Reactive extraction of 3-HP acid using tertiary and quaternary amines in decanol and comparison with its isomer 2-HP acid

Abstract : The carboxylic 3-hydroxypropanoic acid (3-HP, CAS number 503-66-2), has enormous potential as a platform molecule for the synthesis of bio-based polymers and the production of commercially valuable chemicals such as 1,3-propanediol, acrylic and malonic acid. In the actual environmental and economic context, there is an increased interest in the microbial production at a large industrial scale of 3-HP [1]. As for organic acid production, 3-HP concentration is suspected to exhibit inhibitory effects on the microorganism, thus leading to low productivity. A potential strategy to increase the performance of the bioconversion step and to recover 3-HP is to implement an integrated process, by which upstream bioconversion is combined to downstream extraction, namely " In Situ Product Recovery " (ISPR). Although there are currently no ISPR technique developed in the literature for the extraction of 3-HP, some patents suggest that processes which proved to be effective for the extraction of its positional isomer, 2-HP (lactic acid), could also be applied to 3-HP [2]. A promising technique that drew a lot of attention lately for the extraction of 2-HP is the reactive extraction in an organic phase containing an extractant [3]. In the present work, the reactive extraction of 3-HP was studied using tertiary trioctylamine and quaternary ammonium salt tri-n-octylmethylammonium chloride (Aliquat 336) as extractants, and n-decanol as diluent. Comparison was made with 2-HP acid. Impact of the aqueous phase pH and acid concentration as well as the amines concentration were addressed. Results showed that, although 3-HP was not extracted as efficiently as 2-HP, its reactive extraction by TOA under acidic conditions proved to be favorable. Indeed, the hydrophobicity and pKa differences between these two isomers had a significant impact on the performances of their reactive extraction. More importantly, extraction by a synergistic mixture of amines showed highly interesting apparent distribution coefficients over a wide range of pH values, including the optimal pH range for fermentation. The reactive extraction was also shown to be predominantly controlled by interfacial chemical reactions. Performing it in a membrane contactor provided a high interfacial area and allowed an optimized use of the extraction process potential. These pioneering results represent a potential breakthrough in understanding the specific mechanisms of 3-HP reactive extraction, prior to its implementation in an integrated extractive bioconversion process.
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Contributor : Claire Saulou-Bérion <>
Submitted on : Wednesday, July 19, 2017 - 2:35:10 PM
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  • HAL Id : hal-01565091, version 1



Marwen Moussa, Grégoire Burgé, Claire Saulou-Berion, Florent Allais, Violaine Athes-Dutour, et al.. Reactive extraction of 3-HP acid using tertiary and quaternary amines in decanol and comparison with its isomer 2-HP acid. 10th European Symposium on Biochemical Engineering Sciences (ESBES10) and 6th International Forum on Industrial Bioprocesses (IFIBIOP6), Sep 2014, Lille, France. pp.245 - 255856. ⟨hal-01565091⟩



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