Extractive separation of 4- hydroxybenzoic acid from aqueous solution using nontoxic and conventional solvents
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
References (69)
- et al.
Plant polyphenols: structure, occurrence and bioactivity
Stud. Nat. Prod. Chem.
(2003) - et al.
Profiling C6–C3 and C6–C1 phenolic metabolites in Cocos nucifera
J. Plant Physiol.
(2005) - et al.
Phenolic compounds and total antioxidant potential of commercial wines
J. Food Chem.
(2003) - et al.
Antioxidant capacity and phenolic profile of table olives from the Greek market
J. Food Chem.
(2006) - et al.
Biophenolic components of olives
J. Food Res. Int.
(2000) - et al.
Anti-sickling, analgesic and anti-inflammatory properties of 3,5-dimethoxy-4-hydroxybenzoic acid and 2,3,4 trihydroxyacetophenone
J. Phytomedicine
(2000) - et al.
Phenolic compounds in plants and agri-industrial by-products: antioxidant activity, occurrence, and potential uses
J. Food Chem.
(2006) - et al.
Preservatives in cosmetics: regulatory aspects and analytical methods
- et al.
Photo-Fenton treatment of water containing natural phenolic pollutants
Chemosphere
(2003) - et al.
Extractive separation of protocatechuic acid using natural non-toxic solvents and conventional solvents
Chem. Data Collec.
(2018)
General design methodology for reactive liquid–liquid extraction: application to dicarboxylic acid recovery in fermentation broth
J. Chem. Engg. and Process.: Process Intensif.
Reactive extraction of lactic acid using alamine 336 in MIBK: equilibria and kinetics
J. of biotechnol.
Estimation of equilibrium parameters using differential evolution in reactive extraction of propionic acid by tri-n-butyl phosphate
Chem. Eng. Processing: Process Intensif.
Back extraction of propionic acid from loaded organic phase
Chem. Eng. Sc.
Solvent developments for liquid-liquid extraction of carboxylic acids in perspective
Sep. purify. Technol.
Effect of temperature on equilibria for physical and reactive extraction of protocatechuic acid
Heliyon
Reactive separation of protocatechuic acid using tri-n-octyl amine and di-(2- ethylhexyl) phosphoric acid in methyl isobutyl ketone
Sep. and Purif. Technol.
Extraction of lactic acid by phosphonium ionic liquids
Sep. Purif. Technol.
Reactive extraction of acetic acid and propionic acid using supercritical carbon dioxide
J. of Supercritical Fluids
Reactive extraction of carboxylic acids using organic solvents and supercritical fluids: A review
Sep. Purif. Technol.
Reactive extraction of picolinic and nicotinic acid by natural non-toxic solvent
Sep. Purif. Technol.
Relative basicity approach for separation of α-toluic acid with triglycerides of fatty acids by reactive extraction
J. Ind. Eng. Chem.
Antioxidant effect of natural phenols on olive oil
J. Am. Oil Chem. Soc.
Antimicrobial and antioxidant properties of phenolic acids alkyl esters
Czech J. Food Sc.
Therapeutic potential of dietary phenolic acids
J. Adv. Pharma. Sci.
Mechanism studies of LCP synthesis
J. Polymers
4-Hydroxybenzoic acid-a versatile platform intermediate for value-added compounds
Appl. Microbiol. Biotechnol.
Hydroxycarboxylic acids, aromatic, Chap. Ullmann's Encyclo. of Ind
Chem
Elucidating the effects of laccase on the physical properties of high-Kappa kraft pulps
Prog. in Biotechnol.
Wine waste treatment methodology
Int. J. of Food Sc. and Tech.
Ozonation kinetics of phenolic acids present in wastewaters from olive oil mills
Ind. Eng. Chem. Res.
Method for increasing total production of 4- hydroxybenzoic acid by biofermentation
United States Patent
Enhancing bioethanol fermentation through removal of acetic acid using liquid-liquid extraction
Open Access Dissertations
Cited by (6)
Extraction equilibrium of vanillic acid using natural solvents
2023, Chemical Data CollectionsEfficacy of natural oils and conventional chemicals in the physical extraction of 4-hydroxybenzoic acid from aqueous solution
2022, Journal of the Indian Chemical SocietyCitation 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.
Experimental investigation of reactive extraction of p-hydroxybenzoic acid using TOA in toluene, petroleum ether and MIBK
2023, Separation Science and Technology (Philadelphia)Reactive Extraction of 4 Hydroxybenzoic Acid Using Tri- n-Butyl Phosphate in Toluene and Petroleum Ether at 298 K
2022, Journal of Chemical and Engineering Data
- 1
4-Hydroxybenzoic acid (4-HBA)
- 2
distribution coefficient (KD)
- 3
extraction efficiency(E%)
- 4
partition coefficient (P)
- 5
dimerization constant (D)