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Method for synthesizing 5-vinyl-2-norbornaene

A synthesis method and a technology for norbornene, which are applied in the field of synthesis of 5-vinyl-2-norbornene, can solve the problems of low selectivity and yield of main products, and achieve strong adaptability, flexible operation, and the realization of tube effect of reaction

Inactive Publication Date: 2005-02-16
吉林市大宇化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the selectivity and yield of the main product are not high

Method used

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  • Method for synthesizing 5-vinyl-2-norbornaene
  • Method for synthesizing 5-vinyl-2-norbornaene
  • Method for synthesizing 5-vinyl-2-norbornaene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 325g BD (purity: 98.636wt%), CPD 310.0g (containing 93.26% CPD, 6.276% DCPD), (BD: CPD = 1.27: 1mol ratio = 1.039: 1wt ratio), 225g toluene and 0.5g (about 600ppm) α -Naphthol was added into a 1L autoclave, stirred at a speed of 460 rpm and gradually heated to 154-155°C, and reacted for 3 hours at 2.1Mpa. After the reaction was completed, the mixture was cooled with cooling water to obtain 825 g of the reaction solution. Cool the reactor bladder to -20°C in a freezer. Sampling is carried out chromatographic analysis, and its result is as follows:

[0035] The product composition is: BD: 5.511wt% = 44.64g; CPD: 6.178wt% = 50.05g; VCH: 9.32wt% = 75.49g; VNB: 17.669wt% = 143.12g; Toluene: 24.083wt% = 195.07g; COD : 0.466wt% = 3.775g; THI: 5.751wt% = 46.58g; DCPD: 30.085wt% = 243.69g.

[0036] CPD conversion = 93.7wt% = 93.31mol%

[0037] VNB selectivity = 60.19wt% = 33.10mol%

[0038] VNB yield = 50.40wt% = 30.89mol%

Embodiment 2

[0040] 300g BD (purity: 98.636wt%), CPD 315.0g (containing 90.2% CPD, 8.0% DCPD), (BD: CPD = 1.081: 1mol ratio = 0.956: 1wt ratio), 225g toluene and 0.5g (about 600ppm) α -Naphthol was added to a 1L autoclave, stirred for 5 minutes before the reaction, then stopped stirring, heated up to 154-155°C, and reacted at 2.1Mpa for 3 hours. After the reaction was completed, cooled with cooling water to obtain 825g of the reaction solution. Put the reactor bladder into the freezer to cool to -20°C. Sampling and chromatographic analysis, the results are as follows:

[0041]The product composition is: BD: 5.511%=44.64g; CPD: 6.178wt%=50.04g; VCH: 9.32wt%=75.49g; VNB: 17.669wt%=143.12g; Toluene: 24.083wt%=195.07g; COD: 0.466 wt% = 3.775g; THI: 5.751 wt% = 46.58g; DCPD: 35.085 wt% = 243.69g.

[0042] CPD conversion rate = 82.84wt% = 82.80mol%

[0043] VNB selectivity = 59.22wt% = 32.23mol%

[0044] VNB yield = 49.03wt% = 26.90mol%

Embodiment 3

[0046] 300g BD (purity: 98.636wt%), CPD 315.0g (containing 92.6% CPD, 4.6% DCPD), (BD: CPD = 1.27: 1mol ratio = 1.039: 1wt ratio), 225g toluene and 0.5g (about 600ppm) α -Naphthol was added to a 1L autoclave, stirred for 5 minutes before the reaction, then stopped stirring, and gradually heated up to 154-155°C, and reacted for 1 hour at 2.1Mpa. After the reaction was completed, the mixture was cooled with cooling water to obtain 825 g of the reaction solution. Cool the reactor bladder to -20°C in a freezer. Sampling is carried out chromatographic analysis, and its result is as follows:

[0047] The product composition is: BD: 9.429%=12.75g; CPD: 6.406wt%=34.3g; VCH: 5.845wt%=43.39g; VNB: 14.984wt%=126.6g; Toluene: 24.083wt%=195.07g; COD: 0.466wt% = 3.775g; THI: 2.688wt% = 22.71g; DCPD: 35.063wt% = 296.28g.

[0048] CPD conversion rate = 87.92wt% = 87.90mol%

[0049] VNB selectivity = 50.7wt% = 27.91mol%

[0050] VNB yield=44.57wt%=mol%=24.53mol%

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Abstract

The invention refers to the synthesizing method of 5-ethylene-2-norborene. The mol ratio of the butadiene and cyclopentadiene is 1-2:1. The invention chooses toluene or normal hexane as the solvent and the weight ratio of the reactants added to the solvent is between 20% and 30%. It chooses alpha-naphthol as the inhibitor and its dosage is between 50ppm and 3000ppm of the reactants. We put the material into the reaction kettle, increase the temperature when or after whisking and make them reacting for between 0.25 hour and 4 hours at the temperature of between 130deg.C and 160deg.C and at the pressure of between 1MPa and 8MPa. Or after being mixed we put the material into the reaction kettle or the tubular reactor and stay for between 0.25 hour and 1.0 hour at the temperature of between 130deg.C and 160deg.C and at the pressure of 1.8MPa. The weight ration of the dicyclopentadiene in the material of cyclopentadiene is less than between 5% and 8%. The invention obviously increases the yield of the turnoff by over 5mol%.

Description

technical field [0001] The invention introduces the synthesis method of the key intermediate of the third monomer 5-ethylidene-2-norbornene of ethylene-propylene rubber, and specifically relates to the synthesis method of 5-vinyl-2-norbornene. Background technique [0002] Ethylene Propylene Rubber (EPM) is an elastomer with excellent properties. However, EPM is a kind of saturated rubber, so it cannot be vulcanized, and its mechanical properties are brittle, which limits its application. Later, a vulcanizable ethylene-propylene-non-conjugated two Olefin Terpolymer Rubber (EPDM). Dicyclopentadiene, 1,4-hexadiene, and the like are also used as non-conjugated dienes. But its vulcanization rate is too slow, and the most commonly used non-conjugated diene is ethylidene norbornene (ENB). ENB was first applied for the first patent in 1967 by Union Carbide Corporation of the United States. At present, the company's production capacity has reached a scal...

Claims

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Application Information

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IPC IPC(8): C07C2/50C07C13/43
Inventor 朱众娒李振铎崔昌亿
Owner 吉林市大宇化工有限公司
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