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Scientific Reports volume 14, Article number: 23286 (2024 ) Cite this article methyl ethyl cellulose
Highly functional and robust biobased materials are still in research to produce valuable composites for various applications. The literature shows the gap of new raw biobased materials in market which can functionally tuned and structurally modified for development of 2d/3d architectures. Thus, in the present study, very cheap, easily available agricultural waste, pineapple leaf fiber (PL-raw) was used for the isolation of microcrystalline cellulose (PL-MCC) and further functionalized using upscaled chemical approach to carboxymethyl microcrystalline cellulose (PL-CMMCC). Very advanced techniques like Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), X-ray diffraction analysis (XRD), and differential scanning calorimetry (DSC) served to characterize the raw material, high crystalline PL-MCC, and modified carboxy methyl MCC. FTIR determined presence of different absorbed peak at approximately 1620.2 cm−1, and at 1423.8 cm−1, carboxyl groups were assigned to PL-CMMCC. On the other hand, the XRD findings verified that PL-CMMCC’s crystalline structure has decreased. Analysis by SEM revealed a damaged surface morphology for PL-CMMCC. Following chemical treatments, the EDX analysis revealed that each fiber sample contained a highly pure cellulose elemental composition. Thus, results explain the utilization of agricultural waste, pineapple leaf fiber to high valuable products like highly crystalline PL-MCC, in addition further modification of PL-MCC could leads to formation of highly functional material that could be used for other applications too in future.
The search for robust, functional, high strength, soluble and active biobased materials is still pending in the field of additives manufacturing, composites productions, high strength applications etc1. The production of biobased functional micro/nano materials could solve this problem and it is the thrust area in the current scenario. Recently, microfibrillated cellulose (MFC), cellulose nanocrystals (CNC) and nanofibers (CNF) were chemically/mechanically isolated from wood2,3,4,5,6,7 and further modified to more superior materials and then used for highly advanced technologies/applications. For example, fully biobased affinity membranes were produced using various functionalized microfibrillated cellulose having active groups of hydroxyls (-OH), carboxylic (-COO), phosphate (PO43−) and methyl (CH3)2,3.
Therefore, study of more sustainable biomaterials has grown rapidly in recent years. Indeed, agricultural waste is the most prevalent and limitless crystalline biopolymer that took place naturally in the world, and there is substantial interest in exploiting it as the main source of cellulose. Maize stalks, orange peel, sugarcane bagasse, rice and wheat straw, soybean pods, banana rachis, mulberry bark, and coconut fiber have all been investigated as potential sources to produce cellulose micro/nano materials1,2,3,4,5,6,7.
Every year, tropical fruit companies generate lignocellulose waste in the form of pineapple leaf fiber (PL-raw), albeit only a small portion is now used in energy production and as biomass resources7,8. PL-raw is hard to decompose because of its high lignin and cellulose content, which contributes to its adverse environmental effects7,9. PL-raw is made up of 70–85% sugar polymer cellulose, the larger part being crystalline. The monomers that make up hemicellulose are arabinose, mannose, galactose, glucose, and xylose, which account for 6–19% of the total composition. Because it has an abundance of cellulose and a sharp microfibrillar angle, it makes microfibrils with a high tensile strength. Lignin accounts for 4–15% of the remainder, followed by wax at 4%, ash at 1–5%, and minerals in very small quantities. On average, it contains 11–15% water vapor9. It generates microfibrils with strong tensile strength because it contains a lot of cellulose and has a steep microfibrillar angle (14 °C)7,8,9. The lignin and hemicellulose matrix that encompasses the cellulosic plant fiber, is linked to crystalline forms by intramolecular and intermolecular hydrogen bonding and strikes in an amorphous form, explaining the situation rapid heat deterioration. Because of these linkages, CMMCC of PL possesses better mechanical characteristics as well as is considered to have excellent aptitude strengthening in composite elements4,8,9.
Therefore, transforming cellulose onto its derivatives is required prior to its use in the food industry. Carboxymethyl cellulose (CMC) also acknowledged as Na-CMC, is among most common variants and is utilized for a variety of applications. CMC is generated through chloroacetic acid and hydroxide cellulose reaction, and is a straight-line polymer, long-chain, and excellent affinity with water10,11. According to some articles, CMC may be composed from a diverse of cellulosic sources, including natural cellulose, paper sludge, wood waste, cotton liners, and fibers. Finding more affordable alternatives to make CMC has generated a lot of attention12,13,14but still, it is difficult to find the one step reaction for the isolation of MCC from PL. Indeed, various recipes in literature are responsible for less yield and less purity of isolated MCC from such high lignin content raw materials. In addition, due to the less solubility of MCC, it is not suitable to use it in fully water-based system11,12.
Therefore, the goal of this study is to produce highly functional cellulosic micro/nano materials having high functionality, strength, yield, and purity. Furthermore, it should be soluble in water and is entirely dependent on water to produce highly valuable materials/products. Thus, PL-raw was used in this study to fulfil these goals. A very easy, reproducible, and scalable chemical procedure was adapted for the isolation of PL-MCC. Furthermore, to make it soluble in water, MCC was chemically modified to carboxymethyl microcrystalline cellulose (PL-CMMCC) via a carboxymethylation reaction with sodium hydroxide using chloroacetic acid. Examples of the obtained PL-CMMCC were shown by means of Fourier Transform Infrared spectroscopy (FTIR), X-ray diffraction (XRD), Thermogravimetric analysis (TGA), and Differential scanning calorimetry (DSC), as well as by means of Field Emission Scanning Electron Microscopy (FESEM) and Energy Dispersive X-ray Particle Size Analysis (EDX/PSA). In addition, isolated cellulosic functional materials could be used to produce highly valuable products like additives, composites, adsorbents etc. Furthermore, the obtained results would be useful for the fabrication of micro/nano functional materials-based composite for real applications. The produced composites could be used for the packaging, water treatment (functional membranes), additives manufacturing, transportation use etc.
Pineapple leaf (PL) were sourced from a plantation in Johor, in the southern region of Malaysia. PL was composed of 70–85% cellulose, 4–15% lignin, 4% wax and approx. 1–5% ash, indeed minerals were in very low quantity. The pineapple varieties being used is Ananas cosomus, which is a member of the Bromeliaceae family (after the Josapine variety). NaClO2 (80%), NaOH, Na2CO3, KBr, H2SO4 (95–98% w/v), and glacial acetic acid (MO, USA) had been provided by Sigma-Aldrich. Nylon fabric was purchased from local marke having average pore size in the range of 500–800 μm.
This experimental setup was found to be ideal for generating white pineapple leaf fiber (PL-bleach) through the greatest elimination of lignin admixture, and this treatment was carried out on pilot scale using 500 mL of 2% NaClO2 (acidified with 5 mL C2H4O2) over the course of 2 h at 80 °C with continuous stirring. After removing the lignin-containing filtrate, the NaClO2-treated fiber substance has been retrieved through vacuum filtration using filtered water and nylon fabric (pore size approx. 500–800 μm) at 0.45 MPa. The fiber was then subjected to acid hydrolysis for depolymerization, following which the cellulose and hemicellulose components were swollen in 500 mL of NaOH (5%) at 80 °C for 5 h. After being treated with NaOH, the recovered fiber residue was neutralized using purified water to neutral pH and filtered through nylon cloth until it turned white. Additional acid hydrolysis treatment was carried out at 80 °C for 30 min applying 2.5 M HCl solution to depolymerize the fiber into particulates. The mixture was quenched with ten times its volume of cold distilled water to neutralize acidic reaction, and then it was centrifuged (5000 rpm for 10 min). The pH of the mixture was adjusted to 3.0 by adding 1 M HCl during the process. After being filtered and dried, the soft pulp-like structure of the acid-treated fiber (PL-MCC) was obtained (Fig. 1).
The microcrystalline cellulose (PL-MCC) was transformed to carboxymethyl microcrystalline cellulose (PL.-CMMCC) following the modified method15. The microcrystalline cellulose (15 g), isopropanol (IPA) (450 mL), and 40% w/v NaOH (50 mL) were stirred continuously for an hour at 50 °C while being mixed. Mixture was then mixed with an chloroacetic acid/IPA mixture (18 g/18 mL), agitated for the next 30 min, and placed in an oven for 3.5 h at 55 °C. After that, mixture’s liquid component was removed by centrifugation (5000 rpm for 10 min). After mixing in 225 mL of methanol, glacial acetic acid was used to neutralise the fibre. After that, mixture was rinsed five times with 225 mL of 70% v/v ethanol, followed by 225 ml of 95% v/v methanol. Finally, attained CMMCC product was dried for 12 h at 55 °C in an oven before being stored in a sealed container at room temperature for further use (Fig. 1).
Several cutting-edge approaches were employed for the identification of isolated PL-MCC and functionalized PL-CMMCC. The main aim was the understanding the rection conditions in the final properties of isolated cellulosic materials.
The IR spectra of manufactured PL-MCC and PL-CMMCC samples have been recorded using FTIR instrument (Model: FTIR-8900, Shimadzu, Japan). The pellets were prepared by crushing approximately 0.2 mg of PL-CMMCC samples with 2 mg KBr. Wavenumbers between 5000 –400 cm−1 were used to evaluate transmission. The spectra were carried out from accumulating 16 scans at a 4 cm−1 resolution over a region of 4000 –500 cm−1.ara>
A Bruker D8 Advanced Germany X-Ray Diffractometer producing by using CuKα radiation at 30 mA and 40 kV. Each sample’s diffraction patterns were continuously scanned from 10–50° with a speed of 2°/min.
The surface characteristics were studied using FESEM; Zeiss Sigma, Germany for all raw PL, PL-MCC, and extracted PL-CMMCC. Before being examined, the samples were vacuum coated with an Au layer. To examine their elemental configuration, an EDX test was performed using a voltage of 20 kV with a working distance of 14.5–15.5 mm. Using Malvern Mastersizer 2000 device, the samples’ particle size was analyzed.
Each fiber sample’s thermal stability was evaluated with TGA/SDTA 851e model Mettler-Toledo International Inc., Columbus, OH, USA. TGA was performed at 30–900 °C with 10 °C/min heating rate in nitrogen purge environment. In the meantime, DSC was examined using DSC 822 analyzer at heating rate of 10 °C/min between 30 and 600 °C (Mettler-Toledo International Inc., USA).
In our prior work, we reported an empirical method for calculating crystallinity index (which expresses the relative degree of crystallinity) from XRD spectra without first subtracting the base line14. Crystallite size (L) was determined for the (101), (10i), (002), and (040) crystallographic planes by subtracting corresponding Bragg angle from the baseline in spectra, stated by Chen et al14.,. The degree of subtitution was calculated by dissolving 0.5 g of MCC or CMMCC that had been dried at for 24 h in 100 ml purified water. Methyl red was used as guideline to titrate a 20 ml sample of each solution with 0.1 N sulfuric acid. The mixture was boiled and titrated to a second, more precise endpoint after first one was achieved. The DS of both materails was calculated by Eqs. (1) and (2) given below
Where, b is volumn of 0.1 N sulfuric acid used (ml) and G is pure mass of MCC and CMMCC (g).
The flow of all experiments performed to isolate MCC and further modified to CMMCC is shown in Fig. 1. The isolation of MCC from high lignin pineapple raw PL-raw was explored in very detail, indeed, the chemical reaction was followed to produce PL-MCC, the high crystallinity (crystallinity index 95.2%) was an indication of high purity and yield of isolated PL-MCC. The yield of PL-MCC was about 32% as calculated manually after dry weight. In our previous study, cellulose nanocrystals were isolated from industrial waste (cellulose sludge) and very low (14%) yield was reported5. Furthermore, the chemical reaction used for the isolation of PL-MCC is reproducible and could be used for pilot scale production (Table 1).
The image explains the various step used for the isolation of materials. Furthermore, all terminologies used for isolated materials is also shown in the image.
The modification of PL-MCC to PL-CMMCC was performed using chemical reaction with some modification, isolated PL-CMMCC was less crystalline, decrease in the crystallinity was recorded from 95.2 to 69.4%, this indicates the further breakdown of crystalline structure of cellulose. Furthermore, it has also been indicated that the produced PL-CMMCC was more soluble in water compared to MCC. Furthermore, the degree of substitution (DS) was also increased from 0.4 to 0.45 from PL-MCC to PL-CMMCC. In an article, degree of substitution was calculated for the surface functionalization of PL-MCC to carboxymethyl cellulose and the obtained results were in the agreement of our studies.
Morphology of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC were investigated through FESEM examination (Fig. 2a-d). The raw PL-Raw sample (Fig. 2a) exhibited a flawless surface with no holes or else fractures and a solid structure; nonetheless, the cellulose exhibited the presence of tiny fibre structures. The microstructure of the samples changed as the concentration of NaOH was expanded. The treated fibres of PL-Bleach (Fig. 2b) and PL-MCC (Fig. 1c) have turned into tiny fibre with smooth surface morphology (Fig. 2d). When the PL-CMMCC underwent treatment with 40% NaOH, its polymer chain began to degrade, causing PL-CMMCC’s structure to crack and deform (Fig. 2d). Defibrillation of cellulose powder was aided by presence of high concentration of NaOH, indicating that PL-CMMCC could only have been formed under those conditions. This result was consistent with that observed with PL-MCC derived from rice and cassava starch.
FESEM micrographs of (a) PL-Raw, (b) PL-Bleach, (c) PL-MCC, and (d) PL-CMMCC samples. It can see seen easily that the changes in the surface morphologies could be seen easily in with respect to the chemical degradation.
Figure 3 depicts the distribution of particle sizes of fibre samples, and Table 2lists the analysed data. The sample of PL-Raw has the highest size distribution of 564.78 μm. Meanwhile, the size was reducing from PL-Raw to PL-Bleach due to the disintegration of cellulose fibril and removal of lignin and hemicellulose. Despite both PL-MCC and PL-CMMCC have the relatively same size distibution around 200 μm, the PL-CMMCC (196.7 μm) sample has slightly smaller size comparing with PL-MCC (205.6 μm)15.
Particle size distribution of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples.
Table 2 further discussed the elemental analsysis of raw leaf (PL-raw) and isolated materials i.e. PL-Bleach, PL-MCC and PL-CMMCC. As shown in Table 1. The main elements available in the raw material are C, O, Mg, K, Ca and Na. the highest availability of reported for O i.e. 56.80%. furthermore, only three main elaments (C, O and Ca) are repoted after bleaching and it could be easily supported by literature16. In a published article16, the bleached cellulose was produced using pulp as starting material and the elemental analysis was performed, the increase in carbon and decrease in oxygen was reported as discussed in current stsudy. Indeed, one fold decrease in oxygen was reported and its could be due to the impact of chemicals on elements. Additionally, further decrease in carbon (61–54%) and increase in oxygen (38–45%) was reported for MCC isolation (Table 2), same fundings were repoted in our previous published article17. The change in elements after modification (MCC to CMMCC) is further supported ny another publihsed article18.
Figure 4shows EDX spectra of samples of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC. Each fibre clearly had oxygen and carbon peaks as its primary elements, which is what cellulose is composed of. Also, the EDX test showed that all fibre samples had pure cellulose after being treated with alkali, bleaching, acid, or carboxymethylation16.
EDX spectra of (a) PL-Raw, (b) PL-Bleach, (c) PL-MCC, and (d) PL-CMMCC samples.
The fiber characteristics of each sample were examined using FTIR spectroscopy. In Fig. 5, the differences between the FTIR spectra of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC are shown. The main differences were observed between 1000 cm1 and 1900 cm-1. The peak intensities of absorption bands at 1514.2, 1605.2, 1638.5, and 1740.1 cm-1 decreased from PL-Raw to PL-CMMCC samples.
A wide retention band at 3350 cm-1 was caused by stretching of hydroxyl group, instantaneously linked to hydrogen bonds within and between molecules. Furthermore, structural vibrations and C = O stretching of carbonyl groups were responsible for maximum intensity at 1514 cm-1, proving the involvement of PL-MCC. In addition, prominent peak at 1249 cm-1was assigned to C-O-C stretching at β-glycosidic bonds. These structural alterations and peak shifting proved the formation of PL-CMMCC16.
The band at 2924.1 cm-1 associated with C-H bending vibration, and both PL-MCC and PL-CMMCC samples exhibited large absorption band at 3434.9 cm-1 due to stretching vibration of OH group. A significant and intriguing absorption peak at 1620.2 cm-1 is consistent with COO-group bending vibrations, and absorption maximum at 1423.8 cm-1 is attributed to COO-salts. The bands that are located at 1329.3 cm-1 and 1112.7 cm-1 are thought to be caused by C-O-C bending vibrations and OH stretching, respectively. β-glycosidic linkage of cellulose was noticed and identified at 894 cm-116.
FTIR pattern spectra of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples.
XRD analysis is employed to analyze the amount of crystallinity present, such as cellulose, by attributing it to its semi-crystalline structure in origins. The scattering arrangements of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples are displayed in Fig. 6. Crystalline phases are represented by the peaks, while amorphous phases are shown by the baseline. The XRD approach forecasts that the peaks will be large due to the tiny crystallites in cellulose granules. This idea says that very small crystals with flaws cause more diffraction. The PL-CMMCC diffraction arrangements showed that the crystal structures of the novel cellulose were breaking down (Fig. 6). All the distinct peaks of cellulose have just about vanished and been replaced by an amorphous region. Thus, PL-CMMCC has superior solubility, since decreased crystallinity corresponds to super solubility12,13. Alkaline solution is added to the cellulose molecules during the carboxymethylation reaction. When cellulose granules grow in size, they exert a force on neighboring crystalline cellulose molecules, distorting their shape. Swelling causes their double-helical area to uncoil or detach, as well as the disintegration of their crystal structures13.
XRD pattern of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples.
Figure 7 depicts the TGA curves of the respective samples. All samples lost mass during the 50–132 °C temperature range due to evaporation of remaining hydrate and volatile compounds (Fig. 7a). Above 200℃, the early degradation temperature of PL-Bleach and PL-MCC was higher than that of PL-Raw. The remarkable heat resistance of PL-Bleach and PL-MCC was likely due to their high cellulose content. PL-CMMCC showed a lower early degradation temperature than PL-MCC, which might be attributed to its softer structure13.
In addition, PL-MCC exhibited remarkably high peak degradation temperature, which reflected highly crystalline cellulose structure (Fig. 7b). The decrease in peak degradation temperatures of PL-CMMCC may be attributes the presence of amorphous constituents. In addition, the peak degradation grew more pronounced from PL-Raw to PL-CMMCC, indicating that the PL-CMMCC sample contained purer cellulose compartment. Meanwhile, lower weight loss was revealed by PL-MCC as compared with PL-CMMCC. This was due to flame retard behavior of cellulose crystals within PL-MCC sample. The relatively high peak degradation temperature of PL-CMMCC at around 352.7 °C also proved that it has great capability to resist high temperature14.
(a) TGA and (b) DTG curves of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples.
The thermal property of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples were evaluated with DSC, while the DSC curves are presented in Fig. 8. The crystallizing temperature (Tc) of PL-Raw was 227.5 °C, PL-Bleach was 215.1 °C, PL-MCC was 241.2 °C, and PL-CMMCC was 243.9 °C, respectively. This shift in melting point is caused by the carboxymethyl side group’s abnormalities, which interfere with crystallisation and raise the melting point4,11,19.
DSC pattern of PL-Raw, PL-Bleach, PL-MCC, and PL-CMMCC samples.
In this study, we report the key results of an etherification reaction involving monochloroacetic acid, sodium hydroxide, and ethanol to produce PL-CMMCC from pineapple leaf fibre. In the FTIR spectrum, a new absorbed peak appeared at 1620.2 cm-1, which corresponds to vibrational stretch of COO- group, second peak at 1423.8 cm-1 was attributed to salts of carboxyl group in PL-CMMCC. The XRD results showed that structure of PL-CMMCC was less crystalline after synthesis process. Since native cellulose peaks changed into an amorphous structure, they are now almost impossible to observe. The SEM evaluation revealed disintegrated individual structure of PL-CMMCC powder. When the samples were exposed to 40% NaOH, the MCC polymer chain violated, which caused the surface of the PL-CMMCC powder to be cracked and deformed. The EDX analysis justified that each fiber sample composed highly plain cellulose elemental composition after respective chemical treatment process. In addition, the DSC curves for both PL-MCC and PL-CMMCC powders were fairly flat, indicating a stable thermal behaviour. Consequently, the attained PL-CMMCC output has potential application in pharmaceutical and food additives industry in near future. Furthermore, these functional material scould be easily used for some valuable product developments in future.
The datasets used and/or analysed during the current study available from the corresponding author on reasonable request.
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The authors would like to extend their gratitude to King Saud University (Riyadh, Saudi Arabia) for funding this research through Researchers Supporting Project number (RSP2024R117). Authors also thankful to United Arab Emirates University for Funding this work through Grant No: 12N233.
Applied Medical Science Department, Community College, King Saud University, P.O Box 10219, Riyadh, 11433, Saudi Arabia
Department of Chemical and Petroleum Engineering, Collage of Engineering, United Arab Emirates University, P.O Box 15551, Al Ain, Abu Dhabi, UAE
Mohammad Jawaid & Basim Abu-Jdayil
Department of Research, Development and Technology, Alfa Laval Nakskov A/S, Stavangervej 10, 4900, Nakskov, Denmark
Laboratory of Biopolymer and Derivatives, Introp, Universiti Putra Malaysia, Serdang, 43400, Malaysia
Department of Chemical and Environmental Engineering, Malaysia-Japan International Institute of Technology (MJIIT), Universiti Teknologi Malaysia, Jalan Sultan Yahya Petra, Kuala Lumpur, 54100, Malaysia
Department of Wood Technology, Faculty of Applied Science, MARA University of Technology, Jengka, Pahang, 26400, Malaysia
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Data curation, H.F. A.M. and M.J.; Formal analysis, H.F. and M.J.; Funding acquisition, H.F., M.J., M.H. and M.M.N. Project administration, H.F., M.J., Z.K., M.H. and A.M.; Writing—original draft, H.F., Z.K. and M.J.; Writing—review & editing, S.N.S, M.J., Z.K., M.H., M.M.N. and A.M. All authors have read and agreed to the published version of the manuscript.
Correspondence to Mohammad Jawaid or Zoheb Karim.
The authors declare no competing interests.
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Fouad, H., Jawaid, M., Karim, Z. et al. Preparation and characterization of carboxymethyl microcrystalline cellulose from pineapple leaf fibre. Sci Rep 14, 23286 (2024). https://doi.org/10.1038/s41598-024-73860-4
DOI: https://doi.org/10.1038/s41598-024-73860-4
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