CN115112786A - Method for detecting content of polycyclic aromatic hydrocarbon substances in incense products - Google Patents
Method for detecting content of polycyclic aromatic hydrocarbon substances in incense products Download PDFInfo
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- CN115112786A CN115112786A CN202210606689.7A CN202210606689A CN115112786A CN 115112786 A CN115112786 A CN 115112786A CN 202210606689 A CN202210606689 A CN 202210606689A CN 115112786 A CN115112786 A CN 115112786A
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- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 38
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 238000012360 testing method Methods 0.000 claims abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 12
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 3
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
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- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
- G01N2030/045—Standards internal
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/062—Preparation extracting sample from raw material
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention relates to the field of incense product testing, and provides a method for detecting the content of polycyclic aromatic hydrocarbon substances in incense products, which comprises the following steps: (1) collecting smoke generated after burning the incense; (2) adding dichloromethane into the smoke, performing ultrasonic treatment, adding a polycyclic aromatic hydrocarbon extracting agent, fully enriching polycyclic aromatic hydrocarbons, eluting by using an eluent, performing rotary reduced pressure evaporation on the eluent or blowing the eluent to be nearly dry by using soft nitrogen, adding ethyl acetate for redissolution, and adding an internal standard substance to serve as a sample to be detected; (3) preparing a series of standard working solutions containing target substances with different concentrations, measuring by gas chromatography-tandem mass spectrometry, and drawing a standard curve; (4) and (3) determining a sample to be detected through gas chromatography-tandem mass spectrometry, determining the peak area ratio of the secondary selected ions of the target substance and the corresponding internal standard substance, substituting the peak area ratio into a standard curve, and obtaining the content of various polycyclic aromatic hydrocarbons. The detection method provided by the invention fills the blank in the prior art, and is simple, convenient and quick to operate, accurate in detection result and good in repeatability.
Description
Technical Field
The invention relates to the technical field of incense product testing, in particular to a method for detecting the content of polycyclic aromatic hydrocarbon substances in incense products.
Background
Polycyclic Aromatic Hydrocarbons (PAHs) are volatile Hydrocarbons produced when organic substances such as coal, petroleum, wood, tobacco, organic high molecular compounds and the like are not completely combusted, have strong toxicity and carcinogenic effect, can cause various damages to human bodies, such as damages to a respiratory system, a circulatory system and a nervous system, damages to livers and kidneys, and are considered as main organic pollutants affecting human health.
The incense products are widely used in public places such as religion, etiquette, sacrifice, etc., and at present, a large amount of articles which can generate smoke gas, such as incense, etc., need to be burnt during every day worshiping and praying activities of the temple. The incense can release various air pollutants such as granular substances, formaldehyde, benzene series substances, Polycyclic Aromatic Hydrocarbons (PAHs) and the like, the concentration of toxic and harmful substances after the incense is burnt can be accurately detected, the quality of the incense products can be improved, the adverse effect of harmful substances of the incense products on health is reduced, and the harm of incense activities to the ecological environment is reduced. The existing incense standards mainly comprise GB 26386-2011 general technical conditions for safety of incense products and GB/T26393-2011 test methods for harmful substances of incense products, but the two standards do not relate to the detection requirement of the content of polycyclic aromatic hydrocarbon in smoke after the incense is burnt. At present, no standard exists in China for guiding the detection of the content of polycyclic aromatic hydrocarbon substances discharged after burning of incense products, and the content of polycyclic aromatic hydrocarbon cannot be detected quickly and accurately.
Patent application No. CN201811576886.9 discloses a method for determining the content of 16 polycyclic aromatic hydrocarbons in incense smoke by thermal desorption/gas chromatography-mass spectrometry. Burning the incense sample in a space of 1.8M multiplied by 1.8M, absorbing and enriching the smoke to a heat desorption pipe filled with Tenax-TA filler by a sampling pump, detecting by GC-MS in a selective ion (SI M) mode after heat desorption, and quantifying by an external standard method. The result shows that the concentration of 16 polycyclic aromatic hydrocarbons is in good linear relation within the range of 0.05-1.0 mg/L, and the correlation coefficients r are all largeAt 0.995, the detection limit of the method is 0.06-1.10 ng/m 3 The average recovery rate of the standard addition is 89.2-100.7%, and the relative standard deviation is 1.7-5.0%. The method can effectively perform qualitative and quantitative analysis on 16 polycyclic aromatic hydrocarbons in the fuel smoke, has the characteristics of simplicity, high speed, high reliability and the like, and can meet the experimental requirements.
Disclosure of Invention
Therefore, aiming at the content, the method for detecting the content of the polycyclic aromatic hydrocarbon substances in the incense products fills the blank of the prior art, and the adopted detection method is simple and convenient to operate, quick, accurate in detection result and good in repeatability.
In order to achieve the purpose, the invention is realized by the following technical scheme:
a method for detecting the content of polycyclic aromatic hydrocarbon substances in incense products comprises the following steps:
(1) the method comprises the following steps that a test bed is arranged in the middle of a sealed glass square box of 1.0m multiplied by 1.0m, a sampling device is arranged on one side of the test bed, burning incense is ignited on the test bed, sampling is carried out for 40min, the flow rate is 0.5L/min, 20L of smoke is collected in the sampling device in total, and fans are arranged on the top and two sides of the glass square box;
the sampling device comprises a shell, the top of the shell is provided with a plurality of sampling ports, the sampling ports are connected with one end of a sampling pipe through an air duct, the other end of the sampling pipe is connected with one end of a gas flow regulating assembly, and the other end of the gas flow regulating assembly is connected with a negative pressure pump through a negative pressure pipe;
(2) adding dichloromethane and 30-60min of ultrasound into a sampling tube, pouring into a collecting bottle, adding a polycyclic aromatic hydrocarbon extracting agent, oscillating 3-10min in a vortex mixing oscillator to enable the polycyclic aromatic hydrocarbon extracting agent to be fully contacted with polycyclic aromatic hydrocarbon, standing for 15-30min, fully enriching polycyclic aromatic hydrocarbon by the polycyclic aromatic hydrocarbon extracting agent, placing a permanent magnet on the outer wall of one side of the collecting bottle, attracting and fixing the polycyclic aromatic hydrocarbon extracting agent, pouring out the solution in the collecting bottle, removing the permanent magnet, adding an eluant into the collecting bottle, oscillating and mixing in the vortex mixing oscillator, eluting polycyclic aromatic hydrocarbon, realizing phase separation by the permanent magnet, and pouring out the eluant, namely the solution containing polycyclic aromatic hydrocarbon;
carrying out rotary reduced pressure evaporation on the eluent or blowing the eluent to be nearly dry by using soft nitrogen, adding 1 ml of ethyl acetate for redissolution, and adding an internal standard substance to be used as a sample to be detected;
the internal standard substance is one or more of deuterated compounds of 16 polycyclic aromatic hydrocarbons, and the 16 polycyclic aromatic hydrocarbons are naphthalene, acenaphthylene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene and benzo [ a ] a]Anthracene,
Benzo [ b ]]Fluoranthene, benzo [ k ]]Fluoranthene, benzo [ a ]]Pyrene, indeno [1,2,3-cd]Pyrene, dibenzo [ a, h ]]Anthracene and benzo [ g, h, i ]]Pyrene;
the polycyclic aromatic hydrocarbon extractant is prepared by carrying out condensation reaction on 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a solvent, and magnetic zeolite molecular sieve nano-particles are added in the preparation process of the polycyclic aromatic hydrocarbon extractant;
(3) preparing a series of standard working solutions containing target substances with different concentrations, wherein the concentrations are as follows in sequence: 1ng/mL, 2ng/mL, 5ng/mL, 10ng/mL, 20ng/mL, 50ng/mL, 100ng/mL, measured by gas chromatography-tandem mass spectrometry, and fitted to obtain a standard curve;
(4) and (3) determining the sample to be detected through gas chromatography-tandem mass spectrometry, measuring the peak area ratio of the secondary selective ions of the target substance and the corresponding internal standard substance, substituting the peak area ratio into the standard curve, and solving the content of various polycyclic aromatic hydrocarbons in the sample.
The further improvement is that: in the gas chromatography-tandem mass spectrometry, the adopted chromatographic conditions are as follows: using HP-5MS capillary chromatographic column with specification of 30m × 0.25mm × 0.25 μm; temperature programming: the initial temperature is 80 ℃, the temperature is increased to 180 ℃ at 10 ℃/min after the temperature is maintained at 1min, the temperature is increased to 280 ℃ at 5 ℃/min, and the temperature is maintained at 15 min; the carrier gas is nitrogen, and the purity is more than or equal to 99.999 percent; a constant flow mode with a flow rate of 1.5 mL/min; split-flow sample injection with a split-flow ratio of 10: 1; the sample injection amount is 1 mu L;
the mass spectrometry conditions used were: the ionization mode is an electron bombardment source, the temperature of the ion source is 280 ℃, and the ionization energy is 70 ev; the scanning mode is as follows: multiple reaction monitoring, MRM, mode; collision gas: nitrogen at a flow rate of 1.5 mL/min.
The further improvement is that: the preparation method of the polycyclic aromatic hydrocarbon comprises the following steps: dissolving 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a solvent, adding 4-6mol/L acetic acid solution as a catalyst, stirring and mixing uniformly, adding magnetic zeolite molecular sieve nanoparticles, heating to 100-110 ℃ in a nitrogen atmosphere, reacting for 75-85h, washing the obtained solid after reaction by using acetone and n-hexane in sequence, washing away unreacted monomers remained in a pore channel, and finally drying in vacuum for 4-8h at 120-140 ℃ to obtain the polycyclic aromatic hydrocarbon extractant.
The further improvement is that: the adding amount of the solvent is 15-25 times of the mass of the 2, 6-diaminoanthraquinone, and the mass ratio of the acetic acid solution to the solvent is 1: 12-16.
The further improvement is that: the mass ratio of the 2, 6-diaminoanthraquinone, the 2, 5-dihydroxy-1, 4-terephthalaldehyde and the magnetic zeolite molecular sieve nanoparticles is 20-30: 12-28: 25-50.
The further improvement is that: the solvent is any one or more than two of 1, 4-dioxane, mesitylene and N, N-dimethylacetamide.
The further improvement is that: the magnetic zeolite molecular sieve nano-particles are prepared by the following method:
adding polyethylene glycol and sodium polyacrylate into sodium hydroxide aqueous solution, and stirring to completely dissolve the polyethylene glycol and the sodium polyacrylate to obtain solution A;
adding ferrous sulfate heptahydrate, ferric trichloride hexahydrate and zeolite molecular sieve into deionized water, stirring and mixing for 15-25min, then slowly dropwise adding the solution A at the temperature of 70-80 ℃ in an inert gas atmosphere, and continuing to react for 40-60min after dropwise adding is finished to obtain Fe 3 O 4 A precursor of (a);
Fe 3 O 4 the precursor is reacted for 3.5 to 4.5 hours at the temperature of 135-155 ℃, and the reaction product is magnetically separated after being cooled to the room temperature to obtain a black solid;
and (3) washing the black solid with deionized water for 2-4 times, and drying to obtain the magnetic zeolite molecular sieve nano-particles.
The further improvement is that: the mass ratio of the ferrous sulfate heptahydrate, the ferric trichloride hexahydrate, the zeolite molecular sieve, the sodium hydroxide, the polyethylene glycol and the sodium polyacrylate is 1: 1.5-1.7: 0.4-0.6: 1.1-1.3: 0.6-0.8: 0.9-1.2.
By adopting the technical scheme, the invention has the beneficial effects that:
the polycyclic aromatic hydrocarbon extractant is formed by condensation reaction of primary amino in a 2, 6-diaminoanthraquinone molecular structure and aldehyde in a 2, 5-dihydroxy-1, 4-terephthalaldehyde molecular structure, belongs to a covalent organic framework material, has the characteristics of large specific surface area, high porosity and special nano-pore channel structure, can fully adsorb and load polycyclic aromatic hydrocarbon by utilizing the characteristics, and improves the recovery amount of the polycyclic aromatic hydrocarbon. The benzene ring structure on the covalent organic framework and the benzene ring of the polycyclic aromatic hydrocarbon have strong pi-pi action, so that the polycyclic aromatic hydrocarbon can be firmly adsorbed on the polycyclic aromatic hydrocarbon extracting agent, and the polycyclic aromatic hydrocarbon can be fully enriched. The polycyclic aromatic hydrocarbon extractant contains magnetic zeolite molecular sieve nanoparticles, and can be separated from the solution through an external magnetic field after the polycyclic aromatic hydrocarbon is selectively enriched, so that the treatment time and the treatment cost are greatly reduced.
The reaction principle for preparing the magnetic zeolite molecular sieve nanoparticles is as follows: fe 2+ +2Fe 3+ +8OH - ＝Fe 3 O 4 ↓+4H 2 And O. Mixing soluble ferric salt and soluble ferrous salt solution, then adding alkaline solution, controlling reaction temperature and time, and finally obtaining nano-scale magnetic Fe 3 O 4 And (3) granules. Fe obtained according to the above method 3 O 4 Although the shape of the particle is approximate to a sphere, the proportion of the particle with the defect is large, which influences the adsorption performance and the magnetic performance of the magnetic nano particle to a certain extent. The applicant has surprisingly found that the above problems can be solved by adding two high molecular polymers, polyethylene glycol and sodium polyacrylate, to obtain spherical particles with regular shape and only a few defects. The zeolite molecular sieve is a hydrate of a crystalline aluminosilicate metal salt in Fe 3 O 4 Precursor of (2) is highDuring the warm reaction, water molecules of the zeolite molecular sieve are removed, the remaining atoms form a cage structure, the polycyclic aromatic hydrocarbon extractant can be fully contacted with polycyclic aromatic hydrocarbon by utilizing the cage structure of the zeolite molecular sieve to form a pi-pi conjugated system, and the adsorption quantity of the polycyclic aromatic hydrocarbon is further improved.
The sampling device is used for collecting the smoke containing the polycyclic aromatic hydrocarbon, the sampling device is simple and convenient to operate, multiple smoke samples can be collected at the same time, the average values are obtained after the smoke samples are respectively tested, and the result is more accurate. The fan is arranged in the glass square box, so that the incense burning smoke in the box can be rapidly and uniformly mixed, and the content of polycyclic aromatic hydrocarbon in the collected smoke is closer to the actual situation. The content of different polycyclic aromatic hydrocarbons in the polycyclic aromatic hydrocarbon compounds released after burning of the incense is different, in order to enable the content of polycyclic aromatic hydrocarbons in the incense smoke to reach a measurable level and detect the actual content of 16 polycyclic aromatic hydrocarbons in the incense smoke, 10 incentives are burned at one time.
Compared with a GC-MS method and an HPLC method, the method has the advantages of accurate operation, high sensitivity and good repeatability, and is particularly suitable for detecting and analyzing polycyclic aromatic hydrocarbon substances in incense products. Before sample introduction, a polycyclic aromatic hydrocarbon extracting agent is adopted to pretreat a sample, so that the method is simple, convenient and quick, has a good polycyclic aromatic hydrocarbon enriching effect, and greatly reduces the processing time and cost.
Drawings
FIG. 1 is a schematic view of the structure of the glass square box of the present invention.
Detailed Description
The following detailed description will be provided for the embodiments of the present invention with reference to specific embodiments, so that how to apply the technical means to solve the technical problems and achieve the technical effects can be fully understood and implemented.
Unless otherwise indicated, the techniques employed in the examples are conventional and well known to those skilled in the art, and the reagents and products employed are also commercially available. The source, trade name and if necessary the constituents of the reagents used are indicated at the first appearance.
Example 1
The preparation method of the polycyclic aromatic hydrocarbon extractant comprises the following steps:
s1 preparation of magnetic zeolite molecular sieve nanoparticles
Adding polyethylene glycol 600 and sodium polyacrylate into sodium hydroxide aqueous solution, and stirring to completely dissolve the polyethylene glycol 600 and the sodium polyacrylate to obtain solution A;
adding ferrous sulfate heptahydrate, ferric trichloride hexahydrate and a zeolite molecular sieve into deionized water, stirring and mixing for 15min, then slowly dropwise adding the solution A at the temperature of 70 ℃ in an inert gas atmosphere, and continuously reacting for 60min after dropwise adding is finished to obtain Fe 3 O 4 The precursor of (2) is prepared from ferrous sulfate heptahydrate, ferric trichloride hexahydrate, a zeolite molecular sieve, sodium hydroxide, polyethylene glycol 600 and sodium polyacrylate in a mass ratio of 10: 15: 4: 11: 6: 9;
Fe 3 O 4 the precursor is reacted for 4.5 hours at 135 ℃, and after the reaction product is cooled to room temperature, the reaction product is magnetically separated to obtain black solid;
washing the black solid with deionized water for 2 times, and drying to obtain magnetic zeolite molecular sieve nanoparticles;
s2 condensation reaction
Dissolving 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a 1, 4-dioxane/mesitylene mixed solvent (volume ratio is 1:2), adding 4 mol/L of acetic acid solution as a catalyst, stirring and mixing uniformly, adding magnetic zeolite molecular sieve nanoparticles, heating to 100 ℃ in a nitrogen atmosphere, reacting for 85 hours, washing the solid obtained by separation after reaction with acetone and n-hexane in sequence, washing away unreacted monomers remaining in pore channels, and finally drying in vacuum at 120 ℃ for 8 hours to obtain the polycyclic aromatic hydrocarbon extractant. The mass ratio of the 2, 6-diaminoanthraquinone, the 2, 5-dihydroxy-1, 4-terephthalaldehyde and the magnetic zeolite molecular sieve nanoparticles is 20: 12: 25, the adding amount of the solvent is 25 times of the mass of the 2, 6-diaminoanthraquinone, and the mass ratio of the acetic acid solution to the solvent is 1: 12.
example 2
The preparation method of the polycyclic aromatic hydrocarbon extractant comprises the following steps:
s1 preparation of magnetic zeolite molecular sieve nanoparticles
Adding polyethylene glycol 600 and sodium polyacrylate into sodium hydroxide aqueous solution, and stirring to completely dissolve the polyethylene glycol 600 and the sodium polyacrylate to obtain solution A;
adding ferrous sulfate heptahydrate, ferric trichloride hexahydrate and a zeolite molecular sieve into deionized water, stirring and mixing for 20 min, then slowly dropwise adding the solution A at the temperature of 75 ℃ in an inert gas atmosphere, and continuously reacting for 50 min after dropwise adding is finished to obtain Fe 3 O 4 The precursor of (2) is prepared from ferrous sulfate heptahydrate, ferric trichloride hexahydrate, a zeolite molecular sieve, sodium hydroxide, polyethylene glycol 600 and sodium polyacrylate in a mass ratio of 10: 16: 5: 12: 7: 10;
Fe 3 O 4 the precursor is reacted for 4 hours at the temperature of 145 ℃, and the reaction product is magnetically separated after being cooled to the room temperature, so that a black solid is obtained;
washing the black solid with deionized water for 3 times, and drying to obtain magnetic zeolite molecular sieve nanoparticles;
s2 condensation reaction
Dissolving 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a 1, 4-dioxane/mesitylene mixed solvent (volume ratio is 1:2), adding 5 mol/L of acetic acid solution as a catalyst, stirring and mixing uniformly, adding magnetic zeolite molecular sieve nanoparticles, heating to 105 ℃ under the atmosphere of nitrogen, reacting for 80 hours, washing the solid obtained by separation after reaction with acetone and n-hexane in sequence, washing away unreacted monomers remained in pore channels, and finally drying for 6 hours in vacuum at 130 ℃ to obtain the polycyclic aromatic hydrocarbon extractant. The mass ratio of the 2, 6-diaminoanthraquinone, the 2, 5-dihydroxy-1, 4-terephthalaldehyde and the magnetic zeolite molecular sieve nanoparticles is 25: 20: 36, the adding amount of the solvent is 20 times of the mass of the 2, 6-diaminoanthraquinone, and the mass ratio of the acetic acid solution to the solvent is 1: 14.
example 3
The preparation method of the polycyclic aromatic hydrocarbon extractant comprises the following steps:
s1 preparation of magnetic zeolite molecular sieve nanoparticles
Adding polyethylene glycol 600 and sodium polyacrylate into sodium hydroxide aqueous solution, and stirring to completely dissolve the mixture to obtain solution A;
adding ferrous sulfate heptahydrate, ferric trichloride hexahydrate and a zeolite molecular sieve into deionized water, stirring and mixing for 25min, then slowly dropwise adding the solution A at the temperature of 80 ℃ in an inert gas atmosphere, and continuously reacting for 40min after dropwise adding is finished to obtain Fe 3 O 4 The precursor of (2) is prepared from ferrous sulfate heptahydrate, ferric trichloride hexahydrate, a zeolite molecular sieve, sodium hydroxide, polyethylene glycol 600 and sodium polyacrylate in a mass ratio of 10: 17: 6: 13: 8: 12;
Fe 3 O 4 the precursor is reacted for 3.5 hours at the temperature of 155 ℃, and after the reaction product is cooled to room temperature, the reaction product is magnetically separated to obtain black solid;
washing the black solid with deionized water for 4 times, and drying to obtain magnetic zeolite molecular sieve nanoparticles;
s2 condensation reaction
Dissolving 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a 1, 4-dioxane/mesitylene mixed solvent (volume ratio is 1:2), adding 6mol/L of acetic acid solution as a catalyst, stirring and mixing uniformly, adding magnetic zeolite molecular sieve nanoparticles, heating to 110 ℃ under the atmosphere of nitrogen, reacting for 75 hours, washing the solid obtained by separation after reaction with acetone and n-hexane in sequence, washing away unreacted monomers remained in pore channels, and finally drying for 4 hours in vacuum at 140 ℃ to obtain the polycyclic aromatic hydrocarbon extractant. The mass ratio of the 2, 6-diaminoanthraquinone, the 2, 5-dihydroxy-1, 4-terephthalaldehyde and the magnetic zeolite molecular sieve nanoparticles is 30: 28: 50, the adding amount of the solvent is 15 times of the mass of the 2, 6-diaminoanthraquinone, and the mass ratio of the acetic acid solution to the solvent is 1: 16.
example 4
A method for detecting the content of polycyclic aromatic hydrocarbon substances in incense products is characterized in that: the method comprises the following steps:
(1) sampling is carried out on a sealed glass square box with the thickness of 1.0m multiplied by 1.0m, the structural schematic diagram of the glass square box refers to fig. 1, a test bed 1 is arranged in the middle of the glass square box, a sampling device is arranged on one side of the test bed 1, burning incense is ignited on the test bed, sampling is carried out on 40min, the flow rate is 0.5L/min, and 20L smoke is collected in the sampling device in total;
the top and two sides of the glass square box are provided with fans 2, the sampling device comprises a shell 3, the top of the shell 3 is provided with a plurality of sampling ports 4, the sampling ports 4 are connected with one end of a sampling pipe 6 through air ducts 5, the other end of the sampling pipe 6 is connected with one end of a gas flow regulating assembly 7, and the other end of the gas flow regulating assembly 7 is connected with a negative pressure pump 9 through a negative pressure pipe 8;
(2) adding dichloromethane and 30min of ultrasound into a sampling tube, pouring into a collecting bottle, simultaneously adding the polycyclic aromatic hydrocarbon extracting agent prepared in the embodiment 1, oscillating 3 min in a vortex mixing oscillator to ensure that the polycyclic aromatic hydrocarbon extracting agent is fully contacted with polycyclic aromatic hydrocarbon, standing for 15min, fully enriching the polycyclic aromatic hydrocarbon by the polycyclic aromatic hydrocarbon extracting agent, placing a permanent magnet on the outer wall of one side of the collecting bottle, attracting and fixing the polycyclic aromatic hydrocarbon extracting agent, pouring out the solution in the collecting bottle, removing the permanent magnet, adding an eluant into the collecting bottle, oscillating and mixing in the vortex mixing oscillator, eluting the polycyclic aromatic hydrocarbon, realizing phase separation by the permanent magnet, and pouring out the eluant, namely the solution containing the polycyclic aromatic hydrocarbon;
carrying out rotary reduced pressure evaporation on the eluent or blowing the eluent to be nearly dry by using soft nitrogen, adding 1 ml of ethyl acetate for redissolution, and adding an internal standard substance to be used as a sample to be detected;
the internal standard substance is one or more of deuterated compounds of 16 polycyclic aromatic hydrocarbons, and the 16 polycyclic aromatic hydrocarbons are naphthalene, acenaphthylene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene and benzo [ a ] a]Anthracene,
Benzo [ b ]]Fluoranthene, benzo [ k ]]Fluoranthene, benzo [ a ]]Pyrene, indeno [1,2,3-cd]Pyrene, dibenzo [ a, h ]]Anthracene and benzo [ g, h, i ]]Pyrene;
the polycyclic aromatic hydrocarbon extractant is prepared by carrying out condensation reaction on 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a solvent, and magnetic zeolite molecular sieve nano-particles are added in the preparation process of the polycyclic aromatic hydrocarbon extractant;
(3) preparing a series of standard working solutions containing target substances with different concentrations, wherein the concentrations are as follows in sequence: 1ng/mL, 2ng/mL, 5ng/mL, 10ng/mL, 20ng/mL, 50ng/mL, 100ng/mL, measured by gas chromatography-tandem mass spectrometry, and fitted to obtain a standard curve;
(4) and (3) determining the sample to be detected through gas chromatography-tandem mass spectrometry, measuring the peak area ratio of the secondary selective ions of the target substance and the corresponding internal standard substance, substituting the peak area ratio into the standard curve, and solving the content of various polycyclic aromatic hydrocarbons in the sample.
In the gas chromatography-tandem mass spectrometry, the adopted chromatographic conditions are as follows: using HP-5MS capillary chromatography column with specification of 30m × 0.25mm × 0.25 μm; temperature programming: the initial temperature is 80 ℃, the temperature is increased to 180 ℃ at 10 ℃/min after the temperature is maintained at 1min, the temperature is increased to 280 ℃ at 5 ℃/min, and the temperature is maintained at 15 min; the carrier gas is nitrogen, and the purity is more than or equal to 99.999 percent; a constant flow mode with a flow rate of 1.5 mL/min; split-flow sample injection with a split-flow ratio of 10: 1; the sample injection amount is 1 mu L;
the mass spectrometry conditions used were: the ionization mode is an electron bombardment source, the temperature of the ion source is 280 ℃, and the ionization energy is 70 ev; the scanning mode is as follows: multiple reaction monitoring, MRM, mode; collision gas: nitrogen at a flow rate of 1.5 mL/min.
The linear equation, the regression coefficient, the recovery rate and the repeatability (n is 6) of the polycyclic aromatic hydrocarbon substances in the burning-type products of the burning-type smog and burning-type incense can be obtained through testing and analyzing calculation, and the test results are shown in the following table.
As can be seen from the table above, the recovery rate of polycyclic aromatic hydrocarbon substances in the incense smoke is 90.7-105.6%, and the relative standard deviation RSD is 3.6-8.2%, which proves that the method has high recovery rate and good repeatability.
The polycyclic aromatic hydrocarbon extractant prepared in example 2-3 was tested while the polycyclic aromatic hydrocarbon extractant prepared in example 1 was used to detect the content of polycyclic aromatic hydrocarbons in flammable products, and similar results to those described above were obtained, but not shown here.
It should be understood that the above description is only an example of the technical disclosure, and any modifications and variations made by those skilled in the art can be covered by the present disclosure, and not limited by the embodiments disclosed in the present disclosure.
Claims (8)
1. A method for detecting the content of polycyclic aromatic hydrocarbon substances in incense products is characterized in that: the method comprises the following steps:
(1) the method comprises the following steps that a test bed is arranged in the middle of a 1.0m multiplied by 1.0m sealed glass square box, a sampling device is arranged on one side of the test bed, burning incense is ignited on the test bed, sampling is carried out for 40min, the flow rate is 0.5L/min, 20L of smoke is collected in the sampling device in total, and fans are arranged on the top and two sides of the glass square box;
the sampling device comprises a shell, the top of the shell is provided with a plurality of sampling ports, the sampling ports are connected with one end of a sampling pipe through an air duct, the other end of the sampling pipe is connected with one end of a gas flow regulating assembly, and the other end of the gas flow regulating assembly is connected with a negative pressure pump through a negative pressure pipe;
(2) adding dichloromethane into a sampling tube, performing ultrasonic treatment for 30-60min, pouring into a collecting bottle, adding a polycyclic aromatic hydrocarbon extracting agent, oscillating for 3-10min in a vortex mixing oscillator to ensure that the polycyclic aromatic hydrocarbon extracting agent and polycyclic aromatic hydrocarbon are fully contacted, standing for 15-30min to ensure that the polycyclic aromatic hydrocarbon extracting agent is fully enriched with polycyclic aromatic hydrocarbon, placing a permanent magnet on the outer wall of one side of the collecting bottle, attracting and fixing the polycyclic aromatic hydrocarbon extracting agent, pouring out the solution in the collecting bottle, removing the permanent magnet, adding an eluent into the collecting bottle, oscillating and mixing in the vortex mixing oscillator to elute the polycyclic aromatic hydrocarbon, then realizing phase separation by using the permanent magnet, and pouring out the eluent, namely the solution containing the polycyclic aromatic hydrocarbon;
evaporating the eluent under reduced pressure by rotation or blowing the eluent to be nearly dry by using soft nitrogen, adding 1 ml of ethyl acetate for redissolution, and adding an internal standard substance to serve as a sample to be detected;
the internal standard substance is selected from deuterated compounds of 16 polycyclic aromatic hydrocarbonsOne or more, the 16 polycyclic aromatic hydrocarbon substances are naphthalene, acenaphthylene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene and benzo [ a ] a]Anthracene,
Benzo [ b ]]Fluoranthene, benzo [ k ]]Fluoranthene, benzo [ a ]]Pyrene, indeno [1,2,3-cd]Pyrene, dibenzo [ a, h ]]Anthracene and benzo [ g, h, i ]]Pyrene;
the polycyclic aromatic hydrocarbon extractant is prepared by carrying out condensation reaction on 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a solvent, and magnetic zeolite molecular sieve nano-particles are added in the preparation process of the polycyclic aromatic hydrocarbon extractant;
(3) preparing a series of standard working solutions containing target substances with different concentrations, wherein the concentrations are as follows in sequence: 1ng/mL, 2ng/mL, 5ng/mL, 10ng/mL, 20ng/mL, 50ng/mL, 100ng/mL, measured by gas chromatography-tandem mass spectrometry, and fitted to obtain a standard curve;
(4) and (3) determining the sample to be detected through gas chromatography-tandem mass spectrometry, measuring the peak area ratio of the secondary selective ions of the target substance and the corresponding internal standard substance, substituting the peak area ratio into the standard curve, and solving the content of various polycyclic aromatic hydrocarbons in the sample.
2. The method for detecting the content of polycyclic aromatic hydrocarbons in the incense products as claimed in claim 1, wherein the method comprises the following steps: in the gas chromatography-tandem mass spectrometry, the adopted chromatographic conditions are as follows: using HP-5MS capillary chromatography column with specification of 30m × 0.25mm × 0.25 μm; temperature programming: the initial temperature is 80 ℃, the temperature is increased to 180 ℃ at 10 ℃/min after the initial temperature is maintained for 1min, the temperature is increased to 280 ℃ at 5 ℃/min, and the initial temperature is maintained for 15 min; the carrier gas is nitrogen, and the purity is more than or equal to 99.999 percent; a constant flow mode, wherein the flow rate is 1.5 mL/min; split-flow sample injection with a split-flow ratio of 10: 1; the sample injection amount is 1 mu L;
the mass spectrometry conditions used were: the ionization mode is an electron bombardment source, the temperature of the ion source is 280 ℃, and the ionization energy is 70 ev; the scanning mode is as follows: multiple reaction monitoring, MRM, mode; collision gas: nitrogen at a flow rate of 1.5 mL/min.
3. The method for detecting the content of polycyclic aromatic hydrocarbons in the incense products as claimed in claim 1, wherein the method comprises the following steps: the preparation method of the polycyclic aromatic hydrocarbon comprises the following steps: dissolving 2, 6-diaminoanthraquinone and 2, 5-dihydroxy-1, 4-terephthalaldehyde in a solvent, adding 4-6mol/L acetic acid solution as a catalyst, stirring and mixing uniformly, adding magnetic zeolite molecular sieve nanoparticles, heating to 100 ℃ and 110 ℃ in a nitrogen atmosphere to react for 75-85h, washing the solid obtained by separation after the reaction by using acetone and n-hexane in sequence, washing the unreacted monomer remained in a pore channel, and finally drying in vacuum for 4-8h at 120 ℃ and 140 ℃ to obtain the polycyclic aromatic hydrocarbon extractant.
4. The method for detecting the content of polycyclic aromatic hydrocarbons in the incense products as claimed in claim 3, wherein the method comprises the following steps: the solvent is any one or more than two of 1, 4-dioxane, mesitylene and N, N-dimethylacetamide.
5. The method for detecting the content of polycyclic aromatic hydrocarbon substances in the incense products as claimed in claim 3, wherein the method comprises the following steps: the mass ratio of the 2, 6-diaminoanthraquinone, the 2, 5-dihydroxy-1, 4-terephthalaldehyde and the magnetic zeolite molecular sieve nanoparticles is 20-30: 12-28: 25-50.
6. The method for detecting the content of polycyclic aromatic hydrocarbons in the incense products as claimed in claim 3, wherein the method comprises the following steps: the adding amount of the solvent is 15-25 times of the mass of the 2, 6-diaminoanthraquinone, and the mass ratio of the acetic acid solution to the solvent is 1: 12-16.
7. The method for detecting the content of polycyclic aromatic hydrocarbons in the incense products as claimed in claim 1, wherein the method comprises the following steps: the magnetic zeolite molecular sieve nano-particles are prepared by the following method:
adding polyethylene glycol and sodium polyacrylate into sodium hydroxide aqueous solution, and stirring to completely dissolve the polyethylene glycol and the sodium polyacrylate to obtain solution A;
ferrous sulfate heptahydrate, ferric trichloride hexahydrate and zeolite molecular sieveAdding into deionized water, stirring and mixing for 15-25min, slowly dripping solution A at 70-80 deg.C under inert gas atmosphere, and reacting for 40-60min to obtain Fe 3 O 4 A precursor of (a);
Fe 3 O 4 the precursor is reacted for 3.5 to 4.5 hours at the temperature of 135-155 ℃, and the reaction product is magnetically separated after being cooled to the room temperature, so as to obtain black solid;
and (3) washing the black solid with deionized water for 2-4 times, and drying to obtain the magnetic zeolite molecular sieve nano-particles.
8. The method for detecting the content of polycyclic aromatic hydrocarbon substances in the incense products as claimed in claim 7, wherein the method comprises the following steps: the mass ratio of the ferrous sulfate heptahydrate, the ferric trichloride hexahydrate, the zeolite molecular sieve, the sodium hydroxide, the polyethylene glycol and the sodium polyacrylate is 1: 1.5-1.7: 0.4-0.6: 1.1-1.3: 0.6-0.8: 0.9-1.2.
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