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Synthesis method of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl

A technology of diaminobiphenyl and trifluoromethyl, which is applied in the field of synthesis of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, which can solve the problems of difficult access and high reaction temperature , long synthetic route and other problems, to achieve the effect of convenient price, mild reaction conditions and short synthetic route

Active Publication Date: 2021-06-11
大连新阳光材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The disadvantages of this method are: (1) A large amount of inorganic acid needs to be used, which not only leads to the production of a large amount of waste acid, which is not friendly to the environment, but also has a large amount of by-products mixed in the waste acid, which increases the difficulty and cost of waste acid treatment ; (2) The total yield is only about 50%, which is not suitable for industrial production
[0008] The disadvantages of this method are: (1) Ullmann coupling reaction temperature is high, side reactions are many, and the amount of catalyst is large, which not only increases the production cost, but also produces metal pollution, which is not friendly to the environment; (2) The total yield is less than 40%, and it is not suitable for industrialized production
[0010] The disadvantages of this method are: (1) the price of the starting material 4-nitro-3-trifluoromethylaniline is relatively high and it is not easy to obtain; (2) the synthetic route is long and the total yield is lower, less than 30%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0038] The synthesis method of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl in this example has the following steps:

[0039] ①Add 195.5g (1.0mol) of 2-chloro-5-aminotrifluorotoluene into 1L of dichloromethane, cool in an ice-water bath to 0-5°C, add 100.0g (1.0mol) of succinic anhydride in batches, add The reaction was stirred overnight at room temperature, and the reaction of the raw materials was monitored by TLC to complete.

[0040] ②After the reaction is complete, slowly add 400g, 32wt% (3.2mol) of liquid caustic soda to the reaction liquid obtained in step ①, stir at room temperature for 0.5h, let stand to separate layers, remove the organic phase, and add 5.0g, 5wt% % Pd / C catalyst, temperature control 65±1°C, add dropwise 300g aqueous solution containing 82.8g (1.2mol) of hydroxylamine hydrochloride under stirring, drop in about 4 hours, after dropping, control temperature 65±1°C, keep warm for 1h.

[0041] ③After the reaction is complete, add 125g, 32wt% (1.0mol) ...

Embodiment 2～ Embodiment 7）

[0044] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0045] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 solvent Dichloromethane Dichloromethane Dichloromethane Dichloromethane Dichloromethane toluene toluene Dosage of succinic anhydride 1.0mol 1.5mol 1.2mol 1.2mol 1.2mol 1.2mol 1.2mol reducing agent Hydroxylamine hydrochloride Hydroxylamine hydrochloride Hydroxylamine hydrochloride Hydroxylamine hydrochloride formic acid Hydroxylamine hydrochloride formic acid Reductant dosage 1.2mol 1.2mol 1.2mol 1.5mol 1.5mol 1.2mol 1.2mol Yield 115.0g 126.7g 126.1g 127.3g 120.5g 124.7g 117.6g yield 71.9% 79.2% 78.8% 79.6% 75.3% 77.9% 73.5% purity 99.7% 99.9% 99.8% 99.9% 99.7% 99.8% 99.7%

Embodiment 8～ Embodiment 13）

[0047] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 2.

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Abstract

The invention discloses a synthesis method of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl. The method comprises the following steps: subjecting 2-chloro-5-aminobenzotrifluoride serving as a starting raw material and acyclic anhydride in a formula I to amidation to obtain an intermediate II, then carrying out reductive coupling reaction on the intermediate II to obtain an intermediate III, and finally carrying out deamidation reaction on the intermediate III to obtain the 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, wherein the cyclic anhydride in the formula I is succinic anhydride, glutaric anhydride, adipic anhydride or maleic anhydride. The starting material 2-chloro-5-aminobenzotrifluoride is an important farm chemical and medical intermediate, and is low in price, convenient and easy to obtain; the synthesis route is short, the reaction condition is mild, and the method is environment-friendly; the total yield of the synthetic route can reach 60-80%, and compared with the prior art, the synthetic route has obvious advantages and is suitable for industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a synthesis method of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl. Background technique [0002] As an important polymer, polyimide is widely used in aerospace, aviation, microelectronics and other fields because of its excellent physical and chemical properties. [0003] 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl (hereinafter referred to as TFMB) is an important monomer for the synthesis of polyimide, and polyimide synthesized with TFMB as a monomer, Due to the introduction of fluorine atoms, polyimide has excellent comprehensive properties while endowing it with more unique properties, such as thermal stability, chemical inertness, excellent mechanical properties, etc., and has a wide range of applications in materials science and other fields prospect. [0004] At present, there are mainly the following routes for the synthesis of TFMB: [0005] 1....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/15C07C231/12C07C233/43C07C209/50C07C211/52
CPCC07C231/02C07C231/12C07C209/50C07C233/15C07C233/43C07C211/52
Inventor 胡国宜胡锦平吴建华刘伟军
Owner 大连新阳光材料科技有限公司
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