Ben Ayed, Emna; Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers, University of Mons, Place du Parc 23, Mons 7000, Belgium
Delcorps, Juliette ; Université de Mons - UMONS > Faculté des Sciences > Service des Matériaux Polymères et Composites
COULEMBIER, Olivier ; Université de Mons - UMONS > Faculté des Sciences > Service des Matériaux Polymères et Composites
Language :
English
Title :
Solvent-Free Iodination of Polyethylene via Twin-Screw Extrusion: A Scalable Approach
Lex, T. R.; Brummel, B. R.; Attia, M. F.; Giambalvo, L. N.; Lee, K. G.; Van Horn, B. A.; Whitehead, D. C.; Alexis, F. Iodinated Polyesters with Enhanced X-Ray Contrast Properties for Biomedical Imaging. Sci. Rep. 2020, 10 ( 1), 1508, 10.1038/s41598-020-57720-5
Kim, Y. K. The Use of Polyolefins in Industrial and Medical Applications. In Polyolefin Fibres; Elsevier, 2017; pp 135- 155. 10.1016/B978-0-08-101132-4.00005-9.
Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Selective Intermolecular Carbon-Hydrogen Bond Activation by Synthetic Metal Complexes in Homogeneous Solution. Acc. Chem. Res. 1995, 28 ( 3), 154- 162, 10.1021/ar00051a009
Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions. Acc. Chem. Res. 2012, 45 ( 6), 788- 802, 10.1021/ar200185g
Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals. Angew. Chem., Int. Ed. 2012, 51 ( 36), 8960- 9009, 10.1002/anie.201201666
Gutekunst, W. R.; Baran, P. S. C-H Functionalization Logic in Total Synthesis. Chem. Soc. Rev. 2011, 40 ( 4), 1976, 10.1039/c0cs00182a
Davies, H. M. L.; Morton, D. Recent Advances in C-H Functionalization. J. Org. Chem. 2016, 81 ( 2), 343- 350, 10.1021/acs.joc.5b02818
Hartwig, J. F.; Larsen, M. A. Undirected, Homogeneous C-H Bond Functionalization: Challenges and Opportunities. ACS Cent. Sci. 2016, 2 ( 5), 281- 292, 10.1021/acscentsci.6b00032
Shilov, A. E. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Catalysis by Metal Complexes; Springer Dordrecht: Netherlands, 1984.
Davies, H. M. L.; Manning, J. R. Catalytic C-H Functionalization by Metal Carbenoid and Nitrenoid Insertion. Nature 2008, 451 ( 7177), 417- 424, 10.1038/nature06485
Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Catalytic Carbene Insertion into C-H Bonds. Chem. Rev. 2010, 110 ( 2), 704- 724, 10.1021/cr900239n
Crabtree, R. H. Alkane C-H Activation and Functionalization with Homogeneous Transition Metal Catalysts: A Century of Progress─a New Millennium in Prospect. J. Chem. Soc., Dalton Trans. 2001, 17, 2437- 2450, 10.1039/b103147n
Breslow, R.; Gellman, S. H. Tosylamidation of Cyclohexane by a Cytochrome P-450 Model. J. Chem. Soc. Chem. Commun. 1982, 24, 1400, 10.1039/c39820001400
Groves, J. T.; Nemo, T. E.; Myers, R. S. Hydroxylation and Epoxidation Catalyzed by Iron-Porphine Complexes. Oxygen Transfer from Iodosylbenzene. J. Am. Chem. Soc. 1979, 101 ( 4), 1032- 1033, 10.1021/ja00498a040
Goswami, M.; de Bruin, B. Metal-Catalysed Azidation of Organic Molecules. Eur. J. Org. Chem. 2017, 2017 ( 8), 1152- 1176, 10.1002/ejoc.201601390
Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssié, P. Transition-Metal-Catalysed Reactions of Diazoesters. Insertion into C-H Bonds of Paraffins Catalysed by Bulky Rhodium(II) Carboxylates: Enhanced Attack on Primary C-H Bonds. Bull. Sociétés Chim. Belg. 1984, 93 ( 11), 945- 948, 10.1002/bscb.19840931103
Crabtree, R. H.; Mihelcic, J. M.; Quirk, J. M. Iridium Complexes in Alkane Dehydrogenation. J. Am. Chem. Soc. 1979, 101 ( 26), 7738- 7740, 10.1021/ja00520a030
Russell, G. A.; Brown, H. C. The Competitive Halogenation of Cyclohexane and Aralkyl Hydrocarbons; Evidence as to the Nature of the Transition States in Halogenation Reactions 1,2. J. Am. Chem. Soc. 1955, 77 ( 17), 4578- 4582, 10.1021/ja01622a041
Liu, W.; Groves, J. T. Manganese Porphyrins Catalyze Selective C-H Bond Halogenations. J. Am. Chem. Soc. 2010, 132 ( 37), 12847- 12849, 10.1021/ja105548x
Bae, C.; Hartwig, J. F.; Boaen Harris, N. K.; Long, R. O.; Anderson, K. S.; Hillmyer, M. A. Catalytic Hydroxylation of Polypropylenes. J. Am. Chem. Soc. 2005, 127 ( 2), 767- 776, 10.1021/ja044440s
Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Thermal, Catalytic, Regiospecific Functionalization of Alkanes. Science 2000, 287 ( 5460), 1995- 1997, 10.1126/science.287.5460.1995
Schreiner, P. R.; Fokin, A. A. Selective Alkane C-H-bond Functionalizations Utilizing Oxidative Single-electron Transfer and Organocatalysis. Chem. Rec. 2004, 3 ( 5), 247- 257, 10.1002/tcr.10070
Fokin, A. A.; Schreiner, P. R. Metal-Free, Selective Alkane Functionalizations. Adv. Synth. Catal. 2003, 345 ( 9-10), 1035- 1052, 10.1002/adsc.200303049
Tu, H.; Zhu, S.; Qing, F.-L.; Chu, L. Visible-Light-Induced Halogenation of Aliphatic C H Bonds. Tetrahedron Lett. 2018, 59 ( 3), 173- 179, 10.1016/j.tetlet.2017.12.023
Roy, S.; Panja, S.; Sahoo, S. R.; Chatterjee, S.; Maiti, D. Enroute Sustainability: Metal Free C-H Bond Functionalisation. Chem. Soc. Rev. 2023, 52 ( 7), 2391- 2479, 10.1039/D0CS01466D
Radicals in Organic Synthesis, 1st ed.; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH, 2001. 10.1002/9783527618293.
Minisci, F.; Porta, O.; Recupero, F.; Gambarotti, C.; Paganelli, R.; Pedulli, G. F.; Fontana, F. New Free-Radical Halogenations of Alkanes, Catalysed by N-Hydroxyphthalimide. Polar and Enthalpic Effects on the Chemo- and Regioselectivity. Tetrahedron Lett. 2004, 45 ( 8), 1607- 1609, 10.1016/j.tetlet.2003.12.130
Amaoka, Y.; Kamijo, S.; Hoshikawa, T.; Inoue, M. Radical Amination of C(Sp 3)-H Bonds Using N -Hydroxyphthalimide and Dialkyl Azodicarboxylate. J. Org. Chem. 2012, 77 ( 22), 9959- 9969, 10.1021/jo301840e
Schmidt, V. A.; Quinn, R. K.; Brusoe, A. T.; Alexanian, E. J. Site-Selective Aliphatic C-H Bromination Using N -Bromoamides and Visible Light. J. Am. Chem. Soc. 2014, 136 ( 41), 14389- 14392, 10.1021/ja508469u
Quinn, R. K.; Könst, Z. A.; Michalak, S. E.; Schmidt, Y.; Szklarski, A. R.; Flores, A. R.; Nam, S.; Horne, D. A.; Vanderwal, C. D.; Alexanian, E. J. Site-Selective Aliphatic C-H Chlorination Using N -Chloroamides Enables a Synthesis of Chlorolissoclimide. J. Am. Chem. Soc. 2016, 138 ( 2), 696- 702, 10.1021/jacs.5b12308
Tierney, M. M.; Crespi, S.; Ravelli, D.; Alexanian, E. J. Identifying Amidyl Radicals for Intermolecular C-H Functionalizations. J. Org. Chem. 2019, 84 ( 20), 12983- 12991, 10.1021/acs.joc.9b01774
Fazekas, T. J.; Alty, J. W.; Neidhart, E. K.; Miller, A. S.; Leibfarth, F. A.; Alexanian, E. J. Diversification of Aliphatic C-H Bonds in Small Molecules and Polyolefins through Radical Chain Transfer. Science 2022, 375 ( 6580), 545- 550, 10.1126/science.abh4308
Czaplyski, W. L.; Na, C. G.; Alexanian, E. J. C-H Xanthylation: A Synthetic Platform for Alkane Functionalization. J. Am. Chem. Soc. 2016, 138 ( 42), 13854- 13857, 10.1021/jacs.6b09414
Artaryan, A.; Mardyukov, A.; Kulbitski, K.; Avigdori, I.; Nisnevich, G. A.; Schreiner, P. R.; Gandelman, M. Aliphatic C-H Bond Iodination by a N -Iodoamide and Isolation of an Elusive N -Amidyl Radical. J. Org. Chem. 2017, 82 ( 14), 7093- 7100, 10.1021/acs.joc.7b00557
Schreiner, P. R.; Lauenstein, O.; Butova, E. D.; Fokin, A. A. The First Efficient Iodination of Unactivated Aliphatic Hydrocarbons. Angew. Chem., Int. Ed. 1999, 38 ( 18), 2786- 2788, 10.1002/(SICI)1521-3773(19990917)38:18<2786::AID-ANIE2786>3.0.CO;2-0
Liguori, L.; Bjørsvik, H.-R.; Bravo, A.; Fontana, F.; Minisci, F. A New Direct Homolytic Iodination Reaction of Alkanes by Perfluoroalkyl Iodides. Chem. Commun. 1997, 1501- 1502, 10.1039/a703332j
Montoro, R.; Wirth, T. Direct Iodination of Alkanes. Org. Lett. 2003, 5 ( 24), 4729- 4731, 10.1021/ol0359012
Tanner, D. D.; Gidley, G. C. Free-Radical Iodination. A Novel Synthetic Method. J. Am. Chem. Soc. 1968, 90 ( 3), 808- 809, 10.1021/ja01005a056
Barluenga, J.; Campos-Gómez, E.; Rodríguez, D.; González-Bobes, F.; González, J. M. New Iodination Reactions of Saturated Hydrocarbons. Angew. Chem., Int. Ed. 2005, 44 ( 36), 5851- 5854, 10.1002/anie.200501195
Combe, S. H.; Hosseini, A.; Song, L.; Hausmann, H.; Schreiner, P. R. Catalytic Halogen Bond Activation in the Benzylic C-H Bond Iodination with Iodohydantoins. Org. Lett. 2017, 19 ( 22), 6156- 6159, 10.1021/acs.orglett.7b03034
Williamson, J. B.; Lewis, S. E.; Johnson, R. R.; Manning, I. M.; Leibfarth, F. A. C-H Functionalization of Commodity Polymers. Angew. Chem., Int. Ed. 2019, 58 ( 26), 8654- 8668, 10.1002/anie.201810970
Zhou, H.; Wang, S.; Huang, H.; Li, Z.; Plummer, C. M.; Wang, S.; Sun, W.-H.; Chen, Y. Direct Amination of Polyethylene by Metal-Free Reaction. Macromolecules 2017, 50 ( 9), 3510- 3515, 10.1021/acs.macromol.6b02572
Plummer, C. M.; Zhou, H.; Zhu, W.; Huang, H.; Liu, L.; Chen, Y. Mild Halogenation of Polyolefins Using an N -Haloamide Reagent. Polym. Chem. 2018, 9 ( 11), 1309- 1317, 10.1039/C8PY00013A
Cooper, G. D.; Prober, M. The Action of Oxygen Corona and of Ozone on Polyethylene. J. Polym. Sci. 1960, 44 ( 144), 397- 409, 10.1002/pol.1960.1204414411
Lehman, S. E.; Wagener, K. B.; Baugh, L. S.; Rucker, S. P.; Schulz, D. N.; Varma-Nair, M.; Berluche, E. Linear Copolymers of Ethylene and Polar Vinyl Monomers via Olefin Metathesis-Hydrogenation: Synthesis, Characterization, and Comparison to Branched Analogues. Macromolecules 2007, 40 ( 8), 2643- 2656, 10.1021/ma070085p
Holmes-Farley, S. R.; Reamey, R. H.; Nuzzo, R.; McCarthy, T. J.; Whitesides, G. M. Reconstruction of the Interface of Oxidatively Functionalized Polyethylene and Derivatives on Heating. Langmuir 1987, 3 ( 5), 799- 815, 10.1021/la00077a040
Shoji, A.; Adachi, T.; Tsuchiya, M.; Fujishima, M.; Kumar, D. S.; Yoshida, Y. Halogen Plasma Treatment of Polyethylene Surfaces. J. Photopolym. Sci. Technol. 2005, 18 ( 2), 251- 254, 10.2494/photopolymer.18.251
Fujishima, M.; Kawabata, D.; Funakoshi, C.; Yoshida, Y.; Yamashita, T.; Kashiwagi, K.; Higashikata, K. Effect of I2 Plasma on the Properties of Polyethylene. Polym. J. 1995, 27 ( 6), 575- 578, 10.1295/polymj.27.575
Williamson, J. B.; Czaplyski, W. L.; Alexanian, E. J.; Leibfarth, F. A. Regioselective C-H Xanthylation as a Platform for Polyolefin Functionalization. Angew. Chem. 2018, 130 ( 21), 6369- 6373, 10.1002/ange.201803020
Dully, J. H.; Wodarczyk, F. J.; Ratto, J. J. Preparation of Thin Films by Plasma Polymerization of Iodomethane. J. Polym. Sci. Part Polym. Chem. 1987, 25 ( 4), 1187- 1190, 10.1002/pola.1987.080250422
Munro, H. S.; Ward, R. J.; Khor, E. The Synthesis and XPS Characterization of Iodine Containing Plasma Polymers. J. Polym. Sci. Part Polym. Chem. 1990, 28 ( 4), 923- 929, 10.1002/pola.1990.080280417
Elman, J. F.; Gerenser, L. J.; Goppert-Berarducci, K. E.; Pochan, J. M. Kinetics of the Gas-Phase Halogenation of a Polyethylene Surface as Studied with x-Ray Photoelectron Spectroscopy. Macromolecules 1990, 23 ( 17), 3922- 3928, 10.1021/ma00219a010
Schreiner, P. R.; Lauenstein, O.; Kolomitsyn, I. V.; Nadi, S.; Fokin, A. A. Selective C-H Activation of Aliphatic Hydrocarbons under Phase-Transfer Conditions. Angew. Chem., Int. Ed. 1998, 37 ( 13-14), 1895- 1897, 10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A
Schreiner, P. R.; Lauenstein, O.; Butova, E. D.; Gunchenko, P. A.; Kolomitsin, I. V.; Wittkopp, A.; Feder, G.; Fokin, A. A. Selective Radical Reactions in Multiphase Systems: Phase-Transfer Halogenations of Alkanes. Chem. - Eur. J. 2001, 7 ( 23), 4996- 5003, 10.1002/1521-3765(20011203)7:23<4996::AID-CHEM4996>3.0.CO;2-P
Chmelar, J.; Matuska, P.; Gregor, T.; Bobak, M.; Fantinel, F.; Kosek, J. Softening of Polyethylene Powders at Reactor Conditions. Chem. Eng. J. 2013, 228, 907- 916, 10.1016/j.cej.2013.05.069
Dehmlow, E. V.; Lissel, M. Anwendungen Der Phasentransfer-Katalyse, 6: Nebenreaktionen Der Dihalogencarbenerzeugung Aus Haloform/Natronlauge/Katalysator. Chem. Ber. 1978, 111 ( 12), 3873- 3878, 10.1002/cber.19781111213
Aylward, G. H.; Findlay, T. J. Datensammlung Chemie in SI-Einheiten; John Wiley & Sons, 2014.
Dehmlow, E. V.; Lissel, M.; Heider, J. Anwendungen der phasentransfer-katalyse─4. Tetrahedron 1977, 33 ( 3), 363- 366, 10.1016/0040-4020(77)80121-X
Boz, E.; Wagener, K. B.; Ghosal, A.; Fu, R.; Alamo, R. G. Synthesis and Crystallization of Precision ADMET Polyolefins Containing Halogens. Macromolecules 2006, 39 ( 13), 4437- 4447, 10.1021/ma0605088
Watson, M. D.; Wagener, K. B. Functionalized Polyethylene via Acyclic Diene Metathesis Polymerization: Effect of Precise Placement of Functional Groups. Macromolecules 2000, 33 ( 24), 8963- 8970, 10.1021/ma0010332
Wang, X.; Wang, Y.; Shi, X.; Liu, J.; Chen, C.; Li, Y. Syntheses of Well-Defined Functional Isotactic Polypropylenes via Efficient Copolymerization of Propylene with ω-Halo-α-Alkenes by Post-Metallocene Hafnium Catalyst. Macromolecules 2014, 47 ( 2), 552- 559, 10.1021/ma4022696
Zhang, M.; Colby, R. H.; Milner, S. T.; Chung, T. C. M.; Huang, T.; deGroot, W. Synthesis and Characterization of Maleic Anhydride Grafted Polypropylene with a Well-Defined Molecular Structure. Macromolecules 2013, 46 ( 11), 4313- 4323, 10.1021/ma4006632
Moad, G. The Synthesis of Polyolefin Graft Copolymers by Reactive Extrusion. Prog. Polym. Sci. 1999, 24 ( 1), 81- 142, 10.1016/S0079-6700(98)00017-3
Gloor, P. E.; Tang, Y.; Kostanska, A. E.; Hamielec, A. E. Chemical Modification of Polyolefins by Free Radical Mechanisms: A Modelling and Experimental Study of Simultaneous Random Scission, Branching and Crosslinking. Polymer 1994, 35 ( 5), 1012- 1030, 10.1016/0032-3861(94)90946-6
Tripathi, D. Practical Guide to Polypropylene; iSmithers Rapra Publishing, 2002.
Gülsoy, H. Ö.; Taşdemır, M. Physical and Mechanical Properties of Polypropylene Reinforced with Fe Particles. Int. J. Polym. Mater. 2006, 55 ( 8), 619- 626, 10.1080/00914030500257664
Khafagy, R. M.; Badr, Y. A. In Situ FTIR Spectroscopic Study of the Recently Detected Low-temperature-induced Structural Changes in Isotactic Polypropylene. J. Polym. Sci., Part B: Polym. Phys. 2005, 43 ( 20), 2829- 2842, 10.1002/polb.20567