Optimization of conditions for the synthesis of calyx[4]resorcinol conformers containing 4-dimethylammoniophenyl fragments on the lower rim of the molecule based on the response surface methodology using three-level box-behnken plans
- Authors: Bakeeva R.F1, Parfenova A.G1, Shatalovav N.I1, Sopin V.F1, Gavrilova E.L1
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Affiliations:
- Kazan National Research Technological University
- Issue: Vol 93, No 2 (2023)
- Pages: 253-265
- Section: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/145003
- DOI: https://doi.org/10.31857/S0044460X23020117
- EDN: https://elibrary.ru/QBZRZO
- ID: 145003
Cite item
Abstract
The response surface methodology using three-level Box-Behnken plans was applied in order to optimize the yield of the cone and chair conformers in the synthesis of calix[4]resorcinol functionalized with 4-dimethylammoniophenyl group along the lower rim. We used data from one-factor experiments in which the temperature, reaction time, and molar ratio of HCl to the reactants of the reaction mixture were varied to plot the response surfaces. The ratio of conformers was calculated based on the analysis of 1H NMR spectra of the products isolated from the reaction mixture. The adequacy of the proposed mathematical models for determining the yields of chair and cone conformations is confirmed by a high correlation coefficient ( R 0.99979). Optimal conditions were found for the maximum yield of the chair conformation (50°C, 2 h, molar ratio of HCl to reagents in the reaction mixture is 1-1.5, yield 100%). The optimal conditions for obtaining the cone conformation are: temperature 68.6°С, stirring time in the range of 2.24-6.44 h and the molar ratio of HCl to reagents in the reaction mixture is 2. Carrying out the synthesis under these conditions leads to the yield of the cone conformation in the range of 57.70-58.07%.
About the authors
R. F Bakeeva
Kazan National Research Technological University
Email: gurf71@mail.ru
A. G Parfenova
Kazan National Research Technological University
N. I Shatalovav
Kazan National Research Technological University
V. F Sopin
Kazan National Research Technological University
E. L Gavrilova
Kazan National Research Technological University
References
- Шаталова Н.И., Гаврилова Е.Л., Наумова А.А., Бурилов А.Р., Фосс Л.Е., Пудовик М.А., Красильникова Е.А., Коновалов А.И. // ЖОХ. 2005. Т. 75. Вып. 8. С. 1398
- Shatalova N.I., Gavrilova E.L., Naumova A.A., Krasil'nikova E.A., Konovalov A.I., Burilov A.R., Foss L.E., Pudovik M.A. // Russ. J. Gen. Chem. 2005. Vol. 75. N 8. P. 1327. doi: 10.1007/s11176-005-0419-3
- Шаталова Н.И. Автореф. дис. … канд. хим. наук. Казань, 2008. 20 с.
- Tunstad L., Tucker J., Dalcanale E., Weiser J. // J. Org. Chem. 1989. Vol. 54. N 6. P. 1305 doi: 10.1021/jo00267a015
- Miso S., Adams R.D., Guo D.-S., Zhang Q.-F. // J. Mol. Struct. 2003. Vol. 659. P. 119 doi: 10.1016/j.molstruc.2003.08.004.
- Guseva E.V., Gavrilova E.L., Naumova A.A., Shatalova N.I., Karimova D.T., Polovnyak V.K., Morozov V.I. // Russ. J. Gen. Chem. 2008. Vol. 78. N 12. P. 2308. doi: 10.1134/S1070363208120049
- Гусева Е.В., Каримова Д.Т., Половняк В.К., Егоров Г.В., Гаврилова Е.Л., Шаталова Н.И., Морозов В.И., Соколова А.В. // Вестн. Казанск. технол. унив. 2009. № 5. С. 288.
- Пашина И.П. Автореф. дис. … канд. биол. наук. Москва, 2013. 24 с.
- Khuri AI. // Biom. Biostat. Int. J. 2017. Vol. 5. N 3. P. 87. doi: 10.15406/bbij.2017.05.00133
- Адлер Ю.П., Маркова Е.В., Граеновский Ю.В. Планирование при поиске оптимальных условий. М.: Мир, 2004. 725 c.
- Box G.E.P., Hunter J.S., Hunter W.G., Statistics for Experimenters. Design, Innovation, and Discovery. New York: Wiley-Interscience, 2005. 633 p.
- Ferreira S.L.C., Bruns R.E., Ferreira H.S., Matos G.D., David J.M., Brandao G.C., Silva E.G.P., Portugal L.A., Reisc P.S., Souza A.S., Santos W. // Analyt. Chim. Acta. 2007. Vol. 597. P. 179. doi: 10.1016/j.aca.2007.07.011
- Бакеева Р.Ф., Гармонов С.Ю., Вахитова О.Е., Сопин В.Ф. // ЖАХ. 2022. Т. 77. № 6. С. 540. doi: 10.31857/S0044450222060032
- Bakeeva R.F., Garmonov S.Yu, Vakhitova O.E., Sopin V.F. // J. Anal. Chem. 2022. Vol. 77. N 6. P. 686. doi: 10.1134/S106193482206003X
- Mohammadlou M., Jafarizadeh-Malmiri H., Maghsoudi H. // Green Proc. Synth. 2017. Vol. 6. P. 31. doi: 10.1515/gps-2016-0075
- Simões A.,Veiga F., Figueiras A., Vitorino C.A. // Int. J. Pharm. 2018. Vol. 548. N 1 P. 385. doi: 10.1016/j.ijpharm.2018.06.052
- Li Q., Wang Y., Li Q., Foster G., Lei C. // RSC Adv. 2018. Vol. 8. N 16. P. 8770. doi: 10.1039/c7ra13645e
- Jiang C., Sun G., Zhou Z., Lang X., Pang J., Li Y., Zhang X., Feng C., Chen X., Bao Z., Sun Q. // Int. J. Biol. Macromol. 2019. Vol. 121. P. 293. doi: 10.1016/j.ijbiomac.2018.09.210
- Agrawal D., Shrivastava Y., Singh P.K., De S.K. // J. Polymer Res. 2019. Vol. 26. N 7. P. 167. doi: 10.1007/s10965-019-1825-2
- Celebi N., Yildiz N., Calimli A., Demir A.S. // J. Supercr. Fluids. 2008.Vol. 47. N 2. P. 227. doi: 10.1016/j.supflu.2008.07.022
- Jourshabani M., Badiei A., Lashgari N., Ziarani G.M. // Chin. J. Catal. 2015. Vol. 36. N 11. P. 2020. doi: 10.1016/S1872-2067(15)60898-1
- Inger M., Dobrzyńska-Inger A., Rajewski J., Wilk M. // Catalysts. 2019. Vol. 9. N 3. P. 249. doi: 10.3390/catal9030249
- Pinheiro D., Sunaja Devi K.R., Jose A., Karthik K., Sugunan S., Krishna Mohan M. // J. Rare Earths. 2020. Vol. 38. N 11. P. 1171. doi: 10.1016/j.jre.2019.10.001
- Zhang Y., Zhao Q., Tang H., Li H., Li D., Wang Z., Gao X., Wang F. // Korean J. Chem. Eng. 2021. Vol. 38. N 5. P. 989. doi: 10.1007/s11814-021-0757-9
- Guolong Y., Lihui Y. // J. Oleo Sci. 2015. Vol. 64. N 6. P. 673. doi: 10.5650/jos.ess14285
- Sin K.P., Basri M., Rahman M.B.A., Salleh A.B., Rahman R.N.Z.A., Ariff A. // J. Oleo Sci. 2005. Vol. 54. N 10. P. 519. doi: 10.5650/jos.54.519
- Chaibakhsh N., Abdul Rahman M.B., Abd-Aziz S., Basri M, Salleh A.B., Abdul Rahman R.N.Z.R. // J. Ind. Microbiol. Biotechnol. 2009. Vol. 36. P. 1149. doi: 10.1007/s10295-009-0596-x
- Rosly N.Z., Ishak S., Abdullah A.H., Alang Ahmad S.A., Kamarudin M.A., Ashari S.E. // J. Saudi Chem. Soc. 2022. Vol. 26. N 1. P. 10140. doi: 10.1016/j.jscs.2021.1014022