Catalytic self-etherification of 5-hydroxymethylfurfural to 5,5′(oxy-bis(methylene))bis-2-furfural over zeolite catalysts: effect of pore structure and acidity

Zhang, Pilan; Yang, Jie; Hu, Hualei; Hu, Danxin; Gan, Jiang; Zhang, Yexin; Chen, Chunlin; Li, Xiaoqiang; Wang, Lei; Zhang, Jian

doi:10.1039/d0cy00733a

Cited by 16 publications

(19 citation statements)

References 39 publications

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“…Because the dimerization of C 6 H 8 O 4 could form a compound with the formula of C 12 H 16 O 8 , we proposed that the compound C 12 H 16 O 8 (18.23 min) should be formed by the aldol condensation of DHH or 5,6-dihydroxy-2-oxohex-3-enal, whereas the compounds C 12 H 14 O 7 (20.23 min) and C 12 H 12 O 6 (16.71 min) were formed from C 12 H 16 O 8 (18.23 min) by losing 1 and 2 moles of water, respectively. The compound C 12 H 10 O 5 should be a dimer of HMF formed by etherification . In contrast, the H/O atom ratios of C 10 H 18 O 6 (15.31 min), C 8 H 18 O 3 (20.76 min), C 10 H 12 O 4 (22.58 min), and C 12 H 26 O 4 (26.54 min) were not equal to 2, indicating that butanediol may participate in the formation of these compounds .…”

Section: Resultsmentioning

confidence: 94%

Conversion of Cellulose into 5-Hydroxymethylfurfural in a Biphasic System Catalyzed by Aluminum Sulfate and Byproduct Characterization

Shi

Zhu

Qin

et al. 2022

ACS Sustainable Chem. Eng.

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The production of 5-hydroxymethylfurfural (HMF) from cellulose is a crucial step in the production of high-value chemicals and fuels from renewable cellulosic biomass. In this study, the influences of the H2O/organic solvent ratio, the type of organic solvents, the addition of NaCl, and the type and concentration of catalysts on the catalytic conversion of cellulose into HMF in biphasic systems were comprehensively studied, and the highest HMF yield of 45.7% was obtained from cellulose in the H2O–tetrahydrofuran (THF) biphasic system with Al2(SO4)3 as the catalyst. Further investigation reveals that the excellent performance of the H2O–THF–Al2(SO4)3 reaction system was ascribed to the high V org/V aque (60/1), high C[Al2(SO4)3]aque (0.38 g/mL), and low C[Al2(SO4)3]org (10–4 g/mL) of the reaction system. Moreover, the byproduct formed during the conversion of cellulose in the H2O–THF–Al2(SO4)3 reaction system was characterized by liquid chromatography–mass spectrometry (LC–MS) and LC–MS2 to detect considerable initial polymers. One plausible mechanism of glucose conversion in the H2O–THF biphasic system was proposed based on the detected compounds.

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Section: Resultsmentioning

confidence: 94%

Conversion of Cellulose into 5-Hydroxymethylfurfural in a Biphasic System Catalyzed by Aluminum Sulfate and Byproduct Characterization

Shi

Zhu

Qin

et al. 2022

ACS Sustainable Chem. Eng.

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“…The choice of etherification agent is usually determined by the targeted product specifications. For example, the self-etherification of 5-HMF in the presence of a solid Brønsted acid, like H-ZSM-5, yields 5,5′-OBMF (Figure a) . This compound is useful as a precursor for imine-based polymers as well as an antiviral agent against hepatitis.…”

Section: Protection Strategiesmentioning

confidence: 99%

“…For example, the self-etherification of 5-HMF in the presence of a solid Brønsted acid, like H-ZSM-5, yields 5,5′-OBMF (Figure 7a). 58 This compound is useful as a precursor for imine-based polymers as well as an antiviral agent against hepatitis. Yields up to 90% have been reported, and the conversion correlates with the concentration of Brønsted acid sites.…”

Section: ■ Protection Strategiesmentioning

confidence: 99%

Protection Strategies for the Conversion of Biobased Furanics to Chemical Building Blocks

Coumans

Overchenko

Wiesfeld

et al. 2022

ACS Sustainable Chem. Eng.

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In recent years, the urgency to replace fossil-based resources by renewable biomass for obtaining chemical building blocks has only increased. Carbohydrate-derived furanic compounds are regarded as promising platforms for a renewable value chain. The high reactivity of such biobased intermediates requires the development of novel catalytic chemistry to enhance product yield. The protection of reactive functional groups provides a way to improve the product selectivity. Such protection strategies are common practice in the synthesis of fine chemicals and pharmaceuticals but are not fully explored for the conversion of furanic compounds. In this perspective, several examples of protection strategies focusing on the selective passivation of 5-HMF are discussed. Formation and removal of these protection groups are highlighted as well as the application of the neutralized 5-HMF in further processing. A guide for selecting the appropriate protection strategy depending on the targeted chemistry and operating conditions is provided.

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“…Although the introduction of mesoporous into the microporous zeolites by dual template method or post treatment method could improve the catalytic performance to a certain extent, the use of expensive templating agent and the severe mass loss of zeolites in post treatment process brought many questions such as catalyst economy, exhaust emission, and waste water treatment [5b,9] . Moreover, our previous work demonstrated that the strong acidity of zeolites could lead to the occurrence of side reactions (containing ring‐opening, hydrogenolysis, polymerization, etc) [8c,9b] . Amorphous silica‐aluminas (ASA), an exceptional type of porous materials, were also extensively used as solid acid catalysts and supports in the petrochemical industry [10] .…”

Section: Introductionmentioning

confidence: 99%

Efficient Etherification of 2,5‐Bis(hydroxymethyl)furan to 2,5‐Bis(propoxymethyl)furan by an Amorphous Silica‐Alumina Catalyst in a Fixed‐Bed Reactor

Chen

Xue

et al. 2022

ChemPlusChem

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The efficient etherification of 2,5‐bis(hydroxymethyl)furan (BHMF) to 2,5‐bis(propoxymethyl)furan (BPMF) was achieved by using low‐cost amorphous silica‐aluminas (ASA) catalysts in a fixed‐bed reactor. A considerable yield of BPMF up to 85.1 % was obtained over ASA‐30 catalyst under the reaction conditions of 140 °C, 2.0 MPa of N2, and 0.015 h−1 of WHSV. The excellent performance of ASA‐30 catalyst could be attributed to the relatively stronger acidity (>375 °C) and larger mesoporous size (6 nm), thereby facilitating the conversion of BHMF to BPMF. In addition, the lower ratio of Brønsted/Lewis acid sites for ASA catalyst was found to efficiently suppress the occurrence of side reactions.

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Catalytic self-etherification of 5-hydroxymethylfurfural to 5,5′(oxy-bis(methylene))bis-2-furfural over zeolite catalysts: effect of pore structure and acidity

Abstract: Understanding the role of pore structure and acidity of zeolite catalyst in the self-etherification of 5-hydroxymethylfurfural to 5,5′(oxy-bis(methylene))bis-2-furfural.

Cited by 16 publications

References 39 publications

Conversion of Cellulose into 5-Hydroxymethylfurfural in a Biphasic System Catalyzed by Aluminum Sulfate and Byproduct Characterization

Conversion of Cellulose into 5-Hydroxymethylfurfural in a Biphasic System Catalyzed by Aluminum Sulfate and Byproduct Characterization

Protection Strategies for the Conversion of Biobased Furanics to Chemical Building Blocks

Efficient Etherification of 2,5‐Bis(hydroxymethyl)furan to 2,5‐Bis(propoxymethyl)furan by an Amorphous Silica‐Alumina Catalyst in a Fixed‐Bed Reactor

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