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Ethoxylation and Polymerization of Cardanol Derived Bifunctional Monomers

James E. Mgaya

Abstract

 

Cardanol and its derivative; 3-(non-8-enyl)phenol (obtained by ethenolysis reaction of cardanol) were ethoxylated via one-pot reaction with urea and ethylene glycol using Na2CO3/ZnO as co-catalysts. The ethoxylates were later methoxycarbonylated using a 1,2-bis(ditertbutylphosphinomethyl)benzene (DTBPMB) modified palladium catalyst to produce ethoxylated bifunctional monomers. Polymerization of these monomers by heating in the presence of a standard polymerization catalyst, Ti(OBu)4, formed oligomers that were plastic-like. Analysis of these oligomers by MALDI-TOF MS indicated the condensation of up to nine monomer units.

 

Keywords

cardanol, ethenolysis, ethoxylation, methoxycarbonylation, ethoxylated bifunctional monomers

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References

Bang, M.S., D.S. Yoon & J.K. Choi. 2009. Synthesis and Properties of Semi-Flexible Aromatic Polyesters Containing Pentamethylene Group in Main Chain. Materials Science, 44 (4): 436–441.

Deak, K. D., R.W. Lenz & W.S.J. Kantor. 2000. Thermotropic Liquid‐Crystalline Copolyesters Containing Substituted Phenylene Terephthalate and Ethylene Terephthalate Units. Polymer Science Part A: Polymer Chemistry, 35:197–209.

Furst, M.R.L., R. LeGoff, D. Quinzler, S. Mecking, C.H. Botting & D.J. Cole-Hamilton., 2012. Polymer Precursors from Catalytic Reactions of Natural Oils. Green Chemistry, 14: 472–477.

Julis, J., S.A. Bartlett, S. Baader, N. Beresford, E.J. Routledge, C.S.J. Cazin & D.J. Cole-Hamilton. 2014. Selective Ethenolysis and Oestrogenicity of Compounds from Cashew Nut Shell Liquid. Green Chemistry, 16: 2846–2856.

Kubota, T., & R. Nakanishi. 1964. Preparation of Fully Aromatic Polybenzoxazoles. Journal of Polymer Science Part B: Polymer Letters, 2: 655-659.

Lin, H., & S.A. Dai. 2010. One-Pot Alkoxylation of Phenols with Urea and 1, 2-Glycols. Journal of Chinese Chemical Society, 57: 167–173.

Mgaya, J. 2017. Synthesis of Industrial Chemicals from Cardanol and Anacardic Acid Components of Cashew Nut Shell Liquid. PhD Thesis, University of Dar es Salaam.

Mgaya, J.E., S.A. Bartlett, E.B. Mubofu, Q.A. Mgani, A.M.Z. Slawin, P.J. Pogorzelec & D.J. Cole-Hamilton. 2016. Synthesis of Bifunctional Monomers by the Palladium-catalyzed Carbonylation of Cardanol and its derivatives. ChemCatChem, 8:751–757.

Mmongoyo, J.A., Q.A. Mgani, S.J.M. Mdachi, P.J. Pogorzelec & D.J. Cole-Hamilton. 2012. Synthesis of a Kairomone and other Chemicals from Cardanol, A Renewable Resource. European Journal of Lipid Science and Technology, 114: 1183-1192.

Morgan, A.B. & Gilman, J.W. 2013. An Overview of Flame Retardancy of Polymeric Materials: Application, Technology, and Future Directions. Fire Materials, 37: 259–279.Perdriau, S., S. Harder, H.J. Heeres & J.G. De Vries. 2012. Selective Conversion of Polyenes to Monoenes by Rucl3-Catalyzed Transfer Hydrogenation: The Case of Cashew Nutshell Liquid. ChemSusChem., 5: 2427-2434.

Rodriguez, C.J., D.F. Foster, G.R. Eastham & D.J. Cole-Hamilton. 2004. Highly Selective Formation of Linear Esters From Terminal and Internal Alkenes Catalysed by Palladium Complexes Of Bis-(Di-Tertbutylphosphinomethyl)Benzene. Chemical Communications, 15: 1720–1721.

Tyman, J.H.P., R.A. Johnson, M. Muir & R. Rokhagar. 1989. The Extraction of Natural Cashew Nut-Shell Liquid From the Cashew Nut (AnacardiumoCcidentale). Journal of the American Oil Chemists Society, 66: 553–557.

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