Process for the epoxidation of olefins

A technology of epoxidation reaction and olefin, applied in the direction of organic chemistry, etc., can solve the problems that the long-term activity and selectivity data of the catalyst cannot be obtained, and the data has not been reached.

Active Publication Date: 2005-10-19
EVONIK OPERATIONS GMBH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After 2 hours the reaction is complete, even though 85% conversion has not yet been reached
Although experimental data show an increased reaction rate compared to compounds with aminocarbonyl functionality but no hydrogen atom attached to the nitrogen atom, the long-term activity and selectivity of this catalyst in a continuous process cannot be obtained from the information available from WO 01 / 92242 sex data

Method used

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  • Process for the epoxidation of olefins
  • Process for the epoxidation of olefins
  • Process for the epoxidation of olefins

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Example 1: Preparation of aqueous hydrogen peroxide solution used in the method of the present invention

[0107] In the test equipment of the loop method, according to the anthraquinone method for the preparation of hydrogen peroxide including hydrogenation, oxidation, extraction, drying and regeneration steps, it is used to include 75% by volume of C 9 / C 10The solvent mixture of alkyl-substituted aryl compound and 25% by volume of tris(2-ethylhexyl) phosphate includes 0.11mol / l 2-ethylanthraquinone and 0.29mol / l 2-ethyltetrahydro A working solution of anthraquinone, 0.13mol / l 2-isohexylanthraquinone and 0.12mol / l 2-isohexyltetrahydroanthraquinone. In the hydrogenation step, the loop reactor was operated at a hydrogen pressure of 0.35 MPa and a temperature of 58°C. Palladium black (0.5:1 g / l) was used as the hydrogenation catalyst. The hydrogen peroxide equivalent during hydrogenation is 13.0 g / l.

[0108] After hydrogenation, activated alumina is used to regenerate a por...

Embodiment 2-6 and comparative example 1-8

[0111] Titanium-silicate catalysts were used in all examples. Using silica sol as a binder, the titanium-silicate powder was molded into a 2 mm extrudate according to Example 5 in EP 00 106 671.1. Use the H of Example 1 concentrated to 60% by weight by evaporating water 2 O 2 Solution.

[0112] Epoxidation was continuously performed in a reaction tube with a volume of 300 ml, a diameter of 10 mm, and a length of 4 m. And the equipment also includes three liquid containers and related pumps as well as a liquid separation container. These three liquid containers are filled with methanol, 60% H 2 O 2 And acrylic. The reaction temperature is controlled by an aqueous cooling liquid circulating in the cooling jacket, wherein the temperature of the cooling liquid is controlled by a thermostat. The reactor pressure is 25 bar absolute. Adjust the mass flow of the feed pump so that the propylene concentration is 38% by weight, the methanol feed concentration is 48.7% by weight, and H 2 O 2 ...

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Abstract

The present invention refers to a continuos process for the epoxidation of olefins with hydrogen peroxide in presence of a heterogeneous catalyst promoting the epoxidation reaction, whereby the aqueous reaction mixture comprises: i) an olefin; ii) hydrogen peroxide; iii) less than 100 wppm of alkali metals, earth alkali metals, both irrespective whether in ionic, complex or covalently bonded form, bases or cations of bases having a pkB of less than 4.5, or combinations thereof; and iv) at least 100 wppm of bases or cations of bases having a pkB of at least 4.5 or combinations thereof, whereby the wppm are based on the total weight of hydrogen peroxide in the reaction mixture.

Description

Technical field [0001] The present invention relates to an improved method for continuous epoxidation of olefins, which uses a heterogeneous catalyst to promote the epoxidation reaction, thereby greatly reducing the deactivation of the catalyst. Background technique [0002] It is known from EP-A 100 119 that if titanium-containing zeolite is used as a catalyst, propylene can be converted into propylene oxide by hydrogen peroxide. [0003] Unreacted hydrogen peroxide cannot be economically recovered from the epoxidation reaction mixture. Moreover, unreacted hydrogen peroxide brings additional workload and expense to the processing of the reaction mixture. Therefore, it is preferable to use excess propylene to epoxidize propylene to achieve high hydrogen peroxide conversion. In order to obtain a high hydrogen peroxide conversion rate, it is advantageous to use a continuous flow reaction system. And for industrial-scale processes, high selectivity to the requir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/12
CPCC07D301/12
Inventor 克劳迪娅·布拉塞托马斯·哈斯威利·霍芬吉多·施托赫尼奥格奥尔格·蒂勒沃尔夫冈·韦尔
Owner EVONIK OPERATIONS GMBH
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