CN113063884A - Liquid chromatography column composite packing and application thereof - Google Patents
Liquid chromatography column composite packing and application thereof Download PDFInfo
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- CN113063884A CN113063884A CN202110353538.0A CN202110353538A CN113063884A CN 113063884 A CN113063884 A CN 113063884A CN 202110353538 A CN202110353538 A CN 202110353538A CN 113063884 A CN113063884 A CN 113063884A
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Abstract
The invention relates to the technical field of pharmaceutical analysis, in particular to a liquid chromatography column composite filler. The composite filler comprises an octadecylsilane chemically bonded silica filler and a naloxone chemically bonded silica filler, wherein the mass ratio of the octadecylsilane chemically bonded silica to the naloxone chemically bonded silica filler is 1:2-3, and the preparation method of the chromatographic column comprises the steps of mixing the octadecylsilane chemically bonded silica and the naloxone chemically bonded silica in an organic solvent, performing ultrasonic treatment, and filling the mixture into a liquid chromatographic column. The prepared chromatographic column can simultaneously separate and detect hydrophilic components such as acidic components and alkaline components and lipophilic components, and has the advantages of good separation degree, high column efficiency and short detection time.
Description
Technical Field
The invention relates to the technical field of pharmaceutical analysis, in particular to a liquid chromatography column composite filler and a preparation method thereof.
Background
The high performance liquid chromatography is one of the separation and analysis technologies which are developed fastest and applied most widely at present, and plays an increasingly important role in the fields of medicine analysis, life science, environmental monitoring and the like. The performance of chromatographic packing, which is one of the cores separated by liquid chromatography, directly affects the final result of the separation analysis. However, in the case of a complicated sample, particularly, a single column containing a hydrophilic component, a nonpolar component and an acidic component at the same time, it is difficult to satisfy the requirements for separation and column applicability.
Most of the traditional Chinese medicine extractions adopt water as a solvent, the extract contains a large amount of hydrophilic components, wherein no part of the hydrophilic components contains components with strong acidity, such as a hawthorn extracting solution contains a large amount of acidic components such as citric acid, malic acid and flavonoids, a honeysuckle extracting solution contains main active components such as chlorogenic acid, isochlorogenic acid and caffeic acid, and an angelica extracting solution contains acidic components such as succinic acid, ferulic acid and leucovorin. Therefore, the chromatographic packing which can separate a plurality of components with different properties such as hydrophilicity, lipophilicity, acidity, alkalinity and the like in the same chromatographic column is developed, and has potential social value.
Although the multidimensional chromatography technology can meet the requirements of people on resolution, the multidimensional chromatography system has the problems of complex operation, expensive equipment, poor mobile phase compatibility and the like, cannot meet the requirements of analysis and detection of small and medium-sized enterprises, and is difficult to popularize.
The Chinese patent CN101721980B discloses a liquid chromatographic column mixed packing and a chromatographic column, which comprises long-chain alkyl dimethylsilane bonded silica gel and amidosilane bonded silica gel, the weight ratio of the long-chain alkyl dimethylsilane bonded silica gel to the amidosilane bonded silica gel is 10:1-1:10, the average particle size difference is within +/-20 percent, the specific gravity difference is within +/-20 percent, the liquid chromatographic column mixed packing is applied to chromatographic separation under the condition of mixed mobile phase containing acetonitrile and aqueous solution, and the separation application is the chromatographic separation and detection of samples containing compounds with strong hydrophilicity and compounds with strong lipophilicity. However, this chromatographic packing is not ideal in the effect of separating acidic and basic components and cannot separate highly acidic components.
Chinese patent CN209416990U discloses a composite chromatographic column, which comprises a column body, wherein the column body is divided into an upper section and a lower section, the filler used in the upper section is a filler with a naphthyl group bonded on the surface of a microsphere, and the filler used in the lower section is a filler with a benzenesulfonic group bonded on the surface of the microsphere. The composite chromatographic column has good analysis effect. The utility model also discloses a two-dimentional liquid chromatography system, with compound chromatographic column still includes the extraction column in addition as the analytical column, the filler of extraction column has bonded carboxylic group's filler for the microballon surface. The composite liquid chromatography system can realize the simultaneous separation of four psychotropic drugs. The chromatographic column mainly has good separation effect on aromatic compounds and poor separation effect on other alkane nonpolar components.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the liquid chromatographic column composite filler which is simple to prepare, can simultaneously separate various components with different properties such as hydrophilicity, lipophilicity, acidity, alkalinity and the like, and has the advantages of good separation degree, high column efficiency, short separation time and strong acid and alkali resistance.
The purpose of the invention is realized by the following technical scheme:
the composite filler for the liquid chromatography column comprises an octadecylsilane chemically bonded silica filler and a naloxone chemically bonded silica filler.
Preferably, the mass ratio of the octadecylsilane chemically bonded silica filler to the naloxone chemically bonded silica filler is 1: 2-3.
Preferably, the particle size of the octadecylsilane bonded silica filler and naloxone bonded silica filler is 3 to 5 μm.
Preferably, the preparation method of the naloxone-bonded silica gel filler comprises the following steps:
(1) activating the silicon spheres to obtain activated silicon spheres;
(2) then reacting triethoxysilane to the surface of the activated silicon spheres to form a silicon-hydrogen bond, thereby obtaining modified silica gel;
(3) adding naloxone into the modified silica gel, adding an organic solvent and an isopropanol solution of chloroplatinic acid, stirring, heating and refluxing for 8-10h, washing and drying to obtain the nano-composite material.
More preferably, the step (1) operation comprises: the operation of the step (1) comprises the following steps: adding the silicon spheres into hydrochloric acid, reacting for 2-3h, and drying to obtain activated silicon spheres for later use.
Preferably, the reaction in the step (2) is to sequentially add dioxane, 2mol/L hydrochloric acid and 1mol/L triethoxysilane into the activated silicon spheres, heat reflux for 12-15h, wash with 30% acetone water solution and dioxane, and dry to obtain the product; preferably, the mass molar ratio of the activated silicon spheres to the triethoxysilane in the reaction is 1: 0.005-0.006 g/mol; the mass-volume ratio of the activated silica gel to the dioxane added in the reaction is 1: 23-25 g/ml; the drying temperature is 110-130 ℃.
Preferably, the mass molar ratio of the modified silica gel to the naloxone in the step (3) is 1: 5-8g/mol, wherein the organic solvent is chloroform, and the molar ratio of chloroplatinic acid to naloxone is 10-6-10-5: 1; the mass volume ratio of the modified silica gel to the trichloromethane is 1: 25-45 g/mL.
Preferably, the washing in step (3) is washing with acetone and dichloromethane in sequence, and then washing with dichloromethane and acetone in sequence.
Wherein the structural formula of naloxone is:
the silicon-hydrogen bond of the modified silica gel in the step (3) and the olefin bond of the naloxone are subjected to addition reaction under the conditions, and the naloxone molecule is bonded to the modified silica gel; through a great deal of research, the naloxone bonded silica gel is found to have good separation of nonpolar and polar components and good acid resistance of the filler from a plurality of compounds.
The invention also aims to provide a chromatographic column prepared by the composite filler, and the preparation method of the chromatographic column comprises the steps of mixing octadecylsilane chemically bonded silica and naloxone chemically bonded silica in an organic solvent, performing ultrasonic treatment, and filling the mixture into a liquid chromatographic column;
preferably, the organic solvent is one or more of acetone, tetrahydrofuran, polyethylene glycol and carbon tetrachloride; the ultrasonic power is 200-500W, and the ultrasonic time is 20-40 min.
It is still another object of the present invention to provide the use of the above chromatographic packing/chromatographic column composite packing in analytical detection of compositions containing both hydrophilic, lipophilic and acidic and basic components.
The invention has the beneficial effects that:
the chromatographic column prepared by the invention can simultaneously separate and detect hydrophilic, acidic and weak polar components, and has the advantages of good separation degree, high column efficiency and short detection time. Compared with the traditional detection and analysis method adopting a plurality of chromatographic columns, the method is simple and efficient, and can save a large amount of organic reagents and analysis time.
According to a great deal of research, the prepared naloxone bonded silica gel is excellent in acid and alkali resistance, contains groups with good hydrophilicity such as phenolic hydroxyl group, alcoholic hydroxyl group and ether group in naloxone, and can be separated well at the pH of 1-10 through organic compatibility with other non-polar groups and octadecyl bonded silica gel filler. The chromatographic column obtained by mixing the compound with octadecyl bonded silica gel in a specific ratio can well separate polar and nonpolar components, has good peak shape, no tailing and high column efficiency in the analysis of acidic and basic components, well solves the problem that multiple properties of medicinal components in the compound composition need multiple chromatographic columns for analysis and detection, and has the advantages of short time consumption, strong acid and alkali resistance and sensitive analysis.
Drawings
FIG. 1-1 is a chromatogram obtained by analysis using the column prepared in example 1, wherein 1 is citric acid, 2 is oxymatrine, 3 is matrine, and 4 is pentylbenzene;
fig. 1-2 is an enlarged view of a part of a chromatogram obtained by column analysis using the method prepared in example 1, wherein 1 is citric acid, 2 is oxymatrine, 3 is matrine, and 4 is pentylbenzene;
FIG. 2-1 is a chromatogram obtained by analysis using the column prepared in example 2, wherein 1 is citric acid, 2 is oxymatrine, 3 is matrine, and 4 is pentylbenzene;
FIG. 2-2 is an enlarged view of a part of a chromatogram obtained by column analysis using the method prepared in example 2, wherein 1 is citric acid, 2 is oxymatrine, 3 is matrine, and 4 is pentylbenzene;
FIG. 3-1 is a chromatogram obtained by analysis using the column prepared in example 3, wherein 1 is citric acid, 2 is matrine, 3 is oxymatrine, and 4 is pentylbenzene;
FIG. 3-2 is an enlarged view of a part of a chromatogram obtained by column analysis using the method prepared in example 3, wherein 1 is citric acid, 2 is matrine, 3 is oxymatrine, and 4 is pentylbenzene;
FIG. 4-1 is a chromatogram obtained by analysis using the column prepared in comparative example 1, where 1 is citric acid, 2 is pentylbenzene, 3 is matrine, and 4 is oxymatrine;
FIG. 4-2 is an enlarged view of a part of a chromatogram obtained by column analysis using the method of comparative example 1, wherein 1 is citric acid, 2 is pentylbenzene, 3 is matrine, and 4 is oxymatrine;
FIG. 5 is a chromatogram obtained by analysis using the column prepared in comparative example 2, wherein 1 is citric acid, 2 is oxymatrine, 3 is matrine, and 4 is pentylbenzene;
FIG. 6 is a chromatogram obtained by analysis using the column prepared in comparative example 3, wherein 1 is citric acid, 2 is oxymatrine, 3 is matrine, and 4 is pentylbenzene.
Detailed Description
The technical solution of the present invention is further illustrated by the following examples.
Example 1
(1) Adding 25 parts of 1mol/L hydrochloric acid into 1 part of silicon spheres (with an average particle size of 5 μm, Fuji, Japan), stirring at 90 deg.C for reaction for 2h, filtering, washing with ultrapure water to neutrality, and vacuum drying at 120 deg.C to obtain activated silicon spheres;
(2) adding dioxane into the activated silicon spheres (the mass-volume ratio of the activated silicon spheres to the added dioxane is 1: 23g/ml), slowly dropwise adding 2mol/L HC L, heating to 80 ℃, then slowly dropwise adding 1mol/L dioxane solution of triethoxysilane, heating and refluxing for 12h, after the system is drained, washing with 30% acetone aqueous solution and dioxane, and drying at 120 ℃ to obtain modified silicon spheres, wherein the mass-mole ratio of the activated silicon spheres to the triethoxysilane is 1: 0.006 g/mol.
(3) And sequentially adding trichloromethane, naloxone and 2% isopropanol solution of chloroplatinic acid into the modified silica gel, magnetically stirring, heating and refluxing for 8h, filtering, sequentially washing a filter cake with acetone and dichloromethane, sequentially washing with dichloromethane and acetone, and drying at 110 ℃ to obtain the naloxone bonded silica gel. Wherein the mass molar ratio of the modified silica gel to the naloxone is 1: 5g/mol of chloroplatinic acid with naloxone as reaction substrateThe molar ratio is 10-6: 1; the mass volume ratio of the modified silica gel to the trichloromethane is 1: 25 g/mL;
(4) and (3) carrying out ultrasonic treatment on 1 part of octadecyl bonded silica gel and 2.5 parts of naloxone bonded silica gel prepared in the step (2) in 150 parts of carbon tetrachloride solvent at 200W for 40min to prepare a mixed solution, and filling the mixed solution into a chromatographic column with the size of 4.6mm multiplied by 150 mm.
The octadecyl bonded silica gel is purchased from New Material Co, Ltd, of the family Rigaceae, and is named Fuji Chromatorex filler, the product number is 112926-00-8, and the particle size is 3 μm.
Example 2
(1) Adding 25 parts of 1mol/L hydrochloric acid into 1 part of silicon spheres (with an average particle size of 5 μm, Fuji, Japan), stirring at 90 deg.C for reaction for 2h, filtering, washing with ultrapure water to neutrality, and vacuum drying at 120 deg.C to obtain activated silicon spheres;
(2) adding dioxane into the activated silicon spheres (the mass volume ratio of the activated silicon spheres to the added dioxane is 1: 25g/ml), slowly dropwise adding 2mol/L HC L, heating to 80 ℃, then slowly dropwise adding 1mol/L dioxane solution of triethoxysilane, heating and refluxing for 15h, filtering, washing a filter cake with 30% acetone aqueous solution and dioxane, and drying at 130 ℃ to obtain modified silicon spheres, wherein the mass mole ratio of the activated silicon spheres to the triethoxysilane is 1: 0.005 g/mol.
(3) And sequentially adding trichloromethane, naloxone and 2% isopropanol solution of chloroplatinic acid into the modified silica gel, magnetically stirring, heating and refluxing for 10h, filtering, sequentially washing a filter cake with water, acetone and dichloromethane, sequentially washing with dichloromethane and acetone, and drying at 110 ℃ to obtain the naloxone dimethylsilane bonded silica gel. Wherein the mass molar ratio of the modified silica gel to the naloxone is 1: 5g/mol, the molar ratio of chloroplatinic acid to naloxone as a reaction substrate is 10-6: 1; the mass volume ratio of the modified silica gel to the trichloromethane is 1: 45 g/mL;
(4) and (3) carrying out ultrasonic treatment on 1 part of octadecyl bonded silica gel and 3 parts of naloxone bonded silica gel prepared in the step (2) in 150 parts of carbon tetrachloride solvent at 200W for 40min to prepare a mixed solution, and filling the mixed solution into a chromatographic column with the size of 4.6mm multiplied by 150 mm.
The octadecyl bonded silica gel is purchased from New Material Co, Ltd, of the family Rigaceae, and is named Fuji Chromatorex filler, the product number is 112926-00-8, and the particle size is 3 μm.
Example 3
(1) Adding 25 parts of 1mol/L hydrochloric acid into 1 part of silicon spheres (with an average particle size of 5 μm, Fuji, Japan), stirring at 90 deg.C for reaction for 3h, filtering, washing with ultrapure water to neutrality, and vacuum drying at 120 deg.C to obtain activated silicon spheres;
(2) adding dioxane into the activated silicon spheres (the mass volume ratio of the activated silicon spheres to the added dioxane is 1: 25g/ml), slowly dropwise adding 2mol/L HC L, heating to 80 ℃, then slowly dropwise adding 1mol/L dioxane solution of triethoxysilane, heating and refluxing for 12h, filtering, washing a filter cake with 30% acetone aqueous solution and dioxane, and drying at 130 ℃ to obtain modified silicon spheres, wherein the mass mole ratio of the activated silicon spheres to the triethoxysilane is 1: 0.006 g/mol.
(3) And sequentially adding trichloromethane, naloxone and 2% isopropanol solution of chloroplatinic acid into the modified silica gel, magnetically stirring, heating and refluxing for 10h, filtering, sequentially washing a filter cake with acetone and dichloromethane, sequentially washing with dichloromethane and acetone, and drying at 130 ℃ to obtain the naloxone dimethylsilane bonded silica gel. Wherein the mass molar ratio of the modified silica gel to the naloxone is 1: 8g/mol, the molar ratio of chloroplatinic acid to naloxone as a reaction substrate is 10-5: 1; the mass volume ratio of the modified silica gel to the trichloromethane is 1: 35 g/mL;
(4) and (3) carrying out ultrasonic treatment on 1 part of octadecyl bonded silica gel and 2 parts of naloxone bonded silica gel prepared in the step (2) in 150 parts of carbon tetrachloride solvent at 200W for 40min to prepare a mixed solution, and filling the mixed solution into a chromatographic column with the size of 4.6mm multiplied by 150 mm.
The octadecyl bonded silica gel is purchased from New Material Co, Ltd, of the family Rigaceae, and is named Fuji Chromatorex filler, the product number is 112926-00-8, and the particle size is 5 μm.
Comparative example 1
The comparative example differs from example 3 in that 1 part by mass of naloxone-bonded silica gel was added, and the remainder was identical to example 3.
Comparative example 2
The difference between the comparative example and the example 3 is that toluene is used as the organic solvent in the step (3), and the heating reflux time is 11h, and the rest is consistent with the example 3.
Comparative example 3
The comparative example is different from example 3 in that the mass molar ratio of the modified silica gel to naloxone in step (3) is 1: 3g/mo L, the rest remaining in accordance with example 3.
Effect example 1
The columns obtained in examples 1 to 3 and comparative examples 1 to 3 were used, and the test sample was a 70% acetonitrile aqueous solution containing citric acid, matrine, oxymatrine and pentylbenzene, and the detection wavelength was 210nm as determined by analysis on a waters e2690-UV high performance liquid chromatograph at a flow rate of 1ml/min and a column temperature of 25 ℃ wherein the column of example 3 was passed through the column with a 2% trifluoroacetic acid solution for one week before injection, and then the column was washed with water and acetonitrile-water (70:30) in this order.
The spectra obtained in the above experiment are shown in FIGS. 1-1 to 6, and the integration results are shown in the following tables 1-6.
Table 1 example 1 table of chromatographic integration results
Table 2 example 2 table of chromatographic integration results
Table 3 example 3 table of chromatographic integration results
Table 4 table of chromatographic integration results of comparative example 1
TABLE 5 TABLE OF COMPARATIVE EXAMPLE 2 CHROMATOGRAPHIC INTEGRATION RESULTS
Table 6 table of chromatographic integration results of comparative example 3
The result shows that when the mixing ratio of the octadecyl bonded silica gel to the naloxone bonded silica gel is 1:2-3, the separation degree is good when acidic, alkaline and nonpolar components are separated, the column efficiency is high, the detection time is short, and the acid resistance of the chromatographic packing is strong. When the proportion of the naloxone bonded silica gel in the composite filler is reduced, the separation effect of four components with different polarities and acid and alkali components is poor, and the separation degree does not meet the content measurement requirement; in the research of the reaction of naloxone and modified silica gel, the invention discovers that the selection of an organic solvent and the reaction time have certain influence on the final separation effect of the naloxone and the modified silica gel, the recovery of the product in a column is influenced to a certain extent, the initial judgment shows that the boiling points of toluene and trichloromethane have certain difference, and the difference of the reaction temperature has certain influence on the yield; the invention also finds that the mass molar ratio of reaction substrates hydrogenated silica gel and naloxone is 1: 5-8g/moL, the chromatographic column has good separation effect.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several modifications and decorations can be made without departing from the concept of the present invention, and these modifications and decorations should also be regarded as being within the protection scope of the present invention.
Claims (10)
1. The liquid chromatography column composite filler is characterized by comprising octadecylsilane chemically bonded silica filler and naloxone chemically bonded silica filler.
2. The liquid chromatography column composite filler of claim 1, wherein the mass ratio of octadecylsilane chemically bonded silica filler to naloxone-bonded silica filler is 1: 2-3.
3. The composite filler for liquid chromatography columns according to claim 1, characterized in that the particle size of the octadecylsilane bonded silica filler and naloxone bonded silica filler is 3-5 μm.
4. The composite packing for a liquid chromatography column according to claim 1, wherein the preparation method of the naloxone-bonded silica gel packing comprises the following steps:
(1) activating the silicon spheres to obtain activated silicon spheres;
(2) then reacting triethoxysilane to the surface of the activated silicon spheres to form a silicon-hydrogen bond, thereby obtaining modified silica gel;
(3) adding naloxone into the modified silica gel, adding an organic solvent and an isopropanol solution of chloroplatinic acid, stirring, heating and refluxing for 8-10h, washing and drying to obtain the nano-composite material.
5. The composite packing for liquid chromatography columns of claim 4, wherein step (1) operation comprises: adding the silicon spheres into hydrochloric acid, reacting for 2-3h, and drying to obtain activated silicon spheres for later use.
6. The composite filler for the liquid chromatography column as claimed in claim 4, wherein the reaction in step (2) is obtained by sequentially adding dioxane, 2mol/L hydrochloric acid and 1mol/L triethoxysilane into an activated silicon ball, heating and refluxing for 12-15h, washing with 30% acetone aqueous solution and dioxane, and drying; preferably, the mass molar ratio of the activated silicon spheres to the triethoxysilane in the reaction is 1: 0.005-0.006 g/mol; the mass-volume ratio of the activated silica gel to the dioxane added in the reaction is 1: 23-25 g/ml; the drying temperature is 110-130 ℃.
7. The composite packing for liquid chromatography columns according to claim 4, characterized in that the mass molar ratio of the modified silica gel and naloxone in step (3) is 1: 5-8g/mol, the organic solvent is trichloromethane, and the mol ratio of the chloroplatinic acid to the naloxone is 10-6-10-5: 1; the mass volume ratio of the modified silica gel to the trichloromethane is 1: 25-45 g/mL.
8. The composite packing for liquid chromatography columns according to claim 4, characterized in that the washing in step (3) is acetone and dichloromethane sequentially, and then dichloromethane and acetone sequentially.
9. A chromatographic column made of the composite filler according to any one of claims 1 to 8, wherein the preparation method of the chromatographic column comprises the steps of placing the octadecylsilane chemically bonded silica and the naloxone chemically bonded silica in an organic solvent, mixing, performing ultrasonic treatment, and filling the mixture into a liquid chromatographic column; preferably, the organic solvent is one of acetone, tetrahydrofuran and carbon tetrachloride; the ultrasonic power is 200-500W, and the ultrasonic time is 30-50 min.
10. Use of a composite packing for chromatography columns according to any of claims 1-8 for analytical testing of products containing both hydrophilic, lipophilic and acidic and basic components.
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2021
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| CN101721980A (en) * | 2009-11-13 | 2010-06-09 | 天津博纳艾杰尔科技有限公司 | Mixed fillers of liquid-phase chromatographic column and chromatographic column |
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