Reactive extraction of cis,cis-muconic acid

Recovery of cis,cis-muconic acid from organic phase after reactive extraction

“…The concentration analysis of the CCMA in the aqueous phase was performed via high pressure liquid chromatography (HPLC) as described by Gorden et al [9] using an Agilent 1200 Series HPLC (Santa Clara, USA) and a series of a Zorbax SB-C18, 4.6 Á 12.5 mm, 3.5 lm guard column, a Zorbax SB-C18, 4.6 Á 50 mm, 1.8 lm, and a Zorbax Extend-C18, 4.6 Á 50 mm, 1.8 lm column [by Agilent Technologies (Santa Clara, USA)]. The temperature was kept constant at 40°C.…”

“…Thus, there is an immediate need for an economic and selective product capture step to recover the dicarboxylic acid from the fermentation broth. One promising approach described recently is the application of a reactive extraction (RE) for this purpose [9]. By combining the beneficial attributes of an extraction and a reaction, the distribution behavior within a liquid-liquid extraction can be favored towards a selective recovery of the product.…”

“…Reactive extraction of dicarboxylic acids has been shown to be applicable for various dicarboxylic acids, e.g. malonic acid [15][16][17], glutaric acid [18], succinic acid [15][16][17][19][20][21][22][23], fumaric acid [15][16][17], malic acid [18,24], maleic acid [15][16][17][18], itaconic acid [25][26][27] and cis,cismuconic acid (CCMA) [9]. However, the crucial step towards an applicable downstream process is not only the initial RE of the acid, but also a re-extraction (REEX) of the acid from the organic phase leading to the pure acid in an aqueous phase for further processing.…”

“…Option 4 makes use of the strong pH dependency of the RE. It was previously shown [9] that a RE using pure amine as extractant is only possible if the pH is lower than the smallest pK a of the dicarboxylic acid. An aqueous phase set to a pH higher than the pK a of the acid thus leads to a breakup of the complex and a subsequent REEX of the acid into an aqueous phase.…”

“…Trimethylamine is corrosive and gaseous at standard conditions and by that highly volatile. In our previous work [9] we already assumed that the group of amine candidates for REEX can be extended to water soluble amines (WSA) in general. In order to circumvent the problems associated with the use of an aqueous trimethylamine solution (corrosivity, high volatility) and allow for an understanding of the REEX mechanism, two different strategies were investigated within this work: (1) the REEX via pH-shift and (2) the REEX using WSA's.…”