CN116162109A - Preparation method of tri (trimethylsilyl) phosphate - Google Patents
Preparation method of tri (trimethylsilyl) phosphate Download PDFInfo
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- CN116162109A CN116162109A CN202310141303.4A CN202310141303A CN116162109A CN 116162109 A CN116162109 A CN 116162109A CN 202310141303 A CN202310141303 A CN 202310141303A CN 116162109 A CN116162109 A CN 116162109A
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
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Abstract
本发明公开了一种三(三甲基硅基)磷酸酯的制备方法，该制备方法包括：使除去游离水的磷酸与三甲基烷氧基硅烷在保护气氛下进行回流反应；然后继续进行反应并蒸馏，在反应过程中蒸出反应产生的醇类物质和反应残余的三甲基烷氧基硅烷，三甲基烷氧基硅烷的沸点与醇类物质的沸点的差值的绝对值为0‑15℃；其中，控制蒸出过程分别在第一温度和第二温度下进行，第一温度至少可以使醇类物质蒸出，第二温度大于第一温度；本发明方法兼具反应原料不具危险性，副产物不污染环境及腐蚀设备、收率更高的优点，并且反应后副产物以及残留的反应底物基本可以被迅速除去，为后续提纯操作奠定了基础，可直接获得高纯度的目标产物。The invention discloses a preparation method of tris(trimethylsilyl)phosphate, which comprises: reflux reaction of phosphoric acid from which free water has been removed and trimethylalkoxysilane under a protective atmosphere; Reaction and distillation, during the reaction, the alcohols produced by the reaction and the residual trimethylalkoxysilane are distilled off, and the absolute value of the difference between the boiling point of the trimethylalkoxysilane and the boiling point of the alcohols is 0-15°C; wherein, the controlled steaming process is carried out at the first temperature and the second temperature respectively, the first temperature can at least make the alcohols evaporate, and the second temperature is higher than the first temperature; the method of the present invention has both reaction raw materials It is not dangerous, the by-products do not pollute the environment and corrode the equipment, and the yield is higher, and the by-products and residual reaction substrates after the reaction can basically be quickly removed, laying the foundation for subsequent purification operations, and can directly obtain high-purity target product.
Description
Technical Field
The invention relates to the technical field of lithium battery electrolyte additive synthesis, in particular to a preparation method of tri (trimethylsilyl) phosphate.
Background
Under the low-carbon large background, new energy becomes the main direction of global development, and the demand of lithium batteries is driven to continuously rise along with double harvest of the sales of new energy automobiles in China; meanwhile, the requirements for lithium batteries are continuously increased due to the rapid development of industries such as mobile phones, electric vehicles, electric tools, digital cameras and the like, and the development prospect of the lithium batteries is good. The method belongs to the production and consumption major countries of new energy batteries, plays a very high role in the worldwide battery market, and can greatly develop and produce the new energy batteries, not only promote the good development of related automobile industries in China and provide precondition guarantee, but also provide more lead technologies for transformation, upgrading, innovation and the like of various industries of new energy, and has very important effects and value.
The tri (trimethylsilyl) phosphate is used as an electrolyte additive of the lithium ion battery, and a low-resistance coating can be formed on the surface of the negative electrode, so that the self-discharge of the battery can be greatly inhibited, the low-temperature performance and the normal-temperature cycle performance of the battery can be obviously improved, the high-temperature performance is enhanced, the increase of the resistance of the battery can be inhibited, and the reduction of the capacity can be inhibited. Further, tris (trimethylsilyl) phosphate containing silicon and phosphorus atoms has flame retardant properties, which have been attracting more and more attention, and the demand is increasing.
The structural formula of the tris (trimethylsilyl) phosphate is as follows:
there have been many reports on the preparation method of tris (trimethylsilyl) phosphate, and the basic scheme is approximately as follows:
1. hexamethyldisilazane reacts with phosphate to generate tri (trimethylsilyl) phosphate and ammonia, and the tri (trimethylsilyl) phosphate and ammonia are rectified and purified to obtain a fine product; however, the method has high reaction temperature, large hexamethyldisilazane consumption and large ammonia release amount as a byproduct, and also has the problem of environmental pollution caused by ammonia, and the molar yield of the product is below 80%, so that the production cost is high;
2. the trimethyl chlorosilane reacts with the dihydrogen phosphate, the method has certain success in the yield, but has the problems of filtration and drying of hydrochloride and corrosion of byproduct hydrogen chloride and environmental pollution;
3. the technical scheme of the tri (trimethylsilyl) phosphate can be obtained by the reaction of hexamethyldisiloxane and phosphorus pentoxide, the yield is higher, but the phosphorus pentoxide is a high-toxicity and high-risk chemical product, the danger is also great, and the operation is not good.
In view of the problems with the above-mentioned solutions, patent application CN109503653a discloses a synthesis method of tri (trialkylsilyl) phosphate, which uses a reaction of trialkylsilyl amine with phosphoric acid, and although the tri (trialkylsilyl) phosphate is produced, nitrogen-containing compounds are also produced, and since the addition amount of the trialkylsilyl amine needs to be far excessive to ensure the conversion of phosphoric acid as much as possible, the post-reaction mixture finally obtained by the patent contains not only the target product but also the amounts of by-products and the trialkylsilyl amine, and even if a mode of distilling part of non-target products such as by-products and the like is adopted, a large amount of residues remain in the post-reaction mixture, which makes the post-purification operation more difficult, and a large amount of kettle residual liquid is obtained after the reduced pressure rectification is adopted; further, it was verified by analysis that its examples could not obtain its purported high content.
Disclosure of Invention
The invention aims to overcome one or more defects in the prior art, and provides an improved method for preparing tri (trimethylsilyl) phosphate, which has the advantages of no danger of reaction raw materials, no pollution of byproducts and corrosion equipment, and higher yield, and the byproducts and residual reaction substrates after the reaction can be basically and rapidly removed, thereby laying a foundation for subsequent purification operation, and directly obtaining a target product with high purity.
In order to achieve the above purpose, the invention adopts the following technical scheme: a method for preparing tris (trimethylsilyl) phosphate, the method comprising:
carrying out reflux reaction on phosphoric acid with free water removed and trimethylalkoxysilane in a protective atmosphere;
then continuing to react and distilling, and evaporating alcohol substances generated by the reaction and trimethylalkoxysilane remained by the reaction in the reaction process, wherein the absolute value of the difference between the boiling point of the trimethylalkoxysilane and the boiling point of the alcohol substances is 0-15 ℃; the alcohol material is distilled out at a first temperature and a second temperature, wherein the first temperature is used for evaporating the alcohol material, and the second temperature is higher than the first temperature.
According to some preferred aspects of the invention, the trimethylalkoxysilane is selected from at least one of the following compounds: (CH) 3 ) 3 Si-O-R, R is C 1-6 An alkyl group.
In some embodiments of the invention, R is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, neopentyl, and the like.
According to some preferred and specific aspects of the present invention, the trimethylalkoxysilane is one or more selected from trimethylmethoxysilane, trimethylethoxysilane, trimethylpropoxysilane, trimethylisopropoxysilane.
According to some preferred aspects of the invention, the trimethylalkoxysilane comprises at least trimethylethoxysilane.
According to the invention, the reaction process of phosphoric acid with trimethylalkoxysilane is schematically as follows:
the target product and monohydric alcohol are produced.
In some embodiments of the invention, the absolute value of the difference between the boiling point of the trimethylalkoxysilane and the boiling point of the alcohol is from 0 to 5 ℃.
In some embodiments of the invention, the absolute value of the difference between the boiling point of the trimethylalkoxysilane and the boiling point of the alcohol is from 5 to 10 ℃.
In some embodiments of the invention, the absolute value of the difference between the boiling point of the trimethylalkoxysilane and the boiling point of the alcohol is 10-15 ℃.
According to some preferred aspects of the invention, the absolute value of the difference between the second temperature and the first temperature is 20-50 ℃.
In some embodiments of the invention, the absolute value of the difference between the second temperature and the first temperature is 20-30 ℃.
In some embodiments of the invention, the absolute value of the difference between the second temperature and the first temperature is 30-35 ℃.
In some embodiments of the invention, the absolute value of the difference between the second temperature and the first temperature is 35-40 ℃.
In some embodiments of the invention, the absolute value of the difference between the second temperature and the first temperature is 40-45 ℃.
According to some preferred aspects of the invention, the temperature of the reflux reaction is 50-120 ℃, and the first temperature is 0-10 ℃ higher than the temperature of the reflux reaction.
In some embodiments of the invention, the temperature of the reflux reaction is 55-65 ℃, the first temperature is 4-6 ℃ higher than the temperature of the reflux reaction, and the absolute value of the difference between the second temperature and the first temperature is 30-45 ℃.
In some embodiments of the invention, the temperature of the reflux reaction is 75-85 ℃, the first temperature is 3-6 ℃ higher than the temperature of the reflux reaction, and the absolute value of the difference between the second temperature and the first temperature is 35-45 ℃.
In some embodiments of the invention, the temperature of the reflux reaction is 85-95 ℃, the first temperature is 3-6 ℃ higher than the temperature of the reflux reaction, and the absolute value of the difference between the second temperature and the first temperature is 25-40 ℃.
In some embodiments of the invention, the temperature of the reflux reaction is 100-110 ℃, the first temperature is 3-6 ℃ higher than the temperature of the reflux reaction, and the absolute value of the difference between the second temperature and the first temperature is 20-30 ℃.
In the invention, the arrangement of the first temperature and the second temperature not only can promote the reaction forward direction, but also can lead most of residual reaction raw materials and byproducts to be distilled out maximally, thereby being beneficial to the reduction of the subsequent purification difficulty and being more beneficial to obtaining the high-purity target product.
According to some preferred aspects of the invention, the protective atmosphere is formed by introducing a protective gas, the protective gas being nitrogen and/or argon, the protective gas being introduced at a rate of 1-10mL/min and the pressure being controlled at 99-105kPa.
According to some preferred aspects of the invention, the molar ratio of the phosphoric acid to the trimethylalkoxysilane is 1:3-20.
Further, the molar ratio of the phosphoric acid with the free water removed to the trimethylalkoxysilane is 1:4-8.
According to some preferred aspects of the invention, embodiments of the preparation method comprise:
adding trimethylalkoxysilane into phosphoric acid with free water removed, stirring and heating under protective atmosphere until the temperature rises to reflux reaction temperature and the reflux reaction is maintained, wherein the reaction time is t1;
continuously reacting and adopting a reactive distillation mode to distill out alcohol substances generated by the reaction and trimethyl alkoxy silane remained by the reaction in the reaction process, wherein the distillation process is controlled to be carried out at a first temperature for t2, and the distillation process is carried out at a second temperature until no liquid is discharged, and then the distillation process is carried out at room temperature under reduced pressure;
t1 is 2 to 15h and t2 is 1 to 5h respectively.
In some embodiments of the invention, the method of preparing the phosphoric acid to remove free water comprises: the phosphoric acid from which the free water has been removed is obtained by mixing the dehydrating agent with an aqueous phosphoric acid solution, heating the mixture under stirring under the protection of a protective gas (for example, nitrogen, argon, or the like), and removing the free water by azeotropic distillation.
In some embodiments of the invention, the dehydrating agent is an organic solvent that is not miscible with water.
Further, the dehydrating agent is one or a combination of more selected from toluene, xylene, hexamethyldisiloxane and dichloroethane.
In some embodiments of the invention, the phosphoric acid in the phosphoric acid aqueous solution is 40% -95% by mass. According to a specific aspect of the invention, industrial concentrated phosphoric acid can be selected, wherein the mass percentage is 85%.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
according to the invention, by using trimethylalkoxysilane and phosphoric acid as reaction raw materials, the inventor can obtain the target product tri (trimethylsilyl) phosphate with high yield, and can not generate by-products polluting the environment or corroding equipment in the reaction process, so that the generation of non-environment-friendly or corrosive substances such as ammonia gas, hydrogen chloride and ammonia compounds in the prior art is avoided, particularly, the by-products and excessive trimethylalkoxysilane can be removed in the reactive distillation process, the conversion rate is greatly improved, the subsequent purification difficulty is greatly reduced, and the by-products and the residual massive reaction raw materials are basically removed, so that the reaction mixture obtained after the reaction is almost the target product, and the extremely high-purity tri (trimethylsilyl) phosphate can be obtained through reduced pressure rectification, and can be directly used as the electrolyte additive of the lithium ion battery without additional purification process.
Detailed Description
The above-described aspects are further described below in conjunction with specific embodiments; it should be understood that these embodiments are provided to illustrate the basic principles, main features and advantages of the present invention, and that the present invention is not limited by the scope of the following embodiments; the implementation conditions employed in the examples may be further adjusted according to specific requirements, and the implementation conditions not specified are generally those in routine experiments.
All starting materials are commercially available or prepared by methods conventional in the art, not specifically described in the examples below.
Example 1
The present example provides a process for the preparation of tris (trimethylsilyl) phosphate comprising the steps of:
580g of 85% phosphoric acid aqueous solution and 1700g of hexamethyldisiloxane are added into a reaction bottle, magnetic stirring, a water separator and a reflux condenser tube are matched, heating is carried out, cooling water of the reflux condenser tube is started, the temperature is increased to 120+/-5 ℃ in a nitrogen atmosphere, reflux water removal is carried out for 8 hours under normal pressure, and the temperature is reduced to room temperature.
2600g of trimethylmethoxysilane is added into the dehydrated phosphoric acid, stirring and heating reaction are carried out under nitrogen atmosphere, reflux reaction is carried out for 5 hours at 60+/-5 ℃, a distillation device is switched, methanol and the like generated during reaction are distilled off, and the distillation time is controlled to be 5 hours. The distillation temperature is controlled at 65+/-5 ℃ at the beginning, the temperature at the later stage of reactive distillation is controlled at 105+/-5 ℃, the reaction is finished after liquid is not discharged, and the temperature is reduced to room temperature.
The reaction liquid is subjected to vacuum rectification and purification, and fractions of 126-128 ℃/30mmHg are collected, thereby obtaining 1332g of tri (trimethylsilyl) phosphate with the purity of 99.91 percent, and the yield is 84.2 percent.
Comparative example 1
The phosphoric acid water removal operation was the same as in example 1.
Adding 2600g of trimethylmethoxysilane into the dehydrated phosphoric acid, switching to a distillation device, stirring and heating under nitrogen atmosphere to react while distilling off generated methanol, and the like, wherein the distillation temperature is controlled at 65+/-5 ℃ at the beginning, the temperature is controlled at 105+/-5 ℃ at the later stage of reactive distillation, and the reaction is finished after liquid is not discharged and the temperature is reduced to room temperature.
The reaction liquid is subjected to vacuum rectification and purification, and fractions of 126-128 ℃/30mmHg are collected, so that 1149g of tri (trimethylsilyl) phosphate with the purity of 99.92 percent is obtained, and the yield is 72.6 percent.
Example 2
Adding 580g of 85% phosphoric acid aqueous solution and 1800g of toluene into a reaction bottle, magnetically stirring, a water separator and a reflux condenser, heating to raise the temperature, starting the reflux condenser to cool water, raising the temperature to 110+/-5 ℃ in nitrogen atmosphere, refluxing and dehydrating for 8 hours under normal pressure, and cooling to room temperature.
2900g of trimethylethoxysilane is added into the dehydrated phosphoric acid, stirring and heating reaction are carried out under the nitrogen atmosphere, reflux reaction is carried out for 5 hours at 80+/-5 ℃, a distillation device is switched, ethanol and the like generated during the reaction are distilled out, and the distillation time is controlled to be 5 hours. The distillation temperature is controlled at 85+/-5 ℃ at the beginning, the temperature at the later stage of reactive distillation is controlled at 125+/-5 ℃, the reaction is finished after liquid is not discharged, and the temperature is reduced to room temperature.
The reaction liquid is subjected to vacuum rectification and purification, and fractions of 126-128 ℃/30mmHg are collected, thus 1345g of tri (trimethylsilyl) phosphate with the purity of 99.94 percent is obtained, and the yield is 85.0 percent.
Example 3
The phosphoric acid water removal operation was the same as in example 1.
3500g of trimethylethoxysilane is added into the dehydrated phosphoric acid, stirring and heating reaction are carried out under nitrogen atmosphere, reflux reaction is carried out for 5 hours at 80+/-5 ℃, the reaction is switched to a distillation device, ethanol and the like generated during the reaction are distilled out, and the distillation time is controlled to be 5 hours. The distillation temperature is controlled at 85+/-5 ℃ at the beginning, the temperature at the later stage of reactive distillation is controlled at 125+/-5 ℃, the reaction is finished after liquid is not discharged, and the temperature is reduced to room temperature.
The reaction liquid is subjected to vacuum rectification and purification, and fractions of 126-128 ℃/30mmHg are collected, so that 1371g of tri (trimethylsilyl) phosphate with the purity of 99.92 percent is obtained, and the yield is 86.6 percent.
Example 4
The phosphoric acid water removal operation was the same as in example 1.
3500g of isopropyl trimethyl silane is added into the dehydrated phosphoric acid, stirring and heating reaction are carried out under the nitrogen atmosphere, reflux reaction is carried out for 7 hours at 90+/-5 ℃, the reaction is switched to a distillation device, isopropanol and the like are distilled out while the reaction is carried out, and the distillation time is controlled to be 6 hours. The distillation temperature is controlled at 95+/-5 ℃ at the beginning, the temperature at the later stage of reactive distillation is controlled at 130+/-5 ℃, the reaction is finished after liquid is not discharged, and the temperature is reduced to room temperature.
The reaction liquid is subjected to vacuum rectification and purification, and fractions of 126-128 ℃/30mmHg are collected, thereby obtaining 1334g of tri (trimethylsilyl) phosphate with the purity of 99.93 percent, and the yield is 84.3 percent.
Example 5
The phosphoric acid water removal operation was the same as in example 2.
3500g of propoxytrimethylsilane is added into the dehydrated phosphoric acid, the mixture is stirred and heated to react under nitrogen atmosphere, the reflux reaction is kept at 105+/-5 ℃ for 7 hours, the mixture is switched to a distillation device, propanol and the like are distilled out while the reaction is carried out, and the distillation time is controlled to be 6 hours. The distillation temperature is controlled at 110+/-5 ℃ at the beginning, the temperature at the later stage of reactive distillation is controlled at 135+/-5 ℃, the reaction is finished after no liquid is discharged, and the temperature is reduced to room temperature.
The reaction liquid is subjected to vacuum rectification and purification, and fractions of 126-128 ℃/30mmHg are collected, thus 1347g of tri (trimethylsilyl) phosphate with the purity of 99.92 percent is obtained, and the yield is 85.1 percent.
The above embodiments are provided to illustrate the technical concept and features of the present invention and are intended to enable those skilled in the art to understand the content of the present invention and implement the same, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
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2023
- 2023-02-21 CN CN202310141303.4A patent/CN116162109A/en active Pending
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