On the need for gate-to-gate environmental metrics in biocatalysis: fatty acid hydration catalyzed by oleate hydratases as a case study

Marı́a, Pablo Domı́nguez de

doi:10.1039/d2gc03419k

Cited by 20 publications

(25 citation statements)

References 42 publications

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“…For the strategy here presented, as a purification step is not required, wastes and wastewater are not produced, so the TCR parameter should be equal to zero. However, by considering the PMI value of the organic compounds (Table , entry 4), the TCR parameter results in a value of 2.8, being very close to “waste-free” systems …”

Section: Resultsmentioning

confidence: 99%

“…Thus, the TCR offers a frame to compare different strategies at the benchmark scale. 43 However, this parameter cannot be determined for entries 1–3 due to the absence of information about downstream processes. For the strategy here presented, as a purification step is not required, wastes and wastewater are not produced, so the TCR parameter should be equal to zero.…”

Section: Resultsmentioning

confidence: 99%

“…However, by considering the PMI value of the organic compounds ( Table 4 , entry 4), the TCR parameter results in a value of 2.8, being very close to “waste-free” systems. 43 …”

Section: Resultsmentioning

confidence: 99%

“…This TCR parameter can be calculated according to the equation proposed by Onken et al (see Table ), where the worst scenario of waste treatment, such as the total incineration, is considered. Thus, the TCR offers a frame to compare different strategies at the benchmark scale . However, this parameter cannot be determined for entries 1–3 due to the absence of information about downstream processes.…”

Section: Resultsmentioning

confidence: 99%

“…However, by considering the PMI value of the organic compounds (Table 4, entry 4), the TCR parameter results in a value of 2.8, being very close to "waste-free" systems. 43 However, the PMI, E-factor, and TCR metrics do not cover issues related to the environmental and safety-hazard risks, which are considered by the EcoScale. 30 The EcoScale value comprises ecological and economical aspects in the evaluation of a reaction and may be very useful to perform a preliminary study of the life cycle assessment of a process.…”

Section: Sustainability Of the Biocatalytic Synthesis Of Pmes By Este...mentioning

confidence: 99%

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Sustainable Setups for the Biocatalytic Production and Scale-Up of Panthenyl Monoacyl Esters under Solvent-Free Conditions

Nieto

Bernal

Villa

et al. 2023

ACS Sustainable Chem. Eng.

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A sustainable scaling-up process for the biocatalytic production of new bioactive provitamin-B 5 monoacyl esters has been demonstrated. A solvent-free reaction protocol, based on the formation of eutectic mixtures between neat substrates, renders highly efficient direct esterification of free fatty acids (i.e., from C 6 to C 18 alkyl-chain length) with panthenol catalyzed by lipase. The scale-up from 0.5 to 500 g was evaluated by means of using several reaction systems (i.e., ultrasound assistance, orbital shaking, rotary evaporator, and mechanical stirring coupled to vacuum). For all reactor systems, the yield in panthenyl monoacyl esters was improved by increasing the length of the alkyl chain of the fatty acid (i.e., from 63% yield for panthenyl butyrate to 83% yield for panthenyl myristate). The best results (87−95% product yield, for all cases) were obtained upon a scale-up (50−500 g size) and when a vacuum system was coupled to the biocatalytic reaction unit. Under the optimized conditions, a 5-fold reduction of the amount of biocatalysts with respect to reactors without vacuum was achieved. The recovery and reuse of the immobilized enzyme for five operation cycles were also demonstrated. Finally, different metrics have been applied to assess the greenness of the solvent-free biocatalytic synthesis of panthenyl monoesters here reported.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…However, by considering the PMI value of the organic compounds ( Table 4 , entry 4), the TCR parameter results in a value of 2.8, being very close to “waste-free” systems. 43 …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Sustainability Of the Biocatalytic Synthesis Of Pmes By Este...mentioning

confidence: 99%

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Sustainable Setups for the Biocatalytic Production and Scale-Up of Panthenyl Monoacyl Esters under Solvent-Free Conditions

Nieto

Bernal

Villa

et al. 2023

ACS Sustainable Chem. Eng.

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Redox Biocatalysis in Lidocaine‐Based Hydrophobic Deep Eutectic Solvents: Non‐Conventional Media Outperform Aqueous Conditions

Zhang,

Lahmann,

Bittner

et al. 2024

ChemSusChem

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Redox biocatalysis is an important pillar of the chemical industry. Yet, the enzymes’ nature restricts most reactions to aqueous conditions, where the limited substrate solubility leads to unsustainable diluted biotranformations. Non‐aqueous media represent a strategic solution to conduct intensified biocatalytic routes. Deep eutectic solvents (DESs) are designable solvents that can be customized to meet specific application needs. Within the large design space of combining DES components (and ratios), hydrophobic DESs hold the potential to be both enzyme‐compatible – keeping the enzymes’ hydration –, and solubilizers for hydrophobic reactants. We explored two hydrophobic DESs, lidocaine/oleic acid, and lidocaine/decanoic acid, as reaction media for carbonyl reduction catalyzed by horse liver alcohol dehydrogenase, focusing on the effect of water contents and on maximizing substrate loadings. Enzymes remained highly active and stable in the DESs with 20 wt.% buffer, whereas the reaction performance in DESs outperformed the pure buffer system with hydrophobic substrates (e.g., cinnamaldehyde to form the industrially relevant cinnamyl alcohol), with a 2‐fold higher specific activity. Notably, the cinnamaldehyde reduction was for the first time performed at 800 mM (~100 g[[EQUATION]]L‐1) with full conversion, which opens up new avenues to industrial applications of hydrophobic DESs for enzyme catalysis.

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Kilogram‐Scale Synthesis of 4‐Chloro‐6‐(6‐methoxypyridin‐ 3‐yl)pyrimidine through a Suzuki–Miyaura Cross‐Coupling Using Micellar Catalysis

Isley,

Gallou

2023

Helvetica Chimica Acta

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A scalable and environmentally benign protocol for Suzuki–Miyaura cross‐coupling in water using the vitamin E derived surfactant TPGS‐750‐M is reported. The protocol is the simplest and most standard for such transformations under micellar catalysis that has been amply utilized within our own research and development portfolio over the last decade. The impact of the synthetic procedure is reenforced by the green Process Mass Intensity and Total Carbon Release.

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On the need for gate-to-gate environmental metrics in biocatalysis: fatty acid hydration catalyzed by oleate hydratases as a case study

Abstract: Biocatalysis will play a central role in future chemical processes, aiming at more sustainable strategies while keeping efficiency and economics. The mere use of enzymes does not assure the greenness,...

Cited by 20 publications

References 42 publications

Sustainable Setups for the Biocatalytic Production and Scale-Up of Panthenyl Monoacyl Esters under Solvent-Free Conditions

Sustainable Setups for the Biocatalytic Production and Scale-Up of Panthenyl Monoacyl Esters under Solvent-Free Conditions

Redox Biocatalysis in Lidocaine‐Based Hydrophobic Deep Eutectic Solvents: Non‐Conventional Media Outperform Aqueous Conditions

Kilogram‐Scale Synthesis of 4‐Chloro‐6‐(6‐methoxypyridin‐ 3‐yl)pyrimidine through a Suzuki–Miyaura Cross‐Coupling Using Micellar Catalysis

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