Reactive extraction of cis,cis-muconic acid from aqueous solution using phosphorus-bonded extractants, tri-n-octylphosphineoxide and tri-n-butyl phosphate: Equilibrium and thermodynamic study
Graphical abstract
Introduction
Carboxylic acids are typically consumed on a broad scale through the pharmaceutical and chemical industries. cis,cis-Muconic acid (HccMA) is a two-carbon double-bonded dicarboxylic acid (shown in Fig. 1). It is chiefly used in biodegradable polymers, food, pharmaceuticals, and related industries [1].
Additionally, HccMA is an intermediate platform chemical for manufacturing the commodity important compounds (adipic and terephthalic acid) used in nylon 6,6 and polyester production [2]. Several ways have been described in the literature to obtain HccMA through microbial approaches [3], [4], from biorefinery process intermediates [5], fermentation medium [6], and so on [7], [8].
Global warming, limited oil reserves, and international resource competition have oriented chemical industries to search for environmentally sustainable and economical production processes for alternatives to fossil-derived fuel resources. There has been a considerable increase in the number of the chemical industries devising alternative courses based upon sustainable sources. Extensive efforts in this area were implemented in an attempt to generate carboxylic acids. Green-generation of carboxylic acids avoiding fossil fuels as a resource has already been achieved with fermentation technique. It became applicable for industrial applications. Due to the recent enhancements in strain engineering fermentation technique has been able to be more competitive with their petrochemical counterparts. In stu removal of toxic metabolite and cell recycling from effluents tolerate the inhibitory metabolite produced, leading to a successful production yield. Aerobic and anaerobic treatments are fermentation pathways applied depending on the cell growth conditions, energy consumption and carbon source requirements. Whilst the production of carboxylic acids has been accomplish successfully by fermentation technique,
the uptake of carboxylic acids remains to be unaddressed. Numerous techniques for separating carboxylic acids have been examined in the literature viz. nanofiltration [9], [10], adsorption [11], [12], crystallization [13], [14], and membrane [15].
Reactive extraction is a single-stage liquid–liquid extraction method relying on the acid-base formation in the organic phase. Reactive extraction with fermentation possesses intrinsic advantages such as reduced processing load and process cost, properly recovering the fermentation product in a single stage, and ease in acid removal. Additionally, depending on the continuous acid generation, the acidity of fermentation broth is increased which may pose a danger to the organisms. Removing acid produced regularly by an extractant has been a sensible approach to maintain appropriate pH in the fermentation broth [16]. Most of the extractants possess a high viscous characteristic. Since high viscosity brings lower solvation ability to complex, extractants are used along with solvents to support their physical properties by enhancing the extraction power. There has been an intensive research on the reactive extraction of levulinic [17], [18], [19], citric [20], [21], [22], propionic [23], [24], succinic [25], [26], lactic [27], caproic [28], nicotinic acid [29], [30] etc. The extraction equilibrium study of propionic acid by TBP with various solvents such as petroleum ether, n-heptane, and toluene was investigated by Keshav et al. The findings were assessed in terms of the equilibrium constant, distribution coefficient, extraction efficiency, and stoichiometric loading factor. The maximum recovery was achieved using a TBP + toluene combination with a distribution coefficient value of 3.444 [31]. Liquid-liquid equilibria of nicotinic acid by TOPO and TBP in n-heptane, n-decane, kerosene, methyl isobutyl ketone, and 1-decanol was studied by Kumar et al. to indicate the possible effect of the solvent, initial acid concentration, extractant type, and extractant proportion on the efficiency. The most prominent nicotinic acid extraction was achieved with TOPO dissolved in methyl isobutyl ketone at 0.10 kg.mol−1 nicotinic acid concentration [32]. Wasewar et al. investigated the distribution of acrylic acid between water and tri-n-butyl phosphate dissolved in paraffin liquid, toluene, and butyl acetate. A comparative study based on the physical properties of diluents was performed. They reported that TBP in inert diluents, toluene and paraffin liquid allows the possibility to reach higher distribution coefficients [33]. Keshav et al. studied the physical and chemical extraction of gallic acid by TBP in octanol, n-hexane, toluene, and ethyl acetate at isothermal conditions. Gallic acid extraction by TBP dissolved in n-hexane was found to be at maximum with a distribution coefficient value of 24; when TBP utilized at 1.516 kg.mol−1 concentration [34]. When it comes to the studies on the separation of HccMA from aqueous media or fermentation broth, there are only a few researches that have been described in the literature. Yoshikawa and the group developed a downstream process for the separation of HccMA including filtration, adsorption, precipitation, ion-exchange chromatography, and sedimentation stage. The results were achieved in high purity (95%) and high yield (90%). However, the high cost caused by the increased processing load was the primary drawback of a feasible downstream process for HccMA [35]. Zeiner et al. studied the reactive extraction of HccMA by water-insoluble and non-insoluble amines. They reported the high affinity of water-soluble amines to water may lead to bonds breaking between extracting agents and amines. Re-extraction of acid to the aqueous phase could result in a third phase formation. They suggested that modifiers like alcohols should be used in the extraction system to overcome a third phase formation by increasing the polarity of the organic phase [36].
Within this study, we aimed to search for a feasible downstream processing alternative to contribute to the separation of HccMA from fermentation media, resulting in an effective extraction system. Amines and organophosphorous compounds have been primarly extractants utilized for carboxylic acid separation from aqueous solutions that have been described in the literature. Considering their lower toxic effect on living beings, and their potantial to be more cost effective than amines, organophosphorous compounds have been utilized as extracting agent in this current study. This study focused on the reactive extraction of HccMA using organophosphorus compounds tri-n-octylphosphine oxide (TOPO) and tri-n-butyl phosphate (TBP) in organic solvents (alcohols, ketones, esters, and an aliphatic diluent), which has been undiscussed up to now. This study will be the first to investigate the effect of organophosphorousextractants on HccMA separation. TOPO and TBP were used as extractants to investigate the equilibria due to their high extraction capability and low solubility in water.
Section snippets
Materials and methods
The physicochemical properties of the chemicals used in this study are listed in Table 1, and all substances were utilized without additional treatment.
HccMA solution was prepared with deionized water at 0.007 kg.mol−1 concentration. Acid concentration used in the experiments was adjusted to be identical for its fermantation media. To constitute the organic phase, TOPO was diluted in ten different solvents (1-butanol, isoamyl alcohol, MEK, MIBK, diisobutyl ketone, isobutanol, n-hexane, dimethyl
Physical extraction results
Ion interactions between the acid molecules and solvent molecules are determinants for weak physical-bond formation between species. Carboxylic acids exist in general as monomers in the aqueous phase as the intermolecular hydrogen bonds formed by acid molecules are relatively weaker than those of hydrogen bonds exhibited by acid and water molecules. The hydrogen bonds weakness between the acid molecule and water molecule enhances accessibility to the acid molecule, i.e., permits easy access to
Conclusion
In this study, the physical and reactive extraction of HccMA with and without TOPO and TBP were presented in the diluents based on alcohols (1-butanol, isoamyl alcohol, isobutanol), ketones (MEK, MIBK, diisobutyl ketone), esters (dimethyl glutarate, ethyl propionate, DEC) and an aliphatic diluent (n-hexane). The results were evaluated in the light of distribution coefficient, extraction efficiency, loading ratio and equilibrium complexation constant parameters. Since the loading factor values
CRediT authorship contribution statement
Özge Demir: Visualization, Writing - original draft. Aslı Gök: Investigation, Writing - original draft. Hasan Uslu: Formal analysis. Şah İsmail Kırbaşlar: Conceptualization, Supervision, Funding acquisition, Writing - original draft.
Declaration of Competing Interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgment
The authors gratefully acknowledge the financial support received from BAP (Project No: FYL-2018-32214) from the İstanbul University-Cerrahpaşa.
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