典型芳香烃大气氧化机理研究进展

doi:10.6023/A21050224

化学学报 ›› 2021, Vol. 79 ›› Issue (10): 1214-1231.DOI: 10.6023/A21050224 上一篇下一篇

综述

典型芳香烃大气氧化机理研究进展

宋梦迪, 刘莹, 李歆^*(), 陆思华

北京大学环境科学与工程学院环境模拟与污染控制国家重点联合实验室教育部区域污染控制国际合作联合实验室北京 100871

投稿日期:2021-05-20 发布日期:2021-08-02
通讯作者: 李歆

作者简介:

宋梦迪, 博士研究生, 2019年进入北京大学环境科学与工程学院. 主要研究方向为芳香烃氧化机理及环境效应, 大气挥发性有机物的特征、来源与二次转化, 臭氧污染成因.

刘莹, 博士, 北京大学环境科学与工程学院副研究员. 2007年获北京大学博士学位. 主要研究方向为城市和区域大气有机碳的活性和来源、化学行为及环境影响等, 包括健全和完善有机物在线质谱技术, 开展我国高污染和强氧化性条件下含氧有机物的二次转化机制和化学演变特征、活性有机物的来源及其对二次污染贡献、二次有机气溶胶形成机制等关键科学问题的研究. 承担和参加多项国家自然科学基金、国家重点研发计划、环保部公益项目等.

李歆, 博士, 北京大学环境科学与工程学院青年千人计划研究员, 博士生导师. 2010 年获得北京大学博士学位, 2014年9月~2016年6月就职于德国Juelich研究中心对流层研究所. 2016 年获得北京大学职位. 主要研究方向为大气活性物种的在线监测技术与来源转化机制, 致力于大气氧化性构成和演变特征、一次污染物大气氧化产生二次污染的化学反应机制、识别影响大气氧化进程的关键化学和物理要素等研究. 承担和参与多项国家自然科学基金委项目和国家重点研发计划项目.

陆思华, 北京大学环境科学与工程学院, 教授级高工. 主要研究方向为区域大气有机污染物的来源、转化、环境影响等. 研究工作主要包括: 城市和区域大气VOCs的组成特征及环境影响、VOCs重点行业污染源排放特征及污染来源解析、大气中VOCs和SVOCs分析测试技术及质控等. 近年来, 作为课题负责人或课题骨干, 负责和参加了大气重污染成因与治理公关项目、科技部大气重点研发计划、国家环保公益性行业科研专项及横向协作等多项科研工作.

基金资助:
国家自然科学基金(91844301); 国家自然科学基金(91644108)

Advances on Atmospheric Oxidation Mechanism of Typical Aromatic Hydrocarbons

Mengdi Song, Ying Liu, Xin Li(), Sihua Lu

State Key Joint Laboratory of Environmental Simulation and Pollution Control, International Joint Laboratory for Regional Pollution Control, Ministry of Education (IJRC), College of Environmental Sciences and Engineering, Peking University, Beijing 100871, China

Received:2021-05-20 Published:2021-08-02
Contact: Xin Li
Supported by:
National Natural Science Foundation of China(91844301); National Natural Science Foundation of China(91644108)

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摘要/Abstract

芳香烃作为城市大气臭氧(O₃)和二次有机气溶胶(SOA)的重要前体物, 由于其对大气二次污染、气候变化及人体健康具有重要影响, 因此芳香烃氧化机理研究成为当前大气环境化学领域最具挑战的热点研究之一. 本文综述了芳香烃氧化机理的研究成果, 详细讨论了它们与OH自由基在高低氮氧化物条件下的各反应通道和影响因素, 重点关注近年来芳香烃氧化反应研究中的新发现和新理论. 芳香烃的大气氧化反应起始由OH自由基主导, 根据其反应产物主要分为醛通道、酚通道、双环RO₂通道和环氧化物通道. 随着形成多羟基化合物、烷氧自由基环氧化、双环过氧自由基分子内氢转移、醛类化合物氢转移、CO-loss生成低碳产物等新理论的提出, 对芳香烃氧化的理解虽然有所提高, 但反应过程仍存在碳质量不守恒和自由基不闭合的问题, 导致对后续O₃和SOA形成机制的认识还十分有限. 理论计算和实验室模拟是目前芳香烃氧化机理研究的主要手段. 质谱法和光谱法是芳香烃氧化产物最常用的测量技术, 在线质谱技术尝试从分子水平上捕捉示踪性中间产物的转化, 对揭示芳烃氧化机理具有重要作用. 随着示踪物测量技术的发展, 特别是色谱-质谱联用技术为中间产物的精准测量和芳香烃氧化机制的完善开拓了新方向. 在此基础上, 厘清芳烃氧化中的碳平衡和自由基收支等关键科学问题、探究实际大气中芳香烃的环境效应有望成为未来该领域的重点研究方向.

关键词: 芳香烃, 醛途径, 酚途径, 双环RO₂途径, 氢转移反应

Aromatic hydrocarbons are important precursors of ozone and secondary organic aerosols in the urban atmosphere, which have important impact on air pollution, climate change and human health. Thus the research on the oxidation mechanism of aromatic hydrocarbons has become one of the most challenging hotspots topics in atmospheric environmental chemistry. This paper reviews the recent studies of aromatic hydrocarbons oxidation mechanism, discusses the reaction channels and influencing factors during the oxidation process under high/low NO_x conditions, and focuses on new discoveries and new theories in the studies of aromatic hydrocarbon oxidation reactions. In the atmosphere, the initiation of aromatic hydrocarbons is dominated by the reaction with the OH radicals. According to the different reaction products, the oxidation reaction of aromatic hydrocarbon is mainly divided into aldehyde pathway, phenolic pathway, bicyclic RO₂ pathway and epoxide pathway. With the development of new theories such as the formation of polyhydroxy compounds by aldehyde pathway, alkoxy radical epoxidation reaction, intramolecular H-migration reaction of bicyclic peroxy radicals, 1,5-aldehydic H-shift reaction, and the generation of low-carbon products by CO-loss reaction, the understanding of aromatic hydrocarbons oxidation mechanisms has improved. However, due to the carbon missing and radical budgets imbalance problems in the existing oxidation mechanism, our understanding about the subsequent O₃ and secondary organic aerosols formation mechanisms are very limited. Theoretical calculation and experiment are the main methods to study the oxidation mechanism of aromatic hydrocarbons. Mass spectrometry and spectroscopy are the dominant measurement techniques for the oxidation intermediates of aromatic hydrocarbons. Online mass spectrometry can capture the tracer intermediates at the molecular level, which plays an important role in revealing the oxidation mechanism of aromatic hydrocarbons. In recent years, tracer measurement technology, especially chromatography-mass spectrometry technology has developed rapidly. This open up a new direction for the accurate measurement of intermediates and the improvement of aromatic hydrocarbon oxidation mechanism. On this basis, improving aromatic hydrocarbons oxidation mechanism, paying attention to the carbon missing and radical budgets imbalance in the oxidation reaction, and exploring the environmental implication of aromatic hydrocarbons oxidation in the real atmospheric conditions are expected to become the important directions of aromatic hydrocarbon oxidation study in the future.

Key words: aromatic hydrocarbon, aldehyde pathway, phenolic pathway, bicyclic RO₂ pathway, H-migration

引用此文

宋梦迪, 刘莹, 李歆, 陆思华. 典型芳香烃大气氧化机理研究进展[J]. 化学学报, 2021, 79(10): 1214-1231.

Mengdi Song, Ying Liu, Xin Li, Sihua Lu. Advances on Atmospheric Oxidation Mechanism of Typical Aromatic Hydrocarbons[J]. Acta Chimica Sinica, 2021, 79(10): 1214-1231.

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图/表 18

图1. 典型芳香烃氧化对空气质量、人体健康和气候的影响, abs代表摘取反应, add代表加成反应, HOMs代表高含氧有机化合物; GYL代表乙二醛; MGYL代表甲基乙二醛; NPF代表新粒子生成; CCN代表云凝结核; BrC代表棕色碳

Figure 1. Effects of typical aromatic hydrocarbon oxidation on air quality, climate change and human health. abs: abstraction reaction; add: addition reaction; HOMs: highly oxygenated organic molecules; GYL: glyoxal; MGYL: methylglyoxal; NPF: new particle formation; CCN: cloud condensation nuclei; BrC: brown carbon

图2. 不同研究中甲苯氧化产物产率汇总[25,30⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-50], 实心柱代表有NOx参与的甲苯氧化产物产率研究, 斜线柱代表没有NOx参与的甲苯氧化产物产率研究

Figure 2. Summary of yields of toluene oxidation products in different studies[25,30⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-50]. The solid box represents the product yield study with NOx participation, while the slash box represents the product yield study without NOx participation

Species	Reaction with OH	Reaction with NO₃	Reaction with O₃
Species	×10^-12(cm³• molecule^-1•s^-1)	×10^-15(cm³• molecule^-1•s^-1)	×10^-20(cm³• molecule^-1•s^-1)
Benzene	1.22	<0.03
Toluene	5.63	0.07	<1
Ethylbenzene	7	<0.6
o-Xylene	13.6	0.41
m-Xylene	23.1	0.26
p-Xylene	14.3	0.5
1,2,3-TMB^a	32.7	1.9
1,2,4- TMB^a	32.5	1.8
1,3,5- TMB^a	56.7	8.8

表1. 常见芳香烃化合物与OH, NO3和O3自由基的反应速率[4,59,64]

Table 1. The reaction rate of aromatic hydrocarbon compounds with OH, NO3 and O3 radicals[4,59,64]

图式1. 甲苯的OH引发反应, abs代表摘取反应, add代表加成反应

Scheme 1. OH-Initiated oxidation reaction of toluene. abs: abstraction, add: addition

图3. 理论计算研究中芳香烃OH引发各反应位点产物产率[38,57,62,66,69⇓-71]

Figure 3. In the theoretical calculation study, literature yield of products initiated by OH-initiated oxidation reaction of aromatic hydrocarbon[38,57,62,66,69⇓-71]

图式2. 芳香烃大气氧化主要反应途径(以甲苯为例), T代表甲苯, Me代表甲基, yl代表碳基自由基, B代表双环化合物, Tri代表三环化合物, C代表羟基环己烷/羟基环己烯或羟基环己二烯, P代表过氧桥, E代表环氧桥, O代表烷氧自由基, OO代表过氧自由基

Scheme 2. The main reaction pathway of aromatic hydrocarbon oxidation (taking toluene as an example). T: Toluene, Me: Methyl, yl: Carbon-based radical, B: bicyclic compound, Tri: tricyclic compound, C: hydroxy cyclohexane/hydroxyl cyclohexene or hydroxyl cyclohexadiene, P: peroxide bridge, E: epoxide bridge, O: alkoxy radical, OO: peroxy radical

图式3. 甲酚在高低NOx条件下与OH自由基反应机理[29]. MCM机制中包含的反应用黑色表示, Schwantes等[29]提出的反应用蓝色表示, 高NOx条件下发生的反应用粉红色框框出, 低NOx条件下发生的反应用蓝色框框出

Scheme 3. Reaction mechanism of cresol with OH radical under high and low NOx conditions[29]. Reactions that have been included in the MCM mechanism are shown in black, reactions that proposed by Schwantes et al.[29] are shown in blue, reactions that occur under high NOx conditions are shown in pink box, and reactions that occur under low NOx conditions are shown in blue box

图式4. 双环RO2环聚反应形成三环过氧桥烷基自由基流程图

Scheme 4. Tricyclic peroxy bridge carbon-based radical formed by bicyclic RO2 cyclic polymerization reaction

图式5. TriCPE-yl自由基与O2的加成反应

Scheme 5. The addition reaction of TriCPE-yl radical with O2

图式6. RO2与NO, HO2和RO2的双分子反应. Rnitrate代表RO2与NO反应生成的有机硝酸酯产物通道的分支比. 图式6中各反应的分支比参照了Jenkin等[88]的研究

Scheme 6. Bimolecular reactions of RO2 with NO, HO2 and RO2. Rnitrate represent the bifurcation ratio of organic nitrate product channels produced by reaction of RO2 with NO. The branching ratio of each reaction in Scheme 6 refers to the study by Jenkin et al.[88]

图式7. 芳香烃氧化中间产物烷氧自由基环氧化反应

Scheme 7. Aromatic hydrocarbon oxidation intermediate product alkoxy radical epoxidation reaction

图式8. 芳香烃氧化过程环氧化物形成过程[23,58]

Scheme 8. Fates of epoxides formation during aromatic hydrocarbon oxidation mechanism[23,58]

图式9. 芳香烃氧化过程RO的开环反应. 机制(a)参考MCM (http://mcm.leeds.ac.uk/MCM-devel/roots.htt), 机制(b)参考Wu等[62]的研究, 机制(c)参考Wang等[28]和Xu等[27]的研究

Scheme 9. RO ring open reactions during aromatic hydrocarbon oxidation mechanism. Mechanism (a) was refer to MCM (http://mcm.leeds.ac.uk/MCM-devel/roots.htt). Mechanism (b) refers to the research of Wu et al.[62]. Mechanism (c) refers to the research of Wang et al.[28] and Xu et al.[27]

图式10. 芳香烃氧化过程中RO2的H转移反应

Scheme 10. RO2 H-Migrations reaction during aromatic hydrocarbon oxidation mechanism

图式11. 芳香烃氧化过程中醛类化合物H转移反应[27]

Scheme 11. Aldehydic H-shift reactions during aromatic hydrocarbon oxidation mechanism[27]

图4. 近20年芳香烃氧化机理研究发展历程图[13,24,26⇓⇓-29,34,37-38,51,60,62,73,82,118,130,133⇓⇓⇓⇓-138]. 图中的年份代表了参考文献的发布年份

Figure 4. Development of researches on oxidation mechanism of aromatic hydrocarbons in recent 20 years[13,24,26⇓⇓-29,34,37-38,51,60,62,73,82,118,130,133⇓⇓⇓⇓-138]. The year in the figure represents the references' publish year

图5. 芳香烃氧化主要中间产物及自由基的常用测量方法[26-27,29,45,147⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-168]. 图中的化合物分子式仅为每类中间氧化产物的代表. PTR代表质子转移反应质谱, CIMS代表化学电离质谱, DOAS代表差分光学吸收光谱, CRDS代表腔衰荡光谱, CEAS代表腔增强吸收光谱, FTIR代表傅里叶变换红外光谱, LIF代表激光诱导荧光技术

Figure 5. Common measure methods of the main aromatic hydrocarbon oxidation intermediate product and radicals[26-27,29,45,147⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-168]. The compounds in the figure are examples of each type of intermediate oxidation product. PTR: proton-transfer-reaction mass spectrometry, CIMS: chemical ionization mass spectrometer, DOAS: differential optical absorption spectroscopy, CRDS: cavity ring down spectroscopy, CEAS: cavity enhanced absorption spectroscopy, FTIR: Fourier transform infrared, LIF: laser-induced fluorescence

图6. 理论计算和实验室研究中芳香烃氧化主要氧化途径占比及中间产物产率汇总[24-25,27,30⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-41,44⇓⇓⇓-48,50,62,119,133,135]. ETHBEN代表乙苯, a代表MCM机制的结果(http://mcm.york.ac.uk/), b代表Birdsall和Elrod等[34]的研究结果, c代表Wang等[24]的研究结果, d代表Xu等[27]的研究结果, e代表Wu 等[62]的研究结果, f代表Ji等[38]的研究结果, g代表Li和Wang等[133]的研究结果

Figure 6. Summary of the proportion of the main oxidation pathways of aromatic hydrocarbons and the yield of intermediate products in theoretical calculation and laboratory research[24-25,27,30⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-41,44⇓⇓⇓-48,50,62,119,133,135]. ETHBEN: ethyl benzene, a represent the result of MCM mechanism (http://mcm.york.ac.uk/), b represent the study of Birdsall and Elrod[34], c represent the study of Wang et al.[24], d represent the study of Xu et al. [27], e represent the study of Wu et al.[62], f represent the study of Ji et al.[38], g represent the study of Li and Wang[133]

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典型芳香烃大气氧化机理研究进展

Advances on Atmospheric Oxidation Mechanism of Typical Aromatic Hydrocarbons

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