Chromatographic packing, process for its preparation and use thereof

Abstract

The present application relates to the technical field of chromatographic packing, in particular to a kind of chromatographic packing and its preparation method and use.The raw material of the chromatographic packing includes: biomass powder, pentafluorophenyl silane, octadecyl silane and raw material silica gel;The weight ratio of the biomass powder, the pentafluorophenyl silane, the octadecyl silane and the raw material silica gel is 1:(1-2):(2-2.5):(4-6).The raw material silica gel in the present application is simultaneously reacted with biomass powder, pentafluorophenyl silane, octadecyl silane, so that the chromatographic packing has good separation degree for a plurality of different types of substances.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of chromatographic packing, in particular to a chromatographic packing, a preparation method and use thereof. BACKGROUND

[0002] In the field of environmental pollutant treatment, it is of great significance to develop efficient and economical adsorption separation materials. Among the numerous pollutants, the difficulty of separation is increased due to the great variety of types, the high similarity of structures, and the small difference in physical and chemical properties. Secondly, traditional separation methods are inefficient, costly, and may have an impact on the environment. In addition, the development of efficient separation technology requires high-precision equipment and complex processes, which puts high demands on the research and development team.

[0003] For example, perfluoro / polyfluorinated compounds, which are widely used in products such as preservative films, paper, paint, and foam extinguishing agents, are discharged into water bodies with industrial wastewater and domestic sewage during production and use, making water bodies the main environmental medium for exposure to perfluoro / polyfluorinated compounds. However, due to their high stability, they are difficult to degrade despite strong light, heat, chemical action, microorganisms, and metabolism of higher vertebrates. With the transmission of perfluoro / polyfluorinated compounds in the food chain and food web, these substances can accumulate to high concentrations in the human body, with a half-life of up to a dozen years. The accumulation of these substances in the human body can interfere with the synthesis and secretion of sex hormones, and have extremely adverse effects on female fertility. However, due to the indispensability of perfluoro / polyfluorinated compounds in production, new perfluoro / polyfluorinated compounds have been developed as substitutes for traditional perfluoro / polyfluorinated compounds, resulting in a wide variety of perfluoro / polyfluorinated compounds in the environment, which are highly similar in structure and have become a major challenge in detecting perfluoro / polyfluorinated compounds in the environment. Similarly, antibiotics, as another important new pollutant, also face the problem of structural diversity in the environment, making separation difficult. Among them, fluoroquinolones (ofloxacin, perfloxacin, norfloxacin) have similar structures and close molecular weights, with only slight differences in side chains, so the polarity of these substances is similar and cannot be completely separated by a single retention mechanism chromatographic column.

[0004] N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate are important industrial organic intermediates, widely used in the fields of medicine, pesticide, dye and material chemistry. In the synthesis or production process, both of them can be coexisting by-products (such as amide and ester competitive reaction), however, the residual ester can affect the safety of the drug, so it needs to be separated to ensure the purity of the product. But the molecular skeleton of the two substances is highly similar and the polarity is similar, so the traditional single hydrophobic retention mechanism chromatographic column cannot separate the two substances. Similarly, uridine, uracil, cytosine, adenosine and adenine are mainly used in the field of medicine and industrial production of food, health care products, etc. In the production of some biological agents, such as vaccines, enzyme preparations, etc., it is necessary to accurately control the composition of the culture medium. Separation of these substances can provide high-quality raw materials for the production of biological agents, and ensure the quality and yield of the product. But uridine, uracil, cytosine, adenosine and adenine are hydrophilic compounds, and cannot be separated by chromatographic column with single hydrophobic retention mechanism. The chromatographic packing material in the prior art is single retention mechanism packing material, which is difficult to separate a plurality of different types of substances. SUMMARY

[0005] In view of the above-mentioned shortcomings of the prior art, the purpose of the present application is to provide a chromatographic packing material, a preparation method and use thereof. The chromatographic packing material described in the present application solves the problem that the single retention mechanism packing material in the prior art is difficult to be used for separating a plurality of different types of substances.

[0006] To achieve the above-mentioned purposes and other related purposes, the present application is obtained by the following technical solutions.

[0007] The first aspect of the present application discloses a chromatographic packing material, the raw material of the chromatographic packing material comprises: biomass powder, pentafluorophenyl silane, octadecyl silane and raw material silica gel; the weight ratio of the biomass powder, the pentafluorophenyl silane, the octadecyl silane and the raw material silica gel is 1:(1-2):(2-2.5):(4-6). The weight ratio of the biomass powder, the pentafluorophenyl silane, the octadecyl silane and the raw material silica gel can be 1:1:1:4, 1:1.2:1:4, 1:1.5:1:4, 1:1.5:1.5:4.5, 1:1.5:1.5:5, 1:1.5:1.5:6, 1:2:1:3, 1:2:2.5:4.5, 1:1.5:2.5:6.

[0008] The octadecyl silane enables the chromatographic packing to generate force with the carbon skeleton of the target, thereby forming hydrophobic retention; the biomass powder enables the chromatographic packing to generate hydrophobic retention and "π-π" conjugation effect between the alkyl chain and benzene ring in the target, and the carboxyl and hydroxyl groups enable the chromatographic packing to generate intermolecular interaction force with the hydrogen in various functional groups such as sulfonic acid group (-SO3H) and carboxylic acid group (-COOH) in the target, thereby forming hydrogen bond effect, which enables specific hydrophilic interaction with the polar groups of hydrophilic compounds such as uracil nucleoside, and the hydrophilic interaction enables the hydrophilic compounds to achieve effective retention and separation in the chromatographic column; the pentafluorophenyl silane enables the chromatographic packing to generate dipole-dipole effect and "π-π" conjugation effect with the target. The raw silica gel is simultaneously reacted with the biomass, pentafluorophenyl silane and octadecyl silane, so that the chromatographic packing separates the compounds with similar structures through hydrophobic retention, hydrogen bond effect and dipole-dipole effect; the hydrophobic retention and hydrophilic retention are ingeniously combined to form a separation system in which multiple retention mechanisms work together, thereby enabling efficient separation of multiple different types of substances in one chromatographic column, achieving accurate and effective detection and monitoring of multiple different compounds, and greatly improving the application range of chromatographic separation.

[0009] Preferably, the raw material of the biomass powder is selected from one or more of oil tea fruit shell, grape seed, pomegranate seed and hawthorn seed.

[0010] Preferably, the biomass powder is defatted biomass powder, and the preparation method of the defatted biomass powder comprises the following steps: mixing and soaking the biomass with an organic solvent.

[0011] More preferably, the organic solvent is selected from one or both of toluene and ethanol.

[0012] Further, the organic solvent is a mixture of toluene and ethanol, and the volume ratio of the toluene to the ethanol is (1-4):1. For example, the volume ratio of the toluene to the ethanol can be (1-1.5):1, (1.5-1.8):1, (1.8-2.0):1, (2.0-2.5):1, (2.5-3.0):1, (3.0-3.5):1, (3.5-4.0):1. In some specific embodiments, the volume ratio of the toluene to the ethanol is 2:1.

[0013] More preferably, the solid-liquid ratio of the biomass powder and the organic solvent is 1 g: (7-20) mL. As the solid-liquid ratio of the biomass powder and the organic solvent can be 1 g: (7-9) mL, 1 g: (9-12) mL, 1 g: (12-15) mL, 1 g: (15-18) mL, 1 g: (18-20) mL. In some embodiments, the solid-liquid ratio of the biomass powder and the organic solvent is 1 g: 15 mL.

[0014] More preferably, the soaking time is 14-36 h. As the soaking time can be 14-18 h, 18-22 h, 22-24 h, 24-28 h, 28-32 h, 32-36 h. In some embodiments, the soaking time is 24 h.

[0015] Preferably, the particle size of the biomass powder is 1.0-2.5 μm.

[0016] Preferably, the specific surface area of the biomass powder is 200-500 m 2 / g.

[0017] Preferably, the pentafluorophenyl silane is selected from one or more of trimethyl pentafluorophenyl silane, dimethyl pentafluorophenyl silane, aminodimethyl pentafluorophenyl silane, trimethoxy (pentafluorophenyl) silane, pentafluorophenyl dimethyl chlorosilane, pentafluorophenyl triethoxysilane, pentafluorophenyl ethoxydimethyl silane, and pentafluorophenyl propyl trimethoxysilane.

[0018] Preferably, the octadecyl silane is selected from one or more of octadecyl trichlorosilane, octadecyl dimethyl chlorosilane, octadecyl methyl dichlorosilane. In some embodiments, the octadecyl silane is octadecyl trichlorosilane.

[0019] Preferably, the particle size of the chromatographic packing is 3.5 μm-10.5 μm. As the particle size of the chromatographic packing can be 3.5 μm-5 μm, 5 μm-8 μm, 8 μm-10.5 μm.

[0020] Preferably, the particle size of the raw silica gel is 1 μm-8 μm. As the particle size of the raw silica gel can be 1 μm-2 μm, 2 μm-4 μm, 4 μm-6 μm, 6 μm-8 μm.

[0021] Preferably, the pore size of the raw silica gel is As the pore size of the raw silica gel is

[0022] Preferably, the specific surface area of the chromatographic packing is 200-500 m 2 / g. As the specific surface area of the chromatographic packing can be 200-250 m2 / g, 250~300m 2 / g, 300~350m 2 / g, 350~400m 2 / g, 400~450m 2 / g, 450~500m 2 / g.

[0023] Preferably, the pore size of the chromatographic packing is [missing information]. The pore size of the chromatographic packing material is as follows:

[0024] Preferably, the specific surface area of ​​the raw silicone is 200-500 m². 2 / g. The specific surface area of ​​the raw material silica gel can be 200-250m². 2 / g, 250~300m 2 / g, 300~350m 2 / g, 350~400m 2 / g, 400~450m 2 / g, 450~500m 2 / g.

[0025] A second aspect of this invention discloses a method for preparing the chromatographic packing material as described above. The preparation method includes the following steps: mixing raw silica gel with biomass powder, pentafluorophenylsilane, and octadecylsilane, and reacting the mixture to obtain the chromatographic packing material.

[0026] Preferably, the raw material silica gel further includes a pretreatment step before mixing, the pretreatment including mixing with one or two of toluene and / or ethanol.

[0027] More preferably, the pretreatment includes mixing with toluene and ethanol in a volume ratio of (1–4):1. For example, the volume ratio of toluene to ethanol can be (1–1.5):1, (1.5–1.8):1, (1.8–2.0):1, (2.0–2.5):1, (2.5–3.0):1, (3.0–3.5):1, or (3.5–4.0):1. In some specific embodiments, the volume ratio of toluene to ethanol is 2:1.

[0028] More preferably, the solid-liquid ratio of the raw silica gel and the mixture of toluene and ethanol is 1 g: (7-20) mL. For example, the solid-liquid ratio of the raw silica gel and the mixture of toluene and ethanol can be 1 g: (7-9) mL, 1 g: (9-12) mL, 1 g: (12-15) mL, 1 g: (15-18) mL, 1 g: (18-20) mL. In some embodiments, the solid-liquid ratio of the raw silica gel and the mixture of toluene and ethanol is 1 g: 15 mL.

[0029] More preferably, the temperature of the mixing is 90-300°C. For example, the temperature of the mixing can be 90-150°C, 150-200°C, 200-250°C, 250-280°C, 280-300°C.

[0030] More preferably, the time of the mixing is 0.8-6 h. For example, the time of the mixing can be 0.8-2 h, 2-3 h, 3-4 h, 4-5 h, 5-6 h.

[0031] More preferably, the mixture is cooled to room temperature.

[0032] Preferably, the preparation method is carried out under a protective atmosphere. More preferably, the protective atmosphere is an oxygen-free atmosphere. In some embodiments, the oxygen-free atmosphere is a N2 atmosphere.

[0033] Preferably, the temperature of the reaction is 80-350°C. For example, the temperature of the reaction can be 80-120°C, 120-180°C, 180-240°C, 240-300°C, 300-350°C.

[0034] Preferably, the time of the reaction is 7-40 h. For example, the time of the reaction can be 7-12 h, 12-18 h, 18-24 h, 24-30 h, 30-40 h.

[0035] The third aspect of the present application discloses a method for separating perfluoro / polyfluoro compounds, and / or separating N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate, and / or separating antibiotics, and / or separating uridine, uracil, cytosine, adenosine and adenine, which comprises the following steps: adding a solution containing the separation target into a liquid chromatograph using the chromatographic column to separate.

[0036] Preferably, the separation mode of the separation includes normal phase chromatography and reverse phase chromatography. It should be noted that the chromatographic column described in the present application has hydrophobic retention, hydrogen bond and dipole-dipole interaction, and thus is suitable for both normal phase chromatography and reverse phase chromatography.

[0037] Preferably, the column temperature of the chromatographic column is 25°C to 45°C, such as the column temperature can be 25°C to 30°C, 30°C to 35°C, 35°C to 40°C, 40°C to 45°C.

[0038] Preferably, the particle size of the chromatographic packing is 3.1 pm to 10 pm. Such as the particle size of the chromatographic packing can be 3.1 to 3.5 pm, 3.5 to 4.5 pm, 4.5 to 5.5 pm, 5.5 to 6.5 pm, 6.5 to 7.5 pm, 7.5 to 8.5 pm, 8.5 to 9.5 pm, 9.5 to 10 pm.

[0039] Preferably, the column length of the chromatographic column is 100 mm to 300 mm. Such as the column length of the chromatographic column can be 100 mm to 150 mm, 150 mm to 200 mm, 200 mm to 250 mm, 250 mm to 300 mm.

[0040] Preferably, the inner diameter of the chromatographic column is 2 mm to 10 mm. Such as the inner diameter of the chromatographic column can be 2 mm to 2.1 mm, 2.1 to 4.6 mm, 4.6 mm to 8 mm, 8 mm to 10 mm.

[0041] Preferably, the injection volume of the liquid chromatograph is 2 pL to 20 pL, such as the injection volume can be 2 pL to 5 pL, 5 pL to 10 pL, 10 pL to 15 pL, 15 pL to 20 pL.

[0042] Preferably, the flow rate of the mobile phase is 0.3 mL / min to 2 mL / min, such as the flow rate of the mobile phase can be 0.3 mL / min to 0.5 mL / min, 0.5 mL / min to 0.8 mL / min, 0.8 mL / min to 1 mL / min, 1 mL / min to 1.5 mL / min, 1.5 mL / min to 2 mL / min.

[0043] Preferably, the solvent of the solution containing the separation target is methanol.

[0044] Preferably, the perfluoro / polyfluorinated compound includes one or more of trifluoroacetic acid, perfluoropropionic acid, perfluorobutyric acid, perfluorovaleric acid, perfluorohexanoic acid, perfluoroheptanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, perfluorododecanoic acid, perfluorotridecanoic acid, perfluorotetradecanoic acid, perfluorohexadecanoic acid, perfluorooctadecanoic acid, 3:3 fluoroterpolymer carboxylic acid, 5:3 fluoroterpolymer carboxylic acid, 7:3 fluoroterpolymer carboxylic acid, 6:2 fluoroterpolymer carboxylic acid, 8:2 fluoroterpolymer carboxylic acid, 1,1,2,2-tetrafluoro-2-(perfluoroethoxy)ethanesulfonic acid, 9-chloroperfluoro-3-nonyloxy sulfonic acid, perfluorooctanesulfonamide acetic acid, 8:2 fluoroterpolymer phosphoric acid diester.

[0045] Preferably, the antibiotic is selected from one or more of ofloxacin, perfloxacin, norfloxacin, chloramphenicol and flumequine.

[0046] Preferably, when separating perfluoro / polyfluoro compounds, the liquid chromatograph uses a mobile phase of a mixture of ammonium acetate aqueous solution and methanol.

[0047] More preferably, the concentration of the ammonium acetate aqueous solution is 1 mmol / L to 5 mmol / L, and the solvent is water, such as the concentration of the ammonium acetate aqueous solution can be 1 mmol / L to 2 mmol / L, 2 mmol / L to 3 mmol / L, 3 mmol / L to 4 mmol / L, 4 mmol / L to 5 mmol / L.

[0048] More preferably, the mobile phase uses gradient elution to separate perfluoro / polyfluoro compounds.

[0049] Preferably, when the separation target is a perfluoro / polyfluoro compound, the concentration of the separation target compound in the solution containing the separation target is 0.05 to 0.2 μg / mL. Such as the concentration of the separation target compound in the solution containing the separation target can be 0.05 to 0.1 μg / mL, 0.1 to 0.15 μg / mL, 0.15 to 0.2 μg / mL.

[0050] Preferably, when the separation target is a perfluoro / polyfluoro compound, the detector used in the liquid chromatograph is a mass spectrometer.

[0051] Preferably, when separating N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate, the liquid chromatograph uses a mobile phase of a mixture of formic acid aqueous solution and methanol.

[0052] More preferably, in the formic acid aqueous solution, the volume ratio of formic acid to water is 0.01 to 0.2:100. Such as the volume ratio of formic acid to water can be 0.01 to 0.0.05:100, 0.005 to 0.1:100, 0.1 to 0.15:100, 0.15 to 0.2:100.

[0053] More preferably, the volume ratio of the formic acid aqueous solution to methanol is (35 to 55):55. Such as the volume ratio of the formic acid aqueous solution to methanol can be (35 to 40):55, (40 to 45):55, (45 to 50):55, (50 to 55):55.

[0054] Preferably, when the separation target is N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate, the concentration of the separation target compound in the solution containing the separation target is 0.02 to 0.1 mg / mL. The concentration of the separation target compound in the solution containing the separation target can be 0.02 to 0.05 mg / mL, 0.05 to 0.07 mg / mL, 0.07 to 0.1 mg / mL.

[0055] Preferably, when the separation target is N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate, the detector used in the liquid chromatograph is an ultraviolet detector.

[0056] More preferably, the detection wavelength of the ultraviolet detector is 250 to 300 nm. The detection wavelength of the ultraviolet detector can be 250 to 260 nm, 260 to 270 nm, 270 to 280 nm, 280 to 288 nm, 288 to 295 nm, 295 to 300 nm.

[0057] Preferably, when the separation target is an antibiotic, the mobile phase used in the liquid chromatograph is a mixture of an aqueous phosphoric acid solution and methanol.

[0058] More preferably, the concentration of the aqueous phosphoric acid solution is 0.02 mol / L to 1 mol / L, and the solvent is water. The concentration of the aqueous phosphoric acid solution can be 0.02 to 0.05 mol / L, 0.05 to 0.08 mol / L, 0.08 mol / L to 1 mol / L.

[0059] More preferably, the aqueous phosphoric acid solution is adjusted to a pH of 1.5 to 3.5 with triethylamine. The pH can be 1.5 to 2.0, 2.0 to 2.5, 2.5 to 2.8, 2.8 to 3.5.

[0060] Preferably, when the separation target is an antibiotic, the concentration of the separation target compound in the solution containing the separation target is 0.02 to 0.1 mg / mL. The concentration of the separation target compound in the solution containing the separation target can be 0.02 to 0.05 mg / mL, 0.05 to 0.07 mg / mL, 0.07 to 0.1 mg / mL.

[0061] Preferably, when the separation target is an antibiotic, the detector used in the liquid chromatograph is an ultraviolet detector.

[0062] More preferably, the detection wavelength of the ultraviolet detector is 250 to 300 nm. The detection wavelength of the ultraviolet detector can be 250 to 260 nm, 260 to 274 nm, 274 to 280 nm, 280 to 288 nm, 288 to 295 nm, 295 to 300 nm.

[0063] More preferably, the mobile phase employs gradient elution to separate the antibiotic.

[0064] Preferably, when separating uridine, uracil, cytosine, adenosine and adenine, the liquid chromatograph uses a mobile phase of a mixture of water and methanol.

[0065] More preferably, the volume ratio of water to methanol is (70-100):10. For example, the volume ratio of water to methanol can be (70-80):10, (80-90):10, (90-100):10.

[0066] Preferably, when the target substance is uridine, uracil, cytosine, adenosine and adenine, the concentration of the target substance in the solution containing the target substance is 0.02-0.1 mg / mL. For example, the concentration of the target substance in the solution containing the target substance can be 0.02-0.05 mg / mL, 0.05-0.07 mg / mL, 0.07-0.1 mg / mL.

[0067] Preferably, when the target substance is an antibiotic, the detector used in the liquid chromatograph is an ultraviolet detector.

[0068] More preferably, the detection wavelength of the ultraviolet detector is 250-300 nm. For example, the detection wavelength of the ultraviolet detector can be 250-254 nm, 254-274 nm, 274-280 nm, 280-288 nm, 288-295 nm, 295-300 nm.

[0069] The fourth aspect of the present application discloses a use of the chromatographic packing as described above in separating perfluoro / multifluoro compounds.

[0070] Preferably, the perfluoro / multifluoro compounds include one or more of trifluoroacetic acid, perfluoropropionic acid, perfluorobutyric acid, perfluorovaleric acid, perfluorohexanoic acid, perfluoroheptanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, perfluorododecanoic acid, perfluorotridecanoic acid, perfluorotetradecanoic acid, perfluorohexadecanoic acid, perfluorooctadecanoic acid, 3:3 fluoroterpolymer carboxylic acid, 5:3 fluoroterpolymer carboxylic acid, 7:3 fluoroterpolymer carboxylic acid, 6:2 fluoroterpolymer carboxylic acid, 8:2 fluoroterpolymer carboxylic acid, 1,1,2,2-tetrafluoro-2-(perfluoroethoxy)ethanesulfonic acid, 9-chloroperfluoro-3-nonyloxy sulfonic acid, perfluorooctanesulfonamide acetic acid, 8:2 fluoroterpolymer phosphoric acid diester.

[0071] More preferably, the chromatographic packing material is effective to separate perfluoro / polyluorinated compounds including trifluoroacetic acid, perfluoropropionic acid, perfluorobutyric acid, perfluorovaleric acid, perfluorohexanoic acid, perfluoroheptanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, perfluorododecanoic acid, perfluorotridecanoic acid, perfluorotetradecanoic acid, perfluorohexadecanoic acid, perfluorooctadecanoic acid.

[0072] More preferably, the chromatographic packing material is effective to separate 3:3 fluorotelomer carboxylic acid, 5:3 fluorotelomer carboxylic acid, 7:3 fluorotelomer carboxylic acid, 6:2 fluorotelomer carboxylic acid, 8:2 fluorotelomer carboxylic acid.

[0073] More preferably, the chromatographic packing material is effective to separate 1,1,2,2-tetrafluoro-2-(perfluoroethoxy)ethanesulfonic acid, 9-chloroperfluoro-3-nonyloxy sulfonic acid, perfluorooctanesulfonamide acetic acid, 8:2 fluorotelomer phosphoric acid diester.

[0074] The fifth aspect of the present application discloses the use of a chromatographic packing material as described above in separating N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate.

[0075] The sixth aspect of the present application discloses the use of a chromatographic packing material as described above in separating antibiotics.

[0076] Preferably, the antibiotics are selected from one or more of ofloxacin, perfloxacin, norfloxacin, chloramphenicol and flumequine.

[0077] The seventh aspect of the present application discloses the use of a chromatographic packing material as described above in separating uridine, uracil, cytosine, adenosine, adenine.

[0078] In the present application, the target structures to be separated are shown in Table 1:

[0079] Table 1

[0080]

[0081]

[0082]

[0083]

[0084] Compared with the prior art, the application has the following beneficial effects: the raw material silica gel in the application is simultaneously reacted with biomass powder, pentafluorophenylsilane and octadecylsilane, so that the chromatographic column separates compounds with similar structures through hydrophobic retention, hydrogen bonding and dipole-dipole interaction, ingeniously combines hydrophobic retention with hydrophilic retention, forms a separation system in which multiple retention mechanisms work together, and thus can realize efficient separation of multiple different types of substances on one chromatographic column, achieves accurate and effective detection and monitoring of multiple different compounds, and greatly improves the application range of chromatographic separation. BRIEF DESCRIPTION OF DRAWINGS

[0085] Figures 1-3 The MRM chromatogram of perfluoro / polyfluorinated compounds obtained by using the chromatographic column 1 in the application is shown.

[0086] Figure 4 The liquid chromatogram of N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate obtained by using the chromatographic column 2 in the application is shown.

[0087] Figure 5 The liquid chromatogram of antibiotics obtained by using the chromatographic column 3 in the application is shown.

[0088] Figure 6 The liquid chromatogram of uracil riboside, uracil, cytosine, adenine riboside and adenine obtained by using the chromatographic column 4 in the application is shown.

[0089] Figures 7-9 The MRM chromatogram of perfluoro / polyfluorinated compounds obtained by using the chromatographic column 5 in the application is shown.

[0090] Figure 10 The liquid chromatogram of N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate obtained by using the chromatographic column 6 in the application is shown.

[0091] Figure 11 The liquid chromatogram of antibiotics obtained by using the chromatographic column 7 in the application is shown.

[0092] Figure 12 The liquid chromatogram of uracil riboside, uracil, cytosine, adenine riboside and adenine obtained by using the chromatographic column 8 in the application is shown. DETAILED DESCRIPTION

[0093] The embodiments of the application are described below by specific specific examples, and those skilled in the art can easily understand other advantages and effects of the application from the content disclosed in the specification.

[0094] Before further description of the embodiments of the application, it is understood that the application is not limited in scope to the specific embodiments described herein; and that the embodiments of the application are presented as being illustrative of the application rather than as limitations on the scope of the application. The test methods used in the following examples, unless otherwise indicated, were typically conducted in accordance with conventional procedures or as recommended by the manufacturer.

[0095] When numerical ranges are given, it is understood that every numerical range encompassing the lower value and the upper value of the range is contemplated, unless otherwise indicated. Unless otherwise defined, all technical and scientific terms used in the application have the same meaning as commonly understood by one of ordinary skill in the art. Any method, apparatus, material or substance similar or equivalent to those described in the embodiments of the application can be used in the practice of the application, unless otherwise indicated. Unless otherwise indicated, the methods, devices, and materials described herein are those presently known in the art to which the application pertains.

[0096] In the present application, the applicant provides a chromatographic packing material, a preparation method and use thereof, in order to solve the problem of low separation degree of chromatographic columns with single retention mechanism for structurally similar compounds in the prior art. In the chromatographic packing material, silica gel is simultaneously combined with biomass powder, pentafluorophenylsilane and octadecylsilane. Three groups of compounds are separated by multiple retention effects such as hydrophobic retention, hydrogen bonding and dipole-dipole interaction, thereby having good separation effect on different types of compounds.

[0097] Embodiment 1

[0098] The present embodiment provides a chromatographic packing material, wherein the raw material of the chromatographic packing material comprises: raw silica gel, oil tea fruit shell, trimethyl pentafluorophenylsilane and octadecyltrichlorosilane, and the weight ratio of the raw silica gel, the oil tea fruit shell, the trimethyl pentafluorophenylsilane and the octadecyltrichlorosilane is 5:1:1.5:2; the average particle size of the raw silica gel is 1.7 μm, and the average pore size is 300 m / g; the average particle size of the biomass is 2.5 μm, and the average specific surface area is 300 m 2 / g; the average particle size of the biomass is 2.5 μm, and the average specific surface area is 300 m 2 / g; the average particle size of the biomass is 2.5 μm, and the average specific surface area is 300 m

[0099] The present embodiment also provides a preparation method of the chromatographic packing material as described above, and the preparation method comprises the following steps:

[0100] 1) The dried oil tea fruit shell is crushed into particles by a crusher, and then dried in an oven at 80°C.

[0101] 2) Take 20.0 g of oil tea fruit shell powder in 300 mL of a mixture of toluene: ethanol in a volume ratio of 2:1, ultrasonic immersion for 24 h, filter and dry, grind and store, to obtain defatted oil tea fruit shell powder.

[0102] 3) Put 10.0 g of raw silica gel and 90 mL of a mixture of toluene: ethanol in a volume ratio of 2:1 into a 100 mL three-necked flask, stir and reflux at 150°C for 2.5 h, use a water trap to remove the water evaporated, then cool to room temperature to form a mixture.

[0103] 4) Under N2 protection, add 9.0 g of pre-mixed silane to the mixture, the pre-mixed silane is composed of defatted oil tea fruit shell powder, trimethylpentakisfluorophenylsilane and octadecyltrichlorosilane, the weight ratio of oil tea fruit shell, trimethylpentakisfluorophenylsilane and octadecyltrichlorosilane is 1:1.5:2, stir and reflux at 200°C for 20 h, after the reaction is completed, cool to about 50°C, filter using a vacuum filter, then wash twice with toluene respectively; wash with 80 wt% tetrahydrofuran aqueous solution, methanol, acetonitrile, and vacuum dry the washed product at 110°C for 24 hours to obtain the chromatographic packing material.

[0104] Example 2

[0105] The difference between this embodiment and Example 1 is that the average particle size of the raw silica gel in the raw material of the chromatographic packing material of this embodiment is 3.5 μm, and the average specific surface area is 400 m 2 / g; the particle size of the chromatographic packing material is 5.5 μm.

[0106] Example 3

[0107] The difference between this embodiment and Example 2 is that the oil tea fruit shell in the raw material of the chromatographic packing material of this embodiment is replaced by grape seeds, the trimethylpentakisfluorophenylsilane is replaced by dimethylpentakisfluorophenylsilane, and the octadecyltrichlorosilane is replaced by octadecyldimethylchlorosilane.

[0108] Example 4

[0109] The difference between this embodiment and Example 3 is that in the raw material of the chromatographic packing material of this embodiment, the weight ratio of raw silica gel: biomass powder: pentakisfluorophenylsilane: octadecylsilane is modified from 5:1:1.5:2 to 6:1:2:2.5.

[0110] Comparative Example 1

[0111] The difference between this embodiment and Example 1 is that the raw material of the chromatographic packing material of this embodiment does not contain biomass powder and pentakisfluorophenylsilane.

[0112] Comparative Example 2

[0113] The difference between this comparative example and Example 2 is that the raw material of the chromatographic packing of this comparative example does not contain biomass.

[0114] Comparative Example 3

[0115] The difference between this comparative example and Example 3 is that the raw material of the chromatographic packing of this comparative example does not contain biomass and pentafluorophenyl silane.

[0116] Comparative Example 4

[0117] The difference between this comparative example and Example 4 is that in the raw material of the chromatographic packing of this comparative example, the raw material silica gel: biomass powder: pentafluorophenyl silane: octadecyl silane is changed from 5: 1: 1.5: 2 to 5: 0.2: 0.2: 2.5.

[0118] Application Example 1

[0119] This application example provides a method for separating perfluoro / multi-fluorinated compounds, which uses the chromatographic column prepared from the chromatographic packing prepared in Example 1, and the method comprises the following steps:

[0120] 1) Prepare the chromatographic column:

[0121] Prepare the chromatographic column using the chromatographic packing obtained in Example 1;

[0122] The particle size of the chromatographic packing in the chromatographic column 1 is 3.5 μm, and the pore size is The size of the chromatographic column is 2.1 x 100 mm.

[0123] 2) Configure the mobile phase

[0124] Using 2 mmol / L ammonium acetate aqueous solution and methanol as raw materials, different mobile phases are configured at different times according to Table 2, which is the mobile phase gradient table.

[0125] 3) Prepare the test target:

[0126] Using equal amounts of trifluoroacetic acid, perfluoropropionic acid, perfluorobutyric acid, perfluoropentanoic acid, perfluorohexanoic acid, perfluoroheptanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, perfluorododecanoic acid, perfluorotridecanoic acid, perfluorotetradecanoic acid, perfluorohexadecanoic acid, perfluorooctadecanoic acid, 3:3 fluoroterpolymer carboxylic acid, 5:3 fluoroterpolymer carboxylic acid, 7:3 fluoroterpolymer carboxylic acid, 6:2 fluoroterpolymer carboxylic acid, 8:2 fluoroterpolymer carboxylic acid, 1,1,2,2-tetrafluoro-2-(perfluoroethoxy) ethanesulfonic acid, 9-chloroperfluoro-3-nonyloxy sulfonic acid, perfluorooctanesulfonamide acetic acid, and 8:2 fluoroterpolymer phosphoric acid diester as raw materials, the methanol is used as a solvent to configure a perfluoro / multi-fluorinated compound mixed standard solution with a concentration of 0.1 μg / mL.

[0127] The high performance liquid chromatograph was used with a flow rate of 0.3 mL / min, a column temperature of 40°C, an injection volume of 2 μL, and a detector of mass spectrometer. The mass spectrometer conditions are shown in Table 3, and the ion source was electrospray, negative ion mode, and multiple reaction monitoring (MRM). The ion source parameters are as follows: curtain gas pressure 35.0 psi; spray voltage -4500 V; atomization temperature 500°C; atomization gas pressure 50 psi; auxiliary gas pressure 50 psi.

[0128] The perfluoro / polyfluoro compound standard solution was injected according to the chromatographic and mass spectrometric conditions in Table 2 and Table 3, and the MRM chromatogram was recorded. The test results of the chromatographic column 1 are shown in Table 4. Figures 1-3

[0129] Figure 1 Peak 1 represents trifluoroacetic acid, peak 2 represents perfluoropropionic acid, peak 3 represents perfluorobutyric acid, peak 4 represents perfluoropentanoic acid, peak 5 represents perfluorohexanoic acid, peak 6 represents perfluoroheptanoic acid, peak 7 represents perfluorooctanoic acid, peak 8 represents perfluorononanoic acid, peak 9 represents perfluorodecanoic acid, peak 10 represents perfluoroundecanoic acid, peak 11 represents perfluorododecanoic acid, peak 12 represents perfluorotridecanoic acid, peak 13 represents perfluorotetradecanoic acid, peak 14 represents perfluorohexadecanoic acid, and peak 15 represents perfluorooctadecanoic acid.

[0130] Figure 2 Peak 1 represents 3:3 fluorotelomer carboxylic acid, peak 2 represents 5:3 fluorotelomer carboxylic acid, peak 3 represents 7:3 fluorotelomer carboxylic acid, peak 4 represents 6:2 fluorotelomer carboxylic acid, and peak 5 represents 8:2 fluorotelomer carboxylic acid.

[0131] Figure 3 Peak 1 represents 1,1,2,2-tetrafluoro-2-(perfluoroethoxy)ethanesulfonic acid, peak 2 represents 9-chloroperfluoro-3-nonyloxy sulfonic acid, peak 3 represents perfluorooctanesulfonamide acetic acid, and peak 4 represents 8:2 fluorotelomer phosphoric acid diester.

[0132] From the above, it can be seen that the raw material of the chromatographic column 1 contains biomass, pentafluorophenylsilane, and octadecylsilane, and the perfluoro / polyfluoro compounds obtained by testing the above chromatographic column can be effectively separated, indicating that the chromatographic column can be used for accurate and effective detection and monitoring of perfluoro / polyfluoro compounds. Figures 1-3 Table 2

[0133]

[0134]

[0135] Table 3

[0136]

[0137]

[0138] Application Example 2​​

[0139] This application example provides a method for separating N-tert-butyl-4-aminobenzamide and methyl para-aminobenzoate. The separation method uses chromatographic columns prepared with the packing material obtained in Example 2. The separation method includes the following steps:

[0140] 1) Prepare the chromatographic column:

[0141] Chromatographic columns 2 were prepared using the chromatographic packing material obtained in Example 2.

[0142] The chromatographic packing material in column 2 has a particle size of 5.5 μm and a pore size of [missing information]. The column size is 4.6 × 250 mm.

[0143] 2) Configure the mobile phase

[0144] Using 0.1% formic acid water and methanol as raw materials, the volume ratio of methanol to 0.1% formic acid water is 45:55.

[0145] 3) Prepare the test target:

[0146] Using equal masses of N-tert-butyl-4-aminobenzamide and methyl para-aminobenzoate as raw materials, and methanol as solvent, a mixed standard solution with a concentration of 0.05 mg / mL was prepared.

[0147] A high-performance liquid chromatograph was used with a flow rate of 1 mL / min, a column temperature of 30℃, an injection volume of 10 μL, and an ultraviolet detector with a detection wavelength of 288 nm.

[0148] According to the above chromatographic conditions, the standard solution of the test target was injected, and the chromatogram was recorded. The test results of column 2 are as follows: Figure 4 As shown.

[0149] Figure 4 Peak 1 represents N-tert-butyl-4-aminobenzoamide, and peak 2 represents methyl para-aminobenzoate.

[0150] from Figure 4 It can be seen that the raw materials of the chromatographic packing material of chromatographic column 2 contain biomass, pentafluorophenylsilane and octadecylsilane. The N-tert-butyl-4-aminobenzamide and methyl para-aminobenzoate obtained by the above chromatographic column test can achieve effective separation, indicating that the use of this chromatographic column can achieve accurate and effective detection and monitoring of N-tert-butyl-4-aminobenzamide and methyl para-aminobenzoate.

[0151] Application Example 3

[0152] The application example provides a separation method of antibiotics, the antibiotics are ofloxacin, perfloxacin, norfloxacin, chloramphenicol and flumequine, a chromatographic column is prepared by using the chromatographic packing prepared in the example 3, and the separation method comprises the following steps:

[0153] 1) Preparing the chromatographic column:

[0154] The chromatographic column 3 is prepared by using the chromatographic packing prepared in the example 3

[0155] The particle size of the chromatographic packing in the chromatographic column 3 is 5.5 μm, and the pore size is The size of the chromatographic column is 4.6*250 mm.

[0156] 2) Configuring the mobile phase

[0157] 0.05 mol / L phosphoric acid solution and methanol are used as raw materials, the pH of the phosphoric acid solution is adjusted to 2.8 by using triethylamine, different mobile phases are configured at different times according to Table 4, and the table 4 is a mobile phase gradient table.

[0158] Table 4

[0159]

[0160] 3) Preparing the test target:

[0161] Equal mass ofloxacin, perfloxacin, norfloxacin, chloramphenicol and flumequine are used as raw materials, and methanol is used as a solvent to configure an antibiotic mixed standard solution with a concentration of 0.05 mg / mL.

[0162] An HPLC instrument is used, the flow rate is 0.8 mL / min, the column temperature is 40 DEG C, the injection amount is 10 μL, the detector is an ultraviolet detector, and the detection wavelength is 274 nm.

[0163] According to the above chromatographic conditions, the test target standard solution is injected, and a chromatogram is recorded, and the test result of the chromatographic column 3 is as shown in the following table 5. Figure 5

[0164] Figure 5 The peak 1 represents ofloxacin, the peak 2 represents perfloxacin, the peak 3 represents norfloxacin, the peak 4 represents chloramphenicol, and the peak 5 represents flumequine.

[0165] From Figure 5 It can be known that the raw material of the chromatographic packing of the chromatographic column 3 contains biomass, pentafluorophenylsilane and octadecylsilane, the ofloxacin, perfloxacin, norfloxacin, chloramphenicol and flumequine obtained by the chromatographic column test can be effectively separated, and it is indicated that the chromatographic column can be used to accurately and effectively detect and monitor the ofloxacin, perfloxacin, norfloxacin, chloramphenicol and flumequine.​

[0166] Application Example 4

[0167] The present application provides a separation method of uracil nucleoside, uracil, cytosine, adenine nucleoside and adenine, which uses the chromatographic column prepared by the chromatographic packing material prepared in Example 4, and comprises the following steps:

[0168] 1) Preparation of chromatographic column:

[0169] Preparation of chromatographic column 4 using the chromatographic packing material obtained in Example 4

[0170] The particle size of the chromatographic packing material in the chromatographic column 4 is 5.5 μm, and the pore size is The size of the chromatographic column is 4.6 x 250 mm.

[0171] 2) Preparation of mobile phase

[0172] Using water and methanol as raw materials, the volume ratio of methanol to water is 10:90.

[0173] 3) Preparation of test target:

[0174] Using equal amounts of uracil nucleoside, uracil, cytosine, adenine nucleoside and adenine as raw materials, and methanol as solvent, a mixed standard solution with a concentration of 0.05 mg / mL is prepared.

[0175] Using a high performance liquid chromatograph, the flow rate is 1 mL / min, the column temperature is 30°C, the injection amount is 10 μL, and the detector is an ultraviolet detector with a detection wavelength of 254 nm.

[0176] According to the above chromatographic conditions, the test target standard solution is injected, and the chromatogram is recorded. The test results of the chromatographic column 4 are shown in Figure 6 .

[0177] Figure 6 Peak 1 represents cytosine, peak 2 represents uracil, peak 3 represents uracil nucleoside, peak 4 represents adenine, and peak 5 represents adenine nucleoside.

[0178] From Figure 6 It can be seen that the raw material of the chromatographic packing material of the chromatographic column 4 contains biomass, pentafluorophenylsilane and octadecylsilane, and the uracil nucleoside, uracil, cytosine, adenine nucleoside and adenine obtained by the above chromatographic column test can be effectively separated, which indicates that the chromatographic column can achieve accurate and effective detection and monitoring of uracil nucleoside, uracil, cytosine, adenine nucleoside and adenine.

[0179] Application Example 5

[0180] The application example is different from application example 1 in that the separation method adopts the chromatographic column prepared from the chromatographic packing material prepared in Comparative Example 1, and the chromatographic column 5 is prepared from the chromatographic packing material obtained in Comparative Example 1.

[0181] Other chromatographic conditions are the same as those in application example 1. The test target standard solution is injected according to the above chromatographic conditions, and the chromatogram is recorded. The test results of the chromatographic column 2 are shown in Figures 7-9 .

[0182] Figure 7 The middle peak 1 represents trifluoroacetic acid, the peak 2 represents perfluoropropionic acid, the peak 3 represents perfluorobutyric acid, the peak 4 represents perfluoropentanoic acid, the peak 5 represents perfluorohexanoic acid, the peak 6 represents perfluoroheptanoic acid, the peak 7 represents perfluorooctanoic acid, the peak 8 represents perfluorononanoic acid, the peak 9 represents perfluorodecanoic acid, the peak 10 represents perfluoroundecanoic acid, the peak 11 represents perfluorododecanoic acid, the peak 12 represents perfluorotridecanoic acid, the peak 13 represents perfluorotetradecanoic acid, the peak 14 represents perfluorohexadecanoic acid, and the peak 15 represents perfluorooctadecanoic acid.

[0183] Figure 8 The middle peak 1 represents 3:3 fluorine-regulated polymer carboxylic acid, the peak 2 represents 5:3 fluorine-regulated polymer carboxylic acid, the peak 3 represents 7:3 fluorine-regulated polymer carboxylic acid, the peak 4 represents 6:2 fluorine-regulated polymer carboxylic acid, and the peak 5 represents 8:2 fluorine-regulated polymer carboxylic acid.

[0184] Figure 9 The middle peak 1 represents 1,1,2,2-tetrafluoro-2-(perfluoroethoxy) ethanesulfonic acid, the peak 2 represents 9-chloroperfluoro-3-nonyloxy sulfonic acid, the peak 3 represents perfluorooctanesulfonamide acetic acid, and the peak 4 represents 8:2 fluorine-regulated polymer phosphoric acid diester.

[0185] It can be seen from Figures 7-9 Comparative Example 1 that, compared with application example 1, the raw material of the chromatographic packing material of the chromatographic column 5 does not contain biomass and pentafluorophenylsilane, resulting in that the perfluoro / fuorinated compounds cannot be completely separated, especially between perfluorododecanoic acid and perfluorohexadecanoic acid, between perfluorotridecanoic acid and perfluorooctadecanoic acid, between 5:3 fluorine-regulated polymer carboxylic acid and 7:3 fluorine-regulated polymer carboxylic acid, and between 9-chloroperfluoro-3-nonyloxy sulfonic acid and perfluorooctanesulfonamide acetic acid, and the peaks are basically out at the same time.

[0186] Application Example 6

[0187] The application example is different from application example 2 in that the separation method adopts the chromatographic column prepared from the chromatographic packing material prepared in Comparative Example 2, and the chromatographic column 6 is prepared from the chromatographic packing material obtained in Comparative Example 2.

[0188] Other chromatographic conditions are the same as those in application example 2. The test target standard solution is injected according to the above chromatographic conditions, and the chromatogram is recorded. The test results of the chromatographic column 6 are shown in Figure 10 .

[0189] Figure 10 Middle peak 1 represents N-tert-butyl-4-aminobenzamide, and peak 2 represents methyl p-aminobenzoate.

[0190] From Figure 10 It can be seen that, compared with Application Example 2, the raw material of the chromatographic packing of the chromatographic column 6 has no biomass, resulting in that the N-tert-butyl-4-aminobenzamide and methyl p-aminobenzoate with similar structures cannot be separated at the same time.

[0191] Application Example 7

[0192] The difference between this application example and Application Example 3 is that the separation method adopts the chromatographic packing prepared in Comparative Example 3 to make a chromatographic column, and the chromatographic packing obtained in Comparative Example 3 is prepared into a chromatographic column 7.

[0193] Other chromatographic conditions are the same as those in Application Example 3. The test target standard solution is injected according to the above chromatographic conditions, and the chromatogram is recorded. The test results of the chromatographic column 7 are shown in Figure 11 .

[0194] Figure 11 Middle peak 1 represents ofloxacin, peak 2 represents pefloxacin, peak 3 represents norfloxacin, peak 4 represents chloramphenicol, and peak 5 represents flumequine.

[0195] From Figure 11 It can be seen that, compared with Application Example 3, the raw material of the chromatographic packing of the chromatographic column 7 has no biomass and pentafluorophenylsilane, resulting in that ofloxacin, pefloxacin and norfloxacin cannot be completely separated.

[0196] Application Example 8

[0197] The difference between this application example and Application Example 4 is that the separation method adopts the chromatographic packing prepared in Comparative Example 1 to make a chromatographic column, and the chromatographic packing obtained in Comparative Example 4 is prepared into a chromatographic column 8.

[0198] Other chromatographic conditions are the same as those in Application Example 4. The test target standard solution is injected according to the above chromatographic conditions, and the chromatogram is recorded. The test results of the chromatographic column 8 are shown in Figure 12 .

[0199] Figure 12 Middle peak 1 represents cytosine, peak 2 represents uracil, peak 3 represents uridine, peak 4 represents adenine, and peak 5 represents adenosine.

[0200] From Figure 12 It can be seen that, compared with Application Example 4, the biomass and pentafluorophenylsilane in the raw material of the chromatographic packing of the chromatographic column 8 account for a small proportion, resulting in that uridine, uracil, cytosine, adenosine and adenine cannot be completely separated.

[0201] In summary, the raw material silica gel in the chromatographic packing material of the present application is simultaneously combined with biomass powder, pentafluorophenylsilane and octadecylsilane, three groups of compounds are separated by multiple retention effects such as hydrophobic retention, hydrogen bond and dipole-dipole interaction, forming a separation system with multiple retention mechanisms working together, so that the efficient separation of various types of substances can be realized on one chromatographic column, achieving accurate and effective detection and monitoring of various types of compounds, and greatly improving the application range of chromatographic separation.

[0202] The present application effectively overcomes the shortcomings in the prior art and has high industrial utilization value.

[0203] The above examples only exemplarily illustrate the principles and effects of the present application, and are not used to limit the present application. Any person skilled in the art can modify or change the above examples without departing from the spirit and scope of the present application. Therefore, all equivalent modifications or changes completed by those skilled in the art without departing from the spirit and technical thought disclosed by the present application should be covered by the claims of the present application.

Claims

1. A chromatographic packing material, characterized in that, The raw materials for the chromatographic packing include: biomass powder, pentafluorophenylsilane, octadecylsilane, and raw silica gel; the weight ratio of the biomass powder, the pentafluorophenylsilane, the octadecylsilane, and the raw silica gel is 1:(1~2):(2~2.5):(4~6). The raw materials for the biomass powder are selected from one or more of the following: camellia fruit shell, grape seeds, pomegranate seeds, and hawthorn seeds. The preparation method of the chromatographic packing material includes the following steps: mixing raw silica gel with biomass powder, pentafluorophenylsilane and octadecylsilane, and reacting to obtain the chromatographic packing material; the reaction temperature is 80~350 ℃; the reaction time is 7~40 h.

2. The chromatographic packing material according to claim 1, characterized in that, The biomass powder is defatted biomass powder, and the preparation method of the defatted biomass powder includes the following steps: mixing and soaking biomass with an organic solvent; And / or, the particle size of the biomass powder is 1.0~2.5μm; And / or, the specific surface area of ​​the biomass powder is 200~500m². 2 / g; And / or, the pentafluorophenylsilane is selected from one or more of trimethylpentafluorophenylsilane, dimethylpentafluorophenylsilane, aminodimethylpentafluorophenylsilane, trimethoxy(pentafluorophenyl)silane, pentafluorophenyldimethylchlorosilane, pentafluorophenyltriethoxysilane, pentafluorophenylethoxydimethylsilane, and pentafluorophenylpropyltrimethoxysilane; And / or, the octadecylsilane is selected from one or more of octadecyltrichlorosilane, octadecyldimethylchlorosilane, and octadecylmethyldichlorosilane; And / or, the particle size of the chromatographic packing material is 3.5 μm to 10.5 μm; And / or, the pore size of the chromatographic packing is 100~300 Å; And / or, the specific surface area of ​​the chromatographic packing is 200~500 m². 2 / g; And / or, the particle size of the raw silica gel is 1μm~8μm; And / or, the pore size of the raw silica gel is 100~300Å; And / or, the specific surface area of ​​the raw material silicone is 200~500 m². 2 / g.

3. The chromatographic packing material according to claim 2, characterized in that, The organic solvent is selected from one or both of toluene and ethanol; And / or, the solid-liquid ratio of the biomass and the organic solvent is 1 g: (7-20) mL; And / or, the soaking time is 14 to 36 hours.

4. The chromatographic packing material according to claim 3, characterized in that, The organic solvent is a mixture of toluene and ethanol, wherein the volume ratio of toluene to ethanol is (1-4):

1.

5. A method for preparing a chromatographic packing material as described in any one of claims 1 to 4, characterized in that, The preparation method includes the following steps: mixing raw silica gel with biomass powder, pentafluorophenylsilane and octadecylsilane, and reacting to obtain the chromatographic packing material.

6. The preparation method according to claim 5, characterized in that, The raw material silica gel further includes a pretreatment step before mixing, the pretreatment including mixing with one or two of toluene and / or ethanol; And / or, the preparation method is carried out under a protective atmosphere.

7. The preparation method according to claim 6, characterized in that, The pretreatment includes mixing with toluene and ethanol in a volume ratio of (1-4):1; And / or, the mixing temperature is 90~300℃; And / or, the mixing time is 0.8~6 h; And / or, the protective atmosphere is an oxygen-free atmosphere.

8. A method for separating perfluorinated / polyfluorinated compounds, or separating N-tert-butyl-4-aminobenzamide and methyl para-aminobenzoate, or separating antibiotics, or separating uracil nucleoside, uracil, cytosine, adenine nucleoside, and adenine, wherein the separation method uses a chromatographic column prepared with the chromatographic packing material as described in any one of claims 1 to 4, and the separation method comprises the following steps: adding a solution containing the target analyte to a liquid chromatograph using the chromatographic column for separation.

9. The separation method according to claim 8, characterized in that, The flow rate of the mobile phase used in the liquid chromatograph is 0.3 ~ 2 mL / min; And / or, the column temperature of the chromatographic column is 25℃~45℃; And / or, the column length of the chromatographic column is 100mm~300mm; And / or, the inner diameter of the chromatographic column is 2 mm to 10 mm; And / or, the injection volume of the liquid chromatograph is 2 μL to 20 μL.

10. The use of a chromatographic packing material as described in any one of claims 1 to 4 in the separation of perfluorinated / polyfluorinated compounds, or the separation of N-tert-butyl-4-aminobenzamide and methyl para-aminobenzoate, or the separation of antibiotics, or the separation of uracil nucleoside, uracil, cytosine, adenine nucleoside, and adenine.

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