Process for preparing epoxy-compound by catalytic oxidation of alpha-olefin by metal porphyrin

Abstract

The invention relates to a method for preparing epoxy compounds by catalyzing the oxidation of alpha-olefins by metalloporphyrins. The steps are: in the presence of oxidant air or oxygen, dichloromethane or ethanol is used as a solvent, and a mononuclear metalloporphyrin or μ-oxo binuclear metalloporphyrin with a concentration of 1-50PPM is selected as a catalyst. ℃ and under normal pressure for 0.5-10 hours to catalyze the oxidation of α-olefins to generate epoxy compounds. The aforementioned α-olefins are C6-C18 α-olefins, preferably C11-C18 α-olefins. The catalyst is preferably mononuclear metalloporphyrin or μ-oxo binuclear metalloporphyrin whose metal atoms M1 and M2 are manganese, and the catalyst concentration is preferably 2-20PPM. The method has mild reaction conditions, high conversion rate of olefin, high selectivity of epoxy compound and high yield.

Description

technical field [0001] The invention relates to a method for preparing epoxy compounds by catalyzing the oxidation of alpha-olefins by metalloporphyrins. Background technique [0002] Olefin epoxidation products are a class of important organic raw materials and intermediates with a wide range of uses, and are widely used in petrochemical, fine chemical and organic synthesis fields. A series of chiral compounds with different structures can be prepared from epoxy compounds through functional group transformation reactions, and epoxidation reactions play an important role in organic synthesis. Environmentally friendly olefin epoxidation technology is a hotspot in the field of catalytic oxidation, and air or oxygen, as an ideal clean oxygen source, has been paid more and more attention by people. Because of this, the study of air or oxygen oxidation of alkenes to epoxides is of general significance. [0003] At present, except for ethylene oxide, most of the production metho...

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Problems solved by technology

The problems in this method include: (1) Although this method involves the oxidation of various olefins, the oxidation of olefins only involves two kinds of gaseous olefins, propylene and butene, in the examples, and it does not involve the relatively difficult and industrial olefin oxidation. C with higher application value 5 The above alkenes (liquid alkenes), especially not related to C 10 The epoxidation of the above α-olefins; (2) the product of this method to catalyze the oxidation of olefins is a mixture of enols, enones, epoxy compounds and other by-products, and only the total selectivity of the three main products is given , without giving the respective selectivities of the three main products and other by-products, among which the total selectivity of the three main products obtained from the oxidation of alkenes can only reach 88%

The type of other by-products is not specified, and the method for obtaining epoxy compounds from the separation and purification of the product is not provided, which will bring great difficulties to the follow-up treatment in future industrial applications; (3) in the method embodiment, the olefin conversion Efficiency is low, and wherein alkene propylene conversion rate is only 26%, and butene conversion rate is only 30.8%; (4) in the embodiment of this method except that NaClO is used as oxygenant oxidation α-pinene and is carried out under normal pressure, Utilize air or oxygen or the mixed gas oxidation of oxygen and other inert gas to oxidize other alkenes all need high pressure, especially oxidized alkenes need just could react under the high pressure of 8-10atm; (5) when this method adopts chemical oxidant to carry out oxidation reaction, its The composition of the solvent is complex, and the amount of chemical oxidant is large, the environmental pollution is serious, and the post-processing is difficult

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