Lipase catalyzed solvent free synthesis of monoacylglycerols in various reaction systems and coupling reaction with pervaporation for in situ water removal

Satyawali, Yamini; Cauwenberghs, Lieve; Maesen, Miranda; Dejonghe, Winnie

doi:10.1016/j.cep.2021.108475

Cited by 15 publications

(4 citation statements)

References 53 publications

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“…This is due to the fact that a higher glycerol concentration can result in higher viscosity of the reaction mixture and significant mass transfer resistance [ 17 ]. In the longer-term, excess glycerol inhibits the enzyme activity due to its polar nature as it can strip the water out from the immobilized enzyme which eventually could lead to its inactivation [ 19 ]. The higher molar fraction of TAG compared to glycerol enhanced the synthesis of dilaurin.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Glycerolysis of Palm Kernel Olein-Stearin Blend for Monolaurin Synthesis as an Emulsifier and Antibacterial

Ngatirah

Hidayat

Rahayu

et al. 2022

Foods

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Monolaurin is a monoacylglycerol, which can act as an emulsifier and antibacterial. Palm kernel oil is a monolaurin raw material that can be fractionated into palm kernel olein (PKOo) and palm kernel stearin (PKS). Therefore, this study prepares monolaurin through enzymatic glycerolysis of the PKOo-PKS blend. The effects of enzyme concentration, molar ratio of oil to glycerol, solvent to oil ratio, and reaction temperature on the products of glycerolysis were investigated. The best conditions were selected for further production, purification, and characterization of the monolaurin. The results showed that the best glycerolysis condition was obtained with an enzyme concentration of 10% w/w, an oil–glycerol molar ratio of 1:4, a solvent–oil ratio of 2:1 v/w, and a glycerolysis temperature of 40 °C with a stirring speed of 600 rpm based on the monoacylglycerol (MAG) concentration. The identification of the sample with FTIR and NMR indicated that the purified glycerolysis product is the monolaurin. The thermal analysis showed a large endothermic peak with a melting point of 35.56 °C. The purified monolaurin has a HLB value of 5.92, and an emulsion capacity and stability of 93.66 ± 1.85% and 89.54 ± 3.36%, respectively. The minimum inhibitory concentration (MIC) of the monolaurin for Escherichia coli FNCC 0091 and Staphylococcus aureus FNCC 0047 were at 500 ppm, and 100 ppm for Bacillus subtilis FNCC 0060.

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Section: Resultsmentioning

confidence: 99%

Enzymatic Glycerolysis of Palm Kernel Olein-Stearin Blend for Monolaurin Synthesis as an Emulsifier and Antibacterial

Ngatirah

Hidayat

Rahayu

et al. 2022

Foods

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“…Correspondingly, FAEE levels in nonpolar systems were lower, indicating that the alcoholysis of glycerides progressed slowly in these two systems. Theoretically, the miscibility of oil with a low-polar solvent is better than with a polar solvent; the contact areas between enzyme and substrate and between substrate and substrate are larger [ 43 ], which usually leads to improved catalytic efficiency of the enzyme. Surprisingly, increasing the miscibility of the oil with ethanol in a non-polar system led to a decreased 2-MAG yield in lipase-catalyzed alcoholysis.…”

Section: Resultsmentioning

confidence: 99%

Preparation of 2-Arachidonoylglycerol by Enzymatic Alcoholysis: Effects of Solvent and Water Activity on Acyl Migration

Wang

Liu

Wang

et al. 2022

Foods

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Enzymatic alcoholysis was performed in an organic medium to synthesize 2-monoacylglycerol (2-MAG) rich in arachidonic acid. The results showed that solvent type and water activity (aw) significantly affected the 2-MAG yield. Under the optimum conditions, 33.58% 2-MAG was produced in the crude product in t-butanol system. Highly pure 2-MAG was obtained after two-stage extraction using 85% ethanol aqueous solution and hexane at first stage and dichloromethane and water at second stage. Isolated 2-MAG was used as substrate to investigate the effect of solvent type and aw on 2-MAG acyl migration in a lipase-inactivated system. The results indicated that non-polar solvents accelerated the acyl migration of 2-MAG, whereas isomerization was inhibited in polar solvent systems. The aw exhibited the strongest inhibition effect on 2-MAG isomerization at 0.97, but also affected the hydrolysis of glycerides and lipase selectivity.

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“…Table 5 shows the selectivity differences for the type of technology used for monoglycerides formation. When glycerin esters are synthesized, high percentages of monoglycerides and diglycerides are usually appreciated, especially monoglycerides owing to their high antimicrobial effect (Satyawali et al, 2021). As can be seen in Fig.…”

Section: Effect Of Reaction Route Selectivity On Monoglycerides Forma...mentioning

confidence: 99%

Cleaner and Sustainable Synthesis of High Quality Monoglycerides by use of Enzyme Technologies: Techno-economic and Environmental study for Monolaurin

Mustafa

Fathy

Kutlu

et al. 2022

Preprint

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Currently, monoglycerides (MG) are produced using a complicated energy intensive technology that contributes negatively toward greenhouse gas mitigation. This work suggests a cleaner and simpler one-step enzymatic production of α-monolaurin in an inert membrane reactor, where the reaction and enzyme separation are conducted simultaneously in one unit. Candida antarctica lipase (Lipozyme 435) was used to catalyze the esterification reaction between lauric acid and glycerin in a solvent-free system under mild temperatures. Response surface methodology was used to optimize the reaction conditions. The optimal conditions were a molecular sieve of 14.85% w/w, a temperature of 56.95°C, an enzyme amount of 5.38% w/w, and a molar ratio of 4.75% w/w. The gas chromatography (GC) analysis showed that the α-monolaurin percentage was 49.5% when the enzymatic process (ENZ) was used. The conventional chemical (CHEM) and autocatalytic (AUT) esterification methods were also performed to study their proportional MG yields. The GC results showed the MG percentages of 43.9% and 41.7% for CHEM and AUT, respectively. Economic analysis was also conducted for the suggested enzymatic technique, and the findings were compared with those of the CHEM and AUT technologies. Using a plant capacity of 4950 t/year and 11% interest for the proposed ENZ process, the total capital investment of α-monolaurin production was preferably four times less than that of the CHEM process and three times less than that of the AUT method, presenting investment possibilities. However, the ENZ process showed the least profitability (net profit per day) among the three processes. Nevertheless, the return on investment and net present value for the ENZ process were preferably higher than those of CHEM and AUT because of its interestingly lower inside battery limit plant cost and less energy consumption. The AUT/CHEM processes generated a total carbon dioxide (CO2) exhaust of t CO2 678.7 eq./year. In contrast, the ENZ process exhausted a total CO2 of only 50 t CO2 eq./year. The present integrated techno-economic and environmental study of α-monolaurin production emphasizes the green and cost benefits of the proposed ENZ technology.

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Lipase catalyzed solvent free synthesis of monoacylglycerols in various reaction systems and coupling reaction with pervaporation for in situ water removal

Cited by 15 publications

References 53 publications

Enzymatic Glycerolysis of Palm Kernel Olein-Stearin Blend for Monolaurin Synthesis as an Emulsifier and Antibacterial

Enzymatic Glycerolysis of Palm Kernel Olein-Stearin Blend for Monolaurin Synthesis as an Emulsifier and Antibacterial

Preparation of 2-Arachidonoylglycerol by Enzymatic Alcoholysis: Effects of Solvent and Water Activity on Acyl Migration

Cleaner and Sustainable Synthesis of High Quality Monoglycerides by use of Enzyme Technologies: Techno-economic and Environmental study for Monolaurin

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