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A kind of microwave atmospheric pressure synthetic method of naphthalimide quaternary ammonium salt

A naphthalimide, atmospheric synthesis technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of poor water solubility of naphthalimide, limited application range, long reaction time, etc. Purification, no secondary pollution, less solvent consumption

Inactive Publication Date: 2015-09-30
CNOOC TIANJIN CHEM RES & DESIGN INST +2
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, most of the naphthalimides reported in the literature have poor water solubility, and the scope of application is limited. Necessary chemical modifications can improve their water solubility
At present, there are mainly two modification approaches reported: introducing hydrophilic groups such as sulfonic acid groups on the naphthalene ring parent, or introducing a quaternary ammonium salt structure into the side chain of the naphthalene ring (Zhang Yuehua, Zhang Qiping, Lei Wu et al. 1 , Synthesis, characterization and fluorescence properties of 8-naphthalimide fluorescent monomer[J]. Fine Petrochemical Industry, 2008, 25(5): 60-6; ​​Zhang Qiping, Zhang Yuehua, Huang Dan, etc. Water-soluble 1,8 -Synthesis and characterization of naphthalimide-based fluorescent monomers[J]. Chemical Reagents, 2007, 29(2): 78-80), in contrast, the latter reaction conditions are relatively simple, but there is still a long reaction time , cumbersome operation and other disadvantages

Method used

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  • A kind of microwave atmospheric pressure synthetic method of naphthalimide quaternary ammonium salt
  • A kind of microwave atmospheric pressure synthetic method of naphthalimide quaternary ammonium salt
  • A kind of microwave atmospheric pressure synthetic method of naphthalimide quaternary ammonium salt

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Effect test

Embodiment 1

[0028] (1) Synthesis of Compound II: 0.01mol 4-bromo-1,8-naphthalene anhydride, 0.03mol N-methylpiperazine and 10mL ethylene glycol monomethyl ether were added in turn to a 100mL flask, placed in a microwave reactor, 530W Microwave pulse radiation reaction under high power, pulse width is 65s, duty ratio is 12:1, radiation reaction is 65min, and the end point of the reaction is monitored by TLC method (developing agent: dichloromethane: methanol: triethylamine=18:8:0.5) , until R f The raw material point of 0.54 disappears. Add 40 mL of glacial acetic acid to the mixture, freeze to crystallize, filter after thawing, collect the solid, wash with 20 mL of absolute ethanol 2 to 3 times, and dry the solid under vacuum at 40°C / -0.1Mpa to obtain a dark yellow solid with a yield of 97.6%.

[0029] IR (KBr, ν / cm -1 ): 1465.26, 1399.37 (-CH 3 Deformation vibration); 1339.99, 1350.91 (C-N stretching vibration), 2687.92, 2607.71 (multiple frequency of C-N stretching); at the same time...

Embodiment 2

[0047] (1) Synthesis of Compound II: The reaction conditions are the same as step (1) in Example 1, except that the pulsed radiation power is 450W, the radiation reaction time is 70min, and the post-treatment method is the same as step (1) in Example 1. , a dark yellow solid was obtained with a yield of 92.5%.

[0048] (2) Synthesis of Compound III: The reaction conditions are the same as step (2) in Example 1, except that the lower alcohol is methanol, the pulsed radiation power is 250W, and the post-treatment method is the same as step (2) in Example 1. A yellow-green solid was obtained with a yield of 75.7%.

[0049] (3) Synthesis of compound IV-1: the reaction conditions are the same as step (3) in Example 1, the difference is that the pulsed radiation power is 450W, and the post-treatment method is the same as step (3) in Example 1 to obtain bright yellow Solid, 98.3% yield.

Embodiment 3

[0051] (1) Synthesis of Compound II: The reaction conditions are the same as step (1) in Example 1, except that the pulsed radiation power is 600W, the radiation reaction time is 55min, and the post-treatment method is the same as step (1) in Example 1. , a dark yellow solid was obtained with a yield of 93.3%.

[0052] (2) Synthesis of Compound III: The reaction conditions are the same as step (2) in Example 1, except that the pulsed radiation power is 530W, the radiation reaction time is 12min, and the post-treatment method is the same as step (2) in Example 1. , to obtain a yellow-green solid with a yield of 76.4%.

[0053] (3) Synthesis of compound IV-1: The reaction conditions are the same as step (3) in Example 1, except that the molar ratio of raw materials is 1:2 (compound III: 0.005mol, 1-bromobutane: 0.010 mol), the post-treatment method was the same as step (3) in Example 1 to obtain a bright yellow solid with a yield of 80.8%.

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Abstract

The invention discloses a microwave atmospheric pressure synthesis method for a naphthalene imide quaternary ammonium salt. The method is characterized by comprising the following step: by taking 4-Br-1,8-anhydride naphthalene as a raw material, reacting by three steps of amination, amidation and side-chain quaternization by adopting a microwave atmospheric pressure synthesis method, so as to obtain the water-soluble naphthalene imide quaternary ammonium salt. A solvent selected in each step is a polar molecule, microwave radiation is applied in a pulse mode, proper radiation power, pulse width and duty ratio are controlled, and the heat effect and non-heat effect of the microwave are reasonably utilized. The method disclosed by the invention has the advantages that a lot of solvents are not needed, operation is simple, the reaction rate of each step is improved by over 10 times in comparison with that of a conventional method, and the defects of the prior art that reaction time is long, operation is fussy, pollution to environment is caused by a lot of solvents, and the like are solved. Meanwhile, the product is easy to purify, and the productive rate of each step is improved. Therefore, the synthesis method provided by the invention is an efficient, energy-saving, green and environment-friendly synthesis method.

Description

technical field [0001] The invention belongs to the field of preparation of naphthalimide fluorescent compounds, in particular to a microwave normal-pressure synthesis method of a naphthalimide quaternary ammonium salt. Background technique [0002] Naphthalimide fluorescent compounds have a very planar naphthalene ring structure, and there is a large "absorbing-donating electron conjugated system" in the molecular structure, which makes them have higher fluorescence intensity and quantum yield. These compounds have been extensively studied for their unique properties. This type of fluorescent compound has bright color and strong fluorescence, and has been widely used as fluorescent dyes and fluorescent whitening agents. Studies in recent years have shown that this type of compound is often used as photosensitive materials, liquid crystal materials, lasers, fluorescent probes, DNA intercalators and other fields. [0003] However, most of the naphthalimides reported in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06
CPCC07D221/14
Inventor 金秀红孙冬雪沈晓莉焦志增
Owner CNOOC TIANJIN CHEM RES & DESIGN INST
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