CN114618458B - Mixed mode chromatographic stationary phase containing polycyclic aromatic hydrocarbon functional groups and preparation and application thereof - Google Patents
Mixed mode chromatographic stationary phase containing polycyclic aromatic hydrocarbon functional groups and preparation and application thereof Download PDFInfo
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J20/287—Non-polar phases; Reversed phases
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
- B01D15/325—Reversed phase
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
- B01D15/325—Reversed phase
- B01D15/327—Reversed phase with hydrophobic interaction
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/52—Sorbents specially adapted for preparative chromatography
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/80—Aspects related to sorbents specially adapted for preparative, analytical or investigative chromatography
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Abstract
The invention relates to a liquid chromatography stationary phase, which is characterized in that a bonding phase contains multi-halogen and ionizable amino and carboxyl groups, and the structural formula is as follows:wherein Silica Gel is Silica Gel, R 1 Is a C1-C10 alkyl chain, R 2 Is a C1-C10 alkyl chain, R 3 Is one of phenyl, naphthyl, anthryl and pyrenyl. The invention also provides a preparation method of the liquid chromatography stationary phase, wherein polyamino groups are introduced into the surface of silica gel, and then a novel mixed mode stationary phase containing polycyclic aromatic hydrocarbon functional groups is prepared through nucleophilic reaction. The separation material provided by the invention has novel structure, contains hydrophobic aromatic rings, has ionizable amino and carboxyl groups, has high separation selectivity, and can separate and analyze different types of samples by regulating and controlling different mobile phase conditions.
Description
Technical Field
The invention relates to a liquid chromatography stationary phase, in particular to a mixed mode chromatography stationary phase containing polycyclic aromatic hydrocarbon functional groups.
Background
Mixed-mode chromatography (MMC-mode chromatography) is a chromatographic separation technique in which two or more separation mechanisms exist simultaneously on one chromatographic column, and is a powerful tool for separating and analyzing a variety of compounds. In MMC, various acting forces exist between the fixed phase and the analyte, such as hydrophobic action, electrostatic action, hydrogen bond action, dipole-dipole action and the like, which provide better selectivity for separating various compounds simultaneously, expand the detection range of the sample, and realize separation under different modes according to the characteristics of the sample, which is very beneficial to analysis of complex samples. If the fixed phase carries alkyl chains and polar groups, hydrophobic and hydrophilic effects can be provided, and separation of reversed phase/hydrophilic (RPLC/HILIC) can be achieved, and the method can be used for analyzing polar and nonpolar substances simultaneously.
The reversed phase/ion exchange mixed mode chromatography is to introduce a polar group with electrostatic action on the surface of a reversed phase chromatography stationary phase, combine the electrostatic action with hydrophobic action, and make the separation effect different from that of the conventional common reversed phase chromatography [ McCalley D.V, J.Chromatogra.A.2007,1138,65-72]. The hydrophilic/ion exchange mixed mode chromatography can be widely applied to separation of polypeptides and proteins, and by using a polar chromatography stationary phase with charges and a mobile phase containing a high proportion of organic phase, an analysis target substance is utilized to achieve a separation effect by hydrophilic action and charge action with the stationary phase [ Hodges, R.S. et al, J.Sep. Sci,2008,31,2754-2773]. The reversed phase/hydrophilic mixed mode chromatographic stationary phase has better compatibility and stability under the condition of higher mobile phase of water phase, can well improve the peak shape of the alkaline compound, and can realize the separation of the acidic compound, the alkaline compound and the neutral compound [ Shi, Z.G.et al, anal.Chim.acta,2015,182-190].
The aryl stationary phase has good separation selectivity to neutral compounds and aromatic compounds due to the hydrophobic effect and pi-pi effect. Powell reports that selective analysis of steroids with similar relative structures based on different phenyl immobilizations shows that the stationary phase containing biphenyl ligands works best for separating steroid samples with different degrees of unsaturation, and that the separation effect of the epimers of the diphenyl immobilisation relative steroids is better than that of the biphenyl stationary phase [ Powell.M.et al, anal. Methods,2013,5,5014-5018]. Currently, there is no report of mixed mode chromatographic stationary phase containing polycyclic aromatic hydrocarbon.
Disclosure of Invention
The invention aims to provide a mixed mode chromatographic stationary phase containing polycyclic aromatic hydrocarbon and a preparation method thereof. The bonding phase contains polycyclic aromatic hydrocarbon, amino, carboxyl and amide groups, and the preparation method is simple and has wide applicability.
The technical scheme of the invention is as follows: the liquid chromatography stationary phase is characterized by comprising the following components:
wherein Silica Gel is Silica Gel, R 1 Is a C1-C10 alkyl chain, R 2 Is a C1-C10 alkyl chain, R 3 Is one of phenyl, naphthyl, anthryl and pyrenyl.
The invention also provides a preparation method of the stationary phase, which is characterized by comprising the following steps:
a. silanization: under the protection of nitrogen and/or argon, adding a polyamino silane coupling agent and microspherical silica gel dried for 8-18 hours at 120-160 ℃ into an organic solvent, reacting for 6-24 hours at 100-130 ℃, filtering, and sequentially using methanol and a volume ratio of 1-3:1, washing the solid by methanol water, methanol and tetrahydrofuran, and drying the solid in a vacuum drying oven at 40-80 ℃ for 8-24 hours to prepare polyamino silica gel;
the dosage of the silane coupling agent is 0.1-5mmol and the dosage of the organic solvent is 6-18mL per gram of silica gel;
b. nucleophilic reaction: adding organic solvent and polyaromatic hydrocarbon anhydride into the prepared polyamino silica gel, adding alkaline catalyst, reacting at 40-100 deg.c for 8-48 hr, filtering, washing with methanol, sodium acetate solution, water and methanol successively, and drying the obtained solid in a drying box at 40-80 deg.c for 8-24 hr to obtain chromatographic stationary phase.
The dosage of the polyaromatic hydrocarbon anhydride is 0.1-2.4mmol, the dosage of the organic solvent is 4-10mL, and the dosage of the alkaline catalyst is 0.1-10mmol based on each gram of polyamino silica gel.
The invention has the following advantages:
1. novel structure. The invention provides a mixed mode chromatographic stationary phase containing polycyclic aromatic hydrocarbon for the first time. The stationary phase structure contains polycyclic aromatic hydrocarbon and has ionizable amino and carboxyl groups, so that the stationary phase has various acting forces such as hydrophobic effect, pi-pi effect, electrostatic acting force, hydrogen bond acting force, dipole-dipole and the like, has good separation selectivity for most natural products and medicines, and can be widely used for separation analysis and purification preparation of various samples.
2. The preparation process of the liquid chromatography stationary phase provided by the invention is simple and reliable, and is favorable for realizing industrialization.
Drawings
FIG. 1 is a chromatogram of example 5.
Detailed Description
The invention is further illustrated by the following examples. The examples are only illustrative of the invention and are not intended to be limiting.
Example 1
10g of microspheroidal silica gel (particle size 3.5 μm, pore size 10 nm) dried at 160℃for 16 hours, 6mL of N- (2-aminoethyl) -aminopropyl trimethoxysilane and 60mL of xylene were added to a 100mL flask under nitrogen protection, reacted at 110℃for 16 hours, filtered, and successively reacted with methanol in a volume ratio of 1:1, methanol water, methanol and tetrahydrofuran, and drying the obtained solid in a drying oven at 80 ℃ for 12 hours to prepare the N- (2-aminoethyl) -aminopropyl silica gel.
To a 250mL flask, 10g of amino silica gel, 3g of 4-dimethylaminopyridine, 2.4g of 1, 8-naphthalenedicarboxylic anhydride (molar number: 12 mmol) and 100mL of N, N-dimethylformamide were added to react at 60℃for 24 hours, and filtration was carried out, and the obtained solid was washed with methanol, 60mM sodium acetate solution, water and methanol in this order, and dried at 80℃for 16 hours in a drying oven to obtain a chromatographic stationary phase 1 having the following structure:
example 2
10g of microspheroidal silica gel (particle size 2.5 μm, pore size 10 nm) dried at 160℃for 16 hours, 6mL of N- (2-aminoethyl) -aminopropyl trimethoxysilane and 60mL of xylene were added to a 100mL flask under nitrogen protection, reacted at 80℃for 24 hours, filtered, and successively reacted with methanol in a volume ratio of 3:1, methanol water, methanol and tetrahydrofuran, and drying the obtained solid in a drying oven at 80 ℃ for 16 hours to prepare the N- (2-aminoethyl) -aminopropyl silica gel.
To a 250mL flask, 10g of amino silica gel, 5mL of pyridine, 3.6g of 1, 10-pyrenedioic anhydride (molar number: 20 mmol) and 100mL of N, N-dimethylformamide were added to react at 40℃for 24 hours, and filtration was performed, and the obtained solid was washed with methanol, 50mM sodium acetate solution, water, methanol in this order, and dried at 80℃for 24 hours in a dry box to obtain a chromatographic stationary phase 2 having the following structure:
example 3
The procedure and conditions were the same as in example 2, except that 1, 10-anthracene-dicarboxylic anhydride (molar number: 18 mmol) was used instead of 1, 10-pyrene-dicarboxylic anhydride (molar number: 20 mmol), to obtain a chromatographic stationary phase 3, which had the following structure:
example 4
To a 100mL flask under nitrogen protection, 10g of microspheroidal silica gel (particle size: 5 μm, pore diameter: 10 nm) dried at 160℃for 16 hours, 8mL of N- (2-aminohexyl) -aminopropyl trimethoxysilane and 60mL of xylene were added, reacted at 110℃for 16 hours, filtered, washed sequentially with methanol, methanol water, methanol and tetrahydrofuran, and the obtained solid was dried at 80℃for 16 hours in a dry box to prepare N- (2-aminohexyl) -aminopropyl silica gel.
To a 250mL flask, 10g of amino silica gel, 3mL of 1, 5-diazabicyclo [4.3.0] non-5-ene, 2.4g of 1, 8-naphthalene dicarboxylic anhydride (molar number: 12 mmol) and 100mL of dimethyl sulfoxide were added to react at 40℃for 48 hours, and filtration was carried out, followed by washing with methanol, 50mM sodium acetate solution, water and methanol, and the obtained solid was dried at 80℃for 16 hours in a drying oven to obtain a chromatographic stationary phase 4 having the following structure:
example 5
The chromatographic stationary phase 1 obtained in example 1 was used to pack a 4.6X50 mm column for separation analysis of neutral compounds, and the stationary phase had good selectivity to neutral compounds. As shown in fig. 1, the chromatographic conditions are:
chromatographic column: 4.6X150 mm;
sample: neutral compound mix (uracil 1mg/mL, nitrobenzene 1mg/mL, naphthalene 2mg/mL, fluorene 2.2 mg/mL);
solvent: a: acetonitrile, B:1, water;
eluting: a: b=50: 50 (V/V);
flow rate: 1.5mL/min;
column temperature: 30 ℃;
detection wavelength: PDA (190 nm-400 nm) & UV (254 nm);
example 6
Different types of chromatographic stationary phases are used for filling a 4.6X50 mm chromatographic column for separation analysis of flavonoid compounds. The test results are shown in the following table, and the chromatographic conditions are:
chromatographic column: 4.6X150 mm;
sample: mixing (rutin 0.13mg/mL, orange peel 0.25 mg/mL);
solvent: a: acetonitrile, B:0.1% phosphoric acid water;
eluting: 0-10-15 min, 5-30-90% A;
flow rate: 1.5mL/min;
column temperature: 30 ℃;
detection wavelength: PDA (190 nm-400 nm) & UV (254 nm);
rutin is flavonoid, and hesperidin is dihydroflavonoid. The stationary phase A prepared in the example 1 has an aromatic ring structure, pi-pi acting force exists, and the retention of a compound containing a conjugated structure can be increased, so that rutin has better separation selectivity because the retention time of one conjugated structure in the stationary phase A is longer than that of hesperidin.
Example 7
Different types of chromatographic stationary phases were used to pack 4.6x50 mm chromatographic columns for separation analysis of saponin compounds. The test results are shown in the following table, and the chromatographic conditions are:
chromatographic column: 4.6X150 mm;
sample: mixing (ginsenoside Rb 2.3.0 mg/mL, saikosaponin d 2.0 mg/mL);
solvent: a: acetonitrile, B: water;
eluting: gradient is 0-10-15 min, 20-50-90% A;
flow rate: 1.0mL/min;
column temperature: 30 ℃;
detection wavelength: PDA (190 nm-400 nm) & UV (203 nm);
the stationary phase A prepared in example 1 has pi-pi acting force due to the aromatic ring structure, has longer retention time on a saikosaponin d sample containing a benzene ring structure, and has better separation selectivity with ginsenoside Rb 2.
Example 8
Different types of chromatographic stationary phases are used to pack 4.6X50 mm chromatographic columns for separation analysis of flavonols and tryptophane indole alkaloid compounds. The test results are shown in the following table, and the chromatographic conditions are:
chromatographic column: 4.6X150 mm;
sample: mixing (quercetin 0.06mg/mL, evodiamine 0.38 mg/mL);
solvent: a: acetonitrile, B:0.1% phosphoric acid water;
eluting: 0-10-15 min, 5-30-90% A;
flow rate: 1.5mL/min;
column temperature: 30 ℃;
detection wavelength: PDA (190 nm-400 nm) & UV (254 nm);
the stationary phase A prepared in the example 1 has pi-pi acting force due to the aromatic ring structure, has longer retention of quercetin with conjugated structure than other two stationary phases, and has better separation selectivity with evodiamine.
Claims (8)
1. An application of a mixed mode chromatographic stationary phase containing polycyclic aromatic hydrocarbon functional groups in a chromatographic separation process is characterized in that: the chromatographic separation mode is reversed phase chromatographic separation and ion exchange separation, and the bonding phase contains multiple aromatic rings and ionizable amino and carboxyl groups; the structural formula is as follows:
wherein Silica Gel is Silica Gel, R 1 Is a C1-C10 alkyl chain, R 2 Is a C1-C10 alkyl chain, R 3 Is one or more of phenyl, naphthyl, anthryl and pyrenyl, wherein the chromatographic separation comprises hesperidin and rutin chromatographic separation, ginsenoside Rb2 and saikosaponin d chromatographic separationSeparating the quercetin from evodiamine by chromatography.
2. The use according to claim 1, characterized in that: each gram of silica gel contains 0.1-2.4mmol R 3 。
3. The use according to claim 1, wherein the stationary phase is prepared by a process comprising the steps of:
silanization: under the protection of nitrogen and/or argon, adding a polyamino silane coupling agent and microspherical silica gel dried for 8-18 hours at 120-160 ℃ into an organic solvent, reacting for 6-24 hours at 100-130 ℃, filtering, and sequentially using methanol and a volume ratio of 1-3:1, washing the solid by methanol water, methanol and tetrahydrofuran, and drying the solid in a vacuum drying oven at 40-80 ℃ for 8-24 hours to prepare polyamino silica gel;
nucleophilic reaction: adding organic solvent and polyaromatic hydrocarbon anhydride into the prepared polyamino silica gel, adding alkaline catalyst, reacting at 40-100 deg.c for 8-48 hr, filtering, washing with methanol, sodium acetate solution, water and methanol successively, and drying the obtained solid in a drying box at 40-80 deg.c for 8-24 hr to obtain chromatographic stationary phase.
4. A use according to claim 3, characterized in that: the silane coupling agent used in the step a has the following structure:
wherein X is one or more than two of chlorine atom, methoxy or ethoxy, R 1 Is a C1-C10 alkyl chain, R 2 Is a C1-C10 alkyl chain.
5. A use according to claim 3, characterized in that: the organic solvent used in the step a is one or more than two of o-dichlorobenzene, chlorobenzene, toluene, xylene, n-heptane and isooctane;
the organic solvent used in the step b is one or more of N, N-dimethylformamide, acetonitrile, toluene, xylene and dimethyl sulfoxide.
6. A use according to claim 3, characterized in that: the polyaromatic hydrocarbon anhydride containing structure used in step b is:
wherein R is 3 Is one or more of phenyl, naphthyl, anthryl and pyrenyl.
7. A use according to claim 3, characterized in that: the alkaline catalyst used in the step b is one or more than two of ammonium bicarbonate, sodium bicarbonate, 1, 8-diazabicyclo [5,4,0] undec-7, 1, 5-diazabicyclo [4.3.0] non-5-ene, N-lutidine, pyridine and imidazole.
8. Use according to any of claims 3-7, characterized in that:
the amount of the organic solvent used in the step a is 6-18mL per gram of silica gel;
the dosage of the polyamino silane coupling agent used in the step a is 0.1-5mmol of the polyamino silane coupling agent per gram of silica gel;
the amount of the organic solvent used in the step b is 4-10mL per gram of polyamino silica gel;
the dosage of the polyaromatic hydrocarbon anhydride used in the step b is 0.1-2.4mmol of polyamino silica gel per gram;
the basic catalyst used in step b is used in an amount of 0.1 to 10mmol per gram of polyamino silica gel.
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| US4604207A (en) * | 1982-05-19 | 1986-08-05 | Sumitomo Chemical Co., Ltd. | Packing materials for chromatographic use and a method for analysis of an enantiomer mixture using the same |
| CN102091596A (en) * | 2011-01-07 | 2011-06-15 | 郑州大学 | Benzoyl calixarene bonded silica gel stationary phase, preparation method and application thereof |
| WO2012100592A1 (en) * | 2011-01-28 | 2012-08-02 | 中国科学院大连化学物理研究所 | Zwitterionic hydrophilic chromatography stationary phase and manufacturing method thereof |
| CN103170311A (en) * | 2013-03-20 | 2013-06-26 | 华东理工大学 | Novel amino serial chromatographic support and preparation method |
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| US7045059B2 (en) * | 2003-07-28 | 2006-05-16 | Sielc Technologies Corp | Universal bonded phase material for chromatographic separation |
| CN103301822B (en) * | 2012-10-25 | 2016-08-03 | 中国人民解放军第四军医大学 | A kind of polar liquid chromatogram filler and preparation method thereof |
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|---|---|---|---|---|
| US4604207A (en) * | 1982-05-19 | 1986-08-05 | Sumitomo Chemical Co., Ltd. | Packing materials for chromatographic use and a method for analysis of an enantiomer mixture using the same |
| CN102091596A (en) * | 2011-01-07 | 2011-06-15 | 郑州大学 | Benzoyl calixarene bonded silica gel stationary phase, preparation method and application thereof |
| WO2012100592A1 (en) * | 2011-01-28 | 2012-08-02 | 中国科学院大连化学物理研究所 | Zwitterionic hydrophilic chromatography stationary phase and manufacturing method thereof |
| CN103170311A (en) * | 2013-03-20 | 2013-06-26 | 华东理工大学 | Novel amino serial chromatographic support and preparation method |
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