DEGUSSA epoxidation processes

Table 6.3 Catalytic performance in propene epoxidation with H P in the Degussa/Uhde process [20].

Thirty years after the invention of ENI s TS-1, new environmentally friendly processes have been commercialized for the epoxidation of propylene and the ammoximation of cyclohexanone that have no major by-products or coproducts. The BASF-Dow and Degussa-Uhde processes claim to be environmentally friendly, have low capital investment costs, and have no significant quantities of by-products when compared to either the chlorohydrin or the PO with styrene monomer processes. The Sumitomo PO process is also beneficial for the environment, because it needs only a cumene-to-cumene hydroperoxide reactivation process step. 

Researchers at Degussa AG focused on an alternative means towards commercial application of the Julia-Colonna epoxidation [41]. Successful development was based on design of a continuous process in a chemzyme membrane reactor (CMR reactor). In this the epoxide and unconverted chalcone and oxidation reagent pass through the membrane whereas the polymer-enlarged organocatalyst is retained in the reactor by means of a nanofiltration membrane. The equipment used for this type of continuous epoxidation reaction is shown in Scheme 14.5 [41]. The chemzyme membrane reactor is based on the same continuous process concept as the efficient enzyme membrane reactor, which is already used for enzymatic a-amino acid resolution on an industrial scale at a production level of hundreds of tons per year [42]. 

Degussa, in turn, has recently announced the commercialization of a HPPO process, jointly developed with the engineering company Uhde. Parallel to this, Degussa with Headwaters is also working on the direct synthesis of H2O2, for which a demonstration plant was completed in 2006 [151]. According to the news release, hydrogen peroxide will be obtained in the new process as a dilute methanol solution to be used directly in the epoxidation of propene. 

The use of perpropionic add as an epoxidation agent for propylene has been proposed by BayeriDegussa, Interox (Carbochimique, laporte, Sofray) and Ugine Kuhlmann. The perpropionic add is produced by the oxidation of propionic add with hydrogen peroxide, in the presence of sulfuric acid. The propylene is epoxidized between 05 and 1.4.106 Pa absolute, at about 60 to 80°C, in the Bayer/Degussa process, which operates in the presence of benzene, and at 100°C in the Interox process, which uses 12-dichloropropane as a solvent. 

G. Thiele, Process for the Preparation of Epoxides from Olefins, Vol. US Patent 6,372,924 B2, To Degussa-Huls AG. 

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