Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes. Issue 48 (15th October 2019)

• Record Type: Journal Article
• Authors: Saska, Jan; Li, Zheng; Otsuki, Andrew L.; Wei, Jiahui; Fettinger, James C.; Mascal, Mark
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 48(2019)
• Page Start: 17293
• Page End: 17296
• Publication Date: 2019-10-15
• Subjects: biomass conversion -- chromophores -- dyes/pigments -- furans -- sustainable chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201911387
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The dye and pigment manufacturing industry is one of the most polluting in the world. Each year, over one million tons of petrochemical colorants are produced globally, the synthesis of which generates a large amount of waste. Naturally occurring, plant‐based dyes, on the other hand, are resource intensive to produce (land, water, energy), and are generally less effective as colorants. Between these two extremes would be synthetic dyes that are fully sourced from biomass‐derived intermediates. The present work describes the synthesis of such compounds, containing strong chromophores that lead to bright colors in the yellow to red region of the visible spectrum. The study was originally motivated by an early report of an unidentified halomethylfurfural derivative which resulted from hydrolysis in the presence of barium carbonate, now characterized as a butenolide of 5‐(hydroxymethyl)furfural (HMF). The method has been generalized for the synthesis of dyes from other biobased platform molecules, and a mechanism is proposed. Abstract : To dye for : Synthetic dyes are yet another industrial commodity that can be sustainably produced wholly from biomass‐derived platform molecules. The synthesis of biobased dyes containing strong chromophores that lead to bright colors in the yellow to red region of the visible spectrum is described.