CN101397253A - Method for preparing 3,3-dinitro-4,4-bis(2,6-dinitro-4-trifluoromethyl phenoxy) biphenyl - Google Patents
Method for preparing 3,3-dinitro-4,4-bis(2,6-dinitro-4-trifluoromethyl phenoxy) biphenyl Download PDFInfo
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- CN101397253A CN101397253A CNA2008100413456A CN200810041345A CN101397253A CN 101397253 A CN101397253 A CN 101397253A CN A2008100413456 A CNA2008100413456 A CN A2008100413456A CN 200810041345 A CN200810041345 A CN 200810041345A CN 101397253 A CN101397253 A CN 101397253A
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Abstract
The invention relates to a preparation method of 3, 3'-dinitro-4, 4'-bis (2, 6-dinitro-4-trifluoromethyl-phenoxy) biphenyl, which comprises the following steps: (1) 3, 3'-dinitro-4, 4'-dihydroxy biphenyl and 2, 6-dinitro-4-trifluoromethyl halogenated benzene with the molar ratio of 1.0: 2.0 to 2.2 are carried out the heating, the reflux and the water separation reaction for 6 to 18 hours in a system with a salt forming agent and an organic solvent; and (2) reaction solution is concentrated, the reactant system is cooled, water is added, solid products are precipitated, filtered, washed and dried, so as to obtain the 3, 3'-dinitro-4, 4'-bis (2,6-dinitro-4-trifluoromethyl-phenoxy) biphenyl crystals. The preparation method has simple operation, high product yield, high purity, convenient solvent recycling, repeated use, less three wastes and environmentally friendly property, thereby being applicable to industrial production.
Description
Technical field
The invention belongs to the preparation field of aromatic organic compounds, particularly relate to a kind of 3,3 '-dinitrobenzene-4, the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl.
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).
3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl are one of synthetic monomeric important source material of high cladodification aromatic series fluorinated polyimide, the i.e. important source material of the fluorine-containing polynary primary amine of aromatic series.The fluorine-containing polynary primary amine of aromatic series can be used to prepare the fluorinated polyimide system of high cladodification, can make the fluorinated polyimide novel material that temperature resistant grade is higher, over-all properties is better.
But 3,3 '-dinitrobenzene-4, the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl 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 3,3 '-dinitrobenzene-4, the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl, 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 3,3 '-dinitrobenzene-4, the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl comprises the following steps:
(1) mol ratio is 3 of 1.0:2.0~2.2,3 '-dinitrobenzene-4, and 4 '-dihydroxybiphenyl and 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 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystal.
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 3,3 '-dinitrobenzene-4, the ratio of the mole number of 4 '-dihydroxybiphenyl is 0.80~8.00:1.00.
Described organic solvent is the mixture of water-insoluble organic solvent and strong polar non-proton organic solvent, mixed volume is than being 1:0.5~10, strong polar non-proton organic solvent and 3,3 '-dinitrobenzene-4, the envelope-bulk to weight ratio of 4 '-dihydroxybiphenyl are 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 ℃~180 ℃ reaction that described reflux is divided the water reaction.
Beneficial effect of the present invention:
(1) the present invention is preparation 3,3 '-dinitrobenzene-4, and the commercial run of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl, 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;
(4) 3,3 '-dinitrobenzene-4, reaction raw materials convenient sources such as 4 '-dihydroxybiphenyl, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 3,3 '-dinitrobenzene-4, the molecular structure of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl.
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 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 110.4 gram (0.80 mole) salt of wormwood, 2208 milliliters of N, dinethylformamide and 221 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 3 of 72.6 grams, 3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystalline product, purity is 99.7%, obtains 3 according to reality, 3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of biphenyl and theoretical amount (74.4 gram) calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 97.6%.
Embodiment 2
With 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 69.3 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 1500 milliliters of N,N-dimethylacetamide, 400 milliliters of benzene and 100 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 10 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 72.9 grams 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystalline product, purity is 99.5%, obtains 3 according to reality, 3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of biphenyl and theoretical amount (74.4 gram) calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 98.0%.
Embodiment 3
With 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 138 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 250 milliliters of benzene and 26 milliliters of dichlorobenzenes are put into reactor, stir, and reflux divides the water reaction after 11 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 66.7 grams 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystalline product, purity is 99.4%, according to 3 of reality acquisition, 3 '-dinitrobenzene-4, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl and theoretical yield (74.4 gram), calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 89.7%.
Embodiment 4
With 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 10.1 gram (0.18 mole) potassium hydroxide, 1200 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 300 milliliters of benzene and 40 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 6 hours, add 55.2 gram (0.40 mole) salt of wormwood, 55.9 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, reflux 10 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, drying, obtain 71.1 grams 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystalline product, purity is 99.6%, obtain 3 according to reality, 3 '-dinitrobenzene-4, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl and theoretical amount (74.4 gram), calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 95.5%.
Embodiment 5
With 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 66.2 gram (0.21 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 40.0 gram (0.40 mole) saleratus, 55.2 gram (0.40 mole) salt of wormwood, 700 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of dimethyl sulfoxide (DMSO), 500 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 300 milliliters of benzene and 100 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 16 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 69.0 grams 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl, purity is 99.3%, obtains 3 according to reality, 3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of biphenyl and theoretical amount (74.4 gram) calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 92.8%.
Embodiment 6
With 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 34.7 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 27.1 gram (0.10 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 55.2 gram (0.40 mole) salt of wormwood, 31.8 gram (0.30 mole) yellow soda ash, 900 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 600 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 300 milliliters of benzene and 50 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 15 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, drying, obtain 72.5 grams 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystalline product, purity is 99.5%, according to 3 of reality acquisition, 3 '-dinitrobenzene-4, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl and theoretical yield (74.4 gram), calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 97.5%.
Embodiment 7
With 27.6 gram (0.10 moles) 3,3 '-dinitrobenzene-4,4 '-dihydroxybiphenyl, 34.7 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 27.1 gram (0.10 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 55.2 gram (0.40 mole) salt of wormwood, 500 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 500 milliliters of N, dinethylformamide, 380 milliliters of toluene and 50 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 6 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, drying, obtain 48.4 grams 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl crystalline product, purity is 99.2%, according to 3 of reality acquisition, 3 '-dinitrobenzene-4, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl and theoretical yield (74.4 gram), calculate 3,3 '-dinitrobenzene-4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is 65.0%.
Claims (9)
1.3,3 '-dinitrobenzene-4, the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl comprises the following steps:
(1) mol ratio is 3 of 1.0:2.0~2.2,3 '-dinitrobenzene-4, and 4 '-dihydroxybiphenyl and 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 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl.
2. according to claim 13,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl 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 13,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl 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 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl, it is characterized in that: described salt forming agent and 3,3 '-dinitrobenzene-4, the ratio of the mole number of 4 '-dihydroxybiphenyl is 0.80~8.00:1.00.
5. according to claim 13,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl, it is characterized in that: described organic solvent is the mixture of water-insoluble organic solvent and strong polar non-proton organic solvent, and mixed volume is than being 1:0.5~10.
6. according to claim 53,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl 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 53,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl, 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 5 or 7 described 3,3 '-dinitrobenzene-4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of biphenyl, it is characterized in that: described strong polar non-proton organic solvent and 3,3 '-dinitrobenzene-4, the envelope-bulk to weight ratio of 4 '-dihydroxybiphenyl are 5 milliliters~80 milliliters: 1 gram.
9. according to claim 13,3 '-dinitrobenzene-4, the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) biphenyl is characterized in that: it is that temperature is 80 ℃~180 ℃ reaction that described reflux is divided the water reaction.
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CNA2008100413456A CN101397253A (en) | 2008-08-04 | 2008-08-04 | Method for preparing 3,3-dinitro-4,4-bis(2,6-dinitro-4-trifluoromethyl phenoxy) biphenyl |
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