Determination of 19 Phenolic Pollutants in Reclaimed Land Samples by Derivation Gas Chromatography-Mass Spectrometry
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摘要:
近年来国家对自然环境的保护愈加重视，更多被破坏或污染的土地需要进行复垦整治。在评价效果时，需要检测酚类等多项污染物指标。采用气相色谱与气相色谱-质谱联用等方法对酚类化合物直接测定时，存在色谱响应值低、稳定性差、检出限高等问题。本文针对复垦土地样品基质复杂、干扰因素多、前处理困难等特点，对该类样品的提取与净化方法进行筛选优化。根据酚类污染物检测中浓度范围大、重现性差等问题，对衍生化与非衍生化效果进行对比确定了提取和净化方法，结合衍生化条件的优化、实际样品测定结果等方面的综合研究，建立了复垦土地样品19种酚类污染物（其中2，4，6-三氯苯酚和2，4，5-三氯苯酚，以及2，3，4，5-四氯酚和2，3，5，6-四氯酚，因无法分离而合并计算）的衍生化气相色谱-质谱检测方法。该方法采用加速溶剂萃取仪，以正己烷-丙酮（体积比1：1）提取样品，提取液经浓缩、净化后，由五氟苄基溴衍生化，气相色谱-质谱联用仪测定。该方法基质加标回收率为73.3%~107.0%，检出限为0.67~3.95μg/kg，相比非衍生化方法的检出限（10~80μg/kg）显著降低；并且衍生物的稳定性更好，色谱响应值更高，各组分表现在色谱图上的峰高（峰面积）更均衡，对于低浓度样品的测定结果更加准确。该方法能有效去除基质干扰，可为复杂基质土壤样品中的酚类污染物痕量检测提供参考。
Abstract:BACKGROUND In recent years, more attention has been paid to the protection of the environment in China. More damaged or polluted land needs to be reclaimed. When evaluating the effect, it is necessary to detect several pollutant indexes for phenolic pollutants. In the direct determination of phenolic compounds by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), there are challenges such as low chromatographic response, poor stability and high detection limit.
OBJECTIVES To establish a method to determine 19 phenolic pollutants in reclaimed land.
METHODS Based on the characteristics of complex matrix, multiple interference factors, and difficult pre-processing of reclaimed land samples, the extraction and purification methods of this type of sample were screened and optimized. The extraction and purification methods were determined by comparing the effects of derivatization and non-derivatization, combined with comprehensive research on the optimization of derivatization conditions and the measurement results of actual samples. A derivatized gas chromatography-mass spectrometry method for detecting 19 phenolic pollutants in reclaimed land samples was established (Among them, 2, 4, 6-trichlorophenol and 2, 4, 5-trichlorophenol, 2, 3, 4, 5-tetrachlorophenol and 2, 3, 5, 6-tetrachlorophenol were combined because of could not be separated). The samples were extracted with n-hexane and acetone (1:1, V/V) by ASE. The extract was concentrated, purified and derivatized by pentafluorobenzyl bromide. Finally, it was determined by GC-MS internal standard method.
RESULTS The standard-addition recoveries were 73.3%-107.0%. The method detection limits of phenolic compounds in soil were 0.67-3.95μg/kg, which was significantly lower than nonderivative method (10-80μg/kg). The derivatives had better stability and higher chromatographic response, the groups were more even in peak height (area) on the chromatogram. The derivatization method had better reproducibility and the results of low-concentration samples were more accurate.
CONCLUSIONS This method can be used effectively to avoid matrix interference and provide reference for trace determination of phenolic pollutants in soil samples with complex matrix.
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表 1 各组分保留时间、定量离子与辅助离子
Table 1. Retention time, quantitative ions and auxiliary ions of each component
序号 化合物 保留时间(min) 定量离子/辅助离子 1 2-氟苯酚-PFB(替代物) 16.19 181/292 2 苯酚-PFB 16.61 181/274 3 苊-d10(内标) 16.83 162/164 4 间-甲酚-PFB 17.89 181/288 5 邻-甲酚-PFB 18.35 181/288 6 对-甲酚-PFB 18.50 181/288 7 2-氯苯酚-PFB 19.65 308 8 2, 4-二甲酚-PFB 19.65 121 9 2, 6-二氯酚-PFB 21.57 181/342 10 4-氯-3-甲基苯酚-PFB 21.98 181/322 11 2, 4-二氯酚-PFB 22.62 181/342 12 2-硝基酚-PFB 23.64 181/319 13 2, 4, 6-三氯苯酚-PFB/2, 4, 5-三氯苯酚-PFB 23.79 181/376 14 2, 4-二硝基酚-PFB 25.19 181/161 15 4-硝基酚-PFB 25.61 181/319 16 2, 3, 4, 6-四氯酚-PFB 26.76 181/412 17 2, 3, 4, 5-四氯酚-PFB/2, 3, 5, 6-四氯酚-PFB 26.91 181/412 18 2, 3, 5, 6-四氯酚-PFB 28.34 181/161 19 2, 4, 6-三溴苯酚-PFB(替代物) 28.47 181/431 20 五氯苯酚-PFB 29.70 181/446 
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表 2 酚类化合物标准曲线
Table 2. Calibration curves of phenolic compounds
化合物 衍生后化合物 标准曲线 相关系数(r2) 2-氟苯酚(替1) 2-氟苯酚-PFB y=-0.0144696+0.00229139x 0.9972 苯酚 苯酚-PFB y=-0.0378798+0.00276533x 0.9981 间-甲酚 间-甲酚-PFB y=-0.0360363+0.00218262x 0.9989 邻-甲酚 邻-甲酚-PFB y=-0.0670299+0.00232614x 0.9977 对-甲酚 对-甲酚-PFB y=-0.0572942+0.0022358x 0.9974 2-氯苯酚 2-氯苯酚-PFB y=-0.102385+0.00450636x 0.9954 2, 4-二甲酚 2, 4-二甲酚-PFB y=-0.105425+0.00450302x 0.9962 2, 6-二氯酚 2, 6-二氯酚-PFB y=-0.0143943+0.00231734x 0.9977 4-氯-3-甲基苯酚 4-氯-3-甲基苯酚-PFB y=-0.10396+0.00239979x 0.9969 2, 4-二氯酚 2, 4-二氯酚-PFB y=-0.138599+0.00289315x 0.9970 2-硝基酚 2-硝基酚-PFB y=-0.0677484+0.00135676x 0.9961 2, 4, 6-三氯苯酚/2, 4, 5-三氯苯酚 2, 4, 6-三氯苯酚-PFB/2, 4, 5-三氯苯酚-PFB y=-0.147103+0.0029088x 0.9966 2, 4-二硝基酚 2, 4-二硝基酚-PFB y=-0.0550873+0.00259657x 0.9984 4-硝基酚 4-硝基酚-PFB y=-0.0800387+0.00145206x 0.9956 2, 3, 4, 6-四氯酚 2, 3, 4, 6-四氯酚-PFB y=-0.141921+0.00277173x 0.9957 2, 3, 4, 5-四氯酚/2, 3, 5, 6-四氯酚 2, 3, 4, 5-四氯酚-PFB/2, 3, 5, 6-四氯酚-PFB y=-0.127976+0.00369817x 0.9954 2-甲基-4, 6-二硝基酚 2-甲基-4, 6-二硝基酚-PFB y=-0.160452+0.00301742x 0.9945 2, 4, 6-三溴苯酚(替2) 2, 4, 6-三溴苯酚-PFB y=-0.144911+0.00221011x 0.9982 五氯苯酚 五氯苯酚-PFB y=-0.145926+0.00302867x 0.9981
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表 3 三种提取方法的检出限、测定下限与精密度与回收率情况
Table 3. Detection limit, determination lower limit, precision and recovery of the three extraction methods
提取方式 方法检出限(μg/kg) 测定下限(μg/kg) 加标回收率(%) 回收率平均值(%) 相对标准偏差平均值(%) 索氏提取 0.97~4.36 3.88~17.4 73.3~102.0 88.9 4.9 超声波提取 0.78~5.06 3.11~20.2 71.4~97.3 82.4 5.4 加速溶剂萃取 0.67~3.95 2.68~15.8 75.4~107.0 91.0 4.4
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表 4 酚类化合物衍生化方法检出限
Table 4. Detection limits of phenolic compounds by derivativation method
化合物 测定值(μg/kg) 相对标准偏差(%) 检出限(μg/kg) 测定下限(μg/kg) 1 2 3 4 5 6 7 2-氟苯酚(替1) 7.05 7.44 9.32 9.40 8.39 9.33 7.68 1.0 3.13 12.5 苯酚 8.02 7.76 9.27 9.44 9.05 9.89 8.40 0.8 2.47 9.88 间-甲酚 8.38 8.41 7.45 8.14 7.88 7.91 8.27 0.3 1.08 4.32 邻-甲酚 9.44 7.74 9.32 8.98 9.66 8.40 9.01 0.7 2.09 8.35 对-甲酚 8.17 8.37 9.04 8.55 9.15 8.80 9.39 0.4 1.39 5.56 2-氯苯酚 8.75 8.47 8.80 8.82 8.87 8.99 9.16 0.2 0.67 2.68 2, 4-二甲酚 8.72 8.64 8.35 8.11 8.40 8.19 7.85 0.3 0.96 3.83 2, 6-二氯酚 8.63 8.86 7.93 8.08 8.43 7.85 8.70 0.4 1.25 5.02 4-氯-3-甲基苯酚 9.43 10.3 8.86 10.5 9.21 9.63 9.96 0.6 1.85 7.42 2, 4-二氯酚 8.62 9.13 9.73 9.98 8.83 8.51 8.74 0.6 1.80 7.19 2-硝基酚 9.89 9.80 9.03 9.28 8.87 10.0 9.96 0.5 1.50 5.99 2, 4, 6-三氯苯酚/2, 4, 5-三氯苯酚 16.1 16.3 16.0 16.3 16.1 15.4 15.1 0.5 1.46 5.85 2, 4-二硝基酚 11.0 10.6 10.3 10.5 11.2 9.97 11.1 0.5 1.47 5.89 4-硝基酚 10.3 10.3 7.72 10.6 8.11 9.11 10.9 1.3 3.95 15.8 2, 3, 4, 6-四氯酚 8.58 9.24 8.51 8.12 8.71 8.31 9.26 0.4 1.37 5.47 2, 3, 4, 5-四氯酚/2, 3, 5, 6-四氯酚 16.9 16.0 16.3 16.6 18.1 16.5 16.5 0.7 2.12 8.49 2-甲基-4, 6-二硝基酚 8.93 8.25 7.73 7.65 8.04 8.78 9.02 0.6 1.78 7.13 2, 4, 6-三溴苯酚(替2) 7.99 8.08 8.64 7.33 7.21 7.87 7.77 0.5 1.50 6.01 五氯苯酚 10.5 10.9 10.3 9.65 11.1 10.8 10.9 0.5 1.54 6.16
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表 5 酚类化合物加标回收率和精密度
Table 5. Spiked recovery and precision tests of phenolic compounds
酚类化合物 加标浓度40μg/kg 加标浓度100μg/kg 加标浓度200μg/kg RSD(%) 回收率(%) RSD(%) 回收率(%) RSD(%) 回收率(%) 2-氟苯酚(替1) 6.6 89.2 9.5 80.8 5.9 86.3 苯酚 6.1 94.4 3.6 85.3 8.1 75.3 间-甲酚 6.7 86.8 2.1 73.3 8.1 74.2 邻-甲酚 5.9 87.5 3.3 79.5 4.5 87.1 对-甲酚 5.5 104.0 4.8 82.1 9.6 83.6 2-氯苯酚 5.9 103.0 5.3 81.2 6.3 83.4 2, 4-二甲酚 5.9 84.5 2.9 82.6 7.0 79.9 2, 6-二氯酚 6.2 86.1 6.7 80.8 7.2 88.6 4-氯-3-甲基苯酚 5.0 107.0 1.8 85.0 9.1 92.6 2, 4-二氯酚 5.4 90.7 8.6 77.4 3.5 86.2 2-硝基酚 5.5 106.0 4.5 88.5 4.6 83.5 2, 4, 6-三氯苯酚/2, 4, 5-三氯苯酚 3.8 75.4 6.0 74.7 7.0 81.1 2, 4-二硝基酚 6.2 91.2 8.3 76.7 3.9 80.3 4-硝基酚 5.1 101.0 1.7 83.1 5.5 102.0 2, 3, 4, 6-四氯酚 3.7 103.0 5.3 83.2 5.8 82.1 2, 3, 4, 5-四氯酚/2, 3, 5, 6-四氯酚 5.9 78.3 8.2 83.5 8.0 103.0 2-甲基-4, 6-二硝基酚 5.5 82.1 6.4 80.8 2.1 73.6 2, 4, 6-三溴苯酚(替2) 4.6 81.7 6.2 73.3 8.2 82.8 五氯苯酚 4.1 105.0 2.4 82.8 8.7 78.4
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表 6 金属矿区复垦土地样品酚类化合物检测结果
Table 6. Analytical results of phenolic compounds in dreclaimed land samples from metal mining areas
酚类化合物 含量(μg/kg) 重复样相对偏差(%) 检出限(μg/kg) 重复样1 重复样2 2-氟苯酚(替1) 109 96.2 6.2 3.13 苯酚 - - - 2.47 间-甲酚 - - - 1.08 邻-甲酚 < LOD < LOD - 2.09 对-甲酚 25.6 31.6 10 1.39 2-氯苯酚 < LOD < LOD - 0.67 2, 4-二甲酚 < LOD < LOD - 0.96 2, 6-二氯酚 - - - 1.25 4-氯-3-甲基苯酚 - - - 1.85 2, 4-二氯酚 2.43 2.32 2.3 1.80 2-硝基酚 122 138 6.2 1.50 2, 4, 6-三氯苯酚/2, 4, 5-三氯苯酚 31.0 27.5 6.0 0.74 2, 4-二硝基酚 7.84 6.87 6.6 1.47 4-硝基酚 - - - 3.95 2, 3, 4, 6-四氯酚 - - - 1.37 2, 3, 4, 5-四氯酚/2, 3, 5, 6-四氯酚 - - - 1.76 2-甲基-4, 6-二硝基酚 - - - 1.78 2, 4, 6-三溴苯酚(替2) 87.6 93.7 3.4 1.50 五氯苯酚 83.1 78.9 2.6 1.54 注：“-”表示未检出；LOD表示检出限。
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