Simultaneous Preconcentration of Fast Green FCF and Rhodamine B Using Deep Eutectic Solvent and Determination <i>via </i>High-Performance Thin Layer Chromatography

Karami, Forough; Shokrollahi, Ardeshir

doi:https://doi.org/10.1155/2023/8797355

Journal of Analytical Methods in Chemistry

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Abstract Introduction Materials and Methods Results and Discussion Conclusions Data Availability Additional Points Conflicts of Interest Authors’ Contributions Acknowledgments References Copyright Related Articles

Research Article | Open Access

Volume 2023 | Article ID 8797355 | https://doi.org/10.1155/2023/8797355

Simultaneous Preconcentration of Fast Green FCF and Rhodamine B Using Deep Eutectic Solvent and Determination via High-Performance Thin Layer Chromatography

Forough Karami¹and Ardeshir Shokrollahi¹

Academic Editor: Fábio R. P. Rocha

Received15 Aug 2023

Revised04 Nov 2023

Accepted14 Nov 2023

Published04 Dec 2023

Abstract

The aim of the current investigation is the development of a green, quick, easy, and accurate method for simultaneous preconcentration of fast green FCF (FG) and rhodamine B (Rh B) using a deep eutectic solvent (DES). Then, the high-performance thin layer chromatography (HPTLC) technique was used for the determination of analytes. Decanoic acid and tetrabutylammonium bromide were chosen as the components of DES. HPTLC analysis was performed on an aluminum plate silica gel 60 F₂₅₄. Methanol-ammonia and ethyl acetate were selected as the mobile phase. Scanning of the plates was accomplished by scanner 3. Effective parameters on the preconcentration process such as concentration of salt, volume of DES, stirrer time, and pH were investigated via central composite design (CCD). Data validation demonstrated good repeatability. The limit of detection for FG and Rh B was obtained as 0.08 and 0.01 µg·mL⁻¹, respectively. The enrichment factor for FG and Rh B was achieved as 7.43 and 10.77, respectively. The linear ranges for FG and Rh B were acquired as 0.10–1.20 and 0.05–1.20 µg·mL⁻¹, respectively. The preconcentration factor for both analytes was 21.66. Finally, the proposed method was successfully used for the quantitation of FG and Rh B in pastille and lipstick.

1. Introduction

Synthetic dyes have drawn considerable attention in different industries including food, paper, medicine, textile, and cosmetic [1] because of low cost and favorable appearance. In general, synthetic pigments influence psychological effects, which lead to loss of control, crying, increased sleeplessness, and other diseases [2]. Of these approaches, the consumption of food dyes in different applications should be limited. Rhodamine B (Rh B) as one of the synthetic dyes is known as a harmful compound for human health and used in various industries such as food, leather, textile, paper, printing, and plastic [3]. Due to the carcinogenic effects of Rh B on the eyes, skin, and liver, it is banned for use in the food industry [4, 5]. Fast green FCF (FG) as another synthetic dye is extensively used in the coating of candy, beverages, ice cream, health, and skin care products [6]. The toxicity and allergenic effects of FG had been published [7, 8]. It may also cause irritation of the eyes and skin [8].

Direct quantitation of FG and Rh B without specific pretreatment is problematic because of the matrix effects of other components and their low amounts in real samples. Therefore, preconcentration methods have been applied when it is difficult to detect trace amounts of analytes. The miniaturized form of liquid-liquid extraction entitled as liquid-phase microextraction (LPME) uses microliter volume to provide high extraction efficiency. LPME has some advantages such as economic extraction, rapid phase transportation, high capacity of extraction, and the facility of direct injection of samples into analytical instruments [9]. Numerous extraction methods including magnetic solid phase extraction [10, 11], solid phase microextraction [12, 13], hollow fiber liquid phase microextraction [14, 15], single drop microextraction [16], dispersive liquid-liquid microextraction [17], ultrasound-assisted LPME [18], and liquid-liquid microextraction [19, 20] had been reported for the extraction and determination of synthetic dyes. In recent years, there has been an increasing focus on the utilization of deep eutectic solvents (DESs) as a novel green solvent. These solvents were first introduced by Abbott et al. in 2004 [21]. DESs are made via the combination of a hydrogen bond acceptor (HBA) and a hydrogen bond donor (HBD) due to the formation of hydrogen bonds after heating at a temperature of 60–90 ̊C for 30 min to one hour [21]. The melting point of DES is lower than that of its constitutive component [22]. Some properties of DES including the degree of affinity for target components, less solubility, and good dispersion in aqueous media influence the extraction methodology [23]. DESs have been extensively used for extraction, separation, and preconcentration processes [24].

Numerous compounds have been proposed for the synthesis of DES. For instance, choline chloride or vitamin B₄ is introduced as the most used HBA, whereas amino acids, carboxylic acids, urea, ethylene glycol, glycerol, and sugars have been used as HBD [24]. DESs show the characteristic of high purity and eco-friendly [25], which have been used for the extraction and microextraction of synthetic dyes: simultaneous identification of eight synthetic dyes [26], determination of some red dyes [27], and determination of sunset yellow dye [28].

Various techniques have been proposed for the analysis of dyes such as spectroscopy [19, 29], high-performance liquid chromatography [30, 31], high-performance liquid chromatography-mass spectrometry [32], scanometry [33, 34], and thin layer chromatography (TLC) [35]. Among the different analytical techniques, high-performance thin layer chromatography (HPTLC) is known as a low cost, simple, and rapid technique that is appropriate for the comparison and separation of different components [36]. HPTLC has numerous advantages over other methods: simultaneous study of different compounds, automation, less solvent compared to other liquid chromatography methods, easy pretreatment, fast, and cheap analysis [37, 38]. Therefore, it can be considered as a green analytical technique [39].

As mentioned above, it is vital to use extraction systems employing environmentally friendly solvents to reduce the consumption of hazardous organic materials. Thus, in this investigation, a DES based on the combination of decanoic acid (DA) as a HBD and tetrabutylammonium bromide (TBAB) as a HBA was used for the simultaneous preconcentration of two synthetic dyes followed by HPTLC technique as the modern analytical instrument of TLC for the determination of dyes, which is a reliable and cost-effective technique. Additionally, central composite design (CCD) was applied as an efficient method to study the interactions between effective parameters and system response. The developed analysis is innovative in terms of the methodology for the simultaneous quantitation of artificial dyes and the used solvent for the extraction process.

2. Materials and Methods

2.1. Materials and Instruments

All chemicals and reagents were of analytical grade. DA, TBAB, sodium chloride, FG, Rh B, Quinoline Yellow, tartrazine, methanol (MeOH), acetonitrile (ACN), ethanol, ethyl acetate, ammonia, and aluminum plate silica gel 60 F₂₅₄ (20 × 20 cm) were purchased from Merck Company (Darmstadt, Germany).

Agilent Technologies Cary Series 100 UV/VIS Spectrophotometer was used for spectra acquisition. The chromatographic analyses were performed by Camag HPTLC, made in Switzerland, equipped with ATS4, scanner 3, and visualizer.

2.2. Preparation of DES

DES was prepared according to our previous report [40]. In brief, 2 mmol DA and 1 mmol TBAB were mixed and stirred at a temperature of 50°C until a clear liquid was attained (about 30 min).

2.3. Preconcentration Process

Stock solutions of FG and Rh B ( mg·mL⁻¹) were prepared in MeOH. To survey the preconcentration of dyes, different concentrations of sodium chloride, volume of DES, stirrer time, and pH were studied using CCD by the software package Design-Expert version 7.0.0 trial. The effective factors and condition of levels are presented in Tables 1 and 2, respectively. For each level, in a Falcon tube (15 mL), a definite concentration of salt (according to Table 2, for example, 0.350 mol·L⁻¹) was mixed with distinctive volume of dyes mg·mL⁻¹ (according to Table 2, for example, 390 µL) and the solution was made up to 13 mL via deionized water. Then, adjusting pH (according to Table 2, for example, 4.50) was performed and an appropriate volume of DES (according to Table 2, for example, 375 µL) was added to the Falcon tube. In the following, the mixture was stirred at desired time (according to Table 2, for example, 15 min). After finishing the stirrer time, the solution was centrifuged at 4000 rpm for 5 min. Next, the Falcon tubes were inserted in an ice beaker, resulting in the formation of a solid and thin layer on top of the solution, which was related to the preconcentrated dyes. This layer was separated using a spatula and diluted using MeOH before HPTLC analysis. The schematic preparation of this procedure is presented in Scheme 1.

2.4. Preparation of Real Samples

Lipstick and pastille were purchased from Shiraz City, Fars Province, Iran. The preparation of lipstick was carried out based on Yilmaz^’s et al. investigation with a little modification [29]. In brief, 0.899 g of lipstick was weighed in a 50 mL Falcon tube and 10 mL of ethanol was added. The sample was vortexed for 1 min, ultrasonicated for 30 min, and centrifuged for 20 min at 4000 rpm. In the next step, the supernatant was collected, diluted with a dilution factor of 50, and kept in a refrigerator for further experiments. In the following, 1.3 g of pastille was dissolved in 6 mL of deionized water. The solution was vortexed for 1 min, ultrasonicated for 30 min at a temperature of 70°C, and filtered using a PTFE filter.

2.5. Preconcentration of Real Samples

To extract chosen dyes using DES from real samples, 390 µL of lipstick (diluted solution) and 600 μL of supernatant solution of pastille were transferred to a Falcon tube. Then, 2.3 mL of NaCl (2 mol·L⁻¹) was added and after dilution using deionized water (13 mL), the pH of solution was adjusted (pH 4.64). Afterward, 378 μL of synthesized DES was added to the tube and the solution was stirred for 15 min. For the separation of phases, centrifugation was done at 4000 rpm for 5 min. In the following, the Falcon tube was kept in an ice beaker, which resulted in the separation of organic phase containing extracted dyes. Due to the high viscosity of DES, the obtained extraction phase was diluted by MeOH (600 μL) before HPTLC analysis.

2.6. Instrumental Conditions

Chromatographic analysis at room temperature and 20% humidity was accomplished by Camag HPTLC, made in Switzerland, equipped with ATS4, scanner 3, and visualizer. Before each analysis, the plate was washed using MeOH to remove any contamination. The preconcentrated dyes, in the form of band, were spotted by ATS4 under N₂ gas (5 bar pressure) on an aluminum plate silica gel 60 F₂₅₄ (20 × 20 cm) with a band length of 9 mm and a distance of 13.5 mm. 2.5 and 5 µL of preconcentrated and standard dyes were applied, respectively. Developing of the plates was done manually under the following conditions: MeOH-ammonia and ethyl acetate with a ratio of 20-20 and 60% v/v, respectively, as the mobile phase; chamber saturation time, 20.0 min; volume of mobile phase, 10 mL; and migration distance, 90 mm. Scanning of the plates was performed by scanner 3 to the following conditions: the wavelength of 620 nm and absorption mode for FG; the wavelength of 365 nm and fluorescence mode for Rh B; slit dimension, 6.00 mm × 0.40 mm, macro; scanning speed, 20 mm/s; data resolution, 100 µm/step; lamp W for FG; lamp Hg for Rh B. Finally, the image of plates was obtained by the visualizer at 366 nm and visible wavelengths. Recording of data was carried out via WinCATS software.

3. Results and Discussion

3.1. Optimization of Chromatographic Conditions

It is vital to improve some significant parameters including the volume of spots, time of tank saturation, type of mobile phase, migrating distance of solvent, and detection wavelength of analytes using HPTLC technique [41]. In the current research, among different spot volumes that had been loaded on an aluminum silica gel plate, the volumes of 2.5 and 5 µL for preconcentrated and standard dyes, respectively, were applied, which yielded the narrow bands. Also, among various band lengths (6, 8, and 9 mm), the band length of 9 mm was selected, which resulted in an appropriate band. In order to find a mobile phase that can separate two analytes with a good R_f, seventeen different mobile phases were investigated, which are described in Table 3. Finally, the best simultaneous separation for dyes of FG and Rh B was achieved using MeOH (20% v/v)-ammonia (20% v/v) and ethyl acetate (60% v/v) that resulted in R_f values of 0.11 and 0.70 for FG and Rh B, respectively. Before each analysis, tank saturation, as a main factor in planar chromatography, was performed for 20 min providing a uniform atmosphere to achieve equilibration for separation. Increasing the migration distance of solvent resulted in high resolution. Therefore, the solvent distance of 90 mm was chosen to obtain a good resolution. The HPTLC images of preconcentrated dyes are shown in Figure 1.

UV-VIS spectra of selected dyes were obtained using a spectrophotometer for spectra acquisition of FG and Rh B. By doing so, the detection of FG was carried out in an absorption mode at the maximum wavelength of the dye (620 nm). For the detection of Rh B, at first, scanner 3 was adjusted at the maximum wavelength of dye (545 nm) in an absorption mode, which formed an inappropriate signal. Hence, due to the fluorescence properties of Rh B, scanning of the plates was performed in fluorescence mode. The densitograms of preconcentrated FG in absorption mode at 620 nm and Rh B in fluorescence mode at 365 nm are presented in Figure 2. As shown in Figure 1, FG and Rh B were distinctly detected as red and yellow colours under 365 nm, respectively. Similarly, under visible light, FG and Rh B were separately identified as blue and pink spots, respectively. So, there is no interference between analytes.

(a)

(b)

3.2. Central Composite Design

As presented in Table 1, a CCD was applied to adjust four effective parameters including pH, concentration of salt, volume of DES, and stirrer time. 30 experiments were done based on the experimental design. Characteristics of each level are shown in Table 2. Analysis of variance (ANOVA) shown in Table 4 expresses the significance of designed model and the main interactions among variables. The amounts of F value (Table 4) show that the model for two dyes is significant.

ANOVA data for FG were obtained as follows: values of value less than 0.0500 indicate that the model terms are significant. In this case, A, B, C, D, AB, AD, BC, BD, A², B², C², and D² are significant terms. The F value for Lack of Fit (3.17) implies that the Lack of Fit is not significant relative to the pure error. The predicted R-Squared of 0.9942 is in agreement with the adjusted R-Squared of 0.9978 (Table 5) and shows a high dependence and correlation between the achieved and expected values of response. High value of adequate precision as the signal to noise ratio is desirable. Hence, the value of 92.664 indicates an adequate signal. Finally, a quadratic equation is achieved via the coefficient values, which is as follows:where R_FG is the area of FG and A, B, C, D are considered as the pH of mixture, volume of DES, concentration of salt, and stirrer time, respectively.

Similarly, ANOVA data for Rh B were achieved as follows: values of value less than 0.0500 indicate that the model terms are significant. In this case, A, B, C, AB, AC, BC, BD, CD, A², B², C², and D² are significant terms. The F value for Lack of Fit (0.64) implies that the Lack of Fit is not significant relative to the pure error. The predicted R-Squared of 0.9909 is in agreement with the adjusted R-Squared of 0.9955 (Table 5). High amounts of R² (Table 5) approve that there is a high correlation between the expected and experimental data [42]. A high value of adequate precision (89.016) indicates an adequate signal. Finally, a quadratic equation is achieved via the coefficient values, which is as follows:

In order to understand the acquired results, the graphs of three-dimensional response surface are shown in Figure 3. To find the best response, the desirability parameter of 1.0 was selected as the maximum response. Of these approaches, the pH value of 4.64, salt concentration of 0.35 mol·L⁻¹, DES volume of 378 μL, and stirrer time of 15 min were chosen as the optimum points.

3.3. Optimization of Variables

As mentioned before, a CCD was applied for preconcentration of two dyes to acquire the best conditions and assay the main variables and their interactions. As depicted in Figure 3, the volume of DES in the preconcentration of selected dyes was studied in a range of 225–525 μL by CCD. Because of the satisfactory properties of DESs, they have been extensively applied instead of conventional organic solvents and ionic liquids in the extraction, separation, and preconcentration processes [43]. An appropriate extraction agent in liquid phase microextraction processes plays a significant effect for the effective separation of analytes because the DES provides a stable phase (due to nonvolatile solvent), which improves the extraction efficiency [22]. Moreover, in liquid phase microextraction methods, the volume of extraction agent (solvent) is considered as one of the most significant factors, which extremely affected the extraction efficiency and preconcentration factor [22]. In the current investigation, high amounts of DES lead to a significant response because of increasing droplets of DES. Meanwhile, a low volume of DES reduces extraction efficiency, probably due to the decrease in DES droplets making insufficient separation. It seems that when the volume of solvent is high, the available droplets are more resulting in an increase of interaction between two phases.

The application of an inorganic salt affects the extraction efficiency [44]. This is because it causes variations in ionic strength and provides an inert medium that is suitable for the extraction process. In the current study, the concentration of sodium chloride (as the salt) was investigated in the range of 0.0–0.7 mol·L⁻¹. As presented in Figure 3, a low signal was detected, when no salt was used. The reason for this is that the DES cannot be absolutely removed from the solution [44]; therefore, small amounts of analytes are collected and extraction efficiency will decrease. Also, high concentration of sodium chloride can reduce the extraction efficiency, maybe due to the decrease in distribution coefficients of the target compounds that can change the ionic strength of the solution [44]. Thus, the concentration of 0.35 mol·L⁻¹ was selected to achieve good separation.

In an extraction process, pH is an essential parameter, which can increase extraction efficiency. In the current research, the effect of pH was investigated in a range of 2.10–6.91 by CCD. At acidic media, the carboxylic group of Rh B (pK_a = 4.1) [45] is not ionizing and approximately forms a neutral molecule, which leads to pass from the aqueous phase to the extraction phase and results in high efficiency [29]. At low acidic pH for FG, the anionic groups of SO₃^- convert to the neutral form (SO₃H) resulting in high extraction efficiency. In addition, the presence of DA (pK_a = 4.9) and salt makes approximately an inert medium, which is suitable for an effective extraction.

Another investigated parameter was stirrer time, which was studied in the range of 5–25 min. The amount of stirrer time between DES and analyte solution influences the extraction efficiency due to providing a mass transfer of the target compound from aqueous media to the extraction phase and also formation of a good emulsification [22]. When the phases of organic and inorganic are mixed at high stirrer time, a partial separation of two phases happens, which results in decreasing extraction efficiency [42]. Consequently, the stirrer time of 15 min was achieved as the best contact time.

According to the presented reasons above, the pH value of 4.64, salt concentration of 0.35 mol·L⁻¹, DES volume of 378 μL, and stirrer time of 15 min as the best conditions for simultaneous preconcentration of FG and Rh B were proposed by CCD.

3.4. Method Validation

Validation of an analytical method is important to confirm the reliability and suitability of a designed method [46]. Therefore, the figures of merit such as linear range, calibration curve, correlation coefficient (r), limit of detection (LOD), preconcentration factor (PF) [34], enrichment factor (EF) [34], and repeatability were investigated under the optimized conditions as presented in Table 6. Calibration curves of the two dyes were plotted using the peak areas of FG and Rh B against desired concentrations in definite ranges. High correlation coefficient for the two dyes (r = 0.998) indicated good linearity. The practical LODs of 0.08 µg·mL⁻¹ for FG and 0.01 µg·mL⁻¹ for Rh B were measured at the lowest amount of dyes to be indicated. The repeatability parameter, indicating the precision of the method, for FG and Rh B was calculated as the relative standard deviation percent (RSD %) for five replicate determinations of a definite concentration. The parameters of PF and EF were evaluated under the optimized conditions based on the equations of 3 and 4, respectively [40]. The value of PF (21.66 for both dyes) in an extraction process indicates that how much the analyte has been concentrated. A higher value of PF shows a more efficient extraction, which can be favorable for an analytical method in terms of improving LOD or reducing interference effects from other matrix components. Similarly, the high value of EF (7.43 for FG and 10.77 for Rh B) displays a more efficient extraction. EF is used to assess the effectiveness of an extraction process and to evaluate the contaminants in different samples.

According to our statistical data, the applied procedure has some benefits: excellent correlation coefficient, high PF, and good repeatability.

3.5. Effect of Interference Components

Interference effects of Quinoline Yellow and tartrazine as synthetic dyes were studied under optimized conditions. The percent relative error for FG-Quinoline Yellow, FG-tartrazine, Rh B-Quinoline Yellow, and Rh B-tartrazine was achieved as 3.79%, 6.62%, 8.79%, and 4.59%, respectively, that were less than 10%, indicating no serious effects on the separation and assay of dyes using DES [31].

3.6. Analysis of Real Samples

Pastille and lipstick were used as real samples. A standard addition method was applied to plot the calibration curves. The achieved data, HPTLC images, and three-dimensional chromatograms for quantitation of analytes are shown in Table 7 and Figures 4 and 5, respectively. As shown in Figure 4, the value of R_f for FG and Rh B in real samples is similar to those in preconcentrated dyes (Figure 1), which proves the existence of FG and Rh B in pastille and lipstick, respectively. In addition, the achieved data are compatible with three-dimensional chromatograms (obtained from scanner 3) of FG and Rh B, which are depicted in Figure 5. For each dye, the analysis was performed in triplet. Finally, the amounts of FG and Rh B in real samples were found to be 0.01 and 0.55 mg·g⁻¹, respectively. The recovery was calculated using the equation of 5 [40], which showed that the matrix effect was not important in the extraction process. Also, the results revealed acceptable recoveries for the quantitation of both analytes (FG and Rh B) in real samples.

(a)

(b)

3.7. Comparison of Method with Other Investigations

The proposed method was compared to other investigations for the analysis of FG and Rh B. As shown in Table 8, the current research provided reasonable results. Compared with other studies, RSD % and PF amounts were higher than or comparable to values achieved using other analytical methods, indicating that the current study can be sensitive and accurate for the simultaneous analysis of FG and Rh B.

4. Conclusions

In the current research, an innovative microextraction method (DES) combined with the HPTLC technique for the preconcentration, separation, and determination of two synthetic dyes including FG and Rh B was established. The selection of a mixture of MeOH (20%), ammonia (20%), and ethyl acetate (60%) as the mobile phase in HPTLC analysis displayed good separation (different R_f values) between FG and Rh B. The best conditions for the simultaneous preconcentration of FG and Rh B were investigated using CCD, achieving a pH value of 4.64, salt concentration of 0.35 mol·L⁻¹, DES volume of 378 μL, and stirrer time of 15 min. The quantitative analysis for two dyes showed good repeatability (RSD < 5%), high correlation coefficient (r = 0.998 for two dyes), low interference, and excellent PF (21.66 for both dyes) and EF (7.43 for FG and 10.77 for Rh B) parameters, which can be suitable for simultaneous detection of FG and Rh B in food, medicine, textile, and cosmetic industries. Also, the analysis of real samples revealed a low serious matrix effect in this procedure. The main advantage of the developed analysis is the application of a green and environmentally friendly extraction solvent. To the best of our knowledge, the proposed method is the first study for the simultaneous preconcentration of FG and Rh B using DES and the determination of dyes via HPTLC as a rapid, green, and cheap analytical method. Finally, it can be concluded that due to the possible risk of synthetic dyes for the environment and human health, the developed process is favorable for routine analysis in different industries because of its sensitivity, simplicity, time saving, and expenditure.

Data Availability

The data used to support the results of this study are included within the article.

Additional Points

Highlights. (i) Deep eutectic solvent as a green solvent was successfully applied for simultaneous preconcentration of fast green FCF and rhodamine B. (ii) Deep eutectic solvent coupled with high-performance thin layer chromatography provides low limit of detection for analytes. (iii) High-performance thin layer chromatography is an appropriate technique for simultaneous determination of preconcentrated fast green FCF and rhodamine B.

Conflicts of Interest

The authors declare that they have no conflicts of interest.

Authors’ Contributions

Forough Karami was responsible for methodology, preparation of original draft, conceptualization, visualization, and investigation. Ardeshir Shokrollahi was responsible for supervision, conceptualization, review, and project administration.

Acknowledgments

The authors gratefully wish to thank the support of Yasouj University, Iran, and Shiraz University of Medical Sciences, Shiraz, Iran, for this study.

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Copyright © 2023 Forough Karami and Ardeshir Shokrollahi. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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