Catalysis in the preparation of fragrances and flavours

Chapuis, Christian; Jacoby, Denis

doi:10.1016/s0926-860x(01)00798-0

Cited by 161 publications

(93 citation statements)

References 164 publications

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“…Nonetheless, despite these advantages, hydroformylation has not been used much in fine chemicals with the exception of applications in vitamins [2,3] and in flavours and fragrances. [4,5] This may be in part related to the difficulty in controlling chemo-, regio-and stereoselectivity in the course of the reaction. Whereas good solutions now exist for the highly selective formation of linear aldehydes upon hydroformylation of terminal alkenes, the exclusive formation of branched aliphatic aldehydes remains an unsolved problem.…”

Section: Introductionmentioning

confidence: 99%

Rhodium‐Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles

Lambers‐Verstappen

Vries

2003

Adv Synth Catal

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Asymmetric hydroformylation of crotononitrile (1) and ally cyanide (2) was probed with the view to develop a synthesis for (R)-4-amino-2-methyl-butan-1-ol. Hydroformylation of 1 under a variety of conditions mainly led to hydrogenated product. Hydroformylation of 2 with Rh/tris(2,4-ditert-butylphenyl) phosphite gave good selectivity to the formylated nitrile with an n/iso of 77:23. Asymmetric hydroformylation of 2 could be accomplished in 66% ee using Rh/(R,S)-BINAPHOS.

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Section: Introductionmentioning

confidence: 99%

Rhodium‐Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles

Lambers‐Verstappen

Vries

2003

Adv Synth Catal

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“…This important area of catalytic chemistry has been the foundation for the development of numerous diverse, small-and large-scale commercial hydrogenation processes, which include synthesis of fine and specialty chemicals such as agrochemicals 1,2 , flavours and fragrances [3][4][5][6][7][8] , food additives [9][10][11][12][13][14][15][16] and pharmaceuticals [17][18][19][20][21] . The hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3--dihydroinden-1-one hydrochloride (1) to 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride (4), which is the last production step for the preparation of (4), is one such industrial important reaction.…”

Section: Introductionmentioning

confidence: 99%

reKinetics and Mass Transfer in the Hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy- -2,3-dihydroinden-1-one hydrochloride over Pt/C Catalyst

Zrnčević¹

2015

Chem.Biochem.Eng.Q.

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The liquid phase hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl) methylene)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride (1) over a 5 % Pt/C industrial catalyst was studied experimentally in a batch slurry reactor using methanol as a solvent. The catalyst was characterized by the adsorption techniques for specific surface area and pore volume, and by XRD for crystallinity. To investigate the intrinsic kinetics of the reaction, the effect of temperature, catalyst loading, hydrogen partial pressure and (1) concentration on the initial rate of hydrogenation was studied. The analysis of initial rate data showed that the gas-liquid, liquid-solid, and intraparticle mass-transfer resistances were not significant. The reaction scheme of (1) hydrogenation was proposed for the kinetic modelling. Apparent rate constants for all hydrogenation steps were calculated using a first order kinetic approach resulting in good agreement between the experimentally obtained and predicted concentrations. From the temperature dependence of rate constants, the activation energies of various reaction steps were calculated. The averaged activation energy of these steps was found to be 31.1 kJ mol -1 .

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“…Its main use is the reduction of olefins, but it also applies to the reduction of carbonyl compounds. 1 The hydrogenation reactions of unsaturated compounds bear great interest for modern industry. Although various catalytic and electrocatalytic processes have been presented that allow selective hydrogenation of unsaturated organic compounds, there is still room for improvement, particularly in the field of electrocatalysis.…”

Section: Introductionmentioning

confidence: 99%

“…After solvent evaporation, the products were analyzed by GC-FID. Isophorone (3,5,5-trimethylcyclohex-2-en-1-one) and cyclohex-2-en-1-one products were analyzed by 1 H NMR, using a Brüker AC-80 (80 MHz) spectrometer. 5 In another study, the electrocatalytic hydrogenation of cyclohexanone was used to test the performance (amount of cyclohexanol versus time of generated electrolysis at constant current) of original and versatile new materials for the electrocatalytic hydrogenation of organic substracts.…”

Section: Introductionmentioning

confidence: 99%

SPME-GC-FID method development for analyzing cyclohexanone hydrogenation products

Coelho¹,

Oliveira²,

Cardeal³

2009

J. Braz. Chem. Soc.

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Este trabalho apresenta o desenvolvimento de um método simples, rápido e preciso para análise dos produtos da hidrogenação eletrocatalítica da ciclohexanona com a técnica de microextração em fase sólida, usando cromatografia a gás com detector de ionização por chama. A otimização preliminar do método foi realizada através de ferramentas quimiométricas. Os resultados de LOD e LOQ foram 0,50% de conversão ou 0,78 mg L -1 e 1,20% de conversão ou 1,86 mg L -1 , respectivamente. A curva analítica demonstra boa linearidade (R 2 = 0,9936).This work presents a method development for analyzing electrocatalytic hydrogenation products of cyclohexanone with the simple, fast and accurate SPME, coupled with classic gas chromatographic methods using flame ionization detection. Preliminar method optimization was made using chemometric tools. LOD and LOQ obtained were 0.50% conversion or 0.78 mg L -1 and 1.20% conversion or 1.86 mg L -1 respectively. The analytical curve obtained displays good linearity (R 2 = 0.9936).

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Catalysis in the preparation of fragrances and flavours

Cited by 161 publications

References 164 publications

Rhodium‐Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles

Rhodium‐Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles

reKinetics and Mass Transfer in the Hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy- -2,3-dihydroinden-1-one hydrochloride over Pt/C Catalyst

SPME-GC-FID method development for analyzing cyclohexanone hydrogenation products

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