CN116621874A - Silane derivative, preparation method and application thereof - Google Patents

Abstract

The application discloses a silane derivative, a preparation method and application thereof. In one aspect, the application discloses a silane derivative; on the other hand, the application also discloses a preparation method of the silane derivative, which is prepared by taking APTES and PPDCL as raw materials and synthesizing the raw materials in a THF solvent containing TEA. In a third aspect, the application also discloses application of the silane derivative in the fields of medicine and material preparation. The silane derivative can meet the performance requirements of the high-performance and high-functional composite material on the silane coupling agent, and the preparation process is relatively simple, the preparation yield is higher, and the purity of the prepared product is relatively higher.

Description

Silane derivative, preparation method and application thereof

Technical Field

The application relates to the technical field of organic synthesis, in particular to a silane derivative, a preparation method and application thereof.

Background

The silane coupling agent APTES, the chemical name of which is 3-aminopropyl triethoxysilane, is an aminosilane which is frequently used in the silanization process, the surface of the aminosilane is functionalized by alkoxysilane molecules, the appearance of the aminosilane is colorless or yellowish transparent liquid, the universality is strong, and the aminosilane is soluble in organic solvents. APTES molecules contain two different active groups of amino and oxygen, and are commonly used for coupling organic polymers and inorganic fillers, so that the cohesiveness of the APTES is enhanced, and the mechanical, electrical, water-resistant, anti-aging and other performances of the product are improved. APTES is commonly used in industries such as glass fiber, casting, textile auxiliary, insulating materials, adhesives and the like; suitable polymers for APTES are epoxy, phenolic, melamine, nylon, polyvinyl chloride, polyacrylic, polyurethane, and the like. APTES is also an excellent adhesion promoter, can be used for polyurethane, epoxy, nitrile, phenolic aldehyde adhesives and sealing materials, can improve pigment dispersibility and improve adhesion to glass, aluminum and iron metals, and is also suitable for polyurethane, epoxy, acrylic latex and other coatings. Therefore, the method has very wide application in the chemical industry field.

However, with the rapid development of high-performance and high-functional composite materials, new and higher requirements are also put on the performance of the silane coupling agent and the use technology thereof. For example, to allow one coupling agent to accommodate multiple resins, a multifunctional silane is required; for another example, in order to eliminate the influence of the properties of the filler itself on the composite material, a silane or the like capable of passivating the filler surface is required. The silane coupling agent APTES can not better meet the performance requirements of the current high-performance and high-functional composite material on the silane coupling agent. Although the industrial mass production of the silane coupling agent APTES is realized in China earlier, the yield of the product is generally not high in the existing mass production process at present; meanwhile, byproducts generated in the preparation process are seriously corroded on equipment and pollute the environment.

At present, the prior art is constantly researching silane derivatives to meet the performance requirements of high-performance and high-functional composite materials on silane coupling agents, and simultaneously developing corresponding preparation processes with high yield and high purity and environment friendliness. However, the existing silane derivative has a complex structure, the synthesis reaction is also complex, and the yield is difficult to improve; and the subsequent treatment is relatively complex, the purity of the prepared product is not high, and the current market needs are difficult to meet.

Disclosure of Invention

In order to solve at least one technical problem, a silane coupling agent product which can meet the performance requirements of high-performance and high-functional composite materials on silane coupling agents, has relatively simple preparation process, higher yield and relatively higher purity is developed, and the application provides a silane derivative, a preparation method and application thereof.

In one aspect, the present application provides a silane derivative having the structural formula:

by adopting the technical scheme, the silane derivative contains two siloxy groups, so that the silane derivative has good reactivity and compatibility to inorganic matters and organic matters; meanwhile, the silane derivative provided by the application contains a phenylphosphine group, and the group is widely applied to the field of medicine synthesis, so that the silane derivative provided by the application can be used as an excellent medical intermediate in the field of medicine synthesis, and the application range of the silane derivative provided by the application is effectively widened.

On the other hand, the application also provides a preparation method of the silane derivative, which adopts the following process route:

optionally, the preparation method of the silane derivative comprises the following steps:

s1, dissolving APTES in THF, and adding TEA to prepare a solution;

s2, dissolving PPDCL in THF to prepare a solution, and dropwise adding the solution prepared in the step S1 into the solution under the low-temperature condition to obtain a reaction solution;

s3, reacting the reaction solution obtained in the step S2 for more than 20min at low temperature, reacting for more than 5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s4, adding ethyl acetate and saturated saline into the crude silane derivative liquid obtained in the step S3, and removing byproducts through extraction to obtain an oil phase which is primarily purified;

s5, adding anhydrous calcium sulfate into the oil phase obtained in the step S4, stirring, standing, and filtering the oil phase after standing to obtain a secondary purified oil phase;

s6, separating and removing ethyl acetate in the oil phase obtained in the step S5, and drying to remove the solvent to obtain a silane derivative pure product.

By adopting the technical scheme, APTES and PPDCL are adopted as raw materials, so that the target silane derivative is synthesized, and the raw materials are wide in source and easy to obtain; meanwhile, the application adopts the THF containing TEA as the reaction solvent, which not only has low cost, but also has high reaction yield, good selectivity, easy separation and purification and less pollution; in addition, the synthetic method disclosed by the application is simple in steps, does not need the synthetic steps of protecting and deprotecting functional groups, is mild in reaction conditions, easy to control and high in purity of the prepared product.

Optionally, in the steps S1 and S2, the molar ratio of the APTES, TEA and PPDCL is 1:1.5:1.

By adopting the technical scheme, the material feeding ratio is optimized, so that the silane coupling agent can be completely reacted, and the residue is effectively avoided.

Optionally, in the step S2, the dripping time of the solution configured in the dripping step S1 is controlled to be 1h.

Optionally, in the step S2, the low-temperature condition is an ice bath condition, the low-temperature reaction time is controlled to be 30-90 min, and the normal-temperature reaction time is controlled to be 6-8 h.

Optionally, in the step S4, the extracting is performed to remove the byproduct, by extracting the byproduct into the aqueous phase, and then separating the aqueous phase; the extraction operation is repeated 3 to 5 times.

Optionally, in the step S5, the standing time is controlled to be 0.5-1 h.

Optionally, in step S6, the ethyl acetate is separated and removed by spin evaporation, and the spin evaporation temperature is controlled at 60-75 ℃.

In a third aspect, the application also provides the use of the above silane derivatives in the field of pharmaceutical and material preparation.

In summary, the present application includes at least one of the following beneficial technical effects:

the reaction operation of the application is simpler; the reaction substrate is simple and the source is wide.

The application has the advantages of cheap reaction substrate, high yield, good selectivity, easy separation and purification, less pollution, simple steps, and capability of omitting the steps of protecting and deprotecting functional groups for synthesis, and the target product silane derivative is widely applicable to aspects of drug design, material science and the like.

The product of the application can lead the high molecular polymer to have good compatibility.

1. The silane derivative contains two siloxy groups, so that the silane derivative has good reactivity and compatibility to inorganic matters and organic matters; meanwhile, the silane derivative provided by the application contains a phenylphosphine group, and the group is widely applied to the field of medicine synthesis, so that the silane derivative provided by the application can be used as an excellent medical intermediate in the field of medicine synthesis, and the application range of the silane derivative provided by the application is effectively widened.

2. The silane derivative can lead the high molecular polymer to have good compatibility; the functional group of the silane derivative can enable one end of the silane derivative to react with hydroxyl of an inorganic material to form a hydrogen bond, and the silane derivative is condensed, dehydrated and solidified under certain conditions to form a covalent bond, and the other end of the silane derivative can be combined with an organic high-molecular material, so that good compatibility is generated among the organic high-molecular material, the silane coupling agent and the inorganic material.

3. The preparation of the silane derivative adopts APTES and PPDCL as raw materials, synthesizes the target silane derivative of the application, has wide raw material sources and is easy to obtain.

4. The preparation of the silane derivative adopts TEA-containing THF as a reaction solvent, so that the cost is low, the reaction yield is high, the selectivity is good, the separation and purification are easy, and the pollution is less.

5. The preparation of the silane derivative disclosed by the application is simple in steps, does not need the synthesis steps of protecting and deprotecting functional groups, is mild in reaction conditions, easy to control and high in purity of the prepared product.

Detailed Description

The present application will be described in further detail with reference to examples.

Noun interpretation:

APTES: the chemical name of KH550 is 3-aminopropyl triethoxy silane, which is a common silane coupling agent;

PPDCL: the chemical name is dichlorophenyl phosphine, which is a common phosphine-containing synthetic raw material;

THF: tetrahydrofuran is a common organic solvent;

TEA: the chemical name is triethanolamine or tri (2-hydroxyethyl) amine, and is a chemical raw material with wide application.

The application relates to a silane derivative, which has the structural formula:

the preparation of the silane derivative adopts the following process route:

the silane derivative of the present application uses APTES and PPDCL as raw materials, and two APTES molecules are substituted by two chlorine atoms of PPDCL through reaction, and two APTES groups are connected to a phenylphosphine group.

The silane derivative contains two siloxy groups, so that the silane derivative has good reactivity and compatibility to inorganic matters and organic matters; meanwhile, the silane derivative contains a phenylphosphine group, and the group has wide application in the field of medicine synthesis, so that the silane derivative can be used as an excellent medical intermediate in the field of medicine synthesis. The design of the application ensures that the silane derivative can be used as an auxiliary agent such as a coupling agent and the like, and can be used as a drug intermediate. The application contains two siloxy groups, so that the application has excellent compatibility and reactivity and very good performance when being used as a drug intermediate.

When the silane derivative is applied as a phosphine-containing silane coupling agent, the compatibility between the high polymer and the inorganic filler can be improved, and the thermal stability of the high polymer can be improved under the action of phosphine-containing groups, so that the high polymer has certain flame retardant property.

The following are examples of the application

The sources of the raw materials are as follows:

APTES-purity over 99% Shanghai Ala Biochemical technology Co., ltd; PPDCL-purity above 99%, shanghai aladine biochemical technologies, inc; TEA-purity over 99% from Tianjin Seen Biochemical Co., ltd; THF-purity above 99%, beginningcarbofuran technologies limited.

Example 1

APTES, PPDCL and TEA of this example were fed in a molar ratio of 2:1:2.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b at the temperature of 5 ℃, and controlling the dropwise adding time to be about 30 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution at the temperature of 5 ℃ for 20min, reacting at the room temperature for 5h, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 2

APTES, PPDCL and TEA of this example were fed in a molar ratio of 2:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b at the temperature of 5 ℃, and controlling the dropwise adding time to be about 30 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution at the temperature of 5 ℃ for 20min, reacting at the room temperature for 5h, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 3

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1.5:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b at the temperature of 5 ℃, and controlling the dropwise adding time to be about 30 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution at the temperature of 5 ℃ for 20min, reacting at the room temperature for 5h, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 4

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b at the temperature of 5 ℃, and controlling the dropwise adding time to be about 30 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution at the temperature of 5 ℃ for 20min, reacting at the room temperature for 5h, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 5

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b at the temperature of 0 ℃, and controlling the dropwise adding time to be about 20 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution at 0 ℃ for 20min, reacting for 5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 6

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b at the temperature of 0 ℃, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution at 0 ℃ for 30min, reacting for 6h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 7

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 45 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 60min under the ice bath condition, reacting for 7h under the room temperature condition, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 8

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 90min under the ice bath condition, reacting for 8h under the room temperature condition, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 9

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 100min under the ice bath condition, reacting for 8.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 10

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 70 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 90min under the ice bath condition, reacting for 8h under the room temperature condition, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 11

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 3 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 12

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 4 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 13

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 5 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 10min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 14

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 4 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 30min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 15

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 4 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 60min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 16

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 4 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 70min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase by heating, controlling the heating temperature within 85 ℃, and then removing the solvent by vacuum drying to obtain the silane derivative pure product of the embodiment.

Example 17

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 4 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 60min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase through rotary evaporation, controlling the rotary evaporation temperature to be 60-75 ℃, and then drying in vacuum to remove the solvent to obtain the silane derivative pure product of the embodiment.

Example 18

APTES, PPDCL and TEA of this example were fed in a molar ratio of 1:1:1.5.

The silane derivative of this example was prepared by the following method, comprising the steps of:

s1, dissolving APTES with a formula amount in solvent THF, and adding TEA with a formula amount to prepare a solution a;

s2, dissolving the PPDCL in the formula amount in a solvent THF to prepare a solution b;

s3, dropwise adding the solution a into the solution b under the ice bath condition, and controlling the dropwise adding time to be about 60 minutes, so as to complete the preparation of the reaction solution;

s4, reacting the reaction solution for 80min under the ice bath condition, reacting for 7.5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s5, adding ethyl acetate and saturated small amount of saturated saline into the crude silane derivative liquid, extracting byproducts into a water phase, and removing the water phase to obtain an oil phase which is primarily purified; the extraction and purification operation is carried out for 4 times;

s6, adding anhydrous calcium sulfate into the oil phase subjected to primary purification, stirring, standing for 60min, and filtering the oil phase subjected to standing to obtain an oil phase subjected to secondary purification;

and S7, removing ethyl acetate in the secondarily purified oil phase through rotary evaporation, controlling the rotary evaporation temperature to be 75-80 ℃, and then drying in vacuum to remove the solvent to obtain the silane derivative pure product of the embodiment.

The purity of the products of examples 1 to 18 of the present application was measured by high performance liquid chromatography, and the yield of the products was calculated, with the results shown in Table 1 below.

TABLE 1 EXAMPLES 1 to 18 yields and product purity TABLE

As can be seen from the data in Table 1, the application adopts APTES, PPDCL and TEA to optimally feed in a molar ratio of 1:1:1.5, can effectively control the purity of the product, and can reduce the purity of the product by adopting other feeding ratios. It can be seen from the data in Table 1 that the temperature conditions used in the preparation of the reaction solution and the low-temperature reaction of the present application are relatively optimal at 0℃and the ice bath conditions are optimal, so that the reaction yield and the product purity can be effectively improved. As can be seen from the data in Table 1, when the reaction solution of the present application was prepared, the reaction yield increased with the increase of the dropping time, and after the dropping time exceeded 60 minutes, the reaction yield tended to decrease, so that the optimum dropping time was 60 minutes. As can be seen from the data in Table 1, the reaction time of the present application, the low temperature reaction time was controlled to be within 90 minutes, the normal temperature reaction time was controlled to be within 8 hours, and the reaction yield was not increased with the time beyond the above. As can be seen from the data in Table 1, in the purification operation of the present application, the number of extraction times is preferably controlled to 3 to 4, and after more than 4 times, the reaction yield cannot be effectively increased; after the anhydrous calcium sulfate is added, the standing time is controlled within 60 minutes, and after the standing time is exceeded, the product purity and the reaction yield can not be effectively improved. As can be seen from the data in Table 1, in the purification operation of the present application, the removal of ethyl acetate is best achieved by rotary evaporation, the rotary evaporation temperature is controlled to be 60-75 ℃ best, after exceeding the above temperature, the reaction yield is slightly reduced, and the reaction product is lost in the purification process.

The above embodiments are not intended to limit the scope of the present application, so: all equivalent changes in structure, shape and principle of the application should be covered in the scope of protection of the application.

Claims (10)

1. A silane derivative, wherein the silane derivative has the structural formula:

2. a process for the preparation of a silane derivative according to claim 1, characterized in that the process for the preparation of the silane derivative employs the following process route:

3. the method for producing a silane derivative according to claim 2, comprising the steps of:

s1, dissolving APTES in THF, and adding TEA to prepare a solution;

s2, dissolving PPDCL in THF to prepare a solution, and dropwise adding the solution prepared in the step S1 into the solution under the low-temperature condition to obtain a reaction solution;

s3, reacting the reaction solution obtained in the step S2 for more than 20min at low temperature, reacting for more than 5h at room temperature, and filtering the reaction solution to obtain crude silane derivative solution;

s4, adding ethyl acetate and saturated saline into the crude silane derivative liquid obtained in the step S3, and removing byproducts through extraction to obtain an oil phase which is primarily purified;

s5, adding anhydrous calcium sulfate into the oil phase obtained in the step S4, stirring, standing, and filtering the oil phase after standing to obtain a secondary purified oil phase;

s6, separating and removing ethyl acetate in the oil phase obtained in the step S5, and drying to remove the solvent to obtain a silane derivative pure product.

4. The process for producing a silane derivative according to claim 3, wherein in the steps S1 and S2, APTES, TEA and PPDCL are used in a molar ratio of 1:1.5:1.

5. The method for producing a silane derivative according to claim 3, wherein in the step S2, the dropping time of the solution prepared in the dropping step S1 is controlled to be 1h.

6. The method for producing a silane derivative according to claim 3, wherein in the step S2, the low temperature condition is an ice bath condition, the low temperature reaction time is controlled to be 30 to 90 minutes, and the normal temperature reaction time is controlled to be 6 to 8 hours.

7. The process for producing a silane derivative according to claim 3, wherein in the step S4, the extraction is performed by extracting the by-product into an aqueous phase and then separating the aqueous phase; the extraction operation is repeated 3 to 5 times.

8. The method for producing a silane derivative according to claim 3, wherein in the step S5, the time for the standing is controlled to be 0.5 to 1 hour.

9. The process for producing a silane derivative according to claim 3, wherein in step S6, the ethyl acetate is separated and removed by spin-evaporation at a temperature of 60 to 75 ℃.

10. Use of the silane derivative of claim 1 in the field of pharmaceutical and material preparation.