A process for producing oxime silane from butanone oxime

Abstract

The invention relates to a process for producing oxime silane from butanone oxime. According to the process, methyltrichlorosilane, butanone oxime and a solvent are fed into a kettle reactor. After the reaction is completed, the materials are cooled by a circulating cooler, a portion of the materials are returned to the kettle reactor for further reaction, and the other portion of the materials are fed into a separator. Liquid in the lower layer of the separator is fed into the upper part of an extraction tower. Liquid in the upper layer of the separator is evaporated by a thin film evaporator and then fed into the lower part of the extraction tower for recycling. Butanone oxime hydrochloride passes through the extraction tower, and a solvent phase containing methyltributylanoneoxime silane is extracted and overflows from the top of the extraction tower. The collected solvent is returned to the reactor for recycling. Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters a neutralizer. After neutralization, it is separated by an oil-water separator, and the upper layer of liquid is fed into a rectification unit to recover butanone oxime. The lower layer of liquid is fed into an evaporation and crystallization process, and the mother liquor after evaporation, crystallization and filtration is fed into the neutralizer for recycling. The oxime silane prepared by the invention has high purity and chromaticity.

Description

Technical Field

[0001] The invention relates to the technical field of oxime silanes, in particular to a process for producing oxime silanes from butanone oxime. Background Art

[0002] Oximosilanes can be used as crosslinkers in room temperature vulcanized silicone rubber and silicone glass adhesives. The reaction of butanone oxime with methyltrichlorosilane produces a neutral crosslinker in room temperature vulcanized one-component cinnabar rubber. As a key component influencing the quality of organic cinnabar sealants, their production and research have promising applications in a wide range of fields, including the construction, electronics, and automotive industries.

[0003] Chinese Patent CN111018900A: relates to the chemical industry, specifically to a method for preparing methyl tributylanoxime silane; the present invention relates to a method for preparing methyl tributylanoxime silane, in which methyl trichlorosilane is directly added dropwise to a solution of butanone oxime, and a raw material ratio with an excess of butanone oxime is adopted. The excess butanone oxime can both squeeze the reaction process and serve as an acid binding agent, without introducing other substances. The product has a low impurity content and high purity. The present invention also uses an organosilicon-modified activated clay adsorbent to decolorize the generated methyl tributylanoxime silane, which has the characteristics of high removal efficiency and good decolorization effect, and can obtain a product with a very light color, thereby improving product competitiveness.

[0004] Chinese patent CN112717884B: relates to the chemical industry, specifically to a method for refining methyltributylanoximesilane; the present invention uses a modified activated carbon to adsorb and purify the crude methyltributylanoximesilane, and then uses a cationic modified polyethersulfone filter membrane to finely filter the product. The cationic modified polyethersulfone filter membrane contains quaternary ammonium bond groups on its surface, which have a good adsorption effect on hydroxyl compounds. It can adsorb and remove the hydrolysis product of the product, methyltrihydroxysilane, to obtain a high-purity product.

[0005] Chinese patent CN114671903B: relates to the field of fine chemical production, specifically to a method for producing methyltributylanoxime silane in a fixed bed; the invention provides a method for producing methyltributylanoxime silane in a fixed bed by reacting methyltrimethoxysilane with butanone oxime in a fixed bed, catalyzed by a resin catalyst in the fixed bed, and further preparing a resin catalyst in which acetic acid / sulfonic acid coexist, which can be recycled. The fixed bed process can increase the production scale and realize continuous production.

[0006] Currently, the most widely used method for industrial production of oxime silanes is the synthesis process of direct addition of chloronaphthalene. However, this process has problems such as large amounts of butanone oxime-containing wastewater, high energy consumption, low economic benefits of by-products, and poor extraction and separation effects. Summary of the Invention

[0007] In order to solve the above problems, the present invention provides a process for producing oxime silane from butanone oxime, the operating steps of which are as follows:

[0008] S1: 10-16 parts of methyltrichlorosilane, 36-58 parts of butanone oxime, and 80-100 parts of solvent are continuously pumped into a stirred tank reactor through a feed pump through a flow meter. After the reaction is completed, the materials are pumped into a circulating cooler for cooling through a discharge pump; part of the cooled materials are returned to the tank reactor through a circulation pump to continue the reaction, and the other part enters a separator;

[0009] S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling;

[0010] S3: Butanone oxime hydrochloride, 80-100 parts of solvent, and 1-4 parts of extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase containing methyltributylanoxime silane overflows from the top of the extraction tower and is collected in a solvent storage tank 2. The solvent is pumped back to the reactor for recycling by a solvent delivery pump;

[0011] S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process;

[0012] S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation, crystallization and filtration is sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling;

[0013] The extraction and stratification auxiliary agent is prepared by a thiol click chemical reaction among diethyl 12-mercaptododecyl phosphate, allyl polyethylene glycol, polyglycerol-10 oleate and mercaptobenzothiazole.

[0014] The reaction temperature of S1 is 30-40°C.

[0015] The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

[0016] The mass concentration of the sodium hydroxide solution is 5-10%.

[0017] The solvent is 120# gasoline.

[0018] The preparation method of the extraction and stratification auxiliary agent comprises the following steps:

[0019] A1: Add 30-60 parts of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 25-50 parts of allyl polyethylene glycol, 1-5 parts of polyglycerol-10 oleate, 0.005-0.05 parts of mercaptobenzothiazole, and 200-300 parts of DMF, by weight, to a sealed stirred tank and mix;

[0020] A2: After mixing, 0.03-0.08 parts of a photoinitiator is added, and a click chemistry reaction is carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction is completed, DMF is removed by distillation to obtain an extraction and delamination auxiliary agent.

[0021] The molecular weight of the allyl polyethylene glycol is 500-700.

[0022] The stirring rate of A1 is 300-500 rpm.

[0023] The photoinitiator is one of photoinitiator 1173, photoinitiator TPO, photoinitiator 819, photoinitiator benzophenone, and photoinitiator ITX.

[0024] The reaction time of A2 is 30-80 min.

[0025] Reaction mechanism

[0026] 1. Thiol click chemistry: A thiol (-SH) group reacts with an olefin (C=C) to form a sulfide bond (SC). This process is typically carried out in the presence of a free radical initiator or catalyst to ensure high efficiency and selectivity.

[0027] 2. Improving the partition coefficient: Additives improve the partition coefficient in the organic phase by altering the solubility of the target substance in both phases. Additive molecules generated by thiol click chemistry reactions typically possess long carbon chains, which can interact hydrophobically with the target substance (e.g., methyltributylidene oxime silane), increasing its solubility in the organic phase. Furthermore, polar groups in the additive molecules (e.g., benzothiazole rings) can interact with polar molecules in the aqueous phase, further reducing the target substance's solubility in the aqueous phase and thereby improving its partition coefficient in the organic phase.

[0028] 3. Enhanced selectivity: Additives can specifically interact with target substances, reducing co-extraction of impurities and improving product purity. In additive molecules generated by thiol click chemistry, structures such as sulfide bonds (SCs) and benzothiazole rings possess strong specific recognition capabilities. These structures can interact with specific functional groups in the target substance through hydrogen bonding and van der Waals forces, thereby enhancing the selective extraction of the target substance.

[0029] Technical Effects

[0030] Extraction and delamination additives prepared through this thiol click chemistry reaction can significantly improve extraction efficiency. Specifically, these additives can effectively extract the solvent containing methyltributylanoxime silane from butanone oxime hydrochloride in the extraction column. Its technical benefits are mainly reflected in the following aspects:

[0031] 1. Accelerate phase separation: additives can reduce the interfacial tension between the two phases, making it easier to separate the organic phase and the aqueous phase.

[0032] 2. Improve the distribution coefficient: additives can change the distribution coefficient of the target substance in the two phases, making it more inclined to enter the organic phase, thereby improving the extraction efficiency.

[0033] 3. Enhanced selectivity: additives can specifically interact with target substances, reduce co-extraction of impurities, and improve product purity.

[0034] In order to solve the above problems, the present invention provides a process for producing oxime silane from butanone oxime, the operating steps of which are as follows:

[0035] S1: 10-16 parts of methyltrichlorosilane, 36-58 parts of butanone oxime, and 80-100 parts of solvent are continuously pumped into a stirred tank reactor through a feed pump through a flow meter. After the reaction is completed, the materials are pumped into a circulating cooler for cooling through a discharge pump; part of the cooled materials are returned to the tank reactor through a circulation pump to continue the reaction, and the other part enters a separator;

[0036] S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling;

[0037] S3: Butanone oxime hydrochloride, 80-100 parts of solvent, and 1-4 parts of extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase containing methyltributylanoxime silane overflows from the top of the extraction tower and is collected in a solvent storage tank 2. The solvent is pumped back to the reactor for recycling by a solvent delivery pump;

[0038] S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process;

[0039] S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation, crystallization and filtration is sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling;

[0040] The extraction and stratification auxiliary agent is prepared by a thiol click chemical reaction among diethyl 12-mercaptododecyl phosphate, allyl polyethylene glycol, polyglycerol-10 oleate and mercaptobenzothiazole.

[0041] The reaction temperature of S1 is 30-40°C.

[0042] The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

[0043] The mass concentration of the sodium hydroxide solution is 5-10%.

[0044] The solvent is 120# gasoline.

[0045] The preparation method of the extraction and stratification auxiliary agent comprises the following steps:

[0046] A1: Add 30-60 parts of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 25-50 parts of allyl polyethylene glycol, 1-5 parts of polyglycerol-10 oleate, 0.005-0.05 parts of mercaptobenzothiazole, and 200-300 parts of DMF, by weight, to a sealed stirred tank and mix;

[0047] A2: After mixing, 0.03-0.08 parts of a photoinitiator is added, and a click chemistry reaction is carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction is completed, DMF is removed by distillation to obtain an extraction and delamination auxiliary agent.

[0048] The molecular weight of the allyl polyethylene glycol is 500-700.

[0049] The stirring rate of A1 is 300-500 rpm.

[0050] The photoinitiator is one of photoinitiator 1173, photoinitiator TPO, photoinitiator 819, photoinitiator benzophenone, and photoinitiator ITX.

[0051] The reaction time of A2 is 30-80 min.

[0052] Reaction mechanism

[0053] 1. Thiol click chemistry: A thiol (-SH) group reacts with an olefin (C=C) to form a sulfide bond (SC). This process is typically carried out in the presence of a free radical initiator or catalyst to ensure high efficiency and selectivity.

[0054] 2. Improving the partition coefficient: Additives improve the partition coefficient in the organic phase by altering the solubility of the target substance in both phases. Additive molecules generated by thiol click chemistry reactions typically possess long carbon chains, which can interact hydrophobically with the target substance (e.g., methyltributylidene oxime silane), increasing its solubility in the organic phase. Furthermore, polar groups in the additive molecules (e.g., benzothiazole rings) can interact with polar molecules in the aqueous phase, further reducing the target substance's solubility in the aqueous phase and thereby improving its partition coefficient in the organic phase.

[0055] 3. Enhanced selectivity: Additives can specifically interact with target substances, reducing co-extraction of impurities and improving product purity. In additive molecules generated by thiol click chemistry, structures such as sulfide bonds (SCs) and benzothiazole rings possess strong specific recognition capabilities. These structures can interact with specific functional groups in the target substance through hydrogen bonding and van der Waals forces, thereby enhancing the selective extraction of the target substance.

[0056] Technical Effects

[0057] Extraction and delamination additives prepared through this thiol click chemistry reaction can significantly improve extraction efficiency. Specifically, these additives can effectively extract the solvent containing methyltributylanoxime silane from butanone oxime hydrochloride in the extraction column. Its technical benefits are mainly reflected in the following aspects:

[0058] 1. Accelerate phase separation: additives can reduce the interfacial tension between the two phases, making it easier to separate the organic phase and the aqueous phase.

[0059] 2. Improve the distribution coefficient: additives can change the distribution coefficient of the target substance in the two phases, making it more inclined to enter the organic phase, thereby improving the extraction efficiency.

[0060] 3. Enhanced selectivity: additives can specifically interact with target substances, reduce co-extraction of impurities, and improve product purity. DETAILED DESCRIPTION

[0061] In order to further illustrate the technical means and effects adopted by the present invention to achieve the predetermined purpose of the invention, the following is a detailed description in combination with the examples and comparative examples. The test results are shown in Table 1:

[0062] 1. Purity test: determined by gas chromatography;

[0063] 2. Chroma test: Refer to GB3143 "Determination of color of liquid chemical products (Hazcn unit - platinum-cobalt color number)" method and use Pt-Co standard colorimetry to determine the color of the sample.

[0064] Example 1

[0065] A process for producing oxime silane from butanone oxime, comprising the following steps:

[0066] S1: 10g of methyltrichlorosilane, 36g of butanone oxime, and 80g of solvent were continuously pumped into a stirred tank reactor via a feed pump through a flow meter. After the reaction was completed, the materials were pumped into a circulating cooler for cooling via a discharge pump. Part of the cooled materials was returned to the tank reactor via a circulation pump to continue the reaction, and the other part entered a separator.

[0067] S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling;

[0068] S3: Butanone oxime hydrochloride, 80g of solvent, and 1g of extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase with methyltributylanoxime silane overflows from the top of the extraction tower and is collected in solvent storage tank 2. The solvent is pumped back to the reactor for recycling;

[0069] S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process;

[0070] S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation and crystallization is filtered and sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling;

[0071] The extraction and stratification auxiliary agent is prepared by a thiol click chemical reaction among diethyl 12-mercaptododecyl phosphate, allyl polyethylene glycol, polyglycerol-10 oleate and mercaptobenzothiazole.

[0072] The reaction temperature of S1 is 30°C.

[0073] The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

[0074] The mass concentration of the sodium hydroxide solution is 5%.

[0075] The solvent is 120# gasoline.

[0076] The preparation method of the extraction and stratification auxiliary agent comprises the following steps:

[0077] A1: Add 30 g of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 25 g of allyl polyethylene glycol, 1 g of polyglycerol-10 oleate, 0.005 g of mercaptobenzothiazole, and 200 g of DMF to a sealed stirred tank and mix;

[0078] A2: After mixing, 0.03 g of a photoinitiator was added, and a click chemistry reaction was carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction, DMF was removed by distillation to obtain an extraction and delamination aid.

[0079] The molecular weight of the allyl polyethylene glycol is 500.

[0080] The stirring rate of A1 is 300 rpm.

[0081] The photoinitiator is photoinitiator 1173.

[0082] The reaction time of A2 is 30 min.

[0083] Example 2

[0084] A process for producing oxime silane from butanone oxime, comprising the following steps:

[0085] S1: 12g of methyltrichlorosilane, 42g of butanone oxime, and 85g of solvent were continuously pumped into a stirred tank reactor via a feed pump through a flow meter. After the reaction was completed, the materials were pumped into a circulating cooler for cooling via a discharge pump. Part of the cooled materials were returned to the tank reactor via a circulation pump to continue the reaction, and the other part entered a separator.

[0086] S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling;

[0087] S3: Butanone oxime hydrochloride, 85g of solvent, and 2g of extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase with methyltributylanoxime silane overflows from the top of the extraction tower and is collected in solvent storage tank 2. The solvent is pumped back to the reactor for recycling;

[0088] S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process;

[0089] S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation and crystallization is filtered and sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling;

[0090] The extraction and stratification auxiliary agent is prepared by a thiol click chemical reaction among diethyl 12-mercaptododecyl phosphate, allyl polyethylene glycol, polyglycerol-10 oleate and mercaptobenzothiazole.

[0091] The reaction temperature of S1 is 35°C.

[0092] The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

[0093] The mass concentration of the sodium hydroxide solution is 6%.

[0094] The solvent is 120# gasoline.

[0095] The preparation method of the extraction and stratification auxiliary agent comprises the following steps:

[0096] A1: Add 40g of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 35g of allyl polyethylene glycol, 2g of polyglycerol-10 oleate, 0.02g of mercaptobenzothiazole, and 240g of DMF to a sealed stirred tank and mix;

[0097] A2: After mixing, 0.05 g of a photoinitiator was added, and a click chemistry reaction was carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction, DMF was removed by distillation to obtain an extraction and delamination aid.

[0098] The molecular weight of the allyl polyethylene glycol is 600.

[0099] The stirring rate of the A1 is 350 rpm.

[0100] The photoinitiator is photoinitiator TPO.

[0101] The reaction time of A2 is 50 min.

[0102] Example 3

[0103] A process for producing oxime silane from butanone oxime, comprising the following steps:

[0104] S1: 14g of methyltrichlorosilane, 55g of butanone oxime, and 95g of solvent were continuously pumped into a stirred tank reactor via a feed pump through a flow meter. After the reaction was completed, the materials were pumped into a circulating cooler for cooling via a discharge pump. Part of the cooled materials were returned to the tank reactor via a circulation pump to continue the reaction, and the other part entered a separator.

[0105] S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling;

[0106] S3: Butanone oxime hydrochloride, 95g solvent, and 3g extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase with methyltributylanoxime silane overflows from the top of the extraction tower and is collected in solvent storage tank 2. The solvent is pumped back to the reactor for recycling;

[0107] S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process;

[0108] S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation and crystallization is filtered and sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling;

[0109] The extraction and stratification auxiliary agent is prepared by a thiol click chemical reaction among diethyl 12-mercaptododecyl phosphate, allyl polyethylene glycol, polyglycerol-10 oleate and mercaptobenzothiazole.

[0110] The reaction temperature of S1 is 35°C.

[0111] The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

[0112] The mass concentration of the sodium hydroxide solution is 8%.

[0113] The solvent is 120# gasoline.

[0114] The preparation method of the extraction and stratification auxiliary agent comprises the following steps:

[0115] A1: Add 50g of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 45g of allyl polyethylene glycol, 4g of polyglycerol-10 oleate, 0.04g of mercaptobenzothiazole, and 280g of DMF into a sealed stirred tank and mix;

[0116] A2: After mixing, 0.07 g of a photoinitiator was added, and a click chemistry reaction was carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction, DMF was removed by distillation to obtain an extraction and delamination aid.

[0117] The molecular weight of the allyl polyethylene glycol is 600.

[0118] The stirring rate of the A1 is 450 rpm.

[0119] The photoinitiator is photoinitiator 819.

[0120] The reaction time of A2 is 70 min.

[0121] Example 4

[0122] A process for producing oxime silane from butanone oxime, comprising the following steps:

[0123] S1: 16g of methyltrichlorosilane, 58g of butanone oxime, and 100g of solvent are continuously pumped into a stirred tank reactor via a feed pump through a flow meter. After the reaction is completed, the materials are pumped into a circulating cooler for cooling via a discharge pump; part of the cooled materials are returned to the tank reactor via a circulation pump to continue the reaction, and the other part enters a separator;

[0124] S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling;

[0125] S3: Butanone oxime hydrochloride, 100g solvent, and 4g extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase with methyltributylanoxime silane overflows from the top of the extraction tower and is collected in a solvent storage tank 2. The solvent is pumped back to the reactor for recycling;

[0126] S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process;

[0127] S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation and crystallization is filtered and sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling;

[0128] The extraction and stratification auxiliary agent is prepared by a thiol click chemical reaction among diethyl 12-mercaptododecyl phosphate, allyl polyethylene glycol, polyglycerol-10 oleate and mercaptobenzothiazole.

[0129] The reaction temperature of S1 is 40°C.

[0130] The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

[0131] The mass concentration of the sodium hydroxide solution is 10%.

[0132] The solvent is 120# gasoline.

[0133] The preparation method of the extraction and stratification auxiliary agent comprises the following steps:

[0134] A1: Add 60g of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 50g of allyl polyethylene glycol, 5g of polyglycerol-10 oleate, 0.05g of mercaptobenzothiazole, and 300g of DMF into a sealed stirred tank and mix;

[0135] A2: After mixing, 0.08 g of a photoinitiator was added, and a click chemistry reaction was carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction, DMF was removed by distillation to obtain an extraction and delamination aid.

[0136] The molecular weight of the allyl polyethylene glycol is 700.

[0137] The stirring rate of the A1 is 00 rpm.

[0138] The photoinitiator is photoinitiator ITX.

[0139] The reaction time of A2 is 80 min.

[0140] Comparative Example 1

[0141] No extraction and stratification auxiliary agent was added, and the other procedures were the same as in Example 1.

[0142] Comparative Example 2

[0143] Except for not adding allyl polyethylene glycol, the other steps were the same as those in Example 1.

[0144] Comparative Example 3

[0145] The other steps were the same as in Example 1 except that mercaptobenzothiazole was not added.

[0146] Table 1

[0147] purity / % Chroma Example 1 99.94 7 Example 2 99.96 6 Example 3 99.98 5 Example 4 99.99 5 Comparative Example 1 87.67 28 Comparative Example 2 95.55 15 Comparative Example 3 97.13 12

[0148] Through the data analysis of the above examples and comparative examples, the oxime silane prepared by the present invention has high purity and chromaticity.

[0149] The above description is merely a preferred embodiment of the present invention and does not constitute any form of limitation to the present invention. Although the present invention has been disclosed as above in terms of a preferred embodiment, it is not intended to limit the present invention. Any person skilled in the art can, without departing from the scope of the technical solution of the present invention, make some changes or modifications to equivalent embodiments using the technical contents disclosed above. However, any brief modifications, equivalent changes and modifications made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solution of the present invention are still within the scope of the technical solution of the present invention.

Claims

1. A process for producing oxime silane from butanone oxime, comprising the following steps: S1: 10-16 parts of methyltrichlorosilane, 36-58 parts of butanone oxime, and 80-100 parts of solvent are continuously pumped into a stirred tank reactor through a feed pump through a flow meter. After the reaction is completed, the materials are pumped into a circulating cooler for cooling through a discharge pump; part of the cooled materials are returned to the tank reactor through a circulation pump to continue the reaction, and the other part enters a separator; S2: The butanone oxime hydrochloride liquid in the lower layer of the separator is pumped into the upper part of the extraction tower by the extraction tower feed pump; the upper layer of the separator is evaporated by a thin film evaporator, and the evaporated solvent enters the solvent storage tank 1 and then enters the lower part of the extraction tower for recycling; S3: Butanone oxime hydrochloride, 80-100 parts of solvent, and 1-4 parts of extraction and delamination aid are subjected to liquid-liquid mass transfer in an extraction tower. The extracted solvent phase containing methyltributylanoxime silane overflows from the top of the extraction tower and is collected in a solvent storage tank 2. The solvent is pumped back to the reactor for recycling by a solvent delivery pump; S4: Butanone oxime hydrochloride comes out from the bottom of the extraction tower and enters the neutralizer, where it reacts with the neutralizer sodium hydroxide solution. After neutralization, it enters the oil-water separator and is separated into two layers. The upper layer liquid is butanone and a small amount of methyltributylanoxime silane, which is sent to the distillation unit to recover butanone oxime; the lower layer liquid is sodium chloride solution, which is sent to the evaporation and crystallization process; S5: The sodium chloride solution enters the evaporator, evaporates and removes a large amount of water, and then enters the crystallizer for cooling and crystallization; the mother liquor after evaporation, crystallization and filtration is sent to the mother liquor tank; the mother liquor is sent to the neutralizer for recycling; The extraction and stratification auxiliary agent is prepared by the addition reaction of thiol and olefin by diethyl 12-mercaptododecyl phosphate and polyglycerol-10 oleate; The preparation method of the extraction and stratification auxiliary agent comprises the following steps: A1: Add 30-60 parts of diethyl 12-mercaptododecyl phosphate (CAS: 1049677-30-6), 25-50 parts of allyl polyethylene glycol, 1-5 parts of polyglycerol-10 oleate, 0.005-0.05 parts of mercaptobenzothiazole, and 200-300 parts of DMF, by weight, to a sealed stirred tank and mix; A2: After mixing, 0.03-0.08 parts of a photoinitiator is added, and a click chemistry reaction is carried out under ultraviolet light with a maximum absorption wavelength of 365 nm. After the reaction is completed, DMF is removed by distillation to obtain an extraction and delamination auxiliary agent.

2. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The reaction temperature of S1 is 30-40°C.

3. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The extraction tower is provided with a plurality of compartments with turbines, and the stirring drives the impeller to rotate at a high speed, so that the two phases generate driving forces in the axial and radial directions.

4. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The mass concentration of the sodium hydroxide solution is 5-10%.

5. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The solvent is 120# gasoline.

6. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The molecular weight of the allyl polyethylene glycol is 500-700.

7. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The stirring rate of A1 is 300-500 rpm.

8. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The photoinitiator is one of photoinitiator 1173, photoinitiator TPO, photoinitiator 819, photoinitiator benzophenone, and photoinitiator ITX.

9. The process for producing oxime silane from butanone oxime according to claim 1, wherein: The reaction time of A2 is 30-80 min.