CN115236229A - Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water - Google Patents
Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water Download PDFInfo
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Abstract
The invention relates to a gas chromatography-mass spectrometry analysis method of haloacetic acid in drinking water, belonging to the technical field of analytical chemistry. Compared with the prior art, the invention establishes a quantitative method of the haloacetic acid in the drinking water by using GC-MS, overcomes the defects of a standard method (USEPA, 552.3) provided by the United states environmental protection agency, a matching method (GB/T5749-2006) of China 'drinking water quality standard' and a diazomethane derivatization method, realizes one-step liquid-liquid extraction, can be used for loading on a machine for quantification after simple derivatization, and obtains high sensitivity, high labeling recovery rate, low method detection limit and low quantification limit. The method can be used for efficiently, quickly and accurately measuring the haloacetic acid in the drinking water.
Description
Technical Field
The invention relates to the technical field of analytical chemistry, in particular to a gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water.
Background
Haloacetic acid is the most common disinfection by-product in drinking water, and its concentration in drinking water is usually at pollution level of tens-hundreds μ g/L, and is second only to carbon-containing disinfection by-products (C-DBPs) of trihalomethane. However, haloacetic acid is more toxic than trihalomethane and less volatile, so its threat to drinking water safety and human health is of greater concern. In the sanitary Standard for Drinking Water (GB/T5749-2006) issued in 2006 in China, dichloroacetic acid and trichloroacetic acid are limited, and the maximum limit values are 50 mug/L and 100 mug/L respectively. A sensitive, simple and efficient haloacetic acid analysis method is established, and is the basis for recognizing the pollution condition of the substances in drinking water and the potential human health risks.
At present, a plurality of methods for measuring the haloacetic acid exist, and the most mainstream method is a standard method (USEPA, 552.3) provided by the U.S. national environmental protection agency and a matching method (GB/T5749-2006) of China 'drinking water quality standard', wherein the standard method and the matching method both adopt acidified methanol to perform derivatization on the haloacetic acid, and then a gas chromatography-electron capture detector (GC-ECD) is used for detecting the haloacetic acid. This method has problems of complicated process, low enrichment factor, high detection limit, and low recovery rate of monochloroacetic acid, and thus further improvement is required. Diazomethane derivatization is also a common method for detecting haloacetic acid, and effectively solves the problems of low enrichment factor of haloacetic acid, high detection limit and low recovery rate of monochloroacetic acid in USEPA552.3 and GB/T5749-2006, but the preparation of diazomethane needs a complex flow, and the generated diazomethane is easy to explode and is difficult to store, so the method is not an ideal alternative method.
At present, many researchers at home and abroad improve the standard method. For example, dithiopine et al disclose "a gas chromatography method for measuring nine trace amounts of haloacetic acid in barreled drinking water (application publication No.: CN 109212050A)". According to the method, hydroxymethylsulfonate-magnesium-aluminum type hydrotalcite is used for enriching haloacetic acid in a dispersed solid phase extraction mode, an acid is used for dissolving an adsorbent to elute the haloacetic acid, an organic solvent is used for extracting the haloacetic acid in an aqueous solution into the organic solvent, methanol and trimethylsilylated diazomethane n-hexane are used for derivatizing the haloacetic acid, and finally GC-ECD is used for detection. The method adopts hydroxymethyl sulfonate-magnesium aluminum type hydrotalcite for extraction, and the material is not easy to obtain and the price is not low, so that the method is not economical. Secondly, the method involves multiple extractions and elutions and more complex derivatizations, which is a cumbersome process. In addition, the sample is determined by using GC-ECD, because the sample has no mass spectrum, the sample is easy to be interfered by matrix to generate false positive, and the detection limit and the quantification limit of the method are too high and not sensitive enough for most haloacetic acids, particularly monochloroacetic acid, and the quantification limit is as high as 3.1 mu g/L and is far higher than the actual concentration of the monochloroacetic acid in drinking water.
The Chujin et al have disclosed "a method for rapidly detecting haloacetic acid as a disinfection by-product in drinking water (application publication No. CN 102520083A)". The method does not need pretreatment, directly uses liquid chromatography mass spectrometry to detect the haloacetic acid in the drinking water, and obtains a very low quantitative limit (0.05-0.86 mu g/L). However, from the figures and the attempts of the patent, it can be seen that the method disclosed by the authors has significant drawbacks. First, mass spectrometry is very difficult to respond because of the lack of enrichment, such low concentrations. Moreover, the method has the same quantitative limit as that reported in the literature and is also suitable for liquid chromatography mass spectrometry analysis, but the samples are basically consistent after being enriched by hundreds of times. Furthermore, we can see from the authors' figures that most haloacetic acids are essentially unresponsive and that the abundance of the noise peak is essentially consistent with the target compound.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a gas chromatography-mass spectrometry analysis method of haloacetic acid in drinking water, compared with the existing analysis method, the method is simple and high in sensitivity, and can be used for accurately measuring the haloacetic acid in the drinking water.
The purpose of the invention is realized by the following technical scheme:
the invention provides a gas chromatography-mass spectrometry analysis method of haloacetic acid in drinking water, which comprises the following steps:
(1) Taking a water sample of the drinking water, adding a residual chlorine quenching agent for quenching, and extracting haloacetic acid in the drinking water by adopting an organic solvent to prepare a sample solution;
(2) Preparing a mixed standard solution by using haloacetic acid as a standard substance and using an organic solvent as a solvent through stepwise dilution;
(3) Detecting and analyzing the mixed standard solution and the sample solution by using a gas chromatography-mass spectrometer;
(4) And (4) drawing a standard curve according to the detection and analysis result in the step (3) and analyzing the sample.
In one embodiment of the invention, in the step (1), the haloacetic acid in the drinking water is a disinfection by-product obtained by a disinfection process of the drinking water.
In one embodiment of the present invention, in the step (1), the organic solvent is one or more selected from the group consisting of methyl tert-butyl ether, n-hexane and ethyl acetate.
In one embodiment of the present invention, the specific steps of step (1) are: taking a water sample of the drinking water, measuring residual chlorine in the water, adding a residual chlorine quenching agent for quenching, adjusting the pH value to acidity, and adding an injection internal standard and a derivatization reagent to obtain a sample solution.
In one embodiment of the invention, the pH is <1.
In one embodiment of the invention, the derivatizing agent is selected from silylating agents.
In one embodiment of the invention, the silylating agent is selected from one or more of bis (trimethylsilyl) trifluoroacetamide, N- (t-butyldimethylsilyl) -N-methyltrifluoroacetamide, trimethylchlorosilane, hexamethyldisilazane and N, N dimethylformamide.
In one embodiment of the invention, the residual chlorine quencher is ascorbic acid and/or ammonium chloride.
In one embodiment of the present invention, the derivatization conditions of the derivatization reagent are: the heating temperature is 25-80 ℃, and the reaction time is 10-30 min.
In one embodiment of the present invention, in step (2), the haloacetic acid is selected from one or more of monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, monobromoacetic acid, dibromoacetic acid, monochloromonobromoacetic acid and monoiodoacetic acid.
In one embodiment of the present invention, in the step (3), the gas chromatography conditions in the gc-ms are as follows: the chromatographic column is HP-5ms chromatographic column, the carrier gas is helium, and the flow rate of the carrier gas is 1mL/min-2mL/min; the temperature of a sample inlet is 200-280 ℃; adopting non-shunting sample injection, wherein the sample injection amount is 1-2 muL; temperature rising procedure: the initial temperature is 35 ℃ and is kept for 2min, then the temperature is increased to 100 ℃ at the speed of 4 ℃/min and is kept for 2min, then the temperature is increased to 130 ℃ at the speed of 9 ℃/min and is kept for 1min, finally the temperature is increased to 280 ℃ at the speed of 12 ℃/min, and the operation time is 3min.
The principle of the preparation method is as follows:
the method is used for enriching 7 common haloacetic acids in drinking water by liquid-liquid extraction, and then selecting a silane reagent to perform derivatization, wherein the reaction mechanism is shown in a formula (1). Through optimizing capillary chromatographic column, injection port temperature, temperature raising program and characteristic ion of haloacetic acid, 7 kinds of Selective Ion (SIM) analysis methods of haloacetic acid are established. Provides an efficient, simple and sensitive analysis method for detecting the haloacetic acid in the drinking water.
The technical scheme of the invention has the following advantages:
(1) The invention uses silane reagent to replace active hydrogen in haloacetic acid molecules, reduces the polarity of the haloacetic acid, increases the volatility of the haloacetic acid, and enables the haloacetic acid to be analyzed by gas chromatography-mass spectrometry.
(2) The method avoids the complicated process of diazomethane and acidified methanol derivatization, and saves the analysis time and chemical reagents.
(3) The method has high sensitivity, low detection limit and quantification limit, and can be used for analyzing high-toxicity trace haloacetic acid in drinking water, such as monochloroacetic acid and monoiodoacetic acid.
(4) The method of the invention applies mass spectrum quantification, and avoids the false positive problem of the GC-ECD method.
(5) The invention provides a gas chromatography-mass spectrometry analysis method of haloacetic acid in drinking water, and a GC-MS is used for establishing a quantitative method of haloacetic acid in drinking water. Compared with the prior art, the method overcomes the defects of a standard method (USEPA, 552.3) provided by the United states environmental protection agency, a matching method (GB/T5749-2006) of China 'water quality Standard for Drinking Water' and a diazomethane derivatization method, realizes one-step liquid-liquid extraction, can be used for machine quantification after simple derivatization, and obtains high sensitivity, high recovery rate of added standard, low detection limit of the method and low quantification limit. The method can be used for efficiently, quickly and accurately measuring the haloacetic acid in the drinking water.
Drawings
In order that the present disclosure may be more readily understood, a more particular description of the disclosure will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings
FIG. 1 is a total ion flow diagram of haloacetic acid in drinking water in example 1 of the present invention.
Detailed Description
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Example 1
(1) Sample collection
12 city family tap water samples were collected in Suzhou city, and before collection, water was drained for 3min to ensure that the collected samples were mains tap water, and then the brown glass bottles were washed three times with tap water, and then 500mL of tap water was collected at each point. After water sample collection, the samples were immediately transported to the laboratory at low temperature for storage (8 ℃).
(2) Liquid-liquid extraction
After measuring residual chlorine in water by using DPD reagent, adding ascorbic acid with 110% (molar concentration) of residual chlorine for quenching, and then adding 1mL of concentrated sulfuric acid to ensure that the pH value of the solution is less than 1. 100mL of the aqueous solution was transferred to a 125mL brown glass bottle, and then 15g of anhydrous sodium sulfate and 8mL of methyl t-butyl ether were added. After shaking for 1min, the tube was transferred to a 15mL glass tube. This procedure was repeated twice and the organic phases were combined. After 5g of anhydrous sodium sulfate was added to the organic phase to remove water from the solution, the organic phase was transferred to a new glass test tube, concentrated to 0.2mL at room temperature with nitrogen purge, transferred to a 2mL sample vial with a cannula, added 5. Mu.L of internal standard (1, 2-dibromopropane) and 10. Mu.L of silylation reagent, and reacted in an oven at 50 ℃ for 30min. After the reaction was complete, cool to room temperature and wait for instrumental analysis.
(3) Instrumental analysis
The samples were analyzed using an Agilent 7890 gas chromatograph-5977 mass spectrometer. The specific parameters are as follows: the column was an HP-5ms column (model 30m x 0.25mm x 0.25 μm). The carrier gas is ultra-pure helium (the purity is more than 99.999 percent), and the flow rate of the carrier gas is 1mL/min; the temperature of a sample inlet is 250 ℃; no-shunt sampling is adopted, and the sampling amount is 1 mu L.
The temperature rise program of the column oven is as follows: the initial temperature is 35 ℃ and is kept for 2min, then the temperature is increased to 100 ℃ at the speed of 4 ℃/min and is kept for 2min, then the temperature is increased to 130 ℃ at the speed of 9 ℃/min and is kept for 1min, finally the temperature is increased to 280 ℃ at the speed of 12 ℃/min, and the operation time is 3min. The ion source temperature of the mass spectrometer is 230 ℃, the quadrupole temperature is 150 ℃, and the electron energy is 70eV. The sample analysis used the Selected Ion (SIM) mode, and quantitative ionic and qualitative ionic information for 7 haloacetic acids is shown in table 1 and fig. 1. After the instrument is set, determining the retention time by using a standard substance of haloacetic acid, and then drawing a standard curve by using a mixing plot, wherein the specific content is drawn by using a working curve.
TABLE 1 Retention time, quantitative ions, qualitative ions, method detection limits and quantitative limits (. Mu.g/L) of haloacetic acid in drinking water
It can be seen from table 1 and fig. 1 that the method has better sensitivity, and the detection limit and the quantitative limit of 7 haloacetic acids are mostly lower than 0.05 μ g/L, and much lower than the mainstream haloacetic acid analysis method (the standard method provided by the u.s.national environmental protection agency (USEPA, 552.3) and the supporting method of the "quality standard of drinking water" in china (GB/T5749-2006) and the diazomethane derivatization method), but the treatment process of the method is far simpler than the mainstream haloacetic acid analysis method. In addition, 7 kinds of haloacetic acids have better peak shapes and responses in the HP-5 chromatographic column (figure 1), which indicates that the haloacetic acid chromatographic column is an ideal haloacetic acid analytical chromatographic column.
(4) Drawing working curve
A haloacetic acid batch (1000 mg/L) was purchased and then diluted with methyl t-butyl ether to give 20mg/L,2mg/L and 1mg/L solutions. After adding 100mL of ultrapure water to 8 clean 125mL brown glass bottles, the diluted solutions were used to prepare haloacetic acid solutions having a concentration of 0.01. Mu.L, 0.05. Mu.L, 0.1. Mu.L, 0.5. Mu.L, 1. Mu.L, 5. Mu.L, 10. Mu.L or 20. Mu.L. After acidification with concentrated sulfuric acid, 15g of anhydrous sodium sulfate and 8mL of methyl tert-butyl ether were added. After shaking for 1min, the cells were transferred to a 15mL glass tube. This procedure was repeated twice and the organic phases were combined. After 5g of anhydrous sodium sulfate was added to the organic phase to remove water from the solution, the organic phase was transferred to a new glass test tube, concentrated to 0.2mL at room temperature with nitrogen purge, transferred to a 2mL sample vial with a cannula, added 5. Mu.L of internal injection standard (1, 2-dibromopropane) and 10. Mu.L of silylation reagent, and reacted in an oven at 50 ℃ for 30min. After the reaction was complete, cool to room temperature and wait for instrumental analysis. After being measured by a gas chromatography-mass spectrometer, taking the peak area of the haloacetic acid as a horizontal coordinate and the concentration as a vertical coordinate, performing linear fitting to obtain a working curve of the haloacetic acid, wherein the working curve is specifically shown in table 2.
TABLE 2 fitted curves for haloacetic acid in drinking water
As can be seen from table 2, the working curves for all 7 haloacetic acids were very linear (> 0.99) by silane derivatization, indicating that it can be used for quantitative analysis of haloacetic acids in practical samples.
(5) Sample analysis
The content of 7 kinds of haloacetic acids in 12 household tap water is analyzed and measured by adopting the steps, the peak area is obtained, then the concentration in the drinking water is obtained by utilizing the working curve correction (internal standard method), and the specific result is shown in table 3.
TABLE 3 concentration of haloacetic acid (μ g/L) in city domestic tap water from Suzhou city.
From table 3 it can be concluded that haloacetic acid is present in total in suzhou domestic drinking water, with the average concentrations of dichloroacetic acid, trichloroacetic acid, chlorobromoacetic acid and dibromoacetic acid all >1 μ g/L, with relatively high concentration levels. The concentrations of monochloroacetic acid, bromoacetic acid and monoiodoacetic acid are all less than 1 mug/L, especially the concentration of monoiodoacetic acid is less than 0.1 mug/L. Monoiodoacetic acid is the most toxic disinfection by-product at present, and animal experiments prove that the monoiodoacetic acid has carcinogenicity, so that the development of the disinfection by-product which can detect low concentration but high toxicity has important significance for protecting the safety of drinking water.
(6) Quality control and assurance
In order to examine the reliability of the method, the present invention performs recovery rate monitoring. And (3) selecting a city drinking water sample in Suzhou city to perform parallel sample experiment and matrix standard adding, and determining the precision of the method. In addition, in order to obtain the detection limit of the method, we performed a labeling (0.1. Mu.g/L) of ultrapure water, and then analyzed seven times in parallel.
The limit of detection is determined by the following formula:
MDL＝3.14×S (1)
in the formula, MDL is the detection limit of the method (μ g/L), and S is the standard deviation. Specific results are shown in tables 1 and 4.
TABLE 4 recovery and precision of haloacetic acid in drinking water
As can be seen from Table 4, the recovery rate of the added standard of the method is between 70 and 130 percent, the precision is far less than 30 percent, and the method meets the requirement of the method for analyzing the pollutants in the drinking water.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the spirit or scope of the invention.
Claims (10)
1. A gas chromatography-mass spectrometry analysis method of haloacetic acid in drinking water is characterized by comprising the following steps:
(1) Taking a water sample of the drinking water, adding a residual chlorine quenching agent for quenching, and extracting haloacetic acid in the drinking water by adopting an organic solvent to prepare a sample solution;
(2) Taking haloacetic acid as a standard substance, taking an organic solvent as a solvent, and preparing a mixed standard solution by stepwise dilution;
(3) Detecting and analyzing the mixed standard solution and the sample solution by using a gas chromatography-mass spectrometer;
(4) And (4) drawing a standard curve according to the detection and analysis result in the step (3) and carrying out sample analysis.
2. The gas chromatography-mass spectrometry method of claim 1, wherein in step (1), the haloacetic acid in the drinking water is a disinfection by-product obtained by a disinfection process of the drinking water.
3. The gas chromatography-mass spectrometry method according to claim 1, wherein in step (1), the organic solvent is selected from one or more of methyl tert-butyl ether, n-hexane and ethyl acetate.
4. The gas chromatography-mass spectrometry method according to claim 1, wherein the step (1) comprises the following specific steps: taking a water sample of the drinking water, measuring residual chlorine in the water, adding a residual chlorine quenching agent for quenching, adjusting the pH value to acidity, and adding an injection internal standard and a derivatization reagent to obtain a sample solution.
5. The gas chromatography-mass spectrometry method of claim 4, wherein the pH is <1.
6. The method of claim 4, wherein the derivatizing agent is selected from the group consisting of silylating agents.
7. The gas chromatography-mass spectrometry method of claim 6, wherein the silylating agent is selected from one or more of bis (trimethylsilyl) trifluoroacetamide, N- (t-butyldimethylsilyl) -N-methyltrifluoroacetamide, trimethylchlorosilane, hexamethyldisilazane, and N, N dimethylformamide.
8. The gas chromatography-mass spectrometry method of claim 4, wherein the residual chlorine quencher is ascorbic acid and/or ammonium chloride.
9. The derivatization conditions of the derivatization reagent are as follows: the heating temperature is 25-80 ℃, and the reaction time is 10-30 min.
10. The gas chromatography-mass spectrometry method of claim 1, wherein in step (2), the haloacetic acid is selected from one or more of monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, monobromoacetic acid, dibromoacetic acid, monochloromonobromoacetic acid, and monoiodoacetic acid.
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| CN202210857009.9A CN115236229A (en) | 2022-07-20 | 2022-07-20 | Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water |
| PCT/CN2023/089363 WO2024016761A1 (en) | 2022-07-20 | 2023-04-20 | Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116272919A (en) * | 2023-05-19 | 2023-06-23 | 江苏鑫康生物科技有限公司 | Method for detecting by-products of water disinfection |
| WO2024016761A1 (en) * | 2022-07-20 | 2024-01-25 | 苏州大学 | Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water |
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| CN118191258B (en) * | 2024-05-17 | 2024-09-10 | 同济大学 | Method for identifying key high-toxicity disinfection byproducts in drinking water by taking genotoxicity as guide |
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| KR100919919B1 (en) * | 2007-09-10 | 2009-10-07 | 한국건설기술연구원 | Monitoring Method and System of Trihalomethane Formation Potential and Haloacetic acids Formation Potential in drinking water treatment |
| CN101131381A (en) * | 2007-09-27 | 2008-02-27 | 上海交通大学 | Method for detecting halogen acetic acid in drinking water |
| CN102520083A (en) * | 2011-12-05 | 2012-06-27 | 西安建筑科技大学 | Method for quickly detecting haloacetic acids serving as disinfection byproducts in drinking water |
| US9581578B1 (en) * | 2013-12-19 | 2017-02-28 | Gary L. Emmert | Fully automated sequential injection analysis method for preconcentration of haloacetic acids in drinking water samples |
| CN108828081B (en) * | 2018-04-17 | 2021-02-05 | 南京大学 | Analysis method for simultaneously detecting nine kinds of haloacetic acids and three kinds of oxyhalides in water |
| CN109212050B (en) * | 2018-07-07 | 2021-05-14 | 丁立平 | Gas chromatography for determining nine trace haloacetic acids in barreled drinking water |
| CN115236229A (en) * | 2022-07-20 | 2022-10-25 | 苏州大学 | Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water |
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Cited By (2)
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| WO2024016761A1 (en) * | 2022-07-20 | 2024-01-25 | 苏州大学 | Gas chromatography-mass spectrometry analysis method for haloacetic acid in drinking water |
| CN116272919A (en) * | 2023-05-19 | 2023-06-23 | 江苏鑫康生物科技有限公司 | Method for detecting by-products of water disinfection |
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