A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

Lima, Márcio V.F.; Menezes, Frederico Duarte de; Neto, Benício de Barros; Navarro, Marcelo

doi:10.1016/j.jelechem.2007.10.010

Cited by 12 publications

(4 citation statements)

References 41 publications

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“…Interestingly, hydrogenation over Ru/Al 2 O 3 gave carvone and hydrogenation over Rh/Al 2 O 3 gave thymol with high selectivity. The hydrogenation of pulegone has also been reported with catalysts like nickel nanoparticles, 161 palladium and cobalt supported on carbon 162,163 and via electrocatalytic hydrogenation 164 …”

Section: Syntheses From Other Raw Materialsmentioning

confidence: 99%

“…160 The hydrogenation 161 palladium and cobalt supported on carbon 162,163 and via electrocatalytic hydrogenation. 164 Unsaturated p-menthane analogues like α-phellandrene and limonene, as well as bicyclic terpenes like α-pinene and 3-carene have been used for commercial menthol synthesis in the past (see Lawrence et al, 1 Leffingwell and Shackleford 144 ). Especially pinene and carene, as the main components of crude sulphate turpentine generated in large amounts as waste in wood pulp production, are interesting raw materials for menthol production, not only because of high availability, but also their chirality.…”

Section: Synthe S E S From Other R Aw Materials Smentioning

confidence: 99%

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Synthesis of (−)‐menthol: Industrial synthesis routes and recent development

Dylong

Hausoul

Palkovits

et al. 2022

Flavour & Fragrance J

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Abstract(−)‐Menthol is one of the most popular aroma compounds worldwide. While in the past mostly extracted from mint plants, today (−)‐menthol synthesis from other raw materials is becoming more relevant. Common starting materials for menthol synthesis are m‐cresol, citral and myrcene, but also substrates like menthone, mono‐ and bicyclic terpenes and terpenoids have been used for this purpose in the past. As for many applications (−)‐menthol of high purity is required, asymmetric syntheses and enantiomeric resolution of obtained raw products are applied for menthol production. This review gives an overview on the most important synthetic menthol production processes of the companies Symrise, Takasago and BASF and relevant literature in the field of menthol synthesis with a focus on the last 20 years.

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Section: Syntheses From Other Raw Materialsmentioning

confidence: 99%

Section: Synthe S E S From Other R Aw Materials Smentioning

confidence: 99%

Synthesis of (−)‐menthol: Industrial synthesis routes and recent development

Dylong

Hausoul

Palkovits

et al. 2022

Flavour & Fragrance J

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“…For ECH, chemisorbed hydrogen, (H)M, must be on the surface of a catalyst, M, for surface-mediated hydrogenation. The Ménard and the Navarro groups suggested the mechanisms of ECH for unsaturated organic compounds, − and modified reactions for the specific case of ECH of FF are shown below. In acidic electrolytes, the chemisorbed hydrogen is formed according to reaction and is formed according to reaction in alkaline electrolytes.…”

Section: Introductionmentioning

confidence: 99%

Electrocatalytic Hydrogenation and Hydrogenolysis of Furfural and the Impact of Homogeneous Side Reactions of Furanic Compounds in Acidic Electrolytes

Jung

Biddinger

2016

ACS Sustainable Chem. Eng.

109

174

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The electrochemical hydrogenation and hydrogenolysis (ECH) of furfural (FF) on a copper electrocatalyst has been investigated to produce biofuels and fine chemicals in an H-type batch reactor at room temperature. We report a systematic study of ECH of FF to gain a better understanding of the relationships between products and reaction conditions: current density, electrolyte, and cosolvent ratio in acidic solutions. The acidity of electrolytes had the most significant impact on the product distribution. Mildly acidic electrolytes mainly produced furfuryl alcohol (FA), while strongly acidic electrolytes produced both 2-methyl furan (MF) and FA. Also, the yield of products depended on the current density and reaction time when equivalent charge was transferred to the reaction. However, the mole balance accounting for FF, MF, and FA was not higher than 70% in any reaction condition when the theoretical amount of electrons for complete MF production from FF (e–/FF = 4) was transferred to the system. The investigation of nonelectrochemical homogeneous side reactions suggested that the low mole balance in a mildly acidic electrolyte may be from the charge transfer promoted side reactions on the copper electrode. On the other hand, it was shown that the low mole balance in strongly acidic electrolytes was due to homogeneous side reactions.

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“…The vast majority of hydrogenation catalysts consists of metals that are either known to catalyse thermal hydrogenations such as palladium, 32,33,37,42,81,82,84,112,195,196 ruthenium, 32,88,118,191,[197][198][199][200][201] and nickel 33,108,178,199,[202][203][204][205][206][207][208][209] or known to easily form active hydrogen species on their surface under reductive conditions like platinum. 21,22,24,48,122,134,136,152,165,182,[210][211][212][213][214][215] The other frequently reported catalyst is copper, which is mainly applied for the hydrogenation of furfural derivatives…”

Section: Overviewmentioning

confidence: 99%