CN101234974B - Method for preparing 2,2-di[4-(2,4-dinitrophenoxy)phenyl]propane - Google Patents
Method for preparing 2,2-di[4-(2,4-dinitrophenoxy)phenyl]propane Download PDFInfo
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- CN101234974B CN101234974B CN2008100338525A CN200810033852A CN101234974B CN 101234974 B CN101234974 B CN 101234974B CN 2008100338525 A CN2008100338525 A CN 2008100338525A CN 200810033852 A CN200810033852 A CN 200810033852A CN 101234974 B CN101234974 B CN 101234974B
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Abstract
The invention relates to a preparation method of 2, 2-bis-[4-(2, 4-dinitrophenoxy) phenyl] propane, comprising: (1) heating to reflux and segregate water for 6-18h to treat 2, 2-bis-(4-hydroxy phenyl) propane and 2, 4-dinitro halogenated benzene at a mol ratio of 1.0:2.0 to 2.2, in a system of a salt forming agent and an organic solvent; (2) concentrating reaction liquid, cooling the reactant system, adding water, precipitating solid product, filtering, washing and drying to obtain 2, 2-bis-[4-(2, 4-dinitrophenoxy) phenyl] propane. The preparation method of 2, 2-bis-[4-(2, 4-dinitrophenoxy) phenyl] propane has simple operation, high yield and purity, while the solvents can be recovered easily and repeatedly used, with low generation of three wastes and environment-friendly property. The invention is suitable for industrial 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 [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 [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 branching, can make the polyimide novel material that temperature resistant grade is higher, over-all properties is better.
Summary of the invention
The purpose of this invention is to provide a kind of 2, the preparation method of two [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 [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 (4-hydroxy phenyl) propane and 2 of 2-, 4-dinitrobenzene halogeno-benzene, 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 [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 (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, organic solvent and 2, and the envelope-bulk to weight ratio of two (4-hydroxy phenyl) propane of 2-is 5 milliliters～80 milliliters: 1 gram.
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).
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 [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;
Reaction raw materials convenient sources such as two (4-hydroxy phenyl) propane of (4) 2,2-, cost is lower, is convenient to further apply.
Description of drawings
Figure is 2, the molecular structure of two [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 22.8 gram (0.10 moles) 2, two (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, 700 milliliters of N, dinethylformamide and 180 milliliters of toluene are put into reactor, stir, 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, washing, drying, obtain 54.4 grams 2, two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, purity is 99.2%, obtain 2 according to reality, amount of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-and theoretical amount (56.0 gram) calculate 2, the yield of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 97.2%.
Embodiment 2
With 22.8 gram (0.10 moles) 2, two (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 and 15 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 6 hours, concentration of reaction solution reclaims solvent to recycle the cooling reactant system, add water, separate out solid product, washing, drying, obtain 38.4 grams 2, two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, purity is 99.3%, obtain 2 according to reality, amount of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-and theoretical amount (56.0 gram) calculate 2, the yield of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 68.5%.
Embodiment 3
With 22.8 gram (0.10 moles) 2, two (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, 120 milliliters of N-methyl-2-put into reactor than pyrrolidone and 45 milliliters of dichlorobenzenes, 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, washing, drying obtains 52.1 grams 2, and 2-is two, and [4-(2,4-2,4-dinitrophenoxy base) phenyl] propane, purity is 99.4%, and according to 2 of reality acquisition, 2-is two, and [4-(2,4-2,4-dinitrophenoxy base) phenyl] amount of propane and theoretical yield (56.0 gram), calculate 2, the yield of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 93.1%.
Embodiment 4
With 22.8 gram (0.10 moles) 2, two (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 400 milliliters of dichlorobenzenes are put into reactor, 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, washing, drying, obtain 39.3 grams 2, two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-, purity is 92.1%, obtain 2 according to reality, amount of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-and theoretical amount (56.0 gram) calculate 2, the yield of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 70.1%.
Embodiment 5
With 22.8 gram (0.10 moles) 2, two (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, 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, washing, drying obtains 51.4 grams 2, and 2-is two, and [4-(2,4-2,4-dinitrophenoxy base) phenyl] propane, purity is 99.2%, obtains 2 according to reality, and 2-is two, and [4-(2,4-2,4-dinitrophenoxy base) phenyl] amount of propane and theoretical amount (56.0 gram), calculate 2, the yield of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is 91.7%.
Claims (5)
1.2 the preparation method of two [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 (4-hydroxy phenyl) propane and 2 of 2-, 4-dinitrobenzene halogeno-benzene in salt forming agent, organic solvent system, divides water reaction 6～18 hours in 80 ℃～200 ℃ reflux;
Wherein, 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; 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);
(2) concentration of reaction solution, the cooling reactant system adds water, separates out solid product, filter, washing, drying obtains 2, two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-.
2. according to claim 12,2-is two, and [4-(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 12,2-is two, and [4-(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, the preparation method of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is characterized in that: described salt forming agent and 2, the ratio of the mole number of 2-pair of (4-hydroxy phenyl) propane is 0.10～8.00: 1.00.
5. according to claim 12, the preparation method of two [4-(2, the 4-2,4-dinitrophenoxy base) phenyl] propane of 2-is characterized in that: described organic solvent and 2, the envelope-bulk to weight ratio of two (4-hydroxy phenyl) propane of 2-is 5 milliliters～80 milliliters: 1 restrains.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1361097A (en) * | 2000-12-27 | 2002-07-31 | 中国科学院化学研究所 | Fluorinated organic diamine and its derivatives and their prepn process and use |
| CN1472193A (en) * | 2003-07-11 | 2004-02-04 | 南通探索科技有限公司 | Preparation of 2,2-bi-[4-(4-aminophenoxy)phenyl]propane |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1361097A (en) * | 2000-12-27 | 2002-07-31 | 中国科学院化学研究所 | Fluorinated organic diamine and its derivatives and their prepn process and use |
| CN1472193A (en) * | 2003-07-11 | 2004-02-04 | 南通探索科技有限公司 | Preparation of 2,2-bi-[4-(4-aminophenoxy)phenyl]propane |
Non-Patent Citations (4)
| Title |
|---|
| CA文献号81:121073.1974, * |
| CA文献号82:124950.1975, * |
| E. Halasa等.Synteza dwuamin aromatycznych z mostkami eterowymi.PRZEMYSL CHEMICZNY64卷 2期.1985,64卷(2期),79-82页. |
| E. Halasa等.Synteza dwuamin aromatycznych z mostkami eterowymi.PRZEMYSL CHEMICZNY64卷 2期.1985,64卷(2期),79-82页. * |
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