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Method for preparing ethylidene norbornene by isomerization of vinyl norbornene

A technology of vinyl norbornene and ethylidene norbornene, which is applied in the field of isomerization of vinyl norbornene to prepare ethylidene norbornene, which can solve the problems of harsh preparation and storage conditions, large reaction temperature rise, and difficulty in control, etc. problems, achieve excellent catalytic performance, fast reaction rate, and easy control of temperature rise

Active Publication Date: 2020-09-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for solid bases, especially solid super strong bases, the higher the base strength, the harsher the preparation and storage conditions, the higher the reaction temperature rise and it is difficult to control, and the corrosion is strong.
In addition, the isomer ratio of the two isomers of ENB in ​​the product also has a certain potential impact on its later application, but there is currently no patent report on the regulation of the product isomer ratio

Method used

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  • Method for preparing ethylidene norbornene by isomerization of vinyl norbornene
  • Method for preparing ethylidene norbornene by isomerization of vinyl norbornene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1. A method for preparing ethylidene norbornene by isomerizing vinyl norbornene:

[0034] 20g of AACH was calcined in an inert gas atmosphere at a temperature of 500°C for 4 hours to obtain a carrier. Weigh 5.18g (0.235mol) Na and 1.8g (0.045mol) NaOH, make a mixture, put them into a stirring tank and stir together, adjust the temperature to 500°C, react for 1h, and cool to obtain solid base catalyst A. After testing, its alkali strength is 26, and its alkali content is 10mmol.g -1 .

[0035] Take 100mL (84.1g) VNB and put it into the reactor, 2 (until the air in the reactor is completely replaced by N 2 ), heated to a constant temperature of 90°C. Weigh 5 parts of 1wt% (0.841g) catalyst A, totaling 5wt% (4.205g), add 1wt% catalyst at the beginning of the reaction, then add 1wt% catalyst every 1h. Sampling at intervals, analyzed by gas chromatography, calculating the conversion rate of the reaction, the isomerization ratio of the product, VNB is basicall...

Embodiment 2

[0036] Embodiment 2, a method for preparing ethylidene norbornene by isomerization of vinyl norbornene:

[0037] The catalyst was prepared as described in Example 1.

[0038] Take 100mL (84.1g) VNB and put it into the reactor, 2, heated to a constant temperature of 90°C. Weigh 1 part of 5wt% (4.205g) catalyst A and add it to the reaction kettle at one time. Sampling at intervals, analyzed by gas chromatography, calculating the conversion rate of the reaction, the isomerization ratio of the product, VNB is basically converted into ENB during 5h, the reaction conversion rate is 99.7%, the selectivity is 99.5%, and the isomerization ratio Z / E is 4.2. After filtering, the filtrate is the product - ethylidene norbornene (ENB), with a purity of 98.7%.

Embodiment 3

[0039] Embodiment 3, a method for preparing ethylidene norbornene by isomerization of vinyl norbornene:

[0040] The catalyst was prepared as described in Example 1.

[0041] Take 100mL (84.1g) VNB and put it into the reactor, 2 , heated to a constant temperature of 90°C. Weigh 10 parts of 0.5wt% (0.4205g) catalyst A, totaling 5wt% (4.205g), and add 0.5wt% catalyst every 1h. Sampling at intervals, using gas chromatographic analysis to calculate the conversion rate of the reaction, the isomerization ratio of the product, VNB is basically converted into ENB in ​​the time of 10h, the reaction conversion rate is 99.9%, the selectivity is 99.6%, the isomerization ratio Z / E is 3.1. After filtration, the filtrate is the product - ethylidene norbornene (ENB), with a purity of 99.2%.

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Abstract

The invention discloses a method for preparing ethylidene norbornene by isomerizing vinyl norbornene. The method comprises the following steps: 1) preparing a solid alkali catalyst: preparing the solid alkali catalyst from alkali metal and alkali metal hydroxide by using ammonium aluminum carbonate hydroxide as a carrier precursor, wherein the alkali strength of the solid alkali catalyst is 20-33,and the alkali content of the solid alkali catalyst is 5-15 mmol.g<-1>; 2) adding dewatered vinyl norbornene into a stirring kettle, introducing inert gas, and preheating the stirring kettle to a reaction temperature; and 3) adding the weighed solid alkali catalyst into the stirring kettle in batches, carrying out heat-preservation stirring reacting at the reaction temperature for 1-10 h, coolingthe obtained reaction product to room temperature, and filtering the cooled reaction product to obtain a filtrate that is the ethyl norbornene. The method has the advantages of simple and easily controlled process, good mass transfer and heat transfer effects, obtaining of the high-quality pure product, adjustability in the heterogeneous ratio of the reaction product, and small use amount easy separation of the catalyst.

Description

technical field [0001] The invention relates to a method for preparing ethylidene norbornene by isomerizing vinyl norbornene, that is, a process and a formula for preparing ethylidene norbornene by using a solid base to isomerize vinyl norbornene. Background technique [0002] Ethylidene norbornene (ENB) is a colorless transparent liquid at room temperature, has a strong camphor-like odor, and is relatively volatile in the air. The odor can be smelled when the concentration in the air is 0.014ppm. At present, ENB is mainly used in the synthesis of ethylene propylene diene monomer (EPDM), which has high polymerization activity; there are few secondary reaction opportunities for branching rubber molecules and forming gel; the vulcanization speed of the product is fast, and it is the first choice for EPDM. monomer. In recent years, the application of ENB has further expanded to the downstream elastomer materials and similar fields of multi-variety norbornene compounds with bro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C5/25C07C13/43B01J27/236
CPCB01J27/236C07C5/2556C07C2523/04C07C2527/236C07C13/43
Inventor 姚臻曹堃吴盈吴敏芳袁贝
Owner ZHEJIANG UNIV
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