Method for preparing diethylhexyl butyramido triazinone by one-pot method

Abstract

The invention discloses a method for preparing diethylhexyl butyrylamide triazinone, which comprises the following steps: S1, in the presence of an organic acid-binding agent, carrying out substitution reaction on N-tert-butyl-4-aminobenzamide and cyanuric chloride in a non-polar solvent at-10 DEG C to 60 DEG C for 1-6 hours to obtain an untreated substitution reaction mixture; and S2, adding isooctyl p-aminobenzoate into the substitution reaction mixture obtained in the step S1, and carrying out a reaction at 15-120 DEG C for 3-15 h so as to finally prepare the diethylhexyl butyramido triazinone. According to the method, the organic acid-binding agent is used, so that the substitution reaction is more stable, byproducts are fewer, and the product purity is higher. Meanwhile, due to the adoption of the organic acid-binding agent, a non-polar solvent can be conveniently used in the step of substitution reaction, so that a substitution reaction mixture can be directly subjected to next-step reaction with isooctyl p-aminobenzoate without treatment, and the one-pot preparation of the diethylhexyl butyrylamide triazinone is realized.

Description

Technical Field

[0001] The invention belongs to the technical field of compound synthesis, and particularly relates to a method for preparing diethylhexyl butyramido triazone by a one-pot process. Background Art

[0002] Triazine UV absorbers are a new type of high-efficiency and broad-spectrum UV absorbers developed in recent years. They have a large molecular structure and high UV absorption efficiency and antioxidant function, and are the development direction of UV absorbers. As a new type of triazine UV absorber, diethylhexyl butyramido triazone has a large molecular structure and high UV absorption efficiency, and has a broad-spectrum sunscreen effect, which can protect against both UVB and UVA UV rays. It is a type of triazine UV absorber currently allowed for use in the European Union, Australia, China and Japan.

[0003] The prior art has reported a compound called diethylhexyl butyramido triazone, and a method for synthesizing the compound is reported:

[0004] First, N-tert-butyl-4-aminobenzamide and cyanuric chloride are reacted in acetone solvent with sodium carbonate as an acid binding agent to synthesize a substituted intermediate N-tert-butyl-4-[(4,6-dichloro-1,3,5-triazine)amino]benzamide (Formula I). ​​The reaction formula of this step is as follows:

[0005]

[0006] Then, the substituted intermediate reacts with isooctyl p-aminobenzoate in xylene under reflux to obtain diethylhexyl butyramido triazone (Formula II), which is then sanded with a toluene / cyclohexane mixed solvent to obtain the product. The reaction formula of this step is as follows:

[0007]

[0008] Another synthesis method of the compound is also reported in the prior art, and the above synthesis route is simply optimized. The synthesis method uses nitriles with 2 to 8 carbon atoms or dialkyl ketones with 2 to 6 carbon atoms as solvents, sodium hydroxide as an acid binding agent to synthesize a substituted intermediate, and the reaction molar ratio of cyanuric chloride to N-tert-butyl-4-amino-benzoyl and sodium hydroxide is 1: (1.05-1.10): (0.2-0.4). In the solvent of n-hexane, cyclohexane, petroleum ether, heptane, benzene, toluene or xylene, the molar ratio of the substituted intermediate to 4-aminobenzoic acid-2-ethylhexyl ester is 1: (2.05-2.20), and the target product is obtained by reflux reaction.

[0009] However, the synthetic methods reported above all have the problem of generating a large number of impurities during the reaction process, which affects the product quality, and the intermediates need to be processed before use, resulting in complicated operations. Summary of the invention

[0010] In view of the above problems, the present invention is proposed to provide a method for preparing diethylhexylbutanamidotriazone which overcomes the above problems or at least partially solves the above problems.

[0011] An object of the present invention is to provide a one-pot method for preparing diethylhexyl butyramido triazone, which can reduce the generation of by-products, improve the purity of the product, and avoid the intermediate processing step.

[0012] A further object of the present invention is to further improve the purity of the product.

[0013] In particular, the present invention provides a method for preparing diethylhexyl butyramido triazone, comprising the following steps:

[0014] Step S1: in the presence of an organic acid-binding agent, subjecting N-tert-butyl-4-aminobenzamide to a substitution reaction with cyanuric chloride in a non-polar solvent at -10°C to 60°C for 1 to 6 hours to obtain an untreated substitution reaction mixture;

[0015] Step S2: adding isooctyl p-aminobenzoate to the substitution reaction mixture obtained in step S1, and reacting at 15° C. to 120° C. for 3 to 15 hours to finally obtain diethylhexyl butyramido triazone.

[0016] Optionally, the organic acid-binding agent is triethylamine, diisopropylethylamine, N,N-dimethylaniline or N,N-diethylaniline.

[0017] Optionally, the non-polar solvent is toluene, xylene, trimethylbenzene, dichloroethane or chloroform.

[0018] Optionally, the molar ratio of N-tert-butyl-4-aminobenzamide, cyanuric chloride and the organic acid-binding agent is 1:(0.95-1.15):(1-1.15).

[0019] Optionally, the molar ratio of isooctyl p-aminobenzoate to N-tert-butyl-4-aminobenzamide is (1.95-2.05):1.

[0020] Optionally, the step S2 further includes:

[0021] After the reaction of isooctyl p-aminobenzoate and the substituted product of step S1 is completed, the reaction product is washed with water and separated into phases, and the solvent in the organic phase obtained by the phase separation is removed to obtain a crude product of diethylhexyl butyramido triazone.

[0022] Optionally, the method for preparing diethylhexyl butyramido triazone further comprises:

[0023] Step S3: adding the crude product to an aqueous organic solvent for extraction and phase separation, dropping the oil layer obtained by phase separation into water for crystallization, filtering and drying the precipitated crystals to obtain a diethylhexyl butyramido triazone product.

[0024] Optionally, the water content of the aqueous organic solvent is 10wt% to 95wt%;

[0025] The extraction temperature is 0-70°C.

[0026] Optionally, the aqueous organic solvent is one selected from the following:

[0027] Tetrahydrofuran aqueous solution, methyltetrahydrofuran aqueous solution, dioxane aqueous solution, methanol aqueous solution, ethanol aqueous solution, propanol aqueous solution, isopropanol aqueous solution, butanol aqueous solution.

[0028] Optionally, the operations of washing and phase separation of the reaction product specifically include:

[0029] After washing the reaction product with water, perform a first phase separation;

[0030] The organic phase obtained by the first phase separation is adjusted to pH 6.0-10.0 using an alkaline aqueous solution, allowed to stand and a second phase separation is performed;

[0031] The organic phase obtained from the second phase separation was washed with water until it became neutral, and then allowed to stand and the third phase separation was performed.

[0032] The method for preparing diethylhexyl butyramido triazone provided by the present invention uses an organic acid-binding agent in the substitution reaction of N-tert-butyl-4-aminobenzamide and cyanuric chloride, so that the substitution reaction is more stable, less by-products, and higher product purity. At the same time, due to the use of the organic acid-binding agent, a non-polar solvent can be conveniently used in the step of the substitution reaction, so that the substitution reaction mixture can be directly reacted with isooctyl p-aminobenzoate without treatment, thereby realizing the one-pot preparation of diethylhexyl butyramido triazone.

[0033] Furthermore, compared with the existing synthesis method, the method for preparing diethylhexyl butyramido triazone provided by the present invention reduces the reaction ratio of isooctyl p-aminobenzoate in the reaction of the substitution reaction mixture with isooctyl p-aminobenzoate, so that the reaction purity is higher under amine salt catalysis, thereby further improving the purity of the diethylhexyl butyramido triazone product.

[0034] Furthermore, in the method for preparing diethylhexyl butyramido triazone provided by the present invention, after the substitution reaction mixture is reacted with isooctyl p-aminobenzoate to obtain a crude diethylhexyl butyramido triazone product, the crude product is subjected to liquid-liquid extraction with an aqueous organic solvent to purify the product, thereby removing most polar impurities and residual salts, thereby obtaining a diethylhexyl butyramido triazone product with a product purity of ≥99.0%.

[0035] The method for preparing diethylhexyl butyramido triazone provided by the invention has a simple process route, few equipment requirements, convenient operation, high product purity, low production cost, and is suitable for large-scale industrial production.

[0036] The diethylhexyl butyramido triazone prepared by the invention is a UVB ultraviolet light absorber and can be used as a sunscreen in cosmetic formulas.

[0037] The above description is only an overview of the technical solution of the present invention. In order to more clearly understand the technical means of the present invention, it can be implemented according to the contents of the specification. In order to make the above and other purposes, features and advantages of the present invention more obvious and easy to understand, the specific implementation methods of the present invention are listed below. DETAILED DESCRIPTION

[0038] The technical solution of the present invention is further described below in conjunction with specific embodiments, but it should be understood that the present invention is not limited to these specific embodiments.

[0039] The inventors of the present application have found through research that the synthesis method reported in the prior art, which is to react N-tert-butyl-4-aminobenzamide with cyanuric chloride to generate a substituted intermediate in the first step and to react the substituted intermediate with isooctyl p-aminobenzoate to generate diethylhexyl butyramido triazone in the second step, has the following disadvantages:

[0040] In the first step, inorganic bases such as sodium carbonate / sodium hydroxide are used as acid-binding agents. The water produced by the reaction will cause the intermediate to hydrolyze and produce impurities. At the same time, the reaction also requires the use of solvents such as acetone that have good solubility for inorganic salts. However, solvents such as acetone will undergo condensation under acid-base catalysis, resulting in a large loss of solvent and affecting product quality. This means that the solvent used in the first step cannot be used in the second step, and the intermediate needs to be treated before use.

[0041] In addition, since the melting range of the product in the second step is relatively long (reaching 90-102° C.), the actual crystallization process of the product post-processing is very difficult. When the excess amount of 4-aminobenzoic acid-2-ethylhexyl ester (i.e., isooctyl p-aminobenzoate) exceeds 2%, it is difficult to obtain a product containing a lower content of isooctyl p-aminobenzoate, which cannot meet the market's increasingly increasing quality requirements.

[0042] Based on the above research findings, the present invention provides a one-pot method for preparing diethylhexyl butyramido triazone.

[0043] The preparation method may at least include the following steps S1 to S2:

[0044] Step S1: In the presence of an organic acid-binding agent, N-tert-butyl-4-aminobenzamide and cyanuric chloride are subjected to a substitution reaction in a non-polar solvent at -10°C to 60°C for 1 to 6 hours to obtain an untreated substitution reaction mixture.

[0045] Those skilled in the art should understand that the substitution reaction mixture obtained in step S1 contains the substitution product obtained by the reaction of N-tert-butyl-4-aminobenzamide and cyanuric chloride (i.e., the substitution intermediate N-tert-butyl-4-[(4,6-dichloro-1,3,5-triazine)amino]benzamide, as shown in the following formula I), and also contains possible remaining unreacted reactants, acid binding agents, solvents, and impurities.

[0046]

[0047] Step S2: adding isooctyl p-aminobenzoate to the substitution reaction mixture obtained in step S1, and reacting at 15° C. to 120° C. for 3 to 15 hours to finally obtain diethylhexyl butyramido triazone. The structural formula of diethylhexyl butyramido triazone is shown in the following formula II.

[0048]

[0049] In particular, the substitution reaction mixture after the reaction in step S1 is directly subjected to the subsequent reaction in step S2 without any purification treatment.

[0050] The method for preparing diethylhexyl butyramido triazone provided by the embodiment of the present invention creatively uses an organic acid binding agent in the substitution reaction of N-tert-butyl-4-aminobenzamide and cyanuric chloride, so that the substitution reaction is more stable, less by-products, and higher product purity. At the same time, due to the use of an organic acid binding agent, a non-polar solvent can be conveniently used in the step of the substitution reaction, so that the substitution reaction mixture can be directly reacted with isooctyl p-aminobenzoate without treatment, thereby realizing the one-pot preparation of diethylhexyl butyramido triazone.

[0051] In some embodiments of the present invention, the reaction temperature of step S2 may be 15° C. to 80° C., and the reaction time may be 3 to 12 hours.

[0052] In some embodiments of the present invention, the organic acid-binding agent may be triethylamine, diisopropylethylamine, N,N-dimethylaniline or N,N-diethylaniline.

[0053] Preferably, the organic acid-binding agent is N,N-dimethylaniline, which is easy to dry and recycle.

[0054] In some embodiments of the present invention, the non-polar solvent may be toluene, xylene, trimethylbenzene, dichloroethane or chloroform, etc., so as to facilitate water washing and recovery of the solvent.

[0055] Preferably, the non-polar solvent is ethylene dichloride.

[0056] In some embodiments of the present invention, the molar ratio of N-tert-butyl-4-aminobenzamide, cyanuric chloride and organic acid-binding agent in step S1 is 1:(0.95-1.15):(1-1.15). By accurately controlling the molar ratio of N-tert-butyl-4-aminobenzamide, cyanuric chloride and organic acid-binding agent, the substitution reaction can be completely carried out and the generation of side reactions and impurities can be reduced as much as possible.

[0057] In some embodiments of the present invention, the molar ratio of isooctyl p-aminobenzoate to N-tert-butyl-4-aminobenzamide added in step S2 is (1.95-2.05): 1. That is, the molar ratio of isooctyl p-aminobenzoate to the substituted intermediate N-tert-butyl-4-[(4,6-dichloro-1,3,5-triazine)amino]benzamide is (1.95-2.05): 1.

[0058] Preferably, the molar ratio of isooctyl p-aminobenzoate to N-tert-butyl-4-aminobenzamide is greater than or equal to 1.95:1 and less than 2.05:1, for example, 1.96:1, 1.97:1, 1.98:1, 1.99:1, 2:1, 2.01:1, 2.02:1, 2.03:1, or 2.04:1.

[0059] In a specific embodiment, the molar ratio of isooctyl p-aminobenzoate to N-tert-butyl-4-aminobenzamide is 2.04:1.

[0060] The method for preparing diethylhexyl butyramido triazone provided by the embodiment of the present invention reduces the reaction ratio of isooctyl p-aminobenzoate in the reaction of the substitution reaction mixture with isooctyl p-aminobenzoate compared to the existing synthesis method. Specifically, the molar dosage ratio of isooctyl p-aminobenzoate to N-tert-butyl-4-aminobenzamide is reduced to 2.05:1 (i.e., the excess of isooctyl p-aminobenzoate is close to 2%) or lower. This makes the reaction purity higher under amine salt catalysis, thereby further improving the purity of the diethylhexyl butyramido triazone product.

[0061] In some embodiments of the present invention, step S2 further includes:

[0062] After the reaction of isooctyl p-aminobenzoate with the substituted product of step S1 (i.e., the substituted intermediate N-tert-butyl-4-[(4,6-dichloro-1,3,5-triazine)amino]benzamide) is completed, the reaction product is washed with water and phase-separated, and the solvent in the organic phase obtained by phase separation is removed to obtain a crude product of diethylhexylbutyramidotriazineketone. The solvent can be removed by distillation, such as reduced pressure distillation.

[0063] Specifically, whether the reaction is completed can be determined by monitoring whether the N-tert-butyl-4-aminobenzamide is completely converted through central control.

[0064] In some specific embodiments, the operation of washing and phase separation of the reaction product in step S2 specifically includes:

[0065] The reaction product is washed with water and then subjected to a first phase separation;

[0066] The organic phase obtained by the first phase separation is adjusted to pH 6.0-10.0 using an alkaline aqueous solution, allowed to stand and a second phase separation is performed;

[0067] The organic phase obtained from the second phase separation was washed with water until it became neutral, and then allowed to stand and the third phase separation was performed.

[0068] The alkaline aqueous solution used for adjusting the pH may be, for example, an aqueous sodium carbonate solution, an aqueous potassium carbonate solution, an aqueous sodium bicarbonate solution, or the like.

[0069] Optionally, the pH value of the organic phase obtained by the first phase separation can be adjusted to 7.5-9.5.

[0070] In some embodiments of the present invention, the preparation method further comprises step S3:

[0071] The crude diethylhexyl butyramido triazone product obtained in step S2 is added with an aqueous organic solvent for extraction and phase separation, the oil layer obtained by phase separation is dropped into water for crystallization, and the precipitated crystals are filtered and dried to obtain a diethylhexyl butyramido triazone product.

[0072] In the method for preparing diethylhexyl butyramido triazone provided in an embodiment of the present invention, after the substitution reaction mixture is reacted with isooctyl p-aminobenzoate to obtain a crude diethylhexyl butyramido triazone product, the crude product is subjected to liquid-liquid extraction with an aqueous organic solvent to purify the product, which can remove most polar impurities and residual salts, thereby further improving the purity of the product.

[0073] In some optional embodiments, the water content in the aqueous organic solvent used as the extraction solvent is 10 wt % to 95 wt %.

[0074] Optionally, the extraction temperature is 0-70°C.

[0075] In some optional embodiments, the aqueous organic solvent can be one selected from tetrahydrofuran aqueous solution, methyltetrahydrofuran aqueous solution, dioxane aqueous solution, alcohol aqueous solution (such as methanol aqueous solution, ethanol aqueous solution, propanol aqueous solution, isopropanol aqueous solution, butanol aqueous solution), etc.

[0076] Preferably, the aqueous organic solvent is an alcohol aqueous solution.

[0077] The following is an explanation of the embodiments of the present invention by specific embodiments. Those skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and the details in this specification can also be modified or changed in various ways based on different viewpoints and applications without departing from the spirit of the present invention.

[0078] Embodiment 1

[0079] Add 76 g (0.41 mol) of cyanuric chloride and 49.7 g (0.41 mol) of N,N-dimethylaniline to 600 g of trimethylbenzene, maintain the kettle temperature at 25-35°C in a water bath, add 76.9 g (0.4 mol) of N-tert-butyl-4-aminobenzamide, stir and react for 1 hour, and the conversion is complete to obtain a mixture of substituted intermediates.

[0080] 197g (0.79mol) of isooctyl p-aminobenzoate was dissolved in 600g of trimethylbenzene, added to the above-mentioned substituted intermediate mixture, and heated to 120°C for reaction for 3h. After the intermediate control conversion was completed, the temperature was lowered and water was added for washing. After standing for phase separation, potassium carbonate aqueous solution was added to the organic phase to adjust the pH to 8.5. After standing for phase separation, the organic phase was washed with water until neutral, and then stood for phase separation again.

[0081] Finally, the organic phase obtained by phase separation was distilled to recover the solvent, and then 600g of 65% ethanol was added. After stirring and heating to 70°C, the phases were separated. The lower oil phase was transferred dropwise into 1000g of water, filtered and dried at room temperature to obtain 294g of white diethylhexyl butanamide triazone product.

[0082] In this example, the yield of the diethylhexyl butyramido triazone product relative to N-tert-butyl-4-aminobenzamide is 96%, and the HPLC purity is 98.5%.

[0083] Embodiment 2

[0084] 36.9 g (0.2 mol) of cyanuric chloride and 20.2 g (0.2 mol) of triethylamine were added to 300 g of ethylene dichloride, and the kettle temperature was maintained at 0-10°C in a water bath. 38.5 g (0.2 mol) of N-tert-butyl-4-aminobenzamide was added and stirred for 4 h. The conversion was completed during the reaction to obtain a mixture of substituted intermediates.

[0085] 101.8g (0.408mol) of isooctyl p-aminobenzoate was dissolved in 200g of dichloroethane, and added dropwise to the above-mentioned substituted intermediate mixture, and the temperature was raised to 84°C for reflux reaction for 15h. After the intermediate control conversion was completed, the temperature was lowered and water was added for washing. After standing for phase separation, sodium bicarbonate aqueous solution was added to the organic phase for washing until pH = 7.5. After standing for phase separation, the organic phase was washed with water until neutral, and then stood for phase separation again.

[0086] Finally, the organic phase obtained by phase separation was distilled to recover the solvent, and then 600g of 85% ethanol was added. After stirring and heating to 70°C, the phases were separated. The lower oil phase was transferred dropwise into 500g of water, filtered at 30°C and dried to obtain 140.9g of white diethylhexylbutanamide triazone product.

[0087] In this example, the yield of the diethylhexyl butyramido triazone product relative to N-tert-butyl-4-aminobenzamide was 92%, and the HPLC purity was 99.0%.

[0088] Embodiment 3

[0089] 36.9 g (0.2 mol) of cyanuric chloride and 25.5 g (0.21 mol) of N,N-dimethylaniline were added to 800 g of toluene, the kettle temperature was maintained at 30-40°C in a water bath, 38.5 g (0.2 mol) of N-tert-butyl-4-aminobenzamide was added, and the reaction was stirred for 1 h. The conversion was completed during the intermediate control to obtain a mixture of substituted intermediates.

[0090] 102.3g (0.41mol) of isooctyl p-aminobenzoate was dissolved in 300g of toluene, and added dropwise to the above-mentioned substituted intermediate mixture, and the temperature was raised to 110°C for reflux reaction for 5h. After the intermediate control conversion was completed, the mixture was cooled to room temperature and washed with water, and after standing for phase separation, sodium carbonate aqueous solution was added to the organic phase to wash until pH = 7.5, and after standing for phase separation, the organic phase was washed with water until neutral, and then stood for phase separation again.

[0091] Finally, the organic phase obtained by phase separation was distilled to recover the solvent, and then 400g of 85% ethanol was added. After stirring and heating to 70°C, the phases were separated. The lower oil phase was transferred dropwise into 500g of water, filtered at 5°C and dried to obtain 144g of white diethylhexylbutanamide triazone product.

[0092] In this example, the yield of the diethylhexyl butyramido triazone product relative to N-tert-butyl-4-aminobenzamide was 94%, and the HPLC purity was 99.0%.

[0093] Experimental data show that the preparation method of the present invention makes the reaction more stable, has fewer by-products and higher purity. Liquid-liquid extraction with an aqueous organic solvent can remove most polar impurities and residual salts. The purity of the obtained diethylhexyl butyramido triazone product can be ≥99.0%, and the yield of diethylhexyl butyramido triazone relative to N-tert-butyl-4-aminobenzamide can be ≥94%.

[0094] The preparation method has a simple process route, readily available raw materials, convenient operation, easy solvent recovery and application, low production cost, and is suitable for large-scale industrial production.

[0095] In the description provided herein, a large number of specific details are described. However, it is understood that embodiments of the present invention can be practiced without these specific details. In some instances, well-known methods, structures and techniques are not shown in detail so as not to obscure the understanding of this description.

[0096] At this point, those skilled in the art should recognize that, although multiple exemplary embodiments of the present invention have been shown and described in detail herein, many other variations or modifications that conform to the principles of the present invention can still be directly determined or derived based on the content disclosed in the present invention without departing from the spirit and scope of the present invention. Therefore, the scope of the present invention should be understood and recognized as covering all these other variations or modifications.

Claims

1. A method for preparing diethylhexyl butyramido triazone, comprising the following steps: Step S1: in the presence of an organic acid-binding agent, subjecting N-tert-butyl-4-aminobenzamide to a substitution reaction with cyanuric chloride in a non-polar solvent at -10°C to 60°C for 1 to 6 hours to obtain an untreated substitution reaction mixture; Step S2: adding isooctyl p-aminobenzoate to the substitution reaction mixture obtained in step S1, and reacting at 15° C. to 120° C. for 3 to 15 hours to finally obtain diethylhexyl butyramido triazone.

2. The method for preparing diethylhexyl butyramido triazone according to claim 1, wherein The organic acid-binding agent is triethylamine, diisopropylethylamine, N,N-dimethylaniline or N,N-diethylaniline.

3. The method for preparing diethylhexyl butyramido triazone according to claim 1, wherein The non-polar solvent is toluene, xylene, trimethylbenzene, dichloroethane or chloroform.

4. The method for preparing diethylhexyl butyramido triazone according to claim 1, wherein The molar ratio of N-tert-butyl-4-aminobenzamide, cyanuric chloride and the organic acid-binding agent is 1:(0.95-1.15):(1-1.15).

5. The method for preparing diethylhexyl butyramido triazone according to claim 1, wherein The molar ratio of isooctyl p-aminobenzoate to N-tert-butyl-4-aminobenzamide is (1.95-2.05):

1.

6. The method for preparing diethylhexyl butyramido triazone according to claim 1, wherein The step S2 further comprises: After the reaction of isooctyl p-aminobenzoate and the substituted product of step S1 is completed, the reaction product is washed with water and phase-separated, and the solvent in the organic phase obtained by phase separation is removed to obtain a crude product of diethylhexyl butyramido triazone.

7. The method for preparing diethylhexyl butyramido triazone according to claim 6, wherein: The method further comprises: Step S3: adding the crude product to an aqueous organic solvent for extraction and phase separation, dropping the oil layer obtained by phase separation into water for crystallization, filtering and drying the precipitated crystals to obtain a diethylhexyl butyramido triazone product.

8. The method of claim 7, wherein: The water content of the aqueous organic solvent is 10wt% to 95wt%; The extraction temperature is 0-70°C.

9. The method of claim 7 or 8, wherein: The aqueous organic solvent is one selected from the following: Tetrahydrofuran aqueous solution, methyltetrahydrofuran aqueous solution, dioxane aqueous solution, methanol aqueous solution, ethanol aqueous solution, propanol aqueous solution, isopropanol aqueous solution, butanol aqueous solution.

10. The method for preparing diethylhexyl butyramido triazone according to claim 6, wherein: The operation of washing the reaction product with water and separating the phases specifically comprises: After washing the reaction product with water, perform a first phase separation; The organic phase obtained by the first phase separation is adjusted to pH 6.0-10.0 using an alkaline aqueous solution, allowed to stand and a second phase separation is performed; The organic phase obtained from the second phase separation was washed with water until it became neutral, and then allowed to stand and the third phase separation was performed.

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