二苯醚和4-溴二苯醚与OH自由基微观反应研究
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摘要
多溴二苯醚(Polybrominated diphenylethers,PBDEs)具有独特的物理性质和稳定的化学结构,因此该类化合物作为阻燃剂被广泛应用到家具和电器行业中,从而造成大气、河流、海洋等环境的污染。目前已有研究表明,多溴二苯醚能在动物脂肪、人体血液和母乳中累积,因此这类含溴有机物在环境中的迁移转化以及与环境中活性自由基的反应机理研究越来越受到人们关注。本文以C_(12)H_(10)O(二苯醚,DPE)和C_(12)H_9OBr(4-溴二苯醚,4-BrDPE)为研究对象,采用激光闪光光解-瞬态吸收光谱技术,同时借助GC-MS、LC-MS、UV-Vis等分析技术考察了C_(12)H_(10)O-HNO_2-CH_3CN-H_2O体系和C_(12)H_9O_Br-HNO_2-CH_3CN-H_2O体系在355 nm激光激发产生的激光闪光光解-瞬态吸收光谱,对相关瞬态吸收峰、瞬态物种及反应速率常数进行了研究,并结合光解产物的分析结果,提出了二苯醚和4-溴二苯醚与OH自由基的反应机理。
本文主要研究内容和结论如下:
研究有氧、无氧条件下355 nm激光闪光光解C_(12)H_(10)O-HNO_2-CH_3CN-H_2O体系的反应。通过对瞬态吸收光谱的解析,并结合衰减动力学曲线分析,得到:
①HNO_2吸收355 nm紫外光光解离产生的OH自由基与二苯醚反应生成C_(12)H_(10)O-OH adduct,该加合物在290～360 nm范围有吸收,其吸收峰位置在330nm。
②无氧条件下C_(12)H_(10)O-OH adduct的一级衰减速率常数为(1.86±0.14)×10~5s~(-1);有氧条件下,其准一级衰减速率常数为(6.6±0.4)×10~6 s~(-1)。GC-MS对无氧条件下的激光闪光光解产物分析结果表明,上述体系光解得到了苯酚、羟基二苯醚、硝基二苯醚等产物。
利用355 nm激光光解N_2饱和条件下C_(12)H_9OBr-HNO_2-CH_3CN-H_2O体系,研究结果表明:
③由于4-溴二苯醚两个苯环结构不同,OH自由基可以进攻不带溴的苯环和带溴的苯环,从而形成两种不同加合物4-BrDPE-OH和4-BrOH-DPE,前者与4-溴二苯醚反应的二级速率常数为(2.19±0.17)×10~6l·mol·s~(-1),后者与4-溴二苯醚反应的二级速率常数为(1.56±0.15)×10~6 l·mol·s~(-1)。
④通过解析得到加合物4-BrDPE-OH的最大吸收峰为330 nm,而4-BrOH-DPE的特征吸收峰在320 nm。
⑤采用LC-MS对光解产物进行分析,发现加合物4-BrDPE-OH、4-BrOH-DPE与4-溴二苯醚反应得到的产物是二聚物。比较了加合物C_(12)H_(10)O-OHadduct和C_(12)H_9OBr-OH adduct的不同衰减途径。
⑥在无氧条件下向C_(12)H_(10)O-HNO_2-CH_3CN-H_2O实验体系中加入苯后进行355 nm激光闪光光解,通过苯与二苯醚对OH自由基的竞争反应并结合动力学推导获得C_(12)H_(10)O-OH adduct的生成速率常数。最终得到,OH自由基与二苯醚的反应速率常数为(1.8±0.8)×10~(10) l·mol~(-1)·s~(-1)。该方法为通过动力学衰减曲线得到生成反应速率常数提供了新思路。
以上研究较详细的阐述了二苯醚、4-溴二苯醚与环境中OH自由基的微观反应机理,为深入了解二苯醚类物质在环境中的光化学转化提供参考,并对下一阶段多溴二苯醚光解的微观反应机理研究具有一定指导意义。
A large number of polybrominated diphenylethers(PBDEs) were used in furniture, electronics and computers in order to meet fire safety regulations.These compounds become increasingly important environmental pollutants since they have been detected frequently in sediments,sewage sludge,and atmosphere throughout the planet,and concern on the environmental safety of some PBDEs which have been detected in animal fat and human blood such as DPE and 4-BrDPE,has prompted people to pay more attention.The reaction between PBDEs and reactive radicals in the natrural environments may be very important to their transformation and removal process.However,few microscopic researches have investigated the kinetics and mechanisms of related chemical processes.In this paper,the photolysis reaction of C_(12)H_(10)O-HNO_2-CH_3CN-H_2O and C_(12)H_9OBr-HNO_2-CH_3CN-H_2O solution system were studied by the 355 nm laser flash photolysis-transient absorption spectra technique respectively,and other complementary analytical techniques such as GC-MS、LC-MS and UV-Vis were used to draw the related mechanisms.
The dissertation is mainly composed of three parts:
In part 1 the main characteristic peaks in the transient absorption spectra were attributed and the decay rate constants were investigated while photolyzing C_(12)H_(10)O-HNO_2-CH_3CN-H_2O solution in the presence or absence of O_2 by 355nm laser light.
a.It was found that the OH radical obtained by the cleavage of nitrous acid could reacted with C_(12)H_(10)O to produce C_(12)H_(10)O-OH adduct,which had absorption peaks at 330 nm.
b.The first order decay constant of C_(12)H_(10)O-OH adduct was measured to be(1.86±0.14)×10~5 s~(-1) in the absence of O_2 and pseudo-first order decay constant was(6.6±0.4)×10~6 s~(-1) in the presence of O_2,respectively.The final photolysis products were identified by GC-MS analysis to be phenol,o-hydroxyldiphenylether, p-hydroxyldiphenylether and p-nitrodiphenylether.
In part 2 the microscopic reaction mechanism of 4-bromodiphenylether(4-BrDPE) with nitrous acid(HNO_2) in the absence of O_2 have been explored by the 355 nm laser flash photolysis technique.
c.It was proposed that OH radical,could added to different phenyl rings of 4-BrDPE to forms 2 adducts,i.e.,4-BrDPE-OH adduct and 4-BrOH-DPE adduct.The first-order decay rate constants of 4-BrDPE-OH adduct and 4-BrOH-DPE adduct were measured to be(2.19±0.04)×10~5 s~(-1) and(1.56±0.03)×10~5 s~(-1),respectively.
d.The absorption peaks of 4-BrDPE-OH adduct and 4-BrOH-DPE adduct were at 330 nm and 320 nm,respectively.
e.The final photolysis product of 4-BrDPE and HNO_2 identified by LC-MS analysis was mainly the dimeric compounds.Compared the different reaction processes of C_(12)H_(10)O-OH adduct and C_(12)H_9OBr-OH adduct.
f.Benzene was added to CH_3CN-H_2O-C_(12)H_(10)O-HNO_2 solution as OH scavenger to acquire the reaction rate constant of OH and C_(12)H_(10)O.The photolysis reaction initiated by 355nm laser light in the absence of O_2 of CH_3CN-H_2O-C_6-H_6-C_(12)H_(10)O-HNO_2 solution was studied by solving related kinetic equations and the reaction rate constant of OH and C_(12)H_(10)O was obtained to be(1.8±0.8)×10~(10) 1·mol~(-1)·s~(-1).
The above research results provide imformation for the deeper understanding of the photo-induced conversions of PBDEs and further microscopic study of photolysis reactions of other PBDEs.
本文主要研究内容和结论如下:
研究有氧、无氧条件下355 nm激光闪光光解C_(12)H_(10)O-HNO_2-CH_3CN-H_2O体系的反应。通过对瞬态吸收光谱的解析,并结合衰减动力学曲线分析,得到:
①HNO_2吸收355 nm紫外光光解离产生的OH自由基与二苯醚反应生成C_(12)H_(10)O-OH adduct,该加合物在290～360 nm范围有吸收,其吸收峰位置在330nm。
②无氧条件下C_(12)H_(10)O-OH adduct的一级衰减速率常数为(1.86±0.14)×10~5s~(-1);有氧条件下,其准一级衰减速率常数为(6.6±0.4)×10~6 s~(-1)。GC-MS对无氧条件下的激光闪光光解产物分析结果表明,上述体系光解得到了苯酚、羟基二苯醚、硝基二苯醚等产物。
利用355 nm激光光解N_2饱和条件下C_(12)H_9OBr-HNO_2-CH_3CN-H_2O体系,研究结果表明:
③由于4-溴二苯醚两个苯环结构不同,OH自由基可以进攻不带溴的苯环和带溴的苯环,从而形成两种不同加合物4-BrDPE-OH和4-BrOH-DPE,前者与4-溴二苯醚反应的二级速率常数为(2.19±0.17)×10~6l·mol·s~(-1),后者与4-溴二苯醚反应的二级速率常数为(1.56±0.15)×10~6 l·mol·s~(-1)。
④通过解析得到加合物4-BrDPE-OH的最大吸收峰为330 nm,而4-BrOH-DPE的特征吸收峰在320 nm。
⑤采用LC-MS对光解产物进行分析,发现加合物4-BrDPE-OH、4-BrOH-DPE与4-溴二苯醚反应得到的产物是二聚物。比较了加合物C_(12)H_(10)O-OHadduct和C_(12)H_9OBr-OH adduct的不同衰减途径。
⑥在无氧条件下向C_(12)H_(10)O-HNO_2-CH_3CN-H_2O实验体系中加入苯后进行355 nm激光闪光光解,通过苯与二苯醚对OH自由基的竞争反应并结合动力学推导获得C_(12)H_(10)O-OH adduct的生成速率常数。最终得到,OH自由基与二苯醚的反应速率常数为(1.8±0.8)×10~(10) l·mol~(-1)·s~(-1)。该方法为通过动力学衰减曲线得到生成反应速率常数提供了新思路。
以上研究较详细的阐述了二苯醚、4-溴二苯醚与环境中OH自由基的微观反应机理,为深入了解二苯醚类物质在环境中的光化学转化提供参考,并对下一阶段多溴二苯醚光解的微观反应机理研究具有一定指导意义。
A large number of polybrominated diphenylethers(PBDEs) were used in furniture, electronics and computers in order to meet fire safety regulations.These compounds become increasingly important environmental pollutants since they have been detected frequently in sediments,sewage sludge,and atmosphere throughout the planet,and concern on the environmental safety of some PBDEs which have been detected in animal fat and human blood such as DPE and 4-BrDPE,has prompted people to pay more attention.The reaction between PBDEs and reactive radicals in the natrural environments may be very important to their transformation and removal process.However,few microscopic researches have investigated the kinetics and mechanisms of related chemical processes.In this paper,the photolysis reaction of C_(12)H_(10)O-HNO_2-CH_3CN-H_2O and C_(12)H_9OBr-HNO_2-CH_3CN-H_2O solution system were studied by the 355 nm laser flash photolysis-transient absorption spectra technique respectively,and other complementary analytical techniques such as GC-MS、LC-MS and UV-Vis were used to draw the related mechanisms.
The dissertation is mainly composed of three parts:
In part 1 the main characteristic peaks in the transient absorption spectra were attributed and the decay rate constants were investigated while photolyzing C_(12)H_(10)O-HNO_2-CH_3CN-H_2O solution in the presence or absence of O_2 by 355nm laser light.
a.It was found that the OH radical obtained by the cleavage of nitrous acid could reacted with C_(12)H_(10)O to produce C_(12)H_(10)O-OH adduct,which had absorption peaks at 330 nm.
b.The first order decay constant of C_(12)H_(10)O-OH adduct was measured to be(1.86±0.14)×10~5 s~(-1) in the absence of O_2 and pseudo-first order decay constant was(6.6±0.4)×10~6 s~(-1) in the presence of O_2,respectively.The final photolysis products were identified by GC-MS analysis to be phenol,o-hydroxyldiphenylether, p-hydroxyldiphenylether and p-nitrodiphenylether.
In part 2 the microscopic reaction mechanism of 4-bromodiphenylether(4-BrDPE) with nitrous acid(HNO_2) in the absence of O_2 have been explored by the 355 nm laser flash photolysis technique.
c.It was proposed that OH radical,could added to different phenyl rings of 4-BrDPE to forms 2 adducts,i.e.,4-BrDPE-OH adduct and 4-BrOH-DPE adduct.The first-order decay rate constants of 4-BrDPE-OH adduct and 4-BrOH-DPE adduct were measured to be(2.19±0.04)×10~5 s~(-1) and(1.56±0.03)×10~5 s~(-1),respectively.
d.The absorption peaks of 4-BrDPE-OH adduct and 4-BrOH-DPE adduct were at 330 nm and 320 nm,respectively.
e.The final photolysis product of 4-BrDPE and HNO_2 identified by LC-MS analysis was mainly the dimeric compounds.Compared the different reaction processes of C_(12)H_(10)O-OH adduct and C_(12)H_9OBr-OH adduct.
f.Benzene was added to CH_3CN-H_2O-C_(12)H_(10)O-HNO_2 solution as OH scavenger to acquire the reaction rate constant of OH and C_(12)H_(10)O.The photolysis reaction initiated by 355nm laser light in the absence of O_2 of CH_3CN-H_2O-C_6-H_6-C_(12)H_(10)O-HNO_2 solution was studied by solving related kinetic equations and the reaction rate constant of OH and C_(12)H_(10)O was obtained to be(1.8±0.8)×10~(10) 1·mol~(-1)·s~(-1).
The above research results provide imformation for the deeper understanding of the photo-induced conversions of PBDEs and further microscopic study of photolysis reactions of other PBDEs.
引文
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