Scalable, safer and greener syntheses of vinylimidazoles via reactive distillation of hydroxyethylimidazole intermediates

Alshaikh, Ali; O'Harra, Kathryn E.; Liu, Xiaoyang; Whitley, John W.; Mittenthal, Max S.; Taylor, Wesley F.; Turner, C. Heath; Bara, Jason E.

doi:10.1002/pi.6161

Scalable, safer and greener syntheses of vinylimidazoles via reactive distillation of hydroxyethylimidazole intermediates

Journal Article · Fri Jan 01 04:00:00 EST 2021 · Polymer International

DOI:https://doi.org/10.1002/pi.6161· OSTI ID:1853544

^[1]; ^[2]; Liu, Xiaoyang ^[2]; Whitley, John W. ^[2]; Mittenthal, Max S. ^[2]; Taylor, Wesley F. ^[2]; Turner, C. Heath ^[2]; ^[2]

Department of Chemical &, Biological Engineering University of Alabama Tuscaloosa AL USA; OSTI
Department of Chemical &, Biological Engineering University of Alabama Tuscaloosa AL USA

Not provided.

Research Organization:: Univ. of South Alabama, Mobile, AL (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0020282

OSTI ID:: 1853544

Journal Information:: Polymer International, Journal Name: Polymer International Journal Issue: 5 Vol. 70; ISSN 0959-8103

Publisher:: Society of Chemical Industry

Country of Publication:: United States

Language:: English

References (55)

Synthesis of new imidazole derivatives as potential inhibitors of thromboxane synthetase Banfi, Aldo; Sala, Alberto; Soresinetti, P. Angelo Journal of Heterocyclic Chemistry, Vol. 27, Issue 2 https://doi.org/10.1002/jhet.5570270219	journal	February 1990
Tailoring macromolecular architecture with imidazole functionality: A perspective for controlled polymerization processes Green, Matthew D.; Allen, Michael H.; Dennis, Joseph M. European Polymer Journal, Vol. 47, Issue 4 https://doi.org/10.1016/j.eurpolymj.2010.09.035	journal	April 2011
Highly efficient flame retardant poly(lactic acid) using imidazole phosphate poly(ionic liquid) Li, Caixia; Ma, Chao; Li, Juan Polymers for Advanced Technologies, Vol. 31, Issue 8 https://doi.org/10.1002/pat.4903	journal	March 2020
Designing Imidazole-Based Ionic Liquids and Ionic Liquid Monomers for Emerging Technologies Green, Matthew D.; Long, Timothy E. Polymer Reviews, Vol. 49, Issue 4 https://doi.org/10.1080/15583720903288914	journal	October 2009
Controlled Radical Polymerization of 4-Vinylimidazole Allen, Michael H.; Hemp, Sean T.; Smith, Adam E. Macromolecules, Vol. 45, Issue 9 https://doi.org/10.1021/ma300543h	journal	April 2012
Imidazole-containing Polymers. Synthesis and Polymerization of the Monomer 4(5)-Vinylimidazole Overberger, C. G.; Vorchheimer, N. Journal of the American Chemical Society, Vol. 85, Issue 7 https://doi.org/10.1021/ja00890a026	journal	April 1963
Ueber Glyoxalin und seine Homologe Radzisewski, Br. Berichte der deutschen chemischen Gesellschaft, Vol. 15, Issue 2 https://doi.org/10.1002/cber.188201502245	journal	July 1882
Synthesis of 1,2-Dialkyl-, 1,4(5)-Dialkyl-, and 1,2,4(5)-Trialkylimidazoles via a One-Pot Method Hindman, Michelle S.; Stanton, Alexander D.; Irvin, A. Christopher Industrial & Engineering Chemistry Research, Vol. 52, Issue 34 https://doi.org/10.1021/ie401861b	journal	August 2013
Adsorption, permeation, and DFT studies of PVC/PVIm blends for separation of CO2/CH4 Noorani, Narmin; Mehrdad, Abbas Journal of Molecular Liquids, Vol. 292 https://doi.org/10.1016/j.molliq.2019.111410	journal	October 2019
Synthesis and characterization of amphiphilic diblock copolymers of 2-(1-imidazolyl)ethyl methacrylate and styrene Rikkou-Kalourkoti, Maria; Panteli, Panayiota A.; Patrickios, Costas S. Polymer Chemistry, Vol. 5, Issue 14 https://doi.org/10.1039/c4py00221k	journal	January 2014
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Preparation of Poly(1-vinylimidazole)-Grafted Magnetic Nanoparticles and Their Application for Removal of Metal Ions Takafuji, Makoto; Ide, Shunichi; Ihara, Hirotaka Chemistry of Materials, Vol. 16, Issue 10 https://doi.org/10.1021/cm030334y	journal	April 2004
Metal complexes with N-alkenylimidazoles: synthesis, structures, and biological activity Parshina, L. N.; Trofimov, B. A. Russian Chemical Bulletin, Vol. 60, Issue 4 https://doi.org/10.1007/s11172-011-0096-9	journal	April 2011
Removal of Hg(II) by poly(1-vinylimidazole)-grafted Fe3O4@SiO2 magnetic nanoparticles Shan, Chao; Ma, Zhiyao; Tong, Meiping Water Research, Vol. 69 https://doi.org/10.1016/j.watres.2014.11.030	journal	February 2015
Imidazole- and imidazolium-containing polymers for biology and material science applications Anderson, Emily B.; Long, Timothy E. Polymer, Vol. 51, Issue 12 https://doi.org/10.1016/j.polymer.2010.02.006	journal	May 2010
The Tautomeric Character of the Imidazole Ring Green, Harry; Day, Allan R. Journal of the American Chemical Society, Vol. 64, Issue 5 https://doi.org/10.1021/ja01257a047	journal	May 1942
2-Vinylimidazole and 1-Methyl-2-vinylimidazole Lawson, J. Keith Journal of the American Chemical Society, Vol. 75, Issue 14 https://doi.org/10.1021/ja01110a029	journal	July 1953
Removal of Hg(II) from acid aqueous solutions by poly(N-vinylimidazole) hydrogel Molina, M. J.; G�mez-Ant�n, M. R.; Rivas, B. L. Journal of Applied Polymer Science, Vol. 79, Issue 8 https://doi.org/10.1002/1097-4628(20010222)79:8<1467::AID-APP140>3.0.CO;2-9	journal	January 2000
Alkyl-Substituted N-Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities Green, Matthew D.; Salas-de la Cruz, David; Ye, Yuesheng Macromolecular Chemistry and Physics, Vol. 212, Issue 23 https://doi.org/10.1002/macp.201100389	journal	October 2011
The multicomponent Debus–Radziszewski reaction in macromolecular chemistry Saxer, S.; Marestin, C.; Mercier, R. Polymer Chemistry, Vol. 9, Issue 15 https://doi.org/10.1039/C8PY00173A	journal	January 2018
Free-Radical Polymerization of N -Vinylimidazole and Quaternized Vinylimidazole in Aqueous Solution Santanakrishnan, Sandhya; Hutchinson, Robin A. Macromolecular Chemistry and Physics, Vol. 214, Issue 10 https://doi.org/10.1002/macp.201300044	journal	April 2013
Synthesis and homopolymerization studies of vinylimidazolium salts Salamone, J. C.; Israel, S. C.; Taylor, P. Polymer, Vol. 14, Issue 12 https://doi.org/10.1016/0032-3861(73)90039-6	journal	December 1973
Poly(ionic liquid)s: An update Yuan, Jiayin; Mecerreyes, David; Antonietti, Markus Progress in Polymer Science, Vol. 38, Issue 7 https://doi.org/10.1016/j.progpolymsci.2013.04.002	journal	July 2013
Study of CO2 adsorption onto poly(1–vinylimidazole) using quartz crystal microbalance and density functional theory methods Mehrdad, Abbas; Noorani, Narmin Journal of Molecular Liquids, Vol. 291 https://doi.org/10.1016/j.molliq.2019.111288	journal	October 2019
Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way Trost, Barry M. Angewandte Chemie International Edition in English, Vol. 34, Issue 3 https://doi.org/10.1002/anie.199502591	journal	February 1995
Recent progress in controlled radical polymerization of N-vinyl monomers Nakabayashi, Kazuhiro; Mori, Hideharu European Polymer Journal, Vol. 49, Issue 10 https://doi.org/10.1016/j.eurpolymj.2013.07.006	journal	October 2013
Zwitterionic imidazolium compounds with high cathodic stability as additives for lithium battery electrolytes Nguyen, Dinh Quan; Bae, Hyun Woo; Jeon, Eun Hee Journal of Power Sources, Vol. 183, Issue 1 https://doi.org/10.1016/j.jpowsour.2008.04.047	journal	August 2008
Synthesis of Vinyl Monomers With Active Azaaromatic Groups. Phase-transfer Catalytic Approach Bogdal, Dariusz; Jaskot, Krzysztof Synthetic Communications, Vol. 30, Issue 18 https://doi.org/10.1080/00397910008086974	journal	September 2000
Synthesis and biological evaluation of di- and tri-substituted imidazoles as safer anti-inflammatory-antifungal agents Husain, Asif; Drabu, Sushma; Kumar, Nitin Journal of Pharmacy and Bioallied Sciences, Vol. 5, Issue 2 https://doi.org/10.4103/0975-7406.111822	journal	January 2013
Synthesis, Characterisation, and Reactivity of 1-(1-Methylimidazol-2-yl)ethenes Abarca-gonzalez, Belen; Jones, R. Alan; Medio-simon, Mercedes Synthetic Communications, Vol. 20, Issue 3 https://doi.org/10.1080/00397919008052772	journal	February 1990
The atom economy--a search for synthetic efficiency Trost, B. Science, Vol. 254, Issue 5037 https://doi.org/10.1126/science.1962206	journal	December 1991
Proton affinity of five-membered heterocyclic amines: Assessment of computational procedures Rao, J. Srinivasa; Sastry, G. Narahari International Journal of Quantum Chemistry, Vol. 106, Issue 5 https://doi.org/10.1002/qua.20862	journal	January 2006
Synthesis and Characterization of Alkylated Poly(1-vinylimidazole) to Control the Stability of its DNA Polyion Complexes for Gene Delivery Asayama, Shoichiro; Hakamatani, Tomoe; Kawakami, Hiroyoshi Bioconjugate Chemistry, Vol. 21, Issue 4 https://doi.org/10.1021/bc900411m	journal	April 2010
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/PhysRevA.38.3098	journal	September 1988
Syntheses of polyalkylated imidazoles Evjen, Sigvart; Fiksdahl, Anne Synthetic Communications, Vol. 47, Issue 15 https://doi.org/10.1080/00397911.2017.1330416	journal	June 2017
High Transfection Efficiency of Poly(4-vinylimidazole) as a New Gene Carrier Ihm, Jong-Eun; Han, Ki-Ok; Han, In-Kwon Bioconjugate Chemistry, Vol. 14, Issue 4 https://doi.org/10.1021/bc025611q	journal	May 2003
Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena Klamt, Andreas The Journal of Physical Chemistry, Vol. 99, Issue 7 https://doi.org/10.1021/j100007a062	journal	February 1995
Metal ion binding properties of poly(N-vinylimidazole) hydrogels Rivas, Bernab� L.; Maturana, Hern�n A.; Molina, M. Jes�s Journal of Applied Polymer Science, Vol. 67, Issue 6 https://doi.org/10.1002/(SICI)1097-4628(19980207)67:6<1109::AID-APP19>3.0.CO;2-V	journal	February 1998
Green Chemistry: Principles and Practice Anastas, Paul; Eghbali, Nicolas Chem. Soc. Rev., Vol. 39, Issue 1 https://doi.org/10.1039/B918763B	journal	January 2010
The mechanism of the stereoregular polymerization of 2-vinylimidazole and 2-vinylbenzimidazole Lando, J. B.; Litt, M.; Shimko, T. Polymer Engineering and Science, Vol. 16, Issue 5 https://doi.org/10.1002/pen.760160515	journal	May 1976
Vinylierung Reppe, Walter Justus Liebigs Annalen der Chemie, Vol. 601, Issue 1 https://doi.org/10.1002/jlac.19566010106	journal	December 1956
Ueber die Einwirkung des Ammoniaks auf Glyoxal Debus, Heinrich Annalen der Chemie und Pharmacie, Vol. 107, Issue 2 https://doi.org/10.1002/jlac.18581070209	journal	January 1858
DFT study on the effect of exocyclic substituents on the proton affinity of 1-methylimidazole Liu, Haining; Bara, Jason E.; Turner, C. Heath Chemical Physics, Vol. 416 https://doi.org/10.1016/j.chemphys.2013.02.029	journal	April 2013
Metal-Salt Enhanced Grafting of Vinylpyridine and Vinylimidazole Monomer Combinations in Radiation Grafted Membranes for High-Temperature PEM Fuel Cells Rajabalizadeh Mojarrad, Naeimeh; Sadeghi, Sahl; Yarar Kaplan, Begüm ACS Applied Energy Materials, Vol. 3, Issue 1 https://doi.org/10.1021/acsaem.9b01777	journal	December 2019
Fabrication of a shape memory hydrogel based on imidazole–zinc ion coordination for potential cell-encapsulating tubular scaffold application Nan, Wenjing; Wang, Wei; Gao, Han Soft Matter, Vol. 9, Issue 1 https://doi.org/10.1039/C2SM26918J	journal	January 2013
Imidazolium Salt-Incorporated Postcross-Linked Porous Polymers for Efficient Adsorption of Rhodamine B and Cd ²⁺ from Aqueous Solution Wang, Xiaomei; Liu, Zhen; Zhou, Fa Journal of Chemical & Engineering Data, Vol. 65, Issue 4 https://doi.org/10.1021/acs.jced.9b01090	journal	February 2020
Synthesis and characterization of 4-vinylimidazole ABA triblock copolymers utilizing a difunctional RAFT chain transfer agent Allen, Michael H.; Hemp, Sean T.; Zhang, Musan Polymer Chemistry, Vol. 4, Issue 7 https://doi.org/10.1039/c3py00043e	journal	January 2013
Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction Becke, Axel D. The Journal of Chemical Physics, Vol. 96, Issue 3 https://doi.org/10.1063/1.462066	journal	February 1992
Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones Yamaguchi, Masahisa; Kamei, Kenshi; Koga, Takaki Journal of Medicinal Chemistry, Vol. 36, Issue 25 https://doi.org/10.1021/jm00077a008	journal	December 1993
Synthesis of Imidazole-Based Medicinal Molecules Utilizing the van Leusen Imidazole Synthesis Zheng, Xunan; Ma, Zhengning; Zhang, Dawei Pharmaceuticals, Vol. 13, Issue 3 https://doi.org/10.3390/ph13030037	journal	March 2020
Synthesis and Aqueous Solution Characterization of Catalytically Active Block Copolymers Containing Imidazole Simmons, Martin R.; Patrickios, Costas S. Macromolecules, Vol. 31, Issue 25 https://doi.org/10.1021/ma980351m	journal	December 1998
New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles Kerhervé, Jennifer; Botuha, Candice; Dubois, Joëlle Organic & Biomolecular Chemistry, Vol. 7, Issue 10 https://doi.org/10.1039/b902601k	journal	January 2009
Flexible and Washable Poly(Ionic Liquid) Nanofibrous Membrane with Moisture Proof Pressure Sensing for Real-Life Wearable Electronics Wang, Zehong; Si, Yang; Zhao, Cunyi ACS Applied Materials & Interfaces, Vol. 11, Issue 30 https://doi.org/10.1021/acsami.9b07786	journal	July 2019
Density-functional approximation for the correlation energy of the inhomogeneous electron gas Perdew, John P. Physical Review B, Vol. 33, Issue 12 https://doi.org/10.1103/PhysRevB.33.8822	journal	June 1986
Molecular Force Field for Ionic Liquids Composed of Triflate or Bistriflylimide Anions Canongia Lopes, José N.; Pádua, Agílio A. H. The Journal of Physical Chemistry B, Vol. 108, Issue 43 https://doi.org/10.1021/jp0476545	journal	October 2004

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