Synthesis of fragrance compounds from renewable resources: the aqueous biphasic hydroformylation of acyclic terpenes

Vieira, Camila Grossi; Freitas, Marina Caneschi de; Oliveira, Kelley C.B.; Faria, Amanda de Camargo; Santos, Eduardo N. dos; Gusevskaya, Elena V.

doi:10.1039/c4cy01020e

Cited by 24 publications

(2 citation statements)

References 39 publications

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“…In the past decade, Gusevskaya and coworkers developed a series of catalytic transformations of renewable alkenes to gain access to new fragrant molecules [ 30 , 131 , 132 , 133 , 134 , 135 , 136 , 137 , 138 ]. For example, they subjected myrtenol and nopol to the synthesis of polycyclic fragrances via hydroformylation and the subsequent intramolecular acetalization [ 131 ].…”

Section: Synthesis Of Heterocyclic Fragrances Via Addition-type React...mentioning

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 Heterocyclic Fragrances Via Addition-type React...mentioning

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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“…They constitute an important building block for the fine chemical industry. Hydroformylation of these naturally occurring terpenes such as camphene can be a promising synthetic route for obtaining aldehydes, which can be used in the perfume, flavor, and pharmaceutical industries 1‐8 . The main problem in terpene hydroformylation, and particularly camphene is its low reactivity as compared to other linear olefins, resulting in prolonged reaction times and severe reaction conditions (>100°C, >5 MPa syngas pressure) 3–5 .…”

Section: Introductionmentioning

confidence: 99%

Kinetics of hydroformylation of camphene using rhodium‐phosphite catalyst

Pagar

Rajurkar

Deshpande

2020

Int J of Chemical Kinetics

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Kinetics of hydroformylation of camphene was investigated in the presence of [Rh(CO) 2 (acac)]/P(OPh) 3 catalyst in a temperature range of 363-383 K. The influence of parameters such as stirring speed, camphene, catalyst, ligand concentrations, and partial pressures of H 2 and CO on the activity and selectivity of the catalyst has been studied. The rate showed a first-order dependence with respect to catalyst and camphene concentrations. The effect of partial pressure of hydrogen showed fractional order dependence. The plots of rate versus excess ligand, that is, (P(OPh) 3 ) concentration and rate versus CO partial pressure passed through maxima and showed typical substrate/ligand inhibited kinetics. An empirical rate equation has been proposed and found to be in good agreement with the observed rate data. The kinetic parameters and activation energy were also evaluated. K E Y W O R D Scamphene, homogeneous, hydroformylation, kinetics, rhodium-phosphite Int J Chem Kinet. 2020;52:485-495.

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Hydroformylation Catalysts for the Synthesis of Fine Chemicals

Pereira,

Carrilho,

Rodrigues

et al. 2024

Catalysis for a Sustainable Environment

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Synthesis of fragrance compounds from renewable resources: the aqueous biphasic hydroformylation of acyclic terpenes

Abstract: Several compounds useful as components of synthetic perfumes and cosmetics were obtained from linalool, nerolidol and β-citronelleneviarhodium-catalyzed aqueous biphasic hydroformylation.

Cited by 24 publications

References 39 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

Kinetics of hydroformylation of camphene using rhodium‐phosphite catalyst

Hydroformylation Catalysts for the Synthesis of Fine Chemicals

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