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Novel method for producing methyl hexahydrobenzene anhydride

A technology of methyl hexahydrophthalic anhydride and methyl tetrahydrophthalic anhydride, applied in the new field of producing methyl hexahydrophthalic anhydride, can solve problems such as easy coking, high boiling point, catalyst poisoning, etc. The effect of mild reaction conditions

Inactive Publication Date: 2006-02-22
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Methyl hexahydrophthalic anhydride is usually produced by catalytic hydrogenation of methyl tetrahydrophthalic anhydride. During the hydrogenation process, the double bond of methyl tetrahydrophthalic anhydride is activated, and the double bond is easily transferred. Incomplete hydrogenation results in the generation of by-product transposition methyl tetrahydrophthalic anhydride. At the same time, under the action of hydrogen atoms, the acid anhydride is also prone to side reactions such as condensation, hydrogenolysis, and cross-linking, resulting in high-boiling point and low-boiling point impurities that are difficult to separate. , not only affect the reaction conversion rate, selectivity and yield, but also the high boiling point by-products are easy to coke at the reaction temperature and adsorb on the surface of the catalyst, leading to catalyst poisoning
The boiling point of methyl tetrahydrophthalic anhydride and its isomers is close to that of methyl hexahydrophthalic anhydride, and the boiling point is high. After the reaction, it is difficult to effectively separate through traditional separation methods such as rectification, which seriously affects product quality.

Method used

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  • Novel method for producing methyl hexahydrobenzene anhydride
  • Novel method for producing methyl hexahydrobenzene anhydride
  • Novel method for producing methyl hexahydrobenzene anhydride

Examples

Experimental program
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Effect test

Embodiment 1

[0022] At a temperature of 50°C and in the presence of 3 grams of aluminum chloride, gradually add decyclized carbon five (its main components are isoprene and piperylene) to 98 grams of maleic anhydride, through the Diels-Alder reaction Methyltetrahydrophthalic anhydride is produced. Then add 1 gram of skeleton nickel and 0.1 gram of bis(bis-diphenylphosphinoxyethane) copper tetrabromide polymer to the generated methyltetrahydrophthalic anhydride, in an autoclave at a temperature of 140° C. and a hydrogen pressure of 4 MPa The catalytic hydrogenation reaction was carried out for 4 hours, the catalyst was filtered after cooling, and 152 g of colorless liquid methyl hexahydrophthalic anhydride was obtained by distillation under reduced pressure, with a yield of 90.3%.

Embodiment 2

[0024] At a temperature of 80°C and in the presence of 1.5 grams of aluminum chloride, gradually add decyclized carbon five (its main components are isoprene and piperylene) to 98 grams of maleic anhydride to react to generate methyltetrahydrophthalic anhydride. Then add 2.5 grams of skeleton nickel and 0.3 grams of bis(bis-diphenylphosphinoxyethane) copper tetrabromide polymer to the generated methyltetrahydrophthalic anhydride, in an autoclave with a temperature of 120 ° C and a hydrogen pressure of 2 MPa The catalytic hydrogenation reaction was carried out for 5 hours, the catalyst was filtered after cooling, and 157 g of colorless liquid methyl hexahydrophthalic anhydride was obtained by distillation under reduced pressure, with a yield of 93.3%.

Embodiment 3

[0026] In the presence of a temperature of 120° C. and 0.5 g of zinc chloride, gradually add decyclized C5 (its main components are isoprene and piperylene) to 98 g of maleic anhydride to react to generate methyltetrahydrophthalic anhydride. Then add 5 grams of skeleton nickel and 0.5 grams of bis(bis-diphenylphosphinoxyethane) copper tetrabromide polymer to the generated methyltetrahydrophthalic anhydride, in an autoclave with a temperature of 100 ° C and a hydrogen pressure of 1 MPa The catalytic hydrogenation reaction was carried out for 6 hours, the catalyst was filtered after cooling, and 155 g of colorless liquid methyl hexahydrophthalic anhydride was obtained by distillation under reduced pressure, with a yield of 92.2%.

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Abstract

The invention discloses a new preparation method for methyl hexahydro benzoic anhydride. Wherein, using cisanhydride, isoprene and pentadiene as raw material; absorbing directly isoprene and pentadiene with catalyst to generate methyl tetrahydro benzoic anhydride that generates the objective product by using catalytic hydrogenation reaction with composite catalyst with high activity and selectivity. The reaction condition is mild, and the product yield is increased from 65-75% to 90-95%.

Description

technical field [0001] The invention relates to a new production method of chemical products, in particular to a new production method of methyl hexahydrophthalic anhydride. Background technique [0002] Methylhexahydrophthalic anhydride, referred to as methylhexahydrophthalic anhydride (MHHPA), is a colorless transparent liquid with molecular formula C 9 h 12 0 3 , molecular weight 168.19, specific gravity 1.162g / cm 3 , relative density d 4 25 1.168, flash point ≥ 160°C, vapor pressure 0.7kPa / 127°C, soluble in benzene, toluene, acetone, carbon tetrachloride, chloroform, glycol, ethyl acetate, slightly soluble in petroleum ether. Methylhexahydrophthalic anhydride has a saturated and stable six-membered ring structure and exists in a liquid state. It is an important intermediate in electronic information materials, medicine, pesticides, resins, and national defense industries. In recent years, it has been widely used, mainly used in epoxy resin curing agent, coating, pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60
Inventor 郭利兵张海洋赵东杨瑞娜赵亮傅鹏飞席振峰
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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