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Benzodifuranone dye synthetic method

The technology of a kind of benzodifuranone and the synthetic method is applied in the field of chemical industry, which can solve the problems of high production cost of disperse dyes, unavoidable highly toxic sodium cyanide, dangerous production process, etc., and achieves cheap and easy-to-obtain production raw materials, good industrial Application prospect, low risk effect

Active Publication Date: 2018-08-17
大连傲视化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In this process, the mandelic acid-like structure intermediate (2, 2′) is usually synthesized using highly toxic sodium cyanide, and the starting material is aromatic formaldehyde or aromatic ethyl ketone with a higher price, and the yield is between 60% and 70%. Yield is on the low side; And intermediate 3 uses relatively high hydroquinone as raw material; Ammonium thiocyanate or sodium thiocyanate of stoichiometric equivalent is used in the final oxidation process, because the above-mentioned raw material price is higher, yield The production cost of benzodifuranone disperse dyes is relatively low, and the highly toxic sodium cyanide is unavoidably used in the process, which makes the production process more dangerous and the three wastes are difficult to handle; while the equivalent level of thiocyanate is oxidized , resulting in high salinity wastewater that is difficult to treat

Method used

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  • Benzodifuranone dye synthetic method
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  • Benzodifuranone dye synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Add monomethyl oxalyl chloride (73.4g, 599mmol) to a solution of aluminum trichloride (92.5g, 693mmol) in dichloromethane (800g) at 0-5°C, and stir for 30 minutes at this temperature Benzene (39g, 500mmol) was added dropwise in the reaction solution, after the dropwise addition, the reaction solution was stirred at room temperature for 4 hours, the reaction solution was poured into the ice-water mixture, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, and the solvent was recovered in vacuo, and the inside of the kettle was a light yellow viscous liquid (Intermediate 1) (82g, yield 94%);

[0030] (2) Add monomethyl oxalyl chloride (73.4g, 599mmol) to a solution of aluminum trichloride (92.5g, 693mmol) in dichloromethane (800g) at 0-5°C, and stir for 30 minutes at this temperature ; In the reaction solution, dropwise add the dichloromethane (120g) solution of phenbutyl ether (75g, 500mmol), d...

Embodiment 2

[0036] (1) Add monoethyl oxalyl chloride (81.5g, 599mmol) to a solution of zinc dichloride (95.2g, 700mmol) in chloroform (800g) at 0-5°C, and stir for 30 minutes at this temperature; Benzene (39g, 500mmol) was added dropwise to the reaction solution. After the addition was complete, the reaction solution was stirred at room temperature for 4 hours. The reaction solution was poured into a mixture of ice and water, and the organic layer was separated. The aqueous layer was extracted with chloroform, and the organic layers were combined. The solvent was recovered in vacuo, and the still was light yellow viscous liquid (intermediate 1) (89g, yield 95%);

[0037](2) Add monoethyl oxalyl chloride (81.5g, 599mmol) to a solution of zinc dichloride (95.2g, 700mmol) in chloroform (600g) at 0-5°C, and stir for 30 minutes at this temperature; A solution of 2-(phenoxymethyl)tetrahydrofuran (106.6 g, 599 mmol) in chloroform (120 g) was added dropwise to the reaction solution. After the add...

Embodiment 3

[0043] (1) Add monomethyl oxalyl chloride (73.4g, 599mmol) to a solution of aluminum trichloride (95.2g, 700mmol) in ethylene dichloride (800g) at 0-5°C, and stir for 30 minutes; in the reaction solution, benzene (39g, 500mmol) was added dropwise, after the dropwise addition, the reaction solution was stirred at room temperature for 4 hours, the reaction solution was poured into the ice-water mixture, the organic layer was separated, and the aqueous layer was extracted with dichloromethane , merging the organic layers, and recovering the solvent in vacuo, the still was light yellow viscous liquid (intermediate 1) (83g, yield 95%);

[0044] (2) Add monomethyl oxalyl chloride (73.4g, 599mmol) to a solution of ferric chloride (113.7g, 700mmol) in ethylene dichloride (600g) at 0-5°C, and stir for 30 minute; in the reaction solution, dropwise add the dichloromethane (120g) solution of phenylpropyl ether (81.5g, 599mmol), dropwise, the reaction solution was stirred at room temperatu...

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Abstract

The invention relates to a benzodifuranone dye synthetic method which comprises the following steps of by taking alkyl ester oxalyl monochloride and aromatic hydrocarbon as raw materials, performing Friedel-Crafts reaction to prepare an intermediate 1 or 1', performing hydrogenation reduction on the intermediate 1 and the intermediate 1' to prepare an intermediate 2 and an intermediate 2', performing condensation reaction on the intermediate 2, an intermediate 3 as a condensation product of p-chlorophenol and then the intermediate 2' to produce an intermediate 4, and performing oxidation on the intermediate 4 to obtain benzodifuranone. The synthetic technology provided by the invention is low in cost, dangerousness and pollution, is simple in technology route without single purification process, is cheap and available in production raw material, has the cost far lower than the cost of the existing technology, is relatively high in the total yield, reaching 69 percent of a product, hasthe content being larger than 98.5 percent, has very high economic benefit, is suitable for mass production and has a good industrial application prospect.

Description

technical field [0001] The invention relates to a synthesis method of benzodifuranone dyes, which belongs to the field of chemical industry. Background technique [0002] Disperse Red 356 and Disperse Red SBWF are the main varieties of benzodifuranone disperse dyes. Because these dyes have high color brightness and luminous intensity, and have excellent dyeing performance, they are widely used in On polyester microfiber. [0003] The production technology of benzodifuranone disperse dyes in the prior art is as follows: [0004] [0005] In this process, the mandelic acid-like structure intermediate (2, 2′) is usually synthesized using highly toxic sodium cyanide, and the starting material is aromatic formaldehyde or aromatic ethyl ketone with a higher price, and the yield is between 60% and 70%. Yield is on the low side; And intermediate 3 uses relatively high hydroquinone as raw material; Ammonium thiocyanate or sodium thiocyanate of stoichiometric equivalent is used i...

Claims

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Application Information

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IPC IPC(8): C09B57/00
CPCC09B57/00
Inventor 李水明段玉辉
Owner 大连傲视化学有限公司
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