D-Glucose-fatty Acid Ester Synthesis with or without a Biocatalyst in the Same Organic Media

Çetinkaya, Sevil; Yenidünya, Ali Fazıl; Başoğlu, Faika; Saraç, Kamuran

doi:10.5650/jos.ess20072

Cited by 3 publications

(4 citation statements)

References 10 publications

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“…Evaporation of ethyl acetate was carried out leaving the oily product that was further dried at room temperature producing the solidified glucose esters that having pale brown colors. The three glucose‐fatty acid esters plasticizers are glucose palmitate (GEP1), glucose oleate (GEP2) and (GEP3) which is glucose octanoate 31 . Preparation of these esters are represented in Scheme 2.…”

Section: Methodsmentioning

confidence: 99%

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Enhanced performance of eco‐friendly PVC by utilizing halo‐benzothiazole derivatives and glucose/fatty acids esters

Abdel‐Monem,

Gaballah,

Rabie

2023

Vinyl Additive Technology

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Two halo‐benzothiazoles, namely, 2‐amino‐6‐bromo‐benzo[d]thiazole and 2‐amino‐6‐fluoro‐benzo[d]thiazole were utilized to modify poly(vinyl chloride) (PVC) and gave two modified PVC samples for biomedical applications. Prepared glucose‐fatty acid esters of palmitic, oleic, and octanoic acids were exploited as plasticizers to produce phthalate‐free eco‐friendly antimicrobial PVC. The chemical structures of all prepared compounds were confirmed via Fourier‐transform infrared spectroscopy. The thermal properties of modified PVC was determined using thermo gravimetric analysis and differential scanning calorimetry while weight loss and degree of discoloration were used to assess the photostability after UV irradiation whereas references heat and UV absorbers were applied for comparison. The plasticizing effect of each glucose‐fatty acid ester at 20% by weight on the mechanical properties of modified PVC was determined and referenced to diethylhexylphthalate. The results revealed that the mechanical properties as well as the thermal stability of plasticized modified PVCs were enhanced. Plasticizers migration from the polymeric matrix was also determined and the results showed low extent of migration of the prepared plasticizers. So, modified plasticized PVC samples exhibited improved physicochemical properties. Antimicrobial properties of all samples, using disc diffusion agar method, were evaluated against some Gram +ve bacteria like Staphylococcus aureus and Streptococcus mutans and Gram −ve bacteria like Escherichia coli, Klebsiella pneumonia, and Pseudomonas aeruginosa and fungi strains used were Candida albicans, Aspergillus niger, and Aspergillus ochraceous. All investigated compounds showed improved antibacterial and antifungal activities.Highlights PVC was chemically modified with two halo‐benzothiazoles to obtain antimicrobial PVC. Glucose‐fatty acids esters were prepared as eco‐friendly plasticizers for PVC. Halo‐benzothiazoles improved both the thermal‐ and photo‐stability of PVC. Glucose‐fatty acid plasticizers enhanced the mechanical properties of PVC. The extent of migration of prepared plasticizers is lower than that of reference plasticizer.

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Section: Methodsmentioning

confidence: 99%

“…The three glucose-fatty acid esters plasticizers are glucose palmitate (GEP1), glucose oleate (GEP2) and (GEP3) which is glucose octanoate. 31 Preparation of these esters are represented in Scheme 2.…”

Section: Preparation Of Glucose-fatty Acid Estersmentioning

confidence: 99%

Enhanced performance of eco‐friendly PVC by utilizing halo‐benzothiazole derivatives and glucose/fatty acids esters

Abdel‐Monem,

Gaballah,

Rabie

2023

Vinyl Additive Technology

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“…NMR analysis shows the absence of selectivity, demonstrated by the presence, on 1 H NMR spectra, of weak signals between 4 ppm and 5.5 ppm, and of signals between 170 ppm and 173 ppm (C=O) on 13 C NMR spectra in both reaction routes whatever the acyl donor was, demonstrating variability in the ester formation site. In the literature, DMSO has been shown to catalyze the formation of sugar esters, with palmitic and oleic acids [48,49], but not during transesterification.…”

Section: Enzyme Selectivitymentioning

confidence: 99%

Optimization of Enzymatic Synthesis of D-Glucose-Based Surfactants Using Supported Aspergillus niger Lipase as Biocatalyst

Spalletta,

Joly,

Martin

2023

Chemistry

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Surfactants are amphiphilic molecules with the ability to modify the surface tension between two surfaces. They can be obtained by various methods, the main one being synthetic, from petroleum-based substrates. Their universal use in a wide range of fields has created a global market and, consequently, ecological, and economic expectations for their production. Biocatalyzed processes, involving enzymes, can address this objective with processes complying with the principles of green chemistry: energy saving, product selectivity, monodispersity, and reduction in the use of solvents, with energy eco-efficiency. For example, fatty-acid carbohydrate esters are biobased surfactants that can be synthesized by lipases. In this work, we were interested in the synthesis of D-glucose lauric ester, which presents interesting properties described in the literature, with Aspergillus niger lipase, rarely described with sugar substrates. We optimized the synthesis for different parameters and reaction media. This lipase appeared to be highly selective for 6-O-lauroyl-D-glucopyranose. However, the addition of DMSO (dimethyl sulfoxide) as a co-solvent displays a duality, increasing yields but leading to a loss of selectivity. In addition, DMSO generates more complex and energy-intensive purification and processing steps. Consequently, a bio-sourced alternative as co-solvent with 2MeTHF3one (2-methyltetrahydrofuran-3-one) is proposed to replace DMSO widely described in the literature.

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“…The enzymatic portion of global synthetic product cost is low [31]. Enzymes have become the most relevant biocatalysts for various applications [32], especially because they are able to catalyze both hydrolysis and esterification reactions. Over the last 30 years, there has been a steady increase in the number of publications related to the use of enzymes [33], and it is a field that is still booming [34].…”

Section: Introductionmentioning

confidence: 99%

Latest Trends in Lipase-Catalyzed Synthesis of Ester Carbohydrate Surfactants: From Key Parameters to Opportunities and Future Development

Spalletta,

Joly,

Martin

2024

IJMS

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Carbohydrate-based surfactants are amphiphilic compounds containing hydrophilic moieties linked to hydrophobic aglycones. More specifically, carbohydrate esters are biosourced and biocompatible surfactants derived from inexpensive renewable raw materials (sugars and fatty acids). Their unique properties allow them to be used in various areas, such as the cosmetic, food, and medicine industries. These multi-applications have created a worldwide market for biobased surfactants and consequently expectations for their production. Biobased surfactants can be obtained from various processes, such as chemical synthesis or microorganism culture and surfactant purification. In accordance with the need for more sustainable and greener processes, the synthesis of these molecules by enzymatic pathways is an opportunity. This work presents a state-of-the-art lipase action mode, with a focus on the active sites of these proteins, and then on four essential parameters for optimizing the reaction: type of lipase, reaction medium, temperature, and ratio of substrates. Finally, this review discusses the latest trends and recent developments, showing the unlimited potential for optimization of such enzymatic syntheses.

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D-Glucose-fatty Acid Ester Synthesis with or without a Biocatalyst in the Same Organic Media

Cited by 3 publications

References 10 publications

Enhanced performance of eco‐friendly PVC by utilizing halo‐benzothiazole derivatives and glucose/fatty acids esters

Enhanced performance of eco‐friendly PVC by utilizing halo‐benzothiazole derivatives and glucose/fatty acids esters

Optimization of Enzymatic Synthesis of D-Glucose-Based Surfactants Using Supported Aspergillus niger Lipase as Biocatalyst

Latest Trends in Lipase-Catalyzed Synthesis of Ester Carbohydrate Surfactants: From Key Parameters to Opportunities and Future Development

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