Ethoxylation and Polymerization of Cardanol Derived Bifunctional Monomers
Corresponding Author(s) : james mgaya
Journal of Humanities & Social Science (JHSS),
Vol. 9 No. 2 (2020): SPECIAL ISSUE OF SCIENCE, 2020
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
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- 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–
- 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. ColeHamilton. 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 NutShell Liquid From the Cashew Nut (AnacardiumoCcidentale). Journal of the American Oil
- Chemists Society, 66: 553–557.
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–
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. ColeHamilton. 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 NutShell Liquid From the Cashew Nut (AnacardiumoCcidentale). Journal of the American Oil
Chemists Society, 66: 553–557.