Hydrolysis of Oligosaccharides and Polysaccharides on Sulfonated Solid Acid Catalysts: Relations between Adsorption Properties and Catalytic Activities

Abstract

Sulfonated solid acid materials, such as sulfonated carbon catalysts, are promising materials as heterogeneous catalysts for the hydrolysis of esters and polysaccharides in water solvents. The catalytic active site is a sulfonic acid functional group. Compared to conventional strong acidic ion-exchange resin catalysts, sulfonated carbon materials have less sulfonic acid functional groups but higher catalytic activity for hydrolysis of polysaccharides per catalyst weight. However, the details of catalytic properties and the substrate suitability of both catalysts are unclear. In this study, the hydrolytic activities and the adsorption properties of both catalysts were investigated for various oligosaccharides and polysaccharides with varying degrees of polymerization (DP). The catalytic activities for the hydrolysis with increase of the DP of saccharides were found to increase over the sulfonated carbon catalyst but decrease over strong acidic ion-exchange resin catalyst. The inverse catalytic properties attribute to the dependence of the amounts of adsorption and/or penetration of saccharides on the DP. Moreover, the catalytic activity per acidic sites of strong acidic ion-exchange resin is in good agreement with the value obtained by multiplying the catalytic activity of a dilute sulfuric acid by the penetration degrees.

Synthesis and characterization of novel hercynite@sulfuric acid and its catalytic applications in the synthesis of polyhydroquinolines and 2,3-dihydroquinazolin-4(1H)-ones

“…24 Most solid state acids are heterogenized organic acids and transition metal complexes or acidic ion-exchange polymer resins. [33][34][35][36] Recently, various types of solid-acid catalysts, i.e. silica sulfuric acid (SSA), 37,38 boehmite silica sulfuric acid (boehmite-SSA) 39 and magnetic silica sulfuric acid (Fe 3 O 4 @-SSA), 40 have been developed using Zolgol's method.…”

Reactivity of metal–oxo clusters towards biomolecules: from discrete polyoxometalates to metal–organic frameworks

“…174 Since polysaccharides represent a major component of biomass, their breakdown into monosaccharides, such as glucose, is the first step in the conversion of biomass into renewable and sustainable fuels. 175,176 This is an important type of reactivity to address since the environmentally damaging effects of the overconsumption of fossil fuels have led to the exploration of sustainable alternatives, and the conversion of biomass is a particularly attractive option because it is the only renewable carbon reservoir for the production of fuels and chemicals. 177 However, commonly employed techniques for biomass valorization ( i.e.…”

“…Controlling the selectivity, rate, and efficiency of the hydrolysis reaction in the presence of mineral acids is very challenging, and the subsequent separation of the obtained products is difficult. 176,185,186 Moreover, corrosion of the reactor and high equipment cost associated with using mineral acids, together with waste disposal problems, represent major obstacles. 185 Additionally, such processes require very high pressures and temperatures (100–300 °C), which can result in side reactions and degradation of the obtained products.…”

“…185 Additionally, such processes require very high pressures and temperatures (100–300 °C), which can result in side reactions and degradation of the obtained products. 176,185,186 Enzymatic processes, on the other hand, are less harmful and operate under very mild reaction conditions, but the high cost of the currently used enzymes and their limited recyclability, stability, and substrate selectivity hinder their use in industry. 176,186 Therefore, there is a great need for developing more environmentally conscious and cost-effective biomass conversion catalysts that can operate under mild reaction conditions.…”

Multicomponent Bifunctionalization of Methyl Ketones Enabled by Heterogeneous Catalysis and Solar Photocatalysis in Water

“…Therefore, great effort has been devoted to developing aqueous phase reactions for organic synthesis. − In addition, as a renewable light energy, sunlight-induced photocatalytic reactions have become a green and simple strategy for organic transformation. − On the other hand, the development of multicomponent transformations has attracted extensive interest because they provide a greater impact with substantial minimization of waste, labor, time, and cost relative to linear syntheses. − Based on the urgent requirements of green synthesis and our research interests in developing green catalytic systems − and C–H functionalization reactions, − herein, we demonstrate a novel and green multicomponent transformation for the bifunctionalization of methyl ketones (Scheme b). In this transformation, ion-exchange resin Amberlyst 15 was used as the promising heterogeneous catalyst because of its recoverability and reusability. − In addition, quinoxalinones were selected as one of the reactants because they widely exist in natural products, functional materials, and pharmaceuticals. − In particular, 3-functionalized quinoxalinones are known for their superior chemical properties and outstanding biological activities, − such as anticancer and antimicrobial activities as well as insulin secretion stimulation activity (Figure…”