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Method for producing class of norbornene derivative

A norbornene and production method technology, applied in the field of organic synthesis, can solve the problems of increasing production costs, affecting the reaction process and product conversion rate, environmental pollution, etc., and achieve the effects of strengthening deep processing and utilization, fully utilizing raw materials, and reducing production costs

Inactive Publication Date: 2010-07-14
PUYANG HUICHENG ELECTRONICS MATERIAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem of this method is that a lot of waste residues that are difficult to handle will be produced when cracking dicyclopentadiene, which will cause environmental pollution and increase production costs. In addition, cyclopentadiene and the like are prone to polymerization during the Diels-Alder diene addition process, resulting in a large number of by-products. products, affecting reaction progress and product conversion

Method used

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  • Method for producing class of norbornene derivative
  • Method for producing class of norbornene derivative
  • Method for producing class of norbornene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] At a temperature of 5 °C and stirring, 0.55 g of tert-butylcatechol and 0.11 g of [Cu 2 (dppm) 2 (C 7 H 7 N)(μ-NO 3 )](NO 3 ) mixture, gradually add acrylonitrile, stop the addition when there is no cyclopentadiene detected by GC, and add 80.4 g of acrylonitrile in total. The reaction mixture was vaporized, compressed and condensed to obtain 578.2 g of decyclic Cpenta; the residue was distilled under reduced pressure with an oil pump to obtain 157.2 g of 2-cyano-5-norbornene with a yield of 87.8%.

Embodiment 2

[0018] At a temperature of 0 °C and stirring, 0.13 g of tert-butylcatechol and 0.13 g of [Cu 2 (dppm) 2 (C 7 H 7 N)(μ-NO 3 )](NO 3 ) mixture, gradually add acrylic acid, stop adding when there is no cyclopentadiene detected by GC, and add 131.0 g of acrylic acid in total. The reaction mixture was vaporized, compressed and condensed to obtain 733.7 g of decyclic Cpenta; the residue was distilled under reduced pressure with an oil pump to obtain 211.4 g of 5-norbornene-2-carboxylic acid with a yield of 85.2%.

Embodiment 3

[0020] At a temperature of 2 °C and stirring, 0.40 g of tert-butylcatechol and 0.11 g of [Cu 2 (dppm) 2 (C 7 H 7 N)(μ-NO 3 )](NO 3 ) mixture, gradually add tert-butyl acrylate, stop adding when there is no cyclopentadiene detected by GC, and add 255.9 g of tert-butyl acrylate in total. The reaction mixture was vaporized, compressed and condensed to obtain 770.0 g of decyclic Cpenta; the residue was distilled under reduced pressure with an oil pump to obtain 318.6 g of tert-butyl 5-norbornene-2-carboxylate with a yield of 82.0%.

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Abstract

The invention discloses a method for producing class of norbornene derivative, belonging to the field of organic synthesis. In the method, tert-butyl catechol and [Cu2(dppm)2(C7H7N)(mu-NO3)](NO3) are taken as catalysts, propylene compound and mixed C5 are taken as raw materials, cyclopentadiene in the mixed C5 and the propylene compound are subject to Diels-Alder diene addition reaction at 0-5 DEG C to synthesize coarse product of norbornene derivative, the mixture is subject to vaporization, compression and condensation to obtain cyclopentadiene-removed C5, and the residual liquid is subject to reduced pressure distillation to obtain the target product. The invention has the advantages that the class of norbornene derivative is prepared by utilizing inexpensive mixed C5, byproduct during ethylene splitting decomposition, as raw material, the yield is high, the cost is low, new chemical raw material cyclopentadiene-removed C5 can be obtained simultaneously, thus strengthening further processing and utilizing of mixed C5 and having great realistic significance.

Description

technical field [0001] The invention relates to a method for producing a class of chemical products, in particular to a method for producing norbornene derivatives by using mixed carbon five, and belongs to the field of organic synthesis. Background technique [0002] Mixed C5 is a by-product in the process of cracking natural gas and petroleum hydrocarbons to prepare ethylene, mainly including isoprene, piperylene and cyclopentadiene. Mixed carbon five is an important raw material for synthetic rubber and resin and various fine chemical products, with abundant resources and low price. With the rapid development of my country's petrochemical industry and the continuous construction of ethylene plants, the amount of mixed C5 by-products is also increasing year by year. At present, most of them are used as fuel, and the benefits are not high. At present, the isoprene, piperylene and cyclopentadiene in industrial mixed C5 are mainly extracted by solvent extraction through a la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/47C07C253/30C07C51/353C07C61/29C07C67/347C07C69/753C07C49/553C07C51/62C07C45/69C07C47/445
Inventor 张海洋杨振强李江涛吕海宽蒋卫鹏韩兆海郭利兵陈淑敏崔富民周铎孙雨安杨瑞娜
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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