Reactive extraction of 6‐aminopenicillanic acid with aliquat‐336: Equilibrium and kinetics

Abstract

The reactive extraction of 6-aminopenicillanic acid (6-APA) from aqueous buffer solution has been studied using a liquid anion exchanger, tricaprylylmethyl ammonium chloride (Aliquat-336) in n-butyl acetate as the solvent. The extraction equilibrium constant and partition coefficient increase with increase in pH up to a limiting value of pH, beyond which extraction decreases due to coextraction of OH-and buffer anions and hydrolytic decomposition of 6-APA. The experimental data could be predicted from an equilibrium model which takes into account the ideal behaviour of the two liquid phases. The coextraction of the buffer anion under low pH conditions was found to be negligible. The extraction rate measured in a stirred cell of constant interfacial area appears to be dependent on the interfacial mass transfer of the reactive species as well as on the interfacial reaction through its dependence on the concentration of 6-APA in the aqueous and organic phases, respectively.On a etudie I'extraction reactive de I'acide 6-aminopenicillanique d'une solution tampon aqueuse a I'aide d'un echangeur d'anions liquide, le chlorure d'amrnonium tricaprylylmethyl (Aliquat-336) dans du n-butyl acetate coinme solvant. La constante d'equilibre d'extraction et le coefficient de partition augmentent avec le pH jusqu'a une valeur limitante du pH, au-dela de laquelle I'extraction diminue en raison de la coextraction de OH-et des anions tampons ainsi que de la decomposition hydrolytique de 6-APA. Les donnees experimentales peuvent etre exprimees a partir d'un modele d'equilibre qui tient compte du comportement ideal des deux phases liquides. La coextraction de I'anion tampon dans de faibles conditions de pH s'avere negligeable. I1 apparait que la vitesse d'extraction mesuree dan une cellule agitee de surface interfaciale constante depend du transfert de matere interfacial des especes reactives et de la reaction interfaciale par I'entremise de la concentration de 6-APA dans les phases aqueuse et organique respectivement.

Reactive extraction of N-acetylneuraminic acid—Kinetic model and simulation of integrated product removal

“…Scheme of the mechanism assumed for the extraction of GlcNAc, ManNAc and Neu5Ac. by ion transfer was subject to several publications since the 1980s [34][35][36][37][38][39][40]. The kinetic model used here to describe the reactive twostep extraction of the carbohydrates and pyruvate is based on a model published by Chan and Wang [41] for the reactive extraction of amino acids.…”

Reactive extraction of N-acetylneuraminic acid—A new method to recover neuraminic acid from reaction solutions

“…Pyruvate does not react with PBA prior to extraction with TOMAC. The deprotonated form of Pyr present in basic solutions is probably extracted directly by TOMAC like other organic acids [3,29,30]. The equilibrium constant K ex,Pyr can therefore be determined by plotting…”

Enzymatic Hydrolysis of Penicillin for 6-APA Production in Three-Liquid-Phase System

“…1). The purification procedure for 6-APA follows extraction with MIBK (methyl isobutyl ketone) at pH 2, concentration at pH 8, and precipitation of product 6-APA at pH 4 (the isoelectric point, IEP) [5]. There were several drawbacks existing in the aqueousv 6-APA route: The byproduct PAA would acidify the pH, which led to low enzymatic activity and stability in water [6].…”

“…Rindfleisch developed a hollow fiber membrane instrument to separate 6-APA from the enzymatic solution [10]. Bora used Aliquat-336 in butyl acetate phase for recovery of 6-APA from the aqueous solution [5]. Wyss employed liquid-core capsules dispersed in water to extract PAA during the reaction [11].…”