CN105080517A - Hybrid mesoporous silica gel matrix coated type polysaccharide chiral stationary phase and preparation method therefor - Google Patents
Hybrid mesoporous silica gel matrix coated type polysaccharide chiral stationary phase and preparation method therefor Download PDFInfo
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- CN105080517A CN105080517A CN201410197984.7A CN201410197984A CN105080517A CN 105080517 A CN105080517 A CN 105080517A CN 201410197984 A CN201410197984 A CN 201410197984A CN 105080517 A CN105080517 A CN 105080517A
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Abstract
A hybrid mesoporous silica gel matrix coated type polysaccharide chiral stationary phase is characterized in that a sol-gel method is adoped to prepare a hybrid mesoporous silica gel gel with aminopropyl in both skeleton and channel, and a polysaccharide derivative is coated on the surface thereof. The hybrid mesoporous silica gel matrix coated type polysaccharide chiral stationary phase provided by the present invention has the advantages that a synthesized chiral color spectrum stationary phase has a high specific surface area, an orderly arranged pore structure, a uniformly distributed aperture with a controllable size and a higher spectrum separation efficiency.
Description
Technical field
The present invention relates to the preparation of chromatographic stationary phases, be specifically related to a kind of preparation method of hybrid mesoporous silica-based application type chiral stationary phase.
Background technology
Along with the increase to optical pure compound demand, preparation, point analysis of variance of optical pure compound become more and more important.And chromatography is that compartment analysis chipal compounds is the simplest, the method for most convenient.Current most of chiral stationary phase is all loaded on common silica gel by chiral selector by the method for absorption or bonding.And traditional silica gel itself has deficiency, therefore select the better matrix of a kind of performance to replace silica gel.
Hybrid mesoporous silica gel adopts the silane reagent of organo-functional group bridging as functional group, prepares the hybrid mesoporous silica gel containing organo-functional group in skeleton by sol-gal process.Hybrid mesoporous silica gel has the advantages such as high-specific surface area, regularly arranged duct, narrow pore-size distribution, good hydrothermal stability, mechanical stability and chemical stability, and preparation method is simple, controllable degree is large.
The chiral chromatogram Stationary liquid of the hybrid mesoporous silica matrix utilizing conventional coating methods to prepare has excellent chiral resolution ability, can be applicable to analyze and preparative chromatography.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of hybrid mesoporous silica-based application type chiral stationary phase, by tradition ripe painting method polysaccharide derivatives is fixed on hybrid mesoporous silica-based on, there is wider pH scope of application cutter and have good stability.
The technical scheme that the present invention deals with problems is: a kind of preparation method of hybrid mesoporous silica matrix application type chiral stationary phase, is characterized in that it comprises the steps:
1) preparation of hybrid mesoporous silica gel
With 1,2-bis-(triethoxy is silica-based) ethane and triethoxy γ-aminopropylsilane reagent are silicon source, using lauryl amine and softex kw as mixed surfactant, second alcohol and water is mixed solvent, alkali is as hydrolyst, prepare hybrid mesoporous silica gel, synthetic route road as shown in Figure 1;
2) preparation of polysaccharide derivatives
Polysaccharide is placed in the reactor of organic solvent, add the excessive polysaccharide derivatization reagent for modifying, at 80 DEG C, react 24h, reaction system is cooled to room temperature, isolated by filtration, washing, and vacuum drying is for subsequent use;
3) coating of Stationary liquid
The polysaccharide derivatives of above-mentioned preparation is joined in oxolane, makes it dissolve.Appropriate polysaccharide derivates solution is added in the solvent filling the hybrid mesoporous silica gel that aminopropyl is modified, slow steaming desolventizes, repeatedly repeat above-mentioned steps until polysaccharide derivates solution is all applied complete till, so just obtained hybrid mesoporous silica matrix Polysaccharides Type Chiral Stationary Phases.
The present invention has the following advantages:
1. the chiral stationary phase matrix used that prepared by the present invention is the hybrid mesoporous silica gel of stable chemical performance, can be applied to the compartment analysis of chipal compounds in wider pH range under reverse-phase chromatography condition;
2. the hybrid mesoporous silica gel that prepared by the present invention has the mesoporous passage of high-sequential, can accelerate mass transfer, thus reduces post pressure, is applicable to the rapid analysis under high flow rate.
accompanying drawing explanation
Fig. 1 is the synthetic route chart of hybrid mesoporous silica gel
Fig. 2 is hybrid mesoporous silica matrix application type cellulose-(3,5-dimethylphenylcarbamate) chirality
[0006]stationary liquid analyzes chromatogram to styrax mesotomy, separation condition: n-hexane/isopropyl alcohol (80/20, volume ratio)
Fig. 3 is hybrid mesoporous silica matrix application type cellulose-(3,5-dimethylphenylcarbamate) chiral stationary phase is to trans 1, chromatogram is analyzed in 2 talan oxide mesotomies, separation condition: n-hexane/isopropyl alcohol (80/20, volume ratio)
detailed description of the invention:
embodiment 1
(1) preparation of hybrid mesoporous silica gel
In the round-bottomed flask of 100ml, add 3g lauryl amine, 1g softex kw, 42ml distilled water, 20ml ethanol, make it to dissolve completely under constantly stirring, regulate pH to 13 with 1MNaOH solution, keep clarification shape clear solution.By the 5ml1 mixed, 2-bis-the triethoxy γ-aminopropylsilane of (triethoxysilane) ethane and 1ml add above-mentioned clear solution, and at room temperature rapid stirring 2h.Then be transferred to by reactant liquor in 90 DEG C of standing 16h in polytetrafluoro reactor, filter, washing, 90 DEG C of dryings, obtain aminopropyl and modify hybrid mesoporous silica gel.
(2) preparation of polysaccharide derivatives
1g cellulose is placed in the three mouthfuls of round-bottomed flasks filling 40ml pyridine, then adds 5g3,5-dimethylphenyl isocyanate reacts 24h at 80 DEG C, after cooling, filters and uses methanol wash, vacuum drying, obtaining cellulose derivative.
(3) coating of Stationary liquid
By 0.6g3, the cellulose derivative that 5-dimethylphenyl isocyanate is modified is dissolved in the transparent state of tetrahydrofuran solvent, above-mentioned for 10ml solution is added 3.5g aminopropyl to be modified in hybrid mesoporous silica gel, slow steaming removing oxolane, repeatedly repeat above-mentioned steps until solution of cellulose derivative is all applied complete till, i.e. obtained hybrid mesoporous substrate application type Polysaccharides Type Chiral Stationary Phases.
embodiment 2
1) preparation of hybrid mesoporous silica gel
In the round-bottomed flask of 000ml, add 15g lauryl amine, 5g softex kw, 200ml distilled water, 100ml ethanol, make it to dissolve completely under constantly stirring, regulate pH to 13 with 1MNaOH solution, keep clarification shape clear solution.By the 25ml1 mixed, 2-bis-the triethoxy γ-aminopropylsilane of (triethoxysilane) ethane and 5ml add above-mentioned clear solution, and at room temperature rapid stirring 2h.Then be transferred to by reactant liquor in 90 DEG C of standing 16h in polytetrafluoro reactor, filter, washing, 90 DEG C of dryings, obtain aminopropyl and modify hybrid mesoporous silica gel;
2) preparation of polysaccharide derivatives
5g cellulose is placed in the three mouthfuls of round-bottomed flasks filling 200ml pyridine, then adds 25g3,5-dimethylphenyl isocyanate reacts 24h at 80 DEG C, after cooling, filters and uses methanol wash, vacuum drying, obtaining cellulose derivative;
3) coating of Stationary liquid
By 5g3, the cellulose derivative that 5-dimethylphenyl isocyanate is modified is dissolved in the transparent state of tetrahydrofuran solvent, above-mentioned for 10ml solution is added 17.5g aminopropyl to be modified in hybrid mesoporous silica gel, slow steaming removing oxolane, repeatedly repeat above-mentioned steps until solution of cellulose derivative is all applied complete till, i.e. obtained hybrid mesoporous substrate application type Polysaccharides Type Chiral Stationary Phases.
Claims (7)
1. a method for hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase, is characterized in that, is undertaken by following reactions steps:
(1) preparation of hybrid mesoporous silica gel
Be silicon source with 1,2-bis-(trimethoxy is silica-based) ethane and silane reagent, take surfactant as template, second alcohol and water is mixed solvent, and alkali, as hydrolyst, prepares hybrid mesoporous silica gel, and synthetic route road as shown in Figure 1.
(2) preparation of polysaccharide derivatives
Polysaccharide is placed in the reactor of organic solvent, add the excessive polysaccharide derivatization reagent for modifying, at 80 DEG C, react 24h, reaction system is cooled to room temperature, isolated by filtration, washing, and vacuum drying is for subsequent use;
(3) coating of Stationary liquid
The polysaccharide derivatives of above-mentioned preparation is joined in oxolane, makes it dissolve.Appropriate polysaccharide derivates solution is added in the solvent filling the hybrid mesoporous silica gel that aminopropyl is modified, slow steaming desolventizes, repeatedly repeat above-mentioned steps until polysaccharide derivates solution is all applied complete till, so just obtained hybrid mesoporous silica matrix Polysaccharides Type Chiral Stationary Phases.
2. the method for a kind of hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase according to claim 1, is characterized in that: described polysaccharide is starch, cellulose.
3. the method for a kind of hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase according to claim 1, is characterized in that: polysaccharide derivatization reagent is phenyl isocyanate and derivative thereof and chlorobenzoyl chloride and derivative thereof.
4. the method for a kind of hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase according to claim 1, is characterized in that: the silane reagent synthesizing hybrid mesoporous silica gel is aminopropyl triethoxysilane.
5. the method for a kind of hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase according to claim 1, is characterized in that: hybrid mesoporous Silica Surface and inner aminopropyl load capacity are 0.05-5 μm of ol/m
2.
6. the method for a kind of hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase according to claim 1, is characterized in that: hybrid mesoporous silica gel is spheric granules.
7. the method for a kind of hybrid mesoporous silica matrix coating-type polysaccharide chiral stationary phase according to claim 1, is characterized in that: synthesizing hybrid mesoporous silica gel pattern mould agent is lauryl amine and softex kw mixture.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107456959A (en) * | 2016-06-04 | 2017-12-12 | 中科院大连化学物理研究所淮安化工新材料研究中心 | A kind of coating preparation method of small-bore silica matrix chiral stationary phase |
| CN109529794A (en) * | 2018-12-27 | 2019-03-29 | 中国人民解放军第四军医大学 | Optical pure mandel derivative-Cellulose chiral stationaryphase, preparation method and application |
| CN110003350A (en) * | 2018-01-05 | 2019-07-12 | 中国科学院化学研究所 | Polysaccharide derivates and preparation method thereof and purposes as chiral stationary phase |
| CN111229186A (en) * | 2018-11-29 | 2020-06-05 | 中国科学院大连化学物理研究所 | Chromatographic stationary phase material and preparation method and application thereof |
| CN113680336A (en) * | 2021-08-20 | 2021-11-23 | 华南师范大学 | Cellulose coating type spherical covalent organic framework chiral stationary phase and application thereof |
| CN113908813A (en) * | 2021-10-22 | 2022-01-11 | 浙江大学衢州研究院 | Cellulose derivative-silicon-based hybrid microsphere and preparation method thereof |
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| CN102049245A (en) * | 2009-11-05 | 2011-05-11 | 南开大学 | Method for preparing coating type cellulose derivative chiral monolithic column |
| JP4750303B2 (en) * | 2001-03-23 | 2011-08-17 | 水澤化学工業株式会社 | Mesoporous silica alumina gel, humidity control agent and catalyst support |
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| JP4750303B2 (en) * | 2001-03-23 | 2011-08-17 | 水澤化学工業株式会社 | Mesoporous silica alumina gel, humidity control agent and catalyst support |
| CN102049245A (en) * | 2009-11-05 | 2011-05-11 | 南开大学 | Method for preparing coating type cellulose derivative chiral monolithic column |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107456959A (en) * | 2016-06-04 | 2017-12-12 | 中科院大连化学物理研究所淮安化工新材料研究中心 | A kind of coating preparation method of small-bore silica matrix chiral stationary phase |
| CN110003350A (en) * | 2018-01-05 | 2019-07-12 | 中国科学院化学研究所 | Polysaccharide derivates and preparation method thereof and purposes as chiral stationary phase |
| CN111229186A (en) * | 2018-11-29 | 2020-06-05 | 中国科学院大连化学物理研究所 | Chromatographic stationary phase material and preparation method and application thereof |
| CN109529794A (en) * | 2018-12-27 | 2019-03-29 | 中国人民解放军第四军医大学 | Optical pure mandel derivative-Cellulose chiral stationaryphase, preparation method and application |
| CN109529794B (en) * | 2018-12-27 | 2021-12-17 | 中国人民解放军第四军医大学 | Optical pure mandelic acid derivative-cellulose chiral stationary phase, preparation method and application |
| CN113680336A (en) * | 2021-08-20 | 2021-11-23 | 华南师范大学 | Cellulose coating type spherical covalent organic framework chiral stationary phase and application thereof |
| CN113680336B (en) * | 2021-08-20 | 2024-01-30 | 华南师范大学 | Cellulose coated spherical covalent organic framework chiral stationary phase and application |
| CN113908813A (en) * | 2021-10-22 | 2022-01-11 | 浙江大学衢州研究院 | Cellulose derivative-silicon-based hybrid microsphere and preparation method thereof |
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Application publication date: 20151125 |