Elsevier

Chemical Data Collections

Volume 36, December 2021, 100782
Chemical Data Collections

Extractive separation of 4- hydroxybenzoic acid from aqueous solution using nontoxic and conventional solvents

https://doi.org/10.1016/j.cdc.2021.100782Get rights and content

Abstract

4-hydroxybenzoic acid (4-HBA)1 is potential antidiabetic, anticancer, antioxidant, antifungal, cardioprotective etc. 4-HBA is worth to be recovered as it has bright applications in pharmaceutical, cosmetics and plastic industries. The experiments were performed for the separation of 4-HBA from its aqueous solution using nontoxic solvents; sesame oil, canola oil and conventional solvents; benzene, toluene and petroleum ether. The equilibrium for this physical extraction experiment was evaluated and the parameters like distribution coefficient KD2, % extraction efficiency E%3, partition coefficient P4 and dimerization constant D5 were found and correlated with different physicochemical properties of solvents. The results for KD and E% were found as: sesame oil (0.49,33.24%) > canola oil (0.23,18.85%) > petroleum ether (0.092,8.32%) > toluene (0.09,8.25%) > benzene (0.08,7.49%).

Introduction

Phenolic acids also known as phenol carboxylic acids are present in all plant derived food items. The word Phenolic acid is self-explanatory about the existence of phenol and carboxylic acid functional group. They are secondary metabolites. They can be classified in two major classes; C1-C6 (hydroxybenzoic acid) and C3-C6 (hydroxycinnamic acid). 4-Hydroxybenzoic acid (4-HBA) belongs to C1-C6 (hydroxybenzoic acid) class. It is present naturally in various food items, some of them are; coconut, raspberry, gooseberry, fennel, anise and pulses [1,2]. The raw materials used for making wine and olive fruits contain 4-HBA hence it is found in the effluent of winery industry and olive oil mill [3], [4], [5].

Being a phenolic acid, 4-HBA has various physiological properties like, antioxidant, antibacterial, antifungal, antimutagenic, antisickling, Cardioprotective, Antidiabetic, Anticancer [6], [7], [8], [9], [10]. Owing to such medicinal properties 4-HBA has wide pharmacological applications. Different valuable compounds derived from 4-HBA are, liquid crystal polymers (LCPs) which are modern high-tech polymers having very bright applications in thermoplastic industry [11,12], 4-hydroxyphenyl alcohol which is mainly used for the synthesis of cardiovascular drugs metoprolol [13] and the esters of 4-HBA, known as paraben, are potentially used as preservative in cosmetics and pharmaceutical products [14].

4-HBA could commercially be synthesized by Kolbe-Schmitt reaction using potassium phenoxide and Carbon dioxide [15]. Process of biosynthesis is also used for the production of 4-HBA.

4-HBA exists in the waste stream of different food processing units, winery industry, olive oil mill and pulp and paper industry [16] and as it biodegrades very slowly, deteriorates the quality of soil if dumped on the land [17]. Keeping in view the excellent physiological properties and different attractive applications of 4-HBA, the recovery of 4-HBA from the effluent will not only be environment friendly but also economically intensifying. The conventional techniques for the removal or recovery of 4-HBA are degradation by ozone [18], ion exchange using resin [19], liquid- liquid Extraction [20], adsorption [21] and photo Fenton [22]. All these techniques face different limitations like less conversion, time consuming, not much effective for the dilute solutions, energy demanding, high cost and generation of toxic by-products [23,24].

Reactive extraction is an economical, time saving, clean and suitable for the dilute solutions [25,26] hence various researchers have employed reactive extraction for the successful separation of carboxylic acids like dicarboxylic acid [27], lactic acid [28], picolinic acid [29], propionic acid [30], [31], [32], glycolic acid [33], levulinic acid [34], rosmarinic acid [35] and other carboxylic acids [36, 37, 38]. Some phenolic acids like Gallic acid [39], [40], [41], [42], protocatechuic acid [23,[43], [44], [45], [46], [47]] and 4-HBA [48], [49], [50] have also been recovered successfully using reactive extraction. Ample work has been done taking different ecofriendly solvents like ionic liquids [51], super critical fluids [52,53] and natural solvents [54,55] as organic phase.

This work intends to explore the physical extraction parameters for the separation of 4-HBA using nontoxic solvents and chemical solvents and to check their feasibility. Two nontoxic natural solvents; canola oil and sesame oil [55,56,57] two nonpolar aromatic solvents; benzene and toluene and one aliphatic hydrocarbon; petroleum ether was taken.

Section snippets

Chemicals

4-HBA (98% pure) was purchased from HIMEDIA. Benzene (99% pure) and Toluene (99.5% pure) were procured from Central Drug House Pvt Ltd. Petroleum ether (98% pure) was obtained from SDFCL. Sesame oil was obtained from Patanjali Ayurveda Ltd. India and Canola oil was purchased online from Borges Agriculture & industrial edible oils, Spain. The chemicals and oils used are listed in Table 1.

Experimental methodology

The solute 4-HBA was dissolved in distilled water to make aqueous solution (0.016- 0.035 mol/lit). The

Result and discussion

In this work two natural oils; canola oil and sesame oil and three conventional solvents; benzene, toluene and p-ether have been used for the extractive separation of 4-HBA from its aqueous solution. The effect of canola oil, sesame oil, benzene, toluene and p-ether on distribution coefficient (KD) and % extraction efficiency (E%) is shown in Table 2, Table 3, Table 4, Table 5., Table 6. and 6 respectively. Different physical extraction parameters like KD, E%, partition coefficient (P) and

Conclusion

The extractive separation of 4-HBA from its aqueous solution was experimented in this work using different natural nontoxic and chemical solvents. The assessment of the extraction work was done on the basis of different extraction parameters like KD, P, E% and D. Sesame oil found to give maximum average extraction efficiency of 33.24%. Both the natural oils gave extraction better than aliphatic hydrocarbon and aromatic solvents. The natural oils ensure the advantage of non- toxicity as well.

In

Declaration of Competing Interest

The authors declare the following financial interests/personal relationships which may be considered as potential competing interests

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  • Cited by (6)

    • Efficacy of natural oils and conventional chemicals in the physical extraction of 4-hydroxybenzoic acid from aqueous solution

      2022, Journal of the Indian Chemical Society
      Citation Excerpt :

      Some of the physicochemical properties are reported in Table 8. For the purpose of extractive separation of 4-HBA, the natural oils and chemicals used so far are mustard, sunflower, soyabean oil (present study), canola and sesame oil [50]; 1- octanol, MIBK (present study), benzene, toluene and p-ether [50]. The natural oils yield low extraction efficiency and distribution coefficient.

    1

    4-Hydroxybenzoic acid (4-HBA)

    2

    distribution coefficient (KD)

    3

    extraction efficiency(E%)

    4

    partition coefficient (P)

    5

    dimerization constant (D)

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