CN111269077A - Synthetic method of 2,3,4, 5-tetramethyl-p-xylene ring dimer - Google Patents
Synthetic method of 2,3,4, 5-tetramethyl-p-xylene ring dimer Download PDFInfo
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Abstract
The invention discloses a synthetic method of 2,3,4, 5-tetramethyl-p-xylene ring dimer, and relates to the field of preparation of parylene dimer, wherein 2,3,4,5, 6-pentamethyl benzyl chloride and trimethylamine are used as raw materials to react to generate 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride, and then the 2,3,4, 5-tetramethyl-p-xylene ring dimer is generated by reacting the 2,3,4, 5-pentamethyl benzyl trimethyl ammonium chloride with sodium hydroxide, a catalyst, a solvent and the like.
Description
Technical Field
The invention relates to a preparation method of a parylene dimer, in particular to a preparation method of a 2,3,5, 6-tetramethyl-p-xylene ring dimer.
Background
Parylene is a novel special polymer material with excellent properties such as water resistance, corrosion resistance, toughness, transparency, electrical insulation and the like. Its trade name is parylene (parylene). A series of parylene derivatives containing different functional groups are obtained by modifying hydrogen on a benzene ring or a methylene, and each derivative has unique and excellent performance. Mainly comprises parylene N, parylene C, parylene D, parylene F-VT4 and parylene F-AF 4.
The preparation of parylene is that a layer of polymer (parylene) coating is directly formed on the surface of a device by vacuum vapor deposition of a corresponding cyclic dimer. The processing mode can form a layer of uniform, compact and ultrathin film on the surface of the device, is very suitable for surface treatment of tiny and precise devices, and is widely applied to the high and new technical fields of electronic circuit components, sensors, integrated circuits and the like. Due to the unique biocompatibility and low toxicity, the compound also has wide application prospect in the fields of medical instruments, biotechnology and the like. The properties of parylene vary, for example: the parylene N powder has good waterproof and barrier properties, low price and the widest application, but has poor strength and poor high temperature resistance; compared with the parylene N, the parylene C and the parylene D are more resistant to high temperature but have weaker barrier property and higher price; the parylene F-VT4 and the parylene F-AF4 have strong high temperature resistance and ultraviolet resistance, good barrier property, expensive price and larger processing difficulty, and limit the application range of the materials. The appropriate parylene is chosen for use for different scenarios. However, in terms of overall performance, parylene C and parylene D are superior to parylene N. However, the parylene C and the parylene D contain halogen, and can be released in the gradual aging process after being used, so that the environment is polluted, the human body is injured, and the use is limited in certain areas with strict requirements on environmental protection, safety and the like. In this case, poly-2, 3,5, 6-tetramethylparaxylene, parylene, appears as a substitute for C and D. Since the parylene is prepared from the corresponding cyclic dimer, there is an urgent need to develop a synthetic method of 2,3,5, 6-tetramethyl-p-xylene cyclic dimer with low cost, high yield and little environmental pollution.
Disclosure of Invention
In order to solve the existing problems and popularize the application of parylene, the invention aims to provide a simple, high-efficiency and low-cost synthetic method of 2,3,5, 6-tetramethyl-p-xylene ring dimer.
In order to achieve the above objects, the present invention provides a method for preparing 2,3,4, 5-tetramethyl-p-xylene ring dimer, the reaction formula of which is shown as follows:
the invention provides a method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer, which comprises the following steps:
a method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer comprises the following steps;
a. the method comprises the step of reacting a trimethylamine aqueous solution with the concentration of 33% and 2,3,4,5, 6-pentamethyl benzyl chloride at the molar ratio of 2:1 to 1:1 at the temperature of 40-80 ℃ to generate the 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride.
b. 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride is used as a raw material to react with strong base, a catalyst, a solvent and an additive at a temperature of 60-120 ℃ for 24 hours to obtain a crude product of 2,3,4, 5-tetramethyl p-xylene ring dimer.
And c, recrystallizing the 2,3,4, 5-tetramethyl-p-xylene ring dimer crude product by using ethanol to obtain a 2,3,4, 5-tetramethyl-p-xylene ring dimer pure product with the purity of more than 99.5 percent.
In a further technical scheme, the reaction temperature in the step a is preferably 40-60 ℃.
In a further technical scheme, the molar ratio of the trimethylamine aqueous solution with the concentration of 33% in the step a to the 2,3,4,5, 6-pentamethylbenzyl chloride is preferably 0.05:1 to 0.01: 1.
In a further technical scheme, the strong base used in the step b adopts sodium hydroxide or potassium hydroxide, preferably sodium hydroxide,
in a further technical scheme, the concentration of the strong alkali is 20-50%, preferably 30-40%.
According to a further technical scheme, the mole ratio of the strong alkali to the 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride in the step b is 10: 1 to 5:1, preferably 8:1 to 6: 1.
According to a further technical scheme, in the step b, one of PEG400, crown ether and tetrabutylammonium bromide is adopted as a catalyst, and PEG400 is preferred.
In a further technical scheme, the mole ratio of the catalyst to the 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride is 0.001:1 to 0.1:1, preferably 0.05:1 to 0.01: 1.
In a further technical scheme, the additive used in the step b is one of sodium sulfite, sodium bisulfite and phenothiazine, and preferably the sodium bisulfite is adopted.
In a further technical scheme, the solvent in the step b is one of toluene, xylene, ethanol, dioxane, dimethyl sulfoxide and tetrahydrofuran, and toluene or xylene is preferred.
In a further technical scheme, the reaction temperature in the step b is preferably 80-100 ℃.
Drawings
FIG. 1 is a schematic diagram of the reaction scheme of the present invention.
The synthesis method comprises two steps:
firstly, 2,3,4,5, 6-pentamethyl benzyl chloride and trimethylamine aqueous solution are used as raw materials, water is used as a solvent, and 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride is generated through reaction.
And secondly, reacting 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride, sodium hydroxide, an organic solvent, a catalyst and an additive serving as raw materials to generate the 2,3,5, 6-tetramethyl p-xylene ring dimer.
Examples
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described below by way of specific embodiments. It is to be understood that such description is merely illustrative and not intended to limit the scope of the present invention. Moreover, in the following description, descriptions of well-known structures and techniques are omitted so as to not unnecessarily obscure the concepts of the present invention.
First step example
Example 1
196g of 2,3,4,5, 6-pentamethyl benzyl chloride is added into a 500ml three-neck flask, 188g of a 33% trimethylamine aqueous solution is added into the flask dropwise under mechanical stirring, the reaction temperature is kept at 40-60 ℃ in the dropwise adding process, and the dropwise adding is carried out for 3 hours. After the completion of the dropwise addition, the reaction was continued for 1 hour. Then, water in the reaction liquid is distilled out to obtain 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid. After further drying, 249g of solid was obtained in 97.6% yield.
Example 2
196g of 2,3,4,5, 6-pentamethyl benzyl chloride is added into a 500ml three-neck flask, 160g of ethanol is added, 188g of a 33% trimethylamine aqueous solution is added into the flask dropwise under mechanical stirring, the reaction temperature is ensured to be 40-60 ℃ in the dropwise adding process, and the dropwise adding is carried out for 3 hours. After the completion of the dropwise addition, the reaction was continued for 1 hour. Then, water and a solvent in the reaction liquid are distilled off to obtain 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid. After further drying, 245g of a solid was obtained with a yield of 96.1%.
Example 3
196g of 2,3,4,5, 6-pentamethyl benzyl chloride is added into a 500ml three-neck flask, 320g of ethanol is added, 188g of 33 percent trimethylamine aqueous solution is added into the flask under mechanical stirring, the reaction temperature is ensured to be 40-60 ℃ in the dropping process, and the dropping is carried out for 3 hours. After the completion of the dropwise addition, the reaction was continued for 1 hour. Then, water and a solvent in the reaction liquid are distilled off to obtain 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid. After further drying, 241g of solid was obtained with a yield of 94.5%.
Example 4
196g of 2,3,4,5, 6-pentamethyl benzyl chloride is added into a 500ml three-neck flask, 320g of ethanol is added, 188g of 33 percent trimethylamine aqueous solution is added into the flask under mechanical stirring, the reaction temperature is ensured to be 40-60 ℃ in the dropping process, and the dropping is carried out for 3 hours. After the completion of the dropwise addition, the reaction was continued for 1 hour. Then, water and a solvent in the reaction liquid are distilled off to obtain 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid. After further drying 240g of solid was obtained with a yield of 94.1%.
Example 5
196g of 2,3,4,5, 6-pentamethyl benzyl chloride is added into a 500ml three-neck flask, 160g of ethyl acetate is added, 188g of 33 percent trimethylamine aqueous solution is added into the flask dropwise under mechanical stirring, the reaction temperature is ensured to be 40-60 ℃ in the dropwise adding process, and the dropwise adding is carried out for 3 hours. After the completion of the dropwise addition, the reaction was continued for 1 hour. Then, water and a solvent in the reaction liquid are distilled off to obtain 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid. After further drying, 232g of solid was obtained with a yield of 92.8%.
Example 6
Adding 196kg of 2,3,4,5, 6-pentamethyl benzyl chloride into a 500L reaction kettle, weighing 188kg of 33% trimethylamine aqueous solution, adding into a dropwise adding tank, dropwise adding into the reaction kettle under mechanical stirring, and ensuring the reaction temperature to be 40-60 ℃ in the dropwise adding process for 5 hours. After the completion of the dropwise addition, the reaction was continued for 1 hour. Then, water and a solvent in the reaction liquid are distilled off to obtain 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid. After further drying, 248kg of solid was obtained with a yield of 97.2%.
Second step of
Example 1
A3L three-neck flask is provided with a thermometer and a condenser and is mechanically stirred, 640g of water is weighed, 320g of sodium hydroxide solid is added, 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid, 1L of toluene and a catalyst are added, the temperature is raised to 80-100 ℃ for reaction, and the temperature is kept for reaction for 24 hours. Separating an upper organic layer after the reaction is finished, washing with a small amount of water, filtering, evaporating the solvent to obtain a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 132g of a product, wherein the yield is 82.5 percent, and the purity is more than 99.5 percent.
Example 2
A3L three-neck flask is provided with a thermometer and a condenser and is mechanically stirred, 640g of water is weighed, 320g of sodium hydroxide solid is added, 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid, 1L of dimethylbenzene and a catalyst are added, the temperature is increased to 80-100 ℃ after the reaction, and the reaction is carried out for 24 hours under the condition of heat preservation. Separating an upper organic layer after the reaction is finished, washing with a small amount of water, filtering, evaporating the solvent to obtain a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 121g of a product, wherein the yield is 75.6 percent, and the purity is more than 99.5 percent.
Example 3
A3L three-neck flask is provided with a thermometer and a condenser and is mechanically stirred, 480g of water is weighed, 240g of sodium hydroxide solid is added, 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid, 1L of toluene and a catalyst are added, the temperature is increased to 80-100 ℃ for reaction, and the temperature is kept for reaction for 24 hours. Separating an upper organic layer after the reaction is finished, washing with a small amount of water, filtering, evaporating the solvent to obtain a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 123g of a product, wherein the yield is 76.8 percent, and the purity is more than 99.5 percent.
Example 4
A thermometer and a condenser are arranged on a 3L three-neck flask, mechanical stirring is carried out, 640g of water is weighed, 320g of sodium hydroxide solid is added, 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid, 1L of dioxane and a catalyst are added, the temperature is increased to 80-100 ℃ after reaction, and the temperature is kept for 24 hours. Separating an upper organic layer after the reaction is finished, washing with a small amount of water, filtering, evaporating the solvent to obtain a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 123g of a product, wherein the yield is 76.8 percent, and the purity is more than 99.5 percent.
Example 5
A3L three-neck flask is provided with a thermometer and a condenser and is mechanically stirred, 640g of water is weighed, 320g of sodium hydroxide solid is added, 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid, 1L of ethanol and a catalyst are added, the temperature is increased to 80-100 ℃ after the reaction, and the reaction is carried out for 24 hours under the condition of heat preservation. Separating an upper organic layer after the reaction is finished, washing with a small amount of water, filtering, evaporating the solvent to obtain a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering, and drying to obtain 23g of a product, wherein the yield is 14.3%, and the purity is more than 99.5%.
Example 6
A3L three-neck flask is provided with a thermometer and a condenser and is mechanically stirred, 640g of water is weighed, 448g of potassium hydroxide solid is added, 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid, 1L of toluene and a catalyst are added, the temperature is raised to 80-100 ℃ for reaction, and the temperature is kept for reaction for 24 hours. Separating an upper organic layer after the reaction is finished, washing with a small amount of water, filtering, evaporating the solvent to obtain a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 114g of a product, wherein the yield is 71.2 percent, and the purity is more than 99.5 percent.
Example 7
192kg of 33% sodium hydroxide solution is pumped into a 500L reaction kettle, 51kg of 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid is weighed and added into the reaction kettle in batches, and after the addition is finished, 200L of toluene is pumped into the reaction kettle, and then the catalyst is added. After the addition, the temperature is raised, the internal temperature in the reaction kettle is raised to 80-100 ℃ within two hours, and the reaction is carried out for 24 hours under the condition of heat preservation. Trimethylamine gas generated in the reaction process is absorbed by water mist and then recycled. After the reaction, the aqueous layer and the organic layer were separated, and the aqueous layer was slightly concentrated and desalted. The concentration was adjusted to about 33% and the application was continued. Washing the organic layer with a small amount of water, filtering, evaporating the solvent, recycling the solvent, obtaining a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 26.8kg of a product, wherein the yield is 83.7 percent, and the purity is more than 99.5 percent.
Example 8
192kg of 33% sodium hydroxide solution is pumped into a 500L reaction kettle, 51kg of 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride solid is weighed and added into the reaction kettle in batches, and after the addition is finished, 200L of toluene is pumped into the reaction kettle, and then the catalyst and 0.5kg of sodium sulfite are added. After the addition, the temperature is raised, the internal temperature in the reaction kettle is raised to 80-100 ℃ within two hours, and the reaction is carried out for 24 hours under the condition of heat preservation. Trimethylamine gas generated in the reaction process is absorbed by water mist and then recycled. After the reaction, the aqueous layer and the organic layer were separated, and the aqueous layer was slightly concentrated and desalted. The concentration was adjusted to about 33% and the application was continued. Washing the organic layer with a small amount of water, filtering, evaporating the solvent, recycling the solvent, obtaining a crude product of the 2,3,5, 6-tetramethyl-p-xylene ring dimer, recrystallizing the crude product with ethanol, filtering and drying to obtain 27.3kg of a product, wherein the yield is 85.3 percent, and the purity is more than 99.5 percent.
Claims (13)
1. A method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer is characterized by comprising the following specific steps;
a. adopting a trimethylamine aqueous solution with the concentration of 33 percent and 2,3,4,5, 6-pentamethyl benzyl chloride with the molar ratio of 2:1 to 1:1 to react at the temperature of 40-80 ℃ to generate 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride;
b. taking 2,3,4,5, 6-pentamethyl benzyl trimethyl ammonium chloride as a raw material, and reacting the raw material with strong base, a catalyst, a solvent and an additive at a temperature of between 60 and 120 ℃ for 24 hours to obtain a 2,3,4, 5-tetramethyl p-xylene ring dimer crude product;
and c, recrystallizing the 2,3,4, 5-tetramethyl-p-xylene ring dimer crude product to obtain a 2,3,4, 5-tetramethyl-p-xylene ring dimer pure product with the purity of more than 99.5 percent.
2. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the reaction temperature in step a is preferably 40-60 ℃.
3. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the molar ratio of the aqueous trimethylamine solution with a concentration of 33% to the 2,3,4,5, 6-pentamethyl benzyl chloride solution in the step a is preferably 0.05:1 to 0.01: 1.
4. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the strong base in step b is sodium hydroxide or potassium hydroxide, preferably sodium hydroxide.
5. The method of claim 4, wherein the concentration of the strong base is 20% to 50%, preferably 30% to 40%.
6. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the molar ratio of the strong base to the 2,3,4,5, 6-pentamethylbenzyltrimethylammonium chloride in the step b is 10: 1 to 5:1, preferably 8:1 to 6: 1.
7. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the catalyst in step b is one of PEG400, crown ether and tetrabutylammonium bromide, preferably PEG 400.
8. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the molar ratio of the catalyst to the 2,3,4,5, 6-pentamethylbenzyltrimethylammonium chloride is 0.001:1 to 0.1:1, preferably 0.05:1 to 0.01: 1.
9. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the additive used in step b is one of sodium sulfite, sodium bisulfite and phenothiazine, preferably sodium bisulfite.
10. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the solvent in step b is one of toluene, xylene, ethanol, dioxane, dimethyl sulfoxide and tetrahydrofuran, preferably toluene or xylene.
11. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the reaction temperature in step b is preferably 80-100 ℃.
12. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the temperature rise time in step b is 1-4 hours, preferably 1.5-2 hours.
13. The method for synthesizing 2,3,4, 5-tetramethyl-p-xylene ring dimer according to claim 1, wherein the recrystallization solvent in step c is one of ethanol, methanol, acetone, toluene and ethyl acetate, preferably ethanol or acetone.
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| US11671763B2 (en) | 2021-02-24 | 2023-06-06 | Shure Acquisition Holdings, Inc. | Parylene electret condenser microphone backplate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11671763B2 (en) | 2021-02-24 | 2023-06-06 | Shure Acquisition Holdings, Inc. | Parylene electret condenser microphone backplate |
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