CN101230011A - Method for preparing 2,2-di(3-amido-4-(2,4-dinitrophenoxy) phenyl] propane - Google Patents
Method for preparing 2,2-di(3-amido-4-(2,4-dinitrophenoxy) phenyl] propane Download PDFInfo
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- CN101230011A CN101230011A CNA2008100338493A CN200810033849A CN101230011A CN 101230011 A CN101230011 A CN 101230011A CN A2008100338493 A CNA2008100338493 A CN A2008100338493A CN 200810033849 A CN200810033849 A CN 200810033849A CN 101230011 A CN101230011 A CN 101230011A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention relates to a method for preparing 2, 2-double [3- amino-4-(2, 4- dinitrophenoxy) phenyl] propane, which comprises the steps that: (1) 2, 2-double(3- amino-4- hydroxyphenyl) propane and 2, 4-dinitrohalobenzenes with a molar ratio ranging from 1.0 : 2.0 to 1.0 : 2.2 are subject to a heat refluxing and water diversion reaction for 6 to 18 hours in a system comprising the nitrogen atmosphere, salt forming agents and organic solvents; (2) the reaction solution is concentrated, the reactant system is cooled and the water is added in the reactant system so as to precipitate the solid product; the obtained solutions are filtered and the obtained products are washed and dried so as obtain 2, 2-double [3- amino-4-(2, 4- dinitrophenoxy) phenyl] propane Crystal. The invention has simple operations and high product yield and purity, the solvents can be conveniently recycled and can be repeatedly used with few wastes, and the invention is environmentally friendly and suitable for industrialized production.
Description
Technical field
The invention belongs to the preparation field of aromatic organic compounds, particularly relate to a kind of 2, the preparation method of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-.
Background technology
Aromatic polyimide has excellent thermostability, chemical stability, anti-nuclear radiation, excellent mechanical property, electric property and organic solvent resistance, has obtained widespread use in space flight and aviation, electronics microelectronics, field such as electric.Because characteristics such as it these are high temperature resistant, high strength, anticorrosive, good insulating, film-forming process are simple, thereby be a kind of good functional materials, can satisfy the performance requriements of LCD (liquid-crystal display).
2, two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-are one of important source material of synthetic aroma adoption dant monomer, the i.e. important source material of the polynary primary amine of aromatic series.The polynary primary amine of aromatic series can be used to prepare the polyimide system of high cladodification, can make the polyimide novel material that temperature resistant grade is higher, over-all properties is better.
But 2, the preparation method of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-does not have disclosed patent or bibliographical information at present as yet.
Summary of the invention
The purpose of this invention is to provide a kind of 2, the preparation method of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, this method technology is simple, cost is low, environmental friendliness, purity and yield height, is applicable to industrial production.
Chemical equation of the present invention is as follows:
Wherein, X is a halogen atom, i.e. fluorine (F), chlorine (Cl), bromine (Br), iodine (I).
Of the present invention 2, the preparation method of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (the 3-amino-4-hydroxy phenyl) propane and 2 of 2-, 4-dinitrobenzene halogeno-benzene, nitrogen atmosphere, in salt forming agent, organic solvent system, reflux is divided water reaction 6～18 hours;
(2) concentration of reaction solution, the cooling reactant system adds water, separates out solid product, filter, washing, drying obtains 2, two [3-amino-4-(2,4-2,4-dinitrophenoxy base) phenyl] the propane crystal of 2-.
Described 2,4-dinitrobenzene halogeno-benzene is selected from 2,4-dinitrobenzene fluorobenzene, 2,4-dinitro-chloro-benzene, 2,4-dinitrobenzene bromobenzene, 2, one or more mixtures in the 4-dinitrobenzene phenyl-iodide.
Described salt forming agent is selected from one or more mixtures in Quilonum Retard, yellow soda ash, salt of wormwood, lithium bicarbonate, sodium bicarbonate, saleratus, Calcium hydrogen carbonate, Magnesium hydrogen carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, the calcium hydroxide.
Described salt forming agent and 2, the ratio of the mole number of two (the 3-amino-4-hydroxy phenyl) propane of 2-is 0.10～8.00: 1.00.
Described organic solvent is the mixture of water-insoluble organic solvent and strong polar non-proton organic solvent, and volume ratio is 1: 0.05～10.
Described water-insoluble organic solvent is selected from one or more mixtures in benzene,toluene,xylene, monochloro-benzene, dichlorobenzene, trichloro-benzene, ethylbenzene, diethylbenzene, a chlorotoluene, the dichloro-toluene.
Described strong polar non-proton organic solvent is selected from N, one or more mixtures in dinethylformamide, N,N-dimethylacetamide, N-N-methyl-2-2-pyrrolidone N-, the dimethyl sulfoxide (DMSO).
Described organic solvent and 2, the envelope-bulk to weight ratio of two (the 3-amino-4-hydroxy phenyl) propane of 2-is 5 milliliters～80 milliliters: 1 gram.
It is that temperature is 80 ℃～200 ℃ reaction that described reflux is divided the water reaction.
Beneficial effect of the present invention:
(1) the present invention is preparation 2, the commercial run of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, and product yield and purity are all higher;
(2) simple to operate, reaction process is carried out under normal pressure, does not relate to also not producing corrosives, equipment is not had particular requirement, less investment;
(3) organic solvent uses kind few, and reclaims conveniently, Recycling repeatedly, and the three wastes are few, and are environmentally friendly;
Two (the 3-amino-4-hydroxy phenyl) propane of (4) 2,2-reaction raw materials convenient sources such as (the stable supplies of Shanghai EMST Electron Material Co., Ltd), cost is lower, is convenient to further apply.
Description of drawings
Figure is 2, the molecular structure of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) 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 25.8 gram (0.10 moles) 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-, 44.6 gram (0.22 mole) 2, the 4-dinitro-chloro-benzene, 110.4 gram (0.80 mole) salt of wormwood, 70 milliliters of N, dinethylformamide and 280 milliliters of benzene are put into reactor, nitrogen atmosphere, stir, reflux divides the water reaction after 18 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separates out solid product, with hot wash 2～3 times, drying obtains 2, the two [3-amino-4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] propane, purity is 99.2%, obtains 2 according to reality, the two [3-amino-4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] amount and the theoretical amount of propane, calculate 2, the yield of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 95.3%.
Embodiment 2
With 25.8 gram (0.10 moles) 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-, 54.4 gram (0.22 mole) 2,4-dinitrobenzene bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 150 milliliters of N,N-dimethylacetamide, 200 milliliters of benzene and 15 milliliters of dimethylbenzene are put into reactor, nitrogen atmosphere, stir, reflux divides the water reaction after 6 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separates out solid product, with hot wash 2～3 times, drying obtains 2, the two [3-amino-4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] propane, purity is 99.5%, obtains 2 according to reality, the two [3-amino-4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] amount and the theoretical amount of propane, calculate 2, the yield of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 82.7%.
Embodiment 3
With 25.8 gram (0.10 moles) 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-, 40.5 gram (0.20 mole) 2, the 4-dinitro-chloro-benzene, 10.6 gram (0.10 mole) yellow soda ash, 60 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 100 milliliters of benzene and 23 milliliters of dichlorobenzenes are put into reactor, nitrogen atmosphere, stir, reflux divides the water reaction after 16 hours, concentration of reaction solution reclaims solvent to recycle the cooling reactant system, add water, separate out solid product, with hot wash 2～3 times, drying, obtain 2, two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, purity is 99.0%, according to 2 of reality acquisition, the amount and the theoretical yield of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-calculate 2, the yield of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 95.1%.
Embodiment 4
With 25.8 gram (0.10 moles) 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-, 40.9 gram (0.22 mole) 2,4-dinitrobenzene fluorobenzene, 11.8 gram (0.21 mole) potassium hydroxide, 20 milliliters of N, dinethylformamide and 100 milliliters of dichlorobenzenes are put into reactor, nitrogen atmosphere, stir, reflux divides the water reaction after 16 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separates out solid product, with hot wash 2～3 times, drying obtains 2, the two [3-amino-4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] propane, purity is 98.4%, obtains 2 according to reality, the two [3-amino-4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] amount and the theoretical amount of propane, calculate 2, the yield of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 77.1%.
Embodiment 5
With 25.8 gram (0.10 moles) 2, two (the 3-amino-4-hydroxy phenyl) propane of 2-, 51.9 gram (0.21 mole) 2,4-dinitrobenzene bromobenzene, 80.0 gram (0.80 mole) saleratus, 300 milliliters of dimethyl sulfoxide (DMSO) and 100 milliliters of dimethylbenzene are put into reactor, and nitrogen atmosphere stirs, reflux divides the water reaction after 18 hours, concentration of reaction solution reclaims solvent to recycle the cooling reactant system, add water, separate out solid product, with hot wash 2～3 times, drying, obtain 2, two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, purity is 99.0%, obtain 2 according to reality, the amount and the theoretical amount of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-calculate 2, the yield of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 94.8%.
Claims (9)
1.2 the preparation method of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (the 3-amino-4-hydroxy phenyl) propane and 2 of 2-, 4-dinitrobenzene halogeno-benzene, nitrogen atmosphere, in salt forming agent, organic solvent system, reflux is divided water reaction 6～18 hours;
(2) concentration of reaction solution, the cooling reactant system adds water, separates out solid product, filter, washing, drying gets 2, two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-.
2. according to claim 12, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described 2,4-dinitrobenzene halogeno-benzene is selected from 2,4-dinitrobenzene fluorobenzene, 2,4-dinitro-chloro-benzene, 2,4-dinitrobenzene bromobenzene, 2, one or more mixtures in the 4-dinitrobenzene phenyl-iodide.
3. according to claim 12, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described salt forming agent is selected from one or more mixtures in Quilonum Retard, yellow soda ash, salt of wormwood, lithium bicarbonate, sodium bicarbonate, saleratus, Calcium hydrogen carbonate, Magnesium hydrogen carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, the calcium hydroxide.
4. according to claim 1 or 3 described 2, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described salt forming agent and 2, the ratio of the mole number of two (the 3-amino-4-hydroxy phenyl) propane of 2-is 0.10～8.00: 1.00.
5. according to claim 12, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described organic solvent is the mixture of water-insoluble organic solvent and strong polar non-proton organic solvent, and volume ratio is 1: 0.05～10.
6. according to claim 52, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described water-insoluble organic solvent is selected from one or more mixtures in benzene,toluene,xylene, monochloro-benzene, dichlorobenzene, trichloro-benzene, ethylbenzene, diethylbenzene, a chlorotoluene, the dichloro-toluene.
7. according to claim 52, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described strong polar non-proton organic solvent is selected from N, one or more mixtures in dinethylformamide, N,N-dimethylacetamide, N-N-methyl-2-2-pyrrolidone N-, the dimethyl sulfoxide (DMSO).
8. according to claim 1 or 52, two [3-amino-the 4-(2 of 2-, 4-2,4-dinitrophenoxy base) phenyl] preparation method of propane, it is characterized in that: described organic solvent and 2, the envelope-bulk to weight ratio of two (the 3-amino-4-hydroxy phenyl) propane of 2-is 5 milliliters～80 milliliters: 1 gram.
9. according to claim 12, the preparation method of two [3-amino-4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is characterized in that: it is that temperature is 80 ℃～200 ℃ reaction that described reflux is divided the water reaction.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100338493A CN101230011A (en) | 2008-02-25 | 2008-02-25 | Method for preparing 2,2-di(3-amido-4-(2,4-dinitrophenoxy) phenyl] propane |
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| CNA2008100338493A CN101230011A (en) | 2008-02-25 | 2008-02-25 | Method for preparing 2,2-di(3-amido-4-(2,4-dinitrophenoxy) phenyl] propane |
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| CN101230011A true CN101230011A (en) | 2008-07-30 |
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| CNA2008100338493A Pending CN101230011A (en) | 2008-02-25 | 2008-02-25 | Method for preparing 2,2-di(3-amido-4-(2,4-dinitrophenoxy) phenyl] propane |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108191682A (en) * | 2018-01-26 | 2018-06-22 | 常州市阳光药业有限公司 | The synthetic method of bis- [4- (3- amino-benzene oxygens) phenyl] propane of 2,2- |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108191682A (en) * | 2018-01-26 | 2018-06-22 | 常州市阳光药业有限公司 | The synthetic method of bis- [4- (3- amino-benzene oxygens) phenyl] propane of 2,2- |
| CN108191682B (en) * | 2018-01-26 | 2020-09-22 | 常州市阳光药业有限公司 | Synthetic method of 2, 2-bis [4- (3-aminophenoxy) phenyl ] propane |
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