Synthesis and Styrene Copolymerization of New Halogen and Methoxy Ring-Trisubstituted Propyl Cyanophenylpropenoates


  •  Yesenia L. Soto    
  •  Emily A. Baumgartner    
  •  Francesca R. Bertoletti    
  •  Ellen F. Gardner    
  •  Bridget M. Hofsteadter    
  •  Adis Hrvat    
  •  Aurimas Jackunas    
  •  Alex J. Jagla    
  •  Justus V. Winter    
  •  Danielle S. Ostrovsky    
  •  William S. Schjerven    
  •  Gregory B. Kharas    

Abstract

New ring-trisubstituted propyl cyanophenylpropenoates, RPhCH=C(CN)CO2C3H7 (where R is 2-bromo-3-hydroxy-4-methoxy, 5-bromo-2,3-dimethoxy, 5-bromo-2,4-dimethoxy, 6-bromo-3,4-dimethoxy, 2-chloro-3,4-dimetoxy, 5-chloro-2,3-dimetoxy, 4-bromo-2,6-difluoro, 3-chloro-2,6-difluoro, 4-chloro-2,6-difluoro) were prepared by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted benzaldehydes and propyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H and 13C-NMR. The propenoates formed copolymers with styrene in solution with radical initiation (ABCN) at 70°C. The copolymers were characterized by nitrogen elemental analysis, IR, 1H and 13C-NMR, DSC. Decomposition of the copolymers in nitrogen (TGA) occurred in two steps, first in the 200-500ºC range with residue (4.2 -8.1% wt.), which then decomposed in the 500-800ºC range.



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  • Issn(Print): 1916-9698
  • Issn(Onlne): 1916-9701
  • Started: 2009
  • Frequency: semiannual

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