CN100392395C - A method for preparing stationary phase of liquid chromatogram of modified zirconia or its composite oxides - Google Patents
A method for preparing stationary phase of liquid chromatogram of modified zirconia or its composite oxides Download PDFInfo
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- CN100392395C CN100392395C CNB2005100192572A CN200510019257A CN100392395C CN 100392395 C CN100392395 C CN 100392395C CN B2005100192572 A CNB2005100192572 A CN B2005100192572A CN 200510019257 A CN200510019257 A CN 200510019257A CN 100392395 C CN100392395 C CN 100392395C
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Abstract
The present invention provides a method for preparing modified zirconia or a fixed phase of a composite oxide of the modified zirconia. Fosfomycin sodium is used as a space group with the method and is adsorbed on the modified zirconia and the composite oxide of the modified zirconia through a Lewis acid and alkali function, and then, organic molecules which can react with amido or a hydroxyl group are selected to further modify the zirconia modifying the fosfomycin sodium and the composite oxide of the modified zirconia so as to prepare different modified zirconia and fixed phases of the composite oxide of the modified zirconia. The course of the preparation method is simple, the Lewis acid center of the zirconia and the surface of the composite oxide can be effectively covered, adsorption is reduced, the method can also be used for preparing the fixed phases synthesizing different functional groups according to separation requirements, and therefore, the method provided by the present invention has wide application.
Description
Technical field
The present invention relates to a kind of method for preparing modified zirconia or its composite oxides liquid chromatography stationary phase, belong to technical field of analytical chemistry.
Background technology
High performance liquid chromatography is one of contemporary most widely used analytical approach and separation means, the preparation that it not only can be used for multiple potpourri separates, and can be used for qualitative and quantitative analysis simultaneously, be widely used in each department of scientific research and the every field of social production.In liquid chromatographic system, the core component of decision analysis result and separation degree quality is chromatographic column.Therefore, the development of novel chromatographic column filler is the important topic that the chromatogram worker pays close attention to always.In modern age liquid chromatography stationary phase, be that the chemically bonded phase packing of matrix accounts for about 80% in the application of whole high performance liquid chromatography with the silica particles.But the chemical stability of silica gel and thermal stability are relatively poor: under alkali condition, silica matrix itself can dissolving, and temperature is when raising, enhanced dissolution rate; Than under the strong acidic condition, the silane generation hydrolysis of bonding, so the silica matrix stationary phase can only use in pH2～8 scopes usually; The silicon hydroxyl on surface also often causes alkali compounds chromatographic peak hangover on silica gel or modified silica-gel post serious.Though can improve its chemical stability to a certain extent and improve its chromatographic performance, but still can not be satisfactory by the whole bag of tricks.In order to overcome the inherent defect of silica matrix stationary phase, people are continually developing new host material.
Summary of the invention
The present invention is exactly that to provide a kind of at the inherent defect that the silica matrix stationary phase exists be the preparation method of the stationary phase of matrix with zirconia or its composite oxides, and the stationary phase by this method preparation not only stable chemical performance but also chromatographic performance is good.
Technical scheme provided by the invention is: at first fosfomycin sodium and mass percent concentration are 25%～28% ammoniacal liquor reaction; Make zirconia or its composite oxides modification with reaction product by Louis (Lewis) acid-base function then, make zirconia or its composite oxides surface after the modification contain hydroxyl and amino, make fosfomycin sodium modified zirconia or its composite oxides liquid chromatography stationary phase; At last according to separate object, selection can be carried out further modification to zirconia or its composite oxides of fosfomycin sodium modification with the organic molecule of amino or hydroxyl reaction, the organism that effect by active amino or hydroxyl will contain various different functional groups is modified on zirconia or its composite oxides matrix, prepares the modified zirconia or its composite oxides liquid chromatography stationary phase that are fit to separate object.
In said method, fosfomycin sodium and ammoniacal liquor are that 1: 1.2～1: 10 ratio is blended under 40～60 ℃ of temperature and reacted 5～12 hours in the amount of substance mol ratio, and reacted mixed solution is neutralized to pH5～6 with hydrochloric acid.Add zirconia or its composite oxides then in this solution, reflux is 8～12 hours under the condition that stirs and feed nitrogen.Gained fosfomycin sodium modified zirconia or its composite oxides are last and can promptly obtain corresponding modified zirconia or its composite oxides stationary phase with the organism reaction of amino or hydroxyl reaction.
Zirconia and modified zirconia are one of more novel chromatograph packing materials of Recent study, and it has the excellent chemical stability of the high mechanical properties and the polymer substrate of silica matrix simultaneously.If strong Louis (Lewis) alkali compounds is adsorbed on zirconia stationary phase surface, not only can effectively shelter Louis (Lewis) acid sites of zirconium surface, the molecular structure that modifier itself is had provides new retention mechanism and separation selectivity for stationary phase.We are by discovering that to preparation, chromatographic performance and Louis (Lewis) the alkali modification zirconia stationary phase of zirconia filler zirconic pore structure shows as the big pore-throat of hole body little " ink ampuliform ", and is undesirable as efficient liquid phase chromatographic stuffing.At the defective of zirconia filler pore structure, we are doped to magnesium oxide, cerium oxide etc. in the zirconia, prepare composite oxides chromatograph packing materials such as magnesium zirconium and cerium zirconium on molecular level.
Therefore, the method for utilizing Louis (Lewis) acid-base function to zirconia or its composite oxides surface modification provided by the invention is the important channel of the different separating property stationary phase of preparation.This method not only preparation process is easy, and effective Louis (Lewis) acid sites on capping oxidation zirconium or its composite oxides surface, reduces absorption.And method provided by the invention also can be used for preparing according to separating the synthetic stationary phase that contains different functional groups of needs.
Embodiment
The method for preparing modified zirconia or its composite oxides liquid chromatography stationary phase provided by the invention comprises two parts, the one, and preparation fosfomycin sodium modified zirconia or its composite oxides; The 2nd, according to separate object, selection can be prepared the modified zirconia or its composite oxides liquid chromatography stationary phase that are fit to separate object with the organic molecule of amino or hydroxyl reaction---carboxylic acid, ester, aldehyde or protein carry out further modification to zirconia or its composite oxides of fosfomycin sodium modification.
The concrete steps that first prepares fosfomycin sodium modified zirconia or its composite oxides are as follows: take by weighing 1.2～1.5g fosfomycin sodium in the 100mL there-necked flask, add 10～20mL mass percent concentration and be 25%～28% strong aqua (is that 1: 1.2～1: 10 ratio is mixed in the amount of substance mol ratio as long as satisfy fosfomycin sodium and ammoniacal liquor), between 40 ℃～60 ℃, added thermal response 5～12 hours.Be that 10%～30% hydrochloric acid is regulated above-mentioned mixed solution to pH5～6 with mass percent concentration then, distilled water diluting to cumulative volume is 60mL, add a kind of in 6～15g zirconia or zirconia-alumina, zirconia magnesium, zirconia cerium, the zirconia calcium composite oxides, magnetic agitation is in N
2In the atmosphere in 100-120 ℃ of oil bath reflux, behind reaction 8～12h, cooling, suction filtration with distilled water washing, obtains the fosfomycin sodium modified zirconia behind 120 ℃ of following vacuum drying 5h or its composite oxides are stand-by.
Because this part all can use in the following embodiments, thus in each embodiment repeated description no longer.
Second portion is according to separate object, selection can be prepared the modified zirconia or its composite oxides liquid chromatography stationary phase that are fit to separate object with the organic molecule of amino or hydroxyl reaction---carboxylic acid, ester, aldehyde or protein carry out further modification to zirconia or its composite oxides of fosfomycin sodium modification.Therefore this part specifies in the following embodiments because of the step that difference adopted of organic molecule is also different.
Embodiment 1:
The preparation of carboxyl acid modified zirconia or its composite oxides stationary phase: earlier with aryl carboxylic acid (as pyrenyl butyric acid, methyl, benzoic acid, paranitrobenzoic acid, 3, the 5-dinitrobenzoic acid) or the reaction of alkyl carboxylic acid (as stearic acid, lauric acid) and thionyl chloride generate acyl chlorides, then with ammonification after fosfomycin sodium modified zirconia or the reaction of its composite oxides obtain various aromatic hydrocarbons and alkane modified zirconia or its composite oxides stationary phase.
Concrete steps are as follows: (1) learns from else's experience pyrenyl butyric acid, methyl, benzoic acid, paranitrobenzoic acid, 3.5-dinitrobenzoic acid or stearic acid, a kind of 0.4～4.0g in the lauric acid of vacuum drying in the 25mL round-bottomed flask, add dry thionyl chloride 5～15mL, oil bath reflux stirring reaction 8～12 hours, decompression distillation, thionyl chloride is all steamed, remaining solid is acyl chlorides, and is stand-by.(2) get 6～15g fosfomycin sodium modified zirconia or its composite oxides in the 100mL there-necked flask, add that drying handles dissolved fully acyl chlorides, the volume numbered is 5～10 times dichloromethane solution of zirconia or its composite oxides quality numbered, splashes into 0.5～2.5mL triethylamine.Reflux is 8～12 hours under the condition that stirs and feed nitrogen, cooling, and suction filtration is used methylene chloride and methanol wash successively, promptly obtains aromatic hydrocarbons or alkyl carboxylic acid modified zirconia or its composite oxides stationary phase.
The separation of fullerene: with on the pyrenyl butyric acid modified zirconia or its composite oxides stationary phase of method for preparing, when being moving phase with Benzene Chloride even carbon disulphide to C
60And C
70Separate, obtained baseline separation, can realize that preparation separates.
Embodiment 2:
The preparation of ester type compound modified zirconia or its composite oxides stationary phase: the naphthalene methyl acetate of the vacuum drying of learning from else's experience, methyl benzoate or ethyl benzoate, methyl p-nitrobenzoate, 3, fosfomycin sodium modified zirconia after a kind of and ammonification in the various ester type compounds such as 5-dinitro-methyl benzoate or chloro-carbonic acid 18 alcohol esters, cholesterol chloro-formiate or the reaction of its composite oxides obtain respective fixation mutually.Concrete steps are as follows: a kind of 0.4～4.0g in the above-mentioned ester of the vacuum drying of learning from else's experience is in the 100mL there-necked flask, with handled, the volume numbered is zirconia or its composite oxides quality numbered 5～10 times dichloromethane solution dissolving, add 6～15g fosfomycin sodium modified zirconia or its composite oxides after the vacuum drying then, splash into 0.5～2.5mL triethylamine.Reflux is 8～24 hours under the condition that stirs and feed nitrogen, cooling, and suction filtration is used methylene chloride, methyl alcohol and washing with acetone successively, promptly obtains ester type compound modified zirconia or its composite oxides stationary phase.As can obtain having the liquid crystal stationary phase of special nature and special-purpose with cholesterol chloro-formiate modified zirconia or its composite oxides.
Embodiment 3
The preparation of aldehyde compound modified zirconia or its composite oxides stationary phase: get a kind of being dissolved in 5～10 times the methanol solution that the volume numbered is zirconia or its composite oxides quality numbered in the various aldehyde compounds such as 0.4～4.0g formaldehyde, glutaraldehyde, naphthylacetaldehyde, benzaldehyde, positive eight aldehyde, fosfomycin sodium modified zirconia or its composite oxides after adding 6～15g ammonification, stir, normal temperature reacts after 8～12 hours down, suction filtration, use methanol wash, obtain various aldehyde compound modified zirconias or its composite oxides stationary phase.
Embodiment 4
The preparation of protein-modified zirconia or its composite oxides stationary phase: (1) takes by weighing 0.5～1.0g glutaraldehyde or 1,1 '-the dicarbapentaborane imidazoles is dissolved in 40～60mL methanol solution, fosfomycin sodium modified zirconia or its composite oxides after adding 6～15g ammonification, stir, normal temperature reacts after 8～12 hours down, suction filtration is used methanol wash, obtains glutaraldehyde modified zirconia or its composite oxides.(2) take by weighing with amino amount of substance ratio be that protein such as 1: 1.2～1: 1.5 bovine serum albumin(BSA) or human serum albumins are dissolved in (pH5-8 in the acetum of 0.01～3.00mol/L triethylamine, the volume numbered is zirconia or its composite oxides quality numbered 5～10 times), with gained glutaraldehyde or 1,1 '-the imidazole modified zirconia of dicarbapentaborane or its composite oxides join in the above-mentioned mixed solution, stir, normal temperature reacts after 8～12 hours down, cooling, suction filtration, (pH7) washing promptly obtains protein-modified zirconia or its composite oxides stationary phase in the acetum with corresponding 0.01～3.00mol/L triethylamine.Can be used for the separation of some enantiomeric compounds.
Claims (4)
1. the preparation method of a modified zirconia or its composite oxides liquid chromatography stationary phase is characterized in that:
At first with fosfomycin sodium and ammoniacal liquor reaction, being about to fosfomycin sodium and mass percent concentration and being 25%～28% ammoniacal liquor is that 1: 1.2～1: 10 ratio is mixed in the amount of substance mol ratio, reacted 5～12 hours under 40～60 ℃ of temperature, reacted mixed solution mass percent concentration is that 10%～30% hydrochloric acid is adjusted to pH5～6; Then reaction product is made zirconia or its composite oxides modification by the Lewis Acids and Bases effect, make zirconia or its composite oxides surface after the modification contain hydroxyl and amino, promptly after fosfomycin sodium and ammoniacal liquor reaction, in the mixed solution of HCl adjusting pH value, add zirconia or its composite oxides again, wherein the mass ratio of fosfomycin sodium and zirconia or its composite oxides is 1: 5～1: 10, reflux is 8～12 hours under the condition that stirs and feed nitrogen, promptly obtains zirconia or its composite oxides of fosfomycin sodium modification; At last according to separate object, selection can be carried out further modification to zirconia or its composite oxides of fosfomycin sodium modification with the organic molecule of amino or hydroxyl reaction, when being carboxylic acid with the organic molecule of amino or hydroxyl reaction, the step that zirconia or its composite oxides of fosfomycin sodium modification are carried out further modification is, it is in 5～10 times the methylene chloride of zirconia or its composite oxides quality numbered at the volume numbered that carboxylic acid reaction is become behind the corresponding acyl chlorides zirconia or its composite oxides with the fosfomycin sodium modification, with the triethylamine is catalyzer, reflux is 8～12 hours under the condition that stirs and feed nitrogen, again through cooling, suction filtration, washing can obtain carboxyl acid modified zirconia or its composite oxides liquid chromatography stationary phase, wherein, the zirconia composite oxides are zirconia-alumina, zirconia magnesium, the zirconia cerium, or zirconia calcium composite oxides.
2. the preparation method of a modified zirconia or its composite oxides liquid chromatography stationary phase is characterized in that:
At first with fosfomycin sodium and ammoniacal liquor reaction, being about to fosfomycin sodium and mass percent concentration and being 25%～28% ammoniacal liquor is that 1: 1.2～1: 10 ratio is mixed in the amount of substance mol ratio, reacted 5～12 hours under 40～60 ℃ of temperature, reacted mixed solution mass percent concentration is that 10%～30% hydrochloric acid is adjusted to pH5～6; Then reaction product is made zirconia or its composite oxides modification by the Lewis Acids and Bases effect, make zirconia or its composite oxides surface after the modification contain hydroxyl and amino, promptly after fosfomycin sodium and ammoniacal liquor reaction, in the mixed solution of HCl adjusting pH value, add zirconia or its composite oxides again, wherein the mass ratio of fosfomycin sodium and zirconia or its composite oxides is 1: 5～1: 10, reflux is 8～12 hours under the condition that stirs and feed nitrogen, promptly obtains zirconia or its composite oxides of fosfomycin sodium modification; At last according to separate object, selection can be carried out further modification to zirconia or its composite oxides of fosfomycin sodium modification with the organic molecule of amino or hydroxyl reaction, when being ester with the organic molecule of amino or hydroxyl reaction, the step that zirconia or its composite oxides of fosfomycin sodium modification are carried out further modification is, is in 5～10 times the methylene chloride of zirconia or its composite oxides quality numbered with zirconia or its composite oxides of ester and fosfomycin sodium modification at the volume numbered, with the triethylamine is catalyzer, reflux is 8～24 hours under the condition that stirs and feed nitrogen, again through cooling, suction filtration, washing can obtain ester modified zirconia or its composite oxides liquid chromatography stationary phase, wherein, the zirconia composite oxides are zirconia-alumina, zirconia magnesium, the zirconia cerium, or zirconia calcium composite oxides.
3. the preparation method of a modified zirconia or its composite oxides liquid chromatography stationary phase is characterized in that:
At first with fosfomycin sodium and ammoniacal liquor reaction, being about to fosfomycin sodium and mass percent concentration and being 25%～28% ammoniacal liquor is that 1: 1.2～1: 10 ratio is mixed in the amount of substance mol ratio, reacted 5～12 hours under 40～60 ℃ of temperature, reacted mixed solution mass percent concentration is that 10%～30% hydrochloric acid is adjusted to pH5～6; Then reaction product is made zirconia or its composite oxides modification by the Lewis Acids and Bases effect, make zirconia or its composite oxides surface after the modification contain hydroxyl and amino, promptly after fosfomycin sodium and ammoniacal liquor reaction, in the mixed solution of HCl adjusting pH value, add zirconia or its composite oxides again, wherein the mass ratio of fosfomycin sodium and zirconia or its composite oxides is 1: 5～1: 10, reflux is 8～12 hours under the condition that stirs and feed nitrogen, promptly obtains zirconia or its composite oxides of fosfomycin sodium modification; At last according to separate object, selection can be carried out further modification to zirconia or its composite oxides of fosfomycin sodium modification with the organic molecule of amino or hydroxyl reaction, when being aldehyde with the organic molecule of amino or hydroxyl reaction, the step that zirconia or its composite oxides of fosfomycin sodium modification are carried out further modification is, is in 5～10 times the methyl alcohol of zirconia or its composite oxides quality numbered with zirconia or its composite oxides of aldehyde and fosfomycin sodium modification at the volume numbered, normal temperature reacted 8～12 hours down, suction filtration, washing promptly obtains aldehyde modified zirconia or its composite oxides liquid chromatography stationary phase, wherein, the zirconia composite oxides are zirconia-alumina, zirconia magnesium, the zirconia cerium, or zirconia calcium composite oxides.
4. the preparation method of a modified zirconia or its composite oxides liquid chromatography stationary phase is characterized in that:
At first with fosfomycin sodium and ammoniacal liquor reaction, being about to fosfomycin sodium and mass percent concentration and being 25%～28% ammoniacal liquor is that 1: 1.2～1: 10 ratio is mixed in the amount of substance mol ratio, reacted 5～12 hours under 40～60 ℃ of temperature, reacted mixed solution mass percent concentration is that 10%～30% hydrochloric acid is adjusted to pH5～6; Then reaction product is made zirconia or its composite oxides modification by the Lewis Acids and Bases effect, make zirconia or its composite oxides surface after the modification contain hydroxyl and amino, promptly after fosfomycin sodium and ammoniacal liquor reaction, in the mixed solution of HCl adjusting pH value, add zirconia or its composite oxides again, wherein the mass ratio of fosfomycin sodium and zirconia or its composite oxides is 1: 5～1: 10, reflux is 8～12 hours under the condition that stirs and feed nitrogen, promptly obtains zirconia or its composite oxides of fosfomycin sodium modification; At last according to separate object, selection can be carried out further modification to zirconia or its composite oxides of fosfomycin sodium modification with the organic molecule of amino or hydroxyl reaction, when being protein with the organic molecule of amino or hydroxyl reaction, the step that zirconia or its composite oxides of fosfomycin sodium modification are carried out further modification is, at first with glutaraldehyde or 1, the zirconia of 1 '-dicarbapentaborane imidazoles and fosfomycin sodium modification or its composite oxides are in 5～10 times the absolute methanol of zirconia or its composite oxides quality numbered at the volume numbered, normal temperature reacted 8～12 hours down, suction filtration, washing obtains glutaraldehyde or 1, the imidazole modified zirconia of 1 '-dicarbapentaborane or its composite oxides liquid chromatography stationary phase, then with this stationary phase and with the amount of substance ratio of amino be that 1: 1.2～1: 1.5 protein is zirconia or its composite oxides quality numbered 5～10 times at the volume numbered, concentration is 0.01～3.00mol/L, the pH value is to mix in triethylamine-hac buffer of 5～8, reacted at normal temperatures 8～12 hours, suction filtration, washing promptly obtains protein-modified zirconia or its composite oxides liquid chromatography stationary phase, wherein, the zirconia composite oxides are zirconia, zirconia-alumina, zirconia magnesium, the zirconia cerium, or zirconia calcium composite oxides.
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| US5141634A (en) * | 1988-02-03 | 1992-08-25 | Regents Of The University Of Minnesota | High stability porous zirconium oxide spherules |
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| CN1166946C (en) * | 1998-12-08 | 2004-09-15 | 武汉大学 | Modified mixed Zr-Mg gel with fixed liquid-phase chromatic spectrum and its preparation |
| US6846410B2 (en) * | 2002-05-03 | 2005-01-25 | Zirchrom Separations, Inc. | High stability porous metal oxide spherules used for one-step antibody purifications |
-
2005
- 2005-08-08 CN CNB2005100192572A patent/CN100392395C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5141634A (en) * | 1988-02-03 | 1992-08-25 | Regents Of The University Of Minnesota | High stability porous zirconium oxide spherules |
| US5346619A (en) * | 1990-03-22 | 1994-09-13 | Regents Of The University Of Minnesota | Carbon-clad zirconium oxide particles |
| CN1166946C (en) * | 1998-12-08 | 2004-09-15 | 武汉大学 | Modified mixed Zr-Mg gel with fixed liquid-phase chromatic spectrum and its preparation |
| US6846410B2 (en) * | 2002-05-03 | 2005-01-25 | Zirchrom Separations, Inc. | High stability porous metal oxide spherules used for one-step antibody purifications |
Non-Patent Citations (8)
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| "Lewis碱改性氧化锆基质色谱固定相的研究进展". 胡玉玲等.色谱，第23卷第3期. 2005 |
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