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Process for the epoxidation of olefins

A technology of olefins and hydrogen peroxide, applied in chemical recovery, organic chemistry, etc., can solve problems such as unresolved, catalyst poisoning, etc.

Active Publication Date: 2006-01-04
EVONIK OPERATIONS GMBH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

None of the known methods of recovering and recycling solvents address the problem of catalyst poisoning and do not address said problem

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1 (comparative embodiment)

[0084] Epoxidation was carried out continuously in a 300 ml tubular reactor filled with 3 mm diameter silica incorporating titano-silicate extrudates. The equipment also includes three liquid containers and corresponding pumps and liquid separation containers. Three liquid containers containing methanol, 60% by weight aqueous H 2 o 2 and propylene. Adjust 60% H with ammonia water 2 o 2 to pH4.5. The reaction temperature is controlled by means of an aqueous cooling liquid circulating in a cooling jacket, whereby the temperature of the cooling liquid is controlled by means of a thermostat. The absolute reactor pressure was 25 bar. The mass flow rate of the feed pump was adjusted so that the propylene feed concentration was 21.5% by weight, the methanol feed concentration was 57% by weight, and H 2 o 2 The feed concentration was 9.4% by weight. The reactor operates in downflow mode. The temperature of the c...

Embodiment 2

[0090] Repeat Example 1, the only difference is: at a rate of 81 g / h, 10% by weight acetic acid methanol solution is added to the reflux stream of the methanol distillation column. The methanol stream withdrawn overhead contained more than 98% by weight of methanol, 1.6% by weight of water, 33 wppm of total nitrogen and 3 wppm of nitrogen from ammonia. From the difference between total nitrogen and ammonia nitrogen, the nitrogen content derived from organic nitrogen compounds was calculated to be 26 wppm. As in Example 1, the recovered methanol was reused for the epoxidation of propylene, and the results are shown in Table 1.

Embodiment 3

[0092] Repeat Example 1 with the only difference that: 10% by weight aqueous acetic acid solution is added to the reflux stream of the methanol distillation column at a rate of 98 g / h. The methanol stream withdrawn overhead contained more than 97 wt% methanol, 2 wt% water, 14 wppm total nitrogen and less than 4 wppm nitrogen from ammonia. From the difference between total nitrogen and ammonia nitrogen, the nitrogen content from organic nitrogen compounds was calculated to be between 10 and 14 wppm. As in Example 1, the recovered methanol was reused for the epoxidation of propylene, and the results are shown in Table 1.

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Abstract

The present invention refers to a process for the catalytic epoxidation of olefins in the presence of a titanium containing zeolite catalyst and a polar solvent whereby the deactivation of the catalyst upon recycling of the solvent has been considerably reduced. In the process one or more nitrogen containing compounds are introduced at some stage, a solvent stream is recovered, treated to contain less than 50 wppm nitrogen in the form of organic nitrogen compounds and at least a part of it is recycled to the epoxidation step. The invention is also directed towards a process for the catalytic epoxidation of propene which integrates the inventive treatment and recycle of the solvent into the workup of the reaction mixture.

Description

technical field [0001] The present invention relates to an improved process for the epoxidation of olefins using a titanium-containing zeolite catalyst whereby deactivation of the catalyst during solvent recycling is substantially reduced. Background technique [0002] It is known from EP-A 100 118 that olefins can be converted to epoxides with hydrogen peroxide when titanium-containing zeolites are used as catalysts. The reaction is preferably carried out in the presence of a polar solvent which can dissolve the olefin and hydrogen peroxide in the reaction mixture. Preference is given to using methanol as solvent. [0003] Nitrogen-containing compounds are frequently introduced into the process as raw material components, as additives for the epoxidation reaction or as additives or auxiliaries when working up the reaction mixture. [0004] Nitrogen-containing compounds can be introduced together with the hydrogen peroxide used. Commercially available hydrogen peroxide so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/12
CPCC07D301/12Y02P20/584
Inventor 托马斯·哈斯威利·霍芬沃尔夫冈·韦尔克劳迪娅·布拉塞吉多·施托赫尼奥尔诺贝特·乌尔里希
Owner EVONIK OPERATIONS GMBH
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