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Preparation method of exterior sodium dick acid anhydride

A nadic acid anhydride and exterior technology, applied in the field of organic chemical synthesis, can solve problems such as environmental pollution, reduce production costs, reduce solvent pollution, and strengthen deep processing and utilization.

Active Publication Date: 2012-10-03
PUYANG HUICHENG ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the traditional production method of external nadic anhydride is to use cyclopentadiene and maleic anhydride as raw material for internal nadic anhydride prepared by Diels-Alder reaction. Repeated recrystallization and purification to obtain the pure product of exo-nadic anhydride (Journal of the American Chemical Society, 1967, 69:6897-6904), or repeated crystallization from the solvent after heating at high temperature to obtain the target product (Organic Letters, 2010, 12(13 ): 2904-2907); the yields of the above methods are all less than 40%, and the repeated crystallization of the solvent is required to produce a large amount of waste liquid and pollute the environment

Method used

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  • Preparation method of exterior sodium dick acid anhydride
  • Preparation method of exterior sodium dick acid anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Under stirring conditions at 0°C, gradually add maleic anhydride to 60 g of mixed carbon five, stop the reaction when there is no cyclopentadiene detected by GC, add 20.9 g of maleic anhydride, and filter with suction to obtain 33.2 g internal Nadic acid anhydride, melting point 160-162 ℃, purity 98% (GC), yield 95%. 1 H NMR (300Hz, CDCl 3 ),δ / ppm: 6.313(2H, t, J=1.778Hz, 5-H, 6-H), 3.571-3.611(2H, m, 2-H, 3-H), 3.496-3.528(2H, m , 1-H, 4-H), 1.765-1.806(1H, m, 7-H), 1.572-1.604(1H, dd, J 1 =0.51Hz,J 2 =9.0Hz, 7-H); 13 C NMR (300Hz, CDCl 3 ), δ / ppm: 171.4, 135.4, 52.7, 47.0, 46.0.

[0019] Add the above-mentioned 33.2 g of endo-nadic anhydride, 200 mL of ethanol as solvent, 6.6 g of urotropine, 16.6 mg of benzoyl peroxide and 2.3 g of [Cu(dppm)(NO 3 )] 2 As a catalyst, after 10 h of reflux reaction, the catalyst was removed by filtration, and the solvent was recovered under reduced pressure. The mixed solvent of 100 mL toluene and 100 mL acetone was crystallized ...

Embodiment 2

[0021] Under stirring conditions at 2°C, gradually add maleic anhydride to 300 g of mixed carbon five, stop the reaction when no cyclopentadiene is detected by GC, add 105 g of maleic anhydride in total, and centrifuge the reaction mixture, 168 g of endo-nadic anhydride was obtained, with a melting point of 162-164°C, a purity of 99% (GC), and a yield of 95%.

[0022] Add the above-mentioned 168 g of internal Nadic anhydride, 800 mL of isopropanol as solvent, 16.8 g of urotropine, 50.4 mg of benzoyl peroxide and 16.8 g of [Cu(dppm)(NO 3 )] 2 As a catalyst, after 24 h of reflux reaction, the catalyst was removed by filtration, and the solvent was recovered under reduced pressure. The mixed solvent of 400 mL toluene and 400 mL acetone was crystallized to obtain 163 g of pure exo-nadic acid anhydride, with a melting point of 140-142 °C and a purity of 98% (GC) , yield 97%.

Embodiment 3

[0024] Under stirring conditions at 5°C, gradually add maleic anhydride to 1800 g of mixed carbon five, stop the reaction when there is no cyclopentadiene detected by GC, add 630 g of maleic anhydride in total, and centrifuge the reaction mixture, 1013 g of endo-nadic anhydride was obtained, with a melting point of 160-162 °C, a purity of 98% (GC), and a yield of 96%.

[0025] In the reactor, add the above-mentioned 1013 g internal Nadic anhydride, 5 L propanol as a solvent, 304 g of urotropine, 0.81 g of benzoyl peroxide and 40.6 g of [Cu (dppm) (NO 3 )] 2 As a catalyst, after 16 hours of reflux reaction, the catalyst was removed by filtration, the solvent was recovered under reduced pressure, and the mixed solvent of 2 L toluene and 2 L acetone was recrystallized to obtain 973 g of pure Nadic anhydride, with a melting point of 140-142 °C and a purity of 98% (GC ), yield 96%.

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Abstract

The invention discloses a new method for producing exterior sodium dick acid anhydride, belonging to the synthesis field of organic chemistry. In the method, maleic anhydride and mixed carbon five are taken as raw materials. The method comprises the steps of: directly absorbing cyclopentadiene by maleic anhydride at 0-5 DEG C to react so as to generate interior sodium dick acid anhydride; and taking the interior sodium dick acid anhydride as a raw material, taking short chain alcohol as solvent, and taking urotropin, benzoyl peroxide and (Cu (dppm) (NO3)) 2 as catalyst to synthesize the exterior sodium dick acid anhydride. Compared with the prior art, in the method, a low-price ethane byproduct and the mixed carbon five are taken as the raw material to prepare the exterior sodium dick acid anhydride, so that the yield is obviously higher than the conventional technology and reaches more than 96%, and the solvent pollution is reduced; and therefore, the method is more suitable for the industrial production.

Description

Technical field [0001] The present invention involves a production method of a chemical product, especially a production method for the appearance of Nadik acidic anhydride, which is an organic chemical synthesis field. Background technique [0002] CIS-5-Norbornene-EXO-2,3-Dicarboxylic Anhydride, also known as Shun-5-lycnene-outer-2,3-di carboxylic anhydride, colorless transparent crystals, molecular type C C 9 H 8 O 3 , Molecular weight 164.16, slightly soluble in petroleum ether, soluble in organic solvents such as benzene, toluene, acetone, tetrachloride, chloroform, ethanol, and ethyl acetate.EssenceAt present, the application of Nadik acidic anhydride is mostly internal products. Nadicic acidicine is mainly used as a modified agent, rubber sulfur sulfur, resin, resin, resin, resin, resin, and pine lipidPlasticidants, textile finishing penetration agents, etc. In addition, it is also widely used in varnish, magnetic paint, alcoholic acid resin coatings, etc.When Nadik acidic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/89
CPCY02P20/584
Inventor 王中锋陈淑敏冯培培吕海宽张鹏可崔富民周铎孙玉霞李会平
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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