Synthetic method of 2,5-diaminotoluene and sulphate thereof

A technology of diaminotoluene and aminoazotoluene, which is applied in 2 fields, can solve the problems of poor economy, utilization of o-toluidine, and difficulty in industrialization implementation, and achieve the effect of reducing unit consumption and reducing pollution

Active Publication Date: 2009-06-10
宁夏瑞鼎科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology uses certain chemicals called naphthoquinone (CN) or benzidene carboxylic acid (BCA), together with other substances like ammonia nitrobenzenesulfonic acid (ANS). These intermediates are used for making new drugs that have improved properties such as reduced side effectiveness over older ones due to their lowered metabolic rate compared to newer molecules. By combining these chemistry techniques with different methods, this method allows us to create more effective medications by producing them efficiently while minimizing environmental impact.

Problems solved by technology

This patented technical issue addressed in this patents relating to reducing greenhouse gas emissions from chemical industry involves developing a commercially feasible approach towards producing 2,25-tetramarboxalmitranosum triphosphorus trisodium phytophthaleplianalite (TPA-32) without generating excessively expensive processes like hexane dichlorodiodecylamination. Additionally, finding ways to efficiently convert certain types of starting material into desired forms while minimizing environmental impact remains important because these techniques help prevent global warming caused by halogen gases released during combustion.

Method used

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  • Synthetic method of 2,5-diaminotoluene and sulphate thereof
  • Synthetic method of 2,5-diaminotoluene and sulphate thereof
  • Synthetic method of 2,5-diaminotoluene and sulphate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: OT one-pot in-situ generation of 2,5-TDA and recovery and recycling of OT

[0067] Under stirring, 85.6g of o-toluidine (OT, 0.8mol) was added into a four-necked flask equipped with 390g of sulfuric acid (0.88mol) with a mass concentration of 22%, and the temperature was controlled at 0 to 5°C. Sodium nitrite aqueous solution (0.804mol) is slowly added dropwise to the sulfuric acid aqueous solution of OT over 30 minutes, after the addition is completed and stirred for 30 minutes to form the diazotization solution of OT, then slowly added dropwise over 60 minutes while maintaining 0-5°C as the coupling component 85.6g of OT (0.8mol, composed of 60.0g of recovered OT and 25.6g of industrial product OT) in the diazotization solution, the feeding temperature was controlled below 20°C, and the temperature was raised to 25°C and stirred for 6 hours after the addition, and the coupling reaction was completed. Add 350mL of water and stir to raise the temperature to 8...

Embodiment 2

[0069] Embodiment 2: 2,5-diaminotoluene sulfate (2,5-TDAS) preparation

[0070] The crude 2,5-TDA aqueous solution obtained in Example 1 was first added with 3.0 g of activated carbon for alkaline adsorption at 70° C., stirred for 10 minutes and then filtered hot, and a small amount of sulfuric acid was added to the filtrate from which the waste carbon was removed to adjust the pH to 6.0. Then add 3.0g of activated carbon for weak acid adsorption decolorization operation, stir and decolorize for 10min, then heat filter, the filtrate is light brown transparent liquid; continue to carry out repeated cycle decolorization operations under this weak acidic condition, until the filtrate is light yellow and transparent , slowly add 45mL of sulfuric acid (98%) dropwise under stirring to carry out acid precipitation and salt formation, stir and cool to below 10°C, filter, filter cake with 300mL cold water beating and washing and then filter, and vacuum dry at 60°C for 8 hours to obtain ...

Embodiment 3～7

[0072] Embodiment 3~7: One-pot synthesis 2,5-TDA and preparation 2,5-TDAS protection range test

[0073] Adopt the basic operation of embodiment 1 and embodiment 2, select different diazo components and coupling components, metallic zinc to replace iron, and adopt the feeding mode of different methods, i.e. the step-by-step method in embodiment 1 and simultaneous method (See Example 8), according to the method of the present invention and the different scope of protection, OT is the raw material one-pot synthesis of 2,5-TDA crude product aqueous solution and its OT recovery, and further prepares the test of 2,5-TDAS, The results are shown in the table below:

[0074] Table 1: Examples and comparisons of different diazo-coupling operations, OT quality and recovery in one-pot in situ synthesis

[0075] Reality

[0076] * The OT of diazo component all uses 99.8% industrial product, and the OT of coupling component selects 30% industrial product (99.8%) for use, 70% r...

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Abstract

The invention provides a method for economically synthesizing 2,5-diaminotoluene and sulfate of the 2,5-diaminotoluene. The method comprises that: ortoluidine(OT) is subjected to diazonium-coupled reaction under the action of sodium nitrite in inorganic acid water solution to form 2-amino azotoluol(C.I.11160); the 2-amino azotoluol is subjected to reduction hydrogenolysis reaction in the presence of metal or catalyst(Zn or Ni, Pd/C or Raney-Ni), simultaneously the by product of ortoluidine is distilled out by vapor for cyclical utilization, and the 2-amino azotoluol is filtered to synthesize 2,5-diaminotoluene water solution; furthermore, serial products of 2,5-diaminotoluene sulfate(2,5-TDAS) and free 2,5-diaminotoluene(2,5-TDA) of the 2,5-diaminotoluene sulfate are prepared. Due to the adoption of the one-pot in situ synthetic technique, the method has the characteristics of convenient operation, high yield, general equipment, higher recovery circulation rate, easy disposal of waste water, the reduction of waste water discharge by more than 40 percent, effective execution of clean production, generation of circular economy and the like.

Description

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Claims

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Application Information

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Owner 宁夏瑞鼎科技有限公司
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