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Novel composite quaternary phosphonium salt and its preparation method and antibacterial application

A quaternary phosphonium salt and a new technology, applied in the field of fine chemical synthesis, can solve the problems of short duration of inhibitory action, unsatisfactory effect, poor stability, etc., and achieve the effects of low synthesis price, low raw material consumption and good stability

Active Publication Date: 2017-06-06
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the existing quaternary phosphonium salt fungicides have the advantages of fast antibacterial action, wide antibacterial spectrum, and good anti-mildew effect, they still have certain defects, such as poor stability, unsatisfactory effect, and short duration of inhibitory action.

Method used

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  • Novel composite quaternary phosphonium salt and its preparation method and antibacterial application
  • Novel composite quaternary phosphonium salt and its preparation method and antibacterial application
  • Novel composite quaternary phosphonium salt and its preparation method and antibacterial application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A compound quaternary phosphonium salt A in a single crystal form has the molecular structure shown in the above general formula, wherein R is Cl.

[0028] Its preparation method is as follows:

[0029] (1) Dissolve 2 mmol of 2-chlorobenzyl bromide and 1.6 mmol of triphenylphosphine in 20 mL of acetone, stir and reflux at 65-70 ºC for 24 hours, during which a white precipitate is formed, and after natural cooling, suction filter, and separate Wash the filter cake with a small amount of acetone and ether to remove impurities and accelerate drying, and then vacuum-dry to obtain 2-chlorobenzyltriphenylphosphine bromide with a yield of 79.3%; infrared spectroscopic analysis: IR (cm -1 ): ν(benzene ring C–H): 3053; ν(CH 2 ): 2925, 2884; ν(C=C): 1587, 1432; ν(C–P): 1111;

[0030] (2) 1 mmol of the obtained 2-chlorobenzyltriphenylphosphine bromide and CuCl 2 2H 2 O 0.45 mmol was dissolved in methanol 15mL, then added 0.5mL hydrochloric acid, continued to stir, while heatin...

Embodiment 2

[0038] A compound quaternary phosphonium salt B in a single crystal form has the molecular structure shown in the above general formula, wherein R is Br.

[0039] Its preparation method is as follows:

[0040] (1) Dissolve 2 mmol of 2-bromobenzyl bromide and 2 mmol of triphenylphosphine in 30 mL of acetone, stir and reflux at 65-70 ºC for 20 hours, during which a white precipitate is formed, and after natural cooling, suction filter, and separate Wash the filter cake with a small amount of acetone and ether to remove impurities and accelerate drying, and then vacuum-dry to obtain 2-bromobenzyltriphenylphosphine bromide with a yield of 86.4%; infrared spectroscopic analysis: IR (cm -1 ): ν(benzene ring C–H): 3053; ν(CH 3 ): 2922, 2884; ν(C=C): 1584, 1432; ν(C–P): 1114;

[0041] (2) 1 mmol of the obtained 2-bromobenzyltriphenylphosphine bromide and CuCl 2 2H 2 O 0.5 mmol was dissolved in 20 mL of methanol, then 1 mL of hydrochloric acid was added, stirring continuously, whil...

Embodiment 3

[0043] A compound quaternary phosphonium salt C in a single crystal form has the molecular structure shown in the above general formula, wherein R is NO 2 .

[0044] Its preparation method is as follows:

[0045](1) Dissolve 2 mmol of 2-nitrobenzyl bromide and 2.4 mmol of triphenylphosphine in 40 mL of acetone, stir and reflux at 65-70 ºC for 16 hours, during which a white precipitate is formed, and after natural cooling, suction filter, and separate Wash the filter cake with a small amount of acetone and ether to remove impurities and accelerate drying, and then vacuum-dry to obtain 2-nitrobenzyltriphenylphosphine bromide with a yield of 88.6%; infrared spectroscopic analysis: IR (cm -1 ):ν(NH 2 ): 3341; ν(benzene ring C–H): 3050; ν(CH 2 ): 2922, 2875; ν(C=C): 1581, 1432; ν(NO 2 ): 1530, 1335; ν(C–P): 1105.

[0046] (2) 1 mmol of the obtained 2-nitrobenzyltriphenylphosphine bromide and CuCl 2 2H 2 Dissolve O 0.56 mmol in 25 mL of methanol, add 1.5 mL of hydrochloric ac...

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Abstract

The invention belongs to the technical field of fine chemical synthesis and particularly relates to a novel composite phosphonium salt as well as a preparation method and an antibacterial application thereof. The novel composite phosphonium salt adopts a molecular structure shown in the general formula represented in the specification, wherein R is selected from one of Cl, Br and NO2 groups. The novel composite phosphonium salt has good stability, excellent antibacterial performance and long bacteriostasis duration; the preparation method comprises steps of synthesis of brominated substituted benzyl triphenylphosphine, synthesis of an antibacterial complex, crystallization and the like, the operation is simple and controllable, large-scale instruments and equipment are not required, and the production cost is reduced remarkably.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to a novel composite quaternary phosphonium salt, a preparation method thereof and an antibacterial application. Background technique [0002] Antibacterial agents refer to various preparations that can kill or inhibit the activity of microorganisms within a certain period of time. They are chemical substances that are highly sensitive to microorganisms such as bacteria and molds. Antimicrobial agents have a wide range of uses, are closely related to human life, and are widely used in industry, agriculture, and animal and plant protection. The quaternary phosphonium salt was discovered in the early 1990s as a water treatment agent. In 1990, Gramham pointed out that the quaternary phosphonium salt was used for industrial and oil field water treatment with high efficiency, fast, broad spectrum, and low environmental and fish effects. It has the advantages ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/54A01N57/22A01N59/20A01P3/00A01P1/00
Inventor 倪春林周家容叶辉青张正胡甜刘茵满丽敏
Owner SOUTH CHINA AGRI UNIV
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