CN101367734A - Preparation method of 2,2 bi-[3-nitryl-4-(2,6-dinitryl-4-trifluoromethyl phenoxy)phenyl] propane - Google Patents

Preparation method of 2,2 bi-[3-nitryl-4-(2,6-dinitryl-4-trifluoromethyl phenoxy)phenyl] propane Download PDF

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CN101367734A
CN101367734A CNA2008100413441A CN200810041344A CN101367734A CN 101367734 A CN101367734 A CN 101367734A CN A2008100413441 A CNA2008100413441 A CN A2008100413441A CN 200810041344 A CN200810041344 A CN 200810041344A CN 101367734 A CN101367734 A CN 101367734A
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dinitrobenzene
propane
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phenyl
trifluoromethylphenopendant
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虞鑫海
徐永芬
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Donghua University
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Abstract

The present invention relates to a preparation method of 2, 2-bis [3-nitro-4-(2, 6-dinitro-4-trifluoromethyl phenoxy) benzyl] propane. The preparation method comprises the following steps: firstly, 2, 2-bis (3-nitro-4-hydroxyphenyl) propane and 2, 6-dinitro-4-trifluoromethylphenyl halide with a molar ratio of from 1.0 to 2.0 to 2.2 are added into a system of salifying agent and organic solvent, and the system is heated and perform refluxing and water segregation reaction of 6 to 18 hours; secondly, the reaction solution is condensed, the reactant system is cooled, water is added, and solid products are separated, filtered, washed and dried to prepare the 2, 2-bis [3-nitro-4-(2, 6-dinitro-4-trifluoromethyl phenoxy) benzyl] propane. The present invention has the advantages that the operation is simple, the yield rate and purity of the product are high, the solvent recovery is convenient and the solvent can be repeatedly used, the three wastes are less, the preparation method is environment friendly, and the present invention is suitable for industrial production.

Description

2, the preparation method of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-
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-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-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 2, the preparation method of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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:
Figure A200810041344D00041
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-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-comprises the following steps:
(1) mol ratio is 2 of 1.0:2.0～2.2, two (3-nitro-4-hydroxy phenyl) 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 [3-nitro-4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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 (3-nitro-4-hydroxy phenyl) propane of 2-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 2, the envelope-bulk to weight ratio of two (3-nitro-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 ℃～180 ℃ 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-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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 (3-nitro-4-hydroxy phenyl) 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 [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 110.4 gram (0.80 mole) salt of wormwood, 2544 milliliters of N, dinethylformamide and 260 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, with hot wash 2～3 times, drying, obtain 2 of 72.3 grams, two [3-nitro-4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the propane crystalline products of 2-, purity is 99.5%, obtain 2 according to reality, amount of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-and theoretical amount (78.6 gram) calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 92.0%.
Embodiment 2
With 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 69.3 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 1800 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 250 milliliters of benzene and 150 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 12 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 71.3 grams 2, two [3-nitro-4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the propane crystalline products of 2-, purity is 99.4%, obtain 2 according to reality, amount of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-and theoretical amount (78.6 gram) calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 90.7%.
Embodiment 3
With 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 160 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 280 milliliters of benzene and 40 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 14 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 64.0 grams 2, the two [3-nitro-4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the propane crystalline product, purity is 99.0%, according to 2 of reality acquisition, and the two [3-nitro-4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of propane and theoretical yield (78.6 gram), calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 81.4%.
Embodiment 4
With 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 11.8 gram (0.21 mole) potassium hydroxide, 900 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 350 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, separates out solid product, with hot wash 2～3 times, drying obtains 68.9 grams 2, the two [3-nitro-4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the propane crystalline product, purity is 99.4%, obtains 2 according to reality, the two [3-nitro-4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of propane and theoretical amount (78.6 gram), calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 87.7%.
Embodiment 5
With 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 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, 800 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of dimethyl sulfoxide (DMSO), 300 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 450 milliliters of benzene and 250 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, add water, separate out solid product, with hot wash 2～3 times, dry, obtain 76.6 grams 2, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane, purity is 99.2%, obtain 2 according to reality, amount of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-and theoretical amount (78.6 gram) calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 97.5%.
Embodiment 6
With 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 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, 800 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 400 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 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 71.1 grams 2, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the propane crystalline product, purity is 99.6%, according to 2 of reality acquisition, and the two [3-nitro-4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of propane and theoretical yield (78.6 gram), calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 90.5%.
Embodiment 7
With 31.8 gram (0.10 moles) 2, two (3-nitro-4-hydroxy phenyl) propane of 2-, 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, 1000 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of N, dinethylformamide, 300 milliliters of toluene and 50 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 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, dry, obtain 74.4 grams 2, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the propane crystalline product, purity is 99.5%, according to 2 of reality acquisition, and the two [3-nitro-4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of propane and theoretical yield (78.6 gram), calculate 2, the yield of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is 94.7%.

Claims (9)

1.2 the preparation method of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-comprises the following steps:
(1) mol ratio is 2 of 1.0:2.0～2.2, two (3-nitro-4-hydroxy phenyl) propane and 2 of 2-, and 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 [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-.
2. according to claim 12, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] preparation method of propane, it is characterized in that: described salt forming agent and 2, the ratio of the mole number of two (3-nitro-4-hydroxy phenyl) propane of 2-is 0.80～8.00:1.00.
5. according to claim 12, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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 mixed volume is than being 1:0.5～10.
6. according to claim 52, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) 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 5 or 7 described 2, two [3-nitro-the 4-(2 of 2-, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] preparation method of propane, it is characterized in that: described strong polar non-proton organic solvent and 2, the envelope-bulk to weight ratio of two (3-nitro-4-hydroxy phenyl) propane of 2-is 5 milliliters～80 milliliters: 1 gram.
9. according to claim 12, the preparation method of two [3-nitro-4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] propane of 2-is characterized in that: it is that temperature is 80 ℃～180 ℃ reaction that described reflux is divided the water reaction.
CNA2008100413441A 2008-08-04 2008-08-04 Preparation method of 2,2 bi-[3-nitryl-4-(2,6-dinitryl-4-trifluoromethyl phenoxy)phenyl] propane Pending CN101367734A (en)

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