Abstract
Comparison of the methods of the phase transfer catalysis and hydroperoxide in the epoxidation of 1,5,9-cyclododecatriene The process of the epoxidation of cis, trans, trans-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) with the 30% aqueous hydrogen peroxide under the phase transfer conditions and with tert-butyl hydroperoxide under the homogeneous conditions was investigated. Onium salts such as Aliquat® 336, Arquad® 2HT, methyltrioctylammonium bromide and the Na2WO4/H3PO4 catalyst system are very active under the phase transfer catalysis (PTC) conditions for the selective epoxidation of cis, trans, trans-1,5,9-cyclododecatiene (PTC method). These catalytic systems were found to be as active and selective as the homogeneous phase system Mo(CO)6/TBHP (hydroperoxide method).
Highlights
Epoxides are useful industrial intermediates such as e.g. propylene oxide which is used at the root of the synthesis of polyether polyols used for the production of polyurethane foams, and used for the synthesis of propylene glycol for the elaboration of unsaturated polyester resins[1]
All experiments were performed with the following reagents: 46% of the TBHP solution in 1,2-dichloroethane (DCE), which was received in the extraction process of 70% TBHP water solution (Aldrich) by 1,2dichloroethane[9], an aqueous solutions of H2O2 (30%), phosphorous(V) acid (85%), and 1,2-dichloroethane were purchased from POCh, Poland; cis,trans,trans-1,5,9cyclododecatriene (CDT), methyltrioctylammonium chloride (Aliquat® 336), tetraethylammonium bromide, methyltrioctylammonium bromide, and dodecane were obtained from Aldrich; sodiumtungstate(VI), tetraethylammonium chloride, tetrapropylammonium bromide, tetrabutylammonium hydrogensulfate and dimethyl[dioctadecyl(76%) + dihexadecyl(24%)] ammonium chloride (Arquad® 2HT) were purchased from Fluka; tetrabutlammonium bromide and molybdenum hexacarbonyl, Mo(CO)[6] (>95%) were obtained from Merck-Schuchardt
The investigation of the influence of the type of the phase transfer catalyst on the CDT epoxidation were performed with the use of different ammonium salts (PTA): tetraethylammonium chloride, methyltrioctylammonium chloride (Aliquat® 336), dimethyl[dioctadecyl(76%) + dihexadecyl(24%)]ammonium chloride (Arquad® 2HT), tetrabutylammonium hydrogensulfate, tetraethylammonium bromide, tetrapropylammonium bromide, tetrabutlammonium bromide, and methyltrioctylammonium bromide
Summary
Epoxides are useful industrial intermediates such as e.g. propylene oxide which is used at the root of the synthesis of polyether polyols used for the production of polyurethane foams, and used for the synthesis of propylene glycol for the elaboration of unsaturated polyester resins[1]. Industrial production of epoxides usually employs a different oxygen source. Stringent environmental legislation as well as economic factors lead to a preference of the oxidations involving dioxygen, hydrogen peroxide, and alkyl hydroperoxides such as tert-butyl peroxide (TBHP)[1]. TBHP is probably one of the best oxygen sources because it is thermally stable, not very corrosive, relatively safe, and well soluble in a nonpolar solvent. The 1-phenylethanol obtained as a co-product from the ethylbenzene hydroperoxide reaction is dehydrated to produce styrene
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