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HJ 699-2014 English PDF

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HJ 699-2014: Water quality. Determination of organochlorine pesticides and chlorobenzenes. Gas chromatography mass spectrometry
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Basic data

Standard ID HJ 699-2014 (HJ699-2014)
Description (Translated English) Water quality. Determination of organochlorine pesticides and chlorobenzenes. Gas chromatography mass spectrometry
Sector / Industry Environmental Protection Industry Standard
Classification of Chinese Standard Z16
Word Count Estimation 24,247
Date of Issue 3/31/2014
Date of Implementation 7/1/2014
Quoted Standard HJ/T 91; HJ/T 194; HJ 442
Regulation (derived from) Ministry of Environmental Protection Notice No. 24 of 2014
Issuing agency(ies) Ministry of Ecology and Environment
Summary This Standard specifies the liquid-liquid extraction Determination of organochlorine pesticides and chlorobenzenes or solid phase extraction/gas chromatography - mass spectrometry. This Standard applies to surface water, groundwater, sewage determination

HJ 699-2014: Water quality. Determination of organochlorine pesticides and chlorobenzenes. Gas chromatography mass spectrometry


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Water quality.Determination of organochlorine pesticides and chlorobenzenes.Gas chromatography mass spectrometry National Environmental Protection Standard of the People's Republic HJ 699-.2014 Water quality organochlorine pesticides and chlorobenzene compounds Gas chromatography-mass spectrometry Water quality-Determination of organochlorine pesticides and Chlorobenzenes- Gas chromatography mass spectrometry Published on.2014-03-31 2014-07-01 Implementation Ministry of Environmental Protection released

Content

Foreword..II 1 Scope 1 2 Normative references 1 3 Principle of the method 1 4 reagents and materials..1 5 instruments and equipment..2 6 samples. 2 7 Analysis step 3 8 Results calculation and representation 4 9 Precision and accuracy 5 10 Quality Assurance and Quality Control..6 11 Waste treatment.7 Appendix A (normative appendix) method detection limit and lower limit of measurement 8 Appendix B (informative) retention time and characteristic ions of the target.10 Appendix C (informative) method precision and accuracy..12

Foreword

To implement the Environmental Protection Law of the People's Republic of China and the Law of the People's Republic of China on Water Pollution Prevention and Control, to protect the environment, This standard is formulated to ensure human health and to regulate the determination methods of organochlorine pesticides and chlorobenzenes in water. This standard specifies gas chromatography-mass spectrometry for the determination of organochlorine pesticides and chlorobenzenes in water. This standard is the first release. Appendix A of this standard is a normative appendix, and Appendix B and Appendix C are informative appendices. This standard was formulated by the Science and Technology Standards Department of the Ministry of Environmental Protection. This standard is mainly drafted by. Taizhou Environmental Monitoring Center Station. This standard is verified by. Jiangsu Environmental Monitoring Center, Hunan Environmental Monitoring Center Station, Nanjing Environmental Monitoring Center Station, Wuxi Environmental Monitoring Center Station, Suzhou Environmental Monitoring Center Station and Changzhou Environmental Monitoring Center Station. This standard was approved by the Ministry of Environmental Protection on March 31,.2014. This standard has been implemented since July 1,.2014. This standard is explained by the Ministry of Environmental Protection. Water quality - Determination of organochlorine pesticides and chlorobenzene compounds - Gas chromatography - mass spectrometry Warning. The reagents and standard solutions used in this method are volatile toxic compounds. The preparation process should be in the fume hood. Carry out the operation; wear protective equipment as required to avoid contact with skin and clothing.

1 Scope of application

This standard specifies liquid-liquid extraction or solid phase extraction/gas chromatography for the determination of organochlorine pesticides and chlorobenzenes in water. Mass spectrometry. This standard applies to surface water, groundwater, domestic sewage, industrial wastewater and seawater organochlorine pesticides and chlorobenzene compounds Determination of matter. The detection limit and the lower limit of determination of the target and its method determined by the method are shown in Appendix A.

2 Normative references

The contents of this standard refer to the terms in the following documents. For undated references, the valid version applies to this standard. HJ/T 91 Surface Water and Wastewater Monitoring Technical Specifications HJ/T 164 Technical Specifications for Groundwater Environmental Monitoring HJ 442 Code for Environmental Monitoring of Coastal Waters

3 Principle of the method

The liquid chlorine extraction or solid phase extraction method is used to extract organochlorine pesticides and chlorobenzene compounds in the sample, and the extract is dehydrated. After concentration, purification and constant volume, separation and detection were carried out by gas chromatography mass spectrometry. According to retention time, fragment ion mass-to-charge ratio and different The ion abundance is qualitative and the internal standard method is used for quantification.

4 reagents and materials

Unless otherwise stated, analytically pure reagents and distilled water in accordance with national standards were used for the analysis. 4.1 n-hexane (C6H14). pesticide residue grade. 4.2 Dichloromethane (CH2Cl2). pesticide residue grade. 4.3 Methanol (CH3OH). pesticide residue grade. 4.4 Ethyl acetate (C4H8O). pesticide residue grade. 4.5 Acetone (C3H6O). pesticide residue level. 4.6 Standard solution of organochlorine pesticide. ρ=10.0mg/L, the solvent is n-hexane. 4.7 Chlorobenzene compound standard solution. ρ = 10.0 mg/L, the solvent is methanol. 4.8 Internal standard stock solution (deuterated 1,4-dichlorobenzene, deuterated phenanthrene, deuterated □). ρ = 4000mg/L, the solvent is methanol. 4.9 Internal standard use solution. ρ=40.0mg/L. Pipette 100.0μl of internal standard stock solution (4.8) into a 10ml volumetric flask with a micro-syringe and dilute to volume with n-hexane (4.1). Mix well. 4.10 Alternative (tetrachloromethane, decabromobiphenyl) standard solution. ρ = 10.0 mg/L, the solvent is methanol. 4.11 Decafluorotriphenylphosphine (DFTPP) solution. ρ = 1000.0 mg/L, the solvent is methanol. 4.12 Decafluorotriphenylphosphine solution Pipette 500.0μl of decafluorotriphenylphosphine solution (4.11) into a 10ml volumetric flask with a micro-syringe, using n-hexane (4.1) Make up to the mark and mix. The standard solution should be sealed after use and stored in a dark place below 4 °C. 4.13 Hydrochloric acid solution (HCl). 1 1. 4.14 Sodium Chloride (NaCl) After burning at 400 ° C for 4 h, it was cooled and placed in a ground glass bottle and stored in a desiccator. 4.15 anhydrous sodium sulfate (Na2SO4) After burning at 400 ° C for 4 h, it was cooled and placed in a ground glass bottle and stored in a desiccator. 4.16 Solid phase extraction cartridge. The filler is C18 or equivalent type or combined packing, commercially available, according to the organic matter in the sample The content determines the amount of filler used. Note 1. If it is confirmed by experiments that the performance requirements of the method can be met, solid phase extraction cartridges or solid phase extraction discs with other fillers can also be used. 4.17 Helium. Purity ≥99.999%. 4.18 Nitrogen. purity ≥ 99.999%.

5 Instruments and equipment

5.1 Gas Chromatography-Mass Spectrometer. EI source. 5.2 Column. quartz capillary column, length 30m, inner diameter 0.25mm, film thickness 0.25μm, stationary phase 35% phenylmethyl Polysiloxane. 5.3 Solid phase extraction device. The flow rate can be adjusted by a vacuum pump with a flow rate range of 1-20 ml/min. 5.4 Oscillator. The oscillation frequency is at least 240 times per minute. 5.5 box type electric furnace. 5.6 separatory funnel. 1000ml. 5.7 Florisil silica column. 500 mg/6 ml, particle size 40 μm, commercially available. Can also buy diatomite homemade silica Column, but must be verified by experiments to meet the requirements of the method characteristics. 5.8 Drying column. glass column with a length of 250mm and an inner diameter of 20mm, and the glass piston is not coated with lubricating oil. At the lower end of the column, put A small amount of glass wool or glass fiber filter paper was added to 10 g of anhydrous sodium sulfate (4.15). Or other similar drying equipment. 5.9 Microinjectors. 10μl, 50μl, 100μl, 250μl. 5.10 Common instruments and equipment used in general laboratories.

6 samples

6.1 Sample collection and preservation Samples were taken using a brown ground bottle with a glass stopper or a brown screw glass bottle with a Teflon liner. Sample collection Immediately after the collection, the pH was adjusted to 2 with a hydrochloric acid solution (4.13), stored at 4 ° C, extracted within 7 days, and analyzed within 40 days. 6.2 Preparation of samples 6.2.1 Liquid-liquid extraction 6.2.1.1 Measure 100.0ml water sample into the separatory funnel, add 20.0μl substitute standard solution (4.10), and mix. 6.2.1.2 Add 10g of sodium chloride (4.14), shake it to complete dissolution, add 15ml of n-hexane (4.1), shake vigorously 15min (pay attention to deflation), let stand for 15min stratification; repeat the extraction once, combine the extract and dehydrate the dried column, thick Shrink to less than 4ml. Note 2. For domestic sewage and industrial wastewater with complex composition, if the emulsification phenomenon is serious during the extraction process, mechanical means should be used. Separation in two phases, including agitation, centrifugation, filtration with glass wool, etc., or by means of freezing; for seawater, high salt work For samples such as industrial wastewater, the amount of sodium chloride should be appropriately reduced. 6.2.1.3 Floris diatomaceous earth purification. Infiltrate Floris diatomaceous earth with 8ml of n-hexane (4.1), before the liquid surface disappears, Transfer the liquid to the small column, wash the concentrating tube with 1~2ml of n-hexane, and wash the liquid together on the column (Note. should always keep filling A liquid level was left over the material, and eluted with 10 ml of acetone/n-hexane (1.9) to collect all the eluents. Note 3. The elution flow rate should be controlled at about 5ml/min during purification; for clean groundwater, surface water and seawater samples, the purification can be omitted. step. 6.2.1.4 Constant volume. Concentrate the eluent to less than 1ml, add 5.0μl internal standard solution (4.9), and use n-hexane (4.1) Allow to 1.0ml, mix, and transfer to the auto-injection vial for testing. 6.2.2 Solid phase extraction 6.2.2.1 Measure.200.0ml water sample, add 10ml methanol (4.3), add 20.0μl substitute standard solution (4.10), mix uniform. 6.2.2.2 Activation. Activate the solid phase extraction cartridge with 5 ml of ethyl acetate (4.4), 5 ml of methanol (4.3) and 10 ml of water. The flow rate is approximately 5 ml/min. Note 4. During the activation process, the liquid level above the solid phase extraction cartridge packing should be prevented from being drained, otherwise it needs to be reactivated. 6.2.2.3 Loading. The water sample is passed through the solid phase extraction cartridge at a flow rate of 10 ml/min. After the sample is applied, it is rinsed with 10 ml of water. The solid phase extraction cartridge is used to drain the cartridge. 6.2.2.4 Elution. elute the solid phase extraction cartridge with 2.5 ml of ethyl acetate (4.4) and 5 ml of dichloromethane (4.2). At about 5 ml/min, the eluate was collected into a concentrating tube. 6.2.2.5 Drying. The eluent is passed through a drying column, and the concentrated tube is washed 2~3 times with a small amount of dichloromethane (4.2) to wash the solution. Dehydrated together through a dry column. All dehydrated eluate was collected into a concentrating tube and concentrated to approximately 3 ml. 6.2.2.6 The conversion solvent is n-hexane, purification and constant volume. see 6.2.1.3 and 6.2.1.4 for the procedure.

7 Analysis steps

7.1 Instrument Reference Conditions 7.1.1 Gas Chromatography Reference Conditions Inlet temperature. 250 ° C, no split injection. Oven temperature. 20/min 5/min80 1min 150 300 5min⎯⎯⎯⎯⎯→ ⎯⎯⎯⎯→°C °C°C( ) °C °C( ). The column flow rate was 1.0 ml/min. 7.1.2 Mass Spectrometry Reference Conditions Transmission line temperature. 300 °C. Ion source temperature. 300 ° C. Ion source electron energy. 70 eV. Quality range. 45-550 amu. Data collection method. Select ion scan (SIM). 7.2 Calibration 7.2.1 Instrument performance check The mass spectrometer was tuned with perfluorotributylamine before use. 1.0μl is required before sample analysis and every 12h of operation A solution of decafluorotriphenylphosphine (DFTPP) (4.12), the entire system of the instrument is inspected, and the abundance of the mass ions obtained should be Meet the requirements of Table 1. Table 1 DFTPP key ion and ion abundance evaluation Mass ion m/z abundance evaluation mass ion m/z abundance evaluation 51 30-60% strength of 198 fragments.199 5-9% strength of 198 fragments 68 Strength less than 69 Fragments 2% 275 Strength 198 Fragments 10-30% 70 strength less than 69 fragments 2% 365 intensity greater than 198 fragments 1% 127 40-60% 441 with a strength of 198 fragments exists but does not exceed the strength of 443 fragments 197 < 1% 442 strength less than 198 fragments greater than 40% of 198 fragments 198 base peak, relative intensity 100% 443 intensity is 442 fragments 17-23% 7.2.2 Drawing of the calibration curve A series of standard solutions for the preparation of organochlorine pesticides, chlorobenzenes and alternatives. The standard series concentrations are. 20.0 μg/L, 50.0 μg/L, 100 μg/L,.200 μg/L, 500 μg/L, 1000 μg/L; respectively added internal standard solution (4.9), The concentration was both.200 μg/L. According to the instrument reference conditions (7.1), the target compounds of different concentrations are obtained. Mass spectrum. The ratio of the concentration of the target compound to the concentration of the internal standard compound is plotted on the abscissa to quantify the ion of the target compound. The ratio of the value to the quantitative ion response value of the internal standard compound is plotted on the ordinate and a standard curve is drawn. 7.3 Sample determination The test sample (6.2) was taken and measured according to the same instrumental analysis conditions as the calibration curve. 7.4 Blank test While analyzing the sample, take the same volume of pure water, and prepare a blank sample according to the preparation of the sample (6.2). The instrumental analysis conditions were the same as those for plotting the calibration curve.

8 Calculation and representation of results

8.1 Qualitative analysis Retention time (RT), fragment ion mass-to-charge ratio, and different ion abundance ratio (Q) of the target compound in the sample Qualitative. For retention times and characteristic ions of organochlorine pesticides and chlorobenzenes, see Appendix B. The retention time of the target compound in the sample versus the desired retention time (ie, the average relative retention time in the standard solution) The relative deviation should be controlled within ±3%; the different fragment ion abundance ratio of the target compound in the sample and the expected Q value (ie, the standard The relative deviation of the average ion abundance ratio of fragment ions in the quasi-solution should be controlled within ±30%. Selected ion scan total ion chromatograms for organochlorine pesticides and chlorobenzene standard materials, see Figure 1. Figure 1 Total ion chromatogram of organochlorine pesticides and chlorobenzenes (SIM) The compounds in the order are in order of retention. 1-deuterated 1,4-dichlorobenzene, 2-1,3,5-trichlorobenzene, 3-1,2,4-trichlorobenzene, 4-1,2,3-trichlorobenzene, 5-1,2,4,5-tetrachlorobenzene, 6-1,2,3,5-tetrachlorobenzene, 7-1,2,3,4- Tetrachlorobenzene, 8-pentachlorobenzene, 9-tetrachloro Xylene, 10-hexachlorobenzene, 11-formal hexachlorocyclohexane, 12-pentachloronitrobenzene, 13-propyl hexachlorocyclohexane, 14-fluorene phenanthrene, 15-phenylene Hexa-6,16-heptachloro, 17-butyl hexa-6, 18-aldrin, 19-diclopropanol, 20-external epoxy heptachlor, 21-epoxy Chlorine, 22-γ-chlordane, 23-o, p'-DDE, 24-α-chlordane, 25-endosulfan 1,26-p, p'-DDE, 27-didecide, 28-o, p-DDD, 29-endrin, 30-p, p'-DDD, 31-o, p'-DDT, 32-endosulfan 2,33-p, p'-DDT, 34-endelide aldehyde, 35- Endosulfan sulfate, 36-methoxydrip, 37-deuterated □, 38-endidone ketone, 39-decachlorobiphenyl. When each compound is retained See Appendix B.1. 8.2 Quantitative analysis The data was collected by selective ion scanning and quantified by internal standard method. The mass concentration of the target in the sample is iρ (μg/L), Calculate according to formula (1). Is V= ρ ×ρ (1) In the formula. Iρ - the concentration of organochlorine pesticides and chlorobenzenes or substitutes in the sample, μg/L; Isρ - the concentration of organochlorine pesticides and chlorobenzenes or substitutes found according to the standard curve, μg/L; V -- sample volume, ml; sV -- water sample volume, ml. 8.3 result representation When the measurement result is greater than 1.00μg/L, the data retains three significant digits; when the result is less than 1.00μg/L, the data Keep two significant digits.

9 Precision and accuracy

9.1 precision Liquid-liquid extraction. The concentrations of organochlorine-containing pesticides and chlorobenzenes in the six laboratories were 0.050 μg/L, A uniform sample of 0.200 μg/L and 0.800 μg/L was measured, and the relative standard deviation in the laboratory was 0.30% to 7.8%. The relative standard deviation between the chambers is 0.04%~17%, the repeatability limit is 0.031~0.80μg/L, and the reproducibility limit is 0.017~1.1μg/L. See Appendix C for precision data. Solid phase extraction. The concentrations of organic pesticides and chlorobenzenes in the 6 laboratories were 0.025 μg/L, 0.100μg/L, 0.400μg/L unified sample was measured, the relative standard deviation in the laboratory was 0.50%~13%, laboratory The relative standard deviation is 0.78%~8.1%, the repeatability limit is 0.015~0.54μg/L, and the reproducibility limit is 0.021~0.69μg/L. See Appendix C for density data. 9.2 Accuracy Liquid-liquid extraction. The concentrations of organochlorine-containing pesticides and chlorobenzenes in the six laboratories were 0.050 μg/L, A uniform sample of 0.200 μg/L and 0.800 μg/L was analyzed and determined, and the recoveries ranged from 73.6% to 116%. specific See Appendix C for accuracy data. Solid phase extraction. The concentrations of organic pesticides and chlorobenzenes in the 6 laboratories were 0.025 μg/L, A uniform sample of 0.100μg/L and 0.400μg/L was analyzed and determined, and the recoveries ranged from 36.6% to 124%. specific See Appendix C for accuracy data. 10 Quality Assurance and Quality Control 10.1 Instrument performance test The gas chromatography mass spectrometry system should be inspected and injected separately before the sample analysis and every 12 hours of operation. 1.0μlp, p'-DDT (1.0mg/L) and 1.0μl endrin (1.0mg/L), the degradation rate was determined, and the formula is shown in formula (2). ~(4). If the degradation rate of DDT is ≥20%, or the degradation rate of endrin is ≥20%, or the total degradation rate is ≥30%, then it should be The sample and column are maintained, and the system can be tested before passing the test. (p,p'-DDE p,p'-DDD) = 100% p,p'-DDE p,p'-DDD p,p'-DDT × concentration of DDT degradation rate % ( ) concentration (2) ( ) = 100% × Detergent reagent aldehyde endrin ketone concentration Endrin's degradation rate % (endrin's dipyridyl aldehyde aldehyde ide ketone) concentration (3) = % % total degradation rate % DDT degradation rate endrin degradation rate (4) 10.2 Blank test At least one blank test, that is, a full program blank test, is performed for each batch of samples. If the target compound is detected, it should be identified the reason. 10.3 Calibration The correlation curve of the standard curve should be greater than 0.995. Standard curve check using the intermediate curve concentration point of the standard curve every 12 hours, the measured value and standard value of the target compound The deviation should be within ±20%, otherwise the standard curve should be redrawn. The deviation of cρ from the initial calibration curve iρ (D%), Calculate according to formula (5). Ci -D% 100%ρ ρ= ×ρ (5) In the formula. D%--the relative deviation of the calculated concentration of the calibrator from the standard concentration; Iρ - the standard concentration of the calibrant; Cρ - the calibrant concentration determined by the selected quantitative method. 10.4 Parallel sample determination At least 10% of the parallel samples should be determined for each batch of samples. When the number of samples is less than 10, at least one parallel double should be determined. kind. When the measurement result is within 10 times the detection limit (including the detection limit of 10 times), the relative deviation of the results of the parallel double sample determination should be ≤50%; When the measurement result is greater than 10 times the detection limit, the relative deviation of the parallel double sample measurement results should be ≤ 20%. 10.5 Determination of sample spike recovery Each batch of samples shall be tested at least once for the spiked recovery rate. The spiked recovery rate of the actual sample shall be within the allowable range. The method performance indicators are consistent. 10.6 Determination of alternative recyclables 10.6.1 Liquid-liquid extraction The recovery rate (%) of tetrachloromethane and decachlorobiphenyl should be in the range of 80% to 120%, otherwise the sample should be reprocessed. 10.6.2 Solid phase extraction The recovery rate (%) of tetrachloromethylene should be in the range of 30% to 120%, and the recovery rate (%) of decabromobiphenyl should be Within the range of 60% to 120%, otherwise the sample should be reprocessed. 11 Waste treatment A large amount of waste liquid generated during the experiment should be stored in a suitable closed container; used silicon during the experiment Glue and Floris diatomaceous earth are hazardous wastes. After the experiment is over, they should be disposed of by qualified units.

Appendix A

(normative appendix) Method detection limit and lower limit of measurement The detection limit and lower limit of determination of the target are given in Appendix A.1. Schedule A.1 Method detection limit and lower limit of measurement unit. μg/L Serial number target compound Liquid-liquid extraction (sample volume is 100ml) Solid phase extraction (sample volume is.200ml) Method detection limit lower limit method detection limit lower limit 1 1,3,5-trichlorobenzene 0.037 0.15 0.030 0.12 2 1,2,4-trichlorobenzene 0.038 0.16 0.027 0.11 3 1,2,3-trichlorobenzene 0.046 0.19 0.028 0.12 4 1,2,4,5-tetrachlorobenzene 0.038 0.16 0.021 0.084 5 1,2,3,5-tetrachlorobenzene 0.038 0.16 0.024 0.096 6 1,2,3,4-tetrachlorobenzene 0.038 0.16 0.025 0.10 7 pentachlorobenzene 0.043 0.18 0.030 0.12 8 Hexachlorobenzene 0.043 0.18 0.026 0.11 9 body six six six six 0.056 0.23 0.025 0.10 10 pentachloronitrobenzene 0.036 0.15 0.021 0.084 11 乙六六六0.025 0.10 0.022 0.088 12 乙六六六0.037 0.15 0.034 0.14 13 heptachlor 0.042 0.17 0.031 0.13 14 丁体六六六0.060 0.24 0.033 0.14 15 Aldrin 0.035 0.14 0.069 0.28 16 dicofol 0.031 0.13 0.025 0.10 17 outer epoxy heptachlor 0.053 0.22 0.031 0.13 18 epoxy heptachlor 0.040 0.16 0.026 0.11 19 γ-chlordane 0.044 0.18 0.032 0.13 20 o,p'-DDE 0.046 0.19 0.027 0.11 21 α-Chlorine 0.055 0.22 0.027 0.11 22 endosulfan 1 0.032 0.13 0.033 0.14 Serial number target compound Liquid-liquid extraction (sample volume is 100ml) Solid phase extraction (sample volume is.200ml) Method detection limit lower limit method detection limit lower limit 23 p,p'-DDE 0.036 0.15 0.027 0.11 24 dieldrin 0.043 0.18 0.027 0.11 25 o,p-DDD 0.038 0.16 0.025 0.10 26 Endrin 0.046 0.19 0.056 0.23 27 p,p'-DDD 0.048 0.20 0.028 0.12 28 o,p'-DDT 0.031 0.13 0.031 0.13 29 endosulfan 2 0.044 0.18 0.037 0.15 30 p,p'-DDT 0.043 0.18 0.032 0.13 31 Endrin aldehyde 0.051 0.16 0.029 0.12 32 endosulfan sulfate 0.043 0.18 0.024 0.10 33 methoxychlor 0.093 0.16 0.065 0.26 34 Endrin ketone 0.046 0.19 0.031 0.13 Note. The detection limit of DHS and DDT cannot meet the limit requirements of “Groundwater Quality Standard” (GB/T 14848-93). The method of increasing the sampling volume meets the limit requirements.

Appendix B

(informative appendix) Target retention time and characteristic ions Table B.1 gives the measured parameters such as the peak order, retention time, target ion and auxiliary ions of the target. Schedule B.1 Retention time and characteristic ions of organochlorine pesticides and chlorobenzenes No. Compound name retention time target ion auxiliary ion remark 1 deuterated 1,4-dichlorobenzene 4.452 150 115 internal standard compound 2 1,3,5-trichlorobenzene 4.903 180 74,145 target compound 3 1,2,4-trichlorobenzene 5.402 180 145, 74 target compound 4 1,2,3-trichlorobenzene 5.756 180 145,109 target compound 5 1,2,4,5-tetrachlorobenzene 6.666 216 179,74 target compound 6 1,2,3,5-tetrachlorobenzene 6.593 216 179,74 target compound 7 1,2,3,4-tetrachlorobenzene 7.043 21...

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