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New green synthesizing process for ketocoumaran compound

A technology for the synthesis of benzodifuranone, which is applied in organic chemistry, chemical instruments and methods, azo dyes, etc., can solve the problems of large amount of waste acid, low yield, and not very high yield, and achieve environmental pollution Small size, good perspiration fastness, and the effect of reducing the amount of acid

Active Publication Date: 2012-07-25
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional solid-phase method requires a higher temperature, generally between 190 and 200°C, and the yield is low. In order to overcome this shortcoming, it is improved and carried out in the solvent acetic acid or concentrated sulfuric acid, and the temperature is reduced to 60-130°C (because Different solvents are slightly different), and a certain amount of acid is added as a catalyst, which improves the yield, but due to the large amount of use of acetic acid and concentrated sulfuric acid, the amount of waste acid is large, and the yield is not very high

Method used

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  • New green synthesizing process for ketocoumaran compound
  • New green synthesizing process for ketocoumaran compound
  • New green synthesizing process for ketocoumaran compound

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 0.05g 98% concentrated sulfuric acid (0.5mmol), 0.3043g (2mmol) mandelic acid, 0.1101g (1.0mmol) hydroquinone in the mortar successively, grind evenly, react at a constant temperature of 130°C for 4h, wait for the product to cool, use Scrape off with a spatula, transfer to a 10mL test tube, add 2g of acetic acid, 0.23g (2mmol) of 30% aqueous hydrogen peroxide solution, react at 50°C for 5h, cool the reaction solution to below 10°C, filter with suction to obtain a reddish-brown solid and dry it in vacuum to obtain Crude product 0.2376g, crude yield 69.88%. Recrystallized from toluene to obtain a dark red flaky solid.

Embodiment 2

[0033] Add 0.03g polyphosphoric acid (0.3mmol), 0.4553g (2.5mmol) p-methoxymandelic acid, 0.1101g (1.0mmol) hydroquinone in the mortar in turn, grind evenly, react at a constant temperature of 80°C for 8h, and wait for production The substance was cooled, scraped off with a spatula, transferred to a 10mL test tube, added 2g of acetic acid, 0.23g (2mmol) of 30% hydrogen peroxide aqueous solution, and reacted at 50°C for 5h, cooled the reaction solution to below 10°C, and filtered the obtained solid under vacuum After drying, a crude product was obtained, which was recrystallized from toluene to obtain 0.2560 g of a dark red flaky solid.

Embodiment 3

[0035] Add 0.027g zinc chloride (0.2mmol), 0.2103g (1.0mmol) p-propoxymandelic acid, 0.1101g (1.0mmol) hydroquinone in the mortar, grind evenly, and react at a constant temperature of 100°C for 2 hours. Add 0.1863g (1.0mmol) p-chloromandelic acid, grind evenly, and react at a constant temperature of 100°C for 4h. After the product is cooled, scrape it off with a scraper, transfer it to a 10mL test tube, add 2g of acetic acid, 0.23g of 30% aqueous hydrogen peroxide ( 2mmol), reacted at 50°C for 5h, cooled the reaction liquid to below 10°C, and vacuum-dried the solid obtained by suction filtration to obtain a crude product, which was recrystallized with toluene to obtain 0.1854g of a solid product.

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Abstract

The invention discloses a new green synthesizing process for a ketocoumaran compound. The synthesizing process comprises the following steps: in the absence of a solvent, performing condensation reaction of a mandelic acid compound and hydroquinol under the action of a little amount of acid catalyst to obtain a full condensed intermediate, wherein the acid catalyst is selected from one of 10 to 37 percent concentrated hydrochloric acid, 60 to 98 percent concentrated sulfuric acid, fuming sulfuric acid, 80 to 98 percent phosphoric acid, polyphosphoric acid, p-toluenesulfonic acid, trifloromethanesulfonic acid, benzoic acid, ammonium acetate, ammonium chloride, KF, TiC14, NiCl2, CuSO4, Cu(OAc)2, ZnCl2, AlCl3, Fe(NO3)3, FeCl3 and SnCl2; and performing oxidation reaction of full condensed intermediate under the action of an oxidant to obtain a final product ketocoumaran compound. The synthesizing process of the invention is simple, and has low energy consumption and little environmental pollution.

Description

(1) Technical field [0001] The invention relates to a process for synthesizing benzodiofuranone compounds by using mandelic acid compounds and hydroquinone as raw materials. (2) Background technology [0002] Benzodifuranone is a new type of chromophore. In the 1970s, companies such as Imperial Chemicals (ICI) in Britain, Bayer in Germany, and Sumitomo in Japan successively introduced a new type of disperse dye—— Benzodifuranone disperse dyes. This kind of dye has excellent properties such as bright color, high color value, and good fastness, and its application effect on ultrafine denier fibers is excellent. [0003] Among disperse dyes, anthraquinone dyes are not as good as cheap azo dyes in terms of color intensity, and have disadvantages such as low fastness to wet treatment, relatively high price, and serious pollution, while azo dyes cannot reach the performance of anthraquinone dyes. Vibrant color. The benzodifuranone dyes just make up for the shortcomings of the a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04C07D487/04C07D495/04C09B57/00
CPCC09B57/00
Inventor 李郁锦高建荣贾建洪韩亮盛卫坚
Owner ZHEJIANG UNIV OF TECH
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