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Towards Automated Monomer Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonates

preprint
submitted on 03.08.2020 and posted on 04.08.2020 by Eddy Wei Ping Tan, James L. Hedrick, Pedro Luis Arrechea, Tim Erdmann, Vivien Kiyek, Simon Lottier, Yi Yan Yang, Nathaniel Park
Accessing cyclic carbonate monomers on large scales is critical for development of any new carbonate-based material platform. This is particularly important in the context of using automated experimental systems for materials synthesis, which can often require large inputs of starting materials. However, the synthesis of carbonate monomers can be a challenging and tedious endeavor, requiring multiple synthetic steps and purifications. To address this, we report a drastically improved and scalable process for the synthesis of carbonate monomers via a two-step route that avoids the use of hazardous phosgene or chloroformate reagents. The cyclic carbonate monomers can be obtained in high yields and with minimal need for chromatographic purification. This process enables rapid access to a broad array of functional groups on the carbonate monomer and monomers generated from procedure can readily be polymerized via ring-opening polymerization.

History

Email Address of Submitting Author

npark@us.ibm.com

Institution

IBM Research–Almaden

Country

United States

ORCID For Submitting Author

0000-0002-6564-3387

Declaration of Conflict of Interest

No conflict of interest.

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