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Preparation method of pyrene ketone type solvent dye

A technology of solvent dyes and pyrene, which is applied in the field of preparation of pyrene-based solvent dyes, can solve the problems of product separation, organic solvent recovery difficulties, incomplete DMF recovery, and high cost of wastewater treatment, and achieve complete solvent recovery, good quality, and applicable broad effect

Inactive Publication Date: 2019-05-17
NANTONG LONGXIANG NEW MATERIALS TECH CO LTD
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Problems solved by technology

However, both the aqueous phase method and the solvent method reported in the prior art have certain limitations, such as the aqueous phase method is usually only suitable for the preparation of solvent orange 60 and solvent red 135, and is not suitable for the preparation of solvent red 179; organic solvents are commonly used in the solvent method Including acetic acid, N,N-dimethylformamide, etc. After the reaction is completed, product separation and organic solvent recovery are relatively difficult, and the cost of wastewater treatment is high
[0003] Chinese patent CN201710748242 provides a so-called "semi-solvent method" for synthesizing pyrene dyes Solvent Red 179 and Solvent Orange 60 in DMF aqueous solution (mass concentration: 40-90%). This method collects different concentrations separately when recovering by distillation. DMF is used as reaction medium and washing medium respectively to realize solvent recovery and apply mechanically. Although the production cost is reduced to a certain extent, the operation is cumbersome, DMF recovery is not thorough, and this method is not universal. It is only suitable for solvent red 179 and solvent red 179. The preparation of orange 60 is not suitable for the preparation of solvent red 135

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  • Preparation method of pyrene ketone type solvent dye
  • Preparation method of pyrene ketone type solvent dye
  • Preparation method of pyrene ketone type solvent dye

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[0023] The present invention provides a method for preparing a pyrenone solvent dye, the pyrene solvent dye includes Solvent Orange 60, Solvent Red 135 or Solvent Red 179, and the preparation method includes the following steps:

[0024] 1,8-diaminonaphthalene, acid anhydride and non-water-soluble organic solvent are mixed and then subjected to condensation reaction to obtain pyrenone solvent dye;

[0025] The acid anhydride includes phthalic anhydride, tetrachlorophthalic anhydride or 1,8-naphthalene anhydride.

[0026] In the present invention, the pyrenone solvent dye prepared by using phthalic anhydride as a raw material is Solvent Orange 60, and the structural formula is as follows:

[0027]

[0028] The pyrenone solvent dye prepared with tetrachlorophthalic anhydride as a raw material is Solvent Red 135, and the structural formula is as follows:

[0029]

[0030] The pyrenone solvent dye prepared with 1,8-naphthalene anhydride as a raw material is Solvent Red 179, and the structur...

Embodiment 1

[0054] In a three-necked flask with stirring and reflux condenser, add 15.82g (0.1mol) of 1,8-diaminonaphthalene, 14.81g (0.1mol) of phthalic anhydride, 405.44g of toluene and 20.27g of acetic acid, turn on stirring, and heat to reflux State heat preservation reaction for 6h to obtain condensation product system;

[0055] Steam is introduced into the condensation product system for distillation, the distillate obtained by distillation is allowed to stand for stratification, and toluene is separated and recovered (recovery rate 98%); the residue obtained by distillation is suction filtered while hot, and the filter cake is heated at 60°C After washing with water until the filtrate is clear and the pH value is in the range of 6-8, 26.27 g of Solvent Orange 60 solid is obtained after drying (yield 97.2%).

[0056] Comparing the solvent orange 60 solid prepared in this example with the solvent orange 60 standard product, the ΔE is 0.35, the ΔC is 0.19, the strength is 100.72%, and the ...

Embodiment 2

[0058] In a three-necked flask with stirring and reflux condenser, add 15.82g (0.1mol) of 1,8-diaminonaphthalene, 14.81g (0.1mol) of phthalic anhydride, 405.44g of toluene and 40.54g of acetic acid, turn on stirring, and heat to reflux State insulation reaction for 3h to obtain condensation product system;

[0059] Steam is introduced into the condensation product system for distillation, the distillate obtained by distillation is allowed to stand for stratification, and toluene is separated and recovered (recovery rate of 97%); the residue obtained by distillation is suction filtered while hot, and the filter cake is heated at 80°C After washing with water until the filtrate is clear and the pH value is in the range of 6-8, 25.49g of Solvent Orange 60 is obtained by drying (94.3% yield).

[0060] Comparing the solvent orange 60 solid prepared in this embodiment with the solvent orange 60 standard product, the ΔE is 0.20, the ΔC is -0.09, the strength is 99.96%, and the product qua...

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Abstract

The invention relates to the technical field of chemical product preparation, in particular to a preparation method of pyrene ketone type solvent dye. The preparation method of the pyrene ketone typesolvent dye includes the following steps: 1,8-diaminonaphthalene, acid anhydride and a water-insoluble organic solvent are mixed and then subjected to a condensation reaction to obtain the pyrene ketone type solvent dye; and the acid anhydride comprises phthalic diamide, tetrachlorophthalic anhydride or 1,8-anhydride naphthalene. According to the preparation method of the pyrene ketone type solvent dye, the 1,8-anhydride naphthalene and the acid anhydride are subjected to the condensation reaction in the water-insoluble organic solvent, applicability is wide, all of solvent orange 60, solventred 135 and solvent red 179 can be synthesized through the preparation method, products have high yield and good quality; and in addition, the preparation method is a typical 'one-pot method', processequipment is simple, since the water-insoluble organic solvent is adopted, separation is easy in the post-processing process, solvent recovery is thorough, waste water has small amount and easy to treat, and the preparation method of the pyrene ketone type solvent dye is suitable for scale production.

Description

Technical field [0001] The invention relates to the technical field of chemical product preparation, in particular to a method for preparing pyrenone solvent dyes. Background technique [0002] Among the pyrenone solvent dyes, the most valuable ones are Solvent Orange 60, Solvent Red 135 and Solvent Red 179, which are composed of acid anhydride (phthalic anhydride, tetrachlorophthalic anhydride and 1,8-naphthalene anhydride) and 1,8-diaminonaphthalene It is prepared by condensation reaction and can be divided into water phase method and solvent method according to the reaction medium. However, the aqueous phase method and solvent method reported in the prior art have certain limitations. For example, the aqueous phase method is usually only suitable for the preparation of Solvent Orange 60 and Solvent Red 135, and is not suitable for the preparation of Solvent Red 179; organic solvents are commonly used in the solvent method. Including acetic acid, N,N-dimethylformamide, etc. Af...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09B57/12C09B67/22
Inventor 倪伟黄东升施烽
Owner NANTONG LONGXIANG NEW MATERIALS TECH CO LTD
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