High-yield and high-efficiency conversion of cyclohexanone oxime to ε-caprolactam in a green and facile reaction process over deep eutectic solvents

Sun, Shiqin; Liu, Shiwei; Fang, Yu; Zhang, Jian; Xing, Weiguo; Yu, Shitao

doi:10.1016/j.ces.2022.117519

Cited by 8 publications

(2 citation statements)

References 52 publications

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“…Based on the reaction mechanism, the kinetics of the CHO conversion to CPL are further studied in this work. Figure 8a shows the effect of CPL yield on different times without considering the influence of by-products, and the yield of CPL have no change within the 2 h. Therefore, it has been confirmed that a pseudo-first-order reaction is applied to the catalytic conversion of CHO to CPL by Equation ( 5) [6,[51][52][53]. The yield of CPL significantly increases within the 2 h, indicating that high activation energy is required during this time.…”

Section: Characterization Of the Synthesized [Cpl][xmsa]mentioning

confidence: 76%

Novel Brønsted Acidic Ionic Liquids as High Efficiency Catalysts for Liquid-Phase Beckmann Rearrangement

et al. 2023

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Exploring environmentally friendly, efficient, cheap and recyclable catalysts are essential for the development of green, sustainable and mild processes for the liquid-phase Beckmann rearrangement. Herein, a novel caprolactam-based Brønsted acidic ionic liquid ([CPL][2MSA]) was developed for the conversion of cyclohexanone oxime (CHO) to caprolactam (CPL), not only as a catalyst, but also as a mild reaction medium. Under the reaction conditions for the reaction temperature (90 °C), reaction time (2 h) and mole ratio ([CPL][2MSA]: CHO = 3:1), [CPL][2MSA] possesses plenty of high sulfonate groups, which exhibit high conversion (100%) and selectivity (95%) without any other co-catalysts or metals. Based on the thermogravimetric (TGA) and differential scanning calorimetry (DSC) analyses, the decomposition and glass transition temperatures are gradually increased with the increase in MSA mole content, revealing the existence of hydrogen-bonded clusters. Interestingly, the occurrent route of the liquid-phase Beckmann rearrangement for CHO in [CPL][2MSA] is revealed by in situ FT-Raman. In addition, the dominating H-bond combination between CHO and [CPL][2MSA] is further confirmed by COSMO-RS model. The activation energy (Ea) of the reaction is calculated by the first-order reaction kinetics. Thus, the [CPL][2MSA] with plenty of acidic catalytic active species is an environmentally friendly and efficient candidate for the liquid-phase Beckmann rearrangement.

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Section: Characterization Of the Synthesized [Cpl][xmsa]mentioning

confidence: 76%

Novel Brønsted Acidic Ionic Liquids as High Efficiency Catalysts for Liquid-Phase Beckmann Rearrangement

et al. 2023

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“…Under certain conditions, the anionic ring-opening polymerization reaction proceeds at high conversion rates and with negligible wastes of matter. Beyond being green, this process has epsilon caprolactam as its reagent, which can be synthesized from renewable sources [21][22][23] and produces a polymer (PA-6) that can be returned to the starting monomer and is, therefore, recyclable.…”

Section: Anionic Polymerization Of Pa-6 From the Epsilon-caprolactam ...mentioning

confidence: 99%

Thermoplastic Composite Materials Approach for More Circular Components: From Monomer to In Situ Polymerization, a Review

et al. 2022

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To move toward eco-sustainable and circular composites, one of the most effective solutions is to create thermoplastic composites. The strong commitment of world organizations in the field of safeguarding the planet has directed the research of these materials toward production processes with a lower environmental impact and a strong propensity to recycle the polymeric part. Under its chemical properties, Nylon 6 is the polymer that best satisfies this specific trade-off. The most common production processes that use a thermosetting matrix are described. Subsequently, the work aimed at investigating the use of thermoplastics in the same processes to obtain comparable performances with the materials that are currently used. Particular attention was given to the in situ anionic polymerization process of Nylon 6, starting from the ε-caprolactam monomer. The dependencies of the process parameters, such as temperature, time, pressure, humidity, and concentration of initiators and activators, were therefore investigated with reference to the vacuum infusion technique, currently optimized only to produce thermosetting matrix composites, but promising for the realization of thermoplastic matrix composite; this is the reason why we chose to focus our attention on the vacuum infusion. Finally, three production processes of the polymeric matrix and glass fiber composites were compared in terms of carbon footprint and cumulative energy demand (CED) through life-cycle assessment (LCA).

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Rational construction of multiple hollow silicalite-1 zeolite with enhanced quasi acidity for robust vapor-phase Beckmann rearrangement

Zhang

Xia

et al. 2023

Nano Res.

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High-yield and high-efficiency conversion of cyclohexanone oxime to ε-caprolactam in a green and facile reaction process over deep eutectic solvents

Cited by 8 publications

References 52 publications

Novel Brønsted Acidic Ionic Liquids as High Efficiency Catalysts for Liquid-Phase Beckmann Rearrangement

Novel Brønsted Acidic Ionic Liquids as High Efficiency Catalysts for Liquid-Phase Beckmann Rearrangement

Thermoplastic Composite Materials Approach for More Circular Components: From Monomer to In Situ Polymerization, a Review

Rational construction of multiple hollow silicalite-1 zeolite with enhanced quasi acidity for robust vapor-phase Beckmann rearrangement

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