CN101265207A - Method for preparing 2,2-di[4-(2,4-diaminophenoxy)-3,5-dimethylphenyl]hexafluoropropane - Google Patents
Method for preparing 2,2-di[4-(2,4-diaminophenoxy)-3,5-dimethylphenyl]hexafluoropropane Download PDFInfo
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- CN101265207A CN101265207A CNA2008100362897A CN200810036289A CN101265207A CN 101265207 A CN101265207 A CN 101265207A CN A2008100362897 A CNA2008100362897 A CN A2008100362897A CN 200810036289 A CN200810036289 A CN 200810036289A CN 101265207 A CN101265207 A CN 101265207A
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Abstract
The invention relates to a method of preparing 2, 2-bis(4-(2, 4-diamino phenoxy)-3, 5-dimethylphenyl) hexafluoropropane. The method comprises the following steps: 2, 2-bis(4-(2, 4-dinitro phenoxy)-3, 5-dimethylphenyl) hexafluoropropane reacts in palladium/carbon, hydrazine hydrate solution and the saturated fatty alcohol system for 1 to 5 hours under the temperature ranging from 70 DEG C to 85 DEG C; then the hot mixed solution is filtered, mother solution is cooled, and crystal products are precipitated; the crystal products are filtered and vacuum-dried to obtain 2, 2-bis(4-(2, 4-diamino phenoxy)-3, 5-dimethylphenyl) hexafluoropropane crystal. The method has simple operation, subsequent refined purification technology is not needed, the time consumption is less, the obtained products have high yield rate, the purity reaches more than 99 percent, and the method is suitable for industrialized production.
Description
Technical field
The invention belongs to the preparation field of the polynary primary amine of aromatic series, particularly relate to a kind of 2, the preparation method of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-.
Background technology
The heteroaromatic polymkeric substance has outstanding thermostability, anti-nuclear radiation, flame retardant resistance, organic solvent resistance and good high cryogenic mechanics performance and electric property, has obtained widespread use in space flight and aviation, electronics microelectronics, automobile boats and ships, electric contour performance field.
Along with the information electronic product towards high performance, lightweight, slimming, the development that becomes more meticulous, the insulating material of flexible copper-clad plate (FCCL) is had higher requirement, high strength heat-resisting, low-k and low-dielectric loss etc. as the needs height.Therefore, polyimide material enjoys favor in the FCCL field.
2, the two [4-(2, the 4-diamino phenoxy)-3 of 2-, the 5-3,5-dimethylphenyl] HFC-236fa is one of important source material of synthetic high cladodification polyimide resin, therefore, it not only can be applicable to the FCCL field, strengthens advanced composite material but also can be applicable to the fire resistant polyimide carbon fiber.In addition, 2, the important raw and processed materials that two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-also are synthetic More Malay imide resins.
Summary of the invention
The purpose of this invention is to provide a kind of 2, the two [4-(2, the 4-diamino phenoxy)-3 of 2-, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, this method technology is simple, need not follow-up refining purifying technique, the three wastes are few, and the purity of product and yield height are applicable to suitability for industrialized production.
Chemical equation of the present invention is as follows:
Of the present invention a kind of 2, the preparation method of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-comprises the steps:
2, the two [4-(2,4-2,4-dinitrophenoxy base)-3 of 2-, the 5-3,5-dimethylphenyl] HFC-236fa, in palladium/charcoal, hydrazine hydrate solution and saturated fatty alcohol system in 70 ℃～85 ℃ temperature range internal reactions after 1～5 hour, filtered while hot, the cooling mother liquor, separate out crystalline product, filter vacuum-drying, obtain 2, two [4-(2, the 4-diamino phenoxy)-3,5-3,5-dimethylphenyl] the HFC-236fa crystal of 2-.
Described palladium/charcoal, its palladium mass percent is 1%～15%.
The mass percent concentration of described hydrazine hydrate solution is 60%～85%.
Described saturated fatty alcohol is selected from methyl alcohol, ethanol, Virahol, n-propyl alcohol, propyl carbinol, isopropylcarbinol, ethylene glycol, 1,2-propylene glycol, 1, ammediol, one or more mixtures in 2-methyl cellosolve, cellosolvo, 2-methyl cellosolve, 3-methoxypropanol, 2-oxyethyl group propyl alcohol, the 3-oxyethyl group propyl alcohol.
Described 2, the weight ratio of two [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and palladium/charcoal is 100: 1～20.
Described 2, the mol ratio of two [4-(2,4-2,4-dinitrophenoxy base)-3,5-3,5-dimethylphenyl] HFC-236fa of 2-and hydrazine hydrate is 1: 20～50.
Described 2, the weightmeasurement ratio of two [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and saturated fatty alcohol is 1 to restrain: 15 milliliters～100 milliliters.
Beneficial effect of the present invention
(1) the present invention is preparation 2, the commercial run of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-;
(2) three wastes are few, and are environmentally friendly;
(3) consuming time few, obviously energy-saving and cost-reducing;
(4) simple to operate, related industrial chemicals is few;
(5) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa raw material sources such as (Shanghai EMST Electron Material Co., Ltd stably manufactured) are conveniently, help 2 of the present invention's preparation, the industrialization of two [4-(2, the 4-diamino phenoxy)-3,5-3,5-dimethylphenyl] the HFC-236fa products of 2-with further apply;
(6) product purity reaches more than 99%, yield is high.
Description of drawings
Figure is 2, the molecular structure of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 0.9 gram palladium mass percent be that palladium/charcoal of 15%, 900 milliliters of ethanol and 500ml ethylene glycol add in the reaction flask, stir, heat temperature raising to 60 ℃ begins to drip mass concentration and is 60% hydrazine hydrate solution, totally 250.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 4.5 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 55.8 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.7%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 92.4%.
Embodiment 2
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 14.0 gram palladium mass percents be that 1% palladium/charcoal and 5000ml ethanol add in the reaction flask, stir, heat temperature raising to 60 ℃ begins to drip mass concentration and is 85% hydrazine hydrate solution, totally 294.1 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 5 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 54.6 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.3%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 90.4%.
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 5.6 gram palladium mass percents be that 5% palladium/charcoal, 1500ml ethanol and 500ml 2-methyl cellosolve add in the reaction flask, stir, heat temperature raising to 60 ℃ begins to drip mass concentration and is 80% hydrazine hydrate solution, totally 260.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 4.5 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 55.6 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.5%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 92.1%.
Embodiment 4
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 4.3 gram palladium mass percents be palladium/charcoal of 10%, 1800 milliliters of ethanol and 1000ml 1, the 2-propylene glycol adds in the reaction flask, stirs heat temperature raising to 60 ℃, begin to drip mass concentration and be 80% hydrazine hydrate solution, totally 300.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 3.5 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 57.1 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.8%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 94.5%.
Embodiment 5
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 4.0 gram palladium mass percents be that 10% palladium/charcoal, 300ml methyl alcohol and 2800ml cellosolvo add in the reaction flask, stir, heat temperature raising to 60 ℃ begins to drip mass concentration and is 85% hydrazine hydrate solution, totally 280.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 5 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 56.5 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.8%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 93.6%.
Embodiment 6
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 2.8 gram palladium mass percents be palladium/charcoal of 15%, 3600 milliliters of ethanol and 600ml 1, ammediol adds in the reaction flask, stirs heat temperature raising to 60 ℃, begin to drip mass concentration and be 60% hydrazine hydrate solution, totally 260.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 2.5 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 58.1 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.8%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 96.2%.
Embodiment 7
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 7.2 gram palladium mass percents be that 5% palladium/charcoal, 1090ml 2-methyl cellosolve add in the reaction flask, stir, heat temperature raising to 60 ℃ begins to drip mass concentration and is 80% hydrazine hydrate solution, totally 260.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 4 hours, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 52.8 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.6%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 87.4%.
Embodiment 8
With 72.4 gram (0.1 moles) 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, 4.6 gram palladium mass percents be that palladium/charcoal of 10%, 7240 milliliters of ethanol add in the reaction flask, stir, heat temperature raising to 60 ℃ begins to drip mass concentration and is 80% hydrazine hydrate solution, totally 300.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 1 hour, cold slightly, filtered while hot, the cooling mother liquor adds pure water, separate out crystallized product, filter, vacuum-drying obtains 55.6 grams 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystal, purity is 99.8%, according to 2 of reality acquisition, amount of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (60.4 gram), calculate 2, the yield of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 92.1%.
Claims (7)
1. one kind 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, comprise the steps: 2,2-is two, and [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa, in palladium/charcoal, hydrazine hydrate solution and saturated fatty alcohol system in 70 ℃～85 ℃ temperature range internal reactions after 1～5 hour, filtered while hot, the cooling mother liquor, separate out crystalline product, filter vacuum-drying, obtain 2, two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-.
2. according to claim 12, the preparation method of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-, it is characterized in that: the palladium mass percent of described palladium/charcoal is 1%～15%.
3. according to claim 12, the preparation method of two [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-, it is characterized in that: the mass percent concentration of described hydrazine hydrate solution is 60%～85%.
4. according to claim 12,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, it is characterized in that: described saturated fatty alcohol is selected from methyl alcohol, ethanol, Virahol, n-propyl alcohol, propyl carbinol, isopropylcarbinol, ethylene glycol, 1,2-propylene glycol, 1, ammediol, one or more mixtures in 2-methyl cellosolve, cellosolvo, 2-methyl cellosolve, 3-methoxypropanol, 2-oxyethyl group propyl alcohol, the 3-oxyethyl group propyl alcohol.
5. according to claim 1 and 22,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, it is characterized in that: described 2, the weight ratio of two [4-(2,4-2,4-dinitrophenoxy base)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and palladium/charcoal is 100: 1～20.
6. according to claim 1 or 3 described 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, it is characterized in that: described 2, the mol ratio of two [4-(2,4-2,4-dinitrophenoxy base)-3,5-3,5-dimethylphenyl] HFC-236fa of 2-and hydrazine hydrate is 1: 20～50.
7. according to claim 1 or 4 described 2,2-is two, and [4-(2, the 4-diamino phenoxy)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, it is characterized in that: described 2, the weightmeasurement ratio of two [4-(2,4-2,4-dinitrophenoxy base)-3,5-3,5-dimethylphenyl] HFC-236fa of 2-and saturated fatty alcohol is 1 gram: 15 milliliters～100 milliliters.
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| CNA2008100362897A CN101265207A (en) | 2008-04-18 | 2008-04-18 | Method for preparing 2,2-di[4-(2,4-diaminophenoxy)-3,5-dimethylphenyl]hexafluoropropane |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106519680A (en) * | 2016-11-04 | 2017-03-22 | 东华大学 | PMDA type fluorine-containing branched polyimide resin film and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106519680A (en) * | 2016-11-04 | 2017-03-22 | 东华大学 | PMDA type fluorine-containing branched polyimide resin film and preparation method thereof |
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