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Preparation of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-t-butylbenzene

A technology of nitrophenoxy and nitrotrifluoromethylbenzene is applied in the field of preparation of aromatic fluorine-containing organic compound benzene, and can solve the problem of increasing raw material cost and production cost, increasing chemical equipment and personnel cost, and increasing chemical unit operation and other problems, to achieve the effect of convenient source of raw materials, low cost and simplified process

Inactive Publication Date: 2012-11-07
DONGHUA UNIV
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  • Description
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  • Application Information

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Problems solved by technology

[0010] But, the shortcoming of this method is: (1) the organic solvent kind that involves is more, as DMF, methyl alcohol etc.
This will inevitably lead to a large amount of waste water, and also increases the cost of waste water treatment, meanwhile, it also needs to consume a large amount of methanol solvent
These are all unfavorable for environmental protection and reduce production cost; (3) the crude product that precipitates out also needs to do further recrystallization in DMF / methanol mixed solution, to purify product
This not only increases the chemical unit operation, increases the cost of chemical equipment and personnel, but also increases the cost of raw materials and production costs, and also increases the cost of the three wastes.

Method used

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  • Preparation of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-t-butylbenzene
  • Preparation of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-t-butylbenzene
  • Preparation of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-t-butylbenzene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 22.2 grams (0.10 moles) of 2,5-di-tertbutyl-1,4-hydroquinone (DTBHQ), 49.6 grams (0.22 moles) of 2-chloro-5-nitrotrifluoromethylbenzene (CNB- TF), 41.4 grams (0.30 moles) of potassium carbonate, 500 milliliters of N, N-dimethylformamide and 500 milliliters of toluene mixed solvent are put into reaction kettle, stir, be heated to 120 ℃-150 ℃, reflux azeotrope After reacting with water for 15 hours, filter while it is hot, remove the filter residue, concentrate the mother liquor, recover the solvent for recycling, cool and stand still, and precipitate milky yellow solid crystalline product, filter, wash with pure water 2 to 3 times, and dry to obtain 57.0 grams of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-tert-butylbenzene (DNDTBHQ-2TF) milky yellow solid product (theoretical yield is 60.0 g), the purity is 99.7%, the melting point is 265.5°C-266.8°C (WRR melting point instrument, the initial setting temperature is 258.0°C, the heating rate is 1.5°C / min), and its F...

Embodiment 2

[0033]22.2 grams (0.10 moles) of 2,5-di-tert-butyl-1,4-hydroquinone (DTBHQ), 54.1 grams (0.24 moles) of 2-chloro-5-nitrotrifluoromethylbenzene (CNB- TF), 62.1 grams (0.45 moles) of salt of wormwood, 600 milliliters of N-methyl-2-pyrrolidone, 160 milliliters of N, N-dimethylacetamide and 100 milliliters of benzene and 55 milliliters of xylene mixed solvents are put into reaction kettle , stirred, heated to 120°C-180°C, after 12 hours of azeotropic water separation reaction, filtered while hot, removed the filter residue, concentrated the mother liquor, recovered the solvent for recycling, cooled and stood still, and precipitated milky yellow solid product, filtered, and used pure Washed with water for 2-3 times and dried to obtain 55.2 g of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-tert-butylbenzene (DNDTBHQ-2TF) milky yellow Solid product (theoretical yield is 60.0 grams), according to theoretical yield and actual obtain 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-...

Embodiment 3

[0035] 22.2 grams (0.10 moles) of 2,5-di-tertbutyl-1,4-hydroquinone (DTBHQ), 45.1 grams (0.20 moles) of 2-chloro-5-nitrotrifluoromethylbenzene (CNB- TF), 27.6 grams (0.20 moles) of potassium carbonate, 340 milliliters of N-methyl-2-pyrrolidone, 700 milliliters of o-dichlorobenzene and 1000 milliliters of toluene are put into the reaction kettle, stirred, and heated to 120°C-180°C After refluxing and azeotropic water separation for 20 hours, filter while it is hot, remove the filter residue, concentrate the mother liquor, recover the solvent for recycling, cool and stand still, and precipitate a milky yellow solid product, filter, wash 2 to 3 times with pure water, and dry to obtain 57.6 grams of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-tert-butylbenzene (DNDTBHQ-2TF) milky yellow solid product, the purity is 99.7%, according to actual The amount and theoretical yield (60.0 g) of 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-tert-butylbenzene (DNDTBHQ-2TF) obtained w...

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Abstract

The invention relates to a method for preparing 1, 4-dual (2-trifluoromethyl-4-nitrophenoxy)-2, 5-dual tert-butylbenzene, comprising the steps: (1) 2, 5-dual tert-butylbenzene-1, 4-hydroquinone and 2-chlorine-5-nitryl trifluoromethyl benzene are dissolved into the mixed solvent of salt forming agent, strongly polar aprotic organic solvent and organic entrainer according to the mol ratio of 1.0:2.0-2.4, and heated for azeotropic water diversion reaction for 12-20h; (2) the mixture is filtered in heat, filter residue is removed, master liquor is concentrated and cooled in a static way, and milky yellow crystal product is separated out, filtered, washed and dried to obtain the 1, 4-dual (2-trifluoromethyl-4-nitrophenoxy)-2, 5-dual tert-butylbenzene. The preparation method has simple operation, wide raw material source and low cost, and does not relate to corrosive substance; the using sorts of the organic solvent are less, and the organic solvent can be repeatedly recycled and environment-friendly; furthermore, the yield of the product reaches over 92%, and the purity reaches 99.7%, so that the method is suitable for commercial process.

Description

technical field [0001] The invention belongs to the field of preparation of aromatic fluorine-containing organic compound benzene, in particular to 1,4-bis(2-trifluoromethyl-4-nitrophenoxy)-2,5-di-tert-butylbenzene method of preparation. Background technique [0002] Aromatic polyimide has excellent thermal stability, chemical stability, excellent mechanical properties, electrical properties and resistance to organic solvents, and has been widely used in aerospace, electronic microelectronics, electrical and other fields. Because of its high temperature resistance, high strength, corrosion resistance, good insulation, and simple film forming process, it is an excellent functional material. [0003] Fluorine-containing polyimide materials not only have the above-mentioned excellent properties, but also have very excellent optical transparency, flame retardancy and excellent molding processability. In addition, its dielectric constant, dielectric loss and water absorption ar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/38C07C201/12
Inventor 虞鑫海
Owner DONGHUA UNIV
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