Continuous ARGET ATRP of methyl methacrylate and butyl acrylate in a stirred tank reactor

Industrial and Engineering Chemistry Research

Volumn 52, Issue 34, 2013, Pages 11931-11942

  Chan, Nicky ^a   Meuldijk, Jan ^b   Cunningham, Michael F ^a   Hutchinson, Robin A ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BATCH POLYMERIZATIONS; CONTINUOUS STIRRED TANK REACTOR; CONTROLLED RADICAL POLYMERIZATION; METHYL METHACRYLATES; POLYMER CHAIN EXTENSION; POLYMERIZATION RATES; STEADY-STATE BEHAVIORS; STIRRED TANK REACTORS;

ACRYLIC MONOMERS; ATOM TRANSFER RADICAL POLYMERIZATION; BATCH DATA PROCESSING; CHAINS; CHEMICAL ACTIVATION; COPPER; ESTERS; POLYMERIZATION;

COPPER COMPOUNDS;

EID: 84883369794     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie4011996     Document Type: Article

References (36)

1. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Polymerization of Methyl Methacrylate with the Carbon Tetrachloride/ Dichlorotris(triphenylphosphine)ruthenium(II)/Methylaluminum Bis(2,6-di-tert -butylphenoxide) Initiating System: Possibility of Living Radical Polymerization Macromolecules 1995, 28, 1721
2. Wang, J. S.; Matyjaszewski, K. Controlled/"Living" Radical Polymerization. Atom Transfer Radical Polymerization in the Presence of Transition-Metal Complexes J. Am. Chem. Soc. 1995, 117, 5614
3. Matyjaszewski, K.; Xia, J. Atom Transfer Radical Polymerization Chem. Rev. 2001, 101, 2921
4. Ouchi, M.; Terashima, T.; Sawamoto, M. Transition-Metal-Catalyzed Living Radical Polymerization: Toward Perfection in Catalysis and Precision Polymer Synthesis Chem. Rev. 2009, 109, 4963
5. Tsarevsky, N. V.; Matyjaszewski, K. Environmentally Benign Atom Transfer Radical Polymerization: Towards "Green" Processes and Materials J. Polym. Sci., Polym. Chem. 2006, 44, 5098
6. Shen, Y.; Tang, H.; Ding, S. Catalyst Separation in Atom Transfer Radical Polymerization Prog. Polym. Sci. 2004, 29, 1053
7. Tsarevsky, N. V; Matyjaszewski, K. "Green" Atom Transfer Radical Polymerization: from Process Design to Preparation of Well-Defined Environmentally Friendly Polymeric Materials Chem. Rev. 2007, 107, 2270
8. Destarac, M. Controlled Radical Polymerization: Industrial Stakes, Obstacles and Achievements Macromol. React. Eng. 2010, 4, 165
9. Jakubowski, W.; Min, K.; Matyjaszewski, K. Activators Regenerated by Electron Transfer for Atom Transfer Radical Polymerization of Styrene Macromolecules 2006, 39, 39
10. Matyjaszewski, K.; Jakubowski, W.; Min, K.; Tang, W.; Huang, J.; Braunecker, W. A.; Tsarevsky, N. V. Diminishing Catalyst Concentration in Atom Transfer Radical Polymerization with Reducing Agents Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15309
11. Mueller, L.; Jakubowski, W.; Tang, W.; Matyjaszewski, K. Successful Chain Extension of Polyacrylate and Polystyrene Macroinitiators with Methacrylates in an ARGET and ICAR ATRP Macromolecules 2007, 40, 6464
12. Pietrasik, J.; Dong, H.; Matyjaszewski, K. Synthesis of High Molecular Weight Poly(styrene-co -acrylonitrile) Copolymers with Controlled Architecture Macromolecules 2006, 39, 6384
13. Min, K.; Gao, H.; Matyjaszewski, K. Use of Ascorbic Acid as Reducing Agent for Synthesis of Well-Defined Polymers by ARGET ATRP Macromolecules 2007, 40, 1789
14. Jakubowski, W.; Matyjaszewski, K. Activators Regenerated by Electron Transfer for Atom-Transfer Radical Polymerization of (Meth)acrylates and Related Block Copolymers Angew. Chem., Int. Ed. 2006, 45, 4482
15. 6TREN Macromol. Rapid Commun. 2008, 29, 1834
16. Dong, H.; Matyjaszewski, K. ARGET ATRP of 2-(Dimethylamino)ethyl Methacrylate as an Intrinsic Reducing Agent Macromolecules 2008, 41, 6868
17. Paterson, S. M.; Brown, D. H.; Chirila, T. V.; Keen, I.; Whittaker, A. K.; Baker, M. V. The Synthesis of Water-Soluble PHEMA via ARGET ATRP in Protic Media J. Polym. Sci., Polym. Chem. 2010, 48, 4084
18. Min, K.; Jakubowski, W.; Matyjaszewski, K. AGET ATRP in the Presence of Air in Miniemulsion and in Bulk Macromol. Rapid Commun. 2006, 27, 594
19. Matyjaszewski, K.; Dong, H.; Jakubowski, W.; Pietrasik, J.; Kusumo, A. Grafting from Surfaces for "Everyone": ARGET ATRP in the Presence of Air Langmuir 2007, 23, 4528
20. Chan, N.; Boutti, S.; Cunningham, M. F.; Hutchinson, R. A. Continuous Atom Transfer Radical Polymerization with Low Catalyst Concentration in a Tubular Reactor Macromol. React. Eng. 2009, 3, 222
21. Zhang, M.; Ray, W. H. Modeling of "Living" Free-Radical Polymerization Processes. I. Batch, Semibatch, and Continuous Tank Reactors J. Appl. Polym. Sci. 2002, 86, 1630
22. Schork, F. J.; Smulders, W. On the Molecular Weight Distribution Polydispersity of Continuous Living-Radical Polymerization J. Appl. Polym. Sci. 2004, 92, 539
23. Chan, N.; Cunningham, M. F.; Hutchinson, R. A. Continuous Controlled Radical Polymerization of Methyl Acrylate with Copper Wire in a CSTR Polym. Chem. 2012, 3, 486
24. Chan, N.; Cunningham, M. F.; Hutchinson, R. A. Reducing ATRP Catalyst Concentration in Batch, Semibatch and Continuous Reactors Macromol. React. Eng. 2010, 4, 369
25. Chan, N.; Cunningham, M. F.; Hutchinson, R. A. ARGET ATRP of Methacrylates and Acrylates with Stoichiometric Ratios of Ligand to Copper Macromol. Chem. Phys. 2008, 209, 1797
26. Britovsek, G. J. P.; England, J.; White, A. J. P. Non-Heme Iron(II) Complexes Containing Tripodal Tetradentate Nitrogen Ligands and Their Application in Alkane Oxidation Catalysis Inorg. Chem. 2005, 44, 8125
27. Eckenhoff, W. T.; Garrity, S. T.; Pintauer, T. Highly Efficient Copper-Mediated Atom-Transfer Radical Addition (ATRA) in the Presence of Reducing Agent Eur. J. Inorg. Chem. 2008, 2008, 563
28. Beuermann, S.; Buback, M.; Davis, T. P.; Gilbert, R. G.; Hutchinson, R. A.; Kajiwara, A.; Klumperman, B.; Russell, G. T. Critically Evaluated Rate Coefficients for Free-Radical Polymerization, 3. Propagation Rate Coefficients for Alkyl Methacrylates Macromol. Chem. Phys. 2000, 201, 1355
29. Penzel, E.; Goetz, N. Solution Properties of Polyacrylic Esters Angew. Makromol. Chem. 1990, 178, 191
30. Faucher, S.; Okrutny, P.; Zhu, S. Catalyst Solubility and Experimental Determination of Equilibrium Constants for Heterogeneous Atom Transfer Radical Polymerization Ind. Eng. Chem. Res. 2007, 46, 2726
31. Braunecker, W. A.; Tsarevsky, N. V.; Gennaro, A.; Matyjaszewski, K. Thermodynamic Components of the Atom Transfer Radical Polymerization Equilibrium: Quantifying Solvent Effects Macromolecules 2009, 42, 6348
32. Coullerez, G.; Malmström, E.; Jonsson, M. Solvent Effects on the Redox Properties of Cu Complexes used as Mediators in Atom Transfer Radical Polymerization J. Phys. Chem. A 2006, 110, 10355
33. Lin, C. Y.; Coote, M. L.; Gennaro, A.; Matyjaszewski, K. Ab Initio Evaluation of the Thermodynamic and Electrochemical Properties of Alkyl Halides and Radicals and Their Mechanistic Implications for Atom Transfer Radical Polymerization J. Am. Chem. Soc. 2008, 130, 12762
34. Tang, W.; Matyjaszewski, K. Effects of Initiator Structure on Activation Rate Constants in ATRP Macromolecules 2007, 40, 1858
35. Tang, W.; Kwak, Y.; Braunecker, W.; Tsarevsky, N. V.; Coote, M. L.; Matyjaszewski, K. Understanding Atom Transfer Radical Polymerization: Effect of Ligand and Initiator Structures on the Equilibrium Constants J. Am. Chem. Soc. 2008, 130, 10702
36. Payne, K. A.; D'hooge, D. R.; Van Steenberge, P. H. M.; Reyniers, M.-F.; Cunningham, M. F.; Hutchinson, R. A.; Marin, G. B. ARGET ATRP of Butyl Methacrylate: Utilizing Kinetic Modeling to Understand Experimental Trends Macromolecules 2013, 46, 3828