Dataset Information

One-Pot Synthesis of 5-Hydroxymethylfurfural from Glucose by Bronsted Acid-Free Bifunctional Porous Coordination Polymers in Water.

ABSTRACT: Efficient synthesis of 5-hydroxymethylfurfural (HMF) using glucose (Glc) as a starting material represents an important process in biomass transformation. In this study, novel bifunctional porous coordination polymer (PCP) catalysts [PCP(Cr)-NH_2-x (CH₃) _x ; x = 0, 1, or 2] containing Lewis acidic and Lewis basic sites have been synthesized and utilized as solid-phase catalysts for HMF synthesis starting from a Glc-in-water system. PCP(Cr)-NH₂ was found as the optimal catalyst, with an HMF yield of 65.9% and Glc conversion of 99.9% in a water/tetrahydrofuran (THF) system. Compared with PCP(Cr), amino groups in PCP(Cr)-NH₂ catalysts play a vital role in Glc isomerization and subsequent dehydration-cyclization process to obtain the highly selective and effective fructose-to-HMF conversion. High yield and chemoselectivity are ascribed to concurrent extraction of HMF into the THF layer just upon its formation in water. The mechanism of Lewis acid-base synergistic catalysis was deduced by means of infrared spectroscopy, and catalysts could be reused after simple washing procedure with high reproducibility.

SUBMITTER: Liang F

PROVIDER: S-EPMC6648545 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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One-Pot Synthesis of 5-Hydroxymethylfurfural from Glucose by Brønsted Acid-Free Bifunctional Porous Coordination Polymers in Water.

Liang Fengbing F Chen Dawei D Liu Huizhou H Liu Weimin W Xian Mo M Feng Dexin D

ACS omega 20190528 5

Efficient synthesis of 5-hydroxymethylfurfural (HMF) using glucose (Glc) as a starting material represents an important process in biomass transformation. In this study, novel bifunctional porous coordination polymer (PCP) catalysts [PCP(Cr)-NH2-x (CH3) x ; x = 0, 1, or 2] containing Lewis acidic and Lewis basic sites have been synthesized and utilized as solid-phase catalysts for HMF synthesis starting from a Glc-in-water system. PCP(Cr)-NH< ...[more]

PMID: 31460021

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Project description:Although a widely used and important industrial gas, ammonia (NH3) is also highly toxic and presents a substantial health and environmental hazard. The development of new materials for the effective capture and removal of ammonia is thus of significant interest. The capture of ammonia at ppm-level concentrations relies on strong interactions between the adsorbent and the gas, as demonstrated in a number of zeolites and metal-organic frameworks with Lewis acidic open metal sites. However, these adsorbents typically exhibit diminished capacity for ammonia in the presence of moisture due to competitive adsorption of water and/or reduced structural stability. In an effort to overcome these challenges, we are investigating the performance of porous polymers functionalized with Brønsted acidic groups, which should possess inherent structural stability and enhanced reactivity towards ammonia in the presence of moisture. Herein, we report the syntheses of six different Brønsted acidic porous polymers exhibiting -NH3Cl, -CO2H, -SO3H, and -PO3H2 groups and featuring two different network structures with respect to interpenetration. We further report the low- and high-pressure NH3 uptake in these materials, as determined under dry and humid conditions using gas adsorption and breakthrough measurements. Under dry conditions, it is possible to achieve NH3 capacities as high as 2 mmol g-1 at 0.05 mbar (50 ppm) equilibrium pressure, while breakthrough saturation capacities of greater than 7 mmol g-1 are attainable under humid conditions. Chemical and structural variations deduced from these measurements also revealed an important interplay between acidic group spatial arrangement and NH3 uptake, in particular that interpenetration can promote strong adsorption even for weaker Brønsted acidic functionalities. In situ infrared spectroscopy provided further insights into the mechanism of NH3 adsorption, revealing a proton transfer between ammonia and acidic sites as well as strong hydrogen bonding interactions in the case of the weaker carboxylic acid-functionalized polymer. These findings highlight that an increase of acidity or porosity does not necessarily correspond directly to increased NH3 capacity and advocate for the development of more fine-tuned design principles for efficient NH3 capture under a range of concentrations and conditions.

Dataset Information

One-Pot Synthesis of 5-Hydroxymethylfurfural from Glucose by Bronsted Acid-Free Bifunctional Porous Coordination Polymers in Water.

Publications

One-Pot Synthesis of 5-Hydroxymethylfurfural from Glucose by Brønsted Acid-Free Bifunctional Porous Coordination Polymers in Water.

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