Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-06-16
1999-12-28
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D23332
Patent
active
060083719
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a new and improved process for the production of acrylic or methacrylic acid esters with the formula ##STR1## in which R.sub.1 stands for hydrogen or a methyl group and A and B stand for unbranched or branched alkylene groups with 2 to 5 C atoms.
State of the Art
Compounds of Formula I can be obtained in accordance with the process described in the U.S. Pat. No. 2,871,223, by means of reaction of acrylic or methacrylic acid chloride with hydroxyalkyl imidazolidine-2-ones in the presence of tertiary nitrogen bases, with stoichiometric amounts of the hydrochlorides of the tertiary nitrogen bases being formed, along with other products.
In the process known from EP 0 236 994 A1, for the production of acryl and methacryl esters of Formula I, acrylic or methacrylic acid esters are reacted with 1-(hydroxyalkyl) imidazolidine-2-ones in the presence of titanium alcoholates or chelate compounds of the metals titanium, zirconium, iron, and zinc, with 1,3-dicarbonyl compounds as the re-esterification catalysts.
In EP-A 0 433 135 and EP-A 0 453 638, diorgano tin oxide compounds are claimed as re-esterification catalysts for the re-esterification of acryl and methacryl esters with hydroxyalkyl imidazoline-2-ones.
As a rule, the metal catalyst must be removed from batches after the reaction is complete. This is advantageously done by adding water, for example when using tetraalkyl titanates or dialkyl tin oxides. In this connection, the titanates form metal (hydr)oxides, such as TiO.sub.2, which are removed by filtering or centrifuging them off, for example. These hydrolyzed re-esterification catalysts cannot be used again as such after being removed. It is true that the dialkyl tin oxides can be removed as such by the addition of water, and can be used again as re-esterification catalysts. However, a relatively large amount of water has to be introduced, at first, and this has to be removed from the reaction product once again. According to the German patent application P 42 17 124.5, the reaction can also be carried out in the presence of mixtures of alkali/earth alkali metal compounds, which are essentially used as oxides, hydroxides, carbonates, and/or as salts of carboxylic acids. The alkali/earth alkali compounds present as catalysts can be removed without adding water. The amount of catalytically active compound mixtures is 0.01-10 wt.-%, with reference to the reaction mixture. In spite of the advantageously high reaction speed which is achieved with alkali/earth alkali catalysts, these systems stagnate after approximately 80% hydroxyalkyl imidazolidine-2-one conversion, so that the residual alcohol content in the reaction mixture is relatively high.
Also, the formation of N-(methacryloyl oxyethyl)-N'-(methacryloyl) ethylene urea, a bifunctional methacryl compound, which therefore has a cross-linking effect during polymerization reactions, is very high, at approximately 10% of the re-esterification compounds, and must be improved to be at lower proportions.
DE-OS 3013927 (BASF) describes a polymer-analog reaction with approximately 100,000 ppm calcium hydroxide as the catalyst.
DE 2238208 describes the re-esterification of bactericide quinoxaline derivatives with calcium hydroxide or barium hydroxide catalysis.
Task and Solution
The invention was based on the task of finding a catalytic process for the production of acrylic or methacrylic acid esters of Formula I by alcoholysis of (meth)acrylic acid alkyl esters with hydroxyalkyl imidazolidine-2-ones, which proceeds at a good reaction speed even in the region of final re-esterification, and in which the catalyst used can be removed from the reaction mixture without adding water and used again as such, if necessary. It was now found that the reaction can be carried out in surprisingly advantageous manner with calcium hydroxide, in an amount of less than 250 ppm, with reference to the total amount of the reaction mixture.
The invention relates to a process for the production of (meth)acryl esters of the formu
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Knebel Joachim
Merbach Ralf
Higel Floyd D.
Roehm GmbH
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