Continuous preparation of flavour‐active acetate esters by direct biocatalytic esterification

Perdomo, Igor Chiarelli; Contente, Martina Letizia; Pinto, Andrea; Romano, Diego; Fernandes, Pedro; Molinari, Francesco

doi:10.1002/ffj.3552

Cited by 6 publications

(12 citation statements)

References 37 publications

(39 reference statements)

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“…Li et al state their suggested method shows great feasibility as a novel industry strategy (Figure 3) for the production of high purity DAGs and also promote the recommercialization of DAGs in the near future. 61 The continuous preparation of flavor-active ester was carried out using mycelium-bound lipase from Aspergillus oryza by Chiarelli Perdomo et al 12 The reaction is carried out in a continuous stirred tank membrane reactor, where the membrane allows for continuous removal of product while retaining the biocatalyst in the reaction pot, as shown in Figure 4. At an operating temperature of 60 °C and a residence time of 8 h, high conversion of ester is achieved which is 82%.…”

Section: Type Of Reactors Used and Choice Of Enzymes In Biocatalysismentioning

confidence: 99%

“…Temperature of 60 °C is found to be the most common and optimal temperature for the majority of biocatalysis, namely, transesterification, esterification, hydrolysis, interesterification, and glycerolysis reactions. − …”

Section: Overview Of Reaction Conditionsmentioning

confidence: 99%

“…Due to the hydrophobic properties of the dry mycelium, the esterification reaction does not require an additional water removal step. In the reusability of the enzyme, the enzyme’s operational stability could last up to 15 cycles …”

Section: Type Of Reactors Used and Choice Of Enzymes In Biocatalysismentioning

confidence: 99%

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Enzyme Biocatalysis for Sustainability Applications in Reactors: A Systematic Review

Chook,

Aroua,

Gew

2023

Ind. Eng. Chem. Res.

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Enzyme biocatalysis is well known for its biodegradability and environmentally friendly conditions. Its novel properties such as high reaction selectivity and mild reaction conditions prove that it is a promising alternative that can overcome the global resource scarcity of the conventional chemical catalysts that are of a nonrenewable source. In this study, we documented the advancements and breakthroughs in emerging biocatalysis reactor technologies spanning over a decade. We aim to encapsulate the remarkable progress and innovations witnessed within this dynamic field. Thus, we reviewed 48 articles related to enzyme biocatalysis in the production of glycerides using reactors. The reaction parameters using a biocatalysis route were reviewed systematically and discussed in our study. In the biocatalysis transformation, the processes mainly focus on the conversion of raw material into product. In the optimization of biocatalysis, temperature and residence time parameters have been thoroughly researched in order to maximize the productivity of the enzyme activity. In the selection of reactors, the type of reactor and its agitator play a vital role in enzyme activity. We anticipate that the greenness of biocatalysis transformation could be improved if the enzymes in waste streams could be converted from another reaction to functional products. This work may serve as a stepping stone for the biocatalysis industry, acting as a precursor for industries or individuals interested in exploring this evergreen field.

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Section: Type Of Reactors Used and Choice Of Enzymes In Biocatalysismentioning

confidence: 99%

Section: Overview Of Reaction Conditionsmentioning

confidence: 99%

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Enzyme Biocatalysis for Sustainability Applications in Reactors: A Systematic Review

Chook,

Aroua,

Gew

2023

Ind. Eng. Chem. Res.

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“…Esters of terpene alcohols, especially acetate esters, are valuable compounds in the flavor and fragrance industry, which was valued at 24.9 billion USD in 2014, with a predicted growth rate from 5 to 6% per year [1][2][3]. These compounds can be obtained via extraction from plant sources, chemical synthesis, or enzymatic biotransformation.…”

Section: Introductionmentioning

confidence: 99%

Biomass of a Psychrophilic Fungus as a Biocatalyst for Efficient Direct Esterification of Citronellol

et al. 2021

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A biomass-bound lipase from psychrophilic Chrysosporium pannorum A-1 is an efficient biocatalyst for direct esterification of β-citronellol and acetic acid in an organic solvent. The biomass is effectively produced by fungal submerged culture at 20 ℃, which results in lower energy consumption during the production of biocatalyst. Supplementation of the culture medium with calcium carbonate together with olive oil contributed to a significant increase in the active biomass of mycelium in one batch culture and increased the efficiency of the biocatalyst. Biomass-bound lipase showed high catalytic activity in a broad temperature range of 30–60 °C and stability up to 70 °C. A maximum molar conversion value of 98% was obtained at 30 °C in n-hexane using a 2:1 alcohol-to-acid molar ratio and 3% w/v of the biocatalyst within 24 h. The high equimolar concentration of the substrates (200 mM) did not have an adverse effect on mycelial biomass activity. Dry mycelium of C. pannorum is a promising biocatalyst for large-scale biosynthesis of citronellyl acetate, given its low-cost production, high activity at low temperatures, and reusability in a minimum of seven 24-h biocatalytic cycles.

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“…(a) Considering the activated substrates, allylic primary alcohols 3, 5, 7, 9, 13, and 15 (entries 2-5, 7, 8) were almost quantitatively esterified (GC-FID ratios of alcohol to acetate ranging from 10:90 to 4:96) to fragrant acetates, namely geranyl acetate 4 [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34], prenyl acetate 6, (E)-2-hexenyl acetate 8, cinnamyl acetate 10 [35][36][37][38][39][40][41], phytyl acetate (E/Z = 66:34) 14 [42], and (1R)-nopyl acetate 16, respectively. On the other hand, rac-linalool 11 remained almost intact with negligible acetylation only (entry 6).…”

Section: Introductionmentioning

confidence: 99%

Scalable Green Approach Toward Fragrant Acetates

Puchľová

Szolcsányi

2020

Molecules

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The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70% yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68% yield from the equimolar mixture of 1-pentanol and 3-pentanol.

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Continuous preparation of flavour‐active acetate esters by direct biocatalytic esterification

Cited by 6 publications

References 37 publications

Enzyme Biocatalysis for Sustainability Applications in Reactors: A Systematic Review

Enzyme Biocatalysis for Sustainability Applications in Reactors: A Systematic Review

Biomass of a Psychrophilic Fungus as a Biocatalyst for Efficient Direct Esterification of Citronellol

Scalable Green Approach Toward Fragrant Acetates

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