Preyssler Heteropolyacids in the Self‐Etherification of 5‐Hydroxymethylfurfural to 5,5′‐[Oxybis(methylene)]bis‐2‐furfural Under Mild Reaction Conditions

Páez, Alexander; Rojas, Hugo; Portilla, Omar; Sathicq, Ángel Gabriel; Afonso, Carlos A. M.; Romanelli, Gustavo Pablo; Martínez, José Javier Pérez-Fadón

doi:10.1002/cctc.201700457

Cited by 21 publications

(16 citation statements)

References 33 publications

(31 reference statements)

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“…The results obtained for HPA/SiO 2 , HPA/Al 2 O 3 and P/SiO 2 ‐Fe 3 O 4 are listed in Table , and Figure shows the FTIR spectra of pyridine adsorbed on those same materials. Also, for comparison, the nature of acid sites of the HPA‐Preyssler sample are also displayed, which are in agreement with a previous report . Although in supported heteropolyacids the conversion to OBMF decreases compared with the bulk, the selectivity depends on the support used (see entries 2 and 3).…”

Section: Resultssupporting

confidence: 89%

“…Recently, our research group reported the synthesis of OBMF by the etherification of 5‐HMF under mild reaction conditions using HPA‐Preyssler. The etherification of 5‐HMF was favored by the higher Brönsted acidity, and the production of OBMF was optimized using bulk HPA‐Preyssler, obtaining a selectivity of 95% with 85% of conversion of 5‐HMF at 5 h and 343 K. However, Preyssler heteropolyacids present a low surface area and for this reason are generally deposited on different supports, but the interaction between the support and the heteropolyacid decreases the acidity and consequently, the conversion . The lowest proton mobility when the HPA‐Preyssler is supported depends on the negative charge distribution in the heteropolyanion oxygens and the electrostatic interaction of the HPA‐Preyssler with ‐OH surface groups of the support, thus a convenient method is the use of composites that can immobilize the heteropolyacid.…”

Section: Introductionmentioning

confidence: 99%

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Etherification of Hydroxymethylfurfural with Preyssler Heteropolyacids Immobilized on Magnetic Composites

et al. 2018

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A thermodynamic study about the stability of intermediates in the reaction of 5-hydroxymethylfurfural (HMF) over Preyssler heteropolyacids (HPA-Preyssler) was performed to explain the self-etherification or oxidation of HMF. Although the product of etherification forms in higher proportion when a heteropolyacid is used, other oxidation products are also observed. The availability of HPA-Preyssler protons is essential to conduct the self-etherification; however, this is not favored when the heteropolyacid is immobilized on metallic oxides and besides, the reusability of the supported heteropolyacid is low. In this study, magnetic composites were used to incorporate the HPA-Preyssler to prevent the formation of by-products and to facilitate the separation from the reaction medium. The results of catalytic tests and acidity analysis demonstrated a better proton availability, and the recovery of glutaraldehyde of the heteropolyacid decreases the leaching of immobilized HPA-Preyssler when the composite is reused. The reaction was optimized obtaining a maximum yield to OBMF near 70% in 5 h.[a] Dr.

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Section: Resultssupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Etherification of Hydroxymethylfurfural with Preyssler Heteropolyacids Immobilized on Magnetic Composites

et al. 2018

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“…This result is directly related to the acid strength. In accordance with the potentiometric titration results, it was found that HPA‐Preyssler was more acid than Preyssler‐Mo . The lowest yield reached with HPA‐Keggin was due to its weak Brönsted‐type acidity with a value Ho=‐13.60, while HPA‐Preyssler had an acidity Ho=‐14.52 .…”

Section: Resultssupporting

confidence: 88%

Selective Catalytic Dehydration of Xylose to Furfural and Fructose and Glucose to 5‐Hydroximethylfurfural (HMF) Using Preyssler Heteropolyacid

et al. 2020

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Catalytic dehydration of xylose to yield furfural was studied by testing different heteropolyacid-type catalysts. Preyssler heteropolyacid (HPA-Preyssler) (H 14 [NaP 5 W 30 O 110 ]) was the most efficient. Under the optimal reaction conditions, xylose was dehydrated into furfural with 73% of yield and 95% of selectivity using DMSO as solvent at 140°C for 4 h. The HPA-Preyssler catalyst also exhibited good catalytic activity in the dehydration of fructose and glucose to yield 5-hydroxymeth-ylfurfural (HMF). Thus, from fructose a yield and selectivity to HMF of 97% and 98%, respectively, was obtained in just 10 min, while from glucose, 91% of conversion and 23% of yield were obtained after 9 h. An easy and efficient methodology for the recovery and reuse of HPA-Preyssler in at least six reaction cycles without appreciable loss of its initial catalytic activity is reported.

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“…The catalytic reactivity of the heteropolyacids was Preyssler > Preyssler‐Mo > Keggin (entries 11–13). The reactivity of the Preyssler heteropolyacid and Pressyler‐Mo heteropolyacid was similar to that reported in our previous work on the self‐etherification of HMF, whereas Keggin heteropolyacid activity was lower, possibly due to its lower Brönsted acid strength . However, under long reaction times, a decrease in yield in the presence of Preyssler (entry 11) was observed.…”

Section: An Overview Of the Main Reported Catalytic Systems For The Psupporting

confidence: 87%

Efficient Continuous Production of the Biofuel Additive 5‐(t‐Butoxymethyl) Furfural from 5‐Hydroxymethylfurfural

et al. 2019

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The catalytic etherification of 5‐hydroxymethylfurfural (HMF) with t‐butanol to a biofuel additive 5‐(t‐butoxymethyl) furfural (t‐BMF) is studied by screening 27 heterogeneous protic and/or Lewis acids. Preyssler heteropolyacid H14[NaP5W30O110] and Montmorillonite‐based CLOI_CSP catalysts are identified as the most efficient ones, allowing the etherification to reach the t‐BMF/HMF equilibrium faster (≈1:1), thus promoting minimum side reactions. Further optimization of the batch experimental conditions, namely catalyst loading, temperature, HMF concentration, time, t‐BMF stability, and additives, allows the t‐BMF/HMF equilibrium to be reached in less than 3 h with outstanding selectivity >95%. Under optimized conditions, CLOI_CSP is reused for four cycles without significant loss of efficiency. In addition, it exhibits high efficiency under flow conditions, allowing continuous production of t‐BMF up to 0.7 g t‐BMF g−1 catalyst min−1 at high concentrations of HMF.

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Preyssler Heteropolyacids in the Self‐Etherification of 5‐Hydroxymethylfurfural to 5,5′‐[Oxybis(methylene)]bis‐2‐furfural Under Mild Reaction Conditions

Cited by 21 publications

References 33 publications

Etherification of Hydroxymethylfurfural with Preyssler Heteropolyacids Immobilized on Magnetic Composites

Etherification of Hydroxymethylfurfural with Preyssler Heteropolyacids Immobilized on Magnetic Composites

Selective Catalytic Dehydration of Xylose to Furfural and Fructose and Glucose to 5‐Hydroximethylfurfural (HMF) Using Preyssler Heteropolyacid

Efficient Continuous Production of the Biofuel Additive 5‐(t‐Butoxymethyl) Furfural from 5‐Hydroxymethylfurfural

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