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Green Methodology with Ionic Liquids as a Media for Efficient Synthesis of Polyamides Derived from 4-(4-Dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione and Diacid Chlorides2

Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, I.R. Iran

Zahra Rafiee

Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, I.R. Iran

Ionic liquids (ILs) represent a fascinating and potentially very valuable group of new solvents, which have the benefit of zero vapor pressure and therefore easier handling than many conventional solvents. They are attracting a lot of attention as volatile organic compound-free solvents, eco-friendly and green media. Room-temperature ionic liquids (RTILs) and particularly those based on substituted imidazolium cations, which can be synthesized easily from the commercially available starting material N-trimethylsilylimidazole and alkyl halides, are currently being extensively studied for a variety of applications. In this study a facile and efficient synthesis of heterocyclic polyamides by polycondensation of 4-(4-dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione with various commercially available aliphatic diacid chlorides in the presence of RTILs and molten tetrabutylammonium bromide as an IL was performed. The effect of various reaction parameters, including the nature of the ILs, the amount of IL, the reaction temperature, and the reaction time were investigated to optimize the conditions for the preparation of heterocyclic polyamides. The polymerization proceeded well in ILs without any catalyst and polyamides were obtained with high yields and moderate inherent viscosities. A comparative study between the effects exerted by different ILs and the conventional polymerization method is also reported.

Key Words: Room temperature ionic liquids (RTIL)s • polyamides • step-growth polymerization • inherent viscosity • 4-(4-dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione [4-(4-dimethylaminophenyl)urazole] • tetrabutylammonium bromide (TBAB) • thermogravimetric analysis (TGA)

References

• Welton, T. and Wasserscheid, P. (2002). Ionic Liquids in Synthesis, VCH-Wiley, Weinheim.
• Farmer, V. and Welton, T. (2002). The Oxidation of Alcohols in Substituted Imidazolium Ionic Liquids Using Ruthenium Catalysts, Green Chem., 4: 97—102.[CrossRef]
• Revell, J.D. and Ganesan, A. (2002). Ionic Liquid Acceleration of Solid-Phase Suzuki-Miyaura Cross-Coupling Reactions, Org. Lett., 4: 3071—3073.[CrossRef][Web of Science][Medline] [Order article via Infotrieve]
• Marcinek, A., Zielonka, J., Geübicki, J., Gordon, C.M. and Dunkin, I.R. (2001). Ionic Liquids: Novel Media for Characterization of Radical Ions, J. Phys. Chem. A., 105: 9305—9309.[Web of Science]
• Prasad, A.K., Kumar, V., Malhotra, S., Ravikumar, V.T., Sanghvib, Y.S. and Parmar, V.S. (2005). Green-Methodology for Efficient and Selective Benzoylation of Nucleosides Using Benzoyl Cyanide in an Ionic Liquid, Bioorg. Med. Chem., 13: 4467—4472.[CrossRef][Medline] [Order article via Infotrieve]
• Liu, Z., Chen, Z.C. andZheng, Q.G. (2003). Mild Oxidation of Alcohols with O-Iodoxybenzoic Acid (IBX) in Ionic Liquid 1-Butyl-3-methyl-imidazolium Chloride and Water, Org. Lett., 5: 3321—3323.[CrossRef][Web of Science][Medline] [Order article via Infotrieve]
• Gu, Y., Shi, F. and Deng, Y. (2004). Ionic Liquid as an Efficient Promoting Medium for Fixation of CO2: Clean Synthesis of -Methylene Cyclic Carbonates from CO2 and Propargyl Alcohols Catalyzed by Metal Salts under Mild Conditions, J. Org. Chem., 69: 391—394.[CrossRef][Web of Science][Medline] [Order article via Infotrieve]
• Zhao, Z., Qiao, W., Wang, X., Wang, G., Li, Z. and Cheng, L. (2005). Effects of Kinds of Ionic Liquid Catalysts on Alkylations of 1-and 2-Methylnaphthalene with Alkenes, Appl. Catal. A: Gen., 290: 133—137.[CrossRef]
• Jain, N., Kumar, A., Chauhan, S. and Chauhan, S.M.S. (2005). Chemical and Biochemical Transformations in Ionic Liquids, Tetrahedron, 61: 1015—1060.[CrossRef][Web of Science]
• Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K. and Tambyrajah, V. (2002). Quaternary Ammonium Zinc- or Tin-containing Ionic Liquids: Water Insensitive, Recyclable Catalysts for Diels—Alder Reactions, Green Chem., 4: 24—26.
• Song, G., Cai, Y. and Peng, Y. (2005). Amino-Functionalized Ionic Liquid as a Nucleophilic Scavenger in Solution Phase Combinatorial Synthesis, J. Comb. Chem., 7: 561—566.[CrossRef][Web of Science][Medline] [Order article via Infotrieve]
• Vygodskii, Y.S., Lozinskaya, E.I., Shaplov, A.S., Lyssenko, K.A., Antipin, M.Yu. and Urman, Y.G. (2004). Implementation of Ionic Liquids as Activating Media for Polycondensation Processes, Polymer, 45: 5031—5045.[CrossRef][Web of Science]
• Welton, T. (1999). Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis, Chem. Rev., 99: 2071—2083.[CrossRef][Web of Science][Medline] [Order article via Infotrieve]
• Kubisa, P. (2004). Application of Ionic Liquids as Solvents for Polymerization Processes, Prog. Polym. Sci., 29: 3—12.[CrossRef]
• Welton, T. (2004). Ionic Liquids in Catalysis, Coordination Chem. Rev., 248: 2459—2477.
• Sahoo, S., Joseph, T. and Halligudi, S.B. (2005). Mannich Reaction in Bronsted Acidic Ionic Liquid: A Facile Synthesis of ß -Amino Carbonyl Compounds, J. Molecular Catal. A: Chem., 244: 179—182.
• Lozinskaya, E.I., Shaplov, A.S. and Vygodskii, Y.S. (2004). Direct Polycondensation in Ionic Liquids, Eur. Polym. J., 40: 2065—2075.[CrossRef]
• Xie, H., Zhang, S. and Duan, H. (2004). An Ionic Liquid Based on a Cyclic Guanidinium Cation is an Efficient Medium for the Selective Oxidation of Benzyl Alcohols, Tetrahedron Lett., 45: 2013—2015.[CrossRef][Web of Science]
• Khodaei, M.M., Khosropour, A.R. and Ghozati, K. (2004). Reaction of Indium ate Complexes with Allylic Compounds. Controlling SN2/SN2' Selectivity by Solvents, Tetrahedron Lett., 45: 3525—3228.[CrossRef][Web of Science]
• Calo, V., Nacci, A., Lopez, L. and Lerario, V.L. (2000). Stereoselective Synthesis of Electrophilic Spirocyclopropanes in Ionic Liquids, Tetrahedron Lett., 41: 8977—8980.[CrossRef][Web of Science]
• Ranu, B.C., Das, A. and Samanta, S. (2002). Catalysis by Ionic Liquids: Solvent-free Efficient Transthioacetalization of Acetals by Molten Tetrabutylammonium Bromide, J. Chem. Soc. Perkin Trans. 1, 34: 1520-1522.
• Khalafi-Nezhad, A. and Mokhtari, B. (2004). Tetrabutylammonium bromide: an Efficient Media for Dimethoxytritylation of the 5'-Hydroxyl Function of Nucleosides, Tetrahedron Lett., 45: 6737—6739.[CrossRef][Web of Science]
• Swatloski. R.P., Holbrey, J.D., Memon, S.B., Caldwell, G.A., Caldwell, K.A. and Rogers, R.D. (2004). Using Caenorhabditis elegans to Probe Toxicity of 1-Alkyl-3-methylimidazolium Chloride Based Ionic Liquids, Chem. Commun., 668—669.
• Pernak, J., Czepukowicz, A. and Poniak, R. (2001). New Ionic Liquids and Their Antielectrostatic Properties, Ind. Eng. Chem. Res., 40: 2379—2383.[CrossRef]
• Gaina, C., Gaina, V. and Cozan, V. (2001). Synthesis and Characterization of New Polyesters Containing Imidazolidine-2,4,5-trione Rings, Eur. Polym. J., 37: 79—84.[CrossRef]
• Mallakpour, S. and Rafiee, Z. (2004). Synthesis and Characterization of New Polyamides Derived from 4-(4'-Aminophenyl)urazole and Aliphatic Diacid Chlorides, J. Appl. Polym. Sci., 92: 3173—3185.[CrossRef]
• Mallakpour, S. and Rafiee, Z. (2004). Microwave-assisted Rapid Polycondensation Reaction of 4-(4'Acetamidophenyl)-1,2,4-triazolidine-3,5-dione with Diisocyanates, J. Appl. Polym. Sci., 91: 2103—2113.[CrossRef]
• Mallakpour, S. and Kowsari, E. (2005). Ionic Liquids as Novel Solvents and Catalysts for the Direct Polycondensation of N,N'-(4,4'-Oxydiphthaloyl)-bis-L-phenylalanine Diacid with Various Aromatic Diamines, J. Polym. Sci: Part A: Polym. Chem., 43: 6545—6553.[CrossRef]
• Mallakpour, S. and Kowsari, E. (2006). Microwave Heating in Conjunction with Ionic Liquid as a Novel Method for the Fast Synthesis of Optically Active Poly(amideimide)s Derived from N,N '-(4,4' Hexafluoroisopropylidenediphthaloyl)-bis-L-methionine and Various Aromatic Diamines, Iranian Polym. J., 15(3): 239—247.
• Mallakpour, S. and Rafiee, Z. (2006). Synthesis of Photoactive Polyureas Derived from 4-(4-Dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione and Diisocyanates, Polym. Bull., 56: 293—303.[CrossRef]
• Mallakpour, S. and Rafiee, Z. (2007) Preparation and Characterization of New Photoactive Polyamides Containing 4-(4-Dimethylaminophenyl)urazole Units, J. Appl. Polym. Sci., 103: 947—954.[CrossRef]

This version was published on August 1, 2007

High Performance Polymers, Vol. 19, No. 4, 427-438 (2007)
DOI: 10.1177/0954008306074219


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