CN113075346A - Gas chromatography separation analysis method based on aromatic macrocycle, molecular cage and pillar quinone and application - Google Patents
Gas chromatography separation analysis method based on aromatic macrocycle, molecular cage and pillar quinone and application Download PDFInfo
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Abstract
The invention discloses a gas chromatography separation and analysis method and application based on aromatic macrocycles, molecular cages and cylindroquinones. It mainly coats aromatic macrocycle and column quinone in capillary gas chromatographic column as fixed phase to realize high resolution gas chromatographic analysis. According to different filled stationary phases, the analysis and detection of various small molecules which are difficult to separate can be realized. The invention has the advantages that: the raw materials of the aromatic macrocycle and the cylindroquinone can be purchased commercially, the synthesis is simple and convenient, the yield is high, the modification is convenient, the stationary phase can be adjusted according to the structure of a target isolate, the high-efficiency gas chromatography separation analysis is realized, and the method has wide application prospects in the aspects of material identification, purity analysis, environmental protection, food safety, quality control and the like.
Description
Technical Field
The invention belongs to the application of supermolecule macrocycles and molecular cages in gas chromatographic separation, and particularly relates to a gas chromatographic separation analysis method and application based on aromatic macrocycles and column quinones.
Background
Classical macrocyclic molecules (crown ethers, cyclodextrins, calixarenes, cucurbiturils, etc.) are essential for recognition and assembly, and exhibit a wide range of applications in chemistry, materials and biology. Their widespread use makes the synthesis of new macrocycles very attractive. Various novel macrocycles are successively synthesized by chemists, such as texas rings, ExBox, pillararene, chikurea, pillared complexes, cycloparaphenylene, calixazole, calixarene, cyanostar, and the like. Recently we have applied for a new class of macrocyclic synthetic patents, however, their functional development has just started; on the other hand, the interdisciplinary crossing often brings new breakthrough and discovery, and the separation and analysis of compounds with similar polarity, structure and physicochemical properties, which troubles the analysis field for a long time, is a problem to be solved. Therefore, the synthesis of new compounds easy to modify and derive, and the combination with an instrumental analysis method to realize the high-efficiency separation and detection of similar analytes have important theoretical significance and application value.
Disclosure of Invention
The invention aims to provide an efficient and universal gas chromatography separation and analysis method based on aromatic macrocycle and column quinone aiming at the problems of difficult separation, analysis and detection, high price and the like of a commercialized chromatographic column caused by similar structure, similar polarity and small physicochemical property difference of micromolecular aromatic isotopologues and the like, and the method is used for separation and detection of benzene and cyclohexane which need to be solved urgently in industry and analysis and detection application of important organic chemical raw materials halogenated aromatic hydrocarbon. According to the method, the aromatic macrocycle and the quinone column are used as the stationary liquid of the capillary gas chromatographic column, a series of capillary columns are prepared, effective analysis and separation of aromatic hydrocarbons and alkanes with similar properties are achieved, the raw material sources of the capillary column stationary liquid are remarkably expanded, and the analysis and separation performance of the capillary columns is improved.
In order to achieve the purpose, the invention discloses the following technical scheme:
a gas chromatography separation and analysis method based on aromatic macrocycles, molecular cages and pillar quinones is characterized by comprising the following steps: :
(1) a gas chromatographic separation and analysis method based on the column aromatic hydrocarbon compound;
(2) a gas chromatographic separation analysis method based on the column quinone compound;
(3) a gas chromatographic separation analysis method based on biphenyl aromatic macrocyclic and cage-shaped molecular compounds; wherein:
(1) the gas chromatographic separation and analysis method based on the column aromatic hydrocarbon compound comprises the following steps:
grinding the column [5] arene or column [6] arene compound solid into superfine powder, dispersing the superfine powder in a methanol/ethanol/acetone/tetrahydrofuran/dioxane solvent to be used as a stationary liquid, filling the fixed liquid into a capillary tube which is 5-100 meters in length and 0.1-0.5 mm in inner diameter through filling equipment by a dynamic coating method, and removing the solvent by using nitrogen to obtain a capillary chromatographic column; installing the capillary chromatographic column on a gas chromatograph, analyzing and detecting benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene;
the structure of the column [5] arene or the column [6] arene is as follows:
(2) the gas chromatographic separation and analysis method based on the column quinone compound is as follows:
grinding the solid of the quinone compound of the column [5] into superfine powder, dispersing the superfine powder in a methanol/ethanol/acetone/tetrahydrofuran/dioxane/dichloromethane/chloroform/acetonitrile solvent to be used as a stationary liquid, filling the stationary liquid into a capillary tube which is 5-100 meters in length and 0.1-0.5 mm in inner diameter by a filling device by a dynamic coating method, and removing the solvent by nitrogen to obtain a capillary chromatographic column;
installing the capillary chromatographic column on a gas chromatograph, analyzing and detecting benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene;
the column [5] holoquinone compound:
(3) the gas chromatographic separation and analysis method based on the biphenyl aromatic macrocyclic and cage-shaped molecular compounds comprises the following steps:
grinding the biphenyl aromatic macrocycle and the cage-shaped molecular compound solid into superfine powder, dispersing the superfine powder in a methanol/ethanol/acetone/tetrahydrofuran/dioxane solvent to be used as a stationary liquid, loading the stationary liquid into a capillary tube which is 5-100 meters in length and 0.1-0.5 mm in inner diameter by a dynamic coating method through filling equipment, and removing the solvent by using nitrogen to obtain a capillary chromatographic column; installing the capillary chromatographic column on a gas chromatograph, analyzing and detecting benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene;
the biphenyl aromatic hydrocarbon macrocyclic and cage-shaped molecular compound is as follows:
the invention further discloses application of the gas chromatography separation and analysis method based on the aromatic macrocycle and the cylindroquinone in the aspects of materials, environment and biology. The cyclic [5] holoquinone compound is used for detecting important organic chemical raw materials of o/m/p-dichlorobenzene, o/m/p-dibromobenzene and o/m/p-diiodobenzene. The experimental result shows that 5.54 min of o-dichlorobenzene appears, 5.64 min of m-dichlorobenzene appears, 6.34 min of o-dibromobenzene appears, 6.61 min of dibromobenzene appears, the retention time of four halogenated aromatic hydrocarbons is less than 7min, and the rapid separation is realized; and effective separation of four compounds of o-dichlorobenzene, m-dichlorobenzene, o-dibromobenzene and m-dibromobenzene is realized by one-time sample injection, and effective separation and detection of halogenated aromatic hydrocarbon are realized, which cannot be realized by a common capillary gas chromatographic column (figure 2). The biphenyl aromatic macrocycle and the cage-shaped molecular compound are mainly used for efficiently separating and detecting benzene and cyclohexane. Experimental results show that the capillary column filled with Cage3 has short retention time for cyclohexane and benzene, the peak appears at 4.50 min and at 4.60 min, and the peaks appear obviously, so that effective separation and detection of benzene and cyclohexane are realized, and the problem of difficult separation and detection of cyclohexane and benzene is solved (figure 1).
The invention discloses a gas chromatography separation and analysis method based on aromatic macrocycles and pillar quinones, which mainly comprises the following steps: a column [5] arene, a methyl column [5] arene, an ethyl column [5] arene, a column [6] arene, a methyl column [6] arene, an ethyl column [6] arene, a column [5] holoquinone, a bis- (2, 4-dimethoxyphenyl) arene macrocycle (benzene, tetrafluorobenzene, biphenyl, dimethylbiphenyl, octafluorobiphenyl, terphenyl, quaterphenyl, naphthalene, anthracene, anthraquinone, pyrene, porphyrin, fluorenone, carbazole and modified carbazoles, benzothiadiazole, styrene, antisiphenyl, tetrafluorobenzene, tetraphenylene, diphenylpropanedione, fluoroborol, and the like), a perhydroxyquaterphenyl macrocycle, a perhydroxynaphthalene macrocycle, an ammonium naphthoate macrocycle, or tris- (2, 4-dialkoxyphenyl) arene (benzene, mesitylene) cages, perhydroxytris- (2, 4-dialkoxyphenyl) arene cages and the like. The compounds are coated in a capillary gas chromatographic column to be used as a stationary phase, and various micromolecules which are difficult to separate can be analyzed and detected according to different filled stationary phases, so that high-resolution gas chromatographic analysis is realized. According to the invention, the detection application of the benzene and the cyclohexane as well as the important organic chemical raw materials of the o/m/p-dichlorobenzene, the o/m/p-dibromobenzene and the o/m/p-diiodobenzene is realized. The invention has the advantages that: the raw materials of the aromatic macrocycle and the cylindroquinone can be purchased commercially, the synthesis is simple and convenient, the yield is high, the modification is convenient, the stationary phase can be adjusted according to the structure of a target isolate, the high-efficiency gas chromatography separation analysis is realized, and the method has wide application prospects in the aspects of material identification, purity analysis, environmental protection, food safety, quality control and the like.
Drawings
FIG. 1: gas chromatogram of Cage3 separating benzene and cyclohexane;
FIG. 2: column 5 quinone gas chromatograms of the separation of o/m-dichlorobenzene and o/m-dibromobenzene.
[ detailed description ] embodiments
The present invention will be described in detail with reference to the accompanying drawings, but the present invention is not limited to the following examples. Specific details are set forth in order to provide a thorough understanding of the present invention in the preferred embodiments thereof. The starting materials used in the invention are commercially available, the preparation method is disclosed in the claim protection of the unreported compound, and the reported compound is illustrated in the specification and added with a cited literature, so that the description is provided.
Example 1
The gas chromatographic separation and analysis method of the aromatic macrocycle and the pillar quinone comprises the following steps:
step 1, synthesis of aromatic macrocycles and cylindroquinones;
step 3, analyzing and separating related compounds by a gas chromatographic column based on aromatic macrocycles and quinone columns.
Step 1 the synthetic method of the aromatic macrocycle and the cylindroquinone is as follows:
【1】 Preparation of column [5] arene and column [6] arene
(1) Preparation of column [5] arene and methyl column [5] arene
According to the literature (Tomoki Ogoshi, Suguru Kanai, Shuhei Fujinami, Tada-aki Yamagishi, and Yoshiaki Nakamoto.J. Am. Chem. Soc. 2008, 130, 5022–5023.) The synthesis gives the column [5]]Aromatic and methyl column [5]]An aromatic hydrocarbon.
(2) Preparation of ethyl column [5] arene, methyl column [6] arene and ethyl column [6] arene
According to literature (Cao, d., Kou, y., Liang, j., Chen, z., Wang, l. and Meier, H).Angewandte Chemie International Edition, 2009, 489721-9723.) Synthesis of Ethyl column [5]]Arene methyl column [6]Aromatic and ethyl column [6]]An aromatic hydrocarbon.
(3) Preparation of column [6] arenes
According to the literature (Yingjie Ma, Xiaodong Chi, Xuzhou Yan, Jiyong Liu, Yong Yao, Weixiang Chen, Feihe Huang, and Jun-Li Hou.Org. Lett. 2012, 141532-1535.) Synthesis to give column [6]]An aromatic hydrocarbon.
【2】 Preparation of column [5] holoquinone
According to the literature (Kilingaruu I. Shivakumar, Gangadhar J. Sanjayan.Synthesis, 2013, 45896-898.) was synthesized to obtain a column [5]]All-quinone.
【3】 Preparation of biphenyl arene macrocyclic and cage-like molecular compound
(1) Preparation of LC1-LC8, LC11-41, Cage1-4
According to the patent (Li Chun, Xukedi, Zhang Yuan, a kind of large ring and Cage-shaped molecules based on biphenyl arene and derivative compounds and synthesis method and application thereof, application No. 201910975631.8, application publication No. CN 110642684A), the biphenyl arene large ring and molecular Cage LC1-LC8, LC11-41 and Cage1-4 are synthesized.
(2) Preparation of LC9
According to the literature (y, Wang,# K. Xu,# B. Li, L. Cui, J. Li, X. Jia, H. Zhao, J. Fang, C. Li. Angew. Chem. Int. Ed. 2019, 5810281-10284.) to give the biphenyl aromatic macrocycle LC 9.
(3) Preparation of LC10
The biphenyl aromatic macrocycle LC10 is synthesized according to the patent (Livernet, Jomonte, Traude, Jia academic cis, small molecule blue light material and the preparation method thereof, application No. 201810430120.3, application publication No. CN 108893105A).
biphenylarene macrocyclic and caged molecular compounds (LC1-40, Cage1-4) or pillared arenes (pillared 5, methyl pillared 5, ethyl pillared 5, pillared 6, methyl pillared 6, ethyl pillared 6) or pillared 5 perquinone solids are ground to a very fine powder and dispersed in methanol, ethanol, acetone, tetrahydrofuran, dioxane, dichloro/bromomethane, trichloro/bromomethane, carbon tetrachloride, dichloro/bromoethane, trichloro/bromoethane, tetrachloro/bromoethane, monochloropropane, monochlorobutane, monochlorobromopentane, monochlorobromohexane solvents as a fixative and loaded by dynamic coating through a loading apparatus into pretreated capillaries having a length of 30 meters and an inner diameter of 0.25 mm. The solvent was removed with nitrogen to obtain a capillary gas chromatography column.
Step 3, the method for analyzing and separating related compounds by using the gas chromatographic column based on the aromatic macrocycle and the hydroquinone comprises the following steps:
the capillary gas chromatographic column was set up on a gas chromatograph, and an appropriate solvent was selected as a mobile phase to analyze and detect benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene (tables 1 and 2).
TABLE 1
TABLE 2
Example 2
The gas chromatographic separation and analysis method of the aromatic macrocycle and the pillar quinone is applied to the aspects of materials, environment and biology.
(1) Application of biphenyl aromatic hydrocarbon molecular cage as separation material in aspect of analyzing and detecting cyclohexane and benzene
Cyclohexane is a common industrial raw material and is an extremely important organic solvent, almost all cyclohexane is prepared by pure benzene hydrogenation at present, because the boiling points of cyclohexane (boiling point 80.7 ℃) and benzene (boiling point 80.1 ℃) are extremely close, the cyclohexane and the benzene are difficult to separate by a common gas chromatographic column, the purity detection is difficult, and the high-purity cyclohexane has great demands in a plurality of important fields, so that the development of a universal and effective separation detection method for detecting the cyclohexane and the benzene has great application value and theoretical significance. The method comprises preparing capillary gas chromatographic column from Cage3 as stationary phase by the above method, and mounting on gas chromatograph, wherein the column temperature is 90 deg.C, the mobile phase is mixture of benzene and cyclohexane in equal proportion, and the carrier gas is helium. As can be seen from figure 1, the retention time of cyclohexane and benzene is very short, the peak appears at 4.50 min and at 4.60 min, and the peaks are obviously separated, so that the effective separation and detection of benzene and cyclohexane are realized, and the problem of difficult separation and detection of cyclohexane and benzene is solved.
(2) Application of cylindroquinone as separation material in aspect of analyzing and detecting halogenated aromatic hydrocarbon
O/m-dichlorobenzene and o/m-dibromobenzene are important organic chemical intermediates, wherein the o-dichlorobenzene is a raw material of pesticide trichloroinsecticidal ester on pesticides and is used for synthesizing an intermediate 1- (3, 4-dichlorophenyl) -2, 2, 2-trichloroethanol, and can also be used for synthesizing another important pesticide intermediate o-phenylenediamine, and in addition, the o-dichlorobenzene is also used as a solvent for operations of dyes, medicines, resins, rubber and the like, or used as a rust remover, a degreasing agent and the like; m-dichlorobenzene is an important organic synthetic raw material, is a raw material of fungicide imazalil, propiconazole and etaconazole, is a raw material of pesticide chlorfenvinphos, and is an intermediate of broad-spectrum antifungal drug miconazole. Because m-dichlorobenzene has a boiling point of 172-173 ℃, o-dichlorobenzene has a boiling point of 179 ℃, and the two have similar polarities and structures, the two are difficult to identify on analysis and detection. Similar is true for ortho/meta/para dibromobenzene. Therefore, the high performance gas chromatography analysis and detection of mixed component sample injection and one-time separation are successfully realized by using the volume selectivity and the polarity selectivity of the column 5 quinone to the halogenated aromatic hydrocarbon. Taking the column 5 quinone as a stationary phase, preparing a capillary gas chromatographic column according to the method, and installing the capillary gas chromatographic column on a gas chromatograph, wherein the column temperature is 150 ℃, the mobile phase is dichloromethane, and the carrier gas is helium. From fig. 2, it can be seen that 5.54 min o-dichlorobenzene, 5.64 min m-dichlorobenzene, 6.34 min o-dibromobenzene, 6.61 min m-dibromobenzene, and the retention time of four kinds of halogenated aromatic hydrocarbons is less than 7min, so that the rapid separation is realized; and effective separation of four compounds of o-dichlorobenzene, m-dichlorobenzene, o-dibromobenzene and m-dibromobenzene is realized by one-time sample injection, and effective separation and detection of halogenated aromatic hydrocarbon are realized, which cannot be realized by a common capillary gas chromatographic column.
Claims (4)
1. A gas chromatography separation and analysis method based on aromatic macrocycles, molecular cages and pillar quinones is characterized by comprising the following steps:
(1) a gas chromatographic separation and analysis method based on the column aromatic hydrocarbon compound;
(2) a gas chromatographic separation analysis method based on the column quinone compound;
(3) a gas chromatographic separation analysis method based on biphenyl aromatic macrocyclic and cage-shaped molecular compounds; wherein:
(1) the gas chromatographic separation and analysis method based on the column aromatic hydrocarbon compound comprises the following steps:
grinding the column [5] arene or column [6] arene solid into superfine powder, dispersing the superfine powder in a methanol/ethanol/acetone/tetrahydrofuran/dioxane solvent to be used as a stationary liquid, filling the fixed liquid into a capillary tube which is 5-100 meters in length and 0.1-0.5 mm in inner diameter by a filling device by a dynamic coating method, and removing the solvent by nitrogen to obtain a capillary chromatographic column; installing the capillary chromatographic column on a gas chromatograph, analyzing and detecting benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene;
the column [5] arene or the column [6] arene is as follows:
(2) the gas chromatographic separation and analysis method based on the column quinone compound is as follows:
grinding the solid of the quinone compound of the column [5] into superfine powder, dispersing the superfine powder in a methanol/ethanol/acetone/tetrahydrofuran/dioxane/dichloromethane/chloroform/acetonitrile solvent to be used as a stationary liquid, filling the stationary liquid into a capillary tube which is 5-100 meters in length and 0.1-0.5 mm in inner diameter by a filling device by a dynamic coating method, and removing the solvent by nitrogen to obtain a capillary chromatographic column;
installing the capillary chromatographic column on a gas chromatograph, analyzing and detecting benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene;
the column [5] holoquinone compound:
(3) the gas chromatographic separation and analysis method based on the biphenyl aromatic macrocyclic and cage-shaped molecular compounds comprises the following steps:
grinding the biphenyl aromatic macrocycle and the cage-shaped molecular compound solid into superfine powder, dispersing the superfine powder in a methanol/ethanol/acetone/tetrahydrofuran/dioxane solvent to be used as a stationary liquid, loading the stationary liquid into a capillary tube which is 5-100 meters in length and 0.1-0.5 mm in inner diameter by a dynamic coating method through filling equipment, and removing the solvent by using nitrogen to obtain a capillary chromatographic column; installing the capillary chromatographic column on a gas chromatograph, analyzing and detecting benzene/cyclohexane/fluorobenzene/chlorobenzene/bromobenzene/iodobenzene, toluene/methylcyclohexane, o/m/p-xylene, mono/m/mesitylene, o/m/p-difluorobenzene, o/m/p-dichlorobenzene, o/m/p-dibromobenzene, o/m/p-diiodobenzene/o-bromoiodobenzene, o/m/p-ethyltoluene;
the biphenyl aromatic hydrocarbon macrocyclic and cage-shaped molecular compound is as follows:
2. the method of claim 1, wherein the method is applied to materials, environment and biology.
3. The use according to claim 2, wherein the column [5] holoquinone compound is used for detection of important organic chemical raw materials of o/m/p-dichlorobenzene, o/m/p-dibromobenzene and o/m/p-diiodobenzene.
4. The use as claimed in claim 2, wherein the biphenyl aromatic macrocyclic and cage molecular compounds are mainly used for the efficient separation and detection of benzene and cyclohexane.
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| CN115636737A (en) * | 2022-09-30 | 2023-01-24 | 洛阳师范学院 | Alkyl functionalized column hexaaromatic hydrocarbon stationary phase, capillary gas chromatographic column, and preparation method and application thereof |
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