CN101245027A - Process for producing 2,2-bis[3-amido-4-(4-aminophenoxy)phenyl]propane - Google Patents
Process for producing 2,2-bis[3-amido-4-(4-aminophenoxy)phenyl]propane Download PDFInfo
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- CN101245027A CN101245027A CNA2008100349746A CN200810034974A CN101245027A CN 101245027 A CN101245027 A CN 101245027A CN A2008100349746 A CNA2008100349746 A CN A2008100349746A CN 200810034974 A CN200810034974 A CN 200810034974A CN 101245027 A CN101245027 A CN 101245027A
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Abstract
The invention relates to a preparation method of 2,2-double(3-amino-4-(4-amino phenoxy)phenyl)propane, comprising the steps as following, after being put into a solvent system of the solution of palladium or carbon hydrazine hydrate and saturated fatty alcohol for reaction for 1 to 5 hours with the temperature of 70 to 85 DEG C, the 2,2-double(3-amino-4-(4-nitro phenoxy)phenyl)propane is filtered when being hot, mother liquor is cooled off, pure water is dripped in, crystal products are precipitated, filtered, and dried in vacuum, and crystals of the 2,2-double(3-amino-4-(4-amino phenoxy)phenyl)propane are gained. The method has simple operation, needs no subsequent refining and purifying technique, takes little time, has the products with the high yield and the purity of more than 99 percent, and is suitable for industrial 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 [3-amino-4-(4-amino-benzene oxygen) phenyl] propane 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, one of important source material that two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-are synthetic high cladodification polyimide resins, 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 [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-also are synthetic More Malay imide resins.
2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-are the polynary primary amine of a kind of important aromatic series, but its preparation method do not see patent is arranged, bibliographical information.
Summary of the invention
The purpose of this invention is to provide a kind of 2, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-, this method technology is simple, need not follow-up refining purifying technique, the three wastes are few, 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 [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-comprises the steps:
2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, in palladium/charcoal, hydrazine hydrate solution and saturated fatty alcohol solvent system in 70 ℃～85 ℃ temperature range internal reactions after 1～5 hour, filtered while hot, cooling mother liquor, drip an amount of pure water, separate out crystalline product, filter vacuum-drying, obtain 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane 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 alcoholic solvent 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 [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and palladium/charcoal is 100: 1～20.
Described 2, the mol ratio of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and hydrazine hydrate is 1: 8～25.
Described 2, the weightmeasurement ratio of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and saturated fatty alcoholic solvent 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 [3-amino-4-(4-amino-benzene oxygen) phenyl] propane 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) raw material sources are convenient;
(6) product purity reaches more than 99%, yield is high.
Description of drawings
Figure is 2, the molecular structure of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane 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 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 0.5 gram palladium mass percent are that palladium/charcoal of 15%, 350 milliliters of ethanol and 400ml ethylene glycol add in the reaction flask, stir, heat temperature raising to 60 ℃, begin to drip mass concentration and be 60% hydrazine hydrate solution (the hydrazine hydrate molecular weight is 50.06), totally 208.3 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, drip an amount of pure water, separate out crystallized product, filter, vacuum-drying, obtain 41.8 grams 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane crystal of 2-, purity is 99.6%, according to 2 of reality acquisition, amount of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-and theoretical amount (44.0 gram) calculate 2, and the yield of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-is 95.1%.
Embodiment 2
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 10.0 gram palladium mass percents are that 1% palladium/charcoal and 6000ml ethanol add in the reaction flask, stir, heat temperature raising to 60 ℃, begin to drip mass concentration and be 85% hydrazine hydrate solution, totally 47.1 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, drip an amount of pure water, separate out crystallized product, filter, vacuum-drying, obtain 24.8 grams 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane crystal of 2-, purity is 98.1%, according to 2 of reality acquisition, amount of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-and theoretical amount (44.0 gram) calculate 2, and the yield of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-is 56.4%.
Embodiment 3
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 4.0 gram palladium mass percents are that 5% palladium/charcoal and 1000ml 2-methyl cellosolve add in the reaction flask, stir, heat temperature raising to 60 ℃, begin to drip mass concentration and be 80% hydrazine hydrate solution, totally 130.0 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, drip an amount of pure water, separate out crystallized product, filter, vacuum-drying, obtain 39.7 grams 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane crystal of 2-, purity is 99.1%, according to 2 of reality acquisition, amount of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-and theoretical amount (44.0 gram) calculate 2, and the yield of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-is 90.2%.
Embodiment 4
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 3.0 gram palladium mass percents are palladium/charcoal of 10%, 100 milliliters of ethanol and 800ml 1, the 2-propylene glycol adds in the reaction flask, stir, heat temperature raising to 60 ℃, begin to drip mass concentration and be 80% hydrazine hydrate solution, totally 50.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 3 hours, cold slightly, filtered while hot, the cooling mother liquor, drip an amount of pure water, separate out crystallized product, filter, vacuum-drying, obtain 41.1 grams 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane crystal of 2-, purity is 99.5%, according to 2 of reality acquisition, amount of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-and theoretical amount (44.0 gram) calculate 2, and the yield of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-is 93.5%.
Embodiment 5
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 3.5 gram palladium mass percents are that 10% palladium/charcoal, 20ml methyl alcohol and 1000ml cellosolvo add in the reaction flask, stir, heat temperature raising to 60 ℃, begin to drip mass concentration and be 85% hydrazine hydrate solution, totally 140.0 grams (solution weight).After hydrazine hydrate is added dropwise to complete, in 70 ℃～85 ℃ temperature range, continued stirring reaction 2 hours, cold slightly, filtered while hot, the cooling mother liquor, drip an amount of pure water, separate out crystallized product, filter, vacuum-drying, obtain 41.5 grams 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane crystal of 2-, purity is 99.2%, according to 2 of reality acquisition, amount of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-and theoretical amount (44.0 gram) calculate 2, and the yield of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-is 94.3%.
Embodiment 6
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 1.6 gram palladium mass percents are palladium/charcoal of 15%, 100 milliliters of ethanol and 800ml 1, ammediol adds in the reaction flask, stir, heat temperature raising to 60 ℃, begin to drip mass concentration and be 60% hydrazine hydrate solution, totally 130.0 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, drip an amount of pure water, separate out crystallized product, filter, vacuum-drying, obtain 41.2 grams 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] the propane crystal of 2-, purity is 99.6%, according to 2 of reality acquisition, amount of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-and theoretical amount (44.0 gram) calculate 2, and the yield of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-is 93.7%.
Claims (7)
1. one kind 2, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-comprises the steps: 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, in palladium/charcoal, hydrazine hydrate solution and saturated fatty alcohol solvent system in 70 ℃～85 ℃ temperature range internal reactions after 1～5 hour, filtered while hot, cooling mother liquor, drip an amount of pure water, separate out crystalline product, filter vacuum-drying, obtain 2, two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-.
2. according to claim 12, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane 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 [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-, it is characterized in that: the mass percent concentration of described hydrazine hydrate solution is 60%～85%.
4. according to claim 12, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-, it is characterized in that: described saturated fatty alcoholic solvent 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, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-, it is characterized in that: described 2, the weight ratio of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and palladium/charcoal is 100: 1～20.
6. according to claim 1 or 3 described 2, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-, it is characterized in that: described 2, the mol ratio of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and hydrazine hydrate is 1: 8～25.
7. according to claim 1 or 4 described 2, the preparation method of two [3-amino-4-(4-amino-benzene oxygen) phenyl] propane of 2-, it is characterized in that: described 2, the weightmeasurement ratio of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and saturated fatty alcoholic solvent is 1 to restrain: 15 milliliters～100 milliliters.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100349746A CN101245027A (en) | 2008-03-21 | 2008-03-21 | Process for producing 2,2-bis[3-amido-4-(4-aminophenoxy)phenyl]propane |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100349746A CN101245027A (en) | 2008-03-21 | 2008-03-21 | Process for producing 2,2-bis[3-amido-4-(4-aminophenoxy)phenyl]propane |
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| CN101245027A true CN101245027A (en) | 2008-08-20 |
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| CNA2008100349746A Pending CN101245027A (en) | 2008-03-21 | 2008-03-21 | Process for producing 2,2-bis[3-amido-4-(4-aminophenoxy)phenyl]propane |
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Open date: 20080820 |