Technology of obtaining water-soluble surface-active substances by the method of phenol sulfomethylation

Authors

  • Nadiia Sokolenko Institute of Chemical Technologies of the East Ukrainian National University named after V. Dal Volodymyrska str., 31, Rubizhne, Ukraine, 93009, Ukraine https://orcid.org/0000-0002-1319-2625
  • Yevgeniy Popov Institute of Chemical Technologies of the East Ukrainian National University named after V. Dal Volodymyrska str., 31, Rubizhne, Ukraine, 93009, Ukraine https://orcid.org/0000-0001-7941-5134
  • Kateryna Fastovetska Institute of Chemical Technologies of the East Ukrainian National University named after V. Dal Volodymyrska str., 31, Rubizhne, Ukraine, 93009, Ukraine https://orcid.org/0000-0003-0826-9285

DOI:

https://doi.org/10.15587/1729-4061.2020.210718

Keywords:

phenol, formaldehyde, cetyltrimethylammonium bromide, sulfomethylation, interphase catalysis, surface-active substances, dispersant

Abstract

The object of this study is a technology of the new surface-active substances (SAS) based on sulfomethylated phenol. The study's aim was to improve the technology by a catalytic method, implying the development of industrial schemes for the synthesis processes.

During phenol sulfomethylation, the active conversion of monomers into polymeric substances starts only at a temperature of 110‒120 °C; the surface-active substances with an optimal polymeric composition were obtained only at a temperature of 130 °C. In the reaction of phenol sulfomethylation in a water environment at a temperature below 90 °C, obtaining SAS with the required properties takes more than 9 hours. The significant disadvantages of this technique are the relatively low yield of the target product and a significant amount of free phenol in the finished product (over 15 percent).

It is known that a more powerful and less risky technique to accelerate the reaction than rising the temperature is catalysis.

This study investigated the reaction of phenol sulfomethylation under conditions of interphase catalysis. This has made it possible to improve the main technological parameters: the reaction temperature was reduced from 130 °C to 90 °C, the process duration was shortened to 3 hours, to process was conducted at atmospheric pressure. The catalyst used was a cation-active SAS: cetyltrimethylammonium bromide. This makes it possible to simplify the technological scheme of obtaining SAS, that is, to use less energy-intensive and cheap reactors.

A benefit of the proposed technology is the low-waste, single-stage production, and the use of available raw materials: phenol, formaldehyde, and sodium sulfite. During the study, the products were obtained that are similar, in terms of the surface-active properties, to the NF Dispersant, which is widely used in the industry. This makes it possible to expand the range of multifunctional surface-active substances with better bio destruction than products based on naphthalene and lignin.

According to the results of studying the samples obtained, the scope of their application has been proposed. The resulting products have been tested, with positive results, as the anion-active SAS, used as dispersants in the production of organic dyes, as aligners when dyeing textiles, and as plasticizing additives for concrete mixtures

Author Biographies

Nadiia Sokolenko, Institute of Chemical Technologies of the East Ukrainian National University named after V. Dal Volodymyrska str., 31, Rubizhne, Ukraine, 93009

Assistant, Head of Training Laboratory

Department of Ecology and Polymer Technology

Yevgeniy Popov, Institute of Chemical Technologies of the East Ukrainian National University named after V. Dal Volodymyrska str., 31, Rubizhne, Ukraine, 93009

Doctor of Technical Sciences, Professor

Department of Ecology and Polymer Technology

Kateryna Fastovetska, Institute of Chemical Technologies of the East Ukrainian National University named after V. Dal Volodymyrska str., 31, Rubizhne, Ukraine, 93009

PhD

Department of Ecology and Polymer Technology

References

  1. Brycki, B. E., Kowalczyk, I. H., Szulc, A., Kaczerewska, O., Pakiet, M. (2017). Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications. Application and Characterization of Surfactants. doi: https://doi.org/10.5772/intechopen.68755
  2. Surfactants Market by Type (Anionic, Non-Ionic, Cationic, and Amphoteric), Application (Home Care, Personal Care, Industrial & Institutional Cleaning, Textile, Elastomers & Plastics, Agrochemicals, and Food & Beverage), Region - Global Forecast to 2025. Available at: https://www.marketsandmarkets.com/Market-Reports/biosurfactants-market-493.html
  3. Lange, K. R.; Zaychenko, L. P. (Ed.) (2005). Poverhnostno-aktivnye veshchestva: sintez, svoystva, analiz, primenenie. Sankt-Peterburg: Professiya, 240.
  4. Krichevskiy, G. E. (2001). Himicheskaya tehnologiya tekstil'nyh materialov. Vol. 2. Kolorirovanie tekstil'nyh materialov. Moscow: Himiya, 540.
  5. Heylen, V. (2009). Dobavki dlya pokrytiy na vodnoy osnove. Vincentz Network GmbH, 222.
  6. Volkov, V. A. (2010). Poverhnostno-aktivnye veshchestva. Primenenie dlya proizvodstva i modifikatsii tekstil'nyh materialov.
  7. Shishkin, A. (2016). Study of the effect of compounds of transition elements on the micellar catalysis of strength formation of reactive powder concrete. Eastern-European Journal of Enterprise Technologies, 2 (6 (80)), 60–65. doi: https://doi.org/10.15587/1729-4061.2016.63957
  8. Koval', S. V. (2004). Modifitsirovanie – magistral'noe napravlenie sovershenstvovaniya tehnologii i svoystv betona. Budivelni materialy ta vyroby, 4, 20–24.
  9. Marco, P., Llorens, J. (2007). Understanding of naphthalene sulfonate formaldehyde condensates as a dispersing agent to stabilise raw porcelain gres suspensions. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 299 (1-3), 180–185. doi: https://doi.org/10.1016/j.colsurfa.2006.11.034
  10. Marco, P., Carballo, M., Llorens, J. (2009). Stabilization of raw porcelain gres suspensions with sodium naphthalene sulfonate formaldehyde condensates. Applied Clay Science, 42 (3-4), 473–477. doi: https://doi.org/10.1016/j.clay.2008.06.003
  11. El-Gamal, S. M. A., Al-Nowaiser, F. M., Al-Baity, A. O. (2012). Effect of superplasticizers on the hydration kinetic and mechanical properties of Portland cement pastes. Journal of Advanced Research, 3 (2), 119–124. doi: https://doi.org/10.1016/j.jare.2011.05.008
  12. Qian, Y., De Schutter, G. (2018). Different Effects of NSF and PCE Superplasticizer on Adsorption, Dynamic Yield Stress and Thixotropy of Cement Pastes. Materials, 11 (5), 695. doi: https://doi.org/10.3390/ma11050695
  13. Osuji, S. O., Ikogho, D. (2018). Current Effects of Naphthalene Based Superplasticizer’s Addition Process on Water Reduction and Grade C20/25 Concrete’s Compressive Strength. Journal of Civil Engineering Research, 8 (1), 9–14.
  14. Aro, T., Fatehi, P. (2017). Production and Application of Lignosulfonates and Sulfonated Lignin. ChemSusChem, 10 (9), 1861–1877. doi: https://doi.org/10.1002/cssc.201700082
  15. Bajwa, D. S., Pourhashem, G., Ullah, A. H., Bajwa, S. G. (2019). A concise review of current lignin production, applications, products and their environmental impact. Industrial Crops and Products, 139, 111526. doi: https://doi.org/10.1016/j.indcrop.2019.111526
  16. He, W., Fatehi, P. (2015). Preparation of sulfomethylated softwood kraft lignin as a dispersant for cement admixture. RSC Advances, 5 (58), 47031–47039. doi: https://doi.org/10.1039/c5ra04526f
  17. Huang, C., Ma, J., Zhang, W., Huang, G., Yong, Q. (2018). Preparation of Lignosulfonates from Biorefinery Lignins by Sulfomethylation and Their Application as a Water Reducer for Concrete. Polymers, 10 (8), 841. doi: https://doi.org/10.3390/polym10080841
  18. Yu, G., Li, B., Wang, H., Liu, C., Mu, X. (2013). Preparation of Concrete Superplasticizer by Oxidation-Sulfomethylation of Sodium Lignosulfonate. BioResources, 8 (1). doi: https://doi.org/10.15376/biores.8.1.1055-1063
  19. Ye, X.-X., Luo, W., Lin, L., Zhang, Y., Liu, M. (2016). Quaternized lignin-based dye dispersant: Characterization and performance research. Journal of Dispersion Science and Technology, 38 (6), 852–859. doi: https://doi.org/10.1080/01932691.2016.1207545
  20. Qin, Y., Yang, D., Gu, F., Li, X., Xiong, W., Zhu, J. Y. (2016). Biorefinery lignosulfonates as a dispersant for coal water slurry. Sustainable Chemical Processes, 4 (1). doi: https://doi.org/10.1186/s40508-016-0050-0
  21. Seo, J.-S., Keum, Y.-S., Li, Q. (2009). Bacterial Degradation of Aromatic Compounds. International Journal of Environmental Research and Public Health, 6 (1), 278–309. doi: https://doi.org/10.3390/ijerph6010278
  22. Karimi, B., Habibi, M., Esvand, M. (2015). Biodegradation of naphthalene using Pseudomonas aeruginosa by up flow anoxic–aerobic continuous flow combined bioreactor. Journal of Environmental Health Science and Engineering, 13 (1). doi: https://doi.org/10.1186/s40201-015-0175-1
  23. Chatterjee, B., Mandal, S., Mazumder, D. (2019). Aerobic biodegradation of lignosulfonate bearing synthetic wastewater using activated sludge. Journal of the Indian Chemical Society, 96 (4), 461–468. Available at: http://www.indianchemicalsociety.com/portal/uploads/journal/2019_04_8_Extended_1556597293.pdf
  24. Rochman, F. F., Sheremet, A., Tamas, I., Saidi-Mehrabad, A., Kim, J.-J., Dong, X. et. al. (2017). Benzene and Naphthalene Degrading Bacterial Communities in an Oil Sands Tailings Pond. Frontiers in Microbiology, 8. doi: https://doi.org/10.3389/fmicb.2017.01845
  25. Lee, Y., Lee, Y., Jeon, C. O. (2019). Biodegradation of naphthalene, BTEX, and aliphatic hydrocarbons by Paraburkholderia aromaticivorans BN5 isolated from petroleum-contaminated soil. Scientific Reports, 9 (1). doi: https://doi.org/10.1038/s41598-018-36165-x
  26. Maas, H., Narbeshuber, T., Roeper, M. (2000). Pat. No. DE10039995A1. Process for the preparation of alkylarylsulfonates. declareted: 11.08.2000; published: 21.02.2002. Available at: https://patents.google.com/patent/DE10039995A1/en
  27. Demineralizatsiya metodom elektrodializa. (Ionitovye membrany) (1963). Moscow: Gosatomizdat, 351. Available at: https://search.rsl.ru/ru/record/01006108138
  28. Wang, Q., Liu, F., Yu, S. (2008). Preparation of sulfomethylated phenol formaldehyde resin. Available at: https://www.researchgate.net/publication/291081246_Preparation_of_sulfomethylated_phenol_formaldehyde_resin
  29. Péreza, J. M., Rodrígueza, F., Alonsoa, M. V., Olieta, M., Echeverría, J. M. (2007). Characterization of a novolac resin substituting phenol by ammonium lignosulfonate as filler or extender. BioResources, 2 (2), 270–283. Available at: https://www.researchgate.net/publication/26460127_Characterization_of_a_novolac_resin_substituting_phenol_by_ammonium_lignosulfonate_as_filler_or_extender
  30. Zhuravlev, V. A., Murashkina, T. V. (2005). Issledovanie protsessa i sostava produktov sul'fometilirovaniya fenola. Vestnik Kuzbasskogo gosudarstvennogo tehnicheskogo universiteta, 6 (51), 85–87. Available at: https://cyberleninka.ru/article/n/issledovanie-protsessa-i-sostava-produktov-sulfometilirovaniya-fenola/viewer
  31. Sokolenko, N. M., Popov, Е. V. (2019). Studying the conditions of the process of phenol, formaldehyde and sodium sulfite condensation in the technology of water-soluble surfactants. Visnik of the Volodymyr Dahl East Ukrainian National University, 8 (256), 81–85. doi: https://doi.org/10.33216/1998-7927-2019-256-8-81-85
  32. Sokolenko, N., Ruban, E., Ostrovka, V., Oleksiy, M., Popov, Y., Sedych, A. (2020). Study of the toxicological characteristics of water-soluble surface-active substances obtained based on phenol, formaldehyde and sodium sulphite. Technology Audit and Production Reserves, 1 (3 (51)), 44–47. doi: https://doi.org/10.15587/2312-8372.2020.193074
  33. Ostrovskii, V. A. (2000). Interphase transfer catalysis of organic reactions. Sorosovskiy obrazovatel'niy zhurnal, 6 (11), 30–34. Available at: http://window.edu.ru/resource/478/21478/files/0011_030.pdf

Downloads

Published

2020-08-31

How to Cite

Sokolenko, N., Popov, Y., & Fastovetska, K. (2020). Technology of obtaining water-soluble surface-active substances by the method of phenol sulfomethylation. Eastern-European Journal of Enterprise Technologies, 4(6 (106), 45–53. https://doi.org/10.15587/1729-4061.2020.210718

Issue

Section

Technology organic and inorganic substances