Synthesis and styrene copolymerization of novel alkoxy ring-substituted octyl phenylcyanoacrylates

David R.  Graykowski; Marlena D.  Hadas; Marianna C.  Haddad; Jacqueline  Jimenez; Marcelina A.  Skowronski; Jade D.  Smith; Brendan S.  Van Voorhis; Zoe M.  Varsbergs; Sara M.  Rocus; William S.  Schjerven; Gregory B Kharas

doi:10.26434/chemrxiv-2022-q4h2z

Organic Chemistry

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Synthesis and styrene copolymerization of novel alkoxy ring-substituted octyl phenylcyanoacrylates

Working Paper

David R. Graykowski DePaul University ,
Marlena D. Hadas DePaul University ,
Marianna C. Haddad DePaul University ,
Jacqueline Jimenez DePaul University ,
Marcelina A. Skowronski DePaul University ,
Jade D. Smith DePaul University ,
Brendan S. Van Voorhis DePaul University ,
Zoe M. Varsbergs DePaul University ,
Sara M. Rocus DePaul University ,
William S. Schjerven DePaul University ,
Gregory B Kharas DePaul University

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Abstract

Novel alkoxy ring-substituted octyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2(CH2)6CH3 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-butoxy, 4-hexyloxy) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and octyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the acrylates were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were calculated from nitrogen analysis.