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Preparation method of pyrene ketone solvent dye

A solvent dye, renone type technology, applied in the green preparation field of renone type solvent dye, can solve the problems of large amount of waste water, equipment corrosion, not belonging to green process, etc., and achieves the effect of high cost performance and good quality

Active Publication Date: 2017-12-15
宁波龙欣精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this process has the following disadvantages: one is that glacial acetic acid is used as a solvent, which seriously corrodes the equipment; the other is that the residual acetic acid in the filter cake is difficult to recycle, and the COD of wastewater is very high
This process has the following disadvantages: one is that the concentration of sulfuric acid in the reaction system is 5-8%, and the reaction temperature exceeds 90°C, which seriously corrodes the reaction equipment; the other is that the added hydrophilic substances of 5-8% are neither recovered , and there is no mother liquor, it will exist in the waste water, resulting in high COD
This process has the following disadvantages: one is that the low-concentration hydrochloric acid solution is in a high-temperature reflux state for a long time, which seriously corrodes the equipment; the other is that nonylphenol polyoxyethylene ether (NPEO) has greater harm to the environment; Wastewater COD is very high, and the amount of wastewater is large, and there is no recycling, and this process is not a green process

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In a 250ml four-neck flask, nitrogen gas was introduced, 230g of 80% DMF aqueous solution was added, and 0.8g of sodium sulfite, 15.8g (0.1mol) of 1,8-diaminonaphthalene, and 15.1g (0.102 mol), 0.6g PEG-400. Raise the temperature to micro-reflux (about 108-115°C) and keep it warm for 10 hours. Take a sample to detect the end point. After the end point is reached, cool down to room temperature and filter. The filter cake is soaked twice with 50g 30% DMF, drained, and then washed with 25g 60% DMF. Soak in hot water at about ℃ and drain, and combine the filtrates for recovery. The filter cake is washed with hot water at about 60°C until the color does not fade, and then dried at 105°C. 25.9 g of bright orange solvent orange 60 crystals were obtained (yield 95.9%), and the shade and intensity were ΔC 0.14, ΔE 0.42, and intensity 99.8% compared with the standard product.

[0036]Recovery of DMF: In a 500ml four-neck flask equipped with a thermometer, packed column, condens...

Embodiment 2

[0038] Replace "PEG-400" with "PEG-600", and the rest are the same as in Example 1. 25.7 g of bright orange solvent orange 60 crystals were obtained (yield 95.2%), compared with the standard product, ΔC 0.24, ΔE 0.46, and intensity 100.9%.

[0039] The DMF recovery process is the same as in Example 1, and the DMF recovery rate is 92.1%.

Embodiment 3

[0041] In a 500ml four-neck flask, blow nitrogen gas, add 270g of 70% DMF aqueous solution, add 0.65g of sodium dithionite, 15.8g (0.1mol) of 1,8-diaminonaphthalene, and 15.1g of phthalic anhydride under stirring (0.102 mol), 0.8 g PEG-400. Raise the temperature to micro-reflux (about 105-112°C) and keep it warm for 12 hours, take a sample to detect the end point, after the end point is reached, cool down to room temperature, filter, soak the filter cake twice with 50g of 20% DMF, and then heat it with 25g of 60°C or so Wash once with water, drain, and combine the filtrates for recovery. The filter cake is washed with hot water at about 60°C until the color does not fade, and then dried at 103°C. 25.4 g of bright orange solvent orange 60 crystals were obtained (yield 94.1%), compared with the standard product, ΔC 0.12, ΔE 0.35, and strength 99.6%.

[0042] Reclaim DMF: in 500ml flask, add DMF filtrate to be recovered, distill, collect 100~115 ℃ fraction 100g (DMF aqueous sol...

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Abstract

The invention discloses a preparation method of a pyrene ketone solvent dye. The preparation method comprises the following steps: (1) under double protection of a nitrogen atmosphere and a reducing agent, reacting 1,8-diaminonaphthalene with phthalic anhydride (or 1,8-naphthalic anhydride) under the action of phase transfer catalyst polyethylene glycol in DMF aqueous solution under reflux temperature; (II) after condensation end point, cooling the reaction solution to room temperature, filtering and washing a filter cake by the DMF aqueous solution with low concentration. The dyes involved are solvent orange 60 (C.I.564100) and solvent red 179 (C.I.564150). Under the double protection of the reducing agent and the nitrogen atmosphere, the target product is formed with high conversion rate in DMF-water mixed solvent by means of the phase transfer catalyst, high quality dye is obtained by simple separation, and more than 90% solvent (in DMF) is recovered, and the preparation method of the pyrene ketone solvent dye is a green preparation method.

Description

technical field [0001] The invention relates to the field of dye preparation technology, in particular to a green preparation method of a perone-type solvent dye. Background technique [0002] The representative varieties of perphenone-type solvent dyes are mainly solvent orange 60, solvent red 135, and solvent red 179, and their synthesis processes are roughly divided into two categories: aqueous method and solvent method. The product quality of the solvent method is relatively good, but the cost is high; the product cost of the aqueous phase method is low, but the quality is relatively poor, and the material has no crystallization, which is not popular in the market. The "water phase method" here is not the water phase method in the absolute sense, it generally refers to the solvent content below 20%, and the solvent is not recycled, and the water phase method usually uses 5-10% acid to make Catalyst, more serious corrosion to equipment. [0003] CN100413928C discloses a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06C07D471/06C09B57/12
CPCC07D471/06C07D487/06C09B57/12
Inventor 周善波丁秋龙周俞刘晓梅
Owner 宁波龙欣精细化工有限公司
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