CN101260043A - Method for preparing 2,2-di[4-(2.6-dinitro-4-trifluoromethylphenoxy)phenyl]hexafluoropropane - Google Patents
Method for preparing 2,2-di[4-(2.6-dinitro-4-trifluoromethylphenoxy)phenyl]hexafluoropropane Download PDFInfo
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- CN101260043A CN101260043A CNA2008100362929A CN200810036292A CN101260043A CN 101260043 A CN101260043 A CN 101260043A CN A2008100362929 A CNA2008100362929 A CN A2008100362929A CN 200810036292 A CN200810036292 A CN 200810036292A CN 101260043 A CN101260043 A CN 101260043A
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Abstract
The invention relates to a preparation method for 2,2-bis[4-(2,6-binitro-4-trifluoromethylphenoxy) phenyl] hexafluoropropane. The steps of the method are as follows: (1) 2,2-bis(4- hydroxyphenyl) hexafluoropropane and 2,6- binitro-4- trifluoromethyl halogeno benzene, the mol ratio of which is 1.0: 2.0 to 2.2, undergo heating, backflow and water diversion reactions for 6 to 18 hours in a salt forming agent-organic solvent system; (2) a reaction solution is condensed, and the reactant system is cooled down and is added with water for separating out solid products, and the products obtained are filtered, washed and dried, and thus 2,2-bis[4-(2,6-binitro-4-trifluoromethylphenoxy) phenyl] hexafluoropropane crystals are obtained. The invention has the advantages of simple operation, high yield and purity, convenient solvent recovery, repeated use, small three wastes and environmental protection, 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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:
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 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (4-hydroxy phenyl) 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) phenyl] 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-hydroxy phenyl) 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, and volume ratio is 1: 0.05～10, organic solvent and 2, and the envelope-bulk to weight ratio of two (4-hydroxy phenyl) 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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-hydroxy phenyl) 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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 33.6 gram (0.10 moles) 2, two (4-hydroxy phenyl) HFC-236fa of 2-, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 110.4 gram (0.80 mole) salt of wormwood, 1800 milliliters of N, dinethylformamide, 150 milliliters of benzene and 130 milliliters of toluene are put into reactor, stir, reflux divides the water reaction after 15 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 76.1 grams, two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the HFC-236fa crystalline products of 2-, purity is 99.5%, obtain 2 according to reality, amount of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-and theoretical amount (80.4 gram) calculate 2, the yield of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-is 94.7%.
Embodiment 2
With 33.6 gram (0.10 moles) 2, two (4-hydroxy phenyl) HFC-236fa of 2-, 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, the N-N,N-DIMETHYLACETAMIDE, 140 milliliters of benzene and 30 milliliters of dimethylbenzene 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 66.2 grams 2, two [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the HFC-236fa crystalline products of 2-, purity is 99.6%, obtain 2 according to reality, amount of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-and theoretical amount (80.4 gram) calculate 2, the yield of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-is 82.4%.
Embodiment 3
With 33.6 gram (0.10 moles) 2, two (4-hydroxy phenyl) HFC-236fa of 2-, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 540 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 900 milliliters of benzene and 200 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 adds water, separates out solid product, with hot wash 2～3 times, drying obtains 70.4 grams 2, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the HFC-236fa crystalline product, purity is 99.4%, and according to 2 of reality acquisition, 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of HFC-236fa and theoretical yield (80.4 gram), calculate 2, the yield of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-is 87.5%.
Embodiment 4
With 33.6 gram (0.10 moles) 2, two (4-hydroxy phenyl) HFC-236fa of 2-, 11.8 gram (0.21 mole) potassium hydroxide, 880 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 260 milliliters of benzene and 40 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 8 hours, add 55.9 gram (0.22 moles) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, reflux 5 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 70.2 grams 2, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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) phenyl] amount of HFC-236fa and theoretical amount (80.4 gram), calculate 2, the yield of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-is 87.3%.
Embodiment 5
With 33.6 gram (0.10 moles) 2, two (4-hydroxy phenyl) HFC-236fa of 2-, 66.2 gram (0.21 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 80.0 gram (0.80 mole) saleratus, 700 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of dimethyl sulfoxide (DMSO), 250 milliliters of benzene and 50 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, with hot wash 2～3 times, drying obtains 78.8 grams 2, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa, purity is 99.4%, obtains 2 according to reality, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of HFC-236fa and theoretical amount (80.4 gram), calculate 2, the yield of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-is 98.0%.
Embodiment 6
With 33.6 gram (0.10 moles) 2, two (4-hydroxy phenyl) HFC-236fa of 2-, 27.1 gram (0.10 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 34.7 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 20.0 gram (0.20 mole) saleratus, 170 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 2000 milliliters of benzene and 300 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 56.7 grams 2,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] the HFC-236fa crystalline product, purity is 99.0%, obtains 2 according to reality, and 2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] amount of HFC-236fa and theoretical amount (80.4 gram), calculate 2, the yield of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-is 70.5%.
Claims (9)
1. 2, the preparation method of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two (4-hydroxy phenyl) 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, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa of 2-.
2. according to claim 12,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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) phenyl] 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) phenyl] 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-hydroxy phenyl) 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) phenyl] 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 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) phenyl] 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 1 or 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] 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 or 52,2-is two, and [4-(2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] preparation method of HFC-236fa, it is characterized in that: described organic solvent and 2, the envelope-bulk to weight ratio of two (4-hydroxy phenyl) HFC-236fa of 2-is 5 milliliters～80 milliliters: 1 gram.
9. according to claim 12, the preparation method of two [4-(2, the 6-dinitrobenzene-4-4-trifluoromethylphenopendant) phenyl] HFC-236fa 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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| CNA2008100362929A CN101260043A (en) | 2008-04-18 | 2008-04-18 | Method for preparing 2,2-di[4-(2.6-dinitro-4-trifluoromethylphenoxy)phenyl]hexafluoropropane |
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| CNA2008100362929A CN101260043A (en) | 2008-04-18 | 2008-04-18 | Method for preparing 2,2-di[4-(2.6-dinitro-4-trifluoromethylphenoxy)phenyl]hexafluoropropane |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101492377B (en) * | 2009-02-25 | 2012-11-07 | 东华大学 | Process for producing 2,2-di[4-(2-trifluoromethyl-4-nitrophenoxy)phenyl] hexafluoroacetore |
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- 2008-04-18 CN CNA2008100362929A patent/CN101260043A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101492377B (en) * | 2009-02-25 | 2012-11-07 | 东华大学 | Process for producing 2,2-di[4-(2-trifluoromethyl-4-nitrophenoxy)phenyl] hexafluoroacetore |
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