A kind of method that transfer hydrogenation method prepares aminonaphthol sulfonic acid

A technology for aminonaphtholsulfonic acid and nitronaphtholsulfonic acid is applied in the field of preparing aminonaphtholsulfonic acid by transfer hydrogenation, which can solve the problems of corrosion equipment process operation, harsh preparation conditions, pollution of the environment and the like, and avoid pollution problems. , The effect of good product quality and easy process operation

Active Publication Date: 2019-09-10
TIANLING NEW MATERIAL XIAMEN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the problems of corrosion equipment, complicated process operation, and environmental pollution caused by a large amount of waste residues in the existing hydrosulfite reduction process, as well as the need to use special equipment and harsh preparation conditions when catalytic hydrogenation is used, the purpose of the present invention is to provide A method for preparing aminonaphthol sulfonic acid by transfer hydrogenation, the method is to prepare aminonaphthol sulfonic acid by using the green reduction process of transfer hydrogenation reduction under the action of a catalyst, wherein the nitroso or nitro group is in the naphthol structure The position in is 2 or 4, and the position of the sulfonic acid group in naphthol is 5 or 4

Method used

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  • A kind of method that transfer hydrogenation method prepares aminonaphthol sulfonic acid

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Embodiment 1

[0045] First add 25.3g (0.1mol) 1-naphthol-2-nitroso-5-sulfonic acid in the reaction vessel, then add 50% of 1-naphthol-2-nitroso-5-sulfonic acid weight Ethanol, add 80% hydrazine hydrate 9.0g (0.144mol), then add 5% Raney nickel catalyst of 1-naphthol-2-nitroso-5-sulfonic acid weight, stir at room temperature, control the reaction temperature 30 ℃ , Stirring and reacting for 3 hours, the conversion rate of raw materials reaches above 98.0%. The catalyst was filtered out at room temperature to obtain a solution of the product, which was concentrated and acidified to obtain the product.

[0046] figure 1 It is the HPLC collection of illustrative plates of the product of this embodiment, and the HPLC detection condition is: instrument parameter: Agilent high performance liquid chromatograph 1100, diode array detector, chromatographic column: C18 46 * 250mm, 5 μ m, mobile phase: V methanol: V water: V acetic acid :V triethylamine=14:85.1:0.6:0.3, flow rate: 1mL / min, detection w...

Embodiment 2

[0049] First add 25.3g (0.1mol) 1-naphthol-2-nitroso-5-sulfonic acid in the autoclave, add 9.0g (0.144mol) of 80% hydrazine hydrate, then add 1-naphthol-2-sulfonic acid 5 times the ethanol of nitro-5-sulfonic acid weight, then add 5% Pt / C catalyst of 1-naphthol-2-nitroso-5-sulfonic acid weight, stir evenly at room temperature, control reaction temperature 20 ℃ , Stirring and reacting for 3 hours, the conversion rate of raw materials reached above 98.2%. The catalyst was filtered out at room temperature to obtain a solution of the product, which was concentrated and acidified to obtain the product.

[0050] Liquid phase analysis showed that the product content was 98.6%, and the yield was 85%.

Embodiment 3

[0052] First add 25.3g (0.1mol) 1-naphthol-2-nitroso-5-sulfonic acid in the autoclave, add 6.26g (0.1mol) of 80% hydrazine hydrate, then add 1-naphthol-2-nitroso nitro-5-sulfonic acid 2 times the weight of ethanol, then add 1-naphthol-2-nitroso-5-sulfonic acid 5% Pd / C catalyst, stir evenly at room temperature, control the reaction temperature 40 ℃ , Stirring and reacting for 4 hours, the conversion rate of raw materials reached above 98.4%. The catalyst was filtered out at room temperature to obtain a solution of the product, which was concentrated and acidified to obtain the product.

[0053] Liquid phase analysis showed that the product content was 98.2%, and the yield was 80%.

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Abstract

The invention provides a method for preparing amino-naphthol sulfonic acid with a transfer hydrogenation method. The method is used for preparing amino-naphthol sulfonic acid by performing transfer hydrogenation reduction on nitroso or nitro-naphthol sulfonic acid and comprises the following steps: S110: sequentially adding the nitroso or nitro-naphthol sulfonic acid, an inert solvent, a catalyst and a hydrogen source in a reaction vessel, and performing transfer hydrogenation reduction at the temperature ranging from 20 DEG C below zero to 120 DEG C, wherein the hydrogenation reaction time is 0.5-10h; and S120: after reaction is complete, performing solid-liquid separation, and after concentrating separated liquid, performing acidification and product separation to acquire the required amino-naphthol sulfonic acid. By adopting a process for preparing the amino-naphthol sulfonic acid with the transfer hydrogenation method, operation is simple and convenient; the quality of a product is good; and a product is obtained by filtering and separating the catalyst after the reaction is finished, the catalyst and the solvent can be recycled after being simply treated, so that the pollution problem is solved, and the process is an environment-friendly green production process.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing aminonaphtholsulfonic acid by transfer hydrogenation. Background technique [0002] 2-Amino-1-naphthol-5-sulfonic acid and 2-amino-1-naphthol-4-sulfonic acid are preparations of 2-diazo-1-naphthoquinone-5-sulfonyl chloride and 2-diazo-1 -Intermediate of naphthoquinone-4-sulfonyl chloride. 2-diazo-1-naphthoquinone-5-sulfonyl chloride and 2-diazo-1-naphthoquinone-4-sulfonyl chloride are mainly used for photosensitive coating of pre-coated photosensitive lithography (referred to as PS plate), integrated circuits, printing The photoresist of the circuit is also developed abroad for home appliances, tinplate products, precision mechanical drawing, color TV, photocopying, photosensitive re-inking, etc. [0003] In the prior art, 2-amino-1-naphthol-5-sulfonic acid and 2-amino-1-naphthol-4-sulfonic acid are prepared by using hydrochloric acid and hydroc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/50C07C303/22
Inventor 费国辉赵宏赵世龙
Owner TIANLING NEW MATERIAL XIAMEN
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