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A two-step efficient preparation of a renewable dicarboxylic acid monomer 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid] from D-fructose and its application in polyester synthesis
Chemistry & Physics Faculty Publications
  • Ananda S. Amarasekara, Prairie View A & M University
  • Loc H Nguyen, Prairie View A & M University
  • Nnaemeka C. Okorie, Prairie View A & M University
  • Saad M Jamal, Prairie View A & M University
Document Type
Article
Publication Date
1-1-2017
Abstract

D-Fructose was converted to the dialdehyde 5,5′-[oxybis(methylene)]bis[2-furaldehyde] by heating at 110°C in DMSO with the Dowex 50 W X8 solid acid catalyst in 76% yield without the isolation of the intermediate 5-hydroxymethylfurfural. This dialdehyde was then converted to the dicarboxylic acid monomer, 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid], using oxygen (1 atm.) and 5% Pt/C catalyst in 1.5 M aqueous NaOH at room temperature in 98% yield. The new dicarboxylic acid monomer can be considered as a renewable resource based alternative to terephthalic acid as demonstrated by the preparation of polyesters with 1,2-ethanediol and 1,4-butanediol in 87-92% yield.

Citation Information
Ananda S. Amarasekara, Loc H Nguyen, Nnaemeka C. Okorie and Saad M Jamal. "A two-step efficient preparation of a renewable dicarboxylic acid monomer 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid] from D-fructose and its application in polyester synthesis" (2017)
Available at: http://works.bepress.com/httpswwwpvamuedubcasdepartmentschemistryfaculty-and-staffasamarasekara/15/