CN101265191A - Method for preparing 2,2-di[4-(2,6-dinitro-4-trifluoromethylphenoxy)-3,5-dimethylphenyl]propane - Google Patents
Method for preparing 2,2-di[4-(2,6-dinitro-4-trifluoromethylphenoxy)-3,5-dimethylphenyl]propane Download PDFInfo
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- CN101265191A CN101265191A CNA2008100362914A CN200810036291A CN101265191A CN 101265191 A CN101265191 A CN 101265191A CN A2008100362914 A CNA2008100362914 A CN A2008100362914A CN 200810036291 A CN200810036291 A CN 200810036291A CN 101265191 A CN101265191 A CN 101265191A
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- dinitrobenzene
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Abstract
The invention relates to a method of preparing 2, 2-bis (4-(2, 6-dinitro-4-trifluoromethyl phenoxy)-3, 5-dimethylphenyl) propane. The method comprises the following steps: (1) the molar ratio of 2, 2-bis (4-oxhydryl-3, 5-dimethylphenyl) propane and 2, 6-dinitro-4-trifluoromethylphenyl halides is 1.0:2.0 to 2.2, and the reflux and removing water reaction is performed in the salt forming agent and organic solvent system for 6 to 18 hours through heating; (2) reaction solution is concentrated, the reactant system is cooled, water is added in, and solid products are precipitated, filtered, washed, and dried, so that 2, 2-bis (4-(2, 6-dinitro-4-trifluoromethyl phenoxy)-3, 5-dimethylphenyl) propane crystal is obtained. The operation of the preparation method is simple, the product yield rate and the purity are high, the solvent is convenient to be recovered and can be used repeatedly, three wastes are fewer, and the method is environment-friendly and is suitable for the 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 [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-are one of synthetic monomeric important source material of high cladodification aromatic polyimide, 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 [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 (C1), bromine (Br), iodine (I).
Of the present invention 2, the preparation method of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) propane and 2 of 2-, 6-dinitrobenzene-4-trifluoromethyl 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 gets 2, two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,5-3,5-dimethylphenyl] the propane crystal of 2-.
Described 2,6-dinitrobenzene-4-trifluoromethyl halogeno-benzene is selected from 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 2, one or more mixtures in 6-dinitrobenzene-4-trifluoromethyl 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-hydroxyl-3, the 5-3,5-dimethylphenyl) 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, volume ratio is 1: 0.05～10, organic solvent and 2, the envelope-bulk to weight ratio of two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) 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-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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-hydroxyl-3, the 5-3,5-dimethylphenyl) propane of (4) 2,2-, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 2, the molecular structure of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 28.4 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) propane, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 110.4 gram (0.80 mole) salt of wormwood, 1200 milliliters of N, dinethylformamide and 180 milliliters of toluene are put into reactor, stir, reflux divides the water reaction after 18 hours, and concentration of reaction solution reclaims solvent to recycle, the cooling reactant system, add water, separate out solid product, with hot wash 2～3 times, dry, obtain 2 of 73.1 grams, the two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3 of 2-, the 5-3,5-dimethylphenyl] the propane crystalline product, purity is 99.6%, obtains 2 according to reality, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] amount of propane and theoretical amount (75.2 gram), calculate 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,5-3,5-dimethylphenyl] yield of propane is 97.2%.
Embodiment 2
With 28.4 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) propane, 69.3 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 800 milliliters of N,N-dimethylacetamide, 100 milliliters of benzene and 50 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 16 hours, and concentration of reaction solution reclaims solvent to recycle, the cooling reactant system, add water, separate out solid product, with hot wash 2～3 times, dry, obtain 68.8 grams 2, the two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3 of 2-, the 5-3,5-dimethylphenyl] the propane crystalline product, purity is 99.5%, obtains 2 according to reality, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] amount of propane and theoretical amount (75.2 gram), calculate 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,5-3,5-dimethylphenyl] yield of propane is 91.5%.
Embodiment 3
With 28.4 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) propane, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 380 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 800 milliliters of benzene and 100 milliliters of dichlorobenzenes are put into reactor, stir, and reflux divides the water reaction after 12 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separate out solid product, with hot wash 2～3 times, drying, obtain 65.0 grams 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] the propane crystalline product, purity is 99.5%, according to 2 of reality acquisition, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-and theoretical yield (75.2 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-is 86.4%.
Embodiment 4
With 28.4 gram (0.10 moles) 2, two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) propane of 2-, 11.8 gram (0.21 mole) potassium hydroxide, 600 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of benzene and 40 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 6 hours, add 55.9 gram (0.22 moles) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, reflux 12 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separate out solid product, with hot wash 2～3 times, drying, obtain 65.7 grams 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] the propane crystalline product, purity is 99.5%, obtain 2 according to reality, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-and theoretical amount (75.2 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-is 87.4%.
Embodiment 5
With 28.4 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) propane, 66.2 gram (0.21 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 80.0 gram (0.80 mole) saleratus, 600 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of dimethyl sulfoxide (DMSO), 100 milliliters of benzene and 50 milliliters of dimethylbenzene are put into reactor, stir, and reflux divides the water reaction after 18 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separate out solid product, with hot wash 2～3 times, drying, obtain 73.2 grams 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane, purity is 99.6%, obtain 2 according to reality, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-and theoretical amount (75.2 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-is 97.3%.
Embodiment 6
With 28.4 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) propane, 28.0 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, 27.1 gram (0.10 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 40.0 gram (0.40 mole) saleratus, 10.6 gram (0.10 mole) yellow soda ash, 142 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 1500 milliliters of benzene and 500 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 12 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system, add water, separate out solid product, with hot wash 2～3 times, dry, obtain 44.1 grams 2, the two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3 of 2-, the 5-3,5-dimethylphenyl] the propane crystalline product, purity is 99.0%, and according to 2 of reality acquisition, 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] amount of propane and theoretical yield (75.2 gram), calculate 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,5-3,5-dimethylphenyl] yield of propane is 58.7%.
Claims (9)
1.2 the preparation method of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) propane and 2 of 2-, 6-dinitrobenzene-4-trifluoromethyl 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 gets 2, two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] propane of 2-.
2. according to claim 12,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] preparation method of propane, it is characterized in that: described 2,6-dinitrobenzene-4-trifluoromethyl halogeno-benzene is selected from 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 2, one or more mixtures in 6-dinitrobenzene-4-trifluoromethyl phenyl-iodide.
3. according to claim 12,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] preparation method of propane, it is characterized in that: described salt forming agent and 2, the ratio of the mole number of two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) propane of 2-is 0.10～8.00: 1.00.
5. according to claim 12,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 1 or 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 1 or 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] preparation method of propane, it is characterized in that: described organic solvent and 2, the envelope-bulk to weight ratio of two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) propane of 2-is 5 milliliters～80 milliliters: 1 gram.
9. according to claim 12, the preparation method of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] 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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| CNA2008100362914A CN101265191A (en) | 2008-04-18 | 2008-04-18 | Method for preparing 2,2-di[4-(2,6-dinitro-4-trifluoromethylphenoxy)-3,5-dimethylphenyl]propane |
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| CNA2008100362914A CN101265191A (en) | 2008-04-18 | 2008-04-18 | Method for preparing 2,2-di[4-(2,6-dinitro-4-trifluoromethylphenoxy)-3,5-dimethylphenyl]propane |
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