Catalytic Synthesis of Carbonated Soybean Oil

Abstract

Carbonated soybean oil (CSBO) can be used as intermediate for the synthesis of non-isocyanate polyurethanes (NIPUs). In this work, CSBO was prepared by the reaction of epoxidized soybean oil (ESBO) with carbon dioxide (CO 2 ) using a novel composite catalyst comprising SnCl 4 Á 5H 2 O and tetrabutylammonium bromide (TBABr). The evolution of the reaction process and structure of CSBO were studied by means of IR, 1 H-NMR, and GPC techniques. Effects of catalyst formulation and various reaction conditions on the reaction were examined. The results showed that the obvious improvement in ESBO conversion using the present composite catalyst under mild conditions was achieved. Moreover, it was interesting to note that very high purity of CSBO was not a prerequisite for the synthesis of NIPUs with good performance.

Cyclic Carbonates Based on Vegetable Oils

“…The main part of researches is devoted to epoxidized soybean oil (ESBO) carbonation [6][7][8][9][10][11][12], in some works the epoxidized linseed oil (ELSO) [5,13] is used. Such choice is defined by the availability of these oils which are large-capacity products [14], they are widely applied at halogenated polymers processing (for example, polyvinylchloride).…”

“…Despite the wide range of catalysts, applied to obtain CC [1,2,4], catalytic systems on the basis of tetrabutylammonium bromide (TBAB) have become widely applied for CCVO synthesis [5][6][7][9][10][11][12][13]15], they are a large-capacity industrial product. The optimum of TBAB dosage is 2÷7 mol %, as relating to epoxy groups of a substrate.…”

“…The optimum of TBAB dosage is 2÷7 mol %, as relating to epoxy groups of a substrate. Besides individual TBAB, two-component systems with its application are also described: {ТTBAB + SnCl 4 } [10] and {TBAB + H 2 O} [9]. At the same time such catalytic systems as: sodium iodide, lithium bromide and potassium, benzyltrimethylammonium bromide, ion exchange resins Amberlite IRA-400 (Cl) are [6] of little effect [11], due to their low or full insolubility in the substratum.…”

“…From the point of view of time spent on the reaction, the performing of the process at the increased pressure seems more perspective, that is shown by a number of authors [7,10,13,15]. The first data about the influence of pressure upon EVO carbonation were submitted by Javni [7].…”

“…However, researchers have no consensus about the optimum pressure at CCVO synthesis. So, for example, Li gives data that pressure growth higher than 1.5 MPa does not give a positive result [10].…”