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Process for producing 3,3',5,5'-tetramethyl-4,4'-di(2-trifluoromethyl-4-nitrophenoxy)biphenyl

A technology of nitrotrifluoromethylbenzene and nitrophenoxy is applied in the field of preparation of aromatic fluorine-containing biphenyls, can solve problems such as unfavorable environmental protection, increase three wastes, reduce production costs, etc., and achieves convenient source of raw materials, Effects with few types of use and simple operation

Inactive Publication Date: 2009-07-29
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] But the shortcoming of this method is: (1) the yield of product is on the low side, and recrystallization yield is 78%, and total yield only has 97%*78%<76%; (2) the organic solvent kind that involves is many, as DMF, methanol, etc.
This will inevitably lead to a large amount of waste water, which also increases the cost of waste water treatment, is not conducive to environmental protection and reduces production costs; (4) 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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  • Process for producing 3,3',5,5'-tetramethyl-4,4'-di(2-trifluoromethyl-4-nitrophenoxy)biphenyl
  • Process for producing 3,3',5,5'-tetramethyl-4,4'-di(2-trifluoromethyl-4-nitrophenoxy)biphenyl
  • Process for producing 3,3',5,5'-tetramethyl-4,4'-di(2-trifluoromethyl-4-nitrophenoxy)biphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 24.2 grams (0.10 moles) of 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (3355TMBP), 47.4 grams (0.21 moles) of 2-chloro-5-nitrotrifluoro A mixed solvent of methylbenzene (CNB-TF), 41.4 grams (0.30 moles) of potassium carbonate, 800 milliliters of N, N-dimethylformamide and 400 milliliters of toluene was put into a reaction kettle, stirred, and heated to 100° C.-120 ℃, reflux water separation reaction for 10 hours, continue to heat up, and react at 150°C for 1 hour, filter while 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, Washed 2 to 3 times with pure water, dried to obtain 59.0 grams of 3,3',5,5'-tetramethyl-4,4'-bis(2-trifluoromethyl-4-nitrophenoxy ) biphenyl (DNTMBP-2TF) milky yellow solid product (theoretical yield is 62.1 grams), the purity is 99.8%, and the fusing point is 267.5 ℃ (DSC differential scanning calorimeter, nitroge...

Embodiment 2

[0036] 24.2 grams (0.10 moles) of 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (3355TMBP), 58.6 grams (0.26 moles) of 2-chloro-5-nitrotrifluoro Toluene (CNB-TF), 11.0 grams (0.08 moles) of potassium carbonate, 200 milliliters of N-methyl-2-pyrrolidone, 3600 milliliters of N, N-dimethylacetamide and 260 milliliters of xylene mixed solvents were put into the reaction Stir in the kettle, heat to 100°C-180°C, react for 15 hours, filter while hot, remove the filter residue, concentrate the mother liquor, recover the solvent for recycling, cool and stand still, precipitate a milky yellow solid product, filter, and wash with pure water 2 to 3 times, dried to obtain 57.7 grams of 3,3',5,5'-tetramethyl-4,4'-bis(2-trifluoromethyl-4-nitrophenoxy)biphenyl (DNTMBP -2TF) Creamy yellow solid product (theoretical yield: 62.1 g) with a purity of 99.5%.

[0037] Obtain 3,3',5,5'-tetramethyl-4,4'-bis(2-trifluoromethyl-4-nitrophenoxy)biphenyl (DNTMBP-2TF) according to theoretical yield and actua...

Embodiment 3

[0039] 24.2 grams (0.10 moles) of 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (3355TMBP), 45.1 grams (0.20 moles) of 2-chloro-5-nitrotrifluoro The mixed solvent of methylbenzene (CNB-TF), 10.6 grams (0.10 moles) sodium carbonate, 48.3 grams (0.35 moles) salt of wormwood, 350 milliliters of N-methyl-2-pyrrolidone and 700 milliliters of toluene is put into reaction kettle, Stir, heat to 100°C-130°C, reflux and divide water for 8 hours, continue to heat up, and react at 180°C for 0.5 hours, filter while hot, remove filter residue, concentrate mother liquor, recover solvent for recycling, cool and stand still, and precipitate milk The yellow solid product was filtered, washed 2 to 3 times with pure water, and dried to obtain 55.9 grams of 3,3',5,5'-tetramethyl-4,4'-bis(2-trifluoromethyl-4- Nitrophenoxy)biphenyl (DNTMBP-2TF) milky yellow solid product with a purity of 99.6%.

[0040] According to the amount and Theoretical yield (62.1 g) was calculated to give 3,3',5,5'-tetramet...

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Abstract

The invention relates to a preparation method of 3, 3', 5, 5'- tetramethyl -4, 4'-double (2-trifluoromethane-4-nitrobenzene oxy) diphenyl. The invention comprises the following steps: (1) mixing 3, 3', 5, 5'-tetramethyl-4, 4'-dihydroxy diphenyl and 2-chlorine-5-nitryl trifluoromethyl benzene by the mol ratio of 1.0:2.0-2.6, and then adding the mixture into a mixed solvent of salifying agent, soluble organic solvent and non-soluble organic solvent for reaction for 4 to 15 hours at 100 to 180 DEG C; (2) filtering when the solvent is hot, eliminating filter residue, condensing mother liquid, cooling and stewing to precipitate a butter yellow solid product, and then filtering, washing and drying the product to obtain the butter yellow solid powder of 3, 3', 5, 5'-tetramethyl-4, 4'-double(2- trifluoromethyl-4-nitrobenzene oxy) diphenyl. The method with simple process, low cost, environment-friendliness and high purity and yield is applicable to the industrial production.

Description

technical field [0001] The invention belongs to the field of preparation of aromatic fluorine-containing biphenyls, in particular to a 3,3',5,5'-tetramethyl-4,4'-bis(2-trifluoromethyl-4-nitro The preparation method of phenoxy)biphenyl. 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 are ...

Claims

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Application Information

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