CN101293837A - Method for preparing 2,2di[4-(2,6-dinitryl-4-trifluoromethyl phenoxy) -3,5- dimethyl phenyl]hexa-fluorine propane - Google Patents

Method for preparing 2,2di[4-(2,6-dinitryl-4-trifluoromethyl phenoxy) -3,5- dimethyl phenyl]hexa-fluorine propane Download PDF

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CN101293837A
CN101293837A CNA2008100391245A CN200810039124A CN101293837A CN 101293837 A CN101293837 A CN 101293837A CN A2008100391245 A CNA2008100391245 A CN A2008100391245A CN 200810039124 A CN200810039124 A CN 200810039124A CN 101293837 A CN101293837 A CN 101293837A
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dinitrobenzene
dimethylphenyl
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trifluoromethylphenopendant
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虞鑫海
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Donghua University
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Abstract

The invention relates to a method for preparing 2,2-bis[4-(2, 6-binitro-4-trifluoromethylphenoxy)-3,5-dimethylphenyl]hexafluoropropane, which comprises (1) allowing 2,2-bis(4-hydroxy-3,5-dimethylphenyl)hexafluoropropane and 2,6-binitro-4-trifluoromethyl halogenated benzene at a molar ratio of 1.0:(2.0-2.2) to react in a system of salifying agent and organic solvent while refluxing by heating for water separation for 6-18 hours; and (2) concentrating the reactant liquor, cooling the reactant system, adding water to separate out solid product, filtering, washing and drying to obtain product crystal. The method has simple process, convenient solvent recovery, repeated used of the solvent, less three-waste, environment friendliness, and suitability for industrialized production. The obtained product has high yield and purity.

Description

2, the preparation method of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa 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 [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa 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] HFC-236fa 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] HFC-236fa 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] HFC-236fa 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 A20081003912400041
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-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa 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) HFC-236fa 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 HFC-236fa 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) HFC-236fa 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, the mixed volume ratio is 1: 0.05～10, strong polar non-proton organic solvent and 2, the envelope-bulk to weight ratio of two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) HFC-236fa 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] HFC-236fa 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) HFC-236fa 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] HFC-236fa 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 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 110.4 gram (0.80 mole) salt of wormwood, 1000 milliliters of N, dinethylformamide, 300 milliliters of benzene and 200 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 84.5 grams, the two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3 of 2-, the 5-3,5-dimethylphenyl] the HFC-236fa 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 HFC-236fa and theoretical amount (86.0 gram), calculate 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,5-3,5-dimethylphenyl] yield of HFC-236fa is 98.3%.
Embodiment 2
With 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 69.3 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 1200 milliliters of N,N-dimethylacetamide, 200 milliliters of benzene and 150 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 14 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 81.3 grams 2, the two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3 of 2-, the 5-3,5-dimethylphenyl] the HFC-236fa crystalline product, purity is 99.3%, 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 HFC-236fa and theoretical amount (86.0 gram), calculate 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,5-3,5-dimethylphenyl] yield of HFC-236fa is 94.5%.
Embodiment 3
With 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 980 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 1600 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 79.7 grams 2,2-is two, and [4-(2,6-nitro-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystalline product, purity is 99.6%, according to 2 of reality acquisition, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical yield (86.0 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 92.7%.
Embodiment 4
With 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 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, add water, separate out solid product, with hot wash 2～3 times, drying, obtain 68.4 grams 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystalline product, 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] HFC-236fa of 2-and theoretical amount (86.0 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 79.5%.
Embodiment 5
With 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 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 82.2 grams 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa, purity is 99.7%, obtain 2 according to reality, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (86.0 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 95.6%.
Embodiment 6
With 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 29.7 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 27.9 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, 82.8 gram (0.60 mole) salt of wormwood, 10.6 gram (0.10 mole) yellow soda ash, 3136 milliliters of N, dinethylformamide, 600 milliliters of benzene 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, drying, obtain 2 of 81.4 grams, 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystalline product, purity is 99.7%, obtain 2 according to reality, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (86.0 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 94.7%.
Embodiment 7
With 39.2 gram (0.10 moles) 2, two (the 4-hydroxyls-3 of 2-, the 5-3,5-dimethylphenyl) HFC-236fa, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 1.38 gram (0.01 mole) salt of wormwood, 200 milliliters of N-methyl-2-compare pyrrolidone, 3000 milliliters of benzene and 1000 milliliters of toluene 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 2 of 38.3 grams, 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] the HFC-236fa crystalline product, purity is 99.0%, obtain 2 according to reality, amount of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-and theoretical amount (86.0 gram), calculate 2, the yield of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa of 2-is 44.5%.

Claims (9)

1.2 the preparation method of two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] HFC-236fa 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) HFC-236fa 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] HFC-236fa 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 HFC-236fa, 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 HFC-236fa, 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 HFC-236fa, 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) HFC-236fa 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 HFC-236fa, it is characterized in that: described organic solvent is the mixture of water-insoluble organic solvent and strong polar non-proton organic solvent, and the mixed volume ratio is 1: 0.05～10.
6. according to claim 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, 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 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, 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 1,5 or 7 described 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3, the 5-3,5-dimethylphenyl] preparation method of HFC-236fa, it is characterized in that: described strong polar non-proton organic solvent and 2, the envelope-bulk to weight ratio of two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) HFC-236fa 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] HFC-236fa of 2-is characterized in that: it is that temperature is 80 ℃～200 ℃ reaction that described reflux is divided the water reaction.
CNA2008100391245A 2008-06-18 2008-06-18 Method for preparing 2,2di[4-(2,6-dinitryl-4-trifluoromethyl phenoxy) -3,5- dimethyl phenyl]hexa-fluorine propane Pending CN101293837A (en)

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Cited By (1)

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Open date: 20081029