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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

RESEARCH ON CHEMICAL INTERMEDIATES

ISSN

0922-6168

e-ISSN

1568-5675

Svazek periodika

50

Číslo periodika v rámci svazku

November 2024

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

18

Strana od-do

"5781–5798"

Kód UT WoS článku

001350827200001

EID výsledku v databázi Scopus

2-s2.0-85208808944