A novel capillary gas chromatography column based on triazine derivatives as the stationary phase

By using triazine derivatives as stationary phase in gas chromatography columns, the problem of difficulty in separating different polar components and difficult isomers in the prior art is solved, and efficient separation effect is achieved and has broad application prospects.

CN119574751BActive Publication Date: 2025-06-27RUIHENG (TIANJIN) BIOCHEMICAL TECHNOLOGY CO LTD
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Patent Information

Application Number
CN202510116623.3
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2025-01-24
Publication Date
2025-06-27
Estimated Expiration
2045-01-24

AI Technical Summary

Technical Problem

The existing gas chromatographic stationary phases are difficult to efficiently separate different polar components and difficult-to-separate position isomers, which limits the development of environmental analysis and petrochemical industries.

Method used

The triazine derivatives are used as the stationary phase and the inner wall of the quartz capillary column is coated on the static method to form a new capillary gas chromatography column. Combined with the program heating and aging technology, the separation performance of the chromatographic column is improved.

Benefits of technology

The excellent separation effect of alkane homologs, trichlorobenzene + tritoluene, and isomers such as alcohols and phenols that are difficult to separate are achieved, and the separation ability and flexibility of gas chromatography are significantly improved.

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Abstract

The present invention discloses a novel capillary gas chromatography column based on a triazine derivative as the stationary phase. A stationary phase containing a triazine derivative is coated on the inner wall of a quartz capillary column. The preparation method of the novel capillary gas chromatography column based on a triazine derivative as the stationary phase of the present invention includes the following steps: (1) pretreatment of the quartz capillary column; (2) coating of the stationary phase; (3) aging of the chromatographic column. The novel capillary gas chromatography column based on a triazine derivative as the stationary phase of the present invention has good inertness and good thermal stability, and can be used for the separation of components with different polarities such as alcohols, aromatics, phenols and their isomers, and is particularly suitable for the effective separation of difficult-to-separate isomers such as phenols and alcohols, and has good application prospects.
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Description

Technical Field

[0001] The present invention relates to the field of analytical chemistry, and particularly to a novel capillary gas chromatography column based on triazine derivatives as a stationary phase and a preparation method thereof. Background Art

[0002] With the development of social economy, environmental analysis, petrochemical industry and other fields play important roles. However, the effective separation and detection of different polar components (weakly polar, polar, weakly acidic and weakly basic compounds) to some extent restrict the development of environmental analysis, petrochemical industry and other fields. Gas chromatography is a modern separation and detection method, which has the characteristics of high separation efficiency, fast separation speed, small sample consumption, good selectivity and high detection sensitivity, and has wide applications in the fields of food, environment, chemical industry, etc. Its main component structure is the chromatographic column, and the selection of the chromatographic column is one of the important technologies of this analytical method. The separation and detection of different types of components often require the selection of chromatographic columns with different polar stationary phases. Therefore, the development and research of chromatographic stationary phases have always been an important research direction in the field of gas chromatography.

[0003] Currently, the existing commercial gas chromatography stationary phases mainly include polysiloxanes, polyethylene glycols and cyclodextrins. Different polar polysiloxane stationary phases are mainly suitable for the separation and detection of non-polar, weakly polar and medium polar components; polyethylene glycol stationary phases are suitable for the separation and detection of polar components; cyclodextrin stationary phases are mainly applied to the separation and detection of difficult-to-separate position isomers and chiral samples. These three major types of stationary phases can basically meet the separation and detection needs in the fields of science and actual production, and each has its own advantages. However, with the continuous synthesis and discovery of compounds, the separation and detection of different polar components exposed to the environment often require the use of chromatographic columns with different polarities to complete. Developing a chromatographic stationary phase that is suitable for separating complex systems of different polar components and is also suitable for separating challenging position isomers has great application value. Summary of the Invention

[0004] The technical problem to be solved by the present invention is to provide a novel capillary gas chromatography column based on triazine derivatives as a stationary phase, namely the TAPT chromatographic column, which has low cost and is easy to operate.

[0005] The present invention also provides a preparation method of the novel capillary gas chromatography column based on triazine derivatives as a stationary phase.

[0006] For the novel capillary gas chromatography column based on triazine derivatives as a stationary phase of the present invention, a stationary phase containing triazine derivatives is coated on the inner wall of the quartz capillary column.

[0007] The preparation method of the novel capillary gas chromatography column based on triazine derivatives as a stationary phase of the present invention includes the following steps:

[0008] (1) Pretreatment of the quartz capillary column;

[0009] (2) Coating of the stationary phase;

[0010] (3) Aging of the chromatographic column.

[0011] The preparation method described in the present invention, wherein step (1) specifically includes the following method: Take a quartz capillary column with an inner diameter of 0.25 mm and a length of 5 m, rinse it with dichloromethane for 20 min, and age it at 260 °C for 3 h under a nitrogen atmosphere: Weigh 1.31 g of NaCl and place it in 10 mL of anhydrous methanol, stir strongly for 45 min, take 6 mL of the supernatant and add it to 8 mL of a strongly stirred chloroform solution, add 0.6 mL of methanol and stir for 5 min, then add 8 mL of chloroform and stir for 2 min to obtain a saturated NaCl solution; Use a manual syringe or a method of pressurizing through a gas chromatograph injection port to make the saturated NaCl solution pass through the aged quartz capillary column, immerse the outlet end of the quartz capillary column in water, maintain a discharge rate of 1 bubble per second at the outlet end, observe the state of the effluent, and stop until the effluent becomes turbid, drain the solution in the quartz capillary column, and recrystallize it at 200 °C for 3 h under a nitrogen gas purge.

[0012] The preparation method described in the present invention, wherein step (2) specifically includes the following method: Use the static coating method, weigh 5 mg of TAPT material and dissolve it in 10 mL of dichloromethane solution to prepare a solution with a concentration of 0.5%, in units of w / v, and ultrasonically treat it for 5 min to prepare a stationary liquid; Use a manual syringe or a method of pressurizing through a gas chromatograph injection port to slowly pass the stationary liquid through the pretreated quartz capillary column until the stationary liquid fills the entire quartz capillary column, then seal one end of the quartz capillary column and connect the other end to a vacuum system, and slowly evaporate the solvent in a constant temperature water bath at 39 °C, and the stationary phase is evenly coated on the inner wall of the quartz capillary column.

[0013] The preparation method described in the present invention, wherein step (3) specifically includes the following method: Connect one end of the quartz capillary column coated with the stationary phase to the injection port of a gas chromatograph, and age it in a nitrogen atmosphere by means of programmed temperature rise to obtain a product, namely a TAPT chromatographic column.

[0014] The preparation method described in the present invention, wherein the method of programmed temperature rise in the aging process is specifically: The initial temperature is 40 °C, and it is raised to 200 °C at a rate of 2 °C / min and held for 2 h, and this is repeated three times to complete the aging process.

[0015] The difference between the novel capillary gas chromatographic column based on triazine derivatives as the stationary phase of the present invention and the prior art lies in:

[0016] The novel capillary gas chromatography column based on triazine derivatives as the stationary phase in the present invention uses triazine derivatives in the field of gas chromatography separation, prepares a capillary gas chromatography column, and has excellent separation effects on alkane homologues, trichlorobenzene + trimethylbenzene, and isomers of alcohols and phenols that are difficult to separate.

[0017] Taking 2,4,6-tris(4-aminophenyl)-1,3,5-triazine as an example, the chromatographic performance of triazine derivatives as the gas chromatography stationary phase was investigated. The presence of amino groups on the triazine derivatives expands the ability of triazine to easily form hydrogen bonds with the separated substances, thereby separating the separated substances. The presence of three nitrogen atoms in the middle of the triazine derivatives results in strong dipole interactions in the system, which also makes it easier to separate the separated substances. After statically coating the triazine derivatives on the inner wall of the capillary, a gas chromatography column was prepared, and the performance of the triazine derivative chromatographic column was investigated by separating various compounds, such as alkane homologues, BTXE reagents, trichlorobenzene + trimethylbenzene isomers, and isomers of alcohols and phenols that are difficult to separate.

[0018] The following further describes the novel capillary gas chromatography column based on triazine derivatives as the stationary phase of the present invention with reference to the accompanying drawings. Description of the Drawings

[0019] Figure 1 It is the effect diagram of separating alkane homologues by the capillary gas chromatography column with triazine derivatives as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-7 marked in the figure represent n-octane, n-nonane, n-decane, n-undecane, n-dodecane, n-tridecane, and n-tetradecane respectively;

[0020] Figure 2 It is the effect diagram of separating BTEX reagents by the capillary gas chromatography column with triazine derivatives as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-5 marked in the figure represent benzene, toluene, ethylbenzene, o-xylene, and m-xylene respectively;

[0021] Figure 3 It is the effect diagram of separating mixed alcohol homologues by the capillary gas chromatography column with triazine derivatives as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-7 marked in the figure represent n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol, n-decanol, and n-undecanol respectively;

[0022] Figure 4 It is the effect diagram of separating a mixture of ketones by the capillary gas chromatography column with triazine derivatives as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-5 marked in the figure represent 2-pentanone, 2-hexanone, cyclohexanone, 2,5-hexanedione, and acetophenone respectively;

[0023] Figure 5The effect diagram of separating propylbenzene isomers and butylbenzene isomers by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-5 marked in the figure represent isopropylbenzene, n-propylbenzene, tert-butylbenzene, isobutylbenzene, and n-butylbenzene respectively;

[0024] Figure 6 The effect diagram of separating trichlorobenzene and trimethylbenzene isomers by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-6 marked in the figure represent 1,3,5-trimethylbenzene; 1,2,4-trimethylbenzene; 1,2,3-trimethylbenzene, 1,3,5-trichlorobenzene, 1,2,4-trichlorobenzene, 1,2,3-trichlorobenzene respectively;

[0025] Figure 7 The effect diagram of separating nerol / geraniol and musk / carvacrol by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-4 marked in the figure represent nerol, geraniol, thymol, and carvacrol respectively;

[0026] Figure 8 The effect diagram of separating naphthol isomers by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-2 marked in the figure represent 1-naphthol and 2-naphthol respectively;

[0027] Figure 9 The effect diagram of separating decalin isomers by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-2 marked in the figure represent trans-decalin and cis-decalin respectively;

[0028] Figure 10 The effect diagram of separating pentanol isomers by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-3 marked in the figure represent sec-pentanol, neopentanol, and n-pentanol respectively;

[0029] Figure 11 The effect diagram of separating xylenol isomers by a capillary gas chromatography column with a triazine derivative as the stationary phase under certain chromatographic conditions. The chromatographic peaks 1-5 marked in the figure represent 2,6-xylenol, 2,5-xylenol, 2,3-xylenol, 3,5-xylenol, and 3,4-xylenol respectively;

[0030] Figure 12 The effect diagram of separating a hydrogen-bonding type 9 mixed sample by a capillary gas chromatography column with a triazine derivative as the stationary phase and a DB-35MS commercial column under certain chromatographic conditions. The chromatographic peaks 1-9 marked in the figure represent p-diethylbenzene, o-chlorophenol, o-nitrotoluene, naphthalene, methyl nonanoate, 2,3-xylenol, m-bromonitrobenzene, biphenyl, and methyl undecanoate. Detailed implementation methods

[0031] The molecular structural formula of the stationary phase (triazine derivative) involved in the present invention is as follows:

[0032]

[0033] In the present invention, the fused silica capillary column: length 5 m, inner diameter 0.25 mm, purchased from Yongnian Ruifeng Chromatographic Devices Co., Ltd., Hebei Province; DB-35MS: 4 m, Agilent Technologies, USA; gas chromatograph: Agilent 7890B, Agilent Technologies, USA.

[0034] For the novel capillary gas chromatographic column of the present invention based on a triazine derivative as the stationary phase, a stationary phase containing a triazine derivative is coated on the inner wall of the fused silica capillary column.

[0035] The preparation method of the novel capillary gas chromatographic column of the present invention based on a triazine derivative as the stationary phase includes the following steps:

[0036] (1) Pretreatment of the fused silica capillary column: Take a 5 m fused silica capillary column with an inner diameter of 0.25 mm, rinse it with dichloromethane for 20 min, and age it at 260 °C for 3 h under a nitrogen atmosphere: Weigh 1.31 g of NaCl and place it in 10 mL of anhydrous methanol, stir vigorously for 45 min, take 6 mL of the supernatant and add it to 8 mL of a vigorously stirred chloroform solution, add 0.6 mL of methanol and stir for 5 min, then add 8 mL of chloroform and stir for 2 min to obtain a saturated NaCl solution; Use a manual syringe or a method of pressurizing through the chromatographic injection port to make the saturated NaCl solution pass through the aged fused silica capillary column, immerse the outlet end of the fused silica capillary column in water, maintain a discharge rate of 1 bubble / second at the outlet end, observe the state of the effluent, stop until the effluent becomes turbid, drain the solution in the fused silica capillary column, and recrystallize it at 200 °C for 3 h under a nitrogen gas purge.

[0037] (2) Coating of the stationary phase: Coating is carried out by the static method. Weigh 5 mg of TAPT material and dissolve it in 10 mL of dichloromethane solution to prepare a solution with a concentration of 0.5% (w / v), and ultrasonically treat it for 5 min to prepare the stationary liquid; Use a manual syringe or a method of pressurizing through the gas chromatographic injection port to slowly pass the stationary liquid through the pretreated fused silica capillary column until the stationary liquid fills the entire fused silica capillary column, then seal one end of the fused silica capillary column and connect the other end to a vacuum system, and slowly volatilize the solvent in a 39 °C constant temperature water bath, so that the stationary phase is uniformly coated on the inner wall of the fused silica capillary column.

[0038] (3) Aging of the chromatographic column: One end of the quartz capillary column coated with the stationary phase was connected to the injection port of the gas chromatograph, and it was aged under a nitrogen atmosphere by means of programmed temperature rise to obtain the product, namely the TAPT chromatographic column. Among them, the way of programmed temperature rise in the aging process was specifically as follows: the initial temperature was 40 °C, and it was raised to 200 °C at a rate of 2 °C / min and held for 2 h. After repeating this three times, the aging process was completed.

[0039] In the present invention, a novel capillary gas chromatographic column with a triazine derivative as the stationary phase was prepared by statically coating the triazine derivative on the inner wall of an elastic fused silica capillary that had been roughened with a sodium chloride methanol suspension. The capillary column obtained in the present invention has high column efficiency, good inertness and good thermal stability, and can be used for the separation of components with different polarities such as alcohols, aromatics, phenols and their isomers. It is especially suitable for the effective separation of difficult-to-separate isomers such as phenols and alcohols, and has good application prospects.

[0040] The novel capillary gas chromatographic column based on the triazine derivative as the stationary phase in the present invention enables isomers with different polarities to be effectively separated on a single gas chromatographic stationary phase.

[0041] Figure 1 It is a capillary gas chromatographic column with a triazine derivative prepared by the static method as the stationary phase. When separating alkane homologues on an Agilent 7890B chromatograph, the obtained separation effect can meet the separation and detection of alkane homologues. The chromatographic parameters are as follows: high-purity N2 was used as the carrier gas, the carrier gas flow rate was 1.0 mL / min, the split ratio was 150:1, and the programmed temperature rise was: 40 °C, raised to 140 °C at 10 °C / min and held for 5 minutes.

[0042] Figure 2 It is a capillary gas chromatographic column with a triazine derivative prepared by the static method as the stationary phase. When separating the BTXE reagent on an Agilent 7890B chromatograph, the obtained separation effect can meet the separation and detection of the BTXE reagent. The chromatographic parameters are as follows: high-purity N2 was used as the carrier gas, the carrier gas flow rate was 1.0 mL / min, the split ratio was 150:1, and the programmed temperature rise was: 40 °C, raised to 140 °C at 10 °C / min and held for 5 minutes.

[0043] Figure 3 It is a capillary gas chromatographic column with a triazine derivative prepared by the static method as the stationary phase. When separating aliphatic alcohol homologues on an Agilent 7890B chromatograph, the obtained separation effect can meet the separation and detection of the mixed alcohols. The chromatographic parameters are as follows: high-purity N2 was used as the carrier gas, the carrier gas flow rate was 1.0 mL / min, the split ratio was 150:1, and the programmed temperature rise was: 40 °C, raised to 140 °C at 10 °C / min and held for 5 minutes.

[0044] Figure 4It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating a ketone mixture on an Agilent 7890B chromatograph, the separation effect can meet the separation and detection requirements of the ketone mixture. The chromatographic parameters are as follows: using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, rising to 140 °C at a rate of 10 °C / min, and holding for 5 minutes.

[0045] Figure 5 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating propylbenzene isomers and butylbenzene isomers on an Agilent 7890B chromatograph, the separation effect can meet the separation and detection requirements of propylbenzene isomers and butylbenzene isomers. The chromatographic parameters are as follows: using high-purity N2 as the carrier gas, the carrier gas flow rate is 0.35 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, holding for 1 minute, rising to 140 °C at a rate of 10 °C / min, and holding for 5 minutes.

[0046] Figure 6 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating trichlorobenzene + trimethylbenzene isomers on an Agilent 7890B chromatograph, the separation effect can meet the separation and detection requirements of trichlorobenzene + trimethylbenzene isomers. The chromatographic parameters are as follows: using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, rising to 140 °C at a rate of 20 °C / min, and holding for 5 minutes.

[0047] Figure 7 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating nerol / geraniol and musk / carvacrol on an Agilent 7890B chromatograph, the separation effect can meet the separation and detection requirements of nerol / geraniol and musk / carvacrol. The chromatographic parameters are as follows: using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, rising to 140 °C at a rate of 10 °C / min, and holding for 5 minutes.

[0048] Figure 8 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating naphthol isomers on an Agilent 7890B chromatograph, the separation effect can meet the separation and detection requirements of naphthol isomers. The chromatographic parameters are as follows: using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 100 °C, rising to 140 °C at a rate of 10 °C / min, and holding for 5 minutes.

[0049] Figure 9It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating decalin isomers on an Agilent 7890B chromatograph, the separation effect obtained can meet the separation and detection requirements of decalin isomers. The chromatographic parameters are as follows: Using high-purity N2 as the carrier gas, the carrier gas flow rate is 0.5 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, rising to 140 °C at a rate of 10 °C / min, and holding for 5 minutes.

[0050] Figure 10 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating pentanol isomers on an Agilent 7890B chromatograph, the separation effect obtained can meet the separation and detection requirements of pentanol isomers. The chromatographic parameters are as follows: Using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and maintaining a constant temperature of 40 °C.

[0051] Figure 11 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase. When separating xylenol isomers on an Agilent 7890B chromatograph, the separation effect obtained can meet the separation and detection requirements of xylenol isomers. The chromatographic parameters are as follows: Using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, rising to 140 °C at a rate of 5 °C / min, and holding for 5 minutes.

[0052] Figure 12 It is a capillary gas chromatography column with a triazine derivative prepared by the static method as the stationary phase and a DB-35MS commercial column. When separating the hydrogen-bonded mixture 9 on an Agilent 7890B chromatograph, the separation effect obtained by the TAPT chromatographic column can meet the separation and detection requirements of the hydrogen-bonded mixture 9, while the DB-35MS commercial column fails to completely separate. The chromatographic parameters are as follows: Using high-purity N2 as the carrier gas, the carrier gas flow rate is 1.0 mL / min, the split ratio is 150:1, and the temperature programming is as follows: 40 °C, holding for 2 minutes, rising to 100 °C at a rate of 10 °C / min, holding for 2 minutes, and then rising to 160 °C at a rate of 15 °C / min.

[0053] The present invention is not limited to the separation and use of capillary chromatographic columns with a TAPT material prepared by the static method as the stationary phase. Different chromatographic columns obtained by other methods of preparing chromatographic columns using the TAPT material for gas chromatography separation are within the protection scope of the present invention.

[0054] The above-described embodiments are only used to describe the preferred embodiments of the present invention, and do not limit the scope of the present invention. Without departing from the design spirit of the present invention, various deformations and improvements made by those of ordinary skill in the art to the technical solutions of the present invention shall fall within the protection scope determined by the claims of the present invention.

Claims

1. A novel capillary gas chromatography column based on triazine derivatives as stationary phase, characterized in that: A layer of stationary phase containing a triazine derivative is coated on the inner wall of a quartz capillary column, wherein the triazine derivative is 2,4,6-tris(4-aminophenyl)-1,3,5-triazine; The compounds were separated by a capillary gas chromatography column with 2,4,6-tris(4-aminophenyl)-1,3,5-triazine as the stationary phase. During the separation process, the quartz capillary column used was 5 m long and 0.25 mm in inner diameter. The gas chromatograph was Agilent 7890B. The chromatographic conditions included: high-purity N2 as carrier gas with a split ratio of 150:1; The compound is one of the following: Alkane homologues, BTEX reagents, mixed alcohol homologues, ketone mixtures or neroli / geraniol and musk / carvacrol, propylbenzene isomers and butylbenzene isomers, trichlorobenzene and trimethylol isomers, naphthol isomers, decalin isomers, amyl alcohol isomers, xylenol isomers, hydrogen bond type 9 kinds of mixed samples; in: The 9 hydrogen bond type mixed samples are p-diethylbenzene, o-chlorophenol, o-nitrotoluene, naphthalene, methyl nonanoate, 2,3-xylenol, m-bromonitrobenzene, biphenyl and methyl undecanoate; the alkane homologues are n-octane, n-nonane, n-decane, n-undecane, n-dodecane, n-tridecane and n-tetradecane; the BTEX reagents are benzene, toluene, ethylbenzene, o-xylene and m-xylene; the mixed alcohol homologues are n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol, n-decanol and n-undecanol; the ketone mixed sample is 2-pentanone, 2-hexanone, cyclohexanone, 2,5-hexanedione and acetophenone; the neroli / geraniol and musk / carvacrol are neroli, geraniol, muscol and carvacrol; The propylbenzene isomers and butylbenzene isomers are isopropylbenzene, normal-propylbenzene, tert-butylbenzene, isobutylbenzene and normal-butylbenzene; the trichlorobenzene and trimethylbenzene isomers are 1,3,5-trimethylbenzene, 1,2,4-trimethylbenzene, 1,2,3-trimethylbenzene, 1,3,5-trichlorobenzene, 1,2,4-trichlorobenzene and 1,2,3-trichlorobenzene; the naphthol isomers are 1-naphthol and 2-naphthol; the decalin isomers are trans-decalin and cis-decalin; the amyl alcohol isomers are sec-amyl alcohol, neopentyl alcohol and normal amyl alcohol; the xylenol isomers are 2,6-xylenol, 2,5-xylenol, 2,3-xylenol, 3,5-xylenol and 3,4-xylenol.

2. The novel capillary gas chromatography column based on triazine derivatives as stationary phase according to claim 1, characterized in that: When separating 9 kinds of hydrogen bond type mixed samples, the chromatographic conditions also include: carrier gas flow rate 1.0mL / min, program temperature rise 40℃, hold for 2 minutes, increase to 100℃ at 10℃ / min, hold for 2 minutes, and increase to 160℃ at 15℃ / min.

3. The novel capillary gas chromatography column based on triazine derivatives as stationary phase according to claim 1, characterized in that: When separating alkane homologues, BTEX reagent, mixed alcohol homologues, ketone mixtures or neroli / geraniol and musk / carvacrol, the chromatographic conditions also include: carrier gas flow rate of 1.0 mL / min, program temperature: 40°C, 10°C / min to 140°C, hold for 5 minutes; When separating propylbenzene isomers and butylbenzene isomers, the chromatographic conditions also include: a carrier gas flow rate of 0.35 mL / min, a temperature program of 40°C, held for 1 minute, increased to 140°C at 10°C / min, and held for 5 minutes; When separating trichlorobenzene and trimethylbenzene isomers, the chromatographic conditions also include: a carrier gas flow rate of 1.0 mL / min, a program temperature rise of 40° C., 20° C. / min to 140° C., and maintaining for 5 minutes.

4. The novel capillary gas chromatography column based on triazine derivatives as stationary phase according to claim 1, characterized in that: When separating naphthol isomers, the chromatographic conditions also include: a carrier gas flow rate of 1.0 mL / min, a temperature program of 100°C, 10°C / min to 140°C, and holding for 5 minutes; When separating decalin isomers, the chromatographic conditions also include: a carrier gas flow rate of 0.5 mL / min, a temperature program of 40°C, 10°C / min to 140°C, and holding for 5 minutes; When separating the amyl alcohol isomers, the chromatographic conditions also included: a carrier gas flow rate of 1.0 mL / min and a constant temperature of 40°C; When separating the xylenol isomers, the chromatographic conditions also include: a carrier gas flow rate of 1.0 mL / min, a temperature program of 40° C., 5° C. / min to 140° C., and maintaining for 5 minutes.

5. The method for preparing a novel capillary gas chromatography column based on a triazine derivative as a stationary phase according to claim 1, characterized in that: The steps include: (1) Pretreatment of quartz capillary columns; (2) Stationary phase coating: static coating method, weigh 5 mg of TAPT material and dissolve it in 10 mL of dichloromethane solution to prepare a solution with a concentration of 0.5%, the unit is w / v, and ultrasonic treatment is performed for 5 minutes to prepare a stationary phase; the stationary phase is slowly passed through the pretreated quartz capillary column by a manual syringe or by connecting to the gas chromatography injection port to apply pressure until the stationary phase fills the entire quartz capillary column, and then one end of the quartz capillary column is sealed and the other end is connected to a vacuum system. The solvent is slowly evaporated in a constant temperature water bath at 39°C, and the stationary phase is evenly coated on the inner wall of the quartz capillary column; (3) Aging of the chromatographic column.

6. The preparation method according to claim 5, characterized in that: Step (1) specifically comprises the following method: taking a 5 m quartz capillary column with an inner diameter of 0.25 mm, flushing it with dichloromethane for 20 min, and aging it at 260° C. for 3 h under a nitrogen atmosphere; weighing 1.31 g of NaCl and placing it in 10 mL of anhydrous methanol, vigorously stirring it for 45 min, taking 6 mL of the supernatant and adding it to 8 mL of chloroform solution that was vigorously stirred, adding 0.6 mL of methanol and stirring it for 5 min, and then adding 8 mL of chloroform and stirring it for 2 min to obtain a saturated NaCl solution; using a manual syringe or connecting the chromatographic injection port to pressurize the quartz capillary column that has been subjected to the aging treatment with the saturated NaCl solution, immersing the outlet end of the quartz capillary column in water, maintaining a discharge rate of 1 bubble / second at the outlet end, observing the state of the effluent until the effluent becomes turbid, discharging the solution in the quartz capillary column, and recrystallizing it at 200° C. for 3 h under a nitrogen flow purge.

7. The preparation method according to claim 5, characterized in that: Step (3) specifically includes the following method: connecting one end of the quartz capillary column coated with the stationary phase to the inlet of a gas chromatograph, and aging the column by programmed temperature rise in a nitrogen atmosphere to obtain a product, namely, a TAPT chromatographic column.

8. The preparation method according to claim 7, characterized in that: The programmed temperature rise method of the aging process is specifically as follows: the initial temperature is 40° C., and the temperature is raised to 200° C. at a rate of 2° C. / min, and maintained for 2 hours. This is repeated three times to complete the aging process.

Citation Information

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