Mechanism of Formation of Volatile Organic Compounds from Oxidation of Linseed Oil

被引:18
作者
Juita [1 ]
Dlugogorski, Bogdan Z. [1 ]
Kennedy, Eric M. [1 ]
Mackie, John C. [1 ]
机构
[1] Univ Newcastle, Sch Engn, Proc Safety & Environm Protect Grp, Callaghan, NSW 2308, Australia
基金
澳大利亚研究理事会;
关键词
BUILDING PRODUCTS; EMISSIONS; CHEMISTRY; SYSTEMS;
D O I
10.1021/ie202536n
中图分类号
TQ [化学工业];
学科分类号
0817 ;
摘要
The pathways of volatile organic compound (VOC) formation have been investigated through a computational study, employing the Gaussian 03 suite of programs. We optimized geometries and zero-point vibrational energies (ZPVEs) at the B3LYP/6-31G(d) level of theory and improved electronic energies by conducting single-point energy calculations using the large 6-311++G(3df,3pd) basis set. To describe the predominant mechanism of the linseed oil oxidation, the following sequence is proposed: hydrogen abstraction of unsaturated fatty compounds as the initiation reaction followed by the reaction of allylic-type radicals with molecular oxygen to form peroxyl radicals and finally intramolecular rearrangement through four- and five-membered rings. Quantum calculations identified low-energy pathways following cyclization resulting in the formation of major products observed, especially aldehydes and ketones. The overall energy changes taking place through the four- and five-membered rings were found to be 78 and 93 kJ mol(-1) exothermic, respectively. Metal catalysts decompose hydroperoxides based on the Fenton-like mechanism into alkoxyl and peroxyl radicals.
引用
收藏
页码:5653 / 5661
页数:9
相关论文
共 50 条
[41]   Air quality impacts from the development of unconventional oil and gas well pads: Air toxics and other volatile organic compounds [J].
Ku, I-Ting ;
Zhou, Yong ;
Hecobian, Arsineh ;
Benedict, Katherine ;
Buck, Brent ;
Lachenmayer, Emily ;
Terry, Bryan ;
Frazier, Morgan ;
Zhang, Jie ;
Pan, Da ;
Low, Lena ;
Sullivan, Amy ;
Collett Jr, Jeffrey L. .
ATMOSPHERIC ENVIRONMENT, 2024, 317
[42]   Volatile organic compounds from leaf litter decomposition alter soil microbial communities and carbon dynamics [J].
McBride, Steven G. ;
Choudoir, Mallory ;
Fierer, Noah ;
Strickland, Michael S. .
ECOLOGY, 2020, 101 (10)
[43]   Positive feedback mechanism between biogenic volatile organic compounds and the methane lifetime in future climates [J].
Boy, Michael ;
Zhou, Putian ;
Kurten, Theo ;
Chen, Dean ;
Xavier, Carlton ;
Clusius, Petri ;
Roldin, Pontus ;
Baykara, Metin ;
Pichelstorfer, Lukas ;
Foreback, Benjamin ;
Back, Jaana ;
Petaja, Tuukka ;
Makkonen, Risto ;
Kerminen, Veli-Matti ;
Pihlatie, Mari ;
Aalto, Juho ;
Kulmala, Markku .
NPJ CLIMATE AND ATMOSPHERIC SCIENCE, 2022, 5 (01)
[44]   Diurnal and seasonal variation of volatile organic compounds in the atmosphere of Monterrey, Mexico [J].
Lizette Menchaca-Torre, H. ;
Mercado-Hernandez, Roberto ;
Mendoza-Dominguez, Alberto .
ATMOSPHERIC POLLUTION RESEARCH, 2015, 6 (06) :1073-1081
[45]   Characteristics of carbonyls and volatile organic compounds (VOCs) in residences in Beijing, China [J].
Duan, Hengyi ;
Liu, Xiaotu ;
Yan, Meilin ;
Wu, Yatao ;
Liu, Zhaorong .
FRONTIERS OF ENVIRONMENTAL SCIENCE & ENGINEERING, 2016, 10 (01) :73-84
[46]   Catalytic ozonation of volatile organic compounds (ethyl acetate) at normal temperature [J].
Cui, Jiahao ;
Liu, Shejiang ;
Xue, Hua ;
Wang, Xianqin ;
Hao, Ziquan ;
Liu, Rui ;
Shang, Wei ;
Zhao, Dan ;
Ding, Hui .
CHINESE JOURNAL OF CHEMICAL ENGINEERING, 2021, 32 :159-167
[47]   Very volatile organic compounds: an understudied class of indoor air pollutants [J].
Salthammer, T. .
INDOOR AIR, 2016, 26 (01) :25-38
[48]   Volatile organic compounds and their contribution to ground-level ozone formation in a tropical urban environment [J].
Zulkifli, Mohd Faizul Hilmi ;
Hawari, Nor Syamimi Sufiera Limi ;
Latif, Mohd Talib ;
Abd Hamid, Haris Hafizal ;
Mohtar, Anis Asma Ahmad ;
Idris, Wan Mohd Razi Wan ;
Mustaffa, Nur Ili Hamizah ;
Juneng, Liew .
CHEMOSPHERE, 2022, 302
[49]   Nocturnal atmospheric synergistic oxidation reduces the formation of low-volatility organic compounds from biogenic emissions [J].
Zang, Han ;
Luo, Zekun ;
Li, Chenxi ;
Li, Ziyue ;
Huang, Dandan ;
Zhao, Yue .
ATMOSPHERIC CHEMISTRY AND PHYSICS, 2024, 24 (20) :11701-11716
[50]   A Study on the Ozone Formation Potential of Volatile Organic Compounds in Busan using SIFT-MS [J].
Hwang, Kyucheol ;
An, Joon Geon ;
Lee, Seonghyun ;
Choi, Wonsik ;
Yim, Un Hyuk .
JOURNAL OF KOREAN SOCIETY FOR ATMOSPHERIC ENVIRONMENT, 2020, 36 (05) :645-668