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).
  • 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).

Kinetic Model of the Process of Polycondensation of Concentrated Phenols of Coal Tar with Formaldehyde

Volodymyr Gunka1,Yuriy Demchuk1,2, Iryna Drapak2, Bohdan Korchak1, Michael Bratychak1
Affiliation: 
1 Lviv Polytechnic National University, 12 S.Bandery St., 79013 Lviv, Ukraine 2 Danylo Halytsky Lviv National Medical University, 69 Pekarska St., 79010 Lviv, Ukraine volodymyr.m.hunka@lpnu.ua
DOI: 
https://doi.org/10.23939/chcht17.02.339
AttachmentSize
PDF icon full_text.pdf575.03 KB
Abstract: 
Phenolformaldehyde resins were obtained by polycondensation of concentrated phenols with formaldehyde in the presence of hydrochloric acid. Concentration of phenols is carried out by treating the phenolic fraction of coal tar with an aqueous solution of sodium hydroxide followed by neutralization of water-soluble phenolates with hydrochloric acid. The kinetic dependences of resin yield and softening temperature on the duration of the process at 333, 353, and 373 K were obtained. The order of the reaction was determined and the effective activation energy of this process was determined by a graphical method. In the interval 333-373 K for polycondensation reactions, the equation of the dependence of the resin yield on the temperature and duration of the process was obtained.
References: 

[1] Smith, A. Verfahren zur Herstellung eines Ersatzmaterials für Ebonit, Holz u. dgl. DE 112685, October 10, 1899.

[2] Baekeland, L.H. Method of making insoluble products of phenol and formaldehyde. US 942699, December 7, 1909.

[3] Burkhart, T.; Oberressl, P.; Oldring, P.K.T. The chemistry and application of phenolic resins or phenolplasts; John Wiley & Sons, 1998.

[4] Xu, Y.; Guo, L.; Zhang, H.; Zhai, H.; Ren, H. Research Status, Industrial Application Demand and Prospects of Phenolic Resin. RSC Adv. 2019, 9, 28924-28935. https://doi.org/10.1039/C9RA06487G
https://doi.org/10.1039/C9RA06487G

[5] Moshchynskaia, N.K. Polymernye materialy na osnove aro-maticheskikh uhlevodorodov i formaldehida; Tekhnika: Kyiv, 1970.

[6] Wegler, R. Beitrag zur Phenolharz-Analyse. Angew. Chemie A1948, 60, 88-95.
https://doi.org/10.1002/ange.19480600403

[7] Verdot, J.A.; Rayan, P.W. Encyclopedia of polymer science and technology, Vol. 7; 1967, pp539-557.

[8] Hashimoto, K.; Osaki, H.; Uetani, Y. Positive resist composi-tion comprising a novolac resin made from a cycloalkyl substituted phenol. US 5792586, August 11, 1998.

[9] Chauvin, B.M.; Durel, O. Process and composition for the use of substituted melamines as hardeners of novolac resins. US 5763558, June 9, 1998.

[10] Gelling, P.J.; Hunt, J.E.B.; Marshman, J.D. Continuous production of phenol-formaldehyde resin and laminates produced therefrom. US 4413113, November 1, 1983.

[11] Petersen, H.; Krause, H.-J.; Fischer, K.; Segnitz, A.; Zaun-brecher, H. Cocondensates based on phenol-butyraldehyde resins, their preparation and their use. US 4276209, June 30,1981.

[12] Gerber, A.H. Phenol-novolacs with improved optical proper-ties. US 6316583, November 13, 2001.

[13] Van Benthem, R.A.T.M. Process for the preparation of a hydroxy-aromatic resin; hydroxy-aromatic resin, and modification thereof. Patent WO/2007/140941, December 13,2007.

[14] Zhao, Y.; Mao, X.; Li, W.; Gu, X.; Wang, G. Study on Ex-traction Phenol from Coal Tar with High Flux Centrifugal Extractor. Int. J. Coal Sci. Technol. 2017, 4, 333-341. https://doi.org/10.1007/s40789-017-0182-1
https://doi.org/10.1007/s40789-017-0182-1

[15] Pyshyev, S.; Demchuk, Y.; Poliuzhyn, I.; Kochubei, V. Obtaining and Use Adhesive Promoters to Bitumen from the Phenolic Fraction of Coal Tar. Int. J Adhes. Adhes. 2022, 118, 103191. https://doi.org/10.1016/j.ijadhadh.2022.103191
https://doi.org/10.1016/j.ijadhadh.2022.103191

[16] Jiao, T.; Zhuang, X.; He, H.; Li, C.; Chen, H.; Zhang, S. Separation of Phenolic Compounds from Coal Tar via Liquid-Liquid Extraction Using Amide Compounds. Ind. Eng. Chem. Res. 2015, 54, 2573-2579. https://doi.org/10.1021/ie504892g
https://doi.org/10.1021/ie504892g

[17] Li, Y.; Luo, H. A.; Ai, Q.; You, K.; Zhao, F.; Xiao, W. Effi-cient Separation of Phenols from Coal Tar with Aqueous Solution of Amines by Liquid-Liquid Extraction. Chin. J. Chem. Eng. 2021, 35, 180-188. https://doi.org/10.1016/j.cjche.2021.01.008
https://doi.org/10.1016/j.cjche.2021.01.008

[18] Riccardi, C.C.; Aierbe, G.A.; Echeverria, J.M.; Mondragon, I. Modelling of Phenolic Resin Polymerisation. Polymer2002, 43, 1631-1639. https://doi.org/10.1016/S0032-3861(01)00736-4
https://doi.org/10.1016/S0032-3861(01)00736-4

[19] Pyshyev, S.; Demchuk, Y.; Gunka, V.; Sidun, I.; Shved, M.; Bilushchak, H.; Obshta, A. Development of Mathematical Model and Identification of Optimal Conditions to Obtain Phenol-Cresol-Formaldehyde Resin. Chem. Chem. Technol. 2019, 13, 212-217. https://doi.org/10.23939/chcht13.02.212
https://doi.org/10.23939/chcht13.02.212

[20] Bratychak, M.M., Hetmanchuk, Yu.P. Khimichna tekhnolo-hiya syntezu vysokomolekularnykh spoluk;Publishing House of Lviv Polytechnic National University: Lviv, 2009.

[21] Çubuk, M.; Gürü, M. M.; Çubuk, K.; Arslan, D. Rheological Properties and Performance Evaluation of Phenol Formaldehyde Modified Bitumen. J. Mater. Civil Eng.2014, 26, 04014015. https://doi.org/10.1061/(ASCE)MT.1943-5533.0000889
https://doi.org/10.1061/(ASCE)MT.1943-5533.0000889

[22] Demchuk, Y.; Gunka, V.; Pyshyev, S.; Sidun, I.; Hrynchuk, Y.; Kucińska-Lipka, J.; Bratychak, M. Slurry Surfacing Mixes on the Basis of Bitumen Modified with Phenol-Cresol-Formaldehyde Resin. Chem. Chem. Technol.2020, 14, 251-256. https://doi.org/10.23939/chcht14.02.251
https://doi.org/10.23939/chcht14.02.251

[23] Demchuk, Y.; Gunka, V.; Sidun, I.; Solodkyy, S. Comparison of Bitumen Modified by Phenol Formaldehyde Resins Synthesized from Different Raw Materials. Lect. Notes Civ. Eng.2020, 100, 95-102. https://doi.org/10.1007/978-3-030-57340-9_12
https://doi.org/10.1007/978-3-030-57340-9_12

[24] Gunka, V.; Demchuk, Y.; Sidun, I.; Miroshnichenko, D.; Nyakuma, B.B.; Pyshyev, S. Application of Phenol-Cresol-Formaldehyde Resin as an Adhesion Promoter for Bitumen and Asphalt Concrete. Road Mater. Pavement Des.2021, 22, 2906-2918. https://doi.org/10.1080/14680629.2020.1808518
https://doi.org/10.1080/14680629.2020.1808518

[25] Pyshyev, S.; Demchuk, Y.; Poliuzhyn, I.; Kochubei, V. Obtaining and Use Adhesive Promoters to Bitumen from the Phenolic Fraction of Coal Tar. Int. J Adhes. Adhes. 2022, 118, 103191. https://doi.org/10.1016/j.ijadhadh.2022.103191
https://doi.org/10.1016/j.ijadhadh.2022.103191

[26] Bratychak, M.; Brzozowski, Z.; Bukowski, A.; Daniewska, I.; Florjanczyk, Z.; Listos, T.; Lukasik, L.; Maciejewski, M.; Makaruk, L.; Pron, A. et al. Cwiczenia laboratoryjne z chemii i technologii polimerow; OWPW: Warszawa, 1997.

[27] Emanuel, N.M.; Knorre, D.G. Chemical Kinetics: Homogeneous Reactions, First ed.; Israel Program for Scientific Translations: Jerusalem, 1973.

[28] Ginell, R.; Simha, R. On the Kinetics of Polymerization Reac-tions. II. Second and Combined First and Second Order Initiation Reactions. Mutual Stabilization of Growing Chains1. J. Am. Chem. Soc. 1943, 65, 715-727. https://doi.org/10.1021/ja01244a057
https://doi.org/10.1021/ja01244a057

[29] Yang, Y.; Muhich, C.L.; Green, M.D. Kinetics and Mechan-isms of Polycondensation Reactions between Aryl Halides and Bisphenol A. Polym. Chem. 2020, 11, 5078-5087. https://doi.org/10.1039/D0PY00740D
https://doi.org/10.1039/D0PY00740D