Oxidation of cycloalkanes catalysed by N-hydroxyimides in supercritical carbon dioxide

Abstract

This paper reports cyclopentane, cyclohexane and cyclooctane oxidation in the presence of N-hydroxyphthalimide or 4-dodecyloxycarbonyl-N-hydroxyphthalimide in combination with Co(II) and Fe(II) salts using O 2 /CO 2 mixture (0.5 MPa O 2 , 9.5 MPa CO 2 ). The studies demonstrated that the application of scCO 2 in cyclohexane and cyclooctane oxidation processes results in higher conversion and yield of respective ketone and alcohol in comparison to processes performed using air under pressure (0.7 MPa).Publisher's Note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

N-Hydroxyphthalimide Supported on Silica Coated with Ionic Liquids Containing CoCl2 (SCILLs) as New Catalytic System for Solvent-Free Ethylbenzene Oxidation

“…Because of its poor solubility in hydrocarbons, the processes are usually carried out in polar solvents, e.g., in acetic acid [7], acetonitrile [8], or benzonitrile [9]. The use of compressed CO 2 [10][11][12] and ionic liquids [11,[13][14][15][16][17][18] has also been reported. In order to use NHPI in industrial processes, it is necessary to develop efficient methods of its recovery and reuse.…”

“…In order to use NHPI in industrial processes, it is necessary to develop efficient methods of its recovery and reuse. NHPI separation by evaporation of organic solvent [8,19] or CO 2 has been described in literature [10,11]. However, this simple method may prove to be ineffective, if the product of the reaction will be characterized by high polarity and related good solubility of NHPI.…”

Organocatalysis Meets Hydrocarbon Oxyfunctionalization: the Role of N‐Hydroxyimides

“…Lisicki et al studied the catalytic performance of a 4dodecyloxycarbonyl-NHPI (NHPIÀ C 12 ) heterogeneous system in supercritical carbon dioxide (scCO 2 ) towards the oxidation of cycloalkanes, with Fe(II) and Co(II) salts. [69] The nontoxic and noncorrosive intrinsic nature of scCO 2 allows its use as a promising alternative solvent. Additionally, the possibility of its easy separation from a post-reaction mixture is also a clear advantage.…”

New Evidence for the Key Role of Hydrogen Bonding Between N‐Hydroxyphthalimide and Halide Ionic Liquids in Hydrocarbons Oxidation

“…The main disadvantage of using NHPI as a catalyst for the oxidation of hydrocarbons is its poor solubility in non‐polar media, which requires the use of polar organic solvents, e. g., acetonitrile, benzonitrile, or acetic acid [7–9] . In recent years, ionic liquids [10–13] or supercritical CO 2 (scCO 2 ) [14,15] have also been used as solvents. Although they simplify the separation of the reaction mixture and can be recycled, ionic liquids are expensive.…”