Acid catalyzed acetalization of aldehydes with diols resulting into the formation of fragrant cyclic acetals

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F19%3A43918550" target="_blank" >RIV/60461373:22310/19:43918550 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22810/19:43918550

Výsledek na webu

<a href="https://link.springer.com/content/pdf/10.1007%2Fs11144-019-01595-9.pdf" target="_blank" >https://link.springer.com/content/pdf/10.1007%2Fs11144-019-01595-9.pdf</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11144-019-01595-9" target="_blank" >10.1007/s11144-019-01595-9</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Acid catalyzed acetalization of aldehydes with diols resulting into the formation of fragrant cyclic acetals

Popis výsledku v původním jazyce

The influence of reaction conditions (amount and type of the catalyst, the reaction temperature, the type of the solvent) on the reaction course of the acetalization of aldehydes with diols was tested in this paper. The optimization of reaction conditions was performed on model reaction, acetalization of 2-methylpentanal by 2-methyl-2-propyl-1,3-propanediol leading to the formation of fragrant compound 2-(1-methylbutyl)-5-methyl-5-propyl-1,3-dioxane (Troenan). p-Toluenesulfonic acid was used as an active homogeneous catalyst. It appeared to be advantageous not to use any solvent in the reaction. Using 0.3 wt% of the catalyst the almost total conversion of 2-methylpentanal was achieved after 240 min of reaction at room temperature while the selectivity to the desired product was about 98%. The optimized reaction conditions were applied to the preparation of four cyclic fragrant acetals (namely 2-hexyl-1,3-dioxolane, 2-hexyl-4-methyl-1,3-dioxolane, 2-benzyl-5-hydroxy-1,3-dioxane and 2-(1-methylbutyl)-5-methyl-5-propyl-1,3-dioxane) in larger scale; and these were sensory evaluated after purification step. Prepared heterogeneous catalysts, acid modified montmorillonite (MMT) K-10 (treated by H2SO4, HNO3, and HCl) were successful in the model reaction. The conversion of 2-methylpentanal over 90% was achieved using acid modified MMT after 300 min of reaction at room temperature, the selectivity to the desired product was about 98%. MMT/H2SO4 can be used in the model reaction four times without any change in the reaction course, what makes it promising for the further application. © 2019, Akadémiai Kiadó, Budapest, Hungary.

Název v anglickém jazyce

Acid catalyzed acetalization of aldehydes with diols resulting into the formation of fragrant cyclic acetals

Popis výsledku anglicky

The influence of reaction conditions (amount and type of the catalyst, the reaction temperature, the type of the solvent) on the reaction course of the acetalization of aldehydes with diols was tested in this paper. The optimization of reaction conditions was performed on model reaction, acetalization of 2-methylpentanal by 2-methyl-2-propyl-1,3-propanediol leading to the formation of fragrant compound 2-(1-methylbutyl)-5-methyl-5-propyl-1,3-dioxane (Troenan). p-Toluenesulfonic acid was used as an active homogeneous catalyst. It appeared to be advantageous not to use any solvent in the reaction. Using 0.3 wt% of the catalyst the almost total conversion of 2-methylpentanal was achieved after 240 min of reaction at room temperature while the selectivity to the desired product was about 98%. The optimized reaction conditions were applied to the preparation of four cyclic fragrant acetals (namely 2-hexyl-1,3-dioxolane, 2-hexyl-4-methyl-1,3-dioxolane, 2-benzyl-5-hydroxy-1,3-dioxane and 2-(1-methylbutyl)-5-methyl-5-propyl-1,3-dioxane) in larger scale; and these were sensory evaluated after purification step. Prepared heterogeneous catalysts, acid modified montmorillonite (MMT) K-10 (treated by H2SO4, HNO3, and HCl) were successful in the model reaction. The conversion of 2-methylpentanal over 90% was achieved using acid modified MMT after 300 min of reaction at room temperature, the selectivity to the desired product was about 98%. MMT/H2SO4 can be used in the model reaction four times without any change in the reaction course, what makes it promising for the further application. © 2019, Akadémiai Kiadó, Budapest, Hungary.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LO1613" target="_blank" >LO1613: Výzkum nových materiálů pro chemický průmysl</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

Reaction Kinetics Mechanisms and Catalysis

ISSN

1878-5190

e-ISSN

—

Svazek periodika

127

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

14

Strana od-do

727-740

Kód UT WoS článku

000475580200012

EID výsledku v databázi Scopus

2-s2.0-85066778815