MoO3-MCM-41 materials as effective catalysts in Prins reaction of isoprenol with butanal followed by esterification in one-pot reaction arrangement

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F24%3A43930081" target="_blank" >RIV/60461373:22310/24:43930081 - isvavai.cz</a>

Result on the web

<a href="https://link.springer.com/article/10.1007/s11164-024-05437-9" target="_blank" >https://link.springer.com/article/10.1007/s11164-024-05437-9</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11164-024-05437-9" target="_blank" >10.1007/s11164-024-05437-9</a>

Result language

angličtina

Original language name

MoO3-MCM-41 materials as effective catalysts in Prins reaction of isoprenol with butanal followed by esterification in one-pot reaction arrangement

Original language description

Prins reaction of isoprenol with butanal provides important intermediate 4-methyl-2-propyltetrahydro-2H-pyran-4-ol, which can be esterified to 4-methyl-2-propyltetrahydro-2H-pyran-4-yl acetate. This desired fragrance with fruity and rose scent is known, e.g., as Clarycet (R). Molybdenum-modified MCM-41 materials were obtained by a wet impregnation method using a water solution of ammonium molybdate. We prepared several materials with different MoO3 loadings. These materials were thoroughly characterized (nitrogen physisorption, acidity-temperature-programmed desorption, elemental composition, etc.). The activity of prepared materials was tested in Prins reaction of isoprenol with butanal in batch arrangement. The influence of various reaction conditions (catalyst type, solvent, and water addition) was tested. We showed that modification of MCM-41 with MoO3 led to a significant increase of catalytic activity (butanal conversion at 4 h of reaction: 7% for nonmodified MCM-41 compared to 93% for material 5 wt% of MoO3-MCM-41). Water addition to the reaction mixture positively influenced the selectivity of the desired substituted tetrahydropyranol (selectivity &gt; 70%). Mo-modified materials were also active in the esterification of 4-methyl-2-propyltetrahydro-2H-pyran-4-ol with acetanhydride to 4-methyl-2-propyltetrahydro-2H-pyran-4-yl acetate providing desired product after 5 h with 100% selectivity and total conversion. Reaction in the &quot;one-pot&quot; arrangement was also performed.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2024

Confidentiality

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

Name of the periodical

RESEARCH ON CHEMICAL INTERMEDIATES

ISSN

0922-6168

e-ISSN

1568-5675

Volume of the periodical

50

Issue of the periodical within the volume

November 2024

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

18

Pages from-to

"5781–5798"

UT code for WoS article

001350827200001

EID of the result in the Scopus database

2-s2.0-85208808944