Preparation method of double-acetyl-p-phenylenediamine bisazo compound

A technology of disazo compound and diacetoacetyl is applied in the field of preparation of disazo compound, can solve problems such as large raw materials, three wastes, waste, etc., and achieve the effects of reducing difficulty, avoiding decomposition of diazonium salt, and avoiding aggregation

Active Publication Date: 2013-07-31
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method brings great waste of raw materials and the pressure of "three wastes", which should not be advocated

Method used

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  • Preparation method of double-acetyl-p-phenylenediamine bisazo compound
  • Preparation method of double-acetyl-p-phenylenediamine bisazo compound
  • Preparation method of double-acetyl-p-phenylenediamine bisazo compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 20.9 parts of dimethyl 2-aminoterephthalate, 39.9 parts of 31% hydrochloric acid and 150 parts of water are beaten together at room temperature. Aqueous suspension of hydrochloride salt of dimethyl 2-aminoterephthalate was formed. Add ice and cool down to 0°C, add 6.9 parts of sodium nitrite to carry out diazotization reaction. A clear diazonium salt solution was obtained.

[0045] 13.8 parts of diacetoacetyl-p-phenylenediamine were stirred with 4.4 parts of sodium hydroxide and 100 parts of water to obtain a transparent solution. Add 0.2 part of emulsifier OS-15 and 0.1 part of dodecyl dimethyl benzyl ammonium chloride and stir well. Add 9 parts of sodium bicarbonate to obtain a coupling liquid; to be coupled.

[0046] Take out 10% of the total weight of the diazonium salt solution and put it into the reactor as the bottom liquid, add sodium acetate, adjust the pH to 3, and the temperature is 15°C. Under stirring, add the remaining diazonium salt solution and coupl...

Embodiment 2

[0061] The difference from Example 1 is:

[0062] The diazonium salt solution used as the bottom solution during the coupling reaction is 5% of the total amount of the diazonium salt solution. The final molar consumption ratio of dimethyl 2-aminoterephthalate and diacetoacetyl-p-phenylenediamine is 2:1.01,

[0063] Based on diacetoacetyl-p-phenylenediamine, the yield is 97.5%

Embodiment 3

[0065] 16.8 parts of 2-methoxy-4-nitroaniline, 29.4 parts of 31% hydrochloric acid and 60 parts of water were beaten together for 2 hours. Add ice and cool down to 0°C, add 6.9 parts of sodium nitrite to carry out diazotization reaction.

[0066] 13.8 parts of diacetoacetyl-p-phenylenediamine were stirred with 4.4 parts of sodium hydroxide and 100 parts of water to obtain a transparent solution. Add 0.2 part of emulsifier OS-15 and 0.1 part of dodecyl dimethyl benzyl ammonium chloride and stir well. Add 7 parts of sodium bicarbonate to be coupled.

[0067] Take out 10% of the total weight of the diazonium salt solution and put it into the reactor as the bottom liquid, add sodium acetate, adjust the pH to 4, and the temperature is 8°C. Within 2 hours, continuously and slowly add the remaining diazonium salt solution and the coupling solution to the base solution at a molar ratio of 2:1 until all the diazonium salts are added. Slowly add the remaining coupling solution until ...

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Abstract

The invention relates to a preparation method of a double-acetyl-p-phenylenediamine bisazo compound. The method comprises adding sodium hydroxide into a water suspension of coupling components double-acetyl-p-phenylenediamine or derivatives thereof to prepare an aqueous solution, adding an acid binding agent and a surfactant to obtain a coupling liquid; preparing diazo components into a diazo liquid; taking part of the diazo liquid as a base solution, adjusting a pH to 3-7 by using sodium acetate; continuously adding the residual diazo liquid and the coupling liquid into the base solution according to equal chemical reaction amount in a concurrent flow feed way with stirring for a coupling reaction, and supplementing residual coupling liquid when all the diazo salt is added until all diazonium salt disappears by an H acid detection, thereby finishing the reaction and obtaining the compound of a general formula I, wherein a mole ratio of the diazo components and the coupling components is 2 : 1. According to the invention, a yield of the coupling method is more than 98 %, and meanwhile usage of a common buffer system acetic acid / acetate can be reduced or omitted, thereby greatly reducing a COD of synthetic wastewater.

Description

technical field [0001] The invention relates to the preparation of disazo compounds, in particular to a preparation method of bisacetoacetyl-p-phenylenediamine disazo compounds. Background technique [0002] The structure of disazo compounds prepared by using diacetoacetyl-p-phenylenediamine and its derivatives as coupling components and substituting aromatic primary amines is not new, and it was reported as early as 1940. Such compounds can be used in the fields of coatings, plastics, inks and the like to obtain colorants after crystal form adjustment and surface treatment. Pigment Yellow 155, Pigment Yellow 198, etc. are all pigments of this structure type. The macromolecular condensed azo yellow 93, 94, 95, 128, etc. also use this as the main structure. [0003] The synthetic route of this kind of compound is usually to diazotize the primary aromatic amine, and carry out coupling with bis-acetoacetyl-p-phenylenediamine to complete the reaction. The coupling method can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B33/153C07C245/06
Inventor 王永华朱红卫杨林涛闫燕
Owner 中国中化股份有限公司
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