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Surfactant containing o-nitrobenzyl ester photodegradation group, and preparation method thereof

A technology of o-nitrobenzyl ester and surfactant, applied in the field of new light-controlled surface active molecules and its preparation, can solve the problems of low efficiency, long reaction time, cumbersome steps, etc., to improve efficiency and shorten complex reaction process , Improve the effect of reaction selectivity

Inactive Publication Date: 2016-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The carboxyl group of traditional diethylenetriaminepentaacetic acid is generally protected by introducing tert-butyl alcohol into an ester during the synthesis process, but the synthesis process is cumbersome, the reaction time is long, the efficiency is not high, and the selective protection of the carboxyl group is also a difficulty

Method used

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  • Surfactant containing o-nitrobenzyl ester photodegradation group, and preparation method thereof
  • Surfactant containing o-nitrobenzyl ester photodegradation group, and preparation method thereof
  • Surfactant containing o-nitrobenzyl ester photodegradation group, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1 The synthesis of photodegradable surfactant (4-diethylenetriaminepentaacetate)-3-nitro-N,N-dioctylbenzamide:

[0042] (1) Synthesis of diethylene triamine pentaacetic anhydride

[0043] Weigh 3.98g (0.01mol) of diethylenetriaminepentaacetic acid and a 100mL single-necked flask, add 4mL of acetic anhydride and 5mL of pyridine in sequence, raise the temperature to 65°C under nitrogen protection, and react for 24h. Suction filtration after the reaction was completed to obtain a white solid powder. Melting point: 178°C-184°C

[0044] (2) Synthesis of intermediates of N,N-dioctylbenzamide brominated derivatives

[0045]Take 1g (0.004mol) of 4-bromomethyl-3-nitrobenzoic acid in a 100mL three-necked flask, add 10mL of thionyl chloride dropwise under magnetic stirring, and reflux for 3 hours. sulfone. Add 0.96g (0.004mol) di-n-octylamine dropwise to the three-necked flask. After the dropwise addition, add 0.5g (0.004mol) potassium carbonate, react at 40°C for 1...

Embodiment 2

[0052] Example 2 Synthesis of photodegradable surfactant (4-diethylenetriaminepentaacetate)-3-nitro-N,N-didecylbenzamide:

[0053] (1) Synthesis of diethylene triamine pentaacetic anhydride

[0054] Same as Example 1

[0055] (2) Synthesis of N,N-Didecylbenzamide Brominated Derivative Intermediates

[0056] Take 1g (0.004mol) of 4-bromomethyl-3-nitrobenzoic acid and a 100mL three-necked flask, add 10mL of thionyl chloride dropwise under magnetic stirring, and reflux for 4 hours. sulfone. Add 1.19g (0.004mol) di-n-decylamine dropwise to the three-necked flask. After the dropwise addition, add 0.5g (0.004mol) potassium carbonate, react at 50°C for 15h, stop the reaction, add an appropriate amount of deionized water, separate the liquid, and the organic layer Dry it with anhydrous sodium sulfate, and use a 40:1 volume ratio mixture of dichloromethane and methanol as the eluent for column separation to obtain a pale yellow oily liquid. Yield 62.1%.

[0057] (3) Synthesis of (...

Embodiment 3

[0059] Example 3 Synthesis of photodegradable surface active molecule (4-diethylenetriaminepentaacetate)-3-nitro-N,N-behenylbenzamide:

[0060] (1) Synthesis of diethylene triamine pentaacetic anhydride

[0061] Same as Example 1

[0062] (2) Synthesis of intermediates of brominated derivatives

[0063] Take 1g (0.004mol) of 4-bromomethyl-3-nitrobenzoic acid and a 100mL three-necked flask, add 10mL of thionyl chloride dropwise under magnetic stirring, and reflux for 3 hours. sulfone. Add 1.47g (0.004mol) didodecylamine dropwise to the three-necked flask. After the dropwise addition, add 0.5g (0.004mol) potassium carbonate, react at 40°C for 12 hours, stop the reaction, add an appropriate amount of deionized water, separate the liquid, and the organic layer Dry it with anhydrous sodium sulfate, and use a 40:1 volume ratio mixture of dichloromethane and methanol as the eluent for column separation to obtain a pale yellow oily liquid. Yield 46.5%.

[0064] (3) Synthesis of (...

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Abstract

The invention discloses a novel photodegradation surfactant and preparation thereof, belonging to the field of surfactants. The novel photodegradation surfactant is synthesized through the following three reaction steps: (1) with diethylene triamine pentacetic acid as a raw material and acetic anhydride as a dehydrating agent, carrying out dehydration under the catalysis of pyridine so as to produce diethylene triamine pentacetic dianhydride; (2) with an o-nitrobenzyl bromide derivative as a raw material, carrying out acylating chlorination on the derivative and then reacting an acylating chlorination product with secondary amine so as to obtain an intermediate, i.e., para-position double-long-chain carbomite o-nitrobenzyl bromide; and (3) subjecting double-long-chain benzyl bromide in the intermediate and middle carboxyl groups of diethylene triamine pentacetic dianhydride to nucleophilic substitution under the catalysis of a catalyst in a solvent so as to obtain surfactant molecules containing o-nitrobenzyl ester light-operated groups. According to the invention, four terminal carboxyl groups are protected by ingeniously utilization of dehydration of diethylene triamine pentacetic acid into anhydride, the middle carboxyl groups are selectively utilized and form ester under the catalysis of organic base DBU, so the o-nitrobenzyl ester photodegradation surfactant is prepared. Compared with traditional methods, the method provided by the invention has the advantages that reaction flow is shortened and efficiency is greatly improved.

Description

technical field [0001] The invention relates to a novel light-controlling surface active molecule and a preparation method thereof, in particular to using o-nitrobenzyl ester as a photodegradation group, using secondary amine double long chains as a hydrophobic group, and diethylenetriaminepentaacetic acid as a hydrophilic A new surface-active molecule of a group and a new synthesis method thereof belong to the field of surfactants. Background technique [0002] Environment-responsive amphiphilic molecular assemblies have attracted much attention for their potential applications in the controlled release of drugs, while light-responsiveness is controllable in vitro and does not require specific chemical changes in vivo. The drug is wrapped in the carrier, injected intravenously into the blood circulation, and stimulated by ultraviolet or near-infrared light outside the body to realize the controlled release of the drug, thereby effectively reducing the loss of the drug and i...

Claims

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Application Information

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IPC IPC(8): B01F17/28B01F17/22C07C235/42C07C231/12C09K23/28C09K23/22
CPCC07C231/12C07C235/42C09K23/00
Inventor 乔卫红李泉刘宸宇
Owner DALIAN UNIV OF TECH
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