Preparation method of 1, 3-diallyl-5-ethylene oxide methyl-[1, 3, 5] triazine-2, 4, 6-triketone
By optimizing the catalyst and solvent system, a two-step method was adopted to synthesize 1,3-diallyl-5-epoxymethyl-[1,3,5]triazine-2,4,6-trione, which solved the purity and stability problems in the existing technology and achieved the preparation of the target product with high purity and high yield, which is suitable for the field of electronic chemistry.
Patent Information
- Application Number
- CN202411092382.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-08-09
- Publication Date
- 2026-02-10
AI Technical Summary
Existing technologies make it difficult to prepare 1,3-diallyl-5-epoxymethyl-[1,3,5]triazine-2,4,6-trione with purity that meets the requirements of the field of electronic chemistry, and existing catalysts and solvent systems have stability and efficiency issues.
Using sodium isocyanurate, allyl chloride, and epichlorohydrin as raw materials, diallyl isocyanurate intermediates are synthesized through a two-step reaction. Potassium bromide, iodine bromide, or sodium iodide are used as catalysts, and α-cyclodextrin paste is used as a co-catalyst. The reaction is carried out in acetonitrile solvent. In the second step, DBU is used as an acid scavenger. The purification steps are optimized to improve purity.
The goal was achieved that the purity of the target product reached 99.5% and the yield reached over 80%, meeting the high purity requirements of the electronic chemistry field, reducing production costs and improving the stability and catalytic efficiency of raw materials.
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Figure CN121494834A_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of electronic chemistry and relates to a method for preparing a precursor of a photosensitive resin coating raw material, particularly a method for preparing 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione. Background Technology
[0002] Digital image forming technology (CTP) is a conventional technique in letterpress and flexographic printing. Specifically, it involves creating an image mask on the mask layer of a photosensitive resin printing plate using digital data, followed by irradiating the photosensitive resin layer with active light through the image mask, causing partial photocuring and forming a raised or recessed pattern. This technique requires coating the photosensitive resin printing plate with a photosensitive resin composition containing an organosilicon backbone, a photoacid generator, and a peroxide to form a photosensitive resin coating. The target product prepared in this invention, 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione (structure shown in structural formula A), is one of the precursors for preparing polymers containing an organosilicon backbone and can participate in the synthesis reaction of organosilicon backbone polymers.
[0003] Structural Formula A: Structural formula B:
[0004] Structural formula C: Structural formula D:
[0005] Because the preparation process of the target product of this invention is rarely reported, the preparation methods of other products with similar structures can be referenced during the research and development process. Among them, diglycidyl isocyanurate (see structural formula B) or triglycidyl isocyanurate (see structural formula C), which have similar structures to the target product, are often used as curing agents in the field of coating preparation, and the preparation processes of the above two products have been extensively studied. For example, Chinese invention patent application No. 202210665755.8, entitled "A Preparation Method of Coating Curing Agent and Its Application", prepares the curing agent through a two-step method. In the first step, in an organic solvent, isocyanuric acid and allyl chloride are used as raw materials to generate triallyl isocyanurate (see structural formula D) under the action of the alkaline catalyst triethylamine at 50℃~65℃. In the second step, the triallyl isocyanurate is reacted in an aqueous sodium tungstate solution with hydrogen peroxide and an interfacial active catalyst (i.e., a phase transfer catalyst) at 50℃~80℃ for 12h~24h to generate the target product. The target product prepared in this literature is a mixture, intended for use as a coating curing agent, and does not require the preparation of a single pure product with high purity. Furthermore, the allyl chloride used in the first step of the reaction has poor stability in alkaline solutions, and its boiling point is low. At the disclosed reaction temperature, some of the allyl chloride will evaporate from the reaction system due to boiling or decompose under alkaline conditions. Therefore, the first step of the reaction often requires an excess of allyl chloride.
[0006] Similar to the first step of the reaction study, Chinese invention patent application No. 201210344398.1, entitled "A Method for Preparing Triallyl Isocyanurate," also focuses on the same objective. This patent application investigates a method for preparing triallyl isocyanurate (i.e., the aforementioned triallyl isocyanate). Sodium isocyanate and a catalyst are added to a solvent, and allyl chloride is added dropwise at 70℃–105℃ to initiate the reaction. After 4–8 hours of reaction, the mixture is cooled to room temperature, the solid phase is removed by filtration, and the filtrate after solvent recovery is distilled to obtain the triallyl isocyanurate product. The purity of the obtained product reaches over 98%. The catalyst used in the patent application is a catalytic system of copper catalyst and phase transfer catalyst, wherein the phase transfer catalyst is triethylamine, tributylamine, or pyridine; the solvent is a polar aprotic solvent such as N,N-dimethylformamide, dimethyl sulfoxide, N-methylacetamide, or acetonitrile. This reaction reduces the amount of catalyst used and shortens the reaction time. At the same time, due to the reduction in the amount of alkaline, the stability of allyl chloride in the system is improved to some extent, thus reducing the amount of allyl chloride used.
[0007] However, for products used in the field of electronic chemistry, the requirements for product purity are even higher. The reaction route in Chinese invention patent application No. 201610361584.4, entitled "A Method for Preparing Electronic Grade Triglycidyl Isocyanurate," is as follows:
[0008]
[0009] The above reaction prepares electronic-grade triglycidyl isocyanurate through a two-step reaction involving addition and cyclization. According to the literature, the addition of methanol as a co-solvent and the use of methanol as a cyclization solvent allow for the recovery of unreacted epichlorohydrin immediately after the addition reaction. This simplifies the subsequent epichlorohydrin recovery process and avoids side reactions during the cyclization reaction. This method reduces the amount of epichlorohydrin used in existing technologies (the molar ratio of epichlorohydrin to cyanuric acid is 11–17:1) to 4–7:1, significantly improving product performance and reducing epichlorohydrin residue, thus enabling the industrial production of electronic-grade triglycidyl isocyanurate.
[0010] In order to prepare the target product of this invention, in addition to the preparation methods based on the structurally similar products in the prior art, it is also necessary to conduct systematic research on multiple aspects such as selecting a more suitable synthetic route, improving the stability of raw materials during the synthesis process, developing a catalytic system with higher catalytic efficiency, and optimizing subsequent purification steps, so as to prepare the target product 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione with purity that meets the requirements of the field of electronic chemistry. Summary of the Invention
[0011] The purpose of this invention is to prepare the target product 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione with purity meeting the requirements of the field of electronic chemistry. The invention studies various aspects, including the synthetic route, synthetic process, and purification steps.
[0012] The technical solution adopted in this invention provides a method for preparing 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione. The key aspect is that the above preparation method uses sodium isocyanate, allyl chloride, and epichlorohydrin as raw materials, and synthesizes the 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione product through a two-step reaction.
[0013] S1. Preparation of intermediate: Sodium isocyanate and allyl chloride are reacted in a polar aprotic organic solvent in the presence of a catalyst and a co-catalyst. After the first step reaction is completed, the solvent is filtered and evaporated to obtain crude intermediate. The crude intermediate is purified to obtain intermediate, which is diallyl isocyanurate.
[0014] S2. Preparation of the target product: In a polar aprotic organic solvent, the above intermediate undergoes a second reaction with epoxybromopropane under the action of an acid scavenger; after the second reaction is completed, the solvent is removed by rotary evaporation, and the product is washed and dried to obtain a crude product. The above crude product is purified to obtain 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione.
[0015] Preferably, in the above-mentioned S1 step of preparing intermediates, the catalyst is any one of potassium bromide, iodine bromide or sodium iodide, and the co-catalyst is a paste-like α-cyclodextrin.
[0016] Preferably, in the above-mentioned S1 step of preparing intermediates, the polar aprotic organic solvent is acetonitrile, the temperature of the first step reaction is 37℃~42℃, and the reaction time of the first step reaction is 4h~6h.
[0017] Specifically, in step S1 above, the preparation of the intermediate is carried out as follows: 0.5 parts by mass of α-cyclodextrin are added to 1 to 2 parts by water to form a paste-like α-cyclodextrin. 1 part of sodium isocyanate and 0.005 to 0.01 parts by catalyst are added and stirred to obtain a mixture. The mixture is then added to 40 to 60 parts by mass of a polar aprotic organic solvent, and allyl chloride is added dropwise. The system is heated to 37°C to 42°C and stirred to produce a crude intermediate. The mixture is filtered, and the solvent is removed by rotary evaporation. The crude intermediate is then purified by pulping with dichloromethane to obtain the above-mentioned intermediate. The molar ratio of sodium isocyanate to allyl chloride is 1:2.0 to 2.2.
[0018] Furthermore, in the above-mentioned S2 step of preparing the target product, the acid scavenger is DBU, the temperature of the second step reaction is 20℃~40℃, and the reaction time is 2h~6h.
[0019] Furthermore, in step S2 above, the washing and drying process involves: dissolving in dichloromethane, followed by sequential washing with water, acid, and a saturated sodium carbonate solution; separating the liquid to obtain the organic phase; drying with anhydrous sodium sulfate; and then filtration and concentration to obtain the crude product.
[0020] Specifically, in step S2 above, the purification mentioned above refers to separating the crude product from the target product using a chromatography column.
[0021] Optimally, in the above-mentioned S2 step of preparing the target product, the mass ratio of the above-mentioned intermediate, epichlorohydrin and acid scavenger is 1:1.0~1.5:0.8~1.2.
[0022] Compared with the prior art, the present invention has the following advantages:
[0023] This invention designs a synthetic route using sodium isocyanurate, allyl chloride, and epoxybromopropane as raw materials. The route involves a two-step reaction to first prepare the intermediate diallyl isocyanurate, and then prepare the target product 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione. The route is optimized in several aspects, including catalyst and reaction system, to obtain a product with purity suitable for applications in the field of electronic chemistry.
[0024] In fact, the intermediate diallyl isocyanurate is also commercially available, but the commercially available products are not only more expensive, but their purity does not meet the requirements for raw materials (above 99%). Generally, the purity of commercially available diallyl isocyanurate is only around 95%, and it needs to be further purified before it can be used as a raw material, which increases the production cost.
[0025] This invention prepares the intermediate diallyl isocyanurate from sodium isocyanate and allyl chloride as raw materials. Potassium bromide, iodine bromide, or sodium iodide are used as catalysts, and a paste-like α-cyclodextrin is used as a co-catalyst. The intermediate is prepared in an acetonitrile system at approximately 40°C. The paste-like α-cyclodextrin forms a microenvironment of trace aqueous and organic phases within the molecular cavity, accelerating the catalytic action of the catalyst and promoting the reaction between sodium isocyanate and allyl chloride. The salts generated in the reaction are simultaneously adsorbed by the dextrin, which is beneficial for subsequent filtration. The entire reaction system is carried out in a neutral organic solvent environment, which is beneficial for the stability of the raw material allyl chloride and improves the utilization rate of allyl chloride.
[0026] This invention discovers that the intermediate diallyl isocyanurate and epibromopropane undergo a substitution reaction at a relatively low temperature under the action of DBU, with few side reactions, and the resulting crude product is easy to purify. DBU is 1,8-diazabicycloundec-7-ene, a sterically hindered amidine organic base. Its two adjacent nitrogen atoms can act as stable protonation sites, thus exhibiting strong protophilicity but lacking nucleophilicity. In this invention, DBU not only removes hydrogen halides to achieve a substitution reaction at a lower temperature but also reduces the proportion of epibromopropane. The starting materials for this step are all organic compounds, which are fully contacted in acetonitrile, and no phase transfer catalyst is required during the reaction. Attached Figure Description
[0027] Figure 1 This is the NMR spectrum of sample 1 of the present invention.
[0028] Figure 2 This is the high-performance gas chromatogram of sample 1 of the present invention. Detailed Implementation
[0029] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, and not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.
[0030] Unless otherwise specified in the examples, the procedures can be followed according to conventional conditions; unless the manufacturers of the reagents or instruments used are specified, they are all conventional products that can be purchased commercially.
[0031] For ease of description, the following is in parts by weight.
[0032] Example 1
[0033] S1. Preparation of intermediates:
[0034] S1-1. Take 0.5 parts of α-cyclodextrin and add 1.5 parts of purified water to make a paste of α-cyclodextrin. Add 1 part of sodium isocyanate and 0.005 parts of potassium bromide and stir to obtain a mixture.
[0035] S1-2. Add the mixture to 50 parts of acetonitrile, add 0.03 parts of allyl chloride dropwise, heat the system to 40°C, stir and react for 5 hours to produce crude intermediate product;
[0036] S1-3. After the reaction is complete, the product is filtered, the solvent is evaporated, and then purified by slurrying with 50 parts of dichloromethane to obtain intermediate diallyl isocyanurate, denoted as intermediate 1.
[0037] The structural formula is:
[0038] S2. Preparation of the target product:
[0039] S2-1. Take 1 part of intermediate, 1.2 parts of epichlorohydrin and 1.1 parts of acid scavenger DBU, add them to 45 parts of acetonitrile, and stir the reaction system at 30℃ for 4 hours.
[0040] S2-2. After the reaction is complete, the solvent is removed by rotary evaporation, and dichloromethane is added to dissolve the product. The product is then washed with water, acid, and saturated sodium carbonate solution. The organic phase is obtained by separation and dried with anhydrous sodium sulfate. The product is then concentrated by filtration to obtain the crude product. The crude product is purified by column chromatography to obtain 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione, which is designated as sample 1.
[0041] Example 2
[0042] S1. Preparation of intermediates:
[0043] S1-1. Take 0.5 parts of α-cyclodextrin and add 2 parts of purified water to make a paste of α-cyclodextrin. Add 1 part of sodium isocyanate and 0.008 parts of iodine bromide and stir to obtain a mixture.
[0044] S1-2. Add the mixture to 40 parts of acetonitrile, add 0.03 parts of allyl chloride dropwise, heat the system to 37°C, stir and react for 6 hours to produce crude intermediate product;
[0045] S1-3 After the reaction is completed, the solvent is filtered and evaporated, and then purified by slurrying with 45 parts of dichloromethane to obtain intermediate diallyl isocyanurate, which is referred to as intermediate 2.
[0046] S2. Preparation of the target product:
[0047] S2-1. Take 1 part of intermediate, 1.5 parts of epichlorohydrin and 0.8 parts of acid scavenger DBU, add them to 60 parts of acetonitrile, and stir the reaction system at 40℃ for 2 hours.
[0048] S2-2, the same as step S2-2 in Example 1, is used to prepare sample 2.
[0049] Example 3
[0050] S1. Preparation of intermediates:
[0051] S1-1. Take 0.5 parts of α-cyclodextrin and add 1 part of purified water to make a paste of α-cyclodextrin. Add 1 part of sodium isocyanurate and 0.01 parts of sodium iodide and stir to obtain a mixture.
[0052] S1-2. Add the mixture to 60 parts of acetonitrile, add 0.03 parts of allyl chloride dropwise, heat the system to 42°C, stir and react for 5 hours to produce crude intermediate product;
[0053] S1-3 After the reaction is completed, the solvent is filtered and evaporated, and then purified by slurrying with 55 parts of dichloromethane to obtain intermediate diallyl isocyanurate, which is referred to as intermediate 3.
[0054] S2. Preparation of the target product:
[0055] S2-1. Take 1 part of intermediate, 1.0 part of epichlorohydrin and 1.2 parts of acid scavenger DBU, add them to 45 parts of acetonitrile, and stir the reaction system at 20℃ for 6 hours.
[0056] S2-2, the same as step S2-2 in Example 1, is used to prepare sample 3.
[0057] Comparative Example 1
[0058] The implementation method is the same as in Example 1, except that in step S2-1, DBU is not used as an acid scavenger; instead, an equal mass of sodium hydroxide is used. The reaction temperatures are controlled at 30°C, 50°C, and 70°C, respectively. GC is used to monitor the content of the target product, and the point with the highest target product content is taken as the reaction endpoint. In the experiment, it was found that the target product could not be detected at 30°C and 50°C, but the highest target product content was detected at 70°C for 4.5 hours. Reference standard 1 was then prepared through subsequent steps.
[0059] Comparative Example 2
[0060] The implementation method is the same as in Example 1, except that in S1, during the preparation of the intermediate, α-cyclodextrin paste is not used as a co-catalyst; instead, 0.5 parts of N-methylpyridine quaternary ammonium salt are added. The specific preparation steps are as follows:
[0061] Add 1 part sodium isocyanurate, 0.5 parts N-methylpyridine quaternary ammonium salt and 0.005 parts potassium bromide to 50 parts of acetonitrile aqueous solution (acetonitrile and water ratio is 1:1). Add 0.03 parts, 0.05 parts and 0.1 parts allyl chloride dropwise to the system respectively. Heat the system to 40°C and stir the reaction for 5 hours.
[0062] After the reaction was completed, the mixture was filtered, extracted, separated, and the organic phase was retained. The solvent was evaporated to obtain the crude intermediate. The crude intermediate was then purified by slurrying with 80 parts of dichloromethane to obtain intermediate control diallyl isocyanurate, which were designated as intermediate controls 1, 2 and 3.
[0063] The intermediate control 1 was used for the subsequent preparation process, and the specific steps were the same as step S2 of Example 1, to prepare control products 2-1, 2-2 and 2-3 respectively.
[0064] Analysis and Testing
[0065] The samples prepared in this invention were analyzed by 1H NMR and HPLC-MS / MS, confirming that the structure of the obtained samples conforms to the characteristics of 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione. Some of the analytical spectra are shown in the appendix. Figure 1 .
[0066] The purity of intermediates, samples, intermediate controls, and reference standards was determined using high-performance gas chromatography (HPLC), and the yield was calculated using the following formula. The results are shown in Table 1, and some test chromatograms are attached. Figure 2 .
[0067] The yield calculation formula is:
[0068] Intermediate yield = Actual weight (g) of the obtained intermediate or intermediate control / Theoretical yield (g) calculated based on the amount of sodium isocyanurate used × 100%;
[0069] Product yield = Actual weight of the obtained sample or reference standard (g) / Theoretical yield (g) calculated based on the amount of diallyl isocyanurate used × 100%;
[0070] Overall yield = intermediate yield × product yield.
[0071] Table 1: Summary of Purity and Yield Results
[0072]
[0073] As can be seen from the results in Table 1, the present invention uses a two-step method to prepare the target product with a total yield of over 80%. More importantly, the purity of the prepared target product can reach about 99.5%, which meets the requirements of the electronic chemistry field for high purity of raw materials.
[0074] Based on the results of Comparative Example 1, it was found that changing the acid scavenger, such as sodium hydroxide, required a higher reaction temperature, resulted in more byproducts, and led to a very low yield of only 56.7% in the second step. This hindered subsequent purification processes, and the purity of the obtained reference standard was only 97.6%. Therefore, in this reaction, DBU showed better stability in the reaction system and higher catalytic activity compared to other commonly used acid scavengers, accelerating the reaction and lowering the required temperature. In this study, potassium hydroxide, potassium carbonate, sodium carbonate, sodium bicarbonate, and other basic or alkaline inorganic salts were also used as acid scavengers, and the findings were similar to those in Comparative Example 1.
[0075] According to the results of Comparative Example 2, instead of using paste-like α-cyclodextrin, a conventional quaternary ammonium salt phase transfer catalyst was used as a co-catalyst, requiring an aqueous acetonitrile solution as the reaction system. Moreover, as the amount of allyl chloride increased, the yield of the intermediate gradually increased, indicating that allyl chloride had a significant degradation problem in the comparative example system.
[0076] Furthermore, the study found that replacing other polar aprotic solvents, such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methylacetamide, did not yield the same results as acetonitrile. This was particularly true for the first reaction step, because acetonitrile itself is neutral, while other polar aprotic solvents are weakly basic. Since no other basic catalyst was added in the first reaction step of this invention, the entire system remained in a neutral state, resulting in greater stability and higher utilization of allyl chloride.
[0077] While some literature mentions acetonitrile as a reaction solvent in existing technologies, acetonitrile has a low boiling point, making it difficult to lower the reaction temperature below it. This leads to boiling of the reaction system, excessive pressure in the reactor, and difficulty in controlling the reaction progress, making acetonitrile unsuitable for practical industrial production. Because this invention uses a suitable catalyst, both reaction steps are completed at lower temperatures, thus avoiding boiling issues when using acetonitrile as a solvent. Furthermore, the low-boiling-point acetonitrile can be evaporated at a lower temperature after the reaction, significantly saving energy.
[0078] When used in the manufacture of highly integrated and high-performance electronic components such as next-generation semiconductor substrates and PCBs, this product provides composite materials with improved heat resistance and thermal expansion properties, as well as excellent hardenability. This ensures the design, processability, and reliability of highly integrated, miniaturized, flexible, and high-performance components in the manufacturing of next-generation integrated circuit substrates, printed circuit boards, packaging, organic thin-film transistors, and flexible display substrates. This is because, in addition to the chemical bonds between alkoxy groups and the curing agent, this product exhibits enhanced heat resistance and thermal expansion properties due to the chemical bonds between alkoxy-silicon groups and between alkoxy groups and the curing agent. This product also possesses excellent strength; when applied to metal films, it exhibits excellent adhesion to the metal film surface through chemical bonding with the alkoxy groups, thus eliminating the need for a silane coupling agent.
Claims
A method for preparing 1,1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione, characterized in that, The preparation method described above uses sodium isocyanurate, allyl chloride, and epichlorohydrin as raw materials to synthesize 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione product through a two-step reaction: S1. Preparation of intermediate: Sodium isocyanate and allyl chloride are reacted in a polar aprotic organic solvent under the action of a catalyst and a co-catalyst. After the first step reaction is completed, the intermediate is obtained by filtration and evaporation of the solvent. The crude intermediate is purified to obtain the intermediate, which is diallyl isocyanate. S2. Preparation of the target product: In a polar aprotic organic solvent, the intermediate undergoes a second reaction with epoxybromopropane under the action of an acid scavenger; after the second reaction is completed, the solvent is removed by rotary evaporation, and the product is washed and dried to obtain a crude product. The crude product is purified to obtain 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione.
2. The method for preparing 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione according to claim 1, characterized in that, In step S1, the preparation of intermediates, the catalyst is any one of potassium bromide, iodine bromide, or sodium iodide, and the co-catalyst is a paste-like α-cyclodextrin.
3. The method for preparing 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione according to claim 1, characterized in that, In step S1, the preparation of intermediates, the polar aprotic organic solvent is acetonitrile, the temperature of the first step reaction is 37℃~42℃, and the reaction time of the first step reaction is 4h~6h.
4. The method for preparing 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione according to claim 2, characterized in that, In step S1, the preparation of the intermediate, the specific operation method is as follows: by mass, take 0.5 parts of α-cyclodextrin and add 1 to 2 parts of water to make a paste of α-cyclodextrin, add 1 part of sodium isocyanate and 0.005 to 0.01 parts of catalyst, stir to obtain a mixture, add the mixture to 40 to 60 parts of polar aprotic organic solvent, add allyl chloride dropwise, heat the system to 37°C to 42°C, stir to react, and generate crude intermediate; filter, remove the solvent by rotary evaporation of the filtrate, and purify the crude intermediate by pulping with dichloromethane to obtain the intermediate; the molar ratio of sodium isocyanate to allyl chloride is 1:2.0 to 2.
2.
5. The method for preparing 1,3-diallyl-5-epoxyethylenemethyl-[1,3,5]triazine-2,4,6-trione according to claim 1, characterized in that, In step S2, the preparation of the target product, the acid scavenger is DBU, the temperature of the second step reaction is 20℃~40℃, and the reaction time is 2h~6h.
6. The method for preparing 1,3-diallyl-5-epoxymethyl-[1,3,5]triazine-2,4,6-trione according to claim 1, characterized in that, In step S2, the washing and drying process of preparing the target product is as follows: dichloromethane is added to dissolve the product, followed by water washing, acid washing, and washing with a saturated sodium carbonate aqueous solution. The organic phase is obtained by separation, dried with anhydrous sodium sulfate, and then concentrated by filtration to obtain the crude product.
7. The method for preparing 1,3-diallyl-5-epoxymethyl-[1,3,5]triazine-2,4,6-trione according to claim 1, characterized in that, In step S2, the purification process refers to separating the crude product using a chromatography column to obtain the final product.
8. The method for preparing 1,3-diallyl-5-epoxymethyl-[1,3,5]triazine-2,4,6-trione according to claim 1, characterized in that, In step S2, the preparation of the target product, the mass ratio of the intermediate, epichlorohydrin, and acid scavenger is 1:1.0-1.5:0.8-1.2.
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