A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta, Guido; Sharley, James S.; Baxendale, Ian R.

doi:10.3762/bjoc.17.90

Cited by 43 publications

(27 citation statements)

References 582 publications

(735 reference statements)

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“…Flow chemistry is another strategy to improve efficiency and productivity that has attracted increasing attention in metathesis and the fragrance industry [ 80 , 81 , 82 , 83 , 84 ]. In 2019, Collins et al investigated the synthesis of macrocyclic musks via RCM, featuring the systematic evaluation of batch and continuous flow protocols [ 82 ].…”

Section: Synthesis Of Fragrances Via Ring-closing Metathesismentioning

confidence: 99%

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Lin¹,

Huang²,

Ouyang³

et al. 2022

Molecules

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With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area.

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Section: Synthesis Of Fragrances Via Ring-closing Metathesismentioning

confidence: 99%

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Lin¹,

Huang²,

Ouyang³

et al. 2022

Molecules

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show abstract

“…Since continuous production and suitable reactors are getting more attention [24] and some believe that it will be the next milestone for industry [25,26], the aim of this research was to first establish a continuous reactor at high pressure and then investigate the influence of pressure on the reaction sequence to produce Neu5Ac.…”

Section: Introductionmentioning

confidence: 99%

Shift of reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

Reich¹,

Aßmann²,

Hölting³

et al. 2022

Preprint

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The importance of a chemical that helps fight against Influenca is, in times of a global pandemic, self-evident. Many researchers see the continuous production in chemical industry as its next stepping stone. For these reasons, the synthesis of N-Acetylneuraminic acid in a continuous fixed-bed reactor by an immobilized epimerase and aldolase was investigated in detail. The immobilized enzymes showed high stability with half-life times > 173 days under storage condition (6 °C in buffer) and reusability over 50 recycling steps and was characterized regarding the reaction kinetics (initial rate) and scalability (different lab scales) in a batch reactor. In a continuous flow reactor reaction kinetics were studied. A high pressure circular reactor (up to 130 MPa) was applied for investigation of changes in the position of the reaction equilibrium. By this, equilibrium conversion, selectivity and yield were increased from 57.9% to 63.9%, 81.9% to 84.7% and 47.5% to 54.1%, respectively. This indicates a reduction in molar volume from GlcNAc and Pyr to Neu5Ac. The circular reactor in particular showed great potential to study reactions at high pressure while allowing for easy sampling. Additionally, an increase in affinity of pyruvate towards both tested enzymes was found with the application of pressure as measured in a decrease of for the epimerase and for the aldolase of 108 to 42 mM and 91 to 37 mM, respectively.

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“…Since continuous production and suitable reactors are receiving more attention [ 24 ], and some believe that this will be the next stepping stone for industry [ 25 – 26 ], the aim of this research was to first establish a continuous reactor at high pressure, and then to investigate the influence of pressure on the reaction sequence to produce Neu5Ac. While high-pressure processes that operate semi-continuously already exist in the food industry, continuous reactors containing a high-performance liquid chromatography (HPLC) pump and a fixed-bed reactor at high pressure are still a relatively new concept.…”

Section: Introductionmentioning

confidence: 99%

Shift of the reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

Reich¹,

Aßmann²,

Hölting³

et al. 2022

Beilstein J. Org. Chem.

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The importance of a compound that helps fight against influenza is, in times of a pandemic, self-evident. In order to produce these compounds in vast quantities, many researchers consider continuous flow reactors in chemical industry as next stepping stone for large scale production. For these reasons, the synthesis of N-acetylneuraminic acid (Neu5Ac) in a continuous fixed-bed reactor by an immobilized epimerase and aldolase was investigated in detail. The immobilized enzymes showed high stability, with half-life times > 173 days under storage conditions (6 °C in buffer) and reusability over 50 recycling steps, and were characterized regarding the reaction kinetics (initial rate) and scalability (different lab scales) in a batch reactor. The reaction kinetics were studied in a continuous flow reactor. A high-pressure circular reactor (up to 130 MPa) was applied for the investigation of changes in the position of the reaction equilibrium. By this, equilibrium conversion, selectivity, and yield were increased from 57.9% to 63.9%, 81.9% to 84.7%, and 47.5% to 54.1%, respectively. This indicates a reduction in molar volume from N-acetyl-ᴅ-glucosamine (GlcNAc) and pyruvate (Pyr) to Neu5Ac. In particular, the circular reactor showed great potential to study reactions at high pressure while allowing for easy sampling. Additionally, an increase in affinity of pyruvate towards both tested enzymes was observed when high pressure was applied, as evidenced by a decrease of KI for the epimerase and KM for the aldolase from 108 to 42 mM and 91 to 37 mM, respectively.

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A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Cited by 43 publications

References 582 publications

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Shift of reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

Shift of the reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

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