Safe and efficient pentanone oxime silane and preparation method thereof
By preparing pentanone oxime silane, the problems of low boiling point and high viscosity of existing crosslinking agents have been solved, realizing the efficient and safe preparation of pentanone oxime silane, improving processing performance and application range, and reducing environmental treatment costs.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Filing Date
- 2026-06-03
- Publication Date
- 2026-07-10
AI Technical Summary
Existing acetone oxime and butanone oxime crosslinking agents have too low a boiling point and too high a viscosity, which limits their processing performance and applicability in specific application scenarios.
Pentanone oxime silane was prepared by using 2-pentanone oxime and vinyl trihalosilane as raw materials, through specific solvents and reaction conditions, avoiding the use of liquid ammonia or ammonia gas, controlling the molar ratio and concentration, and performing vacuum distillation and vacuum drying to obtain pentanone oxime silane with high boiling point and suitable viscosity.
It achieves the high boiling point and good processing performance of pentanone oxime silane, eliminates the risk of ammonia leakage and explosion, reduces solid waste generation, lowers energy consumption and costs, and expands the scope of application.
Smart Images
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Abstract
Description
Technical Field
[0001] This invention relates to the technical field of organosilicon material synthesis, and in particular to a safe and efficient pentanone oxime silane and its preparation method. Background Technology
[0002] Ketooxime silane crosslinking agents have a wide range of applications, commonly used in the production of room temperature vulcanizing (RTV) silicone rubber. Silicone rubber is widely used in the construction and electronics industries for encapsulation and filling of components, as well as in automotive gaskets and window seals. Due to the booming development of the rubber industry, the demand for ketoxime silane crosslinking agents is also increasing. Different silane configurations offer varying degrees of performance enhancement to rubber, thus new ketoxime silanes are constantly being developed. Room temperature vulcanizing (RTV) silicone rubber is an organosilicon elastomer that cures at room temperature upon contact with moisture in the air, without the need for heating or pressurization. Its physical form is typically a flowing fluid or paste. Its chemical composition mainly includes polydimethylsiloxane, crosslinking agents, reinforcing fillers (such as nano-calcium carbonate and fumed silica), and additives, forming a three-dimensional network structure through condensation or addition reactions.
[0003] In related technologies, existing crosslinking agents with acetone oxime, butanone oxime, and other structures as core units have defects such as too low boiling point and too high viscosity, which limits their processing performance and application scope in specific application scenarios. Summary of the Invention
[0004] To improve the processing performance and applicability of pentanone oxime silane, this application provides a safe and efficient pentanone oxime silane and its preparation method.
[0005] Firstly, this application provides a safe and efficient method for preparing pentanone oxime silanes, employing the following technical solution: A safe and efficient method for preparing pentanone oxime silane includes the following steps: S1. Dissolve 2-pentanone oxime in a first organic solvent to obtain a first solution; S2. Dissolve vinyltrihalosilane in a second organic solvent to obtain a second solution; S3. Under stirring and at 20~35℃, the second solution is added dropwise to the first solution. After the addition is complete, the reaction continues until completion, and a reaction solution is obtained. S4. Cool the reaction solution to room temperature, filter, collect the filtrate, concentrate and dry to obtain 2-pentanone oxime silane; Wherein, the first organic solvent and the second organic solvent are both selected from one or more of n-hexane, xylene, dichloromethane, tetrahydrofuran, and toluene.
[0006] In one specific implementation, the molar ratio of 2-pentanone oxime described in step S1 to vinyl trihalosilane described in step S2 is (2.5~3.0):1.
[0007] In one specific implementation, in step S1, the mass concentration of 2-pentanone oxime in the first solution is 40-65%.
[0008] In one specific implementation, in step S2, the mass concentration of vinyltrihalosilane in the second solution is 30-50%.
[0009] In one specific feasible implementation, in step S3, the dripping time is 30~60 minutes.
[0010] In one specific feasible implementation, in step S3, after the addition is complete, continue stirring and keeping the temperature constant for 1.5 to 3 hours to complete the reaction.
[0011] In one specific implementation scheme, in step S4, the concentration and drying are carried out as follows: vacuum distillation is performed under the conditions of a water bath at 55~65℃ and a negative pressure of -0.095~-0.098MPa to recover and remove the organic solvent. After no distillate flows out, drying is continued under vacuum conditions of 60~70℃ and <10Pa for 30~60 minutes to complete the concentration and drying.
[0012] Secondly, this application provides a safe and efficient pentanone oxime silane, which adopts the following technical solution: A safe and efficient pentanone oxime silane has the following configuration: .
[0013] In summary, this application has the following beneficial effects: 1. This application can prepare 2-pentanone oxime silane by using 2-pentanone oxime and vinyl trihalosilane as raw materials. Moreover, no liquid ammonia or ammonia gas is used in the whole process, which fundamentally eliminates the risk of ammonia leakage, poisoning and explosion. At the same time, it greatly reduces the amount of solid waste generated, with low energy consumption and low cost.
[0014] 2. This application can increase the boiling point of 2-pentanone oxime silane, and 2-pentanone oxime silane has moderate viscosity, good processing performance, and a wide range of applications.
[0015] 3. In this application, the molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is (2.5~3.0):1. The mass concentration of 2-pentanone oxime in the first solution is 40~65%, and the mass concentration of vinyl trihalosilane in the second solution is 30~50%, which can further increase the boiling point and viscosity of 2-pentanone oxime silane. Attached Figure Description
[0016] Figure 1 This is a configuration diagram of the 2-pentanone oxime silane prepared in Example 1.
[0017] Figure 2 This is a chromatogram of the preparation of 2-pentanone oxime silane in Example 1. Detailed Implementation
[0018] Unless otherwise specified, all raw materials used in this application were commercially available. 2-Pentanone oxime, CAS No. 105-44-2, analytical grade. n-Hexane, CAS No. 110-54-3, analytical grade. Vinyl trihalosilane is vinyltrichlorosilane, CAS No. 75-94-5, analytical grade. Xylene, CAS No. 1330-20-7, analytical grade. Dichloromethane, CAS No. 75-09-2, analytical grade. Tetrahydrofuran, CAS No. 109-99-9, analytical grade. Toluene, CAS No. 108-88-3, analytical grade.
[0019] The present application will be further described in detail below with reference to embodiments and comparative examples.
[0020] Example Example 1
[0021] This embodiment also provides a safe and efficient method for preparing pentanone oxime silane, comprising the following steps: S1. Dissolve 2-pentanone oxime in n-hexane to obtain a first solution, wherein the mass concentration of 2-pentanone oxime in the first solution is 47.5%.
[0022] S2. Dissolve vinyltrihalosilane in n-hexane to obtain a second solution, wherein the mass concentration of vinyltrihalosilane in the second solution is 40%. The molar ratio of 2-pentanone oxime in step S1 to vinyltrihalosilane in step S2 is 2.75:1.
[0023] S3. Under stirring and constant temperature of 28°C, the second solution is added dropwise to the first solution at a uniform rate over a period of 45 minutes. After the addition is complete, stirring and maintaining the temperature continue for 2.2 hours to complete the reaction and obtain the reaction solution.
[0024] S4. Cool the reaction solution to room temperature naturally, filter, collect the filtrate, and perform vacuum distillation under a constant temperature water bath at 60℃ and a negative pressure of -0.096MPa to recover and remove the organic solvent. After no more distillate flows out, continue to dry under vacuum conditions of 65℃ and <10Pa for 45 minutes to complete the concentration and drying, and obtain 2-pentanone oxime silane.
[0025] Example 2
[0026] The only difference between this embodiment and Embodiment 1 is that, in step S1, an equal amount of xylene is used to replace n-hexane.
[0027] Example 3
[0028] The only difference between this embodiment and Embodiment 1 is that, in step S1, hexane is replaced with a mixture of n-hexane, xylene, dichloromethane, tetrahydrofuran, and toluene in an equal volume ratio of 1:1:1:1:1.
[0029] Example 4
[0030] The only difference between this embodiment and Embodiment 1 is that, in step S2, an equal amount of xylene is used to replace n-hexane.
[0031] Example 5
[0032] The only difference between this embodiment and Embodiment 1 is that, in step S2, hexane is replaced with a mixture of n-hexane, xylene, dichloromethane, tetrahydrofuran, and toluene in an equal volume ratio of 1:1:1:1:1.
[0033] Example 6
[0034] The only difference between this embodiment and Embodiment 1 is that, in step S1, the mass concentration of 2-pentanone oxime in the first solution is 35%.
[0035] Example 7
[0036] The only difference between this embodiment and Embodiment 1 is that, in step S1, the mass concentration of 2-pentanone oxime in the first solution is 40%.
[0037] Example 8
[0038] The only difference between this embodiment and Embodiment 1 is that, in step S1, the mass concentration of 2-pentanone oxime in the first solution is 65%.
[0039] Example 9
[0040] The only difference between this embodiment and Embodiment 1 is that, in step S1, the mass concentration of 2-pentanone oxime in the first solution is 70%.
[0041] Example 10
[0042] The only difference between this embodiment and Embodiment 1 is that, in step S2, the mass concentration of vinyltrihalosilane in the second solution is 25%.
[0043] Example 11
[0044] The only difference between this embodiment and Embodiment 1 is that, in step S2, the mass concentration of vinyltrihalosilane in the second solution is 30%.
[0045] Example 12
[0046] The only difference between this embodiment and Embodiment 1 is that, in step S2, the mass concentration of vinyltrihalosilane in the second solution is 50%.
[0047] Example 13
[0048] The only difference between this embodiment and Embodiment 1 is that, in step S2, the mass concentration of vinyltrihalosilane in the second solution is 55%.
[0049] Example 14
[0050] The only difference between this embodiment and Embodiment 1 is that the molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is 2.25:1.
[0051] Example 15
[0052] The only difference between this embodiment and Embodiment 1 is that the molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is 2.5:1.
[0053] Example 16
[0054] The only difference between this embodiment and Embodiment 1 is that the molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is 3.0:1.
[0055] Example 17
[0056] The only difference between this embodiment and Embodiment 1 is that the molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is 3.25:1.
[0057] Example 18
[0058] The only difference between this embodiment and Embodiment 1 is that, in step S4, vacuum distillation is carried out under a constant temperature water bath at 55°C and a negative pressure of -0.095MPa to recover and remove the organic solvent. After no more distillate flows out, the mixture is dried for 30 minutes under a vacuum of 60°C and <10Pa to complete the concentration and drying.
[0059] Example 19
[0060] The only difference between this embodiment and Embodiment 1 is that, in step S4, vacuum distillation is carried out under a constant temperature water bath at 65°C and a negative pressure of -0.098MPa to recover and remove the organic solvent. After no more distillate flows out, the mixture is dried for 60 minutes under a vacuum of 70°C and <10Pa to complete the concentration and drying.
[0061] Example 20
[0062] The only difference between this embodiment and Embodiment 1 is that, in step S3: under stirring and constant temperature of 20°C, the second solution is added dropwise to the first solution at a uniform rate over a period of 30 minutes. After the addition is complete, stirring and maintaining the temperature continue for 1.5 hours to complete the reaction and obtain the reaction solution.
[0063] Example 21
[0064] The only difference between this embodiment and Embodiment 1 is that, in step S3: under stirring and constant temperature of 35°C, the second solution is added dropwise to the first solution at a uniform rate over a period of 60 minutes. After the addition is complete, stirring and maintaining the temperature continue for 3 hours to complete the reaction and obtain the reaction solution.
[0065] Comparative Example Comparative Example 1 The only difference between this comparative example and Example 1 is that the safe and efficient method for preparing pentanone oxime silane includes the following steps: S1. Dissolve 2-pentanone oxime and vinyl trihalosilane in n-hexane. The mass concentration of 2-pentanone oxime is 47.5%, and the molar ratio of 2-pentanone oxime to vinyl trihalosilane in step S2 is 2.75:1.
[0066] S2. Under stirring and constant temperature of 28°C, stir and keep warm for 1.5 hours to complete the reaction and obtain the reaction solution.
[0067] S3. Cool the reaction solution to room temperature naturally, filter, collect the filtrate, and perform vacuum distillation under a constant temperature water bath at 60℃ and a negative pressure of -0.096MPa to recover and remove the organic solvent. After no more distillate flows out, continue to dry under vacuum conditions of 65℃ and <10Pa for 45 minutes to complete the concentration and drying, and obtain 2-pentanone oxime silane.
[0068] Performance testing The following performance tests were conducted on Examples 1-21 and Comparative Example 1: The product prepared in Example 1 was detected by GC-LC chromatography, and the chromatogram is shown below. Figure 2 As shown.
[0069] According to GB / T 7534, the boiling point (°C) of the prepared product at a pressure of 10 mmHg was tested. According to GB / T 265, the viscosity (mPa·s) of the prepared product at 25°C was tested.
[0070] The test results are shown in Table 1.
[0071] Table 1 In conjunction with Example 1 and Table 1, Figure 1-2 It can be seen that the product prepared in Example 1 is 2-pentanone oxime silane, with the following configuration: Figure 1 As shown. Furthermore, Example 1 does not use liquid ammonia or ammonia gas throughout the process, fundamentally eliminating the risks of ammonia leakage, poisoning, and explosion, while significantly reducing the amount of ammonium chloride solid waste generated and lowering environmental treatment costs. The reaction temperature is relatively low, avoiding side reactions caused by high temperatures, resulting in low energy consumption and easy industrial-scale production. The raw materials used, 2-pentanone oxime and vinyl trihalosilane, are both commercially available products, widely sourced, and inexpensive.
[0072] This is likely because, compared to acetone oxime and butanone oxime, 2-pentanone oxime has a longer alkyl chain, and the van der Waals forces between molecules increase significantly with increasing alkyl chain length. Higher temperatures are required to overcome these intermolecular forces and vaporize the liquid. Therefore, the boiling point of the product in Example 1 is much higher than that of short-chain ketoxime silanes. Furthermore, Example 1 achieves a moderate viscosity by balancing the long-chain alkyl groups.
[0073] As can be seen from Comparative Example 1, Examples 1-20, and Table 1, the 2-pentanone oxime silanes prepared in Examples 1-20 all have higher boiling points and viscosities compared to Comparative Example 1. This indicates that 2-pentanone oxime silanes with good processing properties and wide applicability can be prepared using the raw material ratios and preparation methods within the range of Examples 1-20.
[0074] By comparing the detection data of each embodiment, it can be seen that when the molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is (2.5~3.0):1, the mass concentration of 2-pentanone oxime in the first solution is 40~65%, and the mass concentration of vinyl trihalosilane in the second solution is 30~50%, the boiling point and viscosity of 2-pentanone oxime silane can be further increased.
[0075] This specific embodiment is merely an explanation of this application and is not intended to limit it. After reading this specification, those skilled in the art can make modifications to this embodiment without contributing any inventive step, but such modifications are protected by patent law as long as they fall within the scope of the claims of this application.
Claims
1. A safe and efficient method for preparing pentanone oxime silane, characterized in that, Includes the following steps: S1. Dissolve 2-pentanone oxime in a first organic solvent to obtain a first solution; S2. Dissolve vinyltrihalosilane in a second organic solvent to obtain a second solution; S3. Under stirring and at 20~35℃, the second solution is added dropwise to the first solution. After the addition is complete, the reaction continues until completion, and a reaction solution is obtained. S4. Cool the reaction solution to room temperature, filter, collect the filtrate, concentrate and dry to obtain 2-pentanone oxime silane; Wherein, the first organic solvent and the second organic solvent are both selected from one or more of n-hexane, xylene, dichloromethane, tetrahydrofuran, and toluene.
2. The safe and efficient method for preparing pentanone oxime silane according to claim 1, characterized in that, The molar ratio of 2-pentanone oxime in step S1 to vinyl trihalosilane in step S2 is (2.5~3.0):
1.
3. The safe and efficient method for preparing pentanone oxime silane according to claim 2, characterized in that, In step S1, the mass concentration of 2-pentanone oxime in the first solution is 40-65%.
4. The safe and efficient method for preparing pentanone oxime silane according to claim 3, characterized in that, In step S2, the mass concentration of vinyltrihalosilane in the second solution is 30-50%.
5. The safe and efficient method for preparing pentanone oxime silane according to claim 1, characterized in that, In step S3, the dripping time is 30~60 minutes.
6. The safe and efficient method for preparing pentanone oxime silane according to claim 5, characterized in that, In step S3, after the addition is complete, continue stirring and keeping the temperature constant for 1.5 to 3 hours to complete the reaction.
7. The safe and efficient method for preparing pentanone oxime silane according to claim 1, characterized in that, In step S4, the concentration and drying are carried out as follows: vacuum distillation is performed under the conditions of a water bath at 55~65℃ and a negative pressure of -0.095~-0.098MPa to recover and remove the organic solvent. After no distillate flows out, the mixture is dried under vacuum conditions of 60~70℃ and <10Pa for 30~60 minutes to complete the concentration and drying.
8. A pentanone oxime silane prepared by the safe and efficient method for preparing pentanone oxime silane according to any one of claims 1-7, characterized in that, It has the following configuration: 。