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A method of continuously preparing 1,2-epoxycyclododecane

A technology of epoxy cyclododecane and cyclododecene, which is applied in the direction of organic chemistry, can solve the problems of difficult control of process conditions, unfavorable industrialization, and shortened half-life, and achieve high selectivity of main products, easy industrial scale-up, Realize the effect of industrial amplification

Active Publication Date: 2015-05-27
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method of increasing the amount of oxidant not only increases the cost of raw materials, but also the remaining TBHP is difficult to handle, which is uneconomical in technology
[0008] Second, it is difficult to control the process conditions
Therefore, although this method of adopting a lower reaction temperature can improve product selectivity, the reaction cycle is long, which is unfavorable to industrialization; but if the temperature is increased to shorten the production cycle, the half-life of TBHP will be shortened, and in the reaction process Part of TBHP decomposes, which requires increasing the amount of TBHP fed at the initial stage to increase production costs. At the same time, the oxygen generated by TBHP decomposition can oxidize olefins under catalyst and reaction conditions, resulting in increased by-products, decreased selectivity of main products, and difficulty in separation. increase
[0009] Third, the cases of TBHP epoxidation of cyclododecene reported in the literature are all batch processes, unless a large excess of TBHP is used, it is difficult to achieve high conversion and selectivity at the same time
[0010] The above problems have caused obstacles to the industrial promotion of utilizing TBHP to produce epoxycyclododecane

Method used

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  • A method of continuously preparing 1,2-epoxycyclododecane
  • A method of continuously preparing 1,2-epoxycyclododecane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～7

[0051] use figure 1 In the continuous tank reactor shown, where n=3, the reactor is connected in series with four tanks, and the volume of each tank is 1L. Cyclododecene is 0.616kg / h, and the amount of molybdenum acetylacetonate as catalyst is 0.1wt%, based on the weight of cyclododecene. The tert-butanol solution with a TBHP concentration of 50wt% is added according to the total feed amount shown in Table 1 and distributed through the C1-C3 feed inlets, with an average residence time of about 2 hours and a temperature of 110°C. Add cyclohexene 0.152kg / h from B port to the fourth kettle (cyclohexene: cyclododecene=1:2), the residence time is about 0.6h, and the temperature is 90°C. The discharge of discharge port D was analyzed, and the results are shown in Table 1.

[0052] Table 1 Embodiment 1~7 reaction condition and result

[0053]

Embodiment 8

[0055] use figure 1 In the continuous tank reactor shown, where n=10, the reactors are eleven tanks connected in series, and the volume of each tank is 1L. Cyclododecene 0.992kg / h, catalyst ammonium molybdate / ethylene glycol / water complex dosage 0.01wt%, based on the weight of cyclododecene. The total amount of tert-butanol solution with TBHP concentration of 80wt% is 0.807kg / h, according to k 1 ~ k 9 Both are 1 feed, that is, each feed port is fed with 10% of the total amount of TBHP. The 1st to 10th kettles were kept at a reaction temperature of 90°C, and the residence time was 5h. Add 0.490kg / h of cyclohexene to the 11th kettle from port B, and the residence time is about 0.4h. The eleventh kettle was kept at a temperature of 120°C. After the discharge from port D, it is analyzed by gas chromatography. The conversion rate of cyclododecene is 100%, the selectivity of epoxycyclododecane is 99.9%, the conversion rate of cyclohexene is 16%, and there is no remaining TBHP....

Embodiment 9

[0057] use figure 1 In the continuous tank reactor shown, where n=5, the reactor is a series of six tanks, each volume of the first to fifth tanks is 1L, and the volume of the sixth tank is 0.5L. Cyclododecene 0.673kg / h, catalyst molybdenum acetylacetonate dosage 1wt%, calculated by cyclododecene weight. TBHP concentration is 10wt% toluene solution adding total amount is 3.83kg / h, press k 1 ~ k 5Both are 2 feeds, that is, the ratio of each feed port is 51.6% for C1, 25.8% for C2, 12.9% for C3, 6.5% for C4, and 3.2% for C5. The first to fifth kettles were kept at a reaction temperature of 130°C and a residence time of 1h. Add 0.034kg / h of n-hexene to the sixth kettle from port B, and the residence time is about 0.1h. The temperature of the sixth kettle was maintained at 130°C. D mouth is discharged and analyzed by gas chromatography. The conversion rate of cyclododecene is 100%, the selectivity of epoxycyclododecane is 99.8%, the conversion rate of n-hexene is 47%, and th...

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Abstract

The invention relates to a method of preparing 1,2-epoxycyclododecane through epoxidation cyclododecene by utilization of tert-butyl hydroperoxide (TBHP). According to the method, addition of the TBHP is controlled under the existence of a catalyst, and the system concentration of an oxidant is controlled by adopting a batch addition manner to reduce generation of side reactions, thus ensuring complete conversion of the cyclododecene and achieving high selectivity of the main product 1,2-epoxycyclododecane. The excess TBHP is converted by adding another low-molecular-weight olefin to cogenerate a low-molecular-weight epoxy compound, thus ensuring safety of subsequent separation and facilitating process amplification.

Description

technical field [0001] The present invention relates to a method for producing epoxycyclododecane by epoxidation of cyclododecene, more specifically, the present invention relates to a method for continuous production of cyclododecene by epoxidation of cyclododecene with tert-butyl hydroperoxide Method for epoxycyclododecane. Background technique [0002] Epoxycyclododecane is an important chemical intermediate for the preparation of cyclododecanone and its derived muscone, laurolactam, and further products such as musk and nylon 12. [0003] Oxygen and hydrogen peroxide are often used as oxygen sources for olefin epoxidation in industry. Although oxygen is the most ideal oxidant, it is difficult to obtain satisfactory results for direct epoxidation of other olefins with oxygen except ethylene. For example, in US4469880, it is mentioned that a metal borate is used as a catalyst and oxygen is an oxygen source to carry out an epoxidation reaction process of cyclododecene. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/19
CPCC07D301/19C07D303/04
Inventor 陈海波张彦雨李俊平李静黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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