Advertisement

Mechanisms of Xylene Isomer Oxidation by Non-thermal Plasma via Paired Experiments and Simulations

  • Tianyu Shou
  • Nan Xu
  • Yihan Li
  • Guojin Sun
  • Matthew T. Bernards
  • Yao Shi
  • Yi HeEmail author
Original Paper
  • 24 Downloads

Abstract

Xylene is a widely used solvent and industrial chemical, but it is also considered to be a volatile organic compound (VOC) pollutant. Meanwhile, non-thermal plasma (NTP) is a potential method for remediating VOC contaminants, especially aromatic hydrocarbons. During NTP degradation of xylene, the different oxidation mechanisms of three isomers, p-xylene, o-xylene and m-xylene, have attracted lots of attention but not been studied at the molecular level. In this study, the individual degradation rates of xylene isomers in a NTP system are measured. The results show the oxidation degradation rates have the following order: o-xylene > p-xylene ≈ m-xylene. Molecular dynamics simulations with an applied external electric field were adopted to examine the oxidation process of xylene isomers, as well. The oxidation rates from the simulations were calculated, the order of which is in a good agreement with the experimental results. The oxidation pathways of xylene isomers were analyzed more thoroughly to explain the rate differences. The external electrical field is found to have two effects: one is to speed up the oxidation rate of xylene isomers overall, and the other is to alter the oxidation pathways to increase the probability of the faster ring cleavage pathways of o-xylene.

Keywords

Xylene isomers Non-thermal plasma MD simulation Oxidation pathway 

Notes

Acknowledgements

The authors would like to thank the National Key Research and Development Program of China (Grant No. 2018YFC0213806) and the National Natural Science Foundation of China (Grant Nos. 21676245 and 51750110495) for financial support.

Compliance with Ethical Standards

Conflict of interest

There are no conflicts of interest to declare.

Supplementary material

11090_2019_9986_MOESM1_ESM.doc (875 kb)
Supplementary material 1 (DOC 874 kb)

References

  1. 1.
    Niu H, Mo ZW, Shao M, Lu SH, Xie SD (2016) Screening the emission sources of volatile organic compounds (VOCs) in China by multi-effects evaluation. Front Environ Sci Eng 10(5):11.  https://doi.org/10.1007/s11783-016-0828-z Google Scholar
  2. 2.
    Jeong E, Hirai M, Shoda M (2008) Removal of o-xylene using biofilter inoculated with Rhodococcus sp BTO62. J Hazard Mater 152(1):140–147.  https://doi.org/10.1016/j.jhazmat.2007.06.078 Google Scholar
  3. 3.
    ATSDR (1995) Toxicological profile for xylenes. Public Health Service, U.S. Department of Health and Human Services, AtlantaGoogle Scholar
  4. 4.
    Richter D, Thielert H, Wozny G (2008) Absorption of aromatic hydrocarbons in multicomponent mixtures: A comparison between simulations and measurements in a pilot plant. In: Braunschweig B, Joulia X (eds) 18th European symposium on computer aided process engineering, vol 25. Computer Aided Chemical Engineering. Elsevier Science Bv, Amsterdam, pp 799–804Google Scholar
  5. 5.
    Kim HJ, Pant HR, Choi NJ, Kim CS (2013) Composite electrospun fly ash/polyurethane fibers for absorption of volatile organic compounds from air. Chem Eng J 230:244–250.  https://doi.org/10.1016/j.cej.2013.06.090 Google Scholar
  6. 6.
    Yang K, Sun Q, Xue F, Lin DH (2011) Adsorption of volatile organic compounds by metal-organic frameworks MIL-101: influence of molecular size and shape. J Hazard Mater 195:124–131.  https://doi.org/10.1016/j.jhazmat.2011.08.020 Google Scholar
  7. 7.
    Kim SC (2002) The catalytic oxidation of aromatic hydrocarbons over supported metal oxide. J Hazard Mater 91(1–3):285–299.  https://doi.org/10.1016/s0304-3894(01)00396-x Google Scholar
  8. 8.
    Qi B, Moe WM (2006) Performance of low pH biofilters treating a paint solvent mixture: continuous and intermittent loading. J Hazard Mater 135(1–3):303–310.  https://doi.org/10.1016/j.jhazmat.2005.11.065 Google Scholar
  9. 9.
    Chen HL, Lee HM, Chen SH, Chang MB, Yu SJ, Li SN (2009) Removal of volatile organic compounds by single-stage and two-stage plasma catalysis systems: a review of the performance enhancement mechanisms, current status, and suitable applications. Environ Sci Technol 43(7):2216–2227.  https://doi.org/10.1021/es802679b Google Scholar
  10. 10.
    Yi HH, Yang X, Tang XL, Zhao SZ, Huang YH, Cui XX, Feng TC, Ma YQ (2018) Removal of toluene from industrial gas by adsorption-plasma catalytic process: comparison of closed discharge and ventilated discharge. Plasma Chem Plasma Process 38(2):331–345.  https://doi.org/10.1007/s11090-017-9863-1 Google Scholar
  11. 11.
    Ma TP, Jiang HD, Liu JQ, Zhong FC (2016) Decomposition of benzene using a pulse-modulated DBD plasma. Plasma Chem Plasma Process 36(6):1533–1543.  https://doi.org/10.1007/s11090-016-9736-z Google Scholar
  12. 12.
    Wang L, He H, Zhang CB, Wang YF, Zhang B (2016) Effects of precursors for manganese-loaded gamma-Al2O3 catalysts on plasma-catalytic removal of o-xylene. Chem Eng J 288:406–413.  https://doi.org/10.1016/j.cej.2015.12.023 Google Scholar
  13. 13.
    Wang L, Zhang CB, He H, Liu FD, Wang CX (2016) Effect of doping metals on OMS-2/γ-Al2O3 catalysts for plasma-catalytic removal of o-xylene. J Phys Chem C 120(11):6136–6144.  https://doi.org/10.1021/acs.jpcc.6b00870 Google Scholar
  14. 14.
    Lee HM, Chang MB (2003) Abatement of gas-phase p-xylene via dielectric barrier discharges. Plasma Chem Plasma Process 23(3):541–558.  https://doi.org/10.1023/a:1023239122885 Google Scholar
  15. 15.
    Sudhakaran MSP, Trinh HQ, Karuppiah J, Hossian MM, Mok YS (2017) Plasma catalytic removal of p-xylene from air stream using gamma-Al2O3 supported manganese catalyst. Top Catal 60(12–14):944–954.  https://doi.org/10.1007/s11244-017-0759-3 Google Scholar
  16. 16.
    Ye ZP, Wang CX, Shao ZH, Ye Q, He Y, Shi Y (2012) A novel dielectric barrier discharge reactor with photocatalytic electrode based on sintered metal fibers for abatement of xylene. J Hazard Mater 241:216–223.  https://doi.org/10.1016/j.jhazmat.2012.09.033 Google Scholar
  17. 17.
    Wei BL, Chen YP, Ye MJ, Shao ZH, He Y, Shi Y (2015) Enhanced degradation of gaseous xylene using surface acidized TiO2 catalyst with non-thermal plasmas. Plasma Chem Plasma Process 35(1):173–186.  https://doi.org/10.1007/s11090-014-9571-z Google Scholar
  18. 18.
    Shi Y, Shao ZH, Shou TY, Tian RB, Jiang JQ, He Y (2016) Abatement of gaseous xylene using double dielectric barrier discharge plasma with in situ UV light: operating parameters and byproduct analysis. Plasma Chem Plasma Process 36(6):1501–1515.  https://doi.org/10.1007/s11090-016-9741-2 Google Scholar
  19. 19.
    Kuroki T, Hirai K, Kawabata R, Okubo M, Yamamoto T, Ieee (2008) Decomposition of adsorbed xylene on adsorbent using nonthermal plasma and gas circulation. In: 2008 Ieee industry applications society annual meeting, vols 1–5. IEEE Industry Applications Society Annual Meeting. Ieee, New York, pp 403Google Scholar
  20. 20.
    Duin ACTV, Dasgupta S, Lorant F, Goddard WA (2001) ReaxFF: a reactive force field for hydrocarbons. J Phys Chem A 105(41):9396–9409Google Scholar
  21. 21.
    Chenoweth K, van Duin AC, Dasgupta S, Rd GW (2009) Initiation mechanisms and kinetics of pyrolysis and combustion of JP-10 hydrocarbon jet fuel. J Phys Chem A 113(9):1740–1746Google Scholar
  22. 22.
    Chenoweth K, Duin ACTV, Goddard WA (2008) ReaxFF reactive force field for molecular dynamics simulations of hydrocarbon oxidation. J Phys Chem A 112(5):1040Google Scholar
  23. 23.
    Hamaguchi S, Yamashiro M, Yamada H (2007) Atomic-level simulation of non-equilibrium surface chemical reactions under plasma–wall interaction. Comput Phys Commun 177(1–2):108–109.  https://doi.org/10.1016/j.cpc.2007.02.068 Google Scholar
  24. 24.
    Tan S, Xia T, Shi Y, Pfaendtner J, Zhao S, He Y (2017) Enhancing the oxidation of toluene with external electric fields: a reactive molecular dynamics study. Sci Rep 7(1):1710Google Scholar
  25. 25.
    Aktulga HM, Fogarty JC, Pandit SA, Grama AY (2012) Parallel reactive molecular dynamics: numerical methods and algorithmic techniques. Parallel Comput 38(4–5):245–259Google Scholar
  26. 26.
    Rappe AK, Iii WAG (1991) Charge equilibration for molecular dynamics simulations. J Phys Chem 95(8):3358–3363Google Scholar
  27. 27.
    Martínez L, Andrade R, Birgin EG, Martínez JM (2009) PACKMOL: a package for building initial configurations for molecular dynamics simulations. J Comput Chem 30(13):2157–2164Google Scholar
  28. 28.
    Humphrey W, Dalke A, Schulten K (1996) VMD: visual molecular dynamics. J Mol Graph 14(1):33–38Google Scholar
  29. 29.
    Berendsen HJC, Postma JPM, Gunsteren WFV, Dinola A, Haak JR (1984) Molecular dynamics with coupling to an external bath. J Chem Phys 81(8):3684–3690Google Scholar
  30. 30.
    Cheng XM, Wang QD, Li JQ, Wang JB, Li XY (2012) ReaxFF molecular dynamics simulations of oxidation of toluene at high temperatures. J Phys Chem A 116(40):9811–9818.  https://doi.org/10.1021/jp304040q Google Scholar
  31. 31.
    Gail S, Dagaut P (2005) Experimental kinetic study of the oxidation of p-xylene in a JSR and comprehensive detailed chemical kinetic modeling. Combust Flame 141(3):281–297.  https://doi.org/10.1016/j.combustflame.2004.12.020 Google Scholar
  32. 32.
    Gail S, Dagaut P (2007) Oxidation of m-xylene in a JSR: experimental study and detailed chemical kinetic modeling. Combust Sci Technol 179(5):813–844.  https://doi.org/10.1080/00102200600671989 Google Scholar
  33. 33.
    Gail S, Dagaut P, Black G, Simmie JM (2008) Kinetics of 1,2-dimethylbenzene oxidation and ignition: experimental and detailed chemical kinetic modeling. Combust Sci Technol 180(10–11):1748–1771.  https://doi.org/10.1080/00102200802258270 Google Scholar
  34. 34.
    Marotta E, Callea A, Ren XW, Rea M, Paradisi C (2008) DC corona electric discharges for air pollution control, 2-ionic intermediates and mechanisms of hydrocarbon processing. Plasma Process Polym 5(2):146–154.  https://doi.org/10.1002/ppap.200700128 Google Scholar
  35. 35.
    Wang QD, Wang JB, Li JQ, Tan NX, Li XY (2011) Reactive molecular dynamics simulation and chemical kinetic modeling of pyrolysis and combustion of n-dodecane. Combust Flame 158(2):217–226.  https://doi.org/10.1016/j.combustflame.2010.08.010 Google Scholar
  36. 36.
    Hayashibara K, Kruppa GH, Beauchamp JL (1986) Photoelectron-spectroscopy of the ortho-methylbenzyl, meta-methylbenzyl, para-methylbenzyl radicals—implications for the thermochemistry of the radicals and ions. J Am Chem Soc 108(18):5441–5443.  https://doi.org/10.1021/ja00278a011 Google Scholar
  37. 37.
    Staszewska E, Pawlowska M (2012) Control of landfill gases emission with particular emphasis on BTEX. Ecol Chem Eng S 19(2):239–248.  https://doi.org/10.2478/v10216-011-0018-7 Google Scholar
  38. 38.
    Neyts EC, Bogaerts A (2014) Understanding plasma catalysis through modelling and simulation—a review. J Phys D Appl Phys 47(22):18.  https://doi.org/10.1088/0022-3727/47/22/224010 Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Tianyu Shou
    • 1
    • 2
  • Nan Xu
    • 1
  • Yihan Li
    • 1
  • Guojin Sun
    • 3
  • Matthew T. Bernards
    • 4
  • Yao Shi
    • 1
    • 2
  • Yi He
    • 1
    • 5
    Email author
  1. 1.College of Chemical and Biological EngineeringZhejiang UniversityHangzhouChina
  2. 2.Key Laboratory of Biomass Chemical Engineering of Ministry of EducationZhejiang UniversityHangzhouChina
  3. 3.Zhejiang Province Radiation Environmental Monitoring StationHangzhouChina
  4. 4.Department of Chemical and Materials EngineeringUniversity of IdahoMoscowUSA
  5. 5.Department of Chemical EngineeringUniversity of WashingtonSeattleUSA

Personalised recommendations