Acid catalyzed acetalization of aldehydes with diols resulting into the formation of fragrant cyclic acetals
The result's identifiers
Result code in 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>
Alternative codes found
RIV/60461373:22810/19:43918550
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Acid catalyzed acetalization of aldehydes with diols resulting into the formation of fragrant cyclic acetals
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/LO1613" target="_blank" >LO1613: Future materials</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Reaction Kinetics Mechanisms and Catalysis
ISSN
1878-5190
e-ISSN
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Volume of the periodical
127
Issue of the periodical within the volume
2
Country of publishing house
US - UNITED STATES
Number of pages
14
Pages from-to
727-740
UT code for WoS article
000475580200012
EID of the result in the Scopus database
2-s2.0-85066778815