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Method for producing methacrylated benzophenones

A technology of hydroxybenzophenone and benzophenone, which is applied in the field of preparation of methacrylated benzophenone, to achieve the effect of reducing the amount of by-products and high conversion rate

Active Publication Date: 2014-06-11
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Also, only dry, non-nucleophilic solvents should be used

Method used

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  • Method for producing methacrylated benzophenones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Apparatus: 4 liter four-neck round bottom flask with mechanical stirrer, reflux condenser, Pt100 temperature sensor, air introduction tube, Anschütz attachment, dropping funnel, electrically heated oil bath

[0024] Batch:

[0025] 3.5mol of 4-hydroxybenzophenone, 99.7%: 695.9g

[0026] 3.85 mol of methacrylic anhydride (stabilized with 2,4-dimethyl-6-tert-butylphenol at 2000 ppm): 618.4 g

[0027] 0.020mol concentrated sulfuric acid: 1.99g

[0028] 1864 mg of hydroquinone monomethyl ether

[0029] 932 mg of 2,4-dimethyl-6-tert-butylphenol

[0030] The catalyst acid was neutralized with a solution of 1.8 g sodium hydroxide dissolved in 10 g water

[0031] Esterification of excess methacrylic anhydride with 22.4 g of methanol

[0032] Theoretical yield: 930.0g

[0033] Implementation process:

[0034] The batch was weighed out completely and then heated to 90°C with stirring and introduction of air. Reaction time at 90°C: 6h. It was then cooled to a...

Embodiment 2

[0046] Apparatus: 4 liter four-neck round bottom flask with mechanical stirrer, reflux condenser, Pt100 temperature sensor, air introduction tube, Anschütz attachment, dropping funnel, electrically heated oil bath

[0047] Batch:

[0048] 1.5mol of 4-hydroxybenzophenone: 303g

[0049] 1.65 mol of methacrylic anhydride (stabilized with 2000 ppm of 2,4-dimethyl-6-tert-butylphenol): 262 g

[0050] 0.0087mol of concentrated sulfuric acid: 0.84g

[0051] 798mg of hydroquinone monomethyl ether

[0052] 399 mg of 2,4-dimethyl-6-tert-butylphenol

[0053] Implementation process:

[0054] The batch was weighed out completely and then heated to 90° C. with stirring and introduction of air. Reaction time at 90°C: 6h. It was then cooled to about 60° C. and sodium hydroxide dissolved in water was added to neutralize the catalyst sulfuric acid, and methanol to esterify unreacted methacrylic anhydride. The batch was subsequently stirred at 60° C. for 1 h, and then the batch was mixed ...

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Abstract

The invention relates to a method for producing methacrylated benzophenones and to the uses thereof.

Description

technical field [0001] The present invention relates to a process for the preparation of methacrylated benzophenones and their use. Background technique [0002] The (meth)acrylic anhydride method for the preparation of the above esters is described in the prior art (JP2003261506, Mitsubishi Rayon). Triethylamine was used as catalyst. Since this amine forms a salt with methacrylic acid produced in the reaction, it must be made equimolar with respect to benzophenone. Accordingly, an equimolar amount of salt is obtained, which has to be disposed of as waste. Therefore, this method is low economical. [0003] Other methods of the prior art are the reaction of methacryloyl chloride with hydroxy-functional benzophenones, and the reaction of this material with glycidyl methacrylate. When considering methacryloyl chloride, attention must be paid to corrosion and erosion properties. Additionally, when in contact with water, HCl is liberated. [0004] DE 1720603 describes a pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/08C07C69/54
CPCC07C67/08C07C69/54C07C67/62
Inventor J·克内贝尔W·克莱西C·M·布雷纳G·施密特
Owner EVONIK OPERATIONS GMBH