A Green and Efficient Solvent- and Catalyst-Free Ultrasonic Dibenzylation Procedure

Simple item page
dc.citation.epage132
dc.citation.issue1
dc.citation.spage126
dc.contributor.affiliationSaveh University of Medical Sciences
dc.contributor.affiliationIslamic Azad University (IAUPS)
dc.contributor.authorHeydari, Somayyeh
dc.contributor.authorHabibi, Davood
dc.contributor.authorFaraji, Alireza
dc.coverage.placenameЛьвів
dc.coverage.placenameLviv
dc.date.accessioned2024-01-22T10:41:29Z
dc.date.available2024-01-22T10:41:29Z
dc.date.created2022-03-16
dc.date.issued2022-03-16
dc.description.abstractЗапропоновано екологічний синтез різноманітнихN,N-дибензильованих сполук внаслідок реакції різних ароматичних амінів з бензилбромідом за допомогою ультразвукового опромінення без розчинників та каталізаторів. Вивчено реакції дибензилування в різних розчинниках та без них за умов ультразвукового опромінення і різних температур. При застосуванні розчиників одержано дуже низькі виходи, а при реакції без розчинників та за кімнатної температури виходи є високими. У зв’язку з одержанням високих виходів реакції каталізатор не використовували.
dc.description.abstractA technology of briquetting of sub-standard coal of Kazakhstan fields to obtain high-quality briquetting fuel has been developed. A modifying additive in the form of oil residues has been selected, that make it possible to obtain a binder composition for brown coal briquetting. The material for the preparation of coal briquettes is coal fines from dry, poorly sintered coals, which cannot be used for direct combustion in the furnace. The optimal parameters for obtaining high-quality fuel briquettes have been determined. The introduction of a modifying additive into the oil residues makes it possible to obtain a binder composition for briquetting brown coal. Studies of the physical parameters of briquettes and the data of SEM showed that the thickness of the adsorption layer of coal and the cohesion of the binder in thin layers play an important role in the formation of the structure and strength of the briquette. It was assumed that at the optimum thickness of the film layer, the maximum manifestation of capillary forces and an increase in the adhesive interaction between the particles and the binder take place. The organic component of the coal fines is a mixture of various X-ray amorphous components, the presence and number of which vary in a series of metamorphism. The results of the performed studies show the possibility and prospects of using local raw materials for the development of high-quality briquetted brown coal fuel.
dc.format.extent126-132
dc.format.pages7
dc.identifier.citationHeydari S. A Green and Efficient Solvent- and Catalyst-Free Ultrasonic Dibenzylation Procedure / Somayyeh Heydari, Davood Habibi, Alireza Faraji // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2022. — Vol 16. — No 1. — P. 126–132.
dc.identifier.citationenHeydari S. A Green and Efficient Solvent- and Catalyst-Free Ultrasonic Dibenzylation Procedure / Somayyeh Heydari, Davood Habibi, Alireza Faraji // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2022. — Vol 16. — No 1. — P. 126–132.
dc.identifier.doidoi.org/10.23939/chcht16.01.126
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/60949
dc.language.isoen
dc.publisherВидавництво Львівської політехніки
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofChemistry & Chemical Technology, 1 (16), 2022
dc.relation.references[1] Anand, Ch.; Priya, S.V.; Lawrence, G.;Dhawale, D.S.;Varghese, S.;Wahab, M.A.;Prasad, K.S.; Vinu, A. Cage Type Mesoporous Ferrosilicate Catalysts with 3D Structure for Benzylation of Aromatics.Catal. Today2013, 204, 125-131. https://doi.org/10.1016/j.cattod.2012.08.010
dc.relation.references[2] Wang, H.; Ma, Y.; Tian, H.;Yu, A.;Chang, J.; Wu, Y. TetrabutylAmmonium Bromide-Mediated Benzylation of Phenols in Water under Mild Condition.Tetrahedron2014, 70, 2669-2673. https://doi.org/10.1016/j.tet.2014.01.004
dc.relation.references[3] Cuong, N.D.;Hoa, N.D.;Hoa, T.T.;Khieu, D.Q.;Quang, D.T.;Quang, V.V.; Hieu, N.V.NanoporousHematite Nanoparticles: Synthesis and Applications for Benzylation of Benzene and Aromatic Compounds.J. Alloy. Compd. 2014, 582, 83-87. https://doi.org/10.1016/j.jallcom.2013.08.057
dc.relation.references[4] Saxena, S.K.;Viswanadham,N. Enhanced Catalytic Properties of Mesoporous Mordenite for Benzylation of Benzene with Benzyl Alcohol.Appl. Surf. Sci. 2017, 392, 384-390. https://doi.org/10.1016/j.apsusc.2016.09.062
dc.relation.references[5] Yuan, B.; Li, Y.; Wang, Z.; Yu, F.;Xie, C.; Yu, S. A Novel Brønsted-Lewis Acidic Catalyst Based on Heteropoly Phosphotungstates: Synthesis and Catalysis in Benzylation of p-Xylene with Benzyl Alcohol.Mol. Catal. 2017, 443, 110-116. https://doi.org/10.1016/j.mcat.2017.10.003
dc.relation.references[6] Bhadra, K.H.; Yadav, G.D. Atom Economical Benzylation of Phenol with Benzyl Alcohol Using 20 % (w/w)Cs2.5H0.5PW12O40 Supported on Mesocellular Foam Silica (MCF) and its Kinetics.Micropor. Mesopor. Mat. 2018, 263, 190-200. https://doi.org/10.1016/j.micromeso.2017.12.017
dc.relation.references[7] Pu, X.;Su, Y. Heterogeneous Catalysis in Microreactors with Nanofluids for Fine Chemicals Syntheses: Benzylation of Toluene with Benzyl Chloride over Silica-Immobilized FeCl3 Catalyst.Chem. Eng. Sci. 2018, 184, 200-208. https://doi.org/10.1016/j.ces.2018.03.049
dc.relation.references[8] Nair, D.S.; Kurian, M. Highly Selective Synthesis of Diphenyl Methane via Liquid Phase Benzylation of Benzene over Cobalt Doped Zinc Nanoferrite Catalysts at Mild Conditions.J. Saudi Chem. Soc. 2019, 23, 127-132. https://doi.org/10.1016/j.jscs.2018.05.011
dc.relation.references[9] Mishra, K.; Lee, Y.R. Highly Synergistic Effect of Bifunctional Ru-rGO Catalyst for Enhanced Hydrogenative-Reductive Benzylation of N-Heteroaromatics.J. Catal. 2019, 376, 77-86. https://doi.org/10.1016/j.jcat.2019.06.052
dc.relation.references[10] Dar, B.A.;Shrivastava, V.;Bowmik, A.;Wagay, M.A.; Singh, B. An Expeditious N,N-Dibenzylation of Anilines under Ultrasonic Irradiation Conditions Using Low Loading Cu(II)-Clay Heterogeneous Catalyst.Tetrahedron Lett. 2014, 56, 136-141. https://doi.org/10.1016/j.tetlet.2014.11.044
dc.relation.references[11] Fueno, T.; Okamoto, H.; Tsuruta, T.; Furukawa, J. Quaternary Ammonium Salt as Initiator for Vinyl Polymerization.J. Polym. Sci. 1959, 36, 407-420. https://doi.org/10.1002/pol.1959.1203613034
dc.relation.references[12] Gupta, M.; Paul, S.; Gupta, R. SiO2-Cu2O: An Efficient and Recyclable Heterogeneous Catalyst for N-Benzylation of Primary and Secondary Amines.Chinese J. Catal. 2014, 35, 444-450. https://doi.org/10.1016/S1872-2067(14)60009-7
dc.relation.references[13] Major,R.T.CatalyticReduction of Mixtures of Para-Nitro- and Nitrosophenols with Aldehydes and Ketones. J. Am. Chem. Soc.1931, 53, 1901-1908. https://doi.org/10.1021/ja01356a042
dc.relation.references[14] Hayat, S.; Atta-ur-Rahman; Choudhary, M.I.;Khan, K.M.;Schumann, W.; Bayer, E.N-Alkylation of Anilines, Carboxamides and Several Nitrogen Heterocycles Using CsF–Celite/Alkyl Halides/CH3CN Combination.Tetrahedron2001, 57, 9951-9957. https://doi.org/10.1016/S0040-4020(01)00989-9
dc.relation.references[15] Leoppky, R.N.;Tomasik, W.Stereoelectronic Effects in Tertiary Amine Nitrosation: Nitrosative Cleavage vs. Aryl Ring Nitration.J. Org. Chem. 1983, 48, 2751-2757. https://doi.org/10.1021/jo00164a023
dc.relation.references[16] Saitoh, T.; Ichikawa, J. Bis(triarylmethylium)-Mediated Diaryl Ether Synthesis:  Oxidative Arylation of Phenols with N,N-Dialkyl-4-phenylthioanilines.J. Am. Chem. Soc. 2005, 127, 9696-9697. https://doi.org/10.1021/ja051839n
dc.relation.references[17] Li, Ch.; Wan, K.-F.; Guo, F.-Y.; Wu, Q.-H.; Yuan, M.-L.; Li, R.-X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H. Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions.J. Org Chem. 2019, 84, 2158-2168. https://doi.org/10.1021/acs.joc.8b03137
dc.relation.references[18] Noori, S.;Ghorbani-Vaghei, R.; Mirzaei-Mosbat, M.N-Benzylation of Primary Amines Using Magnetic Fe3O4 Nanoparticles Functionalized with Hexamethylenetetramine as an Efficient and Recyclable Heterogeneous Catalyst.J. Mol. Struct. 2020, 1219, 128583. https://doi.org/10.1016/j.molstruc.2020.128583
dc.relation.references[19] Peng, Q.; Zhang, Y.; Shi, F.; Deng, Y. Fe2O3-Supported Nano-Gold Catalyzed One-Pot Synthesis of N-Alkylated Anilines from Nitroarenes and Alcohols.Chem. Commun. 2011, 47, 6476-6478. https://doi.org/10.1039/c1cc11057h
dc.relation.references[20] Safaei-Ghomi, J.;Nazemzadeh, S.H.;Shahbazi-Alavi, H. Preparation and Characterization of Fe3O4@SiO2/APTPOSS Core–Shell Composite Nanomagnetics as a Novel Family of Reusable Catalysts and Their Application in the One-Pot Synthesis of 1,3-Thiazolidin-4-one Derivatives.Appl. Organometal Chem. 2016, 30, 911-916. https://doi.org/10.1002/aoc.3520
dc.relation.references[21] Eddingsaas, N.;Suslick, K. Light from Sonication of Crystal Slurries.Nature2006, 444, 163. https://doi.org/10.1038/444163a
dc.relation.references[22] Khaligh, N.G., Shirini, F.N-Sulfonic Acid Poly(4-vinylpyridinium) Hydrogen Sulfate as an Efficient and Reusable Solid Acid Catalyst for One-Pot Synthesis of Xanthene Derivatives in Dry Media under Ultrasound Irradiation.Ultrason. Sonochem. 2015, 22, 397-403. https://doi.org/10.1016/j.ultsonch.2014.06.020
dc.relation.references[23] Ramazani, A.; Rouhani, M.;Joo, S.W. Catalyst-Free Sonosynthesis of Highly Substituted Propanamide Derivatives in Water.Ultrason. Sonochem. 2016, 28, 393-399. https://doi.org/10.1016/j.ultsonch.2015.08.019
dc.relation.referencesen[1] Anand, Ch.; Priya, S.V.; Lawrence, G.;Dhawale, D.S.;Varghese, S.;Wahab, M.A.;Prasad, K.S.; Vinu, A. Cage Type Mesoporous Ferrosilicate Catalysts with 3D Structure for Benzylation of Aromatics.Catal. Today2013, 204, 125-131. https://doi.org/10.1016/j.cattod.2012.08.010
dc.relation.referencesen[2] Wang, H.; Ma, Y.; Tian, H.;Yu, A.;Chang, J.; Wu, Y. TetrabutylAmmonium Bromide-Mediated Benzylation of Phenols in Water under Mild Condition.Tetrahedron2014, 70, 2669-2673. https://doi.org/10.1016/j.tet.2014.01.004
dc.relation.referencesen[3] Cuong, N.D.;Hoa, N.D.;Hoa, T.T.;Khieu, D.Q.;Quang, D.T.;Quang, V.V.; Hieu, N.V.NanoporousHematite Nanoparticles: Synthesis and Applications for Benzylation of Benzene and Aromatic Compounds.J. Alloy. Compd. 2014, 582, 83-87. https://doi.org/10.1016/j.jallcom.2013.08.057
dc.relation.referencesen[4] Saxena, S.K.;Viswanadham,N. Enhanced Catalytic Properties of Mesoporous Mordenite for Benzylation of Benzene with Benzyl Alcohol.Appl. Surf. Sci. 2017, 392, 384-390. https://doi.org/10.1016/j.apsusc.2016.09.062
dc.relation.referencesen[5] Yuan, B.; Li, Y.; Wang, Z.; Yu, F.;Xie, C.; Yu, S. A Novel Brønsted-Lewis Acidic Catalyst Based on Heteropoly Phosphotungstates: Synthesis and Catalysis in Benzylation of p-Xylene with Benzyl Alcohol.Mol. Catal. 2017, 443, 110-116. https://doi.org/10.1016/j.mcat.2017.10.003
dc.relation.referencesen[6] Bhadra, K.H.; Yadav, G.D. Atom Economical Benzylation of Phenol with Benzyl Alcohol Using 20 % (w/w)Cs2.5H0.5PW12O40 Supported on Mesocellular Foam Silica (MCF) and its Kinetics.Micropor. Mesopor. Mat. 2018, 263, 190-200. https://doi.org/10.1016/j.micromeso.2017.12.017
dc.relation.referencesen[7] Pu, X.;Su, Y. Heterogeneous Catalysis in Microreactors with Nanofluids for Fine Chemicals Syntheses: Benzylation of Toluene with Benzyl Chloride over Silica-Immobilized FeCl3 Catalyst.Chem. Eng. Sci. 2018, 184, 200-208. https://doi.org/10.1016/j.ces.2018.03.049
dc.relation.referencesen[8] Nair, D.S.; Kurian, M. Highly Selective Synthesis of Diphenyl Methane via Liquid Phase Benzylation of Benzene over Cobalt Doped Zinc Nanoferrite Catalysts at Mild Conditions.J. Saudi Chem. Soc. 2019, 23, 127-132. https://doi.org/10.1016/j.jscs.2018.05.011
dc.relation.referencesen[9] Mishra, K.; Lee, Y.R. Highly Synergistic Effect of Bifunctional Ru-rGO Catalyst for Enhanced Hydrogenative-Reductive Benzylation of N-Heteroaromatics.J. Catal. 2019, 376, 77-86. https://doi.org/10.1016/j.jcat.2019.06.052
dc.relation.referencesen[10] Dar, B.A.;Shrivastava, V.;Bowmik, A.;Wagay, M.A.; Singh, B. An Expeditious N,N-Dibenzylation of Anilines under Ultrasonic Irradiation Conditions Using Low Loading Cu(II)-Clay Heterogeneous Catalyst.Tetrahedron Lett. 2014, 56, 136-141. https://doi.org/10.1016/j.tetlet.2014.11.044
dc.relation.referencesen[11] Fueno, T.; Okamoto, H.; Tsuruta, T.; Furukawa, J. Quaternary Ammonium Salt as Initiator for Vinyl Polymerization.J. Polym. Sci. 1959, 36, 407-420. https://doi.org/10.1002/pol.1959.1203613034
dc.relation.referencesen[12] Gupta, M.; Paul, S.; Gupta, R. SiO2-Cu2O: An Efficient and Recyclable Heterogeneous Catalyst for N-Benzylation of Primary and Secondary Amines.Chinese J. Catal. 2014, 35, 444-450. https://doi.org/10.1016/S1872-2067(14)60009-7
dc.relation.referencesen[13] Major,R.T.CatalyticReduction of Mixtures of Para-Nitro- and Nitrosophenols with Aldehydes and Ketones. J. Am. Chem. Soc.1931, 53, 1901-1908. https://doi.org/10.1021/ja01356a042
dc.relation.referencesen[14] Hayat, S.; Atta-ur-Rahman; Choudhary, M.I.;Khan, K.M.;Schumann, W.; Bayer, E.N-Alkylation of Anilines, Carboxamides and Several Nitrogen Heterocycles Using CsF–Celite/Alkyl Halides/CH3CN Combination.Tetrahedron2001, 57, 9951-9957. https://doi.org/10.1016/S0040-4020(01)00989-9
dc.relation.referencesen[15] Leoppky, R.N.;Tomasik, W.Stereoelectronic Effects in Tertiary Amine Nitrosation: Nitrosative Cleavage vs. Aryl Ring Nitration.J. Org. Chem. 1983, 48, 2751-2757. https://doi.org/10.1021/jo00164a023
dc.relation.referencesen[16] Saitoh, T.; Ichikawa, J. Bis(triarylmethylium)-Mediated Diaryl Ether Synthesis:  Oxidative Arylation of Phenols with N,N-Dialkyl-4-phenylthioanilines.J. Am. Chem. Soc. 2005, 127, 9696-9697. https://doi.org/10.1021/ja051839n
dc.relation.referencesen[17] Li, Ch.; Wan, K.-F.; Guo, F.-Y.; Wu, Q.-H.; Yuan, M.-L.; Li, R.-X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H. Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions.J. Org Chem. 2019, 84, 2158-2168. https://doi.org/10.1021/acs.joc.8b03137
dc.relation.referencesen[18] Noori, S.;Ghorbani-Vaghei, R.; Mirzaei-Mosbat, M.N-Benzylation of Primary Amines Using Magnetic Fe3O4 Nanoparticles Functionalized with Hexamethylenetetramine as an Efficient and Recyclable Heterogeneous Catalyst.J. Mol. Struct. 2020, 1219, 128583. https://doi.org/10.1016/j.molstruc.2020.128583
dc.relation.referencesen[19] Peng, Q.; Zhang, Y.; Shi, F.; Deng, Y. Fe2O3-Supported Nano-Gold Catalyzed One-Pot Synthesis of N-Alkylated Anilines from Nitroarenes and Alcohols.Chem. Commun. 2011, 47, 6476-6478. https://doi.org/10.1039/P.1cc11057h
dc.relation.referencesen[20] Safaei-Ghomi, J.;Nazemzadeh, S.H.;Shahbazi-Alavi, H. Preparation and Characterization of Fe3O4@SiO2/APTPOSS Core–Shell Composite Nanomagnetics as a Novel Family of Reusable Catalysts and Their Application in the One-Pot Synthesis of 1,3-Thiazolidin-4-one Derivatives.Appl. Organometal Chem. 2016, 30, 911-916. https://doi.org/10.1002/aoc.3520
dc.relation.referencesen[21] Eddingsaas, N.;Suslick, K. Light from Sonication of Crystal Slurries.Nature2006, 444, 163. https://doi.org/10.1038/444163a
dc.relation.referencesen[22] Khaligh, N.G., Shirini, F.N-Sulfonic Acid Poly(4-vinylpyridinium) Hydrogen Sulfate as an Efficient and Reusable Solid Acid Catalyst for One-Pot Synthesis of Xanthene Derivatives in Dry Media under Ultrasound Irradiation.Ultrason. Sonochem. 2015, 22, 397-403. https://doi.org/10.1016/j.ultsonch.2014.06.020
dc.relation.referencesen[23] Ramazani, A.; Rouhani, M.;Joo, S.W. Catalyst-Free Sonosynthesis of Highly Substituted Propanamide Derivatives in Water.Ultrason. Sonochem. 2016, 28, 393-399. https://doi.org/10.1016/j.ultsonch.2015.08.019
dc.relation.urihttps://doi.org/10.1016/j.cattod.2012.08.010
dc.relation.urihttps://doi.org/10.1016/j.tet.2014.01.004
dc.relation.urihttps://doi.org/10.1016/j.jallcom.2013.08.057
dc.relation.urihttps://doi.org/10.1016/j.apsusc.2016.09.062
dc.relation.urihttps://doi.org/10.1016/j.mcat.2017.10.003
dc.relation.urihttps://doi.org/10.1016/j.micromeso.2017.12.017
dc.relation.urihttps://doi.org/10.1016/j.ces.2018.03.049
dc.relation.urihttps://doi.org/10.1016/j.jscs.2018.05.011
dc.relation.urihttps://doi.org/10.1016/j.jcat.2019.06.052
dc.relation.urihttps://doi.org/10.1016/j.tetlet.2014.11.044
dc.relation.urihttps://doi.org/10.1002/pol.1959.1203613034
dc.relation.urihttps://doi.org/10.1016/S1872-2067(14)60009-7
dc.relation.urihttps://doi.org/10.1021/ja01356a042
dc.relation.urihttps://doi.org/10.1016/S0040-4020(01)00989-9
dc.relation.urihttps://doi.org/10.1021/jo00164a023
dc.relation.urihttps://doi.org/10.1021/ja051839n
dc.relation.urihttps://doi.org/10.1021/acs.joc.8b03137
dc.relation.urihttps://doi.org/10.1016/j.molstruc.2020.128583
dc.relation.urihttps://doi.org/10.1039/c1cc11057h
dc.relation.urihttps://doi.org/10.1002/aoc.3520
dc.relation.urihttps://doi.org/10.1038/444163a
dc.relation.urihttps://doi.org/10.1016/j.ultsonch.2014.06.020
dc.relation.urihttps://doi.org/10.1016/j.ultsonch.2015.08.019
dc.rights.holder© Національний університет “Львівська політехніка”, 2022
dc.rights.holder© Heydari S., Habibi D., Faraji A., 2022
dc.subjectN
dc.subjectN-дибензилування
dc.subjectароматичні аміни
dc.subjectопромінення ультразвуком
dc.subjectреакції без розчинників та каталізаторів
dc.subjectкімнатна температура
dc.subjectN
dc.subjectN-dibenzylation
dc.subjectaromatic amines
dc.subjectultrasound irradiation
dc.subjectsolvent and catalyst-free reactions
dc.subjectroom temperature
dc.titleA Green and Efficient Solvent- and Catalyst-Free Ultrasonic Dibenzylation Procedure
dc.title.alternative«Зелена» і ефективна процедура ультразвукового дибензилування, без розчинників і каталізаторів
dc.typeArticle

Files

Original bundle
Now showing 1 - 2 of 2
No Thumbnail Available
Name:
2022v16n1_Heydari_S-A_Green_and_Efficient_Solvent_126-132.pdf
Size:
677.8 KB
Format:
Adobe Portable Document Format
Download
No Thumbnail Available
Name:
2022v16n1_Heydari_S-A_Green_and_Efficient_Solvent_126-132__COVER.png
Size:
535.12 KB
Format:
Portable Network Graphics
Download
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.78 KB
Format:
Plain Text
Description:
Download

Collections

Chemistry & Chemical Technology. – 2022. – Vol. 16, No. 1