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Method for preparing triallyl isocyanurate

A technology of triallyl isocyanurate and triallyl cyanurate, which is applied in the field of manufacturing triallyl isocyanurate, can solve the problems of promoting the formation of by-products and insufficient conversion rate, so as to avoid Aggregation, potential hazard minimization effect

Inactive Publication Date: 2008-02-20
DEGUSSA AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Another disadvantage of the process described in SU 1121260 is the formation of polymeric products: because the TAIC is kept in the reactor for a long time, the inventors of the present application found that up to 20% by weight of oligomers are formed, which although cannot be Detected in gas chromatography, but produced methanol deposits after distillative removal of solvent
Furthermore, it has also been shown that the use of hydrate-containing copper salts as taught in this Soviet document leads to insufficient conversion, or promotes the formation of by-products

Method used

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  • Method for preparing triallyl isocyanurate

Examples

Experimental program
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Effect test

Embodiment 1

[0044] In a 500-ml capacity double-wall stirred vessel heated with a constant temperature polysiloxane bath adjusted to 130°C, add 25 ml of TAC and 0.3 g of CuCl 2 (without water) in 75 ml of toluene. The temperature inside the flask was adjusted to 113 to 115°C. After 16 minutes, vigorous reflux began and the initially blue solution turned dark gray-green. After the reaction gradually weakened, a metering pump was used to continuously pump 3000 ml of TAC, 3.0 g of CuCl at 10 ml / min. 2 and 3000 ml of toluene. Simultaneously, 10 ml / min of the reaction solution was pumped out using a second metering pump. The reaction temperature rises to about 123 to 125°C.

[0045] If working with an apparatus with a higher TAC concentration (higher space-time yield), the reaction temperature is limited to a maximum of 140° C. by applying a corresponding vacuum.

[0046] The conversion rate is greater than 99.9%. Diallyl isocyanurate is formed as a by-product by TAC and residual water in...

Embodiment 2

[0048] According to the method of Example 1, but using diethyl carbonate as solvent. By mixing TAC with diethyl carbonate at a volume ratio of 1:3, and adding 2.5 g of CuCl 2 / liter of the starting reactant solution and then very finely ground in a wet mill to make the reaction mixture for the starting reaction. Preload 200 ml of the solution, heat to 130 °C and wait for the reaction to start, then pump TAC and diethyl carbonate at a volume ratio of 1:1 and 0.4 g of CuCl at 15 ml / min. 2 / liter of solution composed of a homogeneous dispersion while pumping out 15 ml / min of green TAIC solution. The conversion of TAC was greater than 99.8%. The process step can be maintained without hindrance for a period of 8 hours without loss of yield and purity.

Embodiment 3

[0050] According to the method of Example 1, but after starting the reaction, metered in 1000 ml of TAC and 0.25 g of anhydrous CuCl 2 A very finely dispersed homogeneous mixture of compositions. The metered amount was 10 ml / min; at the same time 10 ml / min of the reaction solution was pumped out. As the amount of toluene in the reaction vessel decreases over time by distilling off the toluene, the operating temperature in the reactor continues to rise. To prevent polymerization, a vacuum was applied at an internal temperature of the flask of 140°C, thereby obtaining a constant working temperature by vapor cooling the TAIC formed. The vacuum required here is 2.0 to 3.0 hPa. The method provides TAIC with a purity of 98.5%; the isomerization rate of TAIC is greater than 99.8%.

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Abstract

The invention relates to an improved method which can be safely implemented for producing triallyl isocyanurate (TAIC) through the rearrangement function and under at least a temperature below 90 DEG C through triallyl cyanurate (AIC) which is catalyzed by Cu2+. According to the invention, TAC and arbitrarily selected Cu2+ catalyst and solvent are added constantly into the original reaction mixture after the beginning of previously inhibited isomerization, and the isomerization is implemented at the temperature of 90-160 DEG C, and an equal amount to the amount of the original reactants of reaction mixture is extracted continuously and purified. The isomerization is implemented in TAIC which is preferentially chosen as a reaction medium.

Description

technical field [0001] The present invention relates to the Cu 2+ Improved process for the manufacture of triallyl isocyanurate (TAIC) by catalyzed rearrangement of triallyl cyanurate (TAC) at least 90°C. Background technique [0002] Triallyl isocyanurate [triallyl-s-triazine-2,4,6(1H,3H,5H)-trione; abbreviated as TAIC] is a trifunctional polymerizable monomer used in As a cross-linking component of advanced thermoplastics and synthetic rubber, and as a raw material for the manufacture of fire retardants. In addition, TAIC is also used as a copolymerization component in the polymerization of vinyl monomers, allyl monomers, and acryl monomers. [0003] TAIC can be manufactured mainly according to three methods: [0004] In the process according to U.S. Patent No. 3,322,761, triallyl isocyanurate (TAIC) is prepared by reacting cyanuric acid with allyl chloride and sodium hydroxide in the presence of copper chloride as a catalyst Got it. The disadvantage of this method is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/34
Inventor 彼得·韦勒汉斯－彼得·克里默曼弗雷德·施密特克劳斯·施塔特米勒马丁·特拉格泽
Owner DEGUSSA AG
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