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Iron(III) porphyrin catalyzed polymerization of acrylamide in ionic liquids

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Abstract

Iron(III) porphyrin is advocated as catalyst for polymerization of acrylamide with hydrogen peroxide in ionic liquid medium. Reaction conditions were optimized using different porphyrins, solvents, oxidants and initiators. The polymer products were characterized by using 1H NMR, FT-IR, GPC and Mass spectrometric techniques. The recyclability of catalyst and ionic liquids, high yields, high molecular weights and simple work-up procedure are the important attributes of this protocol and contribute as an attractive addition to polymer chemistry.

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References

  1. Jackson P (1996) The analysis of fluorophore-labeled carbohydrates by polyacrylamide gel electrophoresis. Mol Biotechnol 5:101–123

    Article  CAS  Google Scholar 

  2. Kurenkov VF, Hartan H–G, Lobanov FI (2002) Application of polyacrylamide flocculants for water treatment. Chemistry and Computer Simulation Butlerov’s Communications 3:31–40

    Google Scholar 

  3. Barani K, Kalantari M (2017) Recovery of kaolinite from tailings of zonouz kaolinwashing plant by flotation-flocculation method. J Mater Res Technol 7:142–148

    Article  Google Scholar 

  4. Zou W, Zhao J, Sun C (2018) Adsorption of anionic polyacrylamide onto coal and kaolinite calculated from the extended DLVO theory using the van OssChaudhury-good theory. Polymers 10:113–123

    Article  Google Scholar 

  5. Dos Santos LA, Carrodeguas RG, Boschi AO, De Arruda AC (2003) Dualsetting calcium phosphate cement modified with ammonium polyacrylate. Artif Organs 27:412–418

    Article  CAS  Google Scholar 

  6. Borling D, Chan K, Hughes E and Sydansk R (1994) Pushing out the oil with conformance control, Oil Field Rev (April), 44–58

  7. Bologna LS, Andrawes FF, Barwenik FW, Lentz RD, Sozka RE (1999) Analysis of residual acrylamide in field crops. J Chromatogr Sci 37:240–244

    Article  CAS  Google Scholar 

  8. Pogorelova SP, Bourenko T, Kharitonov AB, Willner I (2002) Selective sensing of triazine herbicides in imprinted membranes using ionsensitive field effect transistors and microgravimetric quartz crystal microbalance measurements. Analyst 127:1484–1491

    Article  CAS  Google Scholar 

  9. Jain R, Mahto V (2015) Evaluation of polyacrylamide/clay composite as a potential drilling fluid additive in inhibitive water based drilling fluid system. J Pet Sci Eng 133:612–621

    Article  CAS  Google Scholar 

  10. Farrokhpay S, Morris GE, Fornasiero D, Self P (2006) Titania pigment particles dispersion in water-based paint films. JCT Res 3:275–283

    CAS  Google Scholar 

  11. Mukhopadhyay A, Midha VK (2008) A review on designing the waterproff breathable fabrics part II: construction and suitability of breathable fabrics for different uses. J Ind Text 38:17–41

    Article  CAS  Google Scholar 

  12. Chen Z, Chen W, Li C, Pu Y, Sun H (2016) Effects of polyacrylamide on soil erosion and nutrient losses from substrate material in steep rocky slope stabilization projects. Sci Total Environ 554-555:26–33

    Article  CAS  Google Scholar 

  13. Yang T–H (2008) Recent applications of polyacrylamide as biomaterials. Recent Patents on Materials Science 1:29–40

    Article  CAS  Google Scholar 

  14. Helvacioglu E, Aydin V, Nugay T, Nugay N, Uluocak BG, Sen S (2011) High strength poly(acrylamide)-clay hydrogels. J Polym Res 18:2341–2350

    Article  CAS  Google Scholar 

  15. -Lamgroudi AE, Rabiee A (2012) A novel acrylamide-anatase hybrid nanocomposite. J Polym Res 19:9970–9982

    Article  Google Scholar 

  16. Sanchez-Leija RJ, Torres-Lubian JR, Resendiz-Rubio A, Luna-Barcenas G, Mota-Morales JD (2016) Enzyme-mediated free radical polymerization of acrylamide in deep eutectic solvents. RSC Adv 6:13072–13079

    Article  CAS  Google Scholar 

  17. Gur’eva LL, Tkachuk AI, Estrin YI, Komarov BA, Dzhavadyan EA, Estrina GA, Bogdanova LM, Surkov NF, Rosenberg BA (2008) Synthesis and free-radical polymerization of water-soluble acrylamide monomers. Polym Sci Ser A 50:283–290

    Article  Google Scholar 

  18. Singh S, Singh A, Yadav BC, Tandon P, Kumar S, Yadav RR, Pomogailo SI, Dzhardimalieva GI, Pomogailo AD (2015) Frontal polymerization of acrylamide complex with nanostructured ZnS and PbS: their characterizations and sensing applications. Sensors Actuators B Chem 207:460–469

    Article  CAS  Google Scholar 

  19. Wang G–X, Lu M, Hou Z–H, Liu L–C, Liang E–X, Wu H (2015) Living radical polymerization of polyacrylamide with submicrometer size by dispersion polymerization. E-Polymers 15:0200

    Google Scholar 

  20. Chiu D-J, Li Y, Feng C-K, Yang M-R, Chen K-S, Swieszkowski W (2017) Preparation and enhanced mechanical properties of hydroxyapatite hybrid hydrogels via novel photocatalytic polymerization. J Polym Res 24:227–235

    Article  Google Scholar 

  21. Grassl B, Clisson G, Khoukh A, Billon L (2008) Nitroxide-mediated radical polymerization of acrylamide in water solution. Eur Polym J 44:50–58

    Article  CAS  Google Scholar 

  22. Zhang Y, Ye L, Diao Y, Lei W, Shi L, Ran R (2016) RAFT polymerization of acrylamide manipulated with trithiocarbonates in poly(ethylene glycol) solution. J Appl Polym Sci 133:1–12

    Google Scholar 

  23. Karpenko MA, Kolzunova LG (2011) Initiation of electropolymerization of acrylamide and formaldehyde by metallic zinc in aqueous medium. Russ J Electrochem 47:1091–1095

    Article  CAS  Google Scholar 

  24. Ding S, Rodosz M, Shen Y (2005) Ionic liquid catalysts for biphasic atom transfer radical polymerization of methyl methacrylate. Macromolecules 38:5921–5928

    Article  CAS  Google Scholar 

  25. Biedron T, Kubisa P (2005) Radical polymerization in a chiral ionic liquid: atom transfer radical polymerization of acrylates. J Polym Sci A polym Chem 43:3454–3459

    Article  CAS  Google Scholar 

  26. Shaughnessy KH, Klingshirn MA, P’Pool SJ, Holbrey JD, Rogers RD (2003) Polar non-coordinating ionic liquids as solvents for coordination polymerization of olefins in ionic liquids as green solvents. ACS Symp Ser 856:300–313

    Article  CAS  Google Scholar 

  27. Kalra B, Gross RA (2000) Horseradish mediated free radical polymerization of methyl methacrylate. Biomacromolecules 1:501–505

    Article  CAS  Google Scholar 

  28. Chauhan SMS, Kalra B, Mohapatra PP (1999) Oxidation of 1-naphthol and related phenols with hydrogen peroxide and potassium superoxide catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in different reaction conditions. J Mol Catal A Chem 137:85–92

    Article  CAS  Google Scholar 

  29. Kumari P, Nagpal R, Chauhan P, Yatindranath V, Chauhan SMS (2015) Efficient iron(III) porphyrins-catalyzed oxidation of guanidoximes to cyanamides in ionic liquids. J Chem Sci 127:13–18

    Article  CAS  Google Scholar 

  30. Singhal A, Chauhan SMS (2012) Biomimetic oxidation of guggulsterone with hydrogen peroxide catalyzed by iron(III)porphyrins in ionic liquid. Catal Commun 25:28–31

    Article  CAS  Google Scholar 

  31. Li J, Li M, Li S, Shi L, Ren C, Cui D, Wang Y, Tang T (2008) Styrene polymerization catalyzed by metal porphyrin complex/ MAO for in situ synthesizing polystyrene containing air stable π-cation radicals. J Polym Sci A Polym Chem 46:1240–1248

    Article  CAS  Google Scholar 

  32. Brounecker WA, Itami Y, Matyjaszewski K (2005) Osmium mediated radical polymerizations. Macromolecules 38:9402–9404

    Article  Google Scholar 

  33. Angrish C, Chauhan SMS (2004) Biomimetic polymerization of acrylamide with hydrogen peroxide catalysed by water-soluble anionic iron(III)5,10,15,20- tetrakis-(2′,6′-dichloro-3′-sulphonatophenyl)porphyrin. ARKINOV viii:61–68

    Google Scholar 

  34. Singhal A, Ahmad S, Chauhan SMS (2018) Iron(III)porphyrin catalyzed ionic liquid mediated polymerization of methylmethacrylate. Appl Organomet Chem 32:1–6

    Article  Google Scholar 

  35. Singhal A, Chauhan SMS (2018) Free radical copolymerization of acrylamide and N-vinylpyrrolidone catalyzed by iron(III)porphyrins in the presence of ionic liquids. Org Prep Proced Int 50(3):359–371

    Article  CAS  Google Scholar 

  36. Kubisa P (2004) Application of ionic liquids as solvents for polymerization processes. Prog Polym Sci 29:3–12

    Article  CAS  Google Scholar 

  37. Shaughnessy KH, Klingshirn MA, P’Pool SJ, Holbrey JD, Rogers RD (2003). ACS Symp Ser 856:300–313

    Article  CAS  Google Scholar 

  38. Vijayaraghvan R, Macfarlane DR (2004) Living cationic polymerization of styrene in an ionic liquid. Chem Commun:700–701

  39. Vijayaraghvan R, Macfarlane DR (2005) Group transfer polymerization in hydrophobic ionic liquids. Chem Commun:1149–1151

  40. Uyama H, Takamoto T, Kobayahi S (2002) Enzymatic synthesis of polyesters in ionic liquids. Polym J Japan 34:94–96

    Article  CAS  Google Scholar 

  41. Pringle JM, Forsyth M, Macfarlane DR, Wagner K, Hall SB, Officer DL (2005) The influence of the monomer and the ionic liquid on the electrochemical preparation of the polythiophene. Polymer 46:2047–2058

    Article  CAS  Google Scholar 

  42. Vygodskii Y, Lozinskaya EI, Shaplov AS, Lyssenko KA, Antipin MY, Urman YG (2004) Implementation of ionic liquids as activating media for polycondensation processes. Polymer 45:5031–5045

    Article  CAS  Google Scholar 

  43. Tang H, Qu Y, Li Y, Dong S (2018) Synthesis of hydroxypropylated debranched pea starch with high substitution degree in an ionic liquid, and its characterization and properties. J Polym Res 25:235–246

    Article  Google Scholar 

  44. Zhang X, Liu W, Chen Y, Gong A, Chen C, Xi F (1999) Self-condensing vinyl polymerization of acrylamide. Polym Bull 43:29–34

    Article  CAS  Google Scholar 

  45. Singh V, Tiwari A, Kumari P, Sharma AK (2007) Microwave accelerated synthesis and characterization of poly(acrylamides), J. Appl Polym Sci 104:3702–3707

    Article  CAS  Google Scholar 

  46. kalra B, Gross RA (2002) HRP-mediated polymerization of acrylamide and sodium acrylate. Green Chem 4:174–178

    Article  CAS  Google Scholar 

  47. Behari K, Raja GD, Agarwal A (1989) Kinetics of perphosphotase-initiated polymerization of acrylamide with different activators. Polymer 30:726–731

    Article  CAS  Google Scholar 

  48. Gupta KC, Verma M, Behari K (1986) Studies on the aqueous polymerization of acrylamide initiated by the potassium permanganate/glyceric acid redox system. Macromolecules 19:548–551

    Article  CAS  Google Scholar 

  49. Guan S-Y, Mlyna RJ, Sarkanen S (1997) Dehydrogenative polymerization of conifery alcohol on macromolecular lignin templates. Phytochemistry 45:911–918

    Article  CAS  Google Scholar 

  50. Guerra A, Ferraz A, Cotrim AR, Da Silva FT (2000) Polymerization of lignin fragments contained in a model effluent by polyphenoloxidases and horseradish peroxidase/ hydrogen peroxide system. Enzym Microb Technol 26:315–323

    Article  CAS  Google Scholar 

  51. Machii K, Wantabe Y, Morishima I (1995) Acyl peroxo-iron(III) porphyrin complexes: a new entry of potent oxidants for the alkene epoxidation. J Am Chem Soc 117:6691–6697

    Article  CAS  Google Scholar 

  52. Lippai I, Magliozzo RS, Peisach J (1999) EPR spectroscopic reinvestigation of the activation of iron(III) complexes of PMAH as a bleomycin model. J Am Chem Soc 121:780–784

    Article  CAS  Google Scholar 

  53. Lalot T, Brigodiot M, Marechal E (1999) A kinetic approach to acrylamide radical polymerization by horse radish peroxidase-mediated initiation. Polym Int 48:288–292

    Article  CAS  Google Scholar 

  54. Fujii H (1993) Effects of the electron-withdrawing power of substituents on the electronic structure and reactivity in oxoiron(IV) porphyrin π-cation radical complexes. J Am Chem Soc 115:4641–4648

    Article  CAS  Google Scholar 

  55. Meunier B (1992) Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem Rev 92:1411–1456

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful for financial assistance to the Council of Scientific and Industrial Research (CSIR), New Delhi, India. We also thank Indian Institute of Technology, Delhi for facilitating GPC analysis and Central Instrumentation Facility (CIF), University of Delhi for characterization of polymer products.

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  1. Department of Chemistry, University of Delhi, Delhi, 110007, India

    Anchal Singhal & S. M. S. Chauhan

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Correspondence to Anchal Singhal.

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Singhal, A., Chauhan, S.M.S. Iron(III) porphyrin catalyzed polymerization of acrylamide in ionic liquids. J Polym Res 26, 3 (2019). https://doi.org/10.1007/s10965-018-1663-7

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