Figure 5 - uploaded by Min Min Aung
Content may be subject to copyright.
Source publication
The non-edible seed oil of the Jatropha plant is a renewable and sustainable material to produce vegetable oil-based epoxy and epoxy acrylate as raw polymeric material. The objective of this study is to synthesis Jatropha seed oil-based epoxy and acrylate epoxy resins through conventional methods. An epoxy ring of Epoxidised Jatropha Oil (EJO) was...
Citations
... 110 The primary purpose of an inhibitor is to prevent homo-polymerization during the reaction process. Various inhibitors, such as 4-methoxyphenol, 111 hydroquinone, 112 and 4-tert-butylcatechol, 113 are employed in acrylation reactions. However, hydroquinone is frequently preferred in numerous studies due to its cost-effectiveness. ...
In the past ten years, there has been significant growth in the global 3D printing market, particularly in the development of natural and bio-based polymers. However, a major challenge is the limited availability of sustainable 3D printable resins capable of matching the performance of synthetic materials. This underscores the urgent need for the development of innovative and environmentally friendly resin materials. Herein, we introduce bio-based polymers, highlighting their recent advancements and offering a comprehensive overview of their diverse applications across various fields, including 3D printing. An area that has received less attention in this domain is polymers derived from vegetable oil (VO) or plant-based oil. Specifically, we thoroughly investigate the acrylation of epoxidized VOs and the subsequent formation of resins from these acrylates, which are essential materials for digital light processing (DLP), stereolithography (SLA), and extrusion-based 3D printing. The chemical modification of VOs, such as epoxidation and acrylation, is extensively explored, together with their respective types and applications. Furthermore, we delve deeply into the suitability of acrylate resins for 3D printing purposes. In conclusion, this review offers insights into the potential applications of 3D printed products utilizing materials derived from VOs.
... In addition, the ester-type carbonyl group band is observed at 1743.20 cm 1 , CC band at 1656.40 cm 1 , and the saturated chain CH bending vibrations at 1460.36 cm 1 and 1372.73 cm 1 , as well as the glycerol band at 1157.65 cm 1 . The presence of the previously described bands corresponds to the functional groups present in triglycerides, confirming the structure (Wong et al., 2017). The 1H NMR spectrum of the chicken fat ( Figure 1) shows signals at 5.2 and 5.5 ppm of the vinyl protons CCH; at 4.1 and 4.3 ppm of the glycerol protons H 2 CCOO; the protons adjacent to the carbonyl group (CH 2 COOCH) at 2.7 ppm; at 1.3, 1.6, 2 and 2.4 ppm of the CH 2 groups in the carbon chain, and at 0.8 ppm of the CH 3 groups. ...
Objetivo: Identificar las condiciones óptimas de síntesis de polioles a partir de grasa avícola por epoxidación e hidrólisis in situ. Diseño/metodología/enfoque: Se utilizó un diseño estadístico de superficie de respuesta tipo Box-Behnken se evaluó el efecto de los factores temperatura (60, 70 y 80 °C), catalizador (1, 2 y 3 % p/p), relación molar de dobles enlaces:ácido acético (1:1, 1:1,5 y 1:2) y tiempo (4, 6 y 8 h), sobre el índice de acidez de los polioles sintetizados. Resultados: Los espectros FTIR indicaron que en condiciones de reacción leve se generan grupos epóxido (827 cm-1) mientras que en condiciones de reacción severa se favorece la formación de grupos OH. Por lo tanto, las condiciones óptimas para la generación de poliol fueron: 80 °C, 3 % p/p catalizador (H2SO4), relación molar dobles enlaces:ácido acético 1:2 y tiempo de reacción de 8 h, obteniendo un porcentaje máximo del 78% de índice de acidez, y número de hidroxilo de 74 mg KOH/g. Limitaciones en el estudio / implicaciones: La eliminación del medio ácido y el agua en la reacción fue un desafío en polioles con mayor índice de acidez. Hallazgos/conclusiones: El método utilizado de extracción de grasa, permite obtener materia prima que cumple con las características para realizar la reacción de epoxidación e hidrólisis en un solo paso para obtener poliol. Las condiciones más severas de temperatura, concentración de catalizador, relación molar de dobles enlaces: ácido acético y tiempo de reacción, permitieron obtener la mayor cantidad de poliol de grasa avícola.Hidrólisis, grasa animal, epoxidación, residuos agroindustriales.
... [1][2][3] The oil obtained from Jatropha without any processing or even blending operations is directly entered into diesel engines as a suitable replacement. 4 Besides the fuel oil (biodiesel) that is obtained from the jatropha plant, its residues can be used to produce natural pesticides and vegetable fertilizers. 5 Using biodiesel fuel up to 85% reduces air pollution and CO 2 and the effects of climate change, this plant improves soil conditions and grows well due to its resistance to adverse conditions. ...
In this study, the mechanism of biodiesel production from jatropha oil and methanol is investigated in the presence of nano-graphene oxide (NGO) with carboxy, hydroxy, and epoxy functional groups. This heterogeneous nano-catalyst can be included in the group of heterogeneous basic and acidic catalysts in biodiesel production. At first, optimized and simulated all geometric structures of jatropha oil (C57H104O6), methanol, biodiesel, and glycerin. Due to its double bond in Jatropha oil, it has two configurations of cis and trans. The obtained results show that the trans configuration is more stable when in proximity to the nano-catalyst. The structural and thermodynamic parameters were obtained and evaluated for the approach and interaction of jatropha oil with methanol on carboxy, hydroxy, and epoxy functional groups and converted to biodiesel by the DFT calculation method. Graphene oxide nano-catalysts have separation potential, reuse and removing neutralization and washing steps, reducing the amount of waste produced and most importantly reduction of cost. Among the functional groups on the edge of NGO, the hydroxy group has performed better than the carboxy functional group in terms of reaction speed and biodiesel production. Although the carboxy functional group is resistant to free fatty acids (FFAs) and water and can perform both transesterification and esterification reactions at the same time, their reaction time is much longer than the hydroxy functional group. At the same time, during electron exchange, the absorption energy of biodiesel production on the hydroxy functional group (k = 2.04 × 10¹¹ h⁻¹) is less than other functional groups of NGO.
... Oligomers from jatropha oil, due to their long aliphatic chains providing the required flexibility, have also been reported wherein jatropha oil was epoxidized and then acrylated using acrylic acid. 85,86 Isosorbide obtained from starch has also been tested for its use as a potential material for use in making acrylate-based FR systems. In one 87 The phosphorus moiety acts as a char-forming catalyst, increased aromaticity also added to improved thermal stability and char formation Polystyrene + exo-5-(diphenylphosphato)isosorbide-5endo-acrylate pHRR-approx. ...
... For example, Jatropha-based oligomers have shown good adhesive properties due to the epoxy groups that form hydroxyl groups on opening, which get replaced by acrylic acid, thereby giving good adhesion with low viscosity. 85,86 Level of oxygenation of phosphorous in acrylates has been found to affect the mode of action of phosphorous compounds. The compounds with a higher degree of oxygen are active in the solid-state mechanism, while those with a lower degree are engaged in the gas phase. ...
The current review explicitly describes the phosphorus-based flame-retardant (FR) coating materials derived from the bio-resources. It segregates the coatings according to their polymeric backbone type and correlates their structure with the end-application properties. The review will provide a readership to understand different chemistries of FR systems and implement similar in developing the bio-based FR systems for coatings. Furthermore, the review targets to brief the various mechanisms of phosphorus-based FR coating systems depending upon the resin type, such as epoxy, phenolic, polyurethane. The synergistic effects of phosphorus and other FR moieties are also discussed, along with their synthesis chemistries and the structural impact on the properties.
... This is what causes the need for other alternative raw materials that can replace commercial oils, that is non-commercial vegetable oils. Some non-commercial vegetable oils that have been used as raw material for epoxy synthesis are still very limited, including the epoxy from jatropha oil (Wong et al., 2017;Derahman et al., 2019;Mai et al., 2021) and kapok seed oil (Tayde and Thorat, 2015). Non-commercial vegetable oils such as ketapang seed oil (hereinafter written as ketapang oil) can be an alternative as raw material for epoxy synthesis because of their abundant availability and not being used optimally. ...
Unsaturated fatty acids contained in vegetable oils can be used as a raw material to produce epoxy through epoxidation reactions. This study aims to obtain the optimum conditions for the epoxidation reaction of Terminalia catappa L. (local name “ketapang”) seed oil. In this study, the epoxidation reaction was carried out by reacting the ketapang seed oil and a mixture of formic acid and hydrogen peroxide, and sulfuric acid as a catalyst. The optimum reaction conditions obtained were reaction temperature of 45°C, reaction time of 5 hours, and reactants molar ratio of 1:4:5 (mol/mol). The percentage of the oxirane oxygen content of the products synthesized using the optimum reaction conditions was 3.46% with the percentage relative conversion to oxirane of 78%.
... corresponds to the proton peak of acrylate (OOC−CH�CH 2 ), confirming the successful grafting of AA on ESO. 33 Figure 4e shows the TG curves of acrylate and ESO. It can be seen that the initial decomposition of ESO is at ∼300°C, while that of acrylate is at ∼200°C. ...
It is well known that UV radiation can cause human health problems and that energy consumption can lead to human survival problems. Here, we prepared a composite membrane that can block UV radiation as well as reduce energy consumption. Carbon dots (CDs) and acrylates were prepared from xylose and epoxidized soybean oil as biomass feedstocks, respectively, and the composite membrane was prepared by a self-assembly strategy. The first layer of the membrane is composed of CDs and epoxy resin. Its main function is not only to weaken UV rays and the aggregation-induced quenching effect of CDs but also to reduce the absorption of UV rays by the second layer of the membrane. The second layer consists of barium sulfate (BaSO4) and acrylate. Compared to TiO2 (3.2 eV), BaSO4 (∼6 eV) has a higher electronic band gap, which reduces the absorption of UV light by the membrane. The composite membrane exhibits excellent UV-blocking and radiative cooling performance, shielding 99% of UV rays. In addition, the membrane can reduce 4.4 °C in radiative cooling tests, achieving a good cooling effect. Finally, the recyclability of the BaSO4/acrylate membrane is discussed, and 95% recovery rate provides sustainable utilization of the membrane. The composite membrane is expected to be popularized and used in low latitudes and areas with high temperature and high UV radiation near the equator.
... Acrylation of Epoxidized Jatropha Seed Oil. Jatropha seed oil is another nonedible oil that is renewable and sustainable to produce vegetable oil-based epoxy and epoxy acrylate as a raw polymeric material [55]. Due to the presence of toxic compounds named phorbol ester, Jatropha seed oil could not be used for cooking [17]. ...
... EJO has an OOC of 5%, which is reduced to around 0.17% after the oxirane ring-opening process. The decrease of AV from 27 mg KOH/g to 4.42 mg KOH/g shows that the acrylic acid is being consumed [17,55]. For the FTIR spectrum in Figure 9, the hydroxyl group (-OH) was identified at 3473 cm -1 due to the ring-opening reaction of epoxide by catalyst reaction. ...
... The synthesis of acrylated epoxidized Jatropha seed oil (AEJO) was confirmed by the acrylate double bond (CH=CH 2 ) at 1636 cm -1 and 1618 cm -1 . Last but not the least, a small peak of the epoxide group at 830 cm -1 indicated that not all epoxy groups have been consumed during the acrylation process [55]. ...
Chemically modified vegetable oils have become commercially attractive nowadays because they can be utilized as specialized components for the production of bioplasticizers and biopolymers due to their characteristics as being inexpensive, nontoxic, biodegradable, and renewable products. Due to the presence of unsaturation sites in the vegetable oils, they can be chemically modified and transformed into polymeric monomers such as acrylated epoxidized vegetable oils through well-known processes like epoxidation and acrylation processes. Acrylated epoxidized vegetable oil is a biopolymer that has a multitude of applications and is used mainly as a coating material for plastic, paper, and wood. There is an enormous demand for this biopolymer, and the market growth prospects are huge in some regions of the world. However, there are some challenges in the synthesis of acrylated epoxidized vegetable oils in achieving the performance of similar acrylated polymer derived from petroleum sources. In this paper, the chemical structure, properties, and chemical modifications of different types of vegetable oils were reviewed where the emphasis was given on epoxidation and its subsequent acrylation processes. This paper also highlights four types of epoxidation and their subsequent acrylation processes involving five different vegetable oils.
... The Fourier Transform Infra-Red (FTIR) analysis method was adopted from the previous study [22,23]. This analysis aims to determine the functional group in the Jatropha oil, FAME, and epoxides. ...
... However, at higher concentrations and longer time, epoxidation yield was similar. Therefore, due to the high possibility of an explosion at higher concentrations of hydrogen peroxide, it is not recommended [23]. In addition, a paper reported by previous researchers [32] stated that the shortcomings of using high concentrations of hydrogen peroxide also included the problem in agitation and decreased the mass transfer rate, which resulted in low epoxidation yield. ...
The aim of this study was to apply the experimental design methodology in the optimization of the epoxidation of fatty acid methyl esters (FAME) derived from Jatropha oil. This experiment was carried out with peracetic acid generated in situ by using hydrogen peroxide and acetic acid. The reaction surface (RSM) methodology based on the central composite design (CCD) approach is applied, which involves the percentage (%) of the epoxidation yield as the reaction variables. The reactions were described as the function of parameters such as temperature (50-80 °C), mol ratio of hydrogen peroxide (HP) to unsaturation (1.1-2 mol), mol ratio of acetic acid (AA) to unsaturation (0.5-0.8 mol) and time (2-7 hours). The optimum percentage of epoxidation yield (90.98 %) was at the condition of 65 °C reaction temperature, HP to unsaturation mol ratio of 2.19, AA to unsaturation mol ratio of 0.65 for 6 hours. The formation of epoxides product (oxirane) was confirmed using Fourier transform infrared spectroscopy oxirane peaks (doublet) at 825 and 843 cm-1. The result showed good agreement with the predicted values from the RSM model.
... Meanwhile, the peak of 2.75 ppm was attributed to the methylene protons between the two carbon double bonds (=CH-CH2-CH=), which proved the existence of linoleic fatty acid in the triglyceride of JO molecules. This result was comparable with other studies on pure JO [43,44]. ...
Jatropha oil-based polyol (JOL) was prepared from crude Jatropha oil via an epoxidation and hydroxylation reaction. During the isocyanation step, two different types of diisocyanates; 2,4-toluene diisocyanate (2,4-TDI) and isophorone diisocyanate (IPDI), were introduced to produce Jatropha oil-based polyurethane acrylates (JPUA). The products were named JPUA-TDI and JPUA-IPDI, respectively. The success of the stepwise reactions of the resins was confirmed using 1H nuclear magnetic resonance (NMR) spectroscopy to support the Fourier-transform infrared (FTIR) spectroscopy analysis that was reported in the previous study. For JPUA-TDI, the presence of a signal at 7.94 ppm evidenced the possible side reactions between urethane linkages with secondary amine that resulted in an aryl-urea group (Ar-NH-COO-). Meanwhile, the peak of 2.89 ppm was assigned to the α-position of methylene to the carbamate (-CH2NHCOO) group in the JPUA-IPDI. From the rheological study, JO and JPUA-IPDI in pure form were classified as Newtonian fluids, while JPUA-TDI showed non-Newtonian behaviour with pseudoplastic or shear thinning behaviour at room temperature. At elevated temperatures, the JO, JPUA-IPDI mixture and JPUA-TDI mixture exhibited reductions in viscosity and shear stress as the shear rate increased. The JO and JPUA-IPDI mixture maintained Newtonian fluid behaviour at all temperature ranges. Meanwhile, the JPUA-TDI mixture showed shear thickening at 25 °C and shear thinning at 40 °C, 60 °C and 80 °C. The master curve graph based on the shear rate for the JO, JPUA-TDI mixture and JPUA-IPDI mixture at 25 °C, 40 °C, 60 °C and 80 °C was developed as a fluid behaviour reference for future storage and processing conditions during the encapsulation process. The encapsulation process can be conducted to fabricate a self-healing coating based on a microcapsule triggered either by air or ultra-violet (UV) radiation.
... These signals showed no changes before and after the epoxidation reaction took place. A similar 1 H NMR spectrum of epoxidized jatropha oil was also reported previously [29,30]. ...
In this paper, we report the preparation of bio-based polyurethane (PU) from renewable vegetable oil. The PU was synthesized through the reaction between jatropha oil-based polyol and isocyanate in a one-shot method. Then, lithium perchlorate (LiClO4) salt was added to the polyurethane system to form an electrolyte film via a solution casting technique. The solid polymer electrolyte was characterized through several techniques such as nuclear magnetic resonance (NMR), Fourier transforms infrared (FTIR), electrochemical studies, thermal studies by differential scanning calorimetry (DSC), and dynamic mechanical analysis (DMA). The NMR analysis confirmed that the polyurethane was successfully synthesized and the intermolecular reaction had occurred in the electrolytes system. The FTIR results show the shifting of the carbonyl group (C=O), ether and ester group (C–O–C), and amine functional groups (N–H) in PU–LiClO4 electrolytes compared to the blank polyurethane, which suggests that interaction occurred between the oxygen and nitrogen atom and the Li+ ion as they acted as electron donors in the electrolytes system. DSC analysis shows a decreasing trend in glass transition temperature, Tg and melting point, Tm of the polymer electrolyte as the salt content increases. Further, DMA analysis shows similar behavior in terms of Tg. The ionic conductivity increased with increasing salt content until the optimum value. The dielectric analysis reveals that the highest conducting electrolyte has the lowest relaxation time. The electrochemical behavior of the PU electrolytes is in line with the Tg result from the thermal analysis.
