模拟太阳光作用下水环境中烷基酚光转化机理研究
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摘要
典型的内分泌干扰物壬基酚（Nonylphenol, NP）和辛基酚（Octylphenol, OP）因其在工业过程的广泛应用，现在普遍存在于水体环境中，且因为其环境持久性、生物累积性及生殖毒性而受到人们的广泛关注。本论文选取4-n-NP、4-t-OP作为研究对象，研究其在水溶液体系中的光化学行为；并着重模拟水环境中各常见环境要素，考察它们对NP、OP光转化影响及作用机制，旨在深入理解NP、OP在水环境中的光转化机理和环境行为。主要研究结论如下：
在实验室控制光转化条件下，通过测定光转化过程中NP、OP的残留率，考察了天然水环境各主要因素（光照强度、温度、浓度、pH、Fe(Ⅲ)、DO、NO_3~-、H_2O_2、HCO_3~-、HA等）对它们光转化的影响。结果表明，DO、NO_3~-、H_2O_2、HA是影响NP、OP在水环境中光转化的重要因素，而温度、光照强度、浓度、Fe(Ⅲ)、pH、HCO_3~-等对APs的转化影响较小。在不同介质（纯水、人工海水和天然海水）中，DO、NO_3~-、H_2O_2、HA均在NP、OP的光转化中起重要作用，但由于不同体系中所含物质的差异性，且主要组分在光转化时生成的活性粒子与NP、OP作用机理不同，导致了不同目标物、不同体系间光转化速率间的差异较大。在此基础上，通过转化中间产物的检测，系统研究NP、OP在水中的光转化机理。
NP在DO作用下产物主要有4-壬基~-邻苯二酚、壬醇、壬醛和壬酸，其中以壬酸为主。推测NP在O_2-作用下，生成邻酚类物质，继续反应转变为邻醌再发生共轭加成；共轭加成产物不稳定，生成壬醇、壬醛和壬酸。H_2O_2光照生成的OH进攻NP的三个电子云较集中的位置（即碳链末端、酚羟基邻位、连接苯环的烷基碳），主要转化产物有碳链缩短（2-8碳）的酚、4-壬基~-邻苯二酚、壬醇、壬醛、壬酸，其中以壬醛为主。NO_3~-在光照下同时生成OH与NO_2，因此具有与H_2O_2存在时相同的作用机制和转化产物；另外NO_2能硝化NP，检测到2-硝基-4-壬基酚。当OH过剩时Cl~-的存在有利于OH的充分利用，能够进一步促进反应的进行，当OH较少时则会与NP竞争从而产生抑制作用。转化产物与H_2O_2单独存在时相同，另外还检测到壬酰氯，其前驱体可能是壬醛。在天然海水中检测到的NP转化产物为4-壬基-邻苯二酚，而其他小分子产物并未检测到，可能是因为在天然海水中存在的活性粒子较多，反应路径较多，产物并不单一，以至最终小分子产物的量比较少，而难以被检测到。
水溶液中DO作用下OP的光转化主要产物是4-叔辛基-邻苯二酚。推测反应机理为：吸收光能处于激发态的OP被O_2~-攻击，生成邻酚类物质。由于未检测到其他小分子产物的存在，邻酚类产物的进一步转化途径尚难推测。水溶液中的H_2O_2在光照下生成OH，在其作用下OP的主要转化产物有4-叔辛基-邻苯二酚、戊基酚（以前者为主）。推测转化机理为： OH进攻OP的酚羟基邻位，生成4-叔辛基-邻苯二酚；同时OP在OH作用下烷基链末端的叔碳脱掉一个小分子醇，转变为相对较不稳定的仲碳结构，仲碳结构经过重排，转变为两个叔碳直接相连的庚基。但是在光转化后样品中并没有检测到这种物质，可能是由于其末端烷基碳相对更活泼，在OH的作用下极易从烷基脱离，烷基碳逐步脱离的结果最终就转变为戊基酚。NO_3~-作用下OP光转化产物主要有4-叔辛基-邻苯二酚和2-硝基-4-叔辛基酚，以硝化产物（后者）累积为主，可能是因为该硝化产物较为稳定。推测该机制下OP的光转化机理是NO_3~-光转化生成的OH与NO_2进攻OP的酚羟基邻位。在天然海水作用下，检测到的OP主要转化产物是2-硝基-4-叔辛基酚，可能是因为在天然海水中OP光转化生成的硝化产物相对比较稳定的原因。
The typical endocrine disrupting chemicals, nonylphenol (NP) and octylphenol(OP), have been widely used in various industrial processes and they are ubiquitous inthe aquatic environment. The strong biologically cumulative effect, stability andestrogenic character of NP and OP have caused public concern. It is therefore of greatsignificance to investigate their environmental fate. The primary route of exposure toNP and OP for human and wildlife is through water, and phototransformation is animportant abiotic process for the elimination of NP and OP in water. Therefore, wechose4-n-NP and4-t-OP as target compounds to investigate theirphototransformation pathways and to elucidate the effects of common waterconstituents on the phototransformation mechanisms of NP and OP. The majorconclusions of the study are as following:
The influence of each common environmental factor on the phototransformationof NP and OP has been assessed through contrasting the residual rate of NP and OP.In pure water, dissolved oxygen (DO) played a key role in the phototransformation ofNP, as the degradation rate obviously decreased when the concentration of DO wasdecreased. Other factors such as NO_3-, HCO_3~-, Fe(Ⅲ), H_2O_2and HA increased thephototransformation of NP. However, the influences of NO_3-, H_2O_2and HA on theNP phototransformation were more obvious. The photolysis rate of NP was morerapid in an alkaline solution than in an acidic medium. In the condition of higher lightintensity or higher temperature, the phototransformation rate of NP increased. Theeffects of common water constituents on the OP phototransformation in pure waterwere also assessed. And DO was also a significant influencing factor on the OPphototransformation and other factors (NO_3~-, H_2O_2, HA) accelerated thephototransformation rate of OP due to their photoactivity. Although the photolysisrates of NP and OP were different in the three water systems, the four factors (DO,NO_3~-, H_2O_2, HA) were significant on the phototransformation of NP and OP.
The phototransformation pathways in different conditions have been proposedaccording to the intermediate products identified by GC-MS. In pure water, when NPreacted with DO,4-nonyl-catechol, nonanol, nonanal and nonoic acid have beenidentified as the major degradation products, while the accumulated amount of nonoicacid was the most. We therefore proposed that4-nonyl-catechol and ortho-quinonederivative were produced after the formation of4-nonylphenoxyl radical andsuperoxide radical anions (O_2~-), then the intermediates underwent conjugate additionto produce nonanol, nonanal and nonoic acid. In the presence of H_2O_2,4-n-akylphenol(HOC_6H_4-CnH_(2n+1), n=2~8),4-nonyl-catechol, nonanol, nonanal and nonoic acid werethe major products, and nonanal was the most accumulated one. We proposed that thehydroxyl radicals (OH) generated by the photolysis of H_2O_2attacked the electronicgathered positions of NP molecules. In the presence of NO_3~-, the same products werealso detected as in the presence of H_2O_2in addition to2-nitryl-4-nonylphenol. Theirradiated NO_3-can produce OH and NO2, and NO_2attacked the ortho position ofphenolic hydroxyl to generate2-nitryl-4-nonylphenol. In the condition of coexistenceof Cl-and H_2O_2in an aqueous solution, two opposite effects of Cl-were observed: itcan make full use of OH with surplus amount of H_2O_2, resulting in an accelerateddegradation rate of NP, while Cl-compete with NP when the amount of H_2O_2is verylimited, leading to a retarded degradation rate of NP. In any case, the same productswere detected in the coexistence of Cl-and H_2O_2as in the presence of H_2O_2, inaddition to nonanoyl chloride. The fact that nonanal was the most accumulatedproduct let us believe that it was most probable that the chlorine radical (·Cl)(generated from the reaction of OH and Cl-) reacted with nonanal to producenonanoyl chloride.
The degradation rate of NP in natural seawater was slower than in pure water.Only4-nonylcatechol was identified as the intermediate, no other products werefound in the irradiated samples. There are many photoactive species in naturalseawater. These species may rapidly react with intermediate products. This may bethe reason why it is difficult to detect those small molecules.
When OP reacted with DO,4-octylcatechol was the main degradation product.The proposed mechanism was that4-octylcatechol derivative was produced after theformation of4-nonylphenoxyl radical and superoxide radical anions (O_2~-). However,since other small molecules were not detected during the process of OP degradation, itis not possible to propose further transformation pathways of4-octylcatechol. In thepresence of H_2O_2, OH generated by the photolysis of H_2O_2is the active species toreact with OP.4-octylcatechol and4-amylphenol were found in this condition and theformer one was the most abundant intermediate. The proposed mechanism was that4-octylcatechol was formed after that· OH attacked the ortho position of phenolichydroxyl. Also, with the reaction of·OH，tertiary carbon turned to secondary carbon,then after the rearrangement of secondary carbon structure, the heptylphenol that hastwo tertiary carbons was formed. However, heptylphenol was not detected in thephotolysis samples due to its very active nature of OH. At last,4-amylphenol wasformed. In the presence of NO_3-,2-nitryl-4-octylphenol and4-octylcatechol werefound as the intermediate products and the former one was the most accumulatedproduct of OP phototransformation owing to the stability of2-nitryl-4-octylphenol.We proposed that OH and NO2(produced by irradiated NO_3-) attacked the orthoposition of phenolic hydroxyl. In natural seawater, the phototransformation of OP wasslower than in pure water. The existence of many species in natural seawater maycompete with OP, resulting in a retarded degradation of OP. The main intermediateproduct of OP phototransformation in natural seawater was2-nitryl-4-octylphenol,while other products were not detected. We therefore postulated that the existence ofNO_3-may play a key role in degradation of OP in natural seawater. This is obviouslydifferent from the case of NP phototransformation in natural seawater. The alkylchain of OP may be responsible for its different pathway of photolysis in naturalseawater and the stability of2-nitryl-4-octylphenol may account for the fact that itwas the only product detected during OP phototransformation.
在实验室控制光转化条件下，通过测定光转化过程中NP、OP的残留率，考察了天然水环境各主要因素（光照强度、温度、浓度、pH、Fe(Ⅲ)、DO、NO_3~-、H_2O_2、HCO_3~-、HA等）对它们光转化的影响。结果表明，DO、NO_3~-、H_2O_2、HA是影响NP、OP在水环境中光转化的重要因素，而温度、光照强度、浓度、Fe(Ⅲ)、pH、HCO_3~-等对APs的转化影响较小。在不同介质（纯水、人工海水和天然海水）中，DO、NO_3~-、H_2O_2、HA均在NP、OP的光转化中起重要作用，但由于不同体系中所含物质的差异性，且主要组分在光转化时生成的活性粒子与NP、OP作用机理不同，导致了不同目标物、不同体系间光转化速率间的差异较大。在此基础上，通过转化中间产物的检测，系统研究NP、OP在水中的光转化机理。
NP在DO作用下产物主要有4-壬基~-邻苯二酚、壬醇、壬醛和壬酸，其中以壬酸为主。推测NP在O_2-作用下，生成邻酚类物质，继续反应转变为邻醌再发生共轭加成；共轭加成产物不稳定，生成壬醇、壬醛和壬酸。H_2O_2光照生成的OH进攻NP的三个电子云较集中的位置（即碳链末端、酚羟基邻位、连接苯环的烷基碳），主要转化产物有碳链缩短（2-8碳）的酚、4-壬基~-邻苯二酚、壬醇、壬醛、壬酸，其中以壬醛为主。NO_3~-在光照下同时生成OH与NO_2，因此具有与H_2O_2存在时相同的作用机制和转化产物；另外NO_2能硝化NP，检测到2-硝基-4-壬基酚。当OH过剩时Cl~-的存在有利于OH的充分利用，能够进一步促进反应的进行，当OH较少时则会与NP竞争从而产生抑制作用。转化产物与H_2O_2单独存在时相同，另外还检测到壬酰氯，其前驱体可能是壬醛。在天然海水中检测到的NP转化产物为4-壬基-邻苯二酚，而其他小分子产物并未检测到，可能是因为在天然海水中存在的活性粒子较多，反应路径较多，产物并不单一，以至最终小分子产物的量比较少，而难以被检测到。
水溶液中DO作用下OP的光转化主要产物是4-叔辛基-邻苯二酚。推测反应机理为：吸收光能处于激发态的OP被O_2~-攻击，生成邻酚类物质。由于未检测到其他小分子产物的存在，邻酚类产物的进一步转化途径尚难推测。水溶液中的H_2O_2在光照下生成OH，在其作用下OP的主要转化产物有4-叔辛基-邻苯二酚、戊基酚（以前者为主）。推测转化机理为： OH进攻OP的酚羟基邻位，生成4-叔辛基-邻苯二酚；同时OP在OH作用下烷基链末端的叔碳脱掉一个小分子醇，转变为相对较不稳定的仲碳结构，仲碳结构经过重排，转变为两个叔碳直接相连的庚基。但是在光转化后样品中并没有检测到这种物质，可能是由于其末端烷基碳相对更活泼，在OH的作用下极易从烷基脱离，烷基碳逐步脱离的结果最终就转变为戊基酚。NO_3~-作用下OP光转化产物主要有4-叔辛基-邻苯二酚和2-硝基-4-叔辛基酚，以硝化产物（后者）累积为主，可能是因为该硝化产物较为稳定。推测该机制下OP的光转化机理是NO_3~-光转化生成的OH与NO_2进攻OP的酚羟基邻位。在天然海水作用下，检测到的OP主要转化产物是2-硝基-4-叔辛基酚，可能是因为在天然海水中OP光转化生成的硝化产物相对比较稳定的原因。
The typical endocrine disrupting chemicals, nonylphenol (NP) and octylphenol(OP), have been widely used in various industrial processes and they are ubiquitous inthe aquatic environment. The strong biologically cumulative effect, stability andestrogenic character of NP and OP have caused public concern. It is therefore of greatsignificance to investigate their environmental fate. The primary route of exposure toNP and OP for human and wildlife is through water, and phototransformation is animportant abiotic process for the elimination of NP and OP in water. Therefore, wechose4-n-NP and4-t-OP as target compounds to investigate theirphototransformation pathways and to elucidate the effects of common waterconstituents on the phototransformation mechanisms of NP and OP. The majorconclusions of the study are as following:
The influence of each common environmental factor on the phototransformationof NP and OP has been assessed through contrasting the residual rate of NP and OP.In pure water, dissolved oxygen (DO) played a key role in the phototransformation ofNP, as the degradation rate obviously decreased when the concentration of DO wasdecreased. Other factors such as NO_3-, HCO_3~-, Fe(Ⅲ), H_2O_2and HA increased thephototransformation of NP. However, the influences of NO_3-, H_2O_2and HA on theNP phototransformation were more obvious. The photolysis rate of NP was morerapid in an alkaline solution than in an acidic medium. In the condition of higher lightintensity or higher temperature, the phototransformation rate of NP increased. Theeffects of common water constituents on the OP phototransformation in pure waterwere also assessed. And DO was also a significant influencing factor on the OPphototransformation and other factors (NO_3~-, H_2O_2, HA) accelerated thephototransformation rate of OP due to their photoactivity. Although the photolysisrates of NP and OP were different in the three water systems, the four factors (DO,NO_3~-, H_2O_2, HA) were significant on the phototransformation of NP and OP.
The phototransformation pathways in different conditions have been proposedaccording to the intermediate products identified by GC-MS. In pure water, when NPreacted with DO,4-nonyl-catechol, nonanol, nonanal and nonoic acid have beenidentified as the major degradation products, while the accumulated amount of nonoicacid was the most. We therefore proposed that4-nonyl-catechol and ortho-quinonederivative were produced after the formation of4-nonylphenoxyl radical andsuperoxide radical anions (O_2~-), then the intermediates underwent conjugate additionto produce nonanol, nonanal and nonoic acid. In the presence of H_2O_2,4-n-akylphenol(HOC_6H_4-CnH_(2n+1), n=2~8),4-nonyl-catechol, nonanol, nonanal and nonoic acid werethe major products, and nonanal was the most accumulated one. We proposed that thehydroxyl radicals (OH) generated by the photolysis of H_2O_2attacked the electronicgathered positions of NP molecules. In the presence of NO_3~-, the same products werealso detected as in the presence of H_2O_2in addition to2-nitryl-4-nonylphenol. Theirradiated NO_3-can produce OH and NO2, and NO_2attacked the ortho position ofphenolic hydroxyl to generate2-nitryl-4-nonylphenol. In the condition of coexistenceof Cl-and H_2O_2in an aqueous solution, two opposite effects of Cl-were observed: itcan make full use of OH with surplus amount of H_2O_2, resulting in an accelerateddegradation rate of NP, while Cl-compete with NP when the amount of H_2O_2is verylimited, leading to a retarded degradation rate of NP. In any case, the same productswere detected in the coexistence of Cl-and H_2O_2as in the presence of H_2O_2, inaddition to nonanoyl chloride. The fact that nonanal was the most accumulatedproduct let us believe that it was most probable that the chlorine radical (·Cl)(generated from the reaction of OH and Cl-) reacted with nonanal to producenonanoyl chloride.
The degradation rate of NP in natural seawater was slower than in pure water.Only4-nonylcatechol was identified as the intermediate, no other products werefound in the irradiated samples. There are many photoactive species in naturalseawater. These species may rapidly react with intermediate products. This may bethe reason why it is difficult to detect those small molecules.
When OP reacted with DO,4-octylcatechol was the main degradation product.The proposed mechanism was that4-octylcatechol derivative was produced after theformation of4-nonylphenoxyl radical and superoxide radical anions (O_2~-). However,since other small molecules were not detected during the process of OP degradation, itis not possible to propose further transformation pathways of4-octylcatechol. In thepresence of H_2O_2, OH generated by the photolysis of H_2O_2is the active species toreact with OP.4-octylcatechol and4-amylphenol were found in this condition and theformer one was the most abundant intermediate. The proposed mechanism was that4-octylcatechol was formed after that· OH attacked the ortho position of phenolichydroxyl. Also, with the reaction of·OH，tertiary carbon turned to secondary carbon,then after the rearrangement of secondary carbon structure, the heptylphenol that hastwo tertiary carbons was formed. However, heptylphenol was not detected in thephotolysis samples due to its very active nature of OH. At last,4-amylphenol wasformed. In the presence of NO_3-,2-nitryl-4-octylphenol and4-octylcatechol werefound as the intermediate products and the former one was the most accumulatedproduct of OP phototransformation owing to the stability of2-nitryl-4-octylphenol.We proposed that OH and NO2(produced by irradiated NO_3-) attacked the orthoposition of phenolic hydroxyl. In natural seawater, the phototransformation of OP wasslower than in pure water. The existence of many species in natural seawater maycompete with OP, resulting in a retarded degradation of OP. The main intermediateproduct of OP phototransformation in natural seawater was2-nitryl-4-octylphenol,while other products were not detected. We therefore postulated that the existence ofNO_3-may play a key role in degradation of OP in natural seawater. This is obviouslydifferent from the case of NP phototransformation in natural seawater. The alkylchain of OP may be responsible for its different pathway of photolysis in naturalseawater and the stability of2-nitryl-4-octylphenol may account for the fact that itwas the only product detected during OP phototransformation.
引文
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