Reactive extraction of cis,cis-muconic acid

The reactive extraction (RE) of carboxylic and dicarboxylic acids, such as cis,cis‑muconic acid (CCMA), is a promising integrated approach towards an efficient downstream processing development. Dicarboxylic acids have a high potential to be used as precursors for polymerization reactions or as monomers for new and innovative polymers and can be produced by biocatalytic production. In this work water-insoluble long chain amines and water-soluble short chain amines were evaluated as extractants for the RE of CCMA. The biocompatible organic solvent ethyl oleate and mixtures of ethyl oleate and a polar modifier were used as organic phase for all experiments presented. Three out of six water-insoluble amines (di-n-octylamine (D-C8), tri-n-hexalamine (T-C6), tri-n-octylamine (T-C8)) were shown to be applicable extractants for the RE of CCMA. A systematic investigation of the mutual influence of amine and modifier on RE performance was performed for the first time. The best performing systems (D-C8: bD-C8 =  0.1 mol kgorg−1, w1-dodecanol =  0.3/T-C8: bT-C8 =  0.15 mol kgorg−1, w1-dodecanol = 0.1) in terms of yield and inhibition of a third phase presented in this work, lead to yields of X ∼0.95–0.96 ± 0.04.