Campus Units

Chemistry, NSF Engineering Research Center for Biorenewable Chemicals

Document Type

Article

Publication Version

Accepted Manuscript

Publication Date

1-23-2014

Journal or Book Title

Green Chemistry

Volume

16

Issue

4

First Page

2111

Last Page

2116

DOI

10.1039/C3GC42487A

Abstract

Diverse functionalized aromatic compounds are constructed from captodative dienophiles with exclusive regioselectivity. 100% biorenewable dimethyl terephthalate (DMT) from methyl coumalate and methyl pyruvate is achieved in a one-pot, Diels–Alder/decarboxylation/elimination sequence in nearly quantitative yield. The DMT system is solvent-free and purification is accomplished through recrystallization. DMT hydrolysis reveals the co-monomer terephthalic acid (TPA) as a bio-based drop-in replacement for the polymer industry, avoiding harsh oxidation and petrochemicals.

Comments

This is a manuscript of an article published as Lee, Jennifer J., and George A. Kraus. "One-pot formal synthesis of biorenewable terephthalic acid from methyl coumalate and methyl pyruvate." Green Chemistry 16, no. 4 (2014): 2111-2116. DOI: 10.1039/C3GC42487A. Posted with permission.

Copyright Owner

The Royal Society of Chemistry

Language

en

File Format

application/pdf

Published Version

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