A pdi catalyst for preparing a cresoltriazole trisiloxane, a preparation method and a preparation method of a cresoltriazole trisiloxane

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By using the iron complex catalyst PDI to replace the platinum catalyst, the problems of high cost and heavy metal residue of platinum catalysts were solved, and the low-cost and high-efficiency preparation of cresoltrazol trisiloxane was achieved, avoiding heavy metal pollution.

CN119751516BActive Publication Date: 2025-11-28NANJING JIEYUN PHARMA TECH CO LTD

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Patent Information

Application Number: CN202411948434.4
Authority / Receiving Office: CN · China
Patent Type: Patents(China)
Current Assignee / Owner
Filing Date: 2024-12-27
Publication Date: 2025-11-28
Estimated Expiration: 2044-12-27

AI Technical Summary

Technical Problem

In existing technologies, the use of platinum catalysts for the preparation of cresoltrazol trisiloxane is costly and carries the risk of heavy metal residues, which limits the optimization of material costs and product quality.

Method used

Iron complex catalyst PDI was used to replace platinum catalyst. The PDI catalyst was prepared by reacting (MePDI)FeBr2, sodium and naphthalene in an ultra-dry solvent. The PDI catalyst was then used in the hydrosilylation reaction of 2-(2'-hydroxy-3'-methallyl-5'-methylphenyl)benzotriazole with bis(trimethylsiloxymethylsilane) to prepare cresoltrazol trisiloxane.

Benefits of technology

This reduces material costs while avoiding the risk of heavy metal residues, achieving higher catalytic activity and selectivity.

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Abstract

The application relates to the technical field of fine chemical synthesis, and discloses a PDI catalyst for preparing cresol trisiloxane, a preparation method and a preparation method of cresol trisiloxane. Me PDI)FeBr2, sodium and nai are dissolved in an ultradry solvent, and the reaction is stirred under a nitrogen atmosphere; the reaction product is post-treated to obtain a PDI catalyst; 2-(2'-hydroxy-3'-methylethenyl-5'-methylphenyl) benzotriazole and the PDI catalyst are dissolved in an organic solvent, the temperature is increased to 50-60 DEG C, bistrimethylsiloxy methylsilane is added dropwise, and the reaction is preserved for 6-10 h; the organic solvent is removed by concentration under reduced pressure, and crystallization is carried out to obtain cresol trisiloxane. The iron complex catalyst is used to replace the traditional platinum catalyst, the material cost is reduced, the risk of heavy metal residue can be avoided, a small amount of the iron complex catalyst can be used, and higher catalytic activity and selectivity can be realized.

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Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of fine chemical synthesis, and particularly relates to a PDI catalyst for preparing methylphenyl triazolyl trisiloxane, a preparation method and a preparation method of methylphenyl triazolyl trisiloxane. BACKGROUND

[0002] Methylphenyl triazolyl trisiloxane is prepared by silicane hydrogen addition of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole.

[0003]

[0004] The silicane hydrogen addition reaction is usually catalyzed by a platinum-containing reagent, such as Karstedt catalyst, chloroplatinic acid, N-heterocyclic carbene platinum complex, polymer platinum complex catalyst, various platinum supported catalysts and the like. Although these catalysts can make the reaction run, due to the high price of platinum, the material cost optimization space of methylphenyl triazolyl trisiloxane is greatly limited. At the same time, platinum is a heavy metal, and the residual platinum also poses a great challenge to the quality of the product.

[0005]

[0006] Therefore, it is necessary to develop a catalyst which can replace the traditional platinum catalyst to catalyze the silicane hydrogen addition, can greatly reduce the material cost, and can avoid the risk of heavy metal residue, which obviously has positive practical significance. SUMMARY

[0007] In view of the above problems existing in the prior art, the present application provides a PDI catalyst for preparing methylphenyl triazolyl trisiloxane, a preparation method and a preparation method of methylphenyl triazolyl trisiloxane, which can reduce the material cost while avoiding the risk of heavy metal residue.

[0008] To solve the above problems, the present application provides the following technical scheme:

[0009] In a first aspect, the present application provides a PDI catalyst for preparing methylphenyl triazolyl trisiloxane, which has a structural formula as shown in formula I:

[0010]

[0011] In the formula, R is methyl or ethyl.

[0012] In a second aspect, the present application provides a preparation method of the PDI catalyst, which comprises the following steps:

[0013] The PDI catalyst is prepared by the following steps: MePDI) FeBr2, sodium and naphthalene are dissolved in super dry solvent, and the reaction is stirred under nitrogen atmosphere, and the reaction product is post-treated to prepare PDI catalyst.

[0014] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole and PDI catalyst is 1:0.001-0.006. Me The molar ratio of PDI) FeBr2, sodium and naphthalene is 40:20:1.

[0015] In one embodiment of the present application, the super dry solvent is selected from one of super dry tetrahydrofuran, super dry methanol, super dry toluene, super dry acetonitrile, super dry acetone, super dry methyl tert-butyl ether.

[0016] In one embodiment of the present application, the super dry solvent is selected from super dry tetrahydrofuran.

[0017] In one embodiment of the present application, the temperature of stirring reaction is 20-30℃, and the time of stirring reaction is 4-6h.

[0018] In one embodiment of the present application, the post-treatment is to concentrate the super dry solvent under reduced pressure, and the residue is dissolved in methyl tert-butyl ether and filtered to remove salt, and concentrated under reduced pressure to not distill.

[0019] In one embodiment of the present application, the super dry solvent is selected from one of super dry tetrahydrofuran, super dry methanol, super dry toluene, super dry acetonitrile, super dry acetone, super dry methyl tert-butyl ether.

[0020] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole and PDI catalyst is 1:0.001-0.006.

[0021] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole and PDI catalyst is 1:0.001-0.006.

[0022] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole and PDI catalyst is 1:0.001-0.006.

[0023] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole and PDI catalyst is 1:0.001-0.006.

[0024] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl) benzotriazole and PDI catalyst is 1:0.001-0.006.

[0025] In one embodiment of the present application, the mass ratio of 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl)benzotriazole and bistrimethylsilyloxymethylsilane is 1:1.04.

[0026] In one embodiment of the present application, the mass ratio of organic solvent and 2-(2'-hydroxy-3'-methylallyl-5'-methylphenyl)benzotriazole is 3:1.

[0027] In one embodiment of the present application, the organic solvent is selected from ethyl acetate.

[0028] Compared with the prior art, the iron complex catalyst is used to replace the conventional platinum catalyst in the present application, the iron series metal is abundant in reserves and cheap and easy to obtain, the material cost can be reduced, and the risk of heavy metal residue can be avoided; and a small amount of iron complex catalyst can achieve higher catalytic activity and selectivity. BRIEF DESCRIPTION OF DRAWINGS

[0029] Figure 1 HPLC spectra of the cresol trisiloxane prepared in Example 2 at detection wavelengths of 305 nm and 342 nm, respectively. 1 HNMR spectra;

[0030] Figure 2 HPLC spectra of the cresol trisiloxane prepared in Example 2 at detection wavelengths of 305 nm and 342 nm, respectively. DETAILED DESCRIPTION

[0031] The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments of the present application.

[0032] The "range" disclosed in the present application is limited in the form of lower limit and upper limit, a given range is limited by selecting a lower limit and an upper limit, and the selected lower limit and upper limit limit the boundary of a particular range. The range limited in this way can include or not include the end value, and can be arbitrarily combined, that is, any lower limit can be combined with any upper limit to form a range.

[0033] Unless otherwise specified, the present application refers to the percentage between liquids as volume / volume percentage; the present application refers to the percentage between liquids and solids as volume / weight percentage; the present application refers to the percentage between solids and liquids as weight / volume percentage; the rest is weight / weight percentage.