Optimization and theoretical analysis of lipase-catalyzed enzymatic esterification of glycerol for efficient glycerides synthesis

Sousa, Paulo Gleisson Rodrigues de; Camara, Ana Gabrielle do Nascimento; Oliveira, Artur Ramon Tomé; Lima, Gabriella de Castro; Lima, Gledson Vieira; Coutinho, Lucas Pinheiro; Alexandre, Jeferson Yves Nunes Holanda; Serafim, Leonardo F.; Mattos, Marcos Carlos de; Monteiro, Norberto de Kássio Vieira; Santos, José Cleiton Sousa dos

doi:10.1016/j.bej.2023.109033

Cited by 5 publications

(3 citation statements)

References 71 publications

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“…Glycerine acetate, which plays the role of an antifreeze agent [10], can be chemically converted from bioglycerol to reach both goals of increasing glycerol's economic value and reducing the biodiesel's CFPP. Bioglycerol can be esterified with acetic acid to form monoacylglycerols (MAG), diacylglycerols (DAG), and triacylglycerols (TAG) [11]. MAG can be used as a food additive, while DAG and TAG have been applied as gasoline antiknocking additives and additives for reducing fuel viscosity and cold filter plugging points.…”

Section: Introductionmentioning

confidence: 99%

Effects of Heterogeneous Sulfated Acid Photocatalysts and Irradiation of Ultraviolet Light on the Chemical Conversion and Characteristics of Antifreeze from Bioglycerol

Lin,

Chen

2024

Processes

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The purity of crude glycerol, a by-product of biodiesel production, may be as low as 50%. Thus, it has relatively low economic value without previously applying adequate physical purification or chemical conversion processes. A solid-state sulfated acid photocatalyst, TiO2/SO42- was prepared in this study to catalyze the chemical conversion of bioglycerol with acetic acid to produce an antifreeze of glycerine acetate to improve the low-temperature fluidity of liquid fuel. The experimental results show that similar X-ray intensity structures appeared between the catalysts of TiO2/SO42- and SO42-. An infrared spectra analysis using a Fourier transform infrared (FTIR) spectrometer confirmed the successful sintering of SO42- and ligating with TiO2 for preparing TiO2/SO42-. The effects of the photocatalyst were further excited by the irradiation of ultraviolet light. The highest weight percentage of glycerine acetate was obtained under a reaction time and reaction temperature of 10 hours and 120°C, respectively. In addition, it was observed that the glycerol conversion ratio reached 98.65% and the triacylglycerols compound amounted to 40.41 wt.% when the reacting molar ratio was 8. Moreover, the freezing point of the product mixture of glycerine acetate under the same molar ratio reached as low as -46.36°C; the lowest among the products made using various molar ratios of acetic acid/glycerol. The UV light irradiation rendered higher triacylglycerols and diacylglycerols with lower diacylglycerol formation ratios than those without light irradiation.

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Section: Introductionmentioning

confidence: 99%

Effects of Heterogeneous Sulfated Acid Photocatalysts and Irradiation of Ultraviolet Light on the Chemical Conversion and Characteristics of Antifreeze from Bioglycerol

Lin,

Chen

2024

Processes

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“…It has a low production cost (15 US$/kg) and contains 269 amino acid residues, a molecular mass of ∼30 kDa, and an activity of 9100 IU/mL . This enzyme has been used as a catalyst in many chemical reactions, such as the enzymatic esterification of glycerol, the synthesis of biolubricants, the production of biodiesel from the esterification of babassu oil (Orbignya sp. ), and the production of esters using tucuman oil (Astrocaryum vulgaris) …”

Section: Introductionmentioning

confidence: 99%

Green Enzymatic Synthesis of Geranyl Butyrate: Process Optimization and Mechanistic Insights

Simão Neto,

Sousa Junior,

da Silva Filho

et al. 2024

ACS Omega

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Flavor esters are organic compounds widely used in the food industry to enhance the aroma and taste of products. However, most chemical processes for the production of these flavoring compounds use toxic organic solvents. Some organic solvents derived from petroleum can leave behind residual traces in food products, which may raise concerns about potential health risks and contamination. In this study, we employ Eversa Transform 2.0, a commercial lipase derived from the lipase from Thermomyces lanuginosus, to produce geranyl butyrate in aqueous media. The chemical process was optimized using the Taguchi method, and a conversion of 93% was obtained at the optimal reaction conditions of: 1:5 molar ratio (v/v), 15% biocatalyst load (w/w), at 50 °C, in 6 h. Classic (molecular dynamics) and quantum (density functional theory) simulations unveiled amino acid residues involved in the stabilization of the enzyme−substrate complex. Detailed QM/MM mechanistic studies identified the nucleophilic attack of the deacylation reaction as the rate-limiting step of the entire mechanism, which has a free energy barrier of 14.0 kcal/mol.

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“…In light of these challenges, there s a burgeoning interest in the potential of biocatalysis through enzymes. Such enzy-matic methods operate under milder conditions, offer improved substrate specificity, enhance catalytic efficiency, and produce fewer byproducts 18,19) . As a result, the enzymatic strategy is being recognized as a more sustainable and health-centric alternative, capturing significant industrial interest 20−22) .…”

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confidence: 99%

Efficient Enzymatic Enrichment of High-purity Nervonic Acid from <i>Malania oleifera</i> Seed Oil

Yang,

Lin,

Chen

et al. 2024

J. Oleo Sci.

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IntroductionNervonic acid (NA; C24:1Δ15; cis-15-tetracosenoic acid) is an ultra-long-chain monounsaturated fatty acid that is widely present in the brain and other neural tissues 1) . This pivotal acid not only contributes to the normal functioning of neural tissues in organisms, but also promotes neurocellular synthesis and brain development in infants 2,3) . Decreased levels of NA are closely associated with several neurological diseases, such as demyelinating disorders, Alzheimer s disease, adrenoleukodystrophy, and depression 4−7) . Consequently, studies have demonstrated NA s potential in in the treatment and prevention of neurodegenerative diseases. However, it is difficult for the body to synthesize NA. Emerging research underscores the benefits of dietary NA supplementation, leading to its incorporation as an active constituent in health foods 8) . Beyond its medical relevance, the versatile NA has found its niche in cosmetic formulations due to its skin-related effects 9) . Given its multifaceted potential across pharmaceutical, nutraceutical, and industrial domains, the demand for high-purity NA is surging, emphasizing the need for consistent and high-quality production.NA was initially isolated from shark brain tissue and also

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Optimization and theoretical analysis of lipase-catalyzed enzymatic esterification of glycerol for efficient glycerides synthesis

Cited by 5 publications

References 71 publications

Effects of Heterogeneous Sulfated Acid Photocatalysts and Irradiation of Ultraviolet Light on the Chemical Conversion and Characteristics of Antifreeze from Bioglycerol

Effects of Heterogeneous Sulfated Acid Photocatalysts and Irradiation of Ultraviolet Light on the Chemical Conversion and Characteristics of Antifreeze from Bioglycerol

Green Enzymatic Synthesis of Geranyl Butyrate: Process Optimization and Mechanistic Insights

Efficient Enzymatic Enrichment of High-purity Nervonic Acid from <i>Malania oleifera</i> Seed Oil

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