Method for synthesizing 1-naphthylamine-4-sodium sulfonate by gas-phase SO3 sulfonation method

A technology of sodium sulfonate and naphthylamine, applied in the preparation of sulfonate, organic chemistry, etc., can solve the problems of limiting the production of 1-naphthylamine-4-sodium sulfonate, increasing labor and economic costs, and increasing the burden of environmental governance , achieve the effect of shortening the reaction time, reducing energy consumption and speed

Inactive Publication Date: 2016-12-21
CHINA RES INST OF DAILY CHEM IND
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AI Technical Summary

Problems solved by technology

Although the research group completed the synthesis of 1-naphthylamine-4-sodium sulfonate under normal pressure, the sulfonating agent used in this method is concentrated sulfuric acid. Finally, it needs to be dehydrated at a high temperature of 180-190°C to generate naphthalene aminosulfonic acid, and then baked at a high temperature (180-190°C) to perform intramolecular rearrangement to generate 1-naphthylamine-4-sulfonic acid, so the overall reaction time is relatively short long, high heat energy consumption, high production cost and low efficiency; at the same time, a large amount of acidic wastewater produced after high-temperature dehydration increases the burden on environmental governance, increases labor and economic costs, and limits the use of 1-naphthylamine-4-sodium sulfonate Production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Gas SO 3 Mix with dry air with a dew point below -50°C and cool to 40°C to form SO 3 Accounting for the mixed gas whose volume ratio is 10%, the mixed gas is passed into the reactor equipped with raw material 1-naphthylamine (3.75Kg) and o-dichlorobenzene (14L), wherein nSO 3 / n1-naphthylamine=1.0:1, react at 90°C for 40 minutes for sulfonation into salt, after the sulfonation reaction, stop feeding SO 3 Mixed gas with air; then, raise the temperature of the reactor to 180°C for 60 minutes, then slowly add water (11L) into the reactor, and when the temperature drops to 80°C, add solid sodium carbonate (1.6Kg) to make the mixture Neutralize until the pH value is 8, and after standing to separate layers, the oil phase and the water phase are obtained; the water phase is concentrated until the specific gravity of the concentrated solution is 1.20, and the obtained concentrated solution is separated at 60°C for 2 hours to obtain product 1 - Sodium naphthylamine-4-sulfonat...

Embodiment 2

[0024] Gas SO 3 Mix with dry air with a dew point below -50°C and cool to 45°C to form SO 3 The volume ratio of the mixed gas is 7%, and the mixed gas is passed into the reaction kettle equipped with raw materials 1-naphthylamine (3.75Kg), o-dichlorobenzene (9L) and durene (5L), where n SO 3 / n1-naphthylamine=1.4:1, react at 40°C for 50 minutes for sulfonation into salt, after the sulfonation reaction, stop feeding SO 3 Mixed gas with air; then, raise the temperature of the reactor to 190°C for 180 minutes, slowly add water (11L) to the reactor, and add solid sodium hydroxide (1.13Kg) when the temperature drops to 85°C to make The mixture was neutralized until the pH value was 7, and the oil phase and the water phase were obtained after standing for separation; the water phase was concentrated until the specific gravity of the concentrated solution was 1.21, and the obtained concentrated solution was separated at 65°C for 1 hour to obtain the product Sodium 1-naphthylamine-...

Embodiment 3

[0026] Gas SO 3 Mix with dry air with a dew point below -50°C and cool to 50°C to form SO 3 The mixed gas with a volume ratio of 6% of the mixed gas is passed into the reaction kettle filled with raw materials 1-naphthylamine (3.75Kg) and mesitylene (10L), where nSO 3 / n1-naphthylamine=2.0:1, react at 60°C for 70 minutes for sulfonation into salt, after the sulfonation reaction, stop feeding SO 3 Mixed gas with air; then, raise the temperature of the reactor to 180°C for 120 minutes, slowly add water (11L) to the reactor, and when the temperature drops to 90°C, add solid potassium carbonate (1.63Kg) to make the mixture Neutralize until the pH value is 9, and after standing to separate layers, the oil phase and the water phase are obtained; the water phase is concentrated until the specific gravity of the concentrated solution is 1.22, and the obtained concentrated solution is separated at 70°C for 1.5 hours to obtain the product Sodium 1-naphthylamine-4-sulfonate. The mass ...

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Abstract

The invention relates to a method for synthesizing 1-naphthylamine-4-sodium sulfonate by a gas-phase SO3 sulfonation method. The method is characterized in that gas SO3 and dry air are mixed and cooled, a mixture is introduced into a reaction vessel filled with 1-naphthylamine and an organic solvent for sulfonation, the reaction vessel is heated to the temperature of 160-190 DEG C for transposition, water and solid alkali are slowly added in the reaction vessel for neutralizing until the pH value is 7-9, and the material is subjected to standing and layering to obtain an oil phase and a water phase; the water phase is concentrated until the concentrate proportion is 1.20-1.22, the obtained concentrate is subjected to standing for 1-2 hours at the temperature of 60-80 DEG C, and then the material is separated to obtain the product 1-naphthylamine-4-sodium sulfonate. The method has the advantages of short reaction time, low energy consumption, high efficiency during the reaction process, and no three-waste generation.

Description

technical field [0001] The present invention relates to a kind of gas phase SO 3 A method for synthesizing 1-naphthylamine-4-sodium sulfonate by sulfonation method. Background technique [0002] 1-naphthylamine-4-sodium sulfonate is an important dyestuff, chemical and pharmaceutical intermediate. In the dye industry, it is an important intermediate for the production of environmentally friendly dyes, and is widely used in the synthesis of nivenic acid, direct and reactive dyes. In the chemical industry, it is often used in the synthesis of macromolecules. At the same time, because the amino group and sulfonic acid group of 1-naphthylamine-4-sulfonate sodium can be well coordinated with the supply atom, 1-naphthylamine-4-sulfonate Sodium sulfonate can be used as both a hydrogen bond donor and a hydrogen bond acceptor, making 1-naphthylamine-4-sodium sulfonate widely used in complexing with various metals (such as Fe, Zn, Cd, Ni, etc.) It is used for the synthesis of toxic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/32C07C309/47
CPCC07C303/32C07C309/47
Inventor 李萍杨效益郭朝华李全红李建波卢建强李慧芳耿卫东杨晓东岑世明
Owner CHINA RES INST OF DAILY CHEM IND
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