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Method of preparing exo-dicyclopentadiene from endo-dicyclopentadiene or cyclopentadiene

A technology of dicyclopentadiene and cyclopentadiene, which is applied in the field of preparation of hanging dicyclopentadiene, can solve the problems of complex process, low yield and output, and achieve high yield and mild liquid phase reaction conditions Effect

Inactive Publication Date: 2008-03-12
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The literature [An improved procedure for the preparation of exo-dicyclopentadiene.Synthesis 1975, 105-106] uses bridged dicyclopentadiene as a raw material to prepare hanging DCPD through a two-step method of HBr addition and HBr removal, but the process is complicated
The literature [The endo to exo isomerisation of dicyclopentadiene. Acta ChemicaScandinavica 1990, 44: 860-861] uses aluminosilicate loaded with precious metal platinum as a catalyst to isomerize low-concentration bridging DCPD gas into pendant dicyclopentadiene, but Lower yield and yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] 100g of bridged dicyclopentadiene is added to 200g of decahydronaphthalene, and 50ppm of p-tert-butylcatechol is added to the solution. In a fixed bed reactor, the temperature is 150°C and the pressure is 4.0MPa The conditions of reaction 2min, 5min, 10min and 30min respectively, the conversion rate of bridged dicyclopentadiene, the selectivity and yield of hanging dicyclopentadiene are shown in the following table:

[0011] Reaction time

Embodiment 2

[0013] Add 200g of bridged dicyclopentadiene to 200g of benzene, and add 2,5-di-tert-butylhydroquinone with a mass content of 300ppm to the solution, at a temperature of 100°C and a pressure of 2.0MPa After reacting for 3 minutes, the conversion rate of bridge dicyclopentadiene was 15.2%, the selectivity of hanging dicyclopentadiene was 76.4%, and the yield was 11.6%. Alkenes 23.2g.

Embodiment 3

[0015] 100g cyclopentadiene is added in 1000g toluene, and temperature is 190 ℃, the reaction is 7 minutes under the condition of pressure 6.0MPa, and the conversion rate of cyclopentadiene is 95.1%, and the selectivity of hanging type dicyclopentadiene is 91.6%, the yield is 87.2%.

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Abstract

The invention discloses a preparation method for exo-dicyclopentadiene from bridge-type dicyclopentadiene or cyclopentadiene, belonging to the exo-dicyclopentadiene preparation technology. The method includes preparing a solution composed of bridge-type dicyclopentadiene or cyclopentadiene, and benzene, or toluene, or benzyl alcohol, or decalin, or cyclohexane, or heptane, or hexane at a certain quality ratio, adding p-tert-butylcatechol, or 2, 5-di-tert-butylhydroquinone, or 2,6-di-tertbutyl-4-methylphenol, or hydroquinone, or 2-methyl-1,4-dihydroxybenzene, or o-hydroquinone inhibitor and carrying out reaction at a certain temperature and pressure, distilling and separating to obtain the exo-dicyclopentadiene. The invention has the advantages of one-step synthesis without catalyst, mild reaction conditions and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing hanging dicyclopentadiene from bridged dicyclopentadiene or cyclopentadiene, which belongs to the preparation technology of hanging dicyclopentadiene. Background technique [0002] Dicyclopentadiene (DCPD) is an important chemical intermediate, generally produced by C in petrochemical 5 The product - cyclopentadiene (CPD) is formed by dimerization at room temperature. DCPD is a raw material or intermediate for the synthesis of a series of high-performance chemicals, including petroleum resins, unsaturated polyesters, ethylene-propylene rubber, reaction injection molding, coating resins and other high-molecular polymers, high-energy materials used in missiles, aircraft, racing cars, etc. Density fuel, as well as synthetic spices, pharmaceutical intermediates, etc. There are two main configurations of DCPD, the bridge configuration accounts for about 95.5%, and the hanging configuration accounts for about...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/61C07C5/25
Inventor 邹吉军姜凯张香文王莅米镇涛
Owner TIANJIN UNIV
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