Efficient Hydrolysis of Cyclohexyl Acetate to Cyclohexanol Catalyzed by Dual-SO₃H-Functionalized Heteropolyacid-Based Solid Acids

Abstract

We report here novel dual-SO 3 H-functionalized heteropolyacid-based solid acids (HPA-ILs) with different Keggin heteropolyacid anions and investigate their catalytic applications in hydrolysis of cyclohexyl acetate to cyclohexanol. Compared with a variety of the traditional acidic catalysts, [Bis-Bs-BDMAEE]HPMo 12 O 40 displayed the higher catalytic acidities and good repeated utilization. The effects of various parameters including reaction temperatures, catalysts dosage, initial reactants volume ratio, and reaction time on the hydrolysis of cyclohexyl acetate were studied in detail. The optimal condition was obtained, and the cyclohexyl acetate conversion reached up to 90.56% with 94.86% selectivity for cyclohexanol. More interestingly, the reusability of [Bis-Bs-BDMAEE]HPMo 12 O 40 was good because it was reused five times without a significant loss in catalytic activity.

Heteropoly Ionic Liquid Functionalized MOF-Fe: Synthesis, Characterization, and Catalytic Application in Selective Acetalization of Glycerol to Solketal as a Fuel Additive at Room Temperature, Solvent-Free Conditions

“…ILs-HPAs have been used in various applications such as electrochemistry, nanotechnology, and catalysis . They have also been used in various organic reactions, such as trans-esterification, desulfurization, hydrolysis, benzyl alcohol oxidation, synthesis of cyclic carbonate, synthesis of benzaldehyde glycol acetal, acetalization of glycerol, etc. Despite the characteristics mentioned of ILs-HPAs as homogeneous catalysts, they pose some complications, including high viscosity, which affects activity, and a homogeneity nature, which leads to difficulty in the recovery of the catalyst from the reaction mixture. , Recently, the design of heterogeneous catalysts has been explored to tackle the limitations of ILs.…”

Mild and highly selective hydrogenation of cyclohexyl acetate to cyclohexanol over Cu(i) coordinated amino-functionalized poly(ionic liquid)s

“…6,7 Alternatively, a novel two-step process (Scheme 1) involving cyclohexene esterification with acetic acid to cyclohexyl acetate (CHA) and subsequent hydrogenation of CHA has been developed for efficient production of CHOL in recent years. [8][9][10][11] The process has the advantages of low cost and environmental friendliness, in addition to alleviating overcapacity of acetic acid and cyclohexene.…”

Honeycomb-structured solid acid catalysts fabricated via the swelling-induced self-assembly of acidic poly(ionic liquid)s for highly efficient hydrolysis reactions

“…Cyclohexanol is a very important intermediate for the synthesis of adipic acid, hexamethylenediamine, cyclohexanone, and ε-caprolactam, and has been widely used in the coatings, surfactants, and textile industries [29]. The efficient production of cyclohexanol has attracted the attention of many researchers.…”

“…The efficient production of cyclohexanol has attracted the attention of many researchers. Three main cyclohexanol synthesis methods have been developed, namely phenol hydrogenation, cyclohexane oxidation, and cyclohexene hydration [29,30]. Phenol hydrogenation is disadvantageous owing to the high price of phenol, the feedstock.…”