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Preparation of carboxylazocalix [4] arene derivatives

A technology for benzeneazo calix and arene derivatives, which is applied in the field of preparation of calixarene derivatives, can solve the problems of pyridine inflammability, toxic odor, malodor and the like, and achieves the advantages of avoiding odor and toxicity, mild reaction conditions and simple operation. Effect

Inactive Publication Date: 2009-01-21
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, the initiator pyridine used in the above preparation method is flammable, toxic and has a bad smell

Method used

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  • Preparation of carboxylazocalix [4] arene derivatives
  • Preparation of carboxylazocalix [4] arene derivatives
  • Preparation of carboxylazocalix [4] arene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Since aniline will deteriorate after being left for a period of time, the aniline in this example must be obtained by nitrogen protection distillation after drying with molecular sieves.

[0035] Sodium nitrite 0.69g (10mmol) was dissolved in 5mL of water, then slowly added dropwise under stirring to the concentrated hydrochloric acid containing 0.91mL (10mmol) freshly distilled aniline: water=3:7 (volume ratio, wherein the concentrated hydrochloric acid was 3 mL) solution, keep the temperature at 0-5°C, and stir for another 30 minutes after the dropwise addition is completed.

[0036] Since azo salts are unstable at room temperature, and the preparation of azo salts is an exothermic reaction, the reaction temperature should always be kept at 0-5°C.

[0037] Then the above-mentioned azo salt solution was slowly added dropwise to a mixture of 26 mL N, N'-dimethylformamide and methanol mixed with 1 g (2.36 mmol) calix [4] arene and 4.08 g (30 mmol) sodium acetate In the ...

Embodiment 2

[0041] Since aniline will deteriorate after being left for a period of time, the aniline in this example must be obtained by nitrogen protection distillation after drying with molecular sieves.

[0042] Sodium nitrite 0.69g (10mmol) was dissolved in 5mL of water, then slowly added dropwise under stirring to the concentrated hydrochloric acid containing 0.91mL (10mmol) freshly distilled aniline: water=3:7 (volume ratio, wherein the concentrated hydrochloric acid was 3 mL) solution, keep the temperature at 0-5°C, and stir for another 30 minutes after the dropwise addition is completed.

[0043] Since azo salts are unstable at room temperature, and the preparation of azo salts is an exothermic reaction, the reaction temperature should always be kept at 0-5°C.

[0044] Then the above-mentioned azo salt solution was slowly added dropwise to a mixture of 26 mL N, N'-dimethylformamide and methanol mixed with 1 g (2.36 mmol) calix [4] arene and 4.08 g (30 mmol) sodium acetate In the ...

Embodiment 3

[0048] Since aniline will deteriorate after being left for a period of time, the aniline in this example must be obtained by nitrogen protection distillation after drying with molecular sieves.

[0049] Sodium nitrite 0.69g (10mmol) was dissolved in 5mL of water, then slowly added dropwise under stirring to the concentrated hydrochloric acid containing 0.91mL (10mmol) freshly distilled aniline: water=3:7 (volume ratio, wherein the concentrated hydrochloric acid was 3 mL) solution, keep the temperature at 0-5°C, and stir for another 30 minutes after the dropwise addition is completed.

[0050] Since azo salts are unstable at room temperature, and the preparation of azo salts is an exothermic reaction, the reaction temperature should always be kept at 0-5°C.

[0051] Then the above-mentioned azo salt solution was slowly added dropwise to a mixture of 26 mL N, N'-dimethylformamide and methanol mixed with 1 g (2.36 mmol) calix [4] arene and 4.08 g (30 mmol) sodium acetate In the ...

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Abstract

The invention discloses a preparation method for a phenylazocalix [4] arene derivative. The preparation method comprises the following steps that azobenzene chloride and calix [4] arene are taken as reactants, a mixed solution of N, N'-dimethyl formamide and methanol as solvent and sodium acetate as an initiator so as to prepare the phenylazocalix [4] arene derivative; and products include 5-azobenzol-25, 26, 27, 28-tetrahydroxycalix [4] arene, 5, 11-biazobenzol-25, 26, 27, 28-tetrahydroxycalix [4] arene, 5, 11, 17-triazobenzol-25, 26, 27, 28-tetrahydroxycalix [4] arene and 5, 11, 17, 23-tetraazobenzol-25, 26, 27, 28-tetrahydroxycalix [4] arene. Moreover, because the adopted initiator is sodium acetate, the preparation method does not adopt pyridine with heavier smell and more toxicity; moreover, the method can adjust the relative proportion of four reactants through controlling reaction time.

Description

technical field [0001] The invention relates to a preparation method of calixarene derivatives, in particular to a preparation method of phenylazocalix[4]arene derivatives. Background technique [0002] Calixarenes are cyclic oligomers, which are cyclic oligomers connected by phenol units through methylene groups. They have the characteristics of adjustable cavity, changeable conformation, and easy chemical modification and modification. [0003] Appropriate functional groups can be introduced into the upper and lower edges of calixarene through chemical reactions, so that the chemically modified calixarene as the host molecule has potential and great application prospects in recognizing organic molecules and transporting cations. Functional groups of calixarenes can be introduced into both the upper edge and the lower edge. The modification of the upper edge of calixarene is usually to remove the tert-butyl group first and then carry out the derivatization reaction. It is ...

Claims

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Application Information

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IPC IPC(8): C07C245/10
Inventor 郎建平刘雷雷陈阳唐晓艳李红喜
Owner SUZHOU UNIV