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Method for producing hexahydrophthalic anhydride by using C4 mixture

A technology of mixing carbon tetrahydrophthalic anhydride and hexahydrophthalic anhydride, which is applied in organic chemistry and other fields, can solve problems such as high production cost, catalyst poisoning, and influence on reaction conversion rate and selectivity, and achieve low production cost, reduced production cost and energy consumption, The effect of inhibiting the occurrence of side effects

Active Publication Date: 2010-07-07
PUYANG HUICHENG ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, hexahydrophthalic anhydride is produced by catalytic hydrogenation of tetrahydrophthalic anhydride synthesized by the Diels-Alder reaction of butadiene and maleic anhydride. The production cost of this method is relatively high, and tetrahydrophthalic anhydride is It is also prone to side reactions such as condensation and hydrogenolysis, and generates high-boiling and low-boiling impurities that are difficult to separate, which not only affects the reaction conversion rate and selectivity, but also high-boiling by-products are easily coked and adsorbed on the surface of the catalyst, resulting in catalyst poisoning

Method used

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  • Method for producing hexahydrophthalic anhydride by using C4 mixture
  • Method for producing hexahydrophthalic anhydride by using C4 mixture
  • Method for producing hexahydrophthalic anhydride by using C4 mixture

Examples

Experimental program
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Effect test

Embodiment 1

[0016] At 80 ℃, 100 grams of maleic anhydride, 0.009 grams of p-hydroxyanisole and 0.001 grams of [Cu 2 (PPh 3 ) 6 (μ-OOCH))(C)O 4 ), gradually add mixed carbon four (its main component is butadiene), generate tetrahydrophthalic anhydride through Diels-Alder reaction, and add Pd / BaSO to the generated tetrahydrophthalic anhydride after GC detection 4 Catalyst 3.0 g and [Cu 4 (C 7 H 4 NO 4 ) 2 (dppm) 4 ](NO 3 ) 2 0.03 g. Catalytic hydrogenation was carried out in an autoclave with a temperature of 140°C and a hydrogen pressure of 4.0 MPa for 3 hours. After cooling, the catalyst was filtered and distilled under reduced pressure to obtain 139.9 g of colorless liquid hexahydrophthalic anhydride. The yield was 90% and the melting point was 36°C. .

[0017] 1 HNMR(300MHz, CDCl 3 ), δ / ppm: 3.12-3.15 (m, 2H; CH), 1.85-1.91 (m, 4H; CH 2 ), 1.50-1.53(m, 4H; CH 2 );

[0018] 13 CNMR(300MHz, CDCl 3 ), 8 / ppm: 172.8, 40.4, 23.7, 21.9;

[0019] IR(KBr), v / cm -1 : 2948, 2862, 1867, 1787, 1694, 1257, ...

Embodiment 2

[0022] At 150°C, 100 grams of maleic anhydride, 0.08 grams of p-hydroxyanisole and 0.02 grams of [Cu 2 (PPh 3 ) 6 (μ-OOCH))(C1O 4 ), gradually add mixed carbon four (its main component is butadiene), generate tetrahydrophthalic anhydride through Diels-Alder reaction, and add Pd / BaCO to the generated tetrahydrophthalic anhydride after the reaction is detected by GC 3 Catalyst 3.2 g and [Cu 4 (C 7 H 4 NO 4 ) 2 (dppm) 4 ](NO 3 ) 2 0.04 g. Catalytic hydrogenation was carried out in an autoclave with a temperature of 120°C and a hydrogen pressure of 2.0 MPa for 5 hours. After cooling, the catalyst was filtered and distilled under reduced pressure to obtain 143.0 g of colorless liquid hexahydrophthalic anhydride. The yield was 93% and the melting point was 36°C. .

Embodiment 3

[0024] At 120°C, 100 grams of maleic anhydride, 0.042 grams of p-hydroxyanisole and 0.008 grams of [Cu 2 (PPh 3 ) 6 (μ-OOCH))(ClO 4 ), gradually add the mixed carbon four (its main component is butadiene), and generate tetrahydrophthalic anhydride through Diel-Alder reaction. After the reaction is detected by GC, add Pd / BaCO to the generated tetrahydrophthalic anhydride 3 Catalyst 3.0 g and [Cu 4 (C 7 H 4 NO 4 ) 2 (dppm) 4 ](NO 3 ) 2 0.04 g. Catalytic hydrogenation was carried out in an autoclave at a temperature of 100°C and a hydrogen pressure of 1.0 MPa for 6 hours. After cooling, the catalyst was filtered and distilled under reduced pressure to obtain 144.6 g of colorless liquid hexahydrophthalic anhydride. The yield was 92% and the melting point was 35°C. .

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Abstract

The invention discloses a method for producing hexahydrophthalic anhydride by using C4 mixture and belongs to the field of organic synthesis. The method comprises the following steps: using maleic anhydride and C4 mixture, which mainly containing butadiene, as the raw materials; under the actions of the HC-200102P compound catalyst [p-hydroxyanisole and Cu2(PPh3)6(mu-OOCH)(ClO4), directly using maleic anhydride to absorb the C4 mixture to obtain tetrahydrophthalic anhydride; and carrying out catalytic hydrogenation on the tetrahydrophthalic anhydride by using the CC-1 compound catalyst (Pd / BaSO4 or Pd / BaCO3, and Cu4(C7H4NO4)2(dppm)4(NO3)2, thereby obtaining the hexahydrophthalic anhydride. The method enhances the reaction selectivity, reduces the production cost, reduces the environmental pollution and has industrialized popularization value.

Description

Technical field [0001] The invention relates to a production method of chemical products, in particular to a production method of hexahydrophthalic anhydride, belonging to the field of organic synthesis. Background technique [0002] Mixed carbon four is a by-product in the process of cracking natural gas and petroleum hydrocarbons to produce ethylene, and its main component is butadiene. At present, butadiene in mixed C4 is mainly extracted by solvent extraction through a large-scale extraction device, which requires large equipment investment and high production costs. Hexahydrophthalic anhydride (HHPA), the full name of hexahydrophthalic anhydride, is a colorless, clear and viscous liquid. It solidifies into a glassy solid at 35-36°C. It has a saturated and stable six-membered ring structure. It is an electronic information material, medicine, An important intermediate in pesticides, resins and national defense industry, mainly used as epoxy curing agents, coatings, plasticiz...

Claims

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Application Information

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IPC IPC(8): C07D307/89
Inventor 杨振强张海洋吕海宽李江涛韩兆海蒋卫鹏郭利兵陈淑敏张鹏可马伟英方少明杨瑞娜
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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