CN108212091B - Ordered mesoporous carbon material modified by octadecane and preparation method and application thereof - Google Patents
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- 241001279009 Strychnos toxifera Species 0.000 claims description 4
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 claims description 4
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- SXFKQMHYKBDBKL-UHFFFAOYSA-N methoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[SiH2]OC SXFKQMHYKBDBKL-UHFFFAOYSA-N 0.000 description 1
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- 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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
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- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
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Abstract
The invention provides a preparation method of an eighteen-carbon-modified ordered mesoporous carbon material, which comprises the following steps: 1) adding octadecyltrimethoxysilane into the toluene solution, and stirring and uniformly mixing at room temperature; 2) adding an ordered mesoporous carbon material into the stirred solution and uniformly dispersing by ultrasonic; 3) refluxing the mixed solution at 180 +/-5 ℃ for 24 h; 4) and taking out the mixed solution after the reaction, filtering the mixed solution by using a suction filtration device, washing and drying to obtain the octadecane-modified ordered mesoporous carbon material. The ordered mesoporous carbon material prepared by the embodiment of the application can enhance the adsorption capacity of the ordered mesoporous carbon material on organic matters through the interaction between carbon chains and the hydrophobic effect, and the nano-pore channel of the ordered mesoporous carbon can eliminate the interference of macromolecular substances through the molecular size effect, so that the aim of selectively adsorbing small molecular organic matters is fulfilled.
Description
Technical Field
The invention relates to a preparation method of an adsorption material of functionalized ordered mesoporous carbon, and particularly relates to a preparation method of octadecyltrimethoxysilane modified ordered mesoporous carbon.
Background
Ordered mesoporous materials are new nanostructured materials that have rapidly emerged in the last 90 s of the century. Due to the characteristics of highly ordered pore channels, large specific surface area, high porosity, narrow pore size distribution, regular pore structure, controllable pore size, higher thermal stability, chemical stability, size effect, surface effect, quantum confinement effect and the like shown by the unique structure of the ordered mesoporous material, the ordered mesoporous material is applied to the aspects of catalyst carriers, hydrogen storage materials, electrode materials and the like, so that the ordered mesoporous material gains high importance in the international chemical, physical, material, biological and other communities for birth and is rapidly developed to become one of the research hotspots across subjects.
Mesoporous carbon is a new class of non-silicon-based mesoporous materials. The uniform ordered nanopore structure of ordered mesoporous carbon allows it to have a "size exclusion" effect, to adsorb compounds smaller than or equal to its pore size, and to exclude interference from macromolecules. Compared with pure mesoporous silicon materials, the ordered mesoporous carbon material has special properties and huge specific surface area (up to 2500 m)2Per gram) and pore volume (up to 2.25cm3Per gram), highly ordered and adjustable pore size, uniform mass transfer, small diffusion resistance,High adsorption capacity, hydrophobicity, biocompatibility, corrosion resistance and the like. Therefore, the composite adsorbent is often used as an ideal adsorption material to be widely applied to adsorption enrichment and separation of heavy metal ions, organic pollutants, biological macromolecules and the like.
The inventors of the present application have found that although the ordered mesoporous carbon has a size selective adsorption ability, its surface has a relatively large amount of charges, and thus has a relatively strong hydrophobicity or a relatively weak adsorption ability to a long carbon chain type compound, thereby limiting its application.
Disclosure of Invention
The embodiment of the application provides a novel adsorbing material based on eighteen-carbon modified ordered mesoporous carbon, overcomes the defect that the traditional ordered mesoporous carbon material has stronger hydrophobicity or weaker adsorption capacity of a long carbon chain type compound, enhances the adsorption capacity of the ordered mesoporous carbon material, and enlarges the application range.
The invention provides a preparation method of an eighteen-carbon-modified ordered mesoporous carbon material, which comprises the following steps:
1) adding octadecyltrimethoxysilane into the toluene solution, and stirring and uniformly mixing at room temperature;
2) adding an ordered mesoporous carbon material into the stirred solution and uniformly dispersing by ultrasonic;
3) refluxing the mixed solution at 180 +/-5 ℃ for 24 h;
4) and taking out the mixed solution after the reaction, filtering the mixed solution by using a suction filtration device, washing and drying to obtain the octadecane-modified ordered mesoporous carbon material.
Further, the detergent used in the step 4) is toluene.
Further, the drying temperature in the step 4) is 120 ℃.
Further, the concentration of the octadecyltrimethoxysilane in the toluene solution was 0.35 mmoL/L.
Further, the concentration of the ordered mesoporous carbon material in the toluene solution is 10 g/L.
Further, the mass ratio of the octadecyl trimethoxy silane to the ordered mesoporous carbon material is 1: 15.
further, the ultrasonic temperature in the step 2) is 25 ℃, the ultrasonic time is 20min, the ultrasonic frequency is 40Hz, and the ultrasonic power is 600W.
On the other hand, the eighteen-carbon modified ordered mesoporous carbon material prepared by the method is applied to adsorption of compounds with relatively strong hydrophobicity or long carbon chain type.
On the other hand, the eighteen-carbon-modified ordered mesoporous carbon material prepared by the method is applied to adsorbing small stimulant molecules in human whole blood, wherein the small stimulant molecules are six stimulant molecules of triamterene, trenbolone, testosterone, methyltestosterone, clenbuterol and strychnine.
In another aspect, the invention provides an ordered mesoporous carbon material modified by octadecane, wherein H on hydroxyl on the surface of the ordered mesoporous carbon material is replaced by octadecyltrimethoxysilane
And (4) substitution.
The ordered mesoporous carbon based on the eighteen carbon modification prepared by the invention can extract compounds which are difficult to adsorb by unmodified ordered mesoporous carbon and have stronger hydrophobicity or long carbon chain types through the hydrophobic effect, and has wider selectivity.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and those skilled in the art can also obtain other drawings according to the drawings without creative efforts.
Fig. 1A-1B are transmission electron microscope comparison diagrams of C18-CMK8 and CMK8 prepared by the method for preparing an octadecylsilylated ordered mesoporous carbon material according to the embodiment of the present invention and the material;
FIGS. 2A to 2D are MALDI-TOF-MS spectra of target analytes in human whole blood of adsorption materials C18-CMK8 and CMK8 prepared by the preparation method of the eighteen-carbon modified ordered mesoporous carbon material provided by the embodiment of the invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The embodiment of the application provides a preparation method of an eighteen-carbon-modified ordered mesoporous carbon material, which comprises the following steps:
1) adding octadecyltrimethoxysilane into a toluene solution, stirring and uniformly mixing at room temperature, wherein the toluene solution is used as a reaction solvent to provide a high-pressure environment for reaction;
2) adding an ordered mesoporous carbon material into the stirred solution and uniformly dispersing by ultrasonic;
3) refluxing the mixed solution at 180 +/-5 ℃ for 24 h;
4) and taking out the mixed solution after the reaction, filtering the mixed solution by using a suction filtration device, washing and drying to obtain the octadecane-modified ordered mesoporous carbon material.
The washing agent adopted in the step 4) is toluene, the toluene is used as a washing agent and used for removing unreacted octadecyl trimethoxy silane, and the drying temperature in the step 4) is 120 ℃ so as to remove the residual toluene in the product.
The concentration of the octadecyltrimethoxysilane in the toluene solution is 0.35mmoL/L, and the concentration of the ordered mesoporous carbon material in the toluene solution is 10 g/L.
Wherein the mass ratio of the octadecyl trimethoxy silane to the ordered mesoporous carbon material is 1: 15.
wherein the ultrasonic temperature in the step 2) is 25 ℃, the ultrasonic time is 20min, the ultrasonic frequency is 40Hz, and the ultrasonic power is 600W.
In the embodiment of the application, different mesoporous carbon materials are used, and adsorption materials with different mesoporous structures and pore sizes can be prepared, so that different actual requirements are met.
As can be seen from FIGS. 1A and 1B, the modified C18-CMK8 maintains the original mesoporous structure, thereby ensuring that the modified C18-CMK8 plays a 'size exclusion' effect in the process of adsorbing a target analyte and removing the interference of macromolecules.
The ordered mesoporous carbon based on the eighteen carbon modification prepared by the invention can extract compounds which are difficult to adsorb by unmodified ordered mesoporous carbon and have stronger hydrophobicity or long carbon chain types through the hydrophobic effect, and has wider selectivity. In addition, the ordered mesoporous carbon modified based on the octadecane has higher carbon content and high hydrophobicity, can greatly increase the sample loading amount and the recovery rate, and can resist extreme pH value at the same time due to high carbon content. But also has the advantages of few preparation steps, simple device, mass production, easy realization of commercialization and the like. Therefore, the ordered mesoporous carbon based on the eighteen carbon modification of the preparation method has wide application prospects, such as purification, extraction and concentration of pollutants in an environmental water sample, such as polycyclic aromatic hydrocarbons, pesticide residues in food and beverage, drugs and metabolites in biological fluid and the like.
The present invention will be described in detail with reference to specific examples. It is intended that the scope of the invention be limited not by this detailed description, but rather by the claims appended hereto.
Example 1 was carried out:
the method for preparing the ordered mesoporous carbon based on the eighteen carbon modification comprises the following steps:
adding 0.15mL of octadecyl trimethoxy silane reagent into 20mL of toluene solution, magnetically stirring at room temperature for 10min, uniformly mixing, then adding 0.2g of ordered mesoporous carbon material CMK-8, performing ultrasonic dispersion for 20min, performing reflux reaction at 185 ℃ for 24h, performing suction filtration on the reacted mixed solution by using a suction filtration device, washing with toluene, and drying at 120 ℃ for 12h to obtain a product, namely the C18 modified CMK-8 mesoporous carbon adsorption material.
The reaction principle of example 1 of the present invention:
the 3 methoxyl groups (-OCH3) connected with silicon in the octadecyl methoxyl silane are firstly hydrolyzed into silicon hydroxyl (Si-OH); then Si-OH and hydroxyl (-OH) on the surface of the ordered mesoporous carbon material form a hydrogen bond; in the heating and refluxing process, along with dehydration reaction, Si-OH of silane forms a covalent bond C-O-Si connection on the surface of the ordered mesoporous carbon.
The chemical reaction equation is as follows:
ordered mesoporous carbon
The C18 modified CMK-8 mesoporous carbon prepared in example 1 is used as an adsorbing material for stimulant micromolecules in human whole blood
Adsorption was performed, and the adsorption effect of the adsorbent was evaluated by detecting the adsorbed stimulant using MALDI-TOF MS. The selected small stimulant molecules are six small stimulant molecules of triamterene, trenbolone, testosterone, methyltestosterone, clenbuterol and strychnine.
In application, the adsorbing material C18-CMK8 is prepared into an aqueous solution with the concentration of 10 g/L.
In application, the volume ratio of the added C18-CMK8 to the human whole blood sample is 10: 1.
In application, the adsorption temperature is 25 ℃ and the adsorption time is 1 h.
In the application, the adsorption effect is compared by using the unmodified CMK-8.
The experimental results are shown in FIGS. 2A-2D (experiments using CMK-8 and C18-CMK8 as adsorbents respectively to analyze MS patterns of six stimulants in human whole blood, wherein (A) no extraction, (B) no labeling extraction is performed by C18-CMK8, (C) labeling extraction is performed by CMK-8 and (D) labeling extraction is performed by C18-CMK 8), wherein characteristic peaks of triamterene, trenbolone, clenbuterol, testosterone, methyltestosterone and strychnine correspond to m/z 254.1 respectively; m/z 270.2 and 455.4; m/z 277; m/z 288.2 and 473.5; m/z302.2 and 487.5; m/z 335.2. As can be seen from FIG. 1, the results show that no signal was detected at all without enrichment. After adsorption, extraction and enrichment by C18-CMK8, molecular ion characteristic peaks of all target analytes are successfully detected from a complex sample, and after adsorption and enrichment by CMK8, only four kinds of triamterene, trenbolone, testosterone and methyltestosterone can be detected. Compared with CMK8, C18-CMK8 can detect more stimulant-like small molecules and has higher peak intensity. The C18-CMK8 adsorbent is proved to have higher adsorption efficiency and show good adsorption performance.
The material disclosed by the invention has the beneficial effects that:
1. the C18-CMK8 can effectively remove the interference effect of a sample matrix, and has higher peak intensity and cleaner background than the unmodified CMK-8.
2. C18-CMK8 was able to successfully detect the molecular ion signature peaks for all target analytes from a complex sample, whereas unmodified CMK-8 was able to detect only four.
The prepared ordered mesoporous carbon based on the eighteen carbon modification can be used as an adsorption material, and has stronger adsorption performance than an unmodified ordered mesoporous carbon material.
The foregoing is directed to embodiments of the present invention, and it is understood that various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of the invention.
Claims (4)
1. A method for adsorbing small stimulant molecules in human whole blood by using an eighteen-carbon-modified ordered mesoporous carbon material is characterized by comprising the following steps of:
a. preparing an adsorbing material C18-CMK8 into an aqueous solution with the concentration of 10 g/L;
b. the volume ratio of the added C18-CMK8 to the human whole blood sample is 10: 1;
c. the adsorption temperature is 25 ℃, and the adsorption time is 1 h;
wherein the stimulant micromolecules are six stimulant micromolecules of triamterene, trenbolone, testosterone, methyltestosterone, clenbuterol and strychnine;
the preparation method of the eighteen-carbon-modified ordered mesoporous carbon material comprises the following steps: 1) adding octadecyltrimethoxysilane into the toluene solution, and stirring and uniformly mixing at room temperature; the concentration of the octadecyl trimethoxy silane in the toluene solution is 0.35 mmoL/L;
2) adding an ordered mesoporous carbon material into the stirred solution and uniformly dispersing by ultrasonic; the concentration of the ordered mesoporous carbon material in a toluene solution is 10 g/L; the mass ratio of the octadecyl trimethoxy silane to the ordered mesoporous carbon material is 1: 15; the ordered mesoporous carbon material is CMK-8;
3) refluxing the mixed solution at 180 +/-5 ℃ for 24 h;
4) taking out the reacted mixed solution, filtering the mixed solution by using a suction filtration device, washing and drying the filtered mixed solution to obtain the CMK-8 mesoporous carbon adsorption material modified by the eighteen carbons;
the octadecane-modified ordered mesoporous carbon material is used for adsorbing compounds with stronger hydrophobicity or long carbon chain types;
wherein H on hydroxyl on the surface of the ordered mesoporous carbon material is substituted by octadecyltrimethoxysilane by the method
And (4) substitution.
2. The method as claimed in claim 1, wherein the detergent used in the step 4) is toluene.
3. The method as claimed in claim 1 or 2, wherein the drying temperature in the step 4) is 120 ℃.
4. The method according to claim 1 or 2, wherein the ultrasonic temperature in the step 2) is 25 ℃, the ultrasonic time is 20min, the ultrasonic frequency is 40Hz, and the ultrasonic power is 600W.
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|---|---|---|---|---|
| CN103599763A (en) * | 2013-11-21 | 2014-02-26 | 南京理工大学 | Amino-functional ordered mesoporous carbon material and preparation method and application thereof |
| CN104084135A (en) * | 2014-06-30 | 2014-10-08 | 华南理工大学 | Preparation method and application of double-functional ordered mesoporous silica adsorbing agent |
| CN105618012A (en) * | 2014-11-07 | 2016-06-01 | 中国科学院大连化学物理研究所 | Organic-inorganic hybrid integrated separation material preparation method |
| CN106582539A (en) * | 2016-12-19 | 2017-04-26 | 扬州大学 | Amino-modified mesoporous carbon CMK-3 material and preparation method as well as application thereof |
| CN106925223A (en) * | 2017-01-23 | 2017-07-07 | 张龙 | A kind of mesoporous material and its method of modifying and purposes |
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2018
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103599763A (en) * | 2013-11-21 | 2014-02-26 | 南京理工大学 | Amino-functional ordered mesoporous carbon material and preparation method and application thereof |
| CN104084135A (en) * | 2014-06-30 | 2014-10-08 | 华南理工大学 | Preparation method and application of double-functional ordered mesoporous silica adsorbing agent |
| CN105618012A (en) * | 2014-11-07 | 2016-06-01 | 中国科学院大连化学物理研究所 | Organic-inorganic hybrid integrated separation material preparation method |
| CN106582539A (en) * | 2016-12-19 | 2017-04-26 | 扬州大学 | Amino-modified mesoporous carbon CMK-3 material and preparation method as well as application thereof |
| CN106925223A (en) * | 2017-01-23 | 2017-07-07 | 张龙 | A kind of mesoporous material and its method of modifying and purposes |
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