Research into epoxidation process of the С9 fraction hydrocarbons and unsaturated co-oligomers by peroxyethanoic acid
DOI:
https://doi.org/10.15587/1729-4061.2018.126682Keywords:
С9 fraction, epoxy-containing co-oligomers, epoxidation selectivity, epoxy number, IR spectroscopy, Raman spectroscopy, 1H NMR spectroscopyAbstract
We have studied regularities of the epoxidation process of the С9 fraction of liquid by-products of the pyrolysis of hydrocarbons and co-oligomers based on the С9 fraction with peracetic acid. It is established that the use of the specified system makes it possible to achieve high values of conversion for double bonds and the selectivity of epoxidation process, sufficiently high yield of epoxy-containing co-oligomers. We established the possibility to use the С9 fraction of liquid by-products of hydrocarbon pyrolysis (the accompanying product of ethylene production) as a raw material for obtaining epoxides, which is a rational method in order to dispose of the fraction. We analyzed experimental dependences of reagents consumption and the formation of epoxide in the reaction of the С9 fraction epoxidation. It was established that the resulting values for selectivities of the epoxidation process by double bonds when obtaining epoxy-containing co-oligomers are the highest in the case of epoxidation of co-oligomers, synthesized by the heterogeneous catalytic co-oligomerization of the С9 fraction S9 hydrocarbons using, as a catalyst, activated bentonite clay. The synthesized epoxy-containing co-oligomers retain residual unsaturation. It is obvious that the unsaturated bonds of styrene, vinyl toluene, α-methyl styrene, allylbenzene links at the ends of a co-oligomer macromolecules are easily epoxidized. The selectivity of epoxidation of co-oligomers, obtained by different methods of co-oligomerization of the С9 fraction hydrocarbons (homogeneous catalytic, heterogeneous catalytic, initiated, and thermal) is different (60.2‒96.1 %) and depends on the nature of the starting co-oligomer. Using the methods of 1H NMR-, Raman-, and infrared spectroscopy, we confirmed the high content of epoxy groups in the composition of epoxy-containing co-oligomers and the progress of the epoxidation reaction. Applying the method of 1H NMR spectroscopy, we established the presence of epoxy groups formed based on the resulting vinyl double bonds of co-oligomers. Due to the content of oxirane oxygen and a high reaction ability of the oxirane ring, epoxy-containing co-oligomers can act as the raw material for subsequent obtaining of various chemical substances: glycols, carbonyl compounds, plasticizers, polymers.
References
- Slavgorodskaya, O. I., Bondaletov, V. G., Lyapkov, A. A., Ustimenko, J. P., Vervacke, D. (2014). Kinetics of Petroleum Resin Epoxidation by Peracetic Acid. Procedia Chemistry, 10, 555–559. doi: 10.1016/j.proche.2014.10.094
- Voronchak, T., Nykulyshyn, I., Pikh, Z., Rypka, A., Gnativ, Z. (2013). Cooligomerization of dominant monomers of C9 fraction of liquid pyrolysis products: comparison of heterogeneous catalytic approach with common methods. Central European Journal of Chemistry, 12 (2), 266–280. doi: 10.2478/s11532-013-0369-2
- Talybov, G. M. (2017). Epoxidation of unsaturated carbonyl compounds. Russian Journal of Organic Chemistry, 53 (11), 1742–1745. doi: 10.1134/s1070428017110239
- Nykulyshyn, I., Voronchak, T., Pikh, Z., Rypka, A. (2012). Heterogeneous oligomerization catalysts: properties and efficiency. Open Chemistry, 10 (6). doi: 10.2478/s11532-012-0107-1
- Bratychak, M., Bashta, B., Bruzdziak, P., Astakhova, O., Shyshchak, O. (2013). Cross-Linking of Epoxy-Oligoesteric Mixtures in the Presence of Carboxy-Containing Derivative of ED-24 Epoxy Resin. Chemistry & Chemical Technology, 7 (1).
- Bashta, B., Astakhova, O., Shyshchak, O., Bratychak, M. (2014). Epoxy Resins Chemical Modification by Dibasic Acids. Chemistry & Chemical Technology, 8 (3), 309–316.
- Czub, P., Franek, I. (2013). Epoxy resins modified with palm oil derivatives – preparation and properties. Polimery, 58 (2), 135–139. doi: 10.14314/polimery.2013.135
- Kukurina, O. S., Slavgorodskaya, O. I., Ustimenko, Y. P. (2014). Liquid Phase Petroleum Resin Oxidation by Systems Based on Hydrogen Peroxide. Advanced Materials Research, 1040, 323–326. doi: 10.4028/www.scientific.net/amr.1040.323
- Abdulmalek, E., Arumugam, M., Mizan, H. N., Abdul Rahman, M. B., Basri, M., Salleh, A. B. (2014). Chemoenzymatic Epoxidation of Alkenes and Reusability Study of the Phenylacetic Acid. The Scientific World Journal, 2014, 1–7. doi: 10.1155/2014/756418
- Brocas, A.-L., Llevot, A., Mantzaridis, C., Cendejas, G., Auvergne, R., Caillol, S. et. al. (2013). Epoxidized rosin acids as co-precursors for epoxy resins. Designed Monomers and Polymers, 17 (4), 301–310. doi: 10.1080/15685551.2013.840504
- Nykulyshyn, I., Pikh, Z., Shevchuk, L., Melnyk, S. (2017). Examining the epoxidation process of soybean oil by peracetic acid. Eastern-European Journal of Enterprise Technologies, 3 (6 (87)), 21–28. doi: 10.15587/1729-4061.2017.99787
- Odabash'yan, G. V., Shvec, V. F. (1992). Laboratornyy praktikum po himii i tekhnologii osnovnogo organicheskogo i neftekhimicheskogo sinteza. Moscow: Himiya, 240.
- Siggia, S., Hanna, Dzh. G. (1983). Kolichestvenniy organicheskiy analiz po funkcional'nym gruppam. Moscow: Himiya, 672.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2018 Irena Nykulyshyn, Taras Chaikivskyi, Zorian Pikh
This work is licensed under a Creative Commons Attribution 4.0 International License.
The consolidation and conditions for the transfer of copyright (identification of authorship) is carried out in the License Agreement. In particular, the authors reserve the right to the authorship of their manuscript and transfer the first publication of this work to the journal under the terms of the Creative Commons CC BY license. At the same time, they have the right to conclude on their own additional agreements concerning the non-exclusive distribution of the work in the form in which it was published by this journal, but provided that the link to the first publication of the article in this journal is preserved.
A license agreement is a document in which the author warrants that he/she owns all copyright for the work (manuscript, article, etc.).
The authors, signing the License Agreement with TECHNOLOGY CENTER PC, have all rights to the further use of their work, provided that they link to our edition in which the work was published.
According to the terms of the License Agreement, the Publisher TECHNOLOGY CENTER PC does not take away your copyrights and receives permission from the authors to use and dissemination of the publication through the world's scientific resources (own electronic resources, scientometric databases, repositories, libraries, etc.).
In the absence of a signed License Agreement or in the absence of this agreement of identifiers allowing to identify the identity of the author, the editors have no right to work with the manuscript.
It is important to remember that there is another type of agreement between authors and publishers – when copyright is transferred from the authors to the publisher. In this case, the authors lose ownership of their work and may not use it in any way.
