Solvent effects in hydrodeoxygenation of furfural-acetone aldolcondensation products over Pt/TiO2catalyst

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62243136%3A_____%2F17%3AN0000021" target="_blank" >RIV/62243136:_____/17:N0000021 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22320/17:43901959

Výsledek na webu

<a href="http://www.sciencedirect.com/science/article/pii/S0926860X16305622?via=ihub" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0926860X16305622?via=ihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/https://doi.org/10.1016/j.apcata.2016.11.023" target="_blank" >https://doi.org/10.1016/j.apcata.2016.11.023</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Solvent effects in hydrodeoxygenation of furfural-acetone aldolcondensation products over Pt/TiO2catalyst

Popis výsledku v původním jazyce

The solvent effects on hydrodeoxygenation (HDO) of 4-(2-furyl)-3-buten-2-one (F-Ac) over Pt/TiO2cat-alyst were investigated at T = 200◦C and P(H2) = 50 bar. The initial reactant is the main product of aldolcondensation between furfural and acetone, which constitutes a promising route for the production ofbio-based chemicals and fuels. A sequence of experiments was performed using a selection of polar sol-vents with different chemical natures: protic (methanol, ethanol, 1-propanol, 2-propanol, 1-pentanol)and aprotic (acetone, tetrahydrofuran (THF), n,n-dimethylformamide (DMF)). In case of protic solvents, agood correlation was found between the polarity parameters and conversion. Consequently, the highesthydrogenation rate was observed when 2-propanol was used as a solvent. In contrast, the hydrogenationactivity in presence of aprotic solvents was related rather to solvent-catalyst interactions. Thus, the ini-tial hydrogenation rate declined in order Acetone > THF > DMF, i.e. in accordance with the increase in thenucleophilic donor number and solvent desorption energy. Regarding the product distribution, a complexmixture of intermediates was obtained, owing to the successive hydrogenation (aliphatic C C, furanicC C and ketonic C O bonds), ring opening (via C O hydrogenolysis) and deoxygenation reactions. Basedon the proposed reaction scheme for the conversion of F-Ac into octane, the influence of the studiedsolvents over the cascade catalytic conversion is discussed. A significant formation of cyclic saturatedcompounds such as 2-propyl-tetrahydropyran and 2-methyl-1,6-dioxaspiro[4,4]nonane took place viaundesirable side reactions of cyclization and isomerization. The best catalytic performance was foundwhen using acetone and 2-propanol as solvents, achieving significant yields of 4-(2-tetrahydrofuryl)-butan-2-ol (28.5–40.4%) and linear alcohols (6.3–10.4%). The better performance of these solvents maybe associated with a lower activation energy barrier for key intermediate products, due to their mod-erate interaction with the reactant and the catalyst. In case of methanol and DMF, undesired reactionsbetween the reactant and the solvent took place, leading to a lower selectivity towards the targetedhydrodeoxygenated products.

Název v anglickém jazyce

Solvent effects in hydrodeoxygenation of furfural-acetone aldolcondensation products over Pt/TiO2catalyst

Popis výsledku anglicky

The solvent effects on hydrodeoxygenation (HDO) of 4-(2-furyl)-3-buten-2-one (F-Ac) over Pt/TiO2cat-alyst were investigated at T = 200◦C and P(H2) = 50 bar. The initial reactant is the main product of aldolcondensation between furfural and acetone, which constitutes a promising route for the production ofbio-based chemicals and fuels. A sequence of experiments was performed using a selection of polar sol-vents with different chemical natures: protic (methanol, ethanol, 1-propanol, 2-propanol, 1-pentanol)and aprotic (acetone, tetrahydrofuran (THF), n,n-dimethylformamide (DMF)). In case of protic solvents, agood correlation was found between the polarity parameters and conversion. Consequently, the highesthydrogenation rate was observed when 2-propanol was used as a solvent. In contrast, the hydrogenationactivity in presence of aprotic solvents was related rather to solvent-catalyst interactions. Thus, the ini-tial hydrogenation rate declined in order Acetone > THF > DMF, i.e. in accordance with the increase in thenucleophilic donor number and solvent desorption energy. Regarding the product distribution, a complexmixture of intermediates was obtained, owing to the successive hydrogenation (aliphatic C C, furanicC C and ketonic C O bonds), ring opening (via C O hydrogenolysis) and deoxygenation reactions. Basedon the proposed reaction scheme for the conversion of F-Ac into octane, the influence of the studiedsolvents over the cascade catalytic conversion is discussed. A significant formation of cyclic saturatedcompounds such as 2-propyl-tetrahydropyran and 2-methyl-1,6-dioxaspiro[4,4]nonane took place viaundesirable side reactions of cyclization and isomerization. The best catalytic performance was foundwhen using acetone and 2-propanol as solvents, achieving significant yields of 4-(2-tetrahydrofuryl)-butan-2-ol (28.5–40.4%) and linear alcohols (6.3–10.4%). The better performance of these solvents maybe associated with a lower activation energy barrier for key intermediate products, due to their mod-erate interaction with the reactant and the catalyst. In case of methanol and DMF, undesired reactionsbetween the reactant and the solvent took place, leading to a lower selectivity towards the targetedhydrodeoxygenated products.

Druh

J_ost - Ostatní články v recenzovaných periodicích

CEP obor

—

OECD FORD obor

20402 - Chemical process engineering

Projekt

<a href="/cs/project/LO1606" target="_blank" >LO1606: Rozvoj Centra UniCRE</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Applied Catalysis A: General

ISSN

0926-860X

e-ISSN

—

Svazek periodika

—

Číslo periodika v rámci svazku

530

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

10

Strana od-do

174-183

Kód UT WoS článku

—

EID výsledku v databázi Scopus

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