CN104841164B - Organic-silica gel hybridization integral post that hexadecene-sodium vinyl sulfonate is modified - Google Patents
Organic-silica gel hybridization integral post that hexadecene-sodium vinyl sulfonate is modified Download PDFInfo
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Abstract
The invention discloses organic silica gel hydridization integral post and application thereof that a kind of hexadecene sodium vinyl sulfonate is modified, described organic silica gel hydridization integral post is to make through pretreatment and one kettle way.It is complicated loaded down with trivial details that organic silica gel hydridization integral post of the present invention had both eliminated tradition packed column filling operation, sintering stopper is easily generated the problems such as bubble, overcome again open tubular column capacity low with compare little shortcoming, gained organic silica gel hydridization integral post is by the organic blended pliability adding monolithic silica column, and the sulfonate radical that contains of hexadecene sodium vinyl sulfonate can provide certain EOF, the integral post making synthesis can carry out chromatographic isolation under pCEC pattern, and promote the ion exchange in chromatographic separation process, its stable in properties, favorable reproducibility, can use in the range of wider pH, and its EOF size can be controlled by the pH of regulation flowing phase, to benzene series, naphthalene series compound and amino benzenes compounds have preferable separating effect.
Description
Technical field
The invention belongs to capillary chromatographic column technical field, be specifically related to organic-silica gel hybridization integral post of a kind of hexadecene-sodium vinyl sulfonate modification and its preparation method and application.
Background technology
Capillary electric chromatogram is the one in recent years grown up on the basis of electrophoretic techniques and high-efficient liquid phase chromatogram technology novel Micro-Column Separation method efficient, quick.As the important component part of electrochromatography isolation technics, CEC post can be divided into open tubular column, packed column and integral post.Capillary monolithic column overcomes open tubular column and compares the shortcoming of deficiency, avoids packed column simultaneously and need to make the step of stopper, has and prepares simple, good penetrability, post effect advantages of higher.
One kettle way is a kind of method preparing the hydridization integral post with active function groups based on simple sol-gel process, it is in the reaction mixture after organic functions monomer is added directly into hydrolysis, carrying out heat treated again, organic functions monomer is carried out with the polycondensation reaction between the activity on prepolymerized siloxanes simultaneously in the process.By one kettle way, a step can make pillar, and the retention of prepared hydridization integral post can be changed by changing organic functions monomer, eliminate the loaded down with trivial details of post-column derivation.
Organic-silica gel hybridization integral post that the hexadecene of the present invention-sodium vinyl sulfonate is modified, due to by the organic blended pliability increasing monolithic silica column, and the sulfonate radical that hexadecene-sodium vinyl sulfonate contains can provide certain EOF, the integral post making synthesis can carry out chromatographic isolation under pCEC pattern, simultaneously facilitate the generation of chromatographic separation process intermediate ion exchange interaction, improve separating property.Use organic-silica gel hybridization integral post technology that hexadecene-sodium vinyl sulfonate is modified, both eliminate complicated loaded down with trivial details, the sintering stopper of tradition packed column filling operation and be easily caused the problems such as bubble generation, overcome again open tubular column capacity low with compare little shortcoming, have a good application prospect.
Summary of the invention
It is an object of the invention to provide organic-silica gel hybridization integral post and application thereof that a kind of hexadecene-sodium vinyl sulfonate is modified, organic-silica gel hybridization integral post stable chemical nature that this hexadecene-sodium vinyl sulfonate is modified, more action site is had with sample, benzene series, naphthalene series compound and amino benzenes compounds are respectively provided with good separating effect, and favorable reproducibility.
For achieving the above object, the present invention adopts the following technical scheme that
Organic-silica gel hybridization integral post that a kind of hexadecene-sodium vinyl sulfonate is modified is that the pretreatment through capillary tube, one kettle way are prepared from.
Its preparation method specifically includes following steps:
(1) by capillary column successively with 1mol/L HCl and H2O rinses 30 min respectively, then rinses 30 min with NaOH, heats 3 h, then use H successively at 100 DEG C2O、0.1mol/L HCl、H2O and methanol rinse 30 min respectively, and finally at 180 DEG C, logical nitrogen dries up, standby；
(2) 270mg Polyethylene Glycol (PEG), 100mg urea are accurately weighed, it is dissolved in the acetum of 2.5mL 0.01 mol/L, until completely dissolved, add 1mL methyl silicate (TMOS) and pre-polymer solution that VTES (VTEO) forms, stirring reaction 1h at 0 DEG C, form the hydrolyzed solution of homogeneous transparent, containing 900 μ L TMOS and 300 μ L VTEO in described pre-polymer solution；The most accurately weighing 40 mg hexadecenes and 40mg sodium vinyl sulfonate and 4mg azodiisobutyronitrile (AIBN), join in 1 mL said hydrolyzed liquid, ice-bath ultrasonic processes 10 min and dissolves degassing；
(3) being manually pushed back in pretreated capillary tube by the mixed solution of step (2) with syringe, capillary tube two ends, with the 1/2 ~ 2/3 of capillary tube overall length for degree, are all sealed by the amount of pushing with rubber；Put into reacting by heating 12 h in 45 ~ 50 DEG C of water-baths, then temperature is brought up to 60 DEG C of continuation heating 12h, finally rinse to remove solvent and other solvable residue by the hydridization integral post water obtained.
Organic-silica gel hybridization integral post that described hexadecene-sodium vinyl sulfonate is modified is applicable to separate benzene series, naphthalene series compound and amino benzenes compounds.
The remarkable advantage of the present invention is:
(1) organic-silica gel hybridization integral post that the hexadecene of the present invention-sodium vinyl sulfonate is modified, by organic blended hexadecene, add pliability and the hydrophobicity of monolithic silica column, and the sulfonate radical that sodium vinyl sulfonate contains can provide certain EOF, the integral post making synthesis can carry out chromatographic isolation under pCEC pattern, simultaneously facilitate the generation of ion exchange in chromatographic separation process, separating effect can be improved.
(2) organic-silica gel hybridization integral post that hexadecene of the present invention-sodium vinyl sulfonate is modified both can exempt tradition packed column filling operation complexity, sintering stopper is easily caused the problems such as bubble generation, overcome again open tubular column capacity low with compare little shortcoming, its stable in properties, the advantage of favorable reproducibility, is respectively provided with good separating effect to benzene series, naphthalene series compound and amino benzenes compounds.
Accompanying drawing explanation
Fig. 1 is the impact on organic-silica gel hybridization rod structure that hexadecene-sodium vinyl sulfonate is modified of the different urea content.Wherein, (A) 50 mg urea；(B) 100 mg urea；(C) 150 mg urea；(D) 250 mg urea.
Fig. 2 is the different ethane nitrile content impacts on EOF in flowing mutually.
Fig. 3 is the impact that in flowing mutually, benzene-like compounds is separated by different ethane nitrile contents.Wherein, 0 is thiourea, and 1 is toluene, and 2 is ethylbenzene, and 3 is propyl benzene, and 4 is butylbenzene, and 5 is penta benzene.
Fig. 4 is the impact that in flowing mutually, amino benzenes compounds is separated by different ethane nitrile contents.Wherein, 0 is thiourea；1 is p-phenylenediamine；2 is o-phenylenediamine；3 is benzidine；4 is alpha naphthylamine.
Fig. 5 is the impact that in flowing mutually, benzene series, naphthalene series compound are separated by different ethane nitrile contents.Wherein, 0 is thiourea；1 is benzene；2 is naphthalene.
Detailed description of the invention
In order to make content of the present invention easily facilitate understanding, below in conjunction with detailed description of the invention, technical solutions according to the invention are described further, but the present invention is not limited only to this.
1. the different urea content impacts on EOF in organic-silica gel hybridization integral post that hexadecene-sodium vinyl sulfonate is modified.
Respectively 50,100,150, the urea of 250mg and 270mg PEG are dissolved in 2.5mL 0.01 mol/L acetum, until completely dissolved, add 1mL methyl silicate (TMOS) and pre-polymer solution that VTES (VTEO) forms, stirring reaction 1h at 0 DEG C, form the hydrolyzed solution of homogeneous transparent, wherein, containing 900 μ L TMOS and 300 μ L VTEO in pre-polymer solution；The most accurately weighing 40 mg hexadecenes and 40mg sodium vinyl sulfonate and 4 mg AIBN, join in 1 mL said hydrolyzed liquid, ice-bath ultrasonic processes 10 min and dissolves degassing.
Respectively above-mentioned mixed solution is manually pushed back into pretreated capillary tube with syringe to 25cm(capillary tube overall length 45cm), capillary tube two ends are all sealed with rubber, put into reacting by heating 12 h in 47 DEG C of water-baths, temperature is brought up to 60 DEG C again and continues heating 12 h, rinse with secondary water, obtain organic-silica gel hybridization integral post that hexadecene-sodium vinyl sulfonate is modified.
The Electronic Speculum shape appearance figure of organic-silica gel hybridization integral post that hexadecene-sodium vinyl sulfonate that different urea consumptions obtain is modified is shown in Fig. 1.
The preparation method of organic-silica gel hybridization integral post that a kind of hexadecene-sodium vinyl sulfonate is modified specifically includes following steps:
(1) by capillary column successively with 1mol/L HCl and H2O rinses 30 min respectively, then rinses 30 min with NaOH, heats 3 h, then use H successively at 100 DEG C2O、0.1mol/L HCl、H2O and methanol rinse 30 min respectively, and finally at 180 DEG C, logical nitrogen dries up, standby；
(2) 270mg PEG, 100mg urea is accurately weighed, it is dissolved in the acetum of 2.5mL 0.01 mol/L, until completely dissolved, add 1mL methyl silicate (TMOS) and pre-polymer solution that VTES (VTEO) forms, stirring reaction 1h at 0 DEG C, form the hydrolyzed solution of homogeneous transparent, wherein, containing 900 μ L TMOS and 300 μ L VTEO in pre-polymer solution；The most accurately weighing 40 mg hexadecenes and 40mg sodium vinyl sulfonate and 4mg AIBN, join in 1 mL said hydrolyzed liquid, ice-bath ultrasonic processes 10 min and dissolves degassing；
(3) with syringe, the mixed solution of step (2) is manually pushed back into pretreated capillary tube to 25cm(capillary tube overall length 45cm, internal diameter 75 μm), capillary tube two ends are all sealed with rubber；Put into reacting by heating 12 h in 47 DEG C of water-baths, then temperature is brought up to 60 DEG C of continuation heating 12h, finally rinse to remove solvent and other solvable residue by the hydridization integral post water obtained.
2. the different ethane nitrile content impacts on EOF in flowing mutually.
Organic-silica gel hybridization integral post that hexadecene prepared by Application Example-sodium vinyl sulfonate is modified, by phosphoric acid triethylamine buffer (pH 4.0,10.0 mmol/L) mix as flowing phase with acetonitrile by different proportion, in making flowing mutually, ethane nitrile content is respectively 5%, 10%, 15%, 20%, 30%, separation voltage-10 kV, detects wavelength 214 nm, flow velocity 0.1 mL/min, pressure 0.7 MPa, investigates the different ethane nitrile content impacts on EOF, its result such as Fig. 2 in flowing mutually.
3. the impact that in flowing mutually, benzene compounds is separated by different ethane nitrile contents.
Organic-silica gel hybridization integral post that hexadecene prepared by Application Example-sodium vinyl sulfonate is modified, by phosphoric acid triethylamine buffer (pH 7.0, 10.0 mmol/L) mix as flowing phase with acetonitrile by different proportion, in making flowing mutually, ethane nitrile content is respectively 20%, 25%, 30%, separation voltage-10 kV, detection wavelength 214 nm, flow velocity 0.1 mL/min, pressure 0.7 MPa, with thiourea as label, benzene-like compounds is detected, its chromatographic results such as Fig. 3, wherein, 0 is thiourea, 1 is toluene, 2 is ethylbenzene, 3 is propyl benzene, 4 is butylbenzene, 5 is penta benzene.
From the figure 3, it may be seen that toluene, ethylbenzene, propyl benzene, butylbenzene, penta benzene go out peak successively according to its hydrophobicity size, show that this post has hydrophobicity and shows typical anti-phase retention mechanism.
4. the impact that in flowing mutually, amino benzenes compounds is separated by different ethane nitrile contents.
Organic-silica gel hybridization integral post that hexadecene prepared by Application Example-sodium vinyl sulfonate is modified, by phosphoric acid triethylamine buffer (pH 4.0,1.0 mmol/L) mix as flowing phase with acetonitrile by different proportion, in making flowing mutually, ethane nitrile content is respectively 5%, 10%, 15%, separation voltage-10 kV, detection wavelength 214 nm, flow velocity 0.1 mL/min, pressure 0.7 MPa, amino benzenes compounds is detected, its chromatographic results such as Fig. 4, wherein, 0 is thiourea, 1 is p-phenylenediamine, 2 is o-phenylenediamine, and 3 is benzidine, and 4 is alpha naphthylamine.
As shown in Figure 4, four kinds of aniline shorten along with the increase of ethane nitrile content, appearance time, show that this post, due to the existence of sulfonate ion, shows weak cation exchange.
5. the impact that in flowing mutually, naphthalene compounds is separated by different ethane nitrile contents.
Organic-silica gel hybridization integral post that hexadecene prepared by Application Example-sodium vinyl sulfonate is modified, just phosphoric acid triethylamine buffer (pH 7.0,10.0 mmol/L) mix as flowing phase with acetonitrile by different proportion, in making flowing mutually, ethane nitrile content is respectively 10%, 15%, 20%, 25%, separation voltage-10 kV, detects wavelength 214 nm, flow velocity 0.1 mL/min, pressure 0.7 MPa, detects naphthalene compounds, its chromatographic results such as Fig. 5, wherein, 0 is thiourea, and 1 is benzene, and 2 is naphthalene.
As shown in Figure 5, along with the minimizing of ethane nitrile content, three kinds of materials can separate well, shows that this post has hydrophobicity and shows typical anti-phase retention mechanism.
The foregoing is only presently preferred embodiments of the present invention, all impartial changes done according to scope of the present invention patent and modification, all should belong to the covering scope of the present invention.
Claims (2)
1. organic-silica gel hybridization integral post that a hexadecene-sodium vinyl sulfonate is modified, it is characterised in that: described organic-silica gel hybridization integral post is that the pretreatment through capillary tube, one kettle way are prepared from；
Its preparation method specifically includes following steps:
(1) by capillary column successively with 1mol/L HCl and H2O rinses 30 min respectively, then rinses 30 min with NaOH, heats 3 h, then use H successively at 100 DEG C2O、0.1mol/L HCl、H2O and methanol rinse 30 min respectively, and finally at 180 DEG C, logical nitrogen dries up, standby；
(2) 270mg PEG, 100mg urea is accurately weighed, it is dissolved in the acetum of 2.5mL 0.01 mol/L, until completely dissolved, add the pre-polymer solution of 1mL TMOS and VTEO composition, stirring reaction 1h at 0 DEG C, form the hydrolyzed solution of homogeneous transparent, containing 900 μ L TMOS and 300 μ L VTEO in described pre-polymer solution；The most accurately weighing 40 mg hexadecenes and 40mg sodium vinyl sulfonate and 4mg AIBN, join in 1 mL said hydrolyzed liquid, ice-bath ultrasonic processes 10 min and dissolves degassing；
(3) being manually pushed back in pretreated capillary tube by the mixed solution of step (2) with syringe, capillary tube two ends, with the 1/2 ~ 2/3 of capillary tube overall length for degree, are all sealed by the amount of pushing with rubber；Put into reacting by heating 12 h in 45 ~ 50 DEG C of water-baths, then temperature is brought up to 60 DEG C of continuation heating 12h, finally rinse to remove solvent and other solvable residue by the hydridization integral post water obtained.
2. the application of the organic-silica gel hybridization integral post of hexadecene as claimed in claim 1-sodium vinyl sulfonate modification, it is characterised in that: organic-silica gel hybridization integral post that described hexadecene-sodium vinyl sulfonate is modified is used for separating benzene series, naphthalene series compound and amino benzenes compounds.
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