CN107216232A - A kind of Parylene F preparation method - Google Patents
A kind of Parylene F preparation method Download PDFInfo
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- CN107216232A CN107216232A CN201710420502.3A CN201710420502A CN107216232A CN 107216232 A CN107216232 A CN 107216232A CN 201710420502 A CN201710420502 A CN 201710420502A CN 107216232 A CN107216232 A CN 107216232A
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- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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Abstract
The invention discloses a kind of Parylene F preparation method, 4 methyl tetrafluoro benzyl chlorides are prepared by 4 methyl tetrafluorobenzyl alcohols and thionyl chloride under rational working environment, 4 methyl tetrafluoro quaternary amines are prepared by 4 methyl tetrafluoro benzyl chlorides and methylamine water solution, Parylene F is prepared by 4 methyl tetrafluoro quaternary amines and toluene system solution.The invention provides a kind of Parylene F preparation method, it can be prepared by by three chemical reactions, raw material is obtained simply and price is relatively low, is a kind of very cost-effective preparation method.
Description
Technical field
The present invention relates to a kind of preparation method of speciality polymer material, more particularly to a kind of Parylene F preparation side
Method.
Background technology
Parylene, which is that one kind is tough and tensile, transparent, to be had excellent electrical insulation capability, resistance to chemical corrosion and can uniformly apply
Deposited speciality polymer material, the classification one that Parylene commodity have obtained large-scale commercial applications application has four kinds：N powder, C powder, D powder, F
Powder.Four kinds of Parylene powder have respective advantage, and wherein Parylene F heat endurance is best.As the mankind resist high-temperature material
The need for it is more and more, Parylene F demand is also more vigorous.But the method for being restricted synthesis Parylene F at present, Parylene
F's is expensive.
In Patent No. ZL200510023332.2 patent of invention, it is noted that a kind of preparation side of dimeric p-xylene
Method, mainly using methanesulfonic acid（To front three silicon methyl ptfe benzyl）Ester alkane prepares Parylene F, and yield can reach 80%, but should
Raw material is difficult to obtain, and price is also costly, is difficult finally industrialization.
The content of the invention
In order to overcome the above-mentioned deficiencies of the prior art, the invention provides a kind of Parylene F preparation method.
To reach above-mentioned purpose, the technical solution adopted for the present invention to solve the technical problems is：
A kind of Parylene F preparation method, the preparation method is specific as follows：
（1）19g 4- methyl tetrafluorobenzyl alcohol and the 150mL dichloromethane dried are placed in two-mouth bottle in the temperature less than 0 DEG C
The lower cooling of degree is reacted, and dropwise addition 2~5 is dripped DMF catalysis and stirred, and the thionyl chloride that 11.5~13.5g is added dropwise afterwards is stirred, and
Reacted with the original solution in two-mouth bottle, reactive chemistry formula is：
（2）By step（1）In mixed solution persistently stir after 1 hour and to be concentrated under reduced pressure by rotating instrument, after 10~30min of cooling
Petroleum ether and stirring is added, white powdery solids 4- methyl tetrafluoro benzyl chlorides are filtrated to get；
（3）By step（2）In the 4- methyl tetrafluoro benzyl chlorides that prepare be placed in 100mL absolute ethyl alcohols in two-mouth bottle, using magnetic
Power stirs, and 25ml methylamine water solutions are added dropwise at room temperature, is then heated to 60 DEG C and is reacted with the original solution in two-mouth bottle
24h, reactive chemistry formula is：
（4）By step（3）The solution decompression that middle reaction is completed is evaporated, and evaporated material includes the first that water, ethanol, unreacted are completed
Amine, adds 25ml dimethylbenzene afterwards, is stirred vigorously after 30min and filters, the filter cake after filtering is washed with acetone, and is placed on true
Drying obtains white powdery solids 4- methyl tetrafluoro quaternary amines in empty drying box；
（5）20g sodium hydroxides, 30ml DMSO, 150ml toluene are placed in there-necked flask, stirring and being heated to 80 DEG C obtains
Toluene system solution；
（6）With 150ml water dissolving step（4）In the 4- methyl tetrafluoro quaternary amines that prepare, and be at the uniform velocity added dropwise in 3 hours
Into toluene system solution, uniform stirring 24h and react afterwards, reactive chemistry formula is：
（7）By step（6）In solution temperature be reduced to room temperature, then separation the superiors toluene layer is extracted with 50mL toluene
DMSO and water layer, combining methylbenzene layer, add anhydrous sodium sulfate, afterwards dry filter and evaporated under reduced pressure filtrate, add 20mL
Ethanol stirs 15 minutes in the solid after being evaporated, is filtrated to get white crystalline solid Parylene F.
Further, the step（1）The rate of addition of middle thionyl chloride is 25g/h.
Further, the step（3）The rate of addition of middle methylamine water solution is 25ml/h.
Further, the step（1）, step（3）And step（6）Solution after middle hybrid reaction is carried out by TLC plates
The measure of solution impurity and content.
Further, the step（2）In nuclear-magnetism number of the 4- methyl tetrafluoro benzyl chlorides through magnetic resonance detection for preparing
According to for1H NMR (400 MHz, CDCl3) δ 2.25(s,3H), 4.63(s, 2H)；The step（4）In prepare
Nuclear magnetic data of the 4- methyl tetrafluoro quaternary amines through magnetic resonance detection be1H NMR (400 MHz, DMSO) δ 2.32(s,
3H), 3.17(s,9H), 4.72(s, 2H)；The step（7）In cores of the Parylene F through magnetic resonance detection for preparing
Magnetic data is1H NMR (400 MHz, DMSO) δ 3.25。
Due to the utilization of above-mentioned technical proposal, the present invention has following beneficial effect compared with prior art：
（1）The invention provides a kind of Parylene F preparation method, it can be prepared by by three chemical reactions, raw material obtains letter
List and price is relatively low, is a kind of very cost-effective preparation method.
（2）The rate of addition of thionyl chloride is 25g/h in preparation process, and the rate of addition of methylamine water solution is 25ml/h,
Rationally control rate of addition can guarantee that reaction is more abundant, and the preparation efficiency of product is higher.
（3）Monitored in real time by TLC plates after the completion of solution reaction, for judging whether solution reaction is complete；Simultaneously
The product prepared is subjected to nuclear magnetic resonance, whether obtained product is judged as target product with the nuclear magnetic data measured, it is whole
Individual process makes preparation be carried out simultaneously with detection, and Parylene F preparation quality is effectively ensured.
Embodiment
With reference to specific embodiment, present disclosure is described in further detail：
Embodiment 1
A kind of Parylene F preparation method, the preparation method is specific as follows：
（1）19g 4- methyl tetrafluorobenzyl alcohol and the 150mL dichloromethane dried are placed in two-mouth bottle in the temperature less than 0 DEG C
The lower cooling of degree is reacted, and dropwise addition 2~5 is dripped DMF catalysis and stirred, and 11.5~12.2g is added dropwise with 25g/h rate of addition afterwards
Thionyl chloride stirring, and with two-mouth bottle original solution react, and by TLC plates detect raw material reaction finish, reactive chemistry
Formula is：
（2）By step（1）In mixed solution persistently stir after 1 hour and to be concentrated under reduced pressure by rotating instrument, after 10~30min of cooling
Petroleum ether and stirring is added, white powdery solids 4- methyl tetrafluoro benzyl chlorides, the average weight of the 4- methyl tetrafluoro benzyl chlorides is filtrated to get
Measure as 18.5g, now preparation efficiency is 89%, nuclear magnetic data of the 4- methyl tetrafluoro benzyl chlorides through magnetic resonance detection prepared
For1H NMR (400 MHz, CDCl3) δ 2.25(s,3H), 4.63(s, 2H)；
（3）By step（2）In the 4- methyl tetrafluoro benzyl chlorides that prepare be placed in 100mL absolute ethyl alcohols in two-mouth bottle, use
Magnetic agitation is uniform, and 25ml methylamine water solutions are added dropwise with 25ml/h rate of addition at room temperature, is then heated to 60 DEG C and with two
Original solution reaction 24h in mouth bottle, and detect that raw material reaction is finished by TLC plates, reactive chemistry formula is：
（4）By step（3）The solution decompression that middle reaction is completed is evaporated, and evaporated material includes the first that water, ethanol, unreacted are completed
Amine, adds 25ml dimethylbenzene afterwards, is stirred vigorously after 30min and filters, the filter cake after filtering is washed with acetone, and is placed on true
Drying obtains white powdery solids 4- methyl tetrafluoro quaternary amines in empty drying box, the 4- methyl tetrafluoros quaternary amine warp prepared
The nuclear magnetic data of magnetic resonance detection is1H NMR (400 MHz, DMSO) δ 2.32(s,3H), 3.17(s,9H), 4.72
(s, 2H)；
（5）20g sodium hydroxides, 30ml DMSO, 150ml toluene are placed in there-necked flask, stirring and being heated to 80 DEG C obtains
Toluene system solution；
（6）With 150ml water dissolving step（4）In the 4- methyl tetrafluoro quaternary amines that prepare, and be at the uniform velocity added dropwise in 3 hours
Into toluene system solution, uniform stirring 24h and react afterwards, and detect that raw material reaction is finished by TLC plates, reactive chemistry formula
For：
（7）By step（6）In solution temperature be reduced to room temperature, then separation the superiors toluene layer is extracted with 50mL toluene
DMSO and water layer, combining methylbenzene layer, add anhydrous sodium sulfate, afterwards dry filter and evaporated under reduced pressure filtrate, add 20mL
Ethanol stirs 15 minutes in the solid after being evaporated, is filtrated to get white crystalline solid Parylene F, sending for preparing is auspicious
Nuclear magnetic datas of the woods F through magnetic resonance detection be1H NMR (400 MHz, DMSO) δ 3.25。
Embodiment 2
The present embodiment and the difference of embodiment 1 are：Step（1）In：By 19g 4- methyl tetrafluorobenzyl alcohol and 150mL
Dry dichloromethane is placed in two-mouth bottle and reaction is cooled down at a temperature of less than 0 DEG C, and it is equal that 2~5 drop DMF catalysis stirrings are added dropwise
Even, the thionyl chloride that 12.2~12.8g is added dropwise with 25g/h rate of addition afterwards is stirred, and anti-with original solution in two-mouth bottle
Should, and detect that raw material reaction is finished by TLC plates；Step（2）In：By step（1）In mixed solution persistently stir after 1 hour
It is concentrated under reduced pressure by rotating instrument, adds petroleum ether and stirring after 10~30min of cooling, be filtrated to get white powdery solids 4- methyl
Tetrafluoro benzyl chloride, the average weight of the 4- methyl tetrafluoro benzyl chlorides is 19.1g, and now preparation efficiency is 92%, the 4- methyl prepared
Nuclear magnetic data of the tetrafluoro benzyl chloride through magnetic resonance detection be1H NMR (400 MHz, CDCl3) δ 2.25(s,3H), 4.63
(s, 2H)。
Embodiment 3
The present embodiment and the difference of embodiment 1 are：Step（1）In：By 19g 4- methyl tetrafluorobenzyl alcohol and 150mL
Dry dichloromethane is placed in two-mouth bottle and reaction is cooled down at a temperature of less than 0 DEG C, and it is equal that 2~5 drop DMF catalysis stirrings are added dropwise
Even, the thionyl chloride that 12.8~13.5g is added dropwise with 25g/h rate of addition afterwards is stirred, and anti-with original solution in two-mouth bottle
Should, and detect that raw material reaction is finished by TLC plates；Step（2）In：By step（1）In mixed solution persistently stir after 1 hour
It is concentrated under reduced pressure by rotating instrument, adds petroleum ether and stirring after 10~30min of cooling, be filtrated to get white powdery solids 4- methyl
Tetrafluoro benzyl chloride, the average weight of the 4- methyl tetrafluoro benzyl chlorides is 19.12g, and now preparation efficiency is 92%, the 4- first prepared
Nuclear magnetic data of the base tetrafluoro benzyl chloride through magnetic resonance detection be1H NMR (400 MHz, CDCl3) δ 2.25(s,3H), 4.63
(s, 2H)；
According to above-mentioned 3 embodiments, the preparation efficiency in embodiment 2 is higher than the preparation efficiency of embodiment 1, the system with embodiment 3
Standby efficiency almost maintains an equal level, thus from preparation efficiency is high and raw material using saving from the point of view of, embodiment 2 is most preferred embodiment,
Dropwise addition weight from thionyl chloride is 12.2~12.8g, and the median 12.5g in the range of this can be chosen during normal preparation and is carried out
Test operation, specific preparing raw material, prepares product and preparation efficiency such as following table：
。
Embodiment 4
The present embodiment and the difference of embodiment 2 are：Step（3）It is middle to put 4- methyl tetrafluoro benzyl chlorides and 100mL absolute ethyl alcohols
It is uniform using magnetic agitation in two-mouth bottle, 25ml methylamine water solutions are added dropwise with 25ml/h rate of addition at room temperature, and with two
Original solution reaction 24h in mouth bottle, and detect that raw material reaction is finished by TLC plates；
Every reaction is carried out at normal temperatures in the step, within certain reaction time, the preparation of 4- methyl tetrafluoro quaternary amines
Weight is 19.4g, and preparation efficiency is 79%, therefore is 60 DEG C still from reaction temperature to improve preparation efficiency.
Embodiment 5
The present embodiment and the difference of embodiment 2 are：Step（5）It is middle by 20g sodium hydroxides, 30ml DMSO, 150ml diformazans
Benzene is placed in there-necked flask, and stirring and being heated to 80 DEG C obtains dimethylbenzene system solution；
After product and the reaction of dimethylbenzene system solution, the solid Parylene F prepared weight is 5.80g, preparation efficiency
For 32.9%；Therefore the embodiment is drawn compared with embodiment 2, higher using toluene system solution preparation efficiency.
Embodiment 6
A kind of Parylene F preparation method, the preparation method is specific as follows：
（1）190g 4- methyl tetrafluorobenzyl alcohol and the 1500mL dichloromethane dried are placed in two-mouth bottle less than 0 DEG C
At a temperature of cool down reaction, and be added dropwise 20~50 and drip DMF catalysis and stir, be added dropwise 125g's afterwards with 25g/h rate of addition
Thionyl chloride is stirred, and is reacted with the original solution in two-mouth bottle, and detects that raw material reaction is finished by TLC plates, reactive chemistry formula
For：
（2）By step（1）In mixed solution persistently stir after 1 hour and to be concentrated under reduced pressure by rotating instrument, after 10~30min of cooling
Petroleum ether and stirring is added, the white powdery solids 4- methyl tetrafluoro benzyl chlorides for obtaining 195.5g, production is filtered and dried at 50 DEG C
Rate is 95%, and nuclear magnetic data of the 4- methyl tetrafluoro benzyl chlorides through magnetic resonance detection prepared is1H NMR (400 MHz,
CDCl3) δ 2.25(s,3H), 4.63(s, 2H)；
（3）By step（2）In the 195.5g 4- methyl tetrafluoro benzyl chlorides that prepare be placed in two-mouth bottle with 100mL absolute ethyl alcohols
In, it is uniform using magnetic agitation, 250ml methylamine water solutions are added dropwise with 25ml/h rate of addition at room temperature, 60 are then heated to
DEG C and with two-mouth bottle original solution react 24h, and by TLC plates detect raw material reaction finish, reactive chemistry formula is：
（4）By step（3）The solution decompression that middle reaction is completed is evaporated, and evaporated material includes the first that water, ethanol, unreacted are completed
Amine, adds 25ml dimethylbenzene afterwards, is stirred vigorously after 30min and filters, the filter cake after filtering is washed with acetone, and is placed on true
Drying obtains white powdery solids 4- methyl tetrafluoro quaternary amines in empty drying box, and solid is weighed as 240.0g, and yield is 96%,
Nuclear magnetic data of the 4- methyl tetrafluoro quaternary amines through magnetic resonance detection prepared be1H NMR (400 MHz, DMSO) δ
2.32(s,3H), 3.17(s,9H), 4.72(s, 2H)；
（5）200g sodium hydroxides, 300ml DMSO, 1500ml toluene are placed in there-necked flask, stirs and is heated to 80 DEG C
Obtain toluene system solution；
（6）With 150ml water dissolving step（4）In the 240.0g 4- methyl tetrafluoro quaternary amines that prepare, and in 3 hours
At the uniform velocity it is added dropwise in toluene system solution, uniform stirring 24h and reacts afterwards, and detect that raw material reaction is finished by TLC plates, instead
The chemical formula is answered to be：
（7）By step（6）In solution temperature be reduced to room temperature, then separation the superiors toluene layer is extracted with 50mL toluene
DMSO and water layer, combining methylbenzene layer, add anhydrous sodium sulfate, afterwards dry filter and evaporated under reduced pressure filtrate, add 20mL
Ethanol stirs 15 minutes in the solid after being evaporated, is filtrated to get white crystalline solid Parylene F, solid is weighed as
65.33g, yield is 37.24%, and nuclear magnetic datas of the Parylene F through magnetic resonance detection prepared is1H NMR (400
MHz, DMSO) δ 3.25。
The present embodiment and the difference of embodiment 2 be, step（1）Middle selection 190.0g 4- methyl tetrafluorobenzyl alcohols；
Step（3）4- methyl tetrafluoro benzyl chlorides of the middle selection 195.5g through preparing, the yield of 4- methyl tetrafluoro benzyl chlorides is 95%；Step
（6）4- methyl tetrafluoro quaternary amines of the middle selection 240.0g through preparing, the yield of 4- methyl tetrafluoro quaternary amines is 96%, step
（7）In prepare 65.33g solid Parylene F, solid Parylene F yield is 37.24%, process of the reaction in implementation
In, stable operation, and obtain compared with Example 2 lab scale and amplification yield it is basically identical, be easy to later industrialized production.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar can understand present disclosure and be carried out, and it is not intended to limit the scope of the present invention, all according to the present invention
The equivalent change or modification that Spirit Essence is made, should all cover within the scope of the present invention.
Claims (5)
1. a kind of Parylene F preparation method, it is characterised in that：The preparation method is specific as follows：
（1）19g 4- methyl tetrafluorobenzyl alcohol and the 150mL dichloromethane dried are placed in two-mouth bottle in the temperature less than 0 DEG C
The lower cooling of degree is reacted, and dropwise addition 2~5 is dripped DMF catalysis and stirred, and the thionyl chloride that 11.5~13.5g is added dropwise afterwards is stirred, and
Reacted with the original solution in two-mouth bottle, reactive chemistry formula is：
By step（1）In mixed solution persistently stir after 1 hour and to be concentrated under reduced pressure by rotating instrument, after 10~30min of cooling plus
Enter petroleum ether and stirring, be filtrated to get white powdery solids 4- methyl tetrafluoro benzyl chlorides；
By step（2）In the 4- methyl tetrafluoro benzyl chlorides that prepare be placed in 100mL absolute ethyl alcohols in two-mouth bottle, stirred using magnetic force
Mix uniform, 20~30ml methylamine water solutions are added dropwise at room temperature, be then heated to 60 DEG C and reacted with the original solution in two-mouth bottle
24h, reactive chemistry formula is：
By step（3）The solution decompression that middle reaction is completed is evaporated, and evaporated material includes the methylamine that water, ethanol, unreacted are completed, it
25ml dimethylbenzene is added afterwards, is stirred vigorously after 30min and filters, the filter cake after filtering is washed with acetone, and is placed on vacuum does
Drying obtains white powdery solids 4- methyl tetrafluoro quaternary amines in dry case；
20g sodium hydroxides, 30ml DMSO, 150ml toluene are placed in there-necked flask, stirring and being heated to 80 DEG C obtains first
Benzene system solution；
With 150ml water dissolving step（4）In the 4- methyl tetrafluoro quaternary amines that prepare, and be at the uniform velocity added dropwise in 3 hours
In toluene system solution, uniform stirring 24h and react afterwards, reactive chemistry formula is：
（7）By step（6）In solution temperature be reduced to room temperature, then separation the superiors toluene layer is extracted with 50mL toluene
DMSO and water layer, combining methylbenzene layer, add anhydrous sodium sulfate, afterwards dry filter and evaporated under reduced pressure filtrate, add 20mL
Ethanol stirs 15 minutes in the solid after being evaporated, is filtrated to get white crystalline solid Parylene F.
2. a kind of Parylene F according to claim 1 preparation method, it is characterised in that：The step（1）Middle dichloro is sub-
The rate of addition of sulfone is 25g/h.
3. a kind of Parylene F according to claim 1 preparation method, it is characterised in that：The step（3）Middle methylamine water
The rate of addition of solution is 25ml/h.
4. a kind of Parylene F according to claim 1 preparation method, it is characterised in that：The step（1）, step（3）
And step（6）Solution after middle hybrid reaction carries out the measure of solution impurity and content by TLC plates.
5. a kind of Parylene F according to claim 1 preparation method, it is characterised in that：The step（2）In be prepared into
To nuclear magnetic data of the 4- methyl tetrafluoro benzyl chlorides through magnetic resonance detection be1H NMR (400 MHz, CDCl3) δ 2.25(s,
3H), 4.63(s, 2H)；The step（4）In nuclear-magnetism of the 4- methyl tetrafluoro quaternary amines through magnetic resonance detection for preparing
Data are1H NMR (400 MHz, DMSO) δ 2.32(s,3H), 3.17(s,9H), 4.72(s, 2H)；The step
（7）In nuclear magnetic datas of the Parylene F through magnetic resonance detection for preparing be1H NMR (400 MHz, DMSO) δ
3.25。
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| 孙毓庆 主编: "《薄层扫描法及其在药物分析中的应用》", 31 January 1990, 人民卫生出版社 * |
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