Preparation 2-Hydroxy-1-naphthaldehyde cross-linked magnetic Fe3O4@chitosan- polyacrylamide nanocomposite for removal of everzol black from aqueous solutions

doi:10.21203/rs.3.rs-2743563/v1

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Preparation 2-Hydroxy-1-naphthaldehyde cross-linked magnetic Fe₃O₄@chitosan- polyacrylamide nanocomposite for removal of everzol black from aqueous solutions

https://doi.org/10.21203/rs.3.rs-2743563/v1

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published 30 Jun, 2023

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In this study, new 2-Hydroxy-1-naphthaldehyde linked magnetic Fe₃O₄/chitosan-polyacrylamide nanoparticles were prepared. The synthesized nanoparticles were characterized by (FT- IR), X-ray diffraction (XRD), Scanning Electron Microscopy (SEM), vibrating Sample Magnetometry (VSM) and Termogravimetric Analysis (TGA). The 2-Hydroxy-1-naphthaldehyde modified magnetic Fe₃O₄/chitosan-polyacrylamide nanoparticles were used as an effective adsorbent for removal of Everzol black from aqueous solutions by batch adsorption procedure. The effects of important parameters on the surface absorption process of Everzol black dye, including pH, contact time, adsorbent dosage and initial dye concentration were studied. The Langmuir and Freundlich adsorption models were used to describe adsorption isotherms and constants.

Physical sciences/Chemistry

Physical sciences/Chemistry/Inorganic chemistry

Physical sciences/Chemistry/Materials chemistry

The extreme use of colorant substances for decades by industries led to decline of water bodies in the world [1, 2]. For example, industries related dyeing, plasticization and paper making are used a lot of water and chemicals to color the products and consequently, they produce a large amount of colored wastewater, which if they are not treated before entering the environment and waters, they will cause many problems, including disrupting the photosynthesis of waters and ecosystems [3]. Moreover, their complex molecular structure and aromatic rings are toxic and carcinogenic, which can affect human health, water microorganisms, and the environment [4, 5]. Nanofiltration membranes [6], ion exchange [7], electrochemical oxidation [8], photo-catalytic degradation [9] and adsorption are methods that have been used to remove colors and pollutants from wastewater. However, most of the above mentioned methods are ineffective due to factors such as operational costs, secondary wastes, environmental effects and related problems, efficiency and applications [10]. Among these methods, adsorption is more superior than other methods due to low initial cost, easy design, suitable flexibility and high efficiency [11]. In this field, many absorbents including Activated carbon, Nanoclays, Plant biomass and Natural absorbents has been used and reviewed [12]. Among these absorbents, activated carbon is the most suitable absorbent to remove all kinds of pollutants. However, the high price, lack of recycling and reusing have limited the application of this absorbent [13]. Recently, magnetic nanoparticles have attracted much attentions because they have grate magnetic properties such as large surface area, low toxicity, chemical stability, good biocompatibility and biodegradation [14, 15]. It can also be separated from aqueous solutions easily and quickly by using an external magnetic field without requiring tedious filtration or centrifugation [16]. Chemical or physical change of the surface Fe₃O₄ nanoparticles with some surfactants or polymers is required for improving the adsorption performance of Fe₃O₄ nanoparticles [17]. polysaccharides such as chitosan and its derivatives are more interesting, since the use of chitosan based adsorbents is one of the best ways to remove the colors and ions of heavy metals even at low concentrations [18]. Chitosan mainly contains poly2-deoxy-D-glucose which is a biopolymer derivative and has known polymer properties so it has attracted scientist’s attentions because of biocompatibility, biodegradability and nontoxic properties [19–22]. Because chitosan contains high amounts of amine and hydroxyl groups, it has a very high absorption ability to remove many types of metals such as copper, chromium, silver, platinum and lead physically and chemically. However, in order to improve the absorption properties of adsorbents, much attention has been paid to the design and synthesis of new adsorbents. For example, magnetic chitosan complex coated on the surface Fe₂O₃ has been used for remove alizarin red from water environments [23]. Wang et al. employed magnetic polydopamine-chitosan nanoparticles as adsorption material for the removal of Methylene blue and Malachite green from aqueous solutions [24]. Zhu et al. synthesized the chitosan-modified magnetic graphitized multi-walled carbon nanotubes for the effective removal of Congo red from aqueous solution [25]. In this study, new 2-Hydroxy-1-naphthaldehyde linked magnetic Fe₃O₄/chitosan-polyacrylamide nanoparticles (Fig. 1) were synthesized. The nanoparticles prepared was applied for the removal of the Everzol black from aqueous solution. In addition to the effects of various parameters such as pH, adsorbent dosage, initial dye concentration and contact time on adsorption behavior were studied. Also, the equilibrium isotherms were determined and explained.

Characterization of the modified silica gel

FT-IR analysis

FT-IR spectra of Fe₂O₃, chitosan, acrylamide, Fe₃O₄@CS@Am and Fe₃O₄@CS@Am@Nph are shown in Fig. 2. The characteristic peaks (blue line) of the Fe₂O₃ appeared at 582 and 628 cm^− 1 corresponding to Fe-O stretching vibration 1628 and 3426 cm^− 1 and the peaks at 1628 and 3426 cm^− 1 assigned to OH bending vibration of Fe₂O₃ respectively [26]. For chitosan (red line), a broad band around 3425 cm^− 1 belongs to amino (NH₂) and hydroxyl (OH) groups. Beside the peaks at 2916 and 1381 cm^− 1 assign to C-H and C-N respectively [27]. The FTIR spectra of acrylamide (green line) demonstrated absorption peak at 1674 cm^− 1 showed the presence of C = O group of amides [28], also the peaks at 3352, 3192 and 2812 cm^− 1 attributed to NH and CH stretching vibration respectively.

XRD analysis

X-ray diffraction of Fe₃O₄@CS@Am@Nph composite particles is shown in Fig. 3. The characteristic XRD peaks for Fe₃O₄@CS@Am@Nph observed at 2θ = 30.3^◦ (220), 35.6^◦ (311),43.5^◦ (400), 53.5^◦ (422), 57.3^◦ (511) and 62.5^◦ (440) belong Fe₃O₄ nanoparticles. Beside the peaks at 10.4 and 20.4^◦ are related to chitosan structure [29–31]. The average size of Fe₃O₄@CS@Am@Nph composite particles is also estimated via Debye–Scherer equation D = 0.9λ/βcosθ (D is the average size, λ is the X-ray source wavelength (1.54 Å), β is the full width at half maximum (FWHM) of the diffraction peak and θ is the Bragg’s angle) to be approximately 193 nm.

SEM analysis

Scanning electron microscopy (SEM) is used to characterize the morphology and size of Fe₃O₄, Fe₃O₄@CS@Am and Fe₃O₄@CS@Am@Nph particles. As shown in Fig. 4 the morphology of nanoparticles obtained nearly spherical shape. Furthermore, the size of Fe₃O₄, Fe₃O₄@CS@Am and Fe₃O₄@CS@Am@Nph nanoparticles are relatively uniform and the average diameter are 26–32, 107–165 and 155–173 nm respectively.

TGA analysis

The TGA curve of the Fe₃O₄@CS@Am@Nph is shown in Fig. 5. From the plot, the weight loss of Fe₃O₄@CS@Am@Nph at a temperature from 28^◦C to 226^◦C is 7.23% and 2.84% respectively, which is attributed to the removal of water from the surface of the nanoparticles [32]. For Fe₃O₄@CS@Am@Nph composite particles, weight loss between 226^◦C to 600^◦C (73.71%) was observed which is attributed to the decomposition of the anchored organic polymers of the adsorbent.

Magnetization analysis

The magnetic moment of the prepared magnetite nanoparticles was measured over a range of applied fields between 10000 and − 10000 Oe. The magnetization curves of the Fe₃O₄, Fe₃O₄@CS@Am and Fe₃O₄@CS@Am@Nph at room temperature are shown in Fig. 6. The VSM results indicate coating the surface of the magnetite nanoparticles with acrylamide, chitosan and 2-Hydroxy-1-naphthaldehyde leads to a decrease in the saturation magnetization. This is due to the presence of acrylamide, chitosan and 2-Hydroxy-1-naphthaldehyde on the surface of Fe₃O₄ nanoparticles which may generate a magnetically dead layer so any crystalline disorder within the surface layer cause to a significant decrease in the saturation magnetization of nanoparticles [33]. The saturation magnetization values for the Fe₃O₄ particles, Fe₃O₄@CS@Am and Fe₃O₄@CS@Am@Nph nanomaterials were 67, 7and 6 emu g^− 1, respectively.

Sorption studies of selected dyes

Effect of adsorbent dosage

One of the important factors which affects adsorption processes is adsorbent dose since it determines the capacity of adsorbent for a given initial concentration of dye solution [34]. In this study, the influence of adsorbent dose on adsorption removal of everzol black dye was studied by using different amounts of sorbent (20, 40, 60, 80 and 100 mg) in 40 mL of 100 mg/L at 25 ^◦C for 30 min. Figure 7 showed effect of adsorbent dosage on the percentage removal of dye. The results showed that the % sorption of the everzol black dye increased by increasing the dosage of adsorbent. With the increase in dosage of Fe₃O₄@CS@Am@Nph nanocomposite, the percentage removal of everzol black dye increased from 58.25 to 94.87. percentage removal increase can be related to the increased surface area of the adsorbent and availability of more adsorption sites.

Effect of initial dye concentration

The Effect of initial concentration of everzol black on adsorption of it on Fe₃O₄@CS@Am@Nph nanocomposite were studied in different initial concentrations of dye between 10 and 100 mg/L with keeping constant the other parameters. As result of Fig. 8 illustrates, the percent of dye removal decreases with increase in dye initial concentration from 10 to 100 mg/L. This may be due to the increase of enough number of active sites of dye molecules for binding on the surface of the adsorbent. The percentage removal of everzol black decreases from 93.2 to 25.4%.

Effect of contact time

The effect of contact time on adsorption of everzol black the surface of Fe₃O₄@CS@Am@Nph nanocomposite were studied at room temperature with the different contacting time at 10 and 20 min. Figure 9 shows effect of contact time on the percent removal of everzol black. As it can be seen in Fig. 9, by increasing the contact time percent adsorption of everzol black on Fe₃O₄@CS@Am@Nph was increased.

Effect of initial pH solution

The pH plays a crucial role in the adsorption of dye onto the adsorbent. Indeed, the pH affects the adsorption process through the degree of ionization, the surface charge of the adsorbent, or the speciation of the adsorbate. In this study, the effect of initial pH on the sorption of everzol black onto Fe₃O₄@CS@Am@Nph nanocomposite were studied at different values from 2 to 12. For this experiment, 0.1 M NaOH and 0.1 M HCl solutions were used to adjust the pH of the solution. The effect of pH on the percentage removal of everzol black by Fe₃O₄@CS@Am@Nph is shown in Fig. 10. As it is seen in Fig. 10, in acidic conditions the amount of adsorption is increased that can be due to electrostatic attraction between positive charge of amino groups of chitosan and negative charge of sulfonate groups of the everzol black dye.

Adsorption isotherms

Adsorption isotherm is a method to investigate the relationship between the adsorbed amount in the liquid phase on adsorbent in equilibrium and constant temperature. In fact, the adsorption isotherm describes the interaction between the adsorbent and adsorbed surfaces. Therefore, it is always considered as a fundamental factor for determining the absorbent capacity and optimizing the absorbents. In the present study, Langmuir and Freundlich isotherm models were used to obtain the isotherm parameters for adsorption of everzol black onto Fe₃O₄@CS@Am@Nph nanocomposite. Investigating the experimental data obtained from adsorption in equilibrium with theoretical models and obtaining the relationship between them provides important information for the best possible design of an absorbent system. Langmuir adsorption isotherm: In this model, there is no interaction among adsorbed molecules and adsorption process happens on homogeneous surfaces, showed in below equation [35]:

$$\frac{{\text{C}}_{e}}{{q}_{e}}=\frac{1}{{\text{K}}_{\text{L}}.{q}_{m}}+\frac{{\text{C}}_{\text{e}}}{{q}_{m}}$$

where, C_e is the equilibrium concentration of the dye solution (mg/L), q_e (mg/g) is the amount of dye adsorbed, q_m is the value of monolayer adsorption capacity in Langmuir model and K_L: constant value of Langmuir (mg/L). The Langmuir plot for the adsorption of everzol black onto Fe₃O₄@CS@Am@Nph nanocomposite at different temperatures is shown in Fig. 11. Freundlich isotherm model is the more for the adsorption of components dissolved in a liquid solution, it is assumed that: First, the adsorption is monolayer and chemical, and second, the energy of the adsorption sites is not the same, ie the adsorbent surface is not uniform [36]:

$$\text{L}\text{n} {q}_{e}=\text{L}\text{n} {\text{K}}_{\text{f}}+\left(\frac{1}{\text{n}}\right) \text{L}\text{n} {\text{C}}_{\text{e}}$$

K_F and n are experimental constants where K_F is adsorption capacity at unit concentration (L/mg) and n shows the intensity of adsorption. The 1/n values can be classified as irreversible (1/n = 0), favorable (0 < 1/n < 1) and unfavorable (1/n > 1). Calculation of K_F and n in Freundlich model for Fe₃O₄@CS@Am@Nph nanocomposite shown in Fig. 12. Also, the separation factor (R_L) was calculated by the following equation:

$${\text{R}}_{\text{L}}=\frac{1}{1+{\text{K}}_{\text{L}}.{\text{C}}_{0}}$$

The values of R_L can illustrate the shape of the isotherm to be either unfavorable (R_L>1), linear (R_L=1), favorable (0 < R_L<1) or irreversible (R_L=0). The values of Langmuir and Freundlich parameters and the regression coefficients R² of the adsorption of everzol black onto Fe₃O₄@CS@Am@Nph are given in Table 1. According to Table 1, the value of R_L was obtained in the range of 0 < R_L<1, that showed adsorption of the everzol black on Fe₃O₄@CS@Am@Nph was favorable. The maximum monolayer adsorption capacity (qm) calculated by Langmuir model was found to be 63.69 and regression coefficient value is 0.9959.

Table 1

Langmuir and Freundlich isotherms parameters and correlation coefficients for the adsorption of everzol black onto Fe₃O₄@CS@Am@Nph
Langmuir isotherm parameters				Freundlich isotherm parameters
q_m (mg/g)	K_L (L/mg)	R_L	R²	K_F (L/mg)	n	R²
63.69	0.49	0.019	0.9959	28.87	3.38	0.9635

In this study, 2-Hydroxy-1-naphthaldehyde linked magnetic Fe₃O₄/chitosan-polyacrylamide nanoparticles were prepared. The synthesized nanoparticles were characterized by (FT- IR), XRD, SEM, VSM and TGA. The modified Fe₃O₄/chitosan-polyacrylamide nanoparticles was used successfully as an effective sorbent for the removal of everzol black dye from aqueous solutions. The effects of various parameters such as adsorbent dose, solution pH, initial dye concentration and contact time on the adsorption process were investigated. The Langmuir and Freundlich isotherm models were applied to analyze the experimental data. The maximum adsorption capacity of Fe₃O₄@CS@Am@Nph for everzol black was 63.69 mg/g at 25 ^◦C.

Chemicals and reagents

Ferric chloride hexahydrate (FeCl₃.6H₂O) with 98% purity, ferrous chloride tetrahydrate (FeCl₃.4H₂O) with 98% purity, absolute ethanol, 2-Hydroxy-1-naphthaldehyde, Chitosan, glycerol with 99% purity and ammonia (NH₃) with 25% purity were purchased from Merck, Germany. Everzol Black (chemical formula = C₂₆H₂₁N₅Na₄O₁₉S₆, Molecular weight (g/mol) = 991.82, λ_max = 436 nm) was purchased from the Textile Factory. The chemical structure of Everzol Black is shown in Fig. 13.

Instrumentation

FT-IR spectra (Shimadzu prestige-21) were used to determine the identity of the as prepared nanoparticles and to characterize the coated Fe₃O₄ nanoparticles. X-ray powder diffraction measurements were performed using an X-ray diffractometer (XRD) (Perkin Elmer) at ambient temperature. The surface morphology of the silica-supported ligands was identified with a scanning electron microscope (LECO SEM, Michigan, USA). Magnetic measurements were performed by means of the vibrating sample magnetometery method, using a VSM 7407 magnetometer, at room temperature. Thermogravimetric analysis (TGA) was performed using a Perkin Elmer thermogravimetric analyzer. UV-visible spectra in the 200–1000 nm range were obtained in DMF solvent on a Perkin Elmer Lambda 45 spectrophotometer. A Jenway model 4510 pH-meter was used for pH measurements by use of a combined electrode. An ultrasonication probe (Karl Deutsch, Germany) was used to disperse the nanoparticles in the solution.

Preparation of magnetite nanoparticles (Fe₃O₄)

The magnetic nanoparticles were prepared according to [37] with minor modifications. Briefly, FeCl₃.6H₂O (11.68 g) and FeCl₂.4H₂O (4.30 g) were dissolved in 200 mL deionized water under nitrogen gas with vigorous stirring at 85 ^◦C. Then, 20 mL of 30% aqueous ammonia was added to the solution. The color of the bulk solution changed from orange to black immediately. The magnetic precipitates were washed twice with deionized water and once with 0.02 mol/L sodium chloride. The washed magnetite was stored in deionized water at a concentration of 40 g/L.

Preparation of Fe₃O₄@CS@Am nanocomposite

To a suspension of the Fe₃O₄ nanoparticles (0.35 g) in DI water (100 mL), chitosan (CS) (2 g) and acrylamide (1 g) were added. The mixed solution was ultrasonically dispersed for 30 min. The polymerization reaction of acrylamide was initiated by K₂S₂O₈, and the reaction was allowed to proceed for 12 h at 80^◦ C under nitrogen atmosphere and mechanical stirring. The resulting solid was magnetically separated, washed with hot toluene several times to remove the unreacted ligands and dried under vacuum.

Preparation of Fe₃O₄@CS@Am@Nph nanocomposite

To a suspension of the Fe₃O₄@CS@Am nanoparticles (1 g) in ethanol (150 ml), 2-Hydroxy-1-naphthaldehyde (Nph) was added (0.5 g). The reaction mixture was refluxed for 48 h under nitrogen atmosphere. The Fe₃O₄@CS@Am@Nph nanocomposite were separated by an external magnet, washed with distilled water and ethanol then dried in vacuum at 60^◦ C for 24h.

Adsorption experiments

Synthesized nanoparticles were used removal of everzol black dye from aqueous solutions. Various parameters such as initial concentration, contact time, adsorbent dose and pH on adsorption were studied. For performing the experiments, solution of 1000 mg/L of everzol black was prepared in deionized water and diluted to obtain the desired concentrations of dye. Different amounts of nanoparticles, varying from 20 to 100 mg, was suspended in a series of 40 mL dye solution with concentrations varying from 40 to 120 mg/L using 50 mL glass flasks. For suitable times from 10 to 20 min the suspensions were stirred and also the effect of solution pH on dye removal was investigated through adjusting by 0.01 N HCl or NaOH solutions. The nanoparticles adsorbent was separated from aqueous solution by an external magnetic field. The concentration of the everzol black was analyzed by UV-spectrophotometer at λ_max 600 nm. The amount of the dye adsorbed onto adsorbent (qe in mg/g) and the percentage of the dyes removed from the solution (R in %) were calculated from the equations:

$$\text{q}\text{e}=\frac{(\text{C}0-\text{C}\text{e})}{\text{M}}. \text{V}$$

$$\text{%}\text{R}=\frac{(\text{C}0-\text{C}\text{e})}{\text{C}0}. 100$$

where, C₀ and C_e are the initial and equilibrium concentration of dye in solution (mg/L), respectively. V is the initial volume of the dye solution (L) and M is the mass of adsorbent used (g).

Data availability

All data supporting the conclusions of this research article are included within the manuscript.

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Preparation 2-Hydroxy-1-naphthaldehyde cross-linked magnetic Fe₃O₄@chitosan- polyacrylamide nanocomposite for removal of everzol black from aqueous solutions

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