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OH-Initiated Oxidation of Acetylacetone: Implications For Article Cite This: Environ. Sci. Technol. 2018, 52, 11169−11177 pubs.acs.org/est OH-Initiated Oxidation of Acetylacetone: Implications for Ozone and Secondary Organic Aerosol Formation † ∥ ‡ ∥ † § † † † Yuemeng Ji, , Jun Zheng, , Dandan Qin, Yixin Li, Yanpeng Gao, Meijing Yao, Xingyu Chen, † † § Guiying Li, Taicheng An,*, and Renyi Zhang*, † Guangzhou Key Laboratory of Environmental Catalysis and Pollution Control, School of Environmental Science and Engineering, Institute of Environmental Health and Pollution Control, Guangdong University of Technology, Guangzhou 510006, P. R. China ‡ Collaborative Innovation Center of Atmospheric Environment and Equipment Technology, Nanjing University of Information Science & Technology, Nanjing 210044, P. R. China § Department of Atmospheric Sciences and Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States *S Supporting Information ABSTRACT: Acetylacetone (AcAc) is a common atmos- pheric oxygenated volatile organic compound due to broad industrial applications, but its atmospheric oxidation mecha- nism is not fully understood. We investigate the mechanism, kinetics, and atmospheric fate of the OH-initiated oxidation for the enolic and ketonic isomers of AcAc using quantum chemical and kinetic rate calculations. OH addition to enol- AcAc is more favorable than addition to keto-AcAc, with the total rate constant of 1.69 × 10−13 exp(1935/T) cm3 molecule−1 s−1 over the temperature range of 200−310 K. For the reaction of the enol-AcAc with OH, the activation energies of H-abstraction are at least 4 kcal mol−1 higher than those of OH-addition, and the rate constants for OH-addition are by 2−3 orders of magnitude higher than those for H-abstraction. Oxidation of AcAc is predicted to yield significant amounts of acetic acid and methylglyoxal, larger than those are currently recognized. A lifetime of less than a few hours for AcAc is estimated throughout the tropospheric conditions. In addition, we present field measurements in Beijing and Nanjing, China, showing significant concentrations of AcAc in the two urban locations. Our results reveal that the OH-initiated oxidation of AcAc contributes importantly to ozone and SOA formation under polluted environments. ■ INTRODUCTION Furthermore, emissions of AcAc in developing countries (such as China) are anticipated to be substantially increased because Ketones represent an important class of oxygenated volatile 14,15 organic compounds (OVOCs) and are emitted from natural of their rapid industrialization and economic development. AcAc is a prototype of β-diketone that exists in the two See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles. and anthropogenic sources, e.g., from industrial activities and Downloaded via GUANGDONG UNIV OF TECHNOLOGY on October 17, 2018 at 07:18:05 (UTC). oxidation reactions of both biogenic and anthropogenic tautomeric forms: the enol form contains an intramolecular − hydrocarbons.1 5 The atmospheric oxidation of ketones has hydrogen bond and resonance stabilization through a fi conjugated π-system, whereas the diketo form contains two been identi ed as important sources for HOx radical species 6,7 6,8 carbonyl groups with an ∼140° dihedral angle between the (i.e., OH and HO2) and secondary organic aerosol (SOA), profoundly impacting air quality, human health, and climate. oxygens. The atmospheric oxidation mechanism of AcAc is Acetylacetone (also known as 2,4-pentanedione or AcAc) is complex, including multiple pathways and steps. Oxidation of 13,16−18 highly reactive and broadly used for various industrial AcAc is mainly initiated by the hydroxyl radical (OH). applications. For example, AcAc is an important reagent in An earlier experimental study by Zhou et al. has evaluated the preparation of chelate compounds for a wide range of atmospheric chemistry for AcAc; using a relative kinetic transition metals,9,10 an industrial additive,11 and a building method the authors determined the temperature dependent block for synthesis of heterocyclic compounds and raw rate coefficients over the temperature range of 285−310 K, materials for sulfonamide drugs.12 In developed countries such as Japan, the United States, and Europe, the global Received: July 18, 2018 capacity of AcAc is estimated to be approximately 20 000 t Revised: August 13, 2018 − a 1,13 mainly from industrial activities, while its formation from Accepted: August 30, 2018 in situ atmospheric photochemical production is negligible. Published: August 30, 2018 © 2018 American Chemical Society 11169 DOI: 10.1021/acs.est.8b03972 Environ. Sci. Technol. 2018, 52, 11169−11177 Environmental Science & Technology Article Figure 1. Optimized geometries of the key stationary points of OH-AcAc reaction at the M06-2X/6-311G(d,p). The bond length is in Å. − with an Arrhenius expression of k = 3.35 × 10−12 exp[(983 ± has been demonstrated.33 36 Furthermore, no theoretical 130)/T] cm3 molecule−1 s−1.13 That experimental work also results are available on the atmospheric chemistry of AcAc. identified several products from the OH-initiated oxidation of In this work, we have investigated the detailed oxidation AcAc, including methylglyoxal (MG), acetic acid (AA), and mechanism of AcAc with OH employing quantum chemical peroxyacethyl nitrate (PAN).13 On the basis of their measured and kinetic rate calculations within the tropospheric temper- products, a mechanism for the reaction of AcAc with OH has ature range of 200−310 K. We also present field measurements been postulated, involving the initial OH addition to C2 and of AcAc in Nanjing and Beijing, China using proton-transfer 13 C3 positions followed by O2 addition. reaction mass spectrometry (PTR-MS). The atmospheric fate In contrast to investigation on the industrial applications of and oxidation products of AcAc are assessed, and the − AcAc,9 12 limited previous work exists on the atmospheric implications of our results for ozone and SOA formation are oxidation mechanism of AcAc, hindering accurate assessment discussed. of its roles in the formation of ozone and fine particulate matter (PM). For example, MG, organic acids, and PAN have ■ METHODS been identified as the critical species leading to SOA 14,15,19−24 fi The electronic structures and energy calculations were carried formation. Speci cally, organic acids play important out with the Gaussian 09 program suite.37 Geometrical 25,26 − roles in new particle formation and growth and acid base optimization of all stationary points (SPs), such as the 27,28 α reactions, while oligomerization of small -dicarbonyls reactants, transition states (TSs), complexes, intermediates, represents a major source of SOA on the urban, regional, and and products, was performed using the M06-2X level with the 29,30 α global scales. The atmospheric sources of small - 6-311G(d,p) basis set denoted as the M06-2X/6-311G(d,p) dicarbonyls, organic acids, and PAN, however, remain poorly level. The M06-2X functional is a high-nonlocality functional fi 14 quanti ed. The current atmospheric chemical mechanism for with double the amount of nonlocal exchange (2X), with the AcAc oxidation has been proposed on the basis of the reliable performance for the thermochemistry, hydrogen 13 environmental chamber experiment, which has provided bonding, kinetics, and weak interactions.38 In addition, the critical information on the initial kinetic and products of the MPWB1K/, B3LYP/, MP2/and QCISD/6-311G(d,p) levels AcAc oxidation. However, extrapolation of the kinetics and were also employed to optimize the geometry and to validate mechanism of the AcAc reactions from the measured product the convergence of the predicted geometries. The MPWB1K yields is challenging, since a product formation typically and B3LPY methods and the MP2 method represent the involves multiple possible steps and pathways and the product classic density functional theory and the classic Ab Initio is subject to secondary reactions or photolysis. In addition, theory, respectively, while the QCISD method corresponds to there exist additional intricate difficulties using the chamber a higher electronic correlation method. Frequency calculations method. Noticeably, the limitations of the chamber method were carried out at the M06-2X/6-311G(d,p) level to include a long reaction time, higher reactant concentrations, determine all SPs as a real local minima (without any and wall loss.31,32 In particular, the significance of wall loss for imaginary frequency) or a TS (with only one imaginary reactive and condensable species using the chamber method frequency). The evaluation of the vibrational frequencies 11170 DOI: 10.1021/acs.est.8b03972 Environ. Sci. Technol. 2018, 52, 11169−11177 Environmental Science & Technology Article Figure 2. PES for the OH-initiated reactions of keto- and enol-AcAc (in the unit of kcal mol−1). confirmed that all optimized geometries represented the campus of Nanjing University of Information Science & minima on the potential energy surfaces (Table S1 of the Technology (NUIST) in Nanjing and on the campus of Supporting Information, SI). Intrinsic reaction coordinate Tsinghua University in Beijing. (IRC) calculations were performed to confirm the connection between the TSs and their corresponding reactants and ■ RESULTS AND DISCUSSION 7,39 products. The potential energy surface (PES) was further Initial Reaction of AcAc with OH. There exists an fi re ned by the M06-2X/6-311++G(3df,3pd) level to yield equilibrium between enolipc and ketonic isomers of AcAc
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