Oxidative Carboxylation of 1-Decene to 1,2-Decylene Carbonate

Abstract

Cyclic carbonates are valuable chemicals for the chemical industry and thus, their efficient synthesis is essential. Commonly, cyclic carbonates are synthesised in a two-step process involving the epoxidation of an alkene and a subsequent carboxylation to the cyclic carbonate. To couple both steps into a direct oxidative carboxylation reaction would be desired from an economical view point since additional work-up procedures can be avoided. Furthermore, the efficient sequestration of CO 2 , a major greenhouse gas, would also be highly desirable. In this work, the oxidative carboxylation of 1-decene is investigated using supported gold catalysts for the epoxidation step and tetrabutylammonium bromide in combination with zinc bromide for the cycloaddition of carbon dioxide in the second step. The compatibility of the catalysts for both steps is explored and a detailed study of catalyst deactivation using X-ray photoelectron spectroscopy and scanning electron microscopy is reported. Promising selectivity of the 1,2-decylene carbonate is observed using a one-pot two-step approach.

Oxidative carboxylation of olefins with CO2: environmentally benign access to five-membered cyclic carbonates

“…In 2018, Hutchings and co-workers described a one-pot, twostep sequential reaction for the synthesis of 1,2-decylene carbonate. 50 The strategy consisted of the epoxidation of 1decene in the presence of SiO 2 -supported gold catalyst under an air atmosphere and cycloaddition of CO 2 (20 atm) with the formed epoxide using TBAB and ZnBr 2 . The single-step version of this reaction was also investigated.…”

Oxidation of cycloalkene using supported ruthenium catalysts under solvent-free conditions

“…The characteristics of the support frequently influence catalyst activity. A marked support effect on conversion as well as selectivity has been demonstrated by earlier work on oxidation reaction [16].…”

“…Active component leaching in the solution is a fundamental difficulty associated with heterogeneous catalysts, especially in the liquid phase. In our previous study [16], supported cobalt catalysts have been used for epoxidation of alkene under the same reaction conditions reported in this work. the ICP AES analysis for this previous work showed that the materials were indeed leaching active components into the reaction mixture.…”

Ruthenium Catalyst for Epoxidation Reaction

“…High epoxide selectivity continues to pose difficulties in the context of the epoxidation reaction. This has led to the identification and quantification of several additional by-products, which have been comprehensively detailed in earlier studies Ruthenium Catalyst for Epoxidation Reaction DOI: http://dx.doi.org/10.5772/intechopen.96466 [15,16]. When the reaction runs for 24 hours, it results in the formation of substantial amounts of allylic products.…”