The solubilities of adipic acid in cyclohexanol + cyclohexanone mixtures from 303.0 to 353.0 K and in cyclohexanone + cyclohexane mixtures from 303.0 to 378.5 K were determined using a titration and an in situ ATR-FTIR method. The averaged relative deviation between two methods at given temperatures was less than 2%. The solubility of adipic acid in cyclohexanone + cyclohexane mixtures increases with increasing mass fraction of cyclohexanone in the mixtures at given temperatures. However, the solubility of adipic acid in cyclohexanol + cyclohexanone mixtures reaches the maximum at cyclohexanone mass fraction of 0.4. The experimental data were well correlated by Apelblat equation and λh equation. The thermodynamics functions of the dissolution process were calculated by van't Hoff equation.
A novel sulfonated bamboo-derived carbon (SBC) was prepared through a one-pot simultaneous carbonization and sulfonation method using ptoluenesulfonic acid as the sulfonating agent. This method was used in place of the two-step method of high temperature carbonization followed by sulfonation, in order to reduce energy consumption and avoid the use of substantial amounts of strong liquid acid. The as-prepared catalyst bearing SO3H, COOH, and phenolic OH groups demonstrated efficient catalytic activity in the dehydration of fructose to 5-hydroxymethylfurfural (HMF), achieving 92.1% HMF yield in a mixture of tetrahydrofuran (THF) and dimethylsulfoxiden (DMSO) (volume ratio of THF/DMSO 3/7). The mixture had a fructose concentration of 0.08 g·mL -1 with a catalyst amount of 10% weight of fructose at 140 °C in 60 min. No distinct activity drop was observed after the initial deactivation during 5 recycling runs, confirming a good stability of the prepared catalyst. Moreover, kinetic data showed that SBC promoted fructose dehydration to HMF may follow pseudo-first order kinetics with the activation energy of 43.6 kJ·mol -1 under investigated conditions. The convenient catalyst preparation method and excellent catalytic performance of the catalyst provide an easy-handling and ecofriendly strategy for crude biomass utilization in catalyst production.
Robust core–shell magnetic materials catalyse quantitatively the aerobic oxidation of a wide range of benzylic alcohols into corresponding aldehydes at room temperature showing excellent tolerance towards the substituents on the phenyl ring.
Cuprous halides, best described as (CuX)n (X = Cl−, Br−, and I−) in their solid state, catalyse selective aerobic oxidation of alcohols with the assistance of both NMI (N‐methylimidazole) and TEMPO (2,2,6,6‐tetramethylpiperidine‐1‐oxyl), and the iodide generally demonstrates the highest activity, for example, in the oxidation of 1‐octanol at ambient temperature under 24 h' reaction. However, in the aerobic oxidation of benzylic alcohols, the chloride showed superiority to the iodide in that the aerobic oxidation was quantitatively completed within 3 h at ambient temperature whereas the iodide showed only about half the activity of the chloride analogue. By probing the system using electrochemistry, electric conductivity, and 1H NMR titration, it was revealed that the surprising anomaly was due to the difference in the rate of forming active species, [Cu (NMI)2X(MeCN)], from the polymeric solid in a two‐stage process. Substrates expansion of 11 benzylic alcohols indicated that CuCl/NMI/TEMPO system demonstrated quantitative conversion of benzylic alcohols into corresponding aldehydes within 3 h and showed great tolerance to the substituents on the phenyl ring of the substrates. Furthermore, electron‐withdrawing substituent was beneficial to the oxidation and could offset the steric effect at orthro‐substituent. Such a behaviour suggested that in the catalysis, increasing the acidity of the hydroxyl group (OH) of the substrates could ease the oxidation, which implied that the deprotonation via an internal pathway might be one of the rate‐determining steps. Our results also showed that the anion halide participated actively in the catalysis by coordinating to Cu(I) in the active species.
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