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Endo-methylene hexahydrophthalic anhydride and production method thereof

A technology of endomethylene hexahydrophthalic anhydride and production method, which is applied in the field of organic chemical synthesis, can solve problems such as insufficient development and utilization, achieve convenient industrial production, reduce production cost, and reduce environmental pollution Effect

Active Publication Date: 2010-04-21
PUYANG HUICHENG ELECTRONICS MATERIAL
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the continuous development of my country's petroleum industry, the output of dicyclopentadiene as a by-product of the production of ethylene is also increasing, but most of them have not been fully developed and utilized. In order to solve the comprehensive utilization of dicyclopentadiene in my country problems, and at the same time provide the chemical industry with a very broad application prospect of endomethylene hexahydrophthalic anhydride, therefore, it is of great significance to study its synthesis method

Method used

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  • Endo-methylene hexahydrophthalic anhydride and production method thereof
  • Endo-methylene hexahydrophthalic anhydride and production method thereof
  • Endo-methylene hexahydrophthalic anhydride and production method thereof

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Effect test

Embodiment 1

[0014] Under stirring conditions at 0°C, gradually add maleic anhydride to 600g of mixed carbon five, stop the reaction when there is no cyclopentadiene detected by gas chromatography, add 209g of maleic anhydride in total, filter with suction, and the solid is crystallized 290 g of nadic anhydride was obtained, yield 83%.

[0015] Then, add catalyst 8.7g (the loading capacity of Ni is 10wt.%, n Co : n Ni =1:100), in the autoclave of temperature 140 ℃, hydrogen pressure 3MPa, carry out catalytic hydrogenation reaction 4 hours, filter catalyst after cooling, underpressure distillation obtains endomethylene hexahydrophthalic anhydride 261g, yield 90%.

[0016] 1 HNMR (300MHz, CDCl 3 ), δ / ppm: 3.15 (2H, CH), 2.13 (2H, CH), 1.77 (1H, CH), 1.74 (2H, CH 2 ), 1.52 (1H, CH), 1.47 (2H, CH 2 );

[0017] 13 CNMR (100MHz, CDCl 3 ), δ / ppm: 171.4, 47.2, 39.2, 34.5, 27.2;

[0018] IR(KBr), v / cm -1 : 2948, 1894, 1787, 1267, 1221, 1030, 972, 907;

[0019] Ms(m / z): 166.2(M + ).

Embodiment 2

[0021] Under stirring condition at 2°C, gradually add maleic anhydride to 6Kg mixed carbon five, stop the reaction when no cyclopentadiene is detected by gas chromatography, add 2.1Kg maleic anhydride in total, and centrifuge the reaction mixture, The liquid was vaporized, compressed, and condensed to obtain 4.8Kg of decyclized C5, and the solid was crystallized to obtain 2.6Kg of Nadic anhydride, with a yield of 73%.

[0022] Then, add catalyst 78g (the loading capacity of Ni is 20wt.% in the nadic acid anhydride of generation, n Co : n Ni =1:50), in the autoclave of temperature 110 ℃, hydrogen pressure 4MPa, carry out catalytic hydrogenation reaction 5 hours, filter catalyst after cooling, underpressure distillation obtains endomethylene hexahydrophthalic anhydride 2.4Kg, collects The rate is 92%.

Embodiment 3

[0024] Under stirring conditions at 5°C, gradually add maleic anhydride to 18Kg mixed carbon five, stop the reaction when no cyclopentadiene is detected by gas chromatography, add 6.3Kg maleic anhydride altogether, and centrifuge the reaction mixture, The liquid was vaporized, compressed, and condensed to obtain 13.8Kg of decyclized C5, and the solid was crystallized to obtain 8.4Kg of Nadic anhydride, with a yield of 79%.

[0025] Then, add catalyst 252g (the loading capacity of Ni is 40wt.%, n Co : n Ni =1:200), in the autoclave of temperature 130 ℃, hydrogen pressure 1MPa, carry out catalytic hydrogenation reaction 6 hours, filter catalyst after cooling, underpressure distillation obtains endomethylene hexahydrophthalic anhydride 7.5Kg, collects Rate 90%.

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Abstract

The invention relates to endo-methylene hexahydrophthalic anhydride and a production method thereof, belonging to the field of organic chemical synthesis. The production method comprises the following steps of: directly absorbing cyclopentadiene by maleic anhydride for reaction to generate nadic anhydride by using maleic anhydride and mixed C5 as raw materials under 0-5 DEG C so as to obtain purifying products of the nadic anhydride through crystallization; then adding a Co-Ni / ZnO-ZrO2 catalyst into the generated nadic anhydride, carrying out catalytic hydrogenation reaction for 4-6 hours in an autoclave at the temperature of 100-140 DEG C and the hydrogen pressure of 1-4 MPa; filtering the Co-Ni / ZnO-ZrO2 catalyst after cooling; and distilling with reduced pressure to obtain the endo-methylene hexahydrophthalic anhydride. Compared with the prior art, the invention has the advantages that the nadic anhydride is prepared by taking a low-cost ethene by-product, i.e. the mixed C5, as the raw material, the endo-methylene hexahydrophthalic anhydride is further synthesized, a chemical raw material, i.e. decycling C5 is obtained simultaneously, the deep processing utilization of the mixed C5 is enhanced, and popularization and application value is realized.

Description

technical field [0001] The invention relates to a chemical product and a production method thereof, in particular to endomethylene hexahydrophthalic anhydride and a production method thereof, belonging to the field of organic chemical synthesis. Background technique [0002] 5-norbornene-2,3-dicarboxylic anhydride (nadic anhydride) is an important chemical raw material, widely used in many fields such as electronic information materials, synthetic resins and plastics, pesticides and pharmaceuticals, and its preparation process is simple, The cost of raw materials is lower. In addition, the resin synthesized as a raw material has better air-drying properties, higher heat resistance, better finish, higher electrical properties, and corrosion resistance and mechanical strength, etc. Endomethylene hexahydrophthalic anhydride is the product of hydrogenation with Nadic anhydride catalyst. Compared with nadic anhydride, endomethylene hexahydrophthalic anhydride has more stable ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93B01J23/80
CPCB01J37/031B01J23/80B01J23/002C07D307/93B01J2523/00B01J2523/27B01J2523/48B01J2523/845B01J2523/847B01J2523/17C07D307/89
Inventor 杨振强张海洋李江涛郭利兵吕海宽韩兆海蒋卫鹏陈淑敏马伟英周铎杨瑞娜
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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