CN101279917A - Preparation of 4,4'-bis(2,6-dinitro-4-trifluoromethylphenoxy) benzophenone - Google Patents

Preparation of 4,4'-bis(2,6-dinitro-4-trifluoromethylphenoxy) benzophenone Download PDF

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CN101279917A
CN101279917A CNA2008100378058A CN200810037805A CN101279917A CN 101279917 A CN101279917 A CN 101279917A CN A2008100378058 A CNA2008100378058 A CN A2008100378058A CN 200810037805 A CN200810037805 A CN 200810037805A CN 101279917 A CN101279917 A CN 101279917A
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dinitrobenzene
benzophenone
trifluoromethylphenopendant
preparation
trifluoromethyl
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虞鑫海
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Donghua University
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract

The invention relates to a method to prepare 4,4`-bi(2,6-binitro-4- trifluoromethyl-phenoxyl)benzophenone, including the following steps: (1), 4,4`-dihydroxy- benzophenone and 2,6-binitro-4-trifluoromethyl-halogenated benzene based on molar ratio of 1.0:2.0-2.2 are heated to reflux and react for 6-18 hours in a system with salt forming agent and organic solvent;(2), the solution after reaction is concentrated and cooled, and then water is added to separate out the solid product, and after that the solution is filtrated, washed and dried, getting 4,4`-bi(2,6-binitro-4-trifluoromethyl-phenoxyl)benzophenone crystalloid. The method is simple in operation with high yield and product is high in purity; the solvent is convenient to recycle and can be used repeatedly; with little wastes (gas, liquid and solid) and being environment-friendly, the method is applicable to industrial production.

Description

The preparation method of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone
Technical field
The invention belongs to the preparation field of aromatic organic compounds, particularly relate to a kind of preparation method of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone.
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).
4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 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 the preparation method of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone 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 preparation method of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone, 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 A20081003780500031
Wherein, X is a halogen atom, i.e. fluorine (F), chlorine (Cl), bromine (Br), iodine (I).
The preparation method of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone of the present invention comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 4,4 '-dihydroxy benaophenonel and 2,6-dinitrobenzene-4-trifluoromethyl halogeno-benzene, in salt forming agent, organic solvent system, reflux was 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone 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 4, the ratio of the mole number of 4 '-dihydroxy benaophenonel 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, and volume ratio is 1: 0.5～10, strong polar non-proton organic solvent and 4, and the envelope-bulk to weight ratio of 4 '-dihydroxy benaophenonel 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 80 ℃～150 ℃ that described reflux is divided the temperature range of water reaction.
Beneficial effect of the present invention:
(1) the present invention is the commercial run of preparation 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone, 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) 4, reaction raw materials convenient sources such as 4 '-dihydroxy benaophenonel, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 4, the molecular structure of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone.
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 21.4 gram (0.10 moles) 4,4 '-dihydroxy benaophenonel, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 110.4 gram (0.80 mole) salt of wormwood, 1712 milliliters of N, dinethylformamide, 150 milliliters of benzene and 25 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 4 of 67.0 grams, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone crystalline product, purity is 99.5%, obtain 4 according to reality, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone and theoretical amount (68.2 gram) calculate 4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 98.2%.
Embodiment 2
With 21.4 gram (0.10 moles) 4,4 '-dihydroxy benaophenonel, 69.3 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 10.0 gram (0.10 mole) saleratus, 10.6 gram (0.10 mole) yellow soda ash, 55.2 gram (0.40 mole) salt of wormwood, 200 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 600 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 200 milliliters of benzene and 30 milliliters of dimethylbenzene 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 63.7 grams 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone crystalline product, purity is 99.7%, obtain 4 according to reality, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone and theoretical amount (68.2 gram) calculate 4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 93.4%.
Embodiment 3
With 21.4 gram (0.10 moles) 4,4 '-dihydroxy benaophenonel, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 110 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 200 milliliters of benzene and 20 milliliters of dichlorobenzenes 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 53.1 grams 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone crystalline product, purity is 99.4%, according to 4,4 '-two (2 of reality acquisition, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of benzophenone and theoretical yield (68.2 gram), the yield that calculates 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 77.8%.
Embodiment 4
With 21.4 gram (0.10 moles) 4,4 '-dihydroxy benaophenonel, 11.8 gram (0.21 mole) potassium hydroxide, 1000 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 300 milliliters of benzene and 50 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 8 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 44.6 grams 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone crystalline product, purity is 99.3%, obtains 4,4 '-two (2 according to reality, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of benzophenone and theoretical amount (68.2 gram), the yield that calculates 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 65.4%.
Embodiment 5
With 21.4 gram (0.10 moles) 4,4 '-dihydroxy benaophenonel, 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, 300 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 61.1 grams 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone, purity is 99.7%, obtains 4,4 '-two (2 according to reality, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of benzophenone and theoretical amount (68.2 gram), the yield that calculates 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 89.6%.
Embodiment 6
With 42.8 gram (0.20 moles) 4,4 '-dihydroxy benaophenonel, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 66.2 gram (0.21 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 110.4 gram (0.80 mole) salt of wormwood, 3000 milliliters of N, dinethylformamide, 100 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 420 milliliters of benzene 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 adds water, separates out solid product, with hot wash 2～3 times, drying obtains 4,4 '-two (2 of 133.0 grams, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone crystalline product, purity is 99.6%, obtains 4,4 '-two (2 according to reality, 6-dinitrobenzene-4-4-trifluoromethylphenopendant) amount of benzophenone and theoretical amount (136.4 gram), the yield that calculates 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 97.5%.
Embodiment 7
With 21.4 gram (0.10 moles) 4,4 '-dihydroxy benaophenonel, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 11.0 gram (0.08 mole) salt of wormwood, 600 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 400 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 350 milliliters of benzene and 30 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 10 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 4 of 56.2 grams, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone crystalline product, purity is 99.5%, obtain 4 according to reality, the amount of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone and theoretical amount (68.2 gram) calculate 4, the yield of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone is 82.4%.

Claims (9)

1.4 the preparation method of 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 4,4 '-dihydroxy benaophenonel and 2,6-dinitrobenzene-4-trifluoromethyl halogeno-benzene, in salt forming agent, organic solvent system, reflux was 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone.
2. according to claim 14,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of benzophenone, 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 14,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of benzophenone 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 the preparation method of claim 1 or 3 described 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone, it is characterized in that: described salt forming agent and 4, the ratio of the mole number of 4 '-dihydroxy benaophenonel is 0.80～8.00: 1.00.
5. according to claim 14,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of benzophenone 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: 0.5～10.
6. according to claim 54,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of benzophenone 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 54,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of benzophenone, 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) preparation method of benzophenone is characterized in that: described strong polar non-proton organic solvent and 4, the envelope-bulk to weight ratio of 4 '-dihydroxy benaophenonel are 5 milliliters～80 milliliters: 1 gram.
9. the preparation method of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant) benzophenone according to claim 1 is characterized in that: it is 80 ℃～150 ℃ that described reflux is divided the temperature range of water reaction.
CNA2008100378058A 2008-05-21 2008-05-21 Preparation of 4,4'-bis(2,6-dinitro-4-trifluoromethylphenoxy) benzophenone Pending CN101279917A (en)

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Open date: 20081008