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Method for producing cyanoacrylate esters in the presence of transition metal catalysts

A cyanoacrylate, transition metal technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylic acid nitrile and other directions, can solve the problem of undisclosed heterogeneous catalyst application and the like

Inactive Publication Date: 2012-05-23
HENKEL KGAA
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  • Abstract
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Problems solved by technology

[0015] None of the above-mentioned documents disclose the application of heterogeneous catalysts in the transesterification reaction of cyanoacrylates.

Method used

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  • Method for producing cyanoacrylate esters in the presence of transition metal catalysts

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Experimental program
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Embodiment

[0127] substances used

[0128] Tetraisopropyl titanate and methyllithium were purchased from Sigma Aldrich and used without further purification. 1-Decanol was purchased from Merck and used without further purification. Titanium tetrachloride was distilled over copper before use. Silica gel (silica 60, 0.04-0.063 mm, 230-400 mesh, specific surface area 500 m2 / g) was purchased from Macherey-Nagel. Methyl 2-cyanoacrylate [CAS 137-05-3] is commercially available and can be purified by distillation before being used in the process of the present invention.

[0129] 1. Preparation of methyl triisopropyl titanate

[0130] In a 100 ml Schlenk flask at 0°C, TiCl was slowly 4 (1.10ml, 10.0mmol) to Ti(Oi-Pr) in dry diethyl ether (5ml) 4 (8.98ml, 30.0mmol), and the resulting mixture was stirred at 0°C for 10min. After stirring at 22°C for 30 min, dry diethyl ether (15 ml) was added and the mixture was cooled to -40°C. Then dropwise added MeLi(Et 2 1.6M in O, 25.0ml, 40.0mmol) so...

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Abstract

The present invention relates to a method for producing cyanoacrylate esters. The method is substantially based on a transesterification reaction, wherein the transesterification reaction is carried out in the presence of at least one transition metal catalyst that is formed by reacting at least one carrier material comprising hydroxyl groups with at least one transfer metal alkoxide.

Description

technical field [0001] The present invention relates to a process for the preparation of cyanoacrylates. The process is essentially based on transesterification, wherein the transesterification is carried out in the presence of at least one transition metal catalyst by combining at least one hydroxyl-containing support material with at least one Formed by the reaction of transition metal alkoxides. Background technique [0002] Cyanoacrylate-based polymerizable adhesive compositions are widely used in industrial and medical applications because of their ease of use, fast cure, and high strength of the resulting bond. The monomeric form of cyanoacrylates is known to be extremely reactive and to polymerize rapidly in the presence of even trace amounts of polymerization initiators, including moisture contained in the air or present on surfaces . Polymerization is initiated by anion, free radical, zwitterion or ion pair. Once polymerization has started, the cure rate can be ...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/23
CPCC07C253/30C07C255/23
Inventor C·弗里森A·基尔施宁L·库塔布勒
Owner HENKEL KGAA
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