New insights in reactive extraction mechanisms of organic acids: An experimental approach for 3-hydroxypropionic acid extraction with tri-n-octylamine

Abstract

A detailed study of 3-hydroxypropionic acid (3-HP) reactive extraction with tri-n-octylamine (TOA) is proposed for the first time. It aims at uncovering some solvent-solutes interactions and providing global mechanisms to better understand and design the reactive liquid-liquid extraction of 3-HP in a biotechnological process. Eleven solvents of similar molecular sizes and several chemical types (alcohols, esters and alkanes) were investigated to understand their role on the extraction ability. Alcohols were found to be the best solvents thanks to their H-bond donor characteristic and water loading that allowed good solvation of the acid-amine complexes. Further investigations were then undertaken, for n-decanol and oleyl alcohol as solvents, varying acid (0.

Organic phase screening for in‐stream reactive extraction of bio‐based 3‐hydroxypropionic acid: biocompatibility and extraction performances

“…Chen and Lee used a biocompatible organic phase composed of 20% Alamine 336, 40% oleyl alcohol and 40% kerosene by volume, for extractive fermentation of lactic acid. They obtained a partition coefficient of 0.30, lower than the one obtained in this study with the selected organic phase ( K D = 0.95 ± 0.004), but it allowed continuous acid extraction.…”

“…5 Although this pathway passes through 3-hydroxypropionaldehyde (3-HPA) production as an intermediate, which is toxic for the strain, 6 its In situ extraction occurs with a direct contact between the cells and the extraction phase: (a) two-phase partitioning bioreactors [11][12][13] or (b) solvent-impregnated particles dispersed in bioconversion medium 14,15 or with an indirect contact: (c) using immobilized cells in the bioconversion broth 16,17 ; or (d) using membrane-based extraction inside the bioreactor. 18,19 In-stream extraction occurs with direct contact: (e) pumping bioconversion broth to a column packed with solvent-impregnated particles 20 or indirect contact: (f ) membrane-based extraction outside the bioreactor 21,22 ; or (g) introducing a microfiltration unit to separate the biocatalyst from broth before contact. 23,24 accumulation in the medium can be avoided by progressively supplying glycerol.…”

“…[38][39][40][41][42] Solvents may affect cells at two different levels: by direct contact with the immiscible part of the solvent (phase-level toxicity) and interaction with the water-soluble solvent molecules (molecular-level toxicity). 40,43,44 The toxicity of several organic solvents commonly used for the reactive extraction of carboxylic acids has been assessed on different strains of microorganisms, 18,36,41,43,45 but the variable and often contradictory results suggest that the selection of a biocompatible extraction phase depends strongly on the microorganism strain used. Solvent selection according to the particular needs of an ISPR strategy is therefore a key issue.…”

Towards an in situ product recovery of bio‐based 3‐hydroxypropionic acid: influence of bioconversion broth components on membrane‐assisted reactive extraction

“…As for similar acids such as pyruvic acid and lactic acid, a good extraction system for 3‐HP is tri‐ n ‐octylamine (TOA) in n ‐decanol (decanol). Indeed, we previously showed that the solvating power of decanol leads to high extraction yields . In this system, the main reaction occurring is …”

Mathematical Modeling of Reactive Extraction of Solute from Slab Solid Material

“…Reactive extraction has been studied and applied in various systems, either in liquid-liquid system [4], solidfluid system [5] and gas-liquid-liquid system [6]. In practical terms, reactive extraction is commercially applied in separation of metals [7][8], separation of intermediates [9][10], separation of organic acids [11][12], separation of vitamins [13], separation of lignin [14][15][16], synthesis of biodiesel [17] and preparation of green oxidants such as hydrogen peroxide [6].…”