Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

Study on the Liquid Phase Reaction of Ozone with Ethylbenzene and Its Derivatives

Andriy Galstyan1, Yurii Vashkurak2, Volodymyr Reutskyy2, Volodymyr Starchevskyy2, Andrii Burda2
Affiliation: 
1 National University of Life and Environmental Sciences of Ukraine, 15 Heroiv Oborony St., Kyiv 03041, Ukraine 2 Lviv Polytechnic National University, 12 S. Bandery St., Lviv 79013, Ukraine aggaalst@nubip.edu.ua
DOI: 
https://doi.org/10.23939/chcht18.04.510
AttachmentSize
PDF icon full_text.pdf428.43 KB
Abstract: 
This work deals with the investigation of the reactions of ethylbenzene and its derivatives with ozone in a solution of glacial acetic acid. The products and kinetic features of oxidation were studied, the kinetic parameters of the reactions were found, and the mechanism of ozonation in the liquid phase was proposed. The influence of deactivating substituents (-Br, -NO2) in the aromatic ring on the selectivity of the side chain oxidation of the substrate was established. It is shown that the main direction of ethylbenzene oxidation is ozonolysis with the formation of aliphatic compounds, while the ozonation of p-bromomethylbenzene and p-nitroethylbenzene significantly increases the selectivity of the side chain oxidation of the substrate, and the corresponding acetophenones become the main products of the reaction. The kinetics of the reaction were studied using gas chromatography and spectrophotometry, measuring the optical density of the gas flow in the UV region.
References: 

[1] Unnarkat, A.P.; Sonani, J.; Baldha, J.; Agarwal, S.; Manvar, K.; Faraji, A.R.; Arshadi, M. Catalytic Oxidation of Ethylbenzene: Kinetic Modeling, Mechanism, and Implications. Chem. Pap. 2022, 76, 995-1008. https://doi.org/10.1007/s11696-021-01920-4
https://doi.org/10.1007/s11696-021-01920-4

[2] Sliwiok J.; Ogierman L. Selective Air Oxidation of Ethylbenzene to Acetophenone. Org. Prep. Proced. Int. 1973, 5, 21-23. https://doi.org/10.1080/00304947309356458
https://doi.org/10.1080/00304947309356458

[3] Hwang, K.Ch.; Sagadevan, A.; Sustainable, P.Ch.; Hwang, K.K. The Sustainable Room Temperature Conversion of p-Xylene to Terephthalic Acid Using Ozone and UV Irradiation. Green Chem. 2019, 22, 2-8. https://doi.org/10.1039/C9GC02095K
https://doi.org/10.1039/C9GC02095K

[4] Pan, H.; Li, S.; Shu, M.; Cui, Q.; Zhao, Z. р-Xylene Catalytic Oxidation to Terephthalic Acid by Ozone. Science Asia 2018, 44, 212-217. https://doi.org/10.2306/scienceasia1513-1874.2018.44.212
https://doi.org/10.2306/scienceasia1513-1874.2018.44.212

[5] Potapenko, E.V.; Andreev, P.Y.; Isayenko, I.P.; Andreeva, N.S. Katalitychne okysnennia toluenu ozonom v systemi "otstovyi anhidryd - sylna kyslota". Voprosy Khimii i Khimicheskoi Tekhnologii 2021, 4, 106-111. https://doi.org/10.32434/0321-4095-2021-137-4-106-111.
https://doi.org/10.32434/0321-4095-2021-137-4-106-111

[6] Razumovskyi, S.D.; Halstian, H.A.; Tiupalo, M.F. Ozon ta yoho reaktsii z alifatychnymy spolukamy; SUDU: Luhansk, 2000.

[7] Halstian S.H.; Tiupalo N.F.; Halstian A.H. Kinetyka okysnennia toluolu ozonopovitrianoiu sumishshiu v otstovomu anhidrydi. Ukrainskyi khimichnyi zhurnal 2010, 76, 26-30.

[8] Chumbhale, VR; Paradhy, SA; Anilkumar, M; Kadam, ST; Bokade, V.V. Vapour Phase Oxidation of Acetophenone to Benzoicacid over Binary Oxides of V and Mo. Chem. Eng. Res. Des. 2003, 83, 75-83. https://doi.org/10.1205/cherd.03206
https://doi.org/10.1205/cherd.03206

[9] Andreiev, P.Yu.; Halstian, H.A.; Halstian, A.H. Kinetyka ta mekhanizm okyslennia nitrotoluoliv ozonom u rozchyni otstovoi kysloty. Ukrainskyi khimichnyi zhurnal 2005, 71, 43-46.

[10] Galstyan, A.; Galstyan, G.; Timoshyna, L. Research of the Process of Liquid Phase Selective Oxidation of 4-Aminotoluene with Ozone. Chem. Chem. Technol. 2018, 12, 341-345. https://doi.org/10.23939/chcht12.03. 341
https://doi.org/10.23939/chcht12.03