Poly(p-phenylene) (PPP) is a rigid-rod polymer with high strength and excellent thermal stability. Obtaining high molecular weight PPP necessitates using a soluble polymer precursor route from 5,6 cis-dihydroxycylclohexane 1,3-diene (cis-DHCD). A challenge to scale-up is the separation and purification of the reactive monomer. Cis-DHCD can be synthesized by enzymatic dihydroxylation and reduction of benzene. In this study, the requisite enzymes from Pseudomonas putida F1 have been cloned into E.coli B under the control of the lac operon and used to produce cis-DHCD. Monomers derived by conventional synthetic organic chemistry polymerize with difficulty due to the formation of trans-DHCD. Our objective is to develop a superior purification process specific to cis-DHCD. Purification steps include ion exchange and reverse-phase chromatography. HPLC and H1NMR results confirm the structure and purity of cis-DHCD. This approach has the potential to lead to an economical and scalable purification process of cis-DHCD, the precursor to PPP.

Chromatographic purification of 5,6 cis-dihydroxycylclohexane 1,3-diene, the precursor to poly(para-phenylene)

253rd National Meeting (2017)

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