CN101298428A - Preparation of 4,4'-bis (2,6- dinitro-4-trifluoromethyl phenoxyl)-3,3',5,5'-tetramethyl sulfobenzide - Google Patents
Preparation of 4,4'-bis (2,6- dinitro-4-trifluoromethyl phenoxyl)-3,3',5,5'-tetramethyl sulfobenzide Download PDFInfo
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- CN101298428A CN101298428A CNA2008100393005A CN200810039300A CN101298428A CN 101298428 A CN101298428 A CN 101298428A CN A2008100393005 A CNA2008100393005 A CN A2008100393005A CN 200810039300 A CN200810039300 A CN 200810039300A CN 101298428 A CN101298428 A CN 101298428A
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Abstract
The invention relates to a preparation method of 4, 4'-double (2, 6-dinitro-4- trifluoromethylphenoxy pendant)-3, 3', 5, 5'-tetramethyl sulfone which includes the steps: (1) carrying out heating, reflux and dividing reaction on 4, 4'-dihydroxy-3, 3', 5, 5'-tetramethyl sulfone and 2, 6-dinitro-4-trifluoromethylphenyl halide with mol ratio of 1.0 : 2.0 to 2.2 in a salt forming agent and organic solvent system for 6 to 18 hours; (2) condensing a reaction liquid and cooling a reactant system, adding water, separating out a solid product, filtering, washing and drying to obtain 4, 4'-double (2, 6-dinitro-4- trifluoromethylphenoxy pendant)-3, 3', 5, 5'-tetramethyl sulfone crystal. The preparation method of the invention is simple to be operated; the product yield and purity are high; the solvent is convenient for being recycled and can be repeatedly used; three wastes are less; the preparation method of the invention is environment friendly and suitable for industrialization production.
Description
Technical field
The invention belongs to the preparation field of aromatic organic compounds, particularly relate to a kind of 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone.
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)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone, 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).
4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5 of the present invention, the preparation method of 5 '-tetramethyl diphenyl sulfone comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone 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)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone 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 4,4 '-dihydroxyl-3,3 ', 5, the ratio of the mole number of 5 '-tetramethyl diphenyl sulfone 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 4,4 '-dihydroxyl-3,3 ', 5, the envelope-bulk to weight ratio of 5 '-tetramethyl diphenyl sulfone 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the commercial run of 5 '-tetramethyl diphenyl sulfone, 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) 4,4 '-dihydroxyl-3,3 ', 5, reaction raw materials convenient sources such as 5 '-tetramethyl diphenyl sulfone, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the molecular structure of 5 '-tetramethyl diphenyl sulfone.
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 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 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, 300 milliliters of benzene and 100 milliliters of toluene are put into reactor, stir, and 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 obtains 4,4 '-two (2 of 73.4 grams, 6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.8%, obtains 4,4 '-two (2 according to reality, 6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical amount (77.4 gram), calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 94.8%.
Embodiment 2
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 69.3 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 800 milliliters of N, the N-N,N-DIMETHYLACETAMIDE, 200 milliliters of benzene and 100 milliliters of dimethylbenzene are put into reactor, stir, and reflux divides the water reaction after 16 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 obtains 69.4 grams 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.6%, obtains 4,4 '-two (2 according to reality, 6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical amount (77.4 gram), calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 89.7%.
Embodiment 3
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 10.6 gram (0.10 mole) yellow soda ash, 1000 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 300 milliliters of benzene and 100 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 adds water, separate out solid product, with hot wash 2～3 times, drying, obtain 73.7 grams, 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.5%, according to 4 of reality acquisition, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical yield (77.4 gram) calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 95.2%.
Embodiment 4
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 11.8 gram (0.21 mole) potassium hydroxide, 1800 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 300 milliliters of benzene and 100 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 6 hours, adds 55.9 gram (0.22 moles) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, reflux 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, dry, obtain 71.7 grams, 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.6%, obtain 4 according to reality, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical amount (77.4 gram) calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 92.6%.
Embodiment 5
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 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), 150 milliliters of benzene and 80 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, separate out solid product, with hot wash 2～3 times, drying, obtain 74.5 grams, 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, purity is 99.1%, obtain 4 according to reality, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical amount (77.4 gram) calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 96.3%.
Embodiment 6
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 29.7 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 28.0 gram (0.11 mole) 2,6-dinitrobenzene-4-trifluoromethyl fluorobenzene, 31.8 gram (0.30 mole) yellow soda ash, 55.2 gram (0.40 mole) salt of wormwood, 2448 milliliters of N, dinethylformamide, 245 milliliters of benzene are put into reactor, stir, reflux divides the water reaction after 15 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3 of 75.5 grams, 3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.8%, obtain 4 according to reality, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical amount (77.4 gram) calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 97.6%.
Embodiment 7
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 54.1 gram (0.20 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 63.6 gram (0.60 mole) yellow soda ash, 153 milliliters of N-N-methyl-2-2-pyrrolidone N-s, 3060 milliliters of benzene 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 adds water, separate out solid product, with hot wash 2～3 times, drying, obtain 62.5 grams, 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.6%, according to 4 of reality acquisition, 4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical yield (77.4 gram) calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 80.7%.
Embodiment 8
With 30.6 gram (0.10 moles) 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone, 59.5 gram (0.22 mole) 2,6-dinitrobenzene-4-trifluoromethyl chlorinated benzene, 1.38 gram (0.01 mole) salt of wormwood, 800 milliliters of N, dinethylformamide, 100 milliliters of toluene are put into reactor, stir, and 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 obtains 4,4 '-two (2 of 27.6 grams, 6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone crystalline product, purity is 99.0%, obtains 4,4 '-two (2 according to reality, 6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the amount of 5 '-tetramethyl diphenyl sulfone and theoretical amount (77.4 gram), calculate 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the yield of 5 '-tetramethyl diphenyl sulfone is 35.6%.
Claims (9)
1.4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 4,4 '-dihydroxyl-3,3 ', 5,5 '-tetramethyl diphenyl sulfone 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)-3,3 ', 5,5 '-tetramethyl diphenyl sulfone.
2. according to claim 14,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone 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)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone 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 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone, it is characterized in that: described salt forming agent and 4,4 '-dihydroxyl-3,3 ', 5, the ratio of the mole number of 5 '-tetramethyl diphenyl sulfone is 0.10～8.00: 1.00.
5. according to claim 14,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone 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 54,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone 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)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone 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)-3,3 ', 5, the preparation method of 5 '-tetramethyl diphenyl sulfone, it is characterized in that: described strong polar non-proton organic solvent and 4,4 '-dihydroxyl-3,3 ', 5, the envelope-bulk to weight ratio of 5 '-tetramethyl diphenyl sulfone is 5 milliliters～80 milliliters: 1 gram.
9. 4,4 '-two (2,6-dinitrobenzene-4-4-trifluoromethylphenopendant)-3,3 ', 5 according to claim 1, the preparation method of 5 '-tetramethyl diphenyl sulfone is characterized in that: it is that temperature is 80 ℃～200 ℃ reaction that described reflux is divided the water reaction.
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| CN101591278B (en) * | 2009-07-03 | 2012-11-07 | 东华大学 | Method for preparing 4,4'-bis(4-nitro-2-trifluoromethylphenoxy)diphenylsulfone |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101591278B (en) * | 2009-07-03 | 2012-11-07 | 东华大学 | Method for preparing 4,4'-bis(4-nitro-2-trifluoromethylphenoxy)diphenylsulfone |
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