Biolubricant Production from Stearic Acid and Residual Secondary Alcohols: System and Reaction Design for Lipase-Catalyzed Batch and Continuous Processes

Lima, Rosemar de; Bento, Heitor B.S.; Reis, Cristiano E. Rodrigues; Bôas, Renata N. Vilas; Freitas, Larissa; Carvalho, Ana Karine Furtado de; Castro, Heizir F. de

doi:10.1007/s10562-021-03663-z

Cited by 11 publications

(5 citation statements)

References 32 publications

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“…The effect of molecular sieves (0%, 5%, 10%, and 20% m/v) concentration on the enzymatic production of cetyl stearate was subsequently examined. This water removal strategy has been widely used in the enzymatic production of industrial esters, including wax esters 12,14,23,49,50 . Based on these results displayed in Figure 3, there was a decrease in ester production from 70% to 48% using a molecular sieves concentration of 10% m/v, followed by a stabilization trend in the reaction (acid conversion percentage of 47% after 20 min of reaction at 20% m/v of molecular sieves).…”

Section: Resultsmentioning

confidence: 91%

“…This water removal strategy has been widely used in the enzymatic production of industrial esters, including wax esters. 12,14,23,49,50 Based on these results displayed in Figure 3, there was a decrease in ester production from 70% to 48% using a molecular sieves concentration of 10% m/v, followed by a stabilization trend in the reaction (acid conversion percentage of 47% after 20 min of reaction at 20% m/v of molecular sieves). Such a negative effect can be due to an increased viscosity by increasing the solid loading in the reaction medium, [51][52][53] which thus reduces the external diffusion of starting materials to the heterogeneous biocatalyst surface.…”

Section: Effect Of Molecular Sieve Concentration On Cetyl Stearate Pr...mentioning

confidence: 88%

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Enzymatic production of wax esters by esterification using lipase immobilized via physical adsorption on functionalized rice husk silica as biocatalyst

Machado

Sabi

Hirata

et al. 2023

Biotech and App Biochem

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The present study consists of developing an enzymatic process for the production of wax esters (lauryl stearate and cetyl stearate) by esterification in a heptane medium. Lipase from Thermomyces lanuginosus (TLL) immobilized via interfacial activation on silica particles from rice husks functionalized with triethoxy(octyl)silane (TLL–Octyl–SiO2) was used as biocatalyst. Maximum immobilized protein loading of around 22 mg g−1 (that corresponds to an immobilization yield of ≈55%) of support was observed using an initial protein loading of 40 mg g−1 of Octyl–SiO2. Its hydrolytic activity (olive oil emulsion hydrolysis) was of 620 U g−1 of biocatalyst. The effect of certain factors on the cetyl estearate production was evaluated using a central composite rotatable design (CCDR). Under optimal conditions (64°C, 21% of mass of biocatalyst per volume of reaction mixture, 170 rpm, and stoichiometric acid:alcohol molar ratio 1 mol L−1 of each reactant), maximum acid conversion percentage of 91% was observed after 60 min of reaction. Lauryl stearate was also produced under such conditions, and an acid conversion of 93% after 60 min of reaction was also achieved. Free lipase exhibited acid conversion of only 15%–20% for both reaction mixtures. After nine successive esterification batches, TLL–Octyl–SiO2 retained 85%–90% of its original activity. These results show the promising use of the prepared biocatalyst in wax esters production due to its high catalytic activity and reusability.

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Section: Resultsmentioning

confidence: 91%

Section: Effect Of Molecular Sieve Concentration On Cetyl Stearate Pr...mentioning

confidence: 88%

Enzymatic production of wax esters by esterification using lipase immobilized via physical adsorption on functionalized rice husk silica as biocatalyst

Machado

Sabi

Hirata

et al. 2023

Biotech and App Biochem

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“…67 By analyzing Table 3, it is observed that the reactions for biodiesel and biolubricants production can occur applying chemical catalysts, 19,61 but mainly enzymatic catalysts. 17,18,59,60,[62][63][64][65][66] It is noteworthy to point out that the reaction temperature is one of the factors that needs to be checked when determining the nature of the catalyst to apply, as the temperature used for enzymatic catalysts must be mild, 17,18,58,59,62 due to enzyme denaturation at high temperatures that would lead to reduced esters yields. 18 The reactions conducted with homogeneous chemical catalysts are usually carried out at higher temperatures and according to the boiling temperature of the solvent applied.…”

Section: Esters With Lubricating and Fuel Propertiesmentioning

confidence: 99%

Fusel Oil: Chemical Composition and an Overview of Its Potential Application

Massa¹,

Raspe²,

Feiten³

et al. 2023

J. Braz. Chem. Soc.

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Fusel oil (FO) is one of the by-products of the sugar-alcohol industry, which has application as an additional source of higher alcohols for production of esters with flavoring, fuels and lubricants properties, as well as additives in petroleum-based fuels and in pesticide formulations. Thus, this review is focused on the characteristics of FO and its applications as an acyl acceptor in transesterification and esterification reactions for esters production, its addition to fossil fuels, and the herbicidal and fungicidal potential of the compounds presented in its chemical composition. The operating conditions of the process, results obtained, and patented applications in the food, cosmetic, transportation and agricultural sectors are also reported and discussed. Furthermore, main trends, challenges and recommendations are proposed in order to overcome the disadvantages of applying FO in the reported sectors, as well as alternatives for the development of new lines of research are suggested.

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“…De Lima et al (2021) investigated the synthesis of esters with lubricating properties through the use of fusel oil (residual raw material from ethanol distillation) with stearic acid using lipases as catalysts. The results indicated high conversion (94% in 24 h of reaction) when using lipases from R. oryzae and C. antarcti ca immobilized on STY‐DVB (styrene and divinylbenzene).…”

Section: Enzymatic Synthesis Of Esters Using Carboxylic Acids Of Diff...mentioning

confidence: 99%

A review of synthesis of esters with aromatic, emulsifying, and lubricant properties by biotransformation using lipases

Bôas

Castro

2022

Biotech & Bioengineering

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The esterification reactions catalyzed by lipases are among the most significant biochemical processes of industrial relevance. The lipases have the function of versatility by catalyzing a diversity of reactions with extreme ease, obtaining quality products with high yield. Therefore, enzyme-catalyzed esterification has gained increasing attention in many applications, due to the importance of derived products.More specifically, lipase-catalyzed esterification reactions have attracted interest in research over the past decade, due to the increased use of organic esters in the chemical and biotechnology industry. These esters can be obtained by three techniques: extraction from natural sources, chemical and enzymatic syntheses. Biotechnological processes have offered several advantages and are shown as a competitive alternative to chemical methods due to high catalytic efficiency, mild operating conditions, and selectivity of natural catalysts. These an industrial point of view, reactions catalyzed by enzymes are the most economical approach to achieve green products with no toxicity and no harm to human health. Thus, this review presents a descriptive evaluation of the trends and perspectives applied to enzymatic esterification, mainly for the synthesis of esters with different properties, such as aromatics, emulsifiers, and lubricants using the esterification process. An emphasis is given to essential factors, which affect the lipase-catalyzed esterification reaction. In which, the parameters are dependent on the lipase source, a form of the biocatalyst (free or immobilized), the polarity of the reaction medium, the molar ratio between alcohol and acid, among other variables, are also discussed.

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Biolubricant Production from Stearic Acid and Residual Secondary Alcohols: System and Reaction Design for Lipase-Catalyzed Batch and Continuous Processes

Cited by 11 publications

References 32 publications

Enzymatic production of wax esters by esterification using lipase immobilized via physical adsorption on functionalized rice husk silica as biocatalyst

Enzymatic production of wax esters by esterification using lipase immobilized via physical adsorption on functionalized rice husk silica as biocatalyst

Fusel Oil: Chemical Composition and an Overview of Its Potential Application

A review of synthesis of esters with aromatic, emulsifying, and lubricant properties by biotransformation using lipases

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