Efficient method of cyclic imides synthesis under ozone influence by the example of ε‐caprolactam oxidation reaction

Алексеева, О. В.; Konstantinova, M. L.; Rasumovskii, Stanislav

doi:10.1002/hc.20492

Cited by 10 publications

(5 citation statements)

References 18 publications

(10 reference statements)

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“…Ozonolysis of isomeric methylcyclohexanones mainly yields lactones and acids: monocarboxylic, dicarboxylic, and keto carboxylic. Alekseeva et al reported fast reaction of ozone with CL in carbon tetrachloride solvent to synthesize a single product of the reaction, azepane‐2,7‐dione. However, this product was not identified in the present study probably due to its further transformation in aqueous medium.…”

Section: Resultsmentioning

confidence: 99%

Treatment of Recalcitrant Caprolactam Wastewater Using Electrooxidation and Ozonation

Neti

Kashyap

2013

CLEAN Soil Air Water

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Advanced oxidation processes (AOPs) for the degradation of recalcitrant wastewater are of interest due to field application potential. We attempted the treatment of caprolactam (CL) wastewater which is highly acidic (pH 3.1) with low biodegradability index, using AOPs viz. electrochemical oxidation (EO) and ozonation. EO experiments under recirculation batch mode (20 mL min−1) in a three‐dimensional carbon bed reactor confirmed 18% chemical oxygen demand (COD) reduction. The first order rate constant for the EO of CL wastewater was estimated as 1.38 ± 0.15 × 10−2 min−1. The apparent Faradic efficiency and specific energy consumption were found to be 9.4% and 2.75 kWh kg−1 COD, respectively. Similarly, 27% COD and 26% total organic carbon were removed during 4‐h ozonation. Various organic compounds present in the raw and ozone treated effluent have been identified using GC‐MS; while many degraded partially, CL persisted even in 10‐h reacted samples. Both EO and ozonation methods are insufficient for the degradation of highly non‐biodegradable complex wastewater.

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Section: Resultsmentioning

confidence: 99%

Treatment of Recalcitrant Caprolactam Wastewater Using Electrooxidation and Ozonation

Neti

Kashyap

2013

CLEAN Soil Air Water

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“…Imides 9-12 were prepared by treatment of the corresponding dicarboxylic acids with ammonia; specifically, 9 was prepared by treatment of 2-methylglutaric acid with aqueous ammonia followed by evaporation to dryness and distillation [11], 10 was formed by reaction of 3-methylglutaric acid with thionyl chloride then aqueous ammonia followed by evaporation to dryness and distillation [12], 11 was prepared by reaction of 2,2-dimethylglutaric acid with urea at 160 • C [13], and 12 was prepared by treating diglycolic acid with aqueous ammonia followed by evaporation to dryness and distillation [14]. Imide 13 was prepared by treatment of ε-caprolactam with ozone in CCl 4 [15].…”

Section: Synthesis Of Imides 1-13mentioning

confidence: 99%

Solid State Structure and Hydrogen Bonding of Some Cyclic NH Carboximides

et al. 2023

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Thirteen new crystal structures of cyclic NH carboximides have been determined and are compared with respect to the mode of intermolecular hydrogen bonding observed in the crystal. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels–Alder reactions of maleimide, three methylated glutarimides, a morpholinedione and adipimide, the first seven-membered ring NH carboximide to be structurally characterised. Overall, seven of the compounds adopt a ribbon structure, five show centrosymmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.

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“…Pyrrolidones and caprolactams have been oxidized to their respective succinimides and adipimides in good synthetic yields using dimethyldioxirane (443), ozone (444), Dess-Martin periodane (445) and peracetic acid with catalytic manganese dichloride and microwave irradiation (five minutes) (446).…”

Section: Oxidation Of Pyrrolidones and Caprolactamsmentioning

confidence: 99%

Introduction to Pyrrolidone and Caprolactam Chemistry

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

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Pyrrolidones and caprolactams are important structural components of solvents, surfactants, polymers, natural products, and pharmaceuticals. This chapter provides an introduction to the structure, conformation, physical properties and reactivity of pyrrolidones and caprolactams. It begins with an overview of the nomenclature of lactams since there are several systems of nomenclature in practice, plus common names and various syncretisms. Next, the structures of pyrrolidone and caprolactam are discussed, starting with the X-ray crystal structures of pyrrolidone, N-methylpyrrolidone (NMP) and caprolactam. The conformational flexibility and ring strain of the two ring systems are also covered.Physical properties, such as dipole moments, the enthalpies of formation, vaporization and fusion, boiling points and melting points, are described. An attempt is made to put the properties of pyrrolidones and caprolactams into context with those of other lactams, amides and even lactones and cyclic ketones. Brønsted and Lewis basicity, acidity, hydrogen bonding and solubility are covered.Finally, a brief description of the basic reactivity of pyrrolidones and caprolactams is given. Topics covered are N-, O-, and α-C-alkylation, hydrolysis, reactions with organometallics, reduction, oxidation, and ring-opening polymerization. The intent is to give a concise physical organic perspective on reactivity (and stability) more than an extended treatise on synthetic elaborations. Definition and Nomenclature of LactamsLactams are cyclic amides in which both the carbonyl carbon and nitrogen atom of the amide group are part of a ring. The name, lactam, is a portmanteau of lactone (cyclic ester) and amide.Nomenclature of lactams follows a variety of conventions (Figure 1 and Table 1). The International Union of Pure and Applied Chemistry (IUPAC) recommends naming lactams as heterocyclic pseudoketones (IUPAC method 1) or by substituting lactam for the

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Efficient method of cyclic imides synthesis under ozone influence by the example of ε‐caprolactam oxidation reaction

Cited by 10 publications

References 18 publications

Treatment of Recalcitrant Caprolactam Wastewater Using Electrooxidation and Ozonation

Treatment of Recalcitrant Caprolactam Wastewater Using Electrooxidation and Ozonation

Solid State Structure and Hydrogen Bonding of Some Cyclic NH Carboximides

Introduction to Pyrrolidone and Caprolactam Chemistry

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