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Method for preparing keto-functionalized aromatic (METH)acrylates

A keto-functional, acrylate technology is applied in the field of preparing keto-functionalized aromatic acrylates to achieve the effects of reducing the amount of by-products and increasing the conversion rate

Pending Publication Date: 2021-01-05
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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  • Method for preparing keto-functionalized aromatic (METH)acrylates
  • Method for preparing keto-functionalized aromatic (METH)acrylates
  • Method for preparing keto-functionalized aromatic (METH)acrylates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123]

[0124] Apparatus: 2-liter, four-necked, round-bottomed flask with mechanical stirrer, reflux condenser, Pt100 temperature sensor, gas inlet, and electrically heated oil bath.

[0125] mixture:

[0126] 1.51 moles 4-hydroxybenzophenone, 99.8%: 300g

[0127] 1.70 mol MAAH (purity 98.48% (GC), methacrylic acid acetic anhydride 1.131%, no acetic anhydride detected; stabilized with 1871 ppm 2,4-dimethyl-6-tert-butylphenol): 262.8 g

[0128] 1.80 moles of MMA: 180 g

[0129] 0.0087 moles of concentrated sulfuric acid: 0.846g

[0130] Total stabilizer content at the start of the reaction: 1639 ppm based on 4-hydroxybenzophenone.

[0131] Neutralize the catalyst acid with 1.57 g (50% strength) aqueous sodium hydroxide solution

[0132] Excess methacrylic anhydride was esterified with 9.7 g methanol (0.3 moles)

[0133] To prepare a 30% strength solution in MMA: 600 g MMA

[0134] Theoretical yield: 1354g

[0135] process:

[0136] The mixture was weighed out comple...

Embodiment 2

[0143]

[0144] Apparatus: 2-liter, four-necked, round-bottomed flask with mechanical stirrer, reflux condenser, Pt100 temperature sensor, gas inlet, and electrically heated oil bath.

[0145] mixture:

[0146] 1.51 moles 4-hydroxybenzophenone, 99.7%: 300g

[0147] 1.70 mol MAAH (purity 98.59% (GC), methacrylic acid acetic anhydride 0.40%, no acetic anhydride detected; stabilized with 2070 ppm 2,4-dimethyl-6-tert-butylphenol): 262.8 g

[0148] 1.80 moles of MMA: 180 g

[0149] 0.0087 moles of concentrated sulfuric acid: 0.846g

[0150] Total stabilizer content at the start of the reaction: 1813 ppm based on 4-hydroxybenzophenone.

[0151] Neutralize the catalyst acid with 1.8 g of aqueous sodium hydroxide dissolved in 10 g of water

[0152] Excess methacrylic anhydride was esterified with 22.4 g methanol

[0153] Theoretical yield: 1354g

[0154] process:

[0155] The mixture was weighed out completely and then heated to 90°C with stirring and introduction of air. The...

Embodiment 3

[0161]

[0162] Apparatus: 2-liter, four-necked, round-bottomed flask with mechanical stirrer, reflux condenser, Pt100 temperature sensor, gas inlet, and electrically heated oil bath.

[0163] mixture:

[0164] 1.51 moles 4-hydroxybenzophenone, 99.7%: 300g

[0165] 1.70 mol MAAH (purity 98.59% (GC), methacrylic acid acetic anhydride 0.40%, no acetic anhydride detected; stabilized with 2070 ppm 2,4-dimethyl-6-tert-butylphenol): 262.8 g

[0166] 1.80 moles of MMA: 180 g

[0167] 0.0087 moles of concentrated sulfuric acid: 0.846g

[0168] Total stabilizer content at the start of the reaction: 1813 ppm based on 4-hydroxybenzophenone.

[0169] Neutralize the catalyst acid with 1.8 g of aqueous sodium hydroxide dissolved in 10 g of water

[0170] Excess methacrylic anhydride was esterified with 22.4 g methanol

[0171] Theoretical yield: 402.1g

[0172] process:

[0173] The mixture was weighed out completely and then heated to 90°C with stirring and introduction of air. ...

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Abstract

The invention relates to a method for preparing keto-functionalized aromatic (meth)acrylates by reacting keto-functionalized aromatic alcohols or keto-functionalized aromatic amines with (meth)acrylicanhydride having a content of (meth)acrylic acetic anhydride of less than 4.5%.

Description

technical field [0001] The present invention relates to a process for the preparation of keto-functionalized aromatic (meth)acrylates. Background technique [0002] The prior art contains a process for the preparation of [(meth)acryloyloxy]benzophenone starting from (meth)acrylic anhydride (JP2003261506, Mitsubishi Rayon). Triethylamine is used as catalyst and reagent. Since the amine forms a salt with the methacrylic acid formed during the reaction, it is necessary to make the amine and hydroxybenzophenone equimolar. Accordingly, an equimolar amount of salt is obtained and must be disposed of as waste. Therefore, the economics of the process is poor. Furthermore, the work was carried out at very mild temperatures (30°C), which, despite the high catalyst usage, resulted in long reaction times of more than 5 hours. Therefore, this method is also disadvantageous in view of the space-time yield. [0003] In the more recent application WO2017 / 146444, the enzymatic reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/54C07C231/02C07C233/33
CPCC07C67/08C07C231/02C08F220/14C07C69/54C07C69/653C07C233/33C08F220/06C08F220/302
Inventor T·布莱斯S·克里尔T·舒茨D·萨尔M·特雷斯科
Owner EVONIK OPERATIONS GMBH