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Ionic liquid functionalized acid orange for organic solvent and preparation method thereof

A technology of ionic liquid and organic solvent, which is applied in the field of ionic liquid functionalized acid orange dye and acid-base indicator and its preparation, achieving the effect of mild reaction conditions and simple synthesis method

Pending Publication Date: 2019-07-12
ZAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since Acid Orange is easily soluble in water and difficult to dissolve in non-polar and weakly polar organic solvents, it can only be used as a traditional aqueous phase dyeing and acid-base indicator, and cannot be used in non-polar and weakly polar organic solvents.

Method used

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  • Ionic liquid functionalized acid orange for organic solvent and preparation method thereof
  • Ionic liquid functionalized acid orange for organic solvent and preparation method thereof
  • Ionic liquid functionalized acid orange for organic solvent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of ethyltriphenylphosphonium bromide:

[0033] Add 1.31 g (5.0 mmol) of triphenylphosphine and 20 mL of dry benzene into a 100 mL three-necked flask, stir and dissolve at room temperature. Then, 0.60 g (5.5 mmol) of 1-bromoethane was slowly added dropwise with stirring. After the addition was completed, the mixture was stirred and reacted at 40°C for 48 hours. After the reaction, cool to room temperature, filter with suction, and wash repeatedly 3 times to obtain a white solid, which is vacuum-dried to obtain 1.82 g of bromobutyltriphenylphosphonium as a white powder solid, with a yield of 89.2%.

[0034] 1 H NMR (400MHz, DMSO-d6) (ppm): δ=7.75-7.93 (m, 15H, H on the benzene ring), 3.34-3.66 (t, 2H, H on the methylene connected to P), 1.17-1.27 (t, 3H, H on methyl in ethyl).

[0035] Synthesis of acid orange silver salt:

[0036] Under nitrogen protection, 0.84 g (2.4 mmol) of Acid Orange II was dissolved in a small amount of deionized water, acidified by...

Embodiment 2

[0042] Synthesis of butyltriphenylphosphonium bromide:

[0043] Add 1.31 g (5.0 mmol) of triphenylphosphine and 20 mL of dry toluene into a 100 mL three-necked flask, stir and dissolve at room temperature. Then, 0.69 g (5.0 mmol) of 1-bromobutane was slowly added dropwise with stirring. After the addition was complete, the mixture was stirred and reacted at 100°C for 48 hours. After the reaction, cool to room temperature, filter with suction, and wash repeatedly 3 times to obtain a white solid, which is vacuum-dried to obtain 1.85 g of bromobutyltriphenylphosphonium as a white powder solid, with a yield of 92.5%.

[0044] 1 H NMR (400MHz, DMSO-d6) (ppm): δ=7.75-7.92 (m, 15H, H on the benzene ring), 3.34-3.62 (t, 2H, H on the methylene connected to P), 1.45-1.52 (m, 4H, the H on the methylene in the butyl group except the methylene directly connected to P), 0.87-0.91 (t, 3H, the H on the methyl group in the butyl group).

[0045] Synthesis of acid orange silver salt:

[00...

Embodiment 3

[0052] Synthesis of dodecyltriphenylphosphonium bromide:

[0053] Add 1.31g (5.0mmol) of triphenylphosphine and 20mL of dry xylene into a 100mL three-necked flask, stir and dissolve at room temperature. Then, 1.38 g (5.5 mmol) of 1-bromododecane was slowly added dropwise while stirring. After the addition, the mixture was stirred and reacted at 120°C for 48 hours. After the reaction was completed, it was cooled to room temperature to obtain a viscous solid mixture. Add an appropriate amount of ethyl acetate and heat to 70°C, stir and wash thoroughly, then suction filter while it is hot, and repeat the washing 3 times to obtain a white solid, which is dried in vacuo to obtain 2.46 g of dodecyltriphenylphosphonium bromide as a white powder solid, with a yield of 96.1%.

[0054] 1 H NMR (400MHz, DMSO-d6) (ppm): δ=7.75-7.93 (m, 15H, H on the benzene ring), 3.54-3.62 (t, 2H, H on the methylene connected to P), 1.22 -2.51 (m, 20H, H on other methylene groups except the methylen...

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Abstract

The invention relates to ionic liquid functionalized acid orange for an organic solvent and a preparation method thereof. The preparation method for the ionic liquid functionalized acid orange for theorganic solvent provided by the invention comprises the following steps: first, first, reacting triphenylphosphine and slightly excessive bromoalkane, and washing and purifying by using ethyl acetateto prepare alkyl triphenyl bromide; performing neutral reaction on acidified acid orange and silver carbonate, and washing and drying to prepare acid orange silver salt; then, respectively performingion exchange on the prepared acid orange silver salt and different alkyl triphenyl bromide to prepare a series of novel ionic liquid functionalized acid orange which can be dissolved in a plurality of organic solvents. The synthesis reaction conditions are mild and the post-treatment is simple. The type of ionic liquid functionalized acid orange has good solubility in the plurality of the organicsolvents, and is an azo dye and an acid base indicator which can be used for the organic solvent.

Description

technical field [0001] The invention belongs to the field of chemical material preparation, and in particular relates to an ionic liquid functionalized acid orange dye and an acid-base indicator soluble in various organic solvents and a preparation method thereof. Background technique [0002] Acid orange, also known as Orange II, chemically named 2-naphthol azo-p-benzenesulfonate sodium, is an acidic azo industrial dye. Because of its bright color and good level dyeing property, it is mainly used for industrial dyeing and can also be used Used as acid-base indicator and biological stain. Since Acid Orange is easily soluble in water and hardly soluble in non-polar and weakly polar organic solvents, it can only be used as a traditional aqueous phase dyeing and acid-base indicator, and cannot be used in non-polar and weakly polar organic solvents. . [0003] Room temperature ionic liquids (Ionic Liquids, ILs), as a new medium and soft functional material developed under the ...

Claims

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Application Information

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IPC IPC(8): C07F9/54C07C309/46C07C303/32
CPCC07F9/5442C07C309/46C07C303/32
Inventor 周峰岩边静雯马杰王天琪孙轶男熊英硕汪勇臣
Owner ZAOZHUANG UNIV
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