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Synthetic method for dicyclopentadiene ethoxy methacrylate

A technology of dicyclopentadienyl oxyethyl acrylate and dicyclopentadiene, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problem of low curing shrinkage, low adhesion, unpleasant smell, etc. problems, to achieve the effect of reducing production costs, easy operation and simple steps

Inactive Publication Date: 2016-10-26
山东瑞博龙化工科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] There are two polymerizable groups in the molecular structure of dicyclopentadienyl (meth)acrylate, namely the double bond on the acrylic acid and the allyl group on the polyalicyclic ring. The former can make the monomer undergo free radical polymerization, and the latter The monomer can be oxidatively polymerized similar to drying oil in air, and the corresponding polymer has the characteristics of low curing shrinkage, high adhesion and good thermal stability, so it is a kind of high molecular monomer with excellent performance. It has a wide range of applications in coatings, inks, adhesives and other industries, but its disadvantage is that it has a special, unpleasant smell

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] In a 500 ml reaction flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel, 151 grams (1.3 moles) of hydroxyethyl acrylate, 3 grams of trifluoromethanesulfonic acid and 0.9 grams of phenothiazine were added. Stir to mix the reactants well. Heat to 75°C, slowly add 132 g (1 mole) of dicyclopentadiene dropwise, maintain the temperature at 75-80°C during the dropwise addition, continue the reaction at this temperature after the dropwise addition, and monitor the reaction progress by gas chromatography. After 6 hours of reaction, the content of dicyclopentadiene dropped to 1.5%, stop the reaction, cool, wash with 80 grams of saturated brine three times, separate the organic phase, and then carry out rectification under reduced pressure to collect the fraction at 105-113°C / 130Pa 162 g of dicyclopentadienyloxyethyl acrylate was obtained with a purity of 94.6%. 1H NMR (CDCl3) 6.12 (multiplet, 1H, H2C=C, trans), 5.70 (multiplet, 1H, H2C=C, cis), 5.50 ...

Embodiment 2

[0012] In a 500 ml reaction flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel, add 151 grams (1.3 moles) of hydroxyethyl acrylate, 3 grams of boron trifluoride etherate, 0.3 grams of phenothiazine and 0.6 grams of hydroquinone. Stir to mix the reactants well. Heat to 80°C, slowly add 132 g (1 mole) of dicyclopentadiene dropwise, maintain the temperature at 80-90°C during the dropwise addition, continue the reaction at this temperature after the dropwise addition, and monitor the reaction progress by gas chromatography. After 6 hours of reaction, the content of dicyclopentadiene dropped to 2.1%, stop the reaction, cool, wash with 80 grams of saturated brine three times, separate the organic phase, and then carry out rectification under reduced pressure to collect the fraction at 105~113℃ / 130Pa 149 g of dicyclopentadienyloxyethyl acrylate was obtained with a purity of 93.1%.

Embodiment 3

[0014] This embodiment is an industrial scale-up experiment of Embodiment 2. Add 755 kilograms of hydroxyethyl acrylate, 15 kilograms of boron trifluoride etherate, and 4.5 kilograms of compound inhibitors (mixed by phenothiazine and hydroquinone in a weight ratio of 1:2) in a 2-liter reactor. made). Start stirring, heat up, and when the temperature in the reactor rises to 77-82°C, slowly add 660 kg of dicyclopentadiene through the metering tank (the addition time is about 3 hours), and maintain the temperature of the reaction solution at 80-90°C during the addition process. °C, after the addition, maintain 80-90 °C to continue the reaction, and use gas chromatography to monitor the composition changes of the reaction solution. After 6 hours of reaction, the content of dicyclopentadiene was measured to be 1.9%. Stop heating, and turn on the coil inside the kettle to cool down. After the temperature of the reaction liquid in the kettle was lowered to 25-30°C, 400 kg of satur...

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Abstract

The invention relates to a simple synthetic method for dicyclopentadiene ethoxy methacrylate. The synthetic method is characterized in that in the presence of an appropriate catalyst and polymerization inhibitor, addition reaction of hydroxyethyl methacrylate and dicyclopentadiene is used for synthesizing dicyclopentadiene ethoxy methacrylate. The catalyst is strong acid or super acid and includes boron trifluoride diethyl etherate, chlorosulfonic acid, fluorosulfuric acid, trifluoro sulfoacid, polyphosphoric acid, phosphotungstic acid and silicotungstic acid. The polymerization inhibitor is one of or a combination of phenothiazine, hydroquinone, p-benzoquinone, p-hydroxyanisole, 2-tert-butyl-hydroquinone, 2,5-di-tert-butylhydroquinone, dibutyl dithiocarbamic acid and 2,2,6,6-tetramethyl-4-hydroxy-piperidine nitroxide free radical, wherein the combination is formed by two components mentioned above.

Description

technical field [0001] The present invention relates to a simple and convenient synthesis method of dicyclopentadienyloxyethyl (meth)acrylate, in particular, relates to an electrophilic addition method utilizing (meth)hydroxyethyl acrylate and dicyclopentadiene A method for synthesizing dicyclopentadienyloxyethyl (meth)acrylate by reaction. Background technique [0002] There are two polymerizable groups in the molecular structure of dicyclopentadienyl (meth)acrylate, namely the double bond on the acrylic acid and the allyl group on the polyalicyclic ring. The former can make the monomer undergo free radical polymerization, and the latter The monomer can be oxidatively polymerized similar to drying oil in air, and the corresponding polymer has the characteristics of low curing shrinkage, high adhesion and good thermal stability, so it is a kind of high molecular monomer with excellent performance. It is widely used in coatings, inks, adhesives and other industries, but its ...

Claims

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Application Information

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IPC IPC(8): C07C67/04C07C69/54
CPCC07C67/04
Inventor 刘芳国凤玲赵士燕郑万强
Owner 山东瑞博龙化工科技股份有限公司
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