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Synthetic method of red naphthalene cyclic ketone dye

A synthesis method and a technology of naphthocyclic ketone are applied in the manufacturing field of chemical dyes, which can solve the problems of low solvent recovery rate, high price and high solvent price, and achieve the effects of good shade and high product yield.

Inactive Publication Date: 2018-05-18
JIANGSU DAOBO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

About the preparation of solvent red 135 by solvent method, there are reports both at home and abroad. The yield is high and the quality is good, but there are many problems, which are mainly reflected in the following two aspects: (1) the solvent recovery rate is low, which is related to the selection of solvent. If If you choose a low boiling point solvent, the loss during the recovery process will become very large
(2) solvent price is high, as the technology of US5830931 report is to adopt N-methyl-γ-butyrolactam as reaction medium, although yield is up to 97%, and product quality is good, but this solvent price is high, belongs to low boiling point again Solvent, the loss in the recovery process is large, which further increases the cost of the product

Method used

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  • Synthetic method of red naphthalene cyclic ketone dye
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  • Synthetic method of red naphthalene cyclic ketone dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The o-dichlorobenzene of 150g and the tetrachlorophthalic anhydride of 50g are dropped into the reactor that has water separator and reflux condenser, after stirring for 0.5h, add 27.8g of 1,8-diaminonaphthalene and 4.5g of PEG-600 and Start to heat up and turn on the circulating water at the same time. When the temperature rises above 150°C, heat preservation starts, followed by HPLC. After 5.5 hours, the heat preservation ends, and the temperature is lowered to 80°C. It is isolated with 37.5g of methanol, and after the separation is completed, it is lowered to 50°C. Suction filtration, the filter cake is soaked in a small amount of methanol, drained, and again Wash with a small amount of methanol, drain, discharge, and vacuum-dry the filter cake at 50°C for 24 hours to obtain 66.3g of the product, with a yield of 93%. Compared with the standard product, the color and intensity are as follows:

[0023] △E*

[0024] Among them, △E* is the total color difference...

Embodiment 2

[0026] Put 200g of o-dichlorobenzene and 50g of tetrachlorophthalic anhydride into the reactor with water separator and reflux condenser, add 27.8g of 1,8-diaminonaphthalene and 6g of PEG-600 after stirring for 0.5h and start Raise the temperature and turn on the circulating water at the same time. When the temperature rises above 155°C, heat preservation starts, followed by HPLC. After 5 hours, the heat preservation ends, and the temperature is lowered to 80°C. Isolate with 50g of methanol. After the separation is completed, the temperature is lowered to 50°C. Suction filtration, the filter cake is soaked in a small amount of methanol, drained, and again with a small amount of Washed with methanol, drained, and discharged, the filter cake was vacuum-dried at 50°C for 24 hours to obtain 67.4g of the product, with a yield of 94.5%. Compared with the standard product, the shade and intensity were as follows:

[0027] △E*

Embodiment 3

[0029] 250g of o-dichlorobenzene and 50g of tetrachlorophthalic anhydride are dropped into a reactor with a water separator and a reflux condenser, and after stirring for 0.5h, 27.8g of 1,8-diaminonaphthalene and 7.5g of PEG-600 are added and Start to heat up and turn on the circulating water at the same time. When the temperature rises above 155°C, heat preservation starts, followed by HPLC. After 5 hours, the heat preservation ends, and the temperature is lowered to 90°C. It is isolated with 62.5g of methanol. After the separation is completed, it is lowered to 50°C. Suction filtration, the filter cake is soaked in a small amount of methanol, drained, and used again A small amount of methanol was washed, drained, and the material was discharged. The filter cake was vacuum-dried at 50°C for 24 hours to obtain 68.1 g of the product, with a yield of 95.5%. Compared with the standard product, the color and intensity were as follows:

[0030] △E*

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Abstract

The invention discloses a synthetic method of red naphthalene cyclic ketone dye, comprising the steps of with ortho-dichlorobenzene as a reaction solvent, PEG-600 as a catalyst and tetrachlorophthalicanhydride and 1,8-diaminonaphthalene as main materials, holding a certain temperature, isolating water produced in reaction to raise the temperature, performing HPLC (high performance liquid chromatography) medium control, cooling with 1,8-diaminonaphthalene < / =0.5% as a reaction endpoint, separating certain methanol, performing suction filtering, washing filter cake with methanol until there isno smell of ortho-dichlorobenzene, vacuum-drying the filter cake to obtain the target product solvent red 135. The solvent ortho-dichlorobenzene used herein has high boiling point, the recovery rate may reach 95% and above, product yield is high, and the product has good color tone; compared with standards, the product has DC of about 0.5 and weighted strength of about 105.

Description

technical field [0001] The invention relates to a green synthesis method of red naphthylcyclone dye, which belongs to the technical field of chemical dye manufacture. Background technique [0002] Solvent red 135, also known as transparent red EG or oil soluble red 135, belongs to naphthylcyclone dyes structurally, chemical name: 8,9,10,11-tetrachloro-12H-phthalophthalein-12- Ketone, CAS: 20749-68-2, bright red powder in appearance. Solvent Red 135 is insoluble in water, and has relatively low solubility in organic solvents such as o-dichlorobenzene, toluene, DMF, and acetone. Solvent Red 135 is not only used for the coloring of various resins, such as ABS, polyvinyl chloride, plexiglass, polystyrene, etc., but also for the coloring of polyester fiber and acetate fiber. The structural formula is as follows: [0003] [0004] At present, the industrial manufacture of solvent red 135 is mainly divided into two categories: aqueous phase method and solvent method. The wat...

Claims

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Application Information

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IPC IPC(8): C09B57/12
CPCC09B57/12
Inventor 刘学峰徐松汪港
Owner JIANGSU DAOBO CHEM
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