CN101234983A - Method for preparing 2,6-dimethyl-1,4-di(2,4-dinitrophenoxy)benzene - Google Patents
Method for preparing 2,6-dimethyl-1,4-di(2,4-dinitrophenoxy)benzene Download PDFInfo
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- CN101234983A CN101234983A CNA200810034254XA CN200810034254A CN101234983A CN 101234983 A CN101234983 A CN 101234983A CN A200810034254X A CNA200810034254X A CN A200810034254XA CN 200810034254 A CN200810034254 A CN 200810034254A CN 101234983 A CN101234983 A CN 101234983A
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Abstract
The invention relates to a preparation method of 2, 6-dimethyl-1, 4-bis-(2, 4-dinitrophenoxy) benzene, comprising: (1) heating to reflux and segregate water for 3-18h to treat 2, 6-dimethyl-hydroquinone and 2, 4-dinitro halogenated benzene at the mol ratio of 1.0:2.0 to 2.2, in a system of salt forming agent and organic solvent; (2) concentrating reaction liquid, cooling the reactant system, adding water, precipitating solid product, filtering, washing and drying to obtain russet brown 2, 6-dimethyl-1, 4-bis-(2, 4-dinitrophenoxy) benzene. The preparation method of 2, 6-dimethyl-1, 4-bis-(2, 4-dinitrophenoxy) benzene has simple operation, high yield and purity, wherein the solvent can be recovered easily and repeatedly used. The invention has low generation of three wastes and environment-friendly property, which is suitable for industrial production.
Description
Technical field
The invention belongs to the preparation field of aromatic organic compounds, particularly relate to a kind of 2,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-.
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).
2,6-dimethyl-1, two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-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 2,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-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 2,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-, 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 2,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2,6-dimethyl-Resorcinol and 2,4-dinitrobenzene halogeno-benzene, in salt forming agent, organic solvent system, reflux was divided water reaction 3～18 hours;
(2) concentration of reaction solution, the cooling reactant system adds water, separates out solid product, filter, washing, drying obtains 2,6-dimethyl-1, two (2,4-2,4-dinitrophenoxy base) the benzene crystal of 4-.
Described 2,4-dinitrobenzene halogeno-benzene is selected from 2,4-dinitrobenzene fluorobenzene, 2,4-dinitro-chloro-benzene, 2,4-dinitrobenzene bromobenzene, 2, one or more mixtures in the 4-dinitrobenzene 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 6-dimethyl-Resorcinol 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, and organic solvent and 2, the envelope-bulk to weight ratio of 6-dimethyl-Resorcinol are 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 2,6-dimethyl-1, and the commercial run of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-, 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 (4) 2,6-dimethyl-Resorcinol, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 2,6-dimethyl-1, the molecular structure of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-.
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 13.8 gram (0.10 moles) 2,6-dimethyl-Resorcinol, 44.6 gram (0.22 mole) 2, the 4-dinitro-chloro-benzene, 110.4 gram (0.80 mole) salt of wormwood, 700 milliliters of N, dinethylformamide and 180 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, hot wash 2～3 times, drying obtains 45.0 grams 2,6-dimethyl-1, two (2,4-2,4-dinitrophenoxy base) the benzene crystalline products of 4-, purity is 99.5%, obtain 2 according to reality, 6-dimethyl-1, amount of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-and theoretical amount (47.0 gram), calculate 2,6-dimethyl-1, the yield of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-is 95.7%.
Embodiment 2
With 13.8 gram (0.10 moles) 2,6-dimethyl-Resorcinol, 54.4 gram (0.22 mole) 2,4-dinitrobenzene bromobenzene, 55.2 gram (0.40 mole) salt of wormwood, 150 milliliters of N, N-N,N-DIMETHYLACETAMIDE and 15 milliliters of dimethylbenzene are put into reactor, stir, and reflux divides the water reaction after 6 hours, concentration of reaction solution, reclaim solvent to recycle, the cooling reactant system adds water, separate out solid product, hot wash 2～3 times, drying obtains 43.8 grams 2,6-dimethyl-1, two (2,4-2,4-dinitrophenoxy base) the benzene crystalline products of 4-, purity is 99.3%, obtain 2 according to reality, 6-dimethyl-1, amount of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-and theoretical amount (47.0 gram), calculate 2,6-dimethyl-1, the yield of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-is 93.2%.
Embodiment 3
With 13.8 gram (0.10 moles) 2,6-dimethyl-Resorcinol, 40.5 gram (0.20 mole) 2, the 4-dinitro-chloro-benzene, 10.6 gram (0.10 mole) yellow soda ash, 40 milliliters of N-N-methyl-2-2-pyrrolidone N-s and 15 milliliters of dichlorobenzenes are put into reactor, stir, reflux divides the water reaction after 16 hours, and concentration of reaction solution reclaims solvent to recycle, the cooling reactant system, add water, separate out solid product, hot wash 2～3 times, dry, obtain 42.9 grams 2,6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) benzene crystalline product, purity is 99.1%, according to 2 of reality acquisition, 6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) amount of benzene and theoretical yield (47.0 gram) calculate 2,6-dimethyl-1, the yield of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-is 91.2%.
Embodiment 4
With 13.8 gram (0.10 moles) 2,6-dimethyl-Resorcinol, 40.9 gram (0.22 mole) 2,4-dinitrobenzene fluorobenzene, 11.8 gram (0.21 mole) potassium hydroxide, 20 milliliters of N, dinethylformamide and 400 milliliters of dichlorobenzenes are put into reactor, stir, and 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, hot wash 2～3 times, drying obtains 36.3 grams 2,6-dimethyl-1, two (2,4-2,4-dinitrophenoxy base) the benzene crystalline products of 4-, purity is 95.2%, obtain 2 according to reality, 6-dimethyl-1, amount of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-and theoretical amount (47.0 gram), calculate 2,6-dimethyl-1, the yield of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-is 77.2%.
Embodiment 5
With 13.8 gram (0.10 moles) 2,6-dimethyl-Resorcinol, 51.9 gram (0.21 mole) 2,4-dinitrobenzene bromobenzene, 80.0 gram (0.80 mole) saleratus, 300 milliliters of dimethyl sulfoxide (DMSO) and 100 milliliters of dimethylbenzene are put into reactor, stir, reflux divides the water reaction after 3 hours, and concentration of reaction solution reclaims solvent to recycle, the cooling reactant system, add water, separate out solid product, hot wash 2～3 times, dry, obtain 41.6 grams 2,6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) benzene, purity is 99.1%, obtains 2 according to reality, 6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) amount of benzene and theoretical amount (47.0 gram) calculate 2,6-dimethyl-1, the yield of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-is 88.4%.
Claims (9)
1.2,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-comprises the following steps:
(1) mol ratio be 1.0: 2.0～2.2 2,6-dimethyl-Resorcinol and 2,4-dinitrobenzene halogeno-benzene, in salt forming agent, organic solvent system, reflux was divided water reaction 3～18 hours;
(2) concentration of reaction solution, the cooling reactant system adds water, separates out solid product, filter, washing, drying gets 2,6-dimethyl-1, two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-.
2. according to claim 12,6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) preparation method of benzene is characterized in that: described 2,4-dinitrobenzene halogeno-benzene is selected from 2,4-dinitrobenzene fluorobenzene, 2,4-dinitro-chloro-benzene, 2,4-dinitrobenzene bromobenzene, 2, one or more mixtures in the 4-dinitrobenzene phenyl-iodide.
3. according to claim 12,6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) preparation method of benzene 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 2,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-, it is characterized in that: described salt forming agent and 2, the ratio of the mole number of 6-dimethyl-Resorcinol is 0.10～8.00: 1.00.
5. according to claim 12,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-, 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 52,6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) preparation method of benzene 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 52,6-dimethyl-1,4-two (2,4-2,4-dinitrophenoxy base) preparation method of benzene, 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 52,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-, it is characterized in that: described organic solvent and 2, the envelope-bulk to weight ratio of 6-dimethyl-Resorcinol are 5 milliliters～80 milliliters: 1 restrains.
9. according to claim 12,6-dimethyl-1, the preparation method of two (2, the 4-2,4-dinitrophenoxy base) benzene of 4-is characterized in that: it is that temperature is 80 ℃～200 ℃ reaction that described reflux is divided the water reaction.
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|---|---|---|---|
| CNA200810034254XA CN101234983A (en) | 2008-03-05 | 2008-03-05 | Method for preparing 2,6-dimethyl-1,4-di(2,4-dinitrophenoxy)benzene |
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| CNA200810034254XA CN101234983A (en) | 2008-03-05 | 2008-03-05 | Method for preparing 2,6-dimethyl-1,4-di(2,4-dinitrophenoxy)benzene |
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Open date: 20080806 |