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Preparation method of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride

A technology of biphenyl dicarboxylic acid chloride and trifluoromethyl, applied in the field of preparation of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride, can solve the problem of long synthetic route, High production cost, low reaction yield and other problems, to achieve the effect of short synthesis route, low production cost and high reaction yield

Active Publication Date: 2021-10-15
江苏尚莱特医药化工材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method are: (1) the synthetic route is long and requires six steps; (2) the total yield is low, only about 12%, especially the coupling reaction yield is only 35.2%; (3) the cyanation reaction requires The use of highly toxic substances, such as cuprous cyanide, sodium cyanide, etc., leads to lower safety; (4) It is not suitable for large-scale industrial production
The disadvantages of this method are: (1) the second-step reaction requires the use of expensive organic noble metal catalyst bis(triphenylphosphine) palladium dichloride (II), resulting in higher production costs; (2) the first two steps of reaction yield The rate is also not high, only about 70%, and it is also not suitable for industrialized large-scale production
The deficiency of this method is: (1) yield is relatively low, especially cyanide reaction yield only has 15.2% (cuprous cyanide) and 25.6% (copper cyanide complex); Toxic substances, resulting in lower safety, also not suitable for industrialized large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0021] The preparation method of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride of this embodiment has the following steps:

[0022] a. At room temperature (20±5°C, the same below), add 180g of 40wt% hydrobromic acid and 32.0g of 2,2'-bis(trifluoromethyl)-4,4'- Diaminobiphenyl, heated to 65±1°C, stirred to dissolve, then cooled to 2±1°C, slowly added dropwise sodium nitrite aqueous solution (17.3g sodium nitrite dissolved in 35g water), 2~3h to finish, drop to finish The reaction was incubated at this temperature for 1 h to obtain a diazonium salt solution.

[0023] Then the diazonium salt solution obtained above was slowly added to the cuprous bromide hydrobromic acid solution at a temperature of 45±1°C (37.3g of cuprous bromide was added to 40mL of 40wt% hydrobromic acid). Insulate the reaction at this temperature until complete.

[0024] After the reaction, cool to room temperature, extract three times with methyl tert-butyl ether (80mL×3), let stand t...

Embodiment 2）

[0030] The preparation method of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride of this embodiment has the following steps:

[0031] a. At room temperature, add 500g of dilute sulfuric acid with a concentration of 20wt% and 50.0g of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl into the reaction flask, and heat to 65±1 ℃, stir to dissolve, then lower the temperature to 2±1℃, slowly add sodium nitrite aqueous solution (27g sodium nitrite dissolved in 55g water) dropwise, 2~3h to finish the drop, keep warm at this temperature for 1h to obtain diazonium saline solution.

[0032] Then the diazonium salt solution obtained above was slowly added to the cuprous bromide hydrobromic acid solution at a temperature of 40±1°C (58g of cuprous bromide was added to 68mL of 40wt% hydrobromic acid), at which The reaction is kept under temperature until complete.

[0033] After the reaction, cool down to room temperature, extract three times with methyl tert-butyl ether (...

Embodiment 3）

[0039] The preparation method of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride of this embodiment has the following steps:

[0040] a. At room temperature, add 300g of dilute sulfuric acid with a concentration of 15wt% and 30.0g of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl into the reaction flask, and heat to 65±1 ℃, stir to dissolve, then lower the temperature to 2±1℃, slowly add sodium nitrite aqueous solution (16.2g sodium nitrite dissolved in 33g water) dropwise, 2~3h to complete the drop, keep warm at this temperature for 1h to obtain the weight nitrogen salt solution.

[0041] Then the diazonium salt solution obtained above was slowly added to the cuprous bromide hydrobromic acid solution at a temperature of 45±1°C (35g cuprous bromide was added to 40mL of hydrobromic acid with a concentration of 40wt%). The reaction is kept under temperature until complete.

[0042] After the reaction was completed, cool to room temperature, first extract thr...

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PUM

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Abstract

The invention discloses a preparation method of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride, which comprises the following steps: a. taking 2,2'-bis(trifluoromethyl) base)-4,4'-diaminobiphenyl as the starting material, firstly through the diazotization reaction, and then through the bromination reaction to obtain 2,2'-bis(trifluoromethyl)-4,4'-dibromide Biphenyl; b, 2,2'-bis(trifluoromethyl)-4,4'-dibromobiphenyl undergoes a Grignard reaction / substitution reaction followed by reaction with carbon dioxide to give 2,2'-bis(trifluoromethyl) base)-4,4'-biphenyldicarboxylic acid; c, 2,2'-bis(trifluoromethyl)-4,4'-biphenyldicarboxylic acid was chlorinated to obtain 2,2'-bis(trifluoromethyl) Fluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride. The method of the invention has short synthesis route, low production cost, especially high reaction yield, no need of highly toxic substances, high safety, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride. Background technique [0002] Fluorine-containing polymer materials are widely used due to their good chemical corrosion resistance, atmospheric aging resistance, excellent dielectric properties, unique low surface energy, wide processing window and large service temperature range. Nuclear energy, aerospace, electronics, machinery manufacturing, medicine, chemical industry and other industries. [0003] 2,2'-bis(trifluoromethyl)-4,4'-biphenyl dicarboxylic acid chloride is an important monomer for the synthesis of high-performance fluorine-containing materials, polybenzimidazole and polybenzoxazole, etc. Polymer materials have special thermal, chemical and mechanical stability and good dielectric properties at high temperatures, and have broad application prospects in hi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/60C07C63/72
CPCC07C17/093C07C51/15C07C51/60C07C63/72C07C25/18
Inventor 胡国宜胡锦平吴建华张培锋奚小金
Owner 江苏尚莱特医药化工材料有限公司
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