Hydrogenation of C6 dienic compounds using ruthenium catalysts

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Hydrogenation of C6 dienic compounds using ruthenium catalysts

Popis výsledku v původním jazyce

Leaf alcohol ((Z)-hex-3-en-1-ol) is a colorless liquid with a strong, fresh odor of grass and leaves. This alcohol is widely used in the production of fragrance compositions. Literature offers different ways to synthesize this alcohol, but they are usually difficult multistage procedures with small yields [1]. The easiest way for the preparation of (Z)-hex-3-en-1-ol is based on hydrogenation of cheap and simply available sorbic acid, sorbic alcohol or butyl ester of sorbic acid. Selective hydrogenation of mentioned C6 compounds was performed with high selectivity in the presence of a ruthenium half sandwich complex with the structure [Cp*Ru(diene)]OTf. The influence of the reaction conditions (temperature, pressure, catalyst amount, solvent type) on the reaction rate and selectivity in the hydrogenation of dienic compounds have been studied in details [2,3]. The influence of various diene ligands on the process of hydrogenation has not yet been studied. This work was focused on the preparation of model ruthenium complexes of the type [Cp*Ru(COD)]ClO4 and [Cp*Ru(NBD)]BF4 (COD = 1,5 - cyclooctadiene, NBD = bicyclo [2.2.1] hepta-5-diene) (Fig. 1) and their use for the selective hydrogenation of C6 dienic compounds. The model compounds were sorbic acid and butylsorbate. Figure 1. Prepared ruthenium half sandwich complexes Hydrogenation was performed in homogeneous arrangement. Diethyl ether was chosen as a solvent. Reaction conditions were set to 50 °C and 4 MPa. All the above-mentioned C6 dienic compounds were hydrogenated to corresponding (Z)-hex-3-enoic compounds with high selectivity (up to 95 %).

Název v anglickém jazyce

Hydrogenation of C6 dienic compounds using ruthenium catalysts

Popis výsledku anglicky

Leaf alcohol ((Z)-hex-3-en-1-ol) is a colorless liquid with a strong, fresh odor of grass and leaves. This alcohol is widely used in the production of fragrance compositions. Literature offers different ways to synthesize this alcohol, but they are usually difficult multistage procedures with small yields [1]. The easiest way for the preparation of (Z)-hex-3-en-1-ol is based on hydrogenation of cheap and simply available sorbic acid, sorbic alcohol or butyl ester of sorbic acid. Selective hydrogenation of mentioned C6 compounds was performed with high selectivity in the presence of a ruthenium half sandwich complex with the structure [Cp*Ru(diene)]OTf. The influence of the reaction conditions (temperature, pressure, catalyst amount, solvent type) on the reaction rate and selectivity in the hydrogenation of dienic compounds have been studied in details [2,3]. The influence of various diene ligands on the process of hydrogenation has not yet been studied. This work was focused on the preparation of model ruthenium complexes of the type [Cp*Ru(COD)]ClO4 and [Cp*Ru(NBD)]BF4 (COD = 1,5 - cyclooctadiene, NBD = bicyclo [2.2.1] hepta-5-diene) (Fig. 1) and their use for the selective hydrogenation of C6 dienic compounds. The model compounds were sorbic acid and butylsorbate. Figure 1. Prepared ruthenium half sandwich complexes Hydrogenation was performed in homogeneous arrangement. Diethyl ether was chosen as a solvent. Reaction conditions were set to 50 °C and 4 MPa. All the above-mentioned C6 dienic compounds were hydrogenated to corresponding (Z)-hex-3-enoic compounds with high selectivity (up to 95 %).

Druh

D - Stať ve sborníku

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

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Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název statě ve sborníku

PROCEEDINGS of the 6th International Conference on Chemical Technology

ISBN

978-80-86238-77-7

ISSN

2336-8128

e-ISSN

neuvedeno

Počet stran výsledku

6

Strana od-do

336-341

Název nakladatele

Česká společnost průmyslové chemie (ČSPCH)

Místo vydání

Praha

Místo konání akce

Mikulov

Datum konání akce

16. 4. 2018

Typ akce podle státní příslušnosti

WRD - Celosvětová akce

Kód UT WoS článku

000461293800062