2，4-滴丁酯环境行为研究
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摘要
2,4-滴丁酯环境行为研究旨在阐明2,4-滴丁酯在环境中的归宿和潜在危害,为其科学合理使用和环境安全性评价提供科学依据。本文建立了2,4-滴丁酯残留分析方法。并通过此方法研究了2,4-滴丁酯的水解、光解、土壤降解、土壤吸附及淋溶迁移等环境行为特性。
建立了土壤和水样中2,4-滴丁酯GC检测方法。在0.05-10 mg·L-1范围内,2,4-滴丁酯峰面积和浓度间相关性良好,线性回归方程：y=33371x-7189.8,相关系数x=0.997 4；水样中添加0.005-0.1 mg·L-1,2,4-滴丁酯的平均回收率是100.63%,变异系数1.30%；土壤中添加0.01、0.1mg·kg-1,2,4-滴丁酯的平均回收率102.15%,变异系数4.99%；2,4-滴丁酯在水中的最低检测浓度为0.005mg·L-1；土壤中的最低检测浓度为0.05 mg·kg-1。该方法满足残留分析检测的要求,为研究2,4-滴丁酯环境行为奠定了基础。
2,4-滴丁酯在缓冲溶液中水解速率依次为：pH9>pH7>pH5,水解半衰期(25℃)分别为10.7 min、5.8 d、23.5 d。水解反应是碱催化水解,pH值是决定因素；温度对2,4-滴丁酯的水解影响明显,随温度升高,降解加快。在15℃到35℃范围内,温度每提高10℃,水解速率增加1.57倍；2,4-滴丁酯水解反应的活化能与温度之间无明显相关性,而活化熵与温度呈显著的相关性,相关系数r=1；活化熵为负值说明水解反应由活化熵的增加所驱动；2,4-滴丁酯水解产物甲酯化衍生后,经GC-MS鉴定,根据其结构推测,2,4-滴丁酯的水解机制是先发生酯键断裂生成2,4-二氯苯氧乙酸,再进一步醚键断裂生成2,4-二氯苯酚。
2,4-滴丁酯在不同溶剂中的光解存在明显差异,在正己烷中光解速率最快,其次是甲醇,而在丙酮中几乎无降解；光解同时受初始浓度的影响,2,4-滴丁酯在正己烷中的光解随浓度不同而异,高浓度光解缓慢,低浓度光解迅速,可能原因是光能一定的条件下,高浓度使单位分子平均接受的光能减少,发生光降解的几率减少。
2,4-滴丁酯在砂土、壤土和粘土中的降解半衰期分别为10.85d、8.38d、6.94d,在相应灭菌土壤中的降解半衰期分别为46.2d、27.28d和38.93d；通过灭菌和未灭菌土壤中2,4-滴丁酯的降解比较,得出土壤微生物对2,4-滴丁酯的土壤降解起着重要作用；土壤有机质含量因影响土壤微生物的种类和数量而影响2,4-滴丁酯的土壤降解；自然状态下2,4-滴丁酯在土壤中的降解不能很好地符合一级动力学方程,降解同时伴有水解、挥发、光解等多种作用,可能受光强,温差等多种自然因素和其他因素的影响,使降解呈现不规律性。
采用振荡平衡法研究了2,4-滴丁酯的吸附特性。2,4-滴丁酯在三种供试土壤中的吸附均符合Fruendlch等温吸附方程,相关系数r均在0.95以上。在粘土和壤土上的吸附等温线呈L型,在砂土上的吸附等温线呈S型；2,4-滴丁酯在砂土、壤土和粘土中的吸附常数Kd分别为0.96,1.73和5.90,表明其不易被土壤吸附；2,4-滴丁酯在三种土壤中的吸附强弱顺序为：粘土>壤土>砂土,有机质含量增加,吸附能力增强；2,4-滴丁酯在砂土、壤土和粘土中的吸附自由能分别为12.40 kJ·mol-1、12.18 kJ·mol-1、13.82 kJ·mol-1,均小于40kJ·mol-1,表明2,4-滴丁酯在土壤中的吸附属于物理吸附,吸附机理可能有氢键、偶极键作用而不存在化学键吸附作用。
土壤薄层层析法研究了2,4-滴丁酯的移动性。2,4-滴丁酯在三种土壤中的Rr值分别为粘土0.19、壤土0.45、砂土0.56,分别属于第1V等级不易移动、第Ⅲ等级中等移动、第Ⅲ等级中等移动；2,4-滴丁酯在土壤中的移动性强弱顺序为：砂土>壤土>粘土,随土壤有机质含量增加,移动性减弱。
A study to environmental behaviors of 2,4-D butylate was aimed at elucidating 2,4-D butylate fate and potential hazards,and providing a seientifie basis for reasonable using, and evaluating environmental safety.A method for residue determination of 2,4-D butylate was developed. Via this method,environmental behavior of 2,4-D butylate was studied, such as absorption, mobibity,hydrolysis,soil degradation.
An analytical method for determining 2,4-D butylate residues in water and soil by GC-ECD was described. The line equation was y=33371x-7189.8 with the linearty ranging from 0.05-10 mg-L"1, the correlation coefficient r=0.9974. The method had been validated by spiking different concentrations of 2,4-D butylate to soil and water. The result showed that the average recovery for water was 100.63%, spiked at 0.005-0.1 mg-L-1, while the coefficient of variability was 1.30%. The average recovery for soil was 102.15%, spiked at 0.01-0.1 mg-kg-1, while the coefficient of variability was 4.99%. The LOD were 0.005 mg-L-1,0.05 mg-kg-1, for water and soil samples, respectively. It indicated that the developed method could be applied for residue determination and environmental behavior of 2,4-D butylate.
Hydrolysis velocity of 2,4-D butylate in different buffer solutions was in order of pH9>pH7>pH5, while hydrolysis half lives (25℃) were 10.7 min,5.8 d and 23.5 d, reseparately.2,4-D butylate,s hydrolysis was base-catalyzed hydrolysis,which indicated that the pH was a crucial factor. Temperature had a significant effect on 2,4-D butylate's hydrolysis,which was increased with temperature increasing. The hydrolysis velocity increased 1.57 times for each temperatur increase of 10℃. There existed no obvious correlations between the activation energies of 2,4-D butylate hydrolysis and temperatures,but the activationentropy absolute values of 2,4-D butylate hydrolysis increased with the increasing temperatures in the environment. The activationentropy absolute values of 2,4-D butylate hydrolysis was negative,suggesting that hydrolysis of 2,4-D butylate in the aqueous solutions was driven by the activation entropy. The hydrolytic products of 2,4-D butylate were identified as 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenol by GC-MS, suggesting that the degradation route of 2,4-D butylate was mainly via ester bonds and aryl ether bond cleavage.
There was significant difference with the photolytic rate of 2,4-D butylate in different solvents. The photolytic rate of 2,4-D butylate in n-hexane was faster than in methanol, and it would not be degraded in acetone solvent. The photolytic rate was influenced by initial concentration of 2,4-D butylate.The photolytic rate became faster when decreasing concentration of 2,4-D butylate in n-hexane, maybe because higher concentration cause competitivly absorb certain light energy, each molecule got less energy and probability of photolysising.
Half lives of 2,4-D butylate in sand, loam and clay were 10.85d,8.38d and 6.94d, respectively, while in those three sterilized soils,the half lives were46.2d,27.28d and 38.93d, respectively.It indicated that soil microorganisms had s significant effect on the degradation of 2,4-D butylate in soil. The soil organic content influence degradation of 2,4-D butylate in soil through influencing microorganism sort and number.Under field environment, degradation of 2,4-D butylate in soil couldn't followed the first order reaction well,its maybe because degradation often accompanied by hydrolysis, photolysis and volatilize, affected by light intensity, difference in temperature and some other factors.
The adsorption of 2,4-D butylate in three kinds of soils were studied with batch equilibrium technique.Adsorption isotherms of 2,4-D butylate on the soils could be described well by Freundlich equation,correlation coefficent r>0.95. Adsorption isotherm of 2,4-D butylate in clay and loam exhibited L-type isotherm. However, adsorption isotherm of 2,4-D butylate in sand loam was S-type; The adsorption constant (Kd) of 2,4-D butylate in sand, loam and clay was 0.96,1.73 and 5.90 respectively, which suggested that 2,4-D butylate did't easily been adsorbed in soils. Intense extent of 2,4-D butylate adsorbed by three soils in order to clay> loam>sand, which suggested that the soil adsorption capacities of 2,4-D butylate were positively related with the contents of soil organic matter.The amounts of the adsorption free energy (ΔG) of 2,4-D butylate on sand,loam and clay soils were 12.40 kJ-mol-1,12.18 kJ-mol-1,13.82 kJ-mol-1,respectively, (ΔG<40kJ-mol-1)which indicated that the 2,4-D butylate adsorption was dominated by physical adsorption, its adsorption mechanism could be the actions of H-band, dipolar bond, van der waals force and hydrophobic bond, while the chemical bond adsorption action was not existed.
The mobility of 2,4-D butylate in three kinds of soils were studied with soil thin layer chromatography. Rf(relative flow) of 2,4-D butylate in clay, loam sand were 0.19, 0.45,0.56,respectively. The mobility of methomyl in three soils above mentioned was shown as don't easily mobile and belonged to grade IV pesticide,middling mobile and belonged to grade III pesticide, middling mobile and belonged to gradeⅢpesticide, respectively.The transportation sequence of 2,4-D butylate in the tested soils was sand> loam> clay.2,4-D butylate move to weaken with the increas of soil organic matter content.
建立了土壤和水样中2,4-滴丁酯GC检测方法。在0.05-10 mg·L-1范围内,2,4-滴丁酯峰面积和浓度间相关性良好,线性回归方程：y=33371x-7189.8,相关系数x=0.997 4；水样中添加0.005-0.1 mg·L-1,2,4-滴丁酯的平均回收率是100.63%,变异系数1.30%；土壤中添加0.01、0.1mg·kg-1,2,4-滴丁酯的平均回收率102.15%,变异系数4.99%；2,4-滴丁酯在水中的最低检测浓度为0.005mg·L-1；土壤中的最低检测浓度为0.05 mg·kg-1。该方法满足残留分析检测的要求,为研究2,4-滴丁酯环境行为奠定了基础。
2,4-滴丁酯在缓冲溶液中水解速率依次为：pH9>pH7>pH5,水解半衰期(25℃)分别为10.7 min、5.8 d、23.5 d。水解反应是碱催化水解,pH值是决定因素；温度对2,4-滴丁酯的水解影响明显,随温度升高,降解加快。在15℃到35℃范围内,温度每提高10℃,水解速率增加1.57倍；2,4-滴丁酯水解反应的活化能与温度之间无明显相关性,而活化熵与温度呈显著的相关性,相关系数r=1；活化熵为负值说明水解反应由活化熵的增加所驱动；2,4-滴丁酯水解产物甲酯化衍生后,经GC-MS鉴定,根据其结构推测,2,4-滴丁酯的水解机制是先发生酯键断裂生成2,4-二氯苯氧乙酸,再进一步醚键断裂生成2,4-二氯苯酚。
2,4-滴丁酯在不同溶剂中的光解存在明显差异,在正己烷中光解速率最快,其次是甲醇,而在丙酮中几乎无降解；光解同时受初始浓度的影响,2,4-滴丁酯在正己烷中的光解随浓度不同而异,高浓度光解缓慢,低浓度光解迅速,可能原因是光能一定的条件下,高浓度使单位分子平均接受的光能减少,发生光降解的几率减少。
2,4-滴丁酯在砂土、壤土和粘土中的降解半衰期分别为10.85d、8.38d、6.94d,在相应灭菌土壤中的降解半衰期分别为46.2d、27.28d和38.93d；通过灭菌和未灭菌土壤中2,4-滴丁酯的降解比较,得出土壤微生物对2,4-滴丁酯的土壤降解起着重要作用；土壤有机质含量因影响土壤微生物的种类和数量而影响2,4-滴丁酯的土壤降解；自然状态下2,4-滴丁酯在土壤中的降解不能很好地符合一级动力学方程,降解同时伴有水解、挥发、光解等多种作用,可能受光强,温差等多种自然因素和其他因素的影响,使降解呈现不规律性。
采用振荡平衡法研究了2,4-滴丁酯的吸附特性。2,4-滴丁酯在三种供试土壤中的吸附均符合Fruendlch等温吸附方程,相关系数r均在0.95以上。在粘土和壤土上的吸附等温线呈L型,在砂土上的吸附等温线呈S型；2,4-滴丁酯在砂土、壤土和粘土中的吸附常数Kd分别为0.96,1.73和5.90,表明其不易被土壤吸附；2,4-滴丁酯在三种土壤中的吸附强弱顺序为：粘土>壤土>砂土,有机质含量增加,吸附能力增强；2,4-滴丁酯在砂土、壤土和粘土中的吸附自由能分别为12.40 kJ·mol-1、12.18 kJ·mol-1、13.82 kJ·mol-1,均小于40kJ·mol-1,表明2,4-滴丁酯在土壤中的吸附属于物理吸附,吸附机理可能有氢键、偶极键作用而不存在化学键吸附作用。
土壤薄层层析法研究了2,4-滴丁酯的移动性。2,4-滴丁酯在三种土壤中的Rr值分别为粘土0.19、壤土0.45、砂土0.56,分别属于第1V等级不易移动、第Ⅲ等级中等移动、第Ⅲ等级中等移动；2,4-滴丁酯在土壤中的移动性强弱顺序为：砂土>壤土>粘土,随土壤有机质含量增加,移动性减弱。
A study to environmental behaviors of 2,4-D butylate was aimed at elucidating 2,4-D butylate fate and potential hazards,and providing a seientifie basis for reasonable using, and evaluating environmental safety.A method for residue determination of 2,4-D butylate was developed. Via this method,environmental behavior of 2,4-D butylate was studied, such as absorption, mobibity,hydrolysis,soil degradation.
An analytical method for determining 2,4-D butylate residues in water and soil by GC-ECD was described. The line equation was y=33371x-7189.8 with the linearty ranging from 0.05-10 mg-L"1, the correlation coefficient r=0.9974. The method had been validated by spiking different concentrations of 2,4-D butylate to soil and water. The result showed that the average recovery for water was 100.63%, spiked at 0.005-0.1 mg-L-1, while the coefficient of variability was 1.30%. The average recovery for soil was 102.15%, spiked at 0.01-0.1 mg-kg-1, while the coefficient of variability was 4.99%. The LOD were 0.005 mg-L-1,0.05 mg-kg-1, for water and soil samples, respectively. It indicated that the developed method could be applied for residue determination and environmental behavior of 2,4-D butylate.
Hydrolysis velocity of 2,4-D butylate in different buffer solutions was in order of pH9>pH7>pH5, while hydrolysis half lives (25℃) were 10.7 min,5.8 d and 23.5 d, reseparately.2,4-D butylate,s hydrolysis was base-catalyzed hydrolysis,which indicated that the pH was a crucial factor. Temperature had a significant effect on 2,4-D butylate's hydrolysis,which was increased with temperature increasing. The hydrolysis velocity increased 1.57 times for each temperatur increase of 10℃. There existed no obvious correlations between the activation energies of 2,4-D butylate hydrolysis and temperatures,but the activationentropy absolute values of 2,4-D butylate hydrolysis increased with the increasing temperatures in the environment. The activationentropy absolute values of 2,4-D butylate hydrolysis was negative,suggesting that hydrolysis of 2,4-D butylate in the aqueous solutions was driven by the activation entropy. The hydrolytic products of 2,4-D butylate were identified as 2,4-dichlorophenoxyacetic acid and 2,4-dichlorophenol by GC-MS, suggesting that the degradation route of 2,4-D butylate was mainly via ester bonds and aryl ether bond cleavage.
There was significant difference with the photolytic rate of 2,4-D butylate in different solvents. The photolytic rate of 2,4-D butylate in n-hexane was faster than in methanol, and it would not be degraded in acetone solvent. The photolytic rate was influenced by initial concentration of 2,4-D butylate.The photolytic rate became faster when decreasing concentration of 2,4-D butylate in n-hexane, maybe because higher concentration cause competitivly absorb certain light energy, each molecule got less energy and probability of photolysising.
Half lives of 2,4-D butylate in sand, loam and clay were 10.85d,8.38d and 6.94d, respectively, while in those three sterilized soils,the half lives were46.2d,27.28d and 38.93d, respectively.It indicated that soil microorganisms had s significant effect on the degradation of 2,4-D butylate in soil. The soil organic content influence degradation of 2,4-D butylate in soil through influencing microorganism sort and number.Under field environment, degradation of 2,4-D butylate in soil couldn't followed the first order reaction well,its maybe because degradation often accompanied by hydrolysis, photolysis and volatilize, affected by light intensity, difference in temperature and some other factors.
The adsorption of 2,4-D butylate in three kinds of soils were studied with batch equilibrium technique.Adsorption isotherms of 2,4-D butylate on the soils could be described well by Freundlich equation,correlation coefficent r>0.95. Adsorption isotherm of 2,4-D butylate in clay and loam exhibited L-type isotherm. However, adsorption isotherm of 2,4-D butylate in sand loam was S-type; The adsorption constant (Kd) of 2,4-D butylate in sand, loam and clay was 0.96,1.73 and 5.90 respectively, which suggested that 2,4-D butylate did't easily been adsorbed in soils. Intense extent of 2,4-D butylate adsorbed by three soils in order to clay> loam>sand, which suggested that the soil adsorption capacities of 2,4-D butylate were positively related with the contents of soil organic matter.The amounts of the adsorption free energy (ΔG) of 2,4-D butylate on sand,loam and clay soils were 12.40 kJ-mol-1,12.18 kJ-mol-1,13.82 kJ-mol-1,respectively, (ΔG<40kJ-mol-1)which indicated that the 2,4-D butylate adsorption was dominated by physical adsorption, its adsorption mechanism could be the actions of H-band, dipolar bond, van der waals force and hydrophobic bond, while the chemical bond adsorption action was not existed.
The mobility of 2,4-D butylate in three kinds of soils were studied with soil thin layer chromatography. Rf(relative flow) of 2,4-D butylate in clay, loam sand were 0.19, 0.45,0.56,respectively. The mobility of methomyl in three soils above mentioned was shown as don't easily mobile and belonged to grade IV pesticide,middling mobile and belonged to grade III pesticide, middling mobile and belonged to gradeⅢpesticide, respectively.The transportation sequence of 2,4-D butylate in the tested soils was sand> loam> clay.2,4-D butylate move to weaken with the increas of soil organic matter content.
引文
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