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Jones GO, Yuen A, Wojtecki RJ, et al. Computational and experimental investigations of one-step conversion of poly(carbonate)s into value-added poly(aryl ether sulfone)s. Proc Natl Acad Sci U S A. 2016;113(28):7722-6doi: 10.1073/pnas.1600924113.
Jones, G. O., Yuen, A., Wojtecki, R. J., Hedrick, J. L., & García, J. M. (2016). Computational and experimental investigations of one-step conversion of poly(carbonate)s into value-added poly(aryl ether sulfone)s. Proceedings of the National Academy of Sciences of the United States of America, 113(28), 7722-6. https://doi.org/10.1073/pnas.1600924113
Jones, Gavin O, et al. "Computational and experimental investigations of one-step conversion of poly(carbonate)s into value-added poly(aryl ether sulfone)s." Proceedings of the National Academy of Sciences of the United States of America vol. 113,28 (2016): 7722-6. doi: https://doi.org/10.1073/pnas.1600924113
Jones GO, Yuen A, Wojtecki RJ, Hedrick JL, García JM. Computational and experimental investigations of one-step conversion of poly(carbonate)s into value-added poly(aryl ether sulfone)s. Proc Natl Acad Sci U S A. 2016 Jul 12;113(28):7722-6. doi: 10.1073/pnas.1600924113. Epub 2016 Jun 27. PMID: 27354514; PMCID: PMC4948316.
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Proc Natl Acad Sci U S A. 2016 Jul 12;113(28):7722-6. doi: 10.1073/pnas.1600924113. Epub 2016 Jun 27.

Computational and experimental investigations of one-step conversion of poly(carbonate)s into value-added poly(aryl ether sulfone)s.

Proceedings of the National Academy of Sciences of the United States of America

Gavin O Jones, Alexander Yuen, Rudy J Wojtecki, James L Hedrick, Jeannette M García

Affiliations

  1. IBM Research-Almaden, San Jose, CA 95120 [email protected] [email protected].
  2. IBM Research-Almaden, San Jose, CA 95120.

PMID: 27354514 PMCID: PMC4948316 DOI: 10.1073/pnas.1600924113

Abstract

It is estimated that ∼2.7 million tons poly(carbonate)s (PCs) are produced annually worldwide. In 2008, retailers pulled products from store shelves after reports of bisphenol A (BPA) leaching from baby bottles, reusable drink bottles, and other retail products. Since PCs are not typically recycled, a need for the repurposing of the PC waste has arisen. We report the one-step synthesis of poly(aryl ether sulfone)s (PSUs) from the depolymerization of PCs and in situ polycondensation with bis(aryl fluorides) in the presence of carbonate salts. PSUs are high-performance engineering thermoplastics that are commonly used for reverse osmosis and water purification membranes, medical equipment, as well as high temperature applications. PSUs generated through this cascade approach were isolated in high purity and yield with the expected thermal properties and represent a procedure for direct conversion of one class of polymer to another in a single step. Computational investigations performed with density functional theory predict that the carbonate salt plays two important catalytic roles in this reaction: it decomposes the PCs by nucleophilic attack, and in the subsequent polyether formation process, it promotes the reaction of phenolate dimers formed in situ with the aryl fluorides present. We envision repurposing poly(BPA carbonate) for the production of value-added polymers.

Keywords: computational chemistry; mechanism; polycondensation; polymers; recycling

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