Method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic anhydride through microwave reaction

A microwave reaction and norbornene technology, applied in the direction of organic chemistry, can solve the problems of complicated operation, low translocation yield, high toxicity of additives, etc., and achieve the effects of simple reaction process, short reaction time and few by-products.

Active Publication Date: 2014-11-05
YANGTAI PHARMA SHANDONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Patent Application Publication No. JP2011184340A discloses that cis-5-norbornene-endo-2,3-dicarboxylic anhydride is used as a raw material, and it is prepared by heating and transposition at a high temperature of 200°C for up to 6 hours. The disadvantages are: The transposition yield of the obtained product is low, only 35%, and due to the incomplete transposition of raw materials, it is easy to produce 12% oxide impurities, so it is necessary to add antioxidant additives to reduce oxide impurities. Such additives are more toxic and Relatively expensive, not conducive to mass production
[0005] Disclosed in the patent application publication number CN101362751A: maleimide and cyclopentadiene are reacted to obtain cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride, the weak point of this method is: operation It is cumbersome and the product contains cis-5-norbornene-exo-2,3-dicarboxylic anhydride, cis-5-norbornene-endo-2,3-dicarboxylic anhydride and oxide impurities. Type products are more difficult and difficult to produce on a large scale

Method used

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Effect test

Embodiment 1

[0031] A method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic anhydride by microwave reaction, using cis-5-norbornene-inner-2,3-dicarboxylic anhydride as raw material, Specific steps are as follows:

[0032] (1) In a 1L reaction flask, stir 100g of cis-5-norbornene-endo-2,3-dicarboxylic acid anhydride and 100mL of xylene evenly, put it into a microwave reaction kettle, raise the temperature to 180°C, and Microwave reaction under 0.3-10GHz microwave for 5 minutes;

[0033] (2) After the reaction is completed, cool the reactor in step (1) to 90°C, place it in an oil bath and stir for 30 minutes to crystallize, cool to room temperature, filter, and dry to obtain the product cis-5-norbornene-exo Type-2,3-dicarboxylic acid anhydride 70.2g; yield: 70.2%; purity: 98.6%; oxide impurity content: 0.05%.

Embodiment 2

[0035] A method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic anhydride by microwave reaction, using cis-5-norbornene-inner-2,3-dicarboxylic anhydride as raw material, Specific steps are as follows:

[0036] (1) In a 1L reaction flask, stir 200g of cis-5-norbornene-endo-2,3-dicarboxylic acid anhydride and 800mL of butyl acetate evenly, put it in a microwave reaction kettle, heat up to 220°C, and The microwave reaction was carried out for 6 minutes under the microwave with a frequency of 10-100 GHz;

[0037] (2) After the reaction is complete, cool the reactor in step (1) to 100°C, place it in an oil bath and stir for 30 minutes to crystallize, cool to room temperature, filter, and dry to obtain the product cis-5-norbornene-exo Type-2,3-dicarboxylic acid anhydride 145.2g; yield: 72.6%; purity: 98.2%; oxide impurity content: 0.06%.

Embodiment 3

[0039] A method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic anhydride by microwave reaction, using cis-5-norbornene-inner-2,3-dicarboxylic anhydride as raw material, Specific steps are as follows:

[0040] (1) In a 1L reaction flask, stir 200g of cis-5-norbornene-endo-2,3-dicarboxylic acid anhydride and 600mL of toluene evenly, put it into a microwave reaction kettle, heat up to 200°C, at a frequency of Microwave reaction under 100-200GHz microwave for 8 minutes;

[0041] (2) After the reaction is completed, cool the reactor in step (1) to 110°C, place it in an oil bath and stir for 30 minutes to crystallize, cool to room temperature, filter, and dry to obtain the product cis-5-norbornene-exo Type-2,3-dicarboxylic acid anhydride 160.2g; yield: 80.1%; purity: 98.2%; oxide impurity content: 0.06%.

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Abstract

The invention relates to a method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic anhydride through microwave reaction. According to the invention, cis-5-norbornene-endo-2,3-dicarboxylic anhydride is well mixed with a solvent, and the mixture is placed into a mirowave reaction kettle; temperature and time are set, and a microwave reaction is carried out; oil bath and stirring are carried out, such that crystallization is allowed; the obtained material is cooled to room temperature, and is filtered and dried, such that the product cis-5-norbornene-exo-2,3-dicarboxylic anhydride is obtained. With the method, product yield is up to 80% and purity is up to 98%. Compared to prior arts, the method provided by the invention does not pollute the environment, has clean process, and is environment-friendly. The method is suitable for large-scale productions.

Description

technical field [0001] The invention relates to a method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride by microwave reaction. Background technique [0002] Cis-5-norbornene-exo-2,3-dicarboxylic anhydride is an important raw material for the synthesis of antidepressant lurasidone, and its structural formula is: [0003] . [0004] Patent Application Publication No. JP2011184340A discloses that cis-5-norbornene-endo-2,3-dicarboxylic anhydride is used as a raw material and prepared by heating and transposition at a high temperature of 200°C for up to 6 hours. The disadvantages are: The transposition yield of the obtained product is low, only 35%, and due to the incomplete transposition of raw materials, it is easy to produce 12% oxide impurities, so it is necessary to add antioxidant additives to reduce oxide impurities. Such additives are more toxic and Relatively expensive, not conducive to mass production. [0005] Disclosed in the paten...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93
CPCC07D307/93
Inventor 于勇倪廷峻弘蔡瞻冯永斌赵宗玉
Owner YANGTAI PHARMA SHANDONG
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