3h to prepare a composite metal-polyphenol complex solution;
(3) adding 0.6-2.0 mmol of a solution obtained in the step (2) into the solution with a molar ratio of 1: 3-10 parts of acrylamide-dopamine mixed functional monomer, performing ultrasonic treatment for 10 minutes, adding 9mg of Azobisisobutyronitrile (AIBN), introducing argon for 20 minutes, performing ultrasonic mixing, and sealing a preservative film;
(4) and (3) placing the mixture solution obtained in the step (3) in a water bath, intermittently irradiating the mixture by microwaves through a preservative film, stopping the irradiation for 1.5min every 0.5min, setting the microwave power to be 600-fold and 1000W, stopping the irradiation after the reaction for 4h, taking out the generated polymer, grinding and sieving, taking solid particles of 200-fold 400 meshes, eluting the mixed template molecules by a methanol-acetic acid mixed solvent with the volume ratio of 9:1, soaking the mixed template molecules by using 50mL0.5mol/L of sodium ethylene diamine tetracetate aqueous solution for 24h, filtering, and drying the solid in vacuum for 24h to obtain the new imprinting material of the composite metal-polyphenol co-complex.
2. The composite metal polyphenol coordination compound imprinted material obtained by the method of claim 1.
3. The method for using the composite metal polyphenol coordination compound imprinted material obtained by the method of claim 1 as a solid phase extracting agent.
4. A solid phase extractant, characterized by: the solid phase extractant comprises the composite metal polyphenol coordination compound imprinting material obtained by the method of claim 1.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008139204A2 (en) * | 2007-05-15 | 2008-11-20 | Imperial Innovations Ltd | Functional group imprinted polymers |
| CN103626920A (en) * | 2013-11-28 | 2014-03-12 | 东北林业大学 | Indole-3-acetic acid molecularly imprinted magnetic cellulose microsphere and preparation method and applications thereof |
| CN105130793A (en) * | 2015-09-14 | 2015-12-09 | 吉首大学 | Method of simultaneously extracting caffeic acid and ferulic acid in cimicifuga rhizome |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008139204A2 (en) * | 2007-05-15 | 2008-11-20 | Imperial Innovations Ltd | Functional group imprinted polymers |
| CN103626920A (en) * | 2013-11-28 | 2014-03-12 | 东北林业大学 | Indole-3-acetic acid molecularly imprinted magnetic cellulose microsphere and preparation method and applications thereof |
| CN105130793A (en) * | 2015-09-14 | 2015-12-09 | 吉首大学 | Method of simultaneously extracting caffeic acid and ferulic acid in cimicifuga rhizome |
Non-Patent Citations (1)
| Title |
|---|
| "鲜绿茶叶中茶多酚的提取和纯化研究";付晓风;《中国硕士学位论文全文数据库 工程科技I辑》;20130515(第05期);第8页第1.3.2节 * |
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