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Method for synthesizing naphthoquinone sulfonyl chloride

A technology of naphthoquinone sulfonyl chloride and naphthoquinone sulfonic acid, which is applied in the fields of sulfonic acid preparation and organic chemistry, can solve the problems of large amount of diphosgene and solid phosgene and low reaction temperature, so as to ensure the safe operation and reaction of equipment The effect of mild temperature and easy control

Inactive Publication Date: 2016-07-13
DENBISHI FINE CHEM DALIAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction temperature used in this method is on the low side, and the amount of diphosgene and solid phosgene used is relatively large, so there are problems in industrial scale-up production

Method used

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  • Method for synthesizing naphthoquinone sulfonyl chloride
  • Method for synthesizing naphthoquinone sulfonyl chloride
  • Method for synthesizing naphthoquinone sulfonyl chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0030] This embodiment is the synthesis of 2-diazo-1-naphthoquinone-4-sulfonyl chloride:

[0031] Add 25.02g (0.1mol) of 2-diazo-1-naphthoquinone-4-sulfonic acid and 600mL of 1,2-dichloroethane into a 1000mL reaction flask, and add 19.6g of bis(trichloromethyl)carbonate (0.067 mol). Under the condition of ice-water bath, 10.1 g (0.1 mol) of triethylamine was added dropwise to the reaction flask, and a white solid was produced in the reaction mixture at this time. After dropping, stir the reaction for 30min; slowly warm the reaction mixture to 40oC and stir the reaction for 2h. Cooled down to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was added to 500 mL of ice-water mixture, stirred for 5 min, and a solid precipitated out. Filter and wash the filter cake with a small amount of ice-water mixture. The solid product was dried under vacuum. 23.0 g of the product was obtained with a yield of 81%. HPLC detection purity: 95.7%. ...

Embodiment 2

[0033] This embodiment is the synthesis of 2-diazo-1-naphthoquinone-5-sulfonyl chloride:

[0034] Add 25.02g (0.1mol) of 2-diazo-1-naphthoquinone-5-sulfonic acid and 300mL of 1,2-dichloroethane into a 1000mL reaction bottle, add 50.5g (0.5mol) of triethylamine in an ice-water bath Under the conditions, a solution prepared by 29.2 g (0.1 mol) of bis(trichloromethyl)carbonate and 300 mL of 1,2-dichloroethane was added dropwise into the reaction flask. At this point a white solid formed in the reaction mixture. After dropping, stir and react for 30 minutes; keep stirring and react for 4.0 hours. The reaction mixture was concentrated under reduced pressure. The residue was added to 500 mL of ice-water mixture, stirred for 5 min, and a solid precipitated out. Filter and wash the filter cake with a small amount of ice-water mixture. The solid product was dried under vacuum. 24.2 g of the product was obtained with a yield of 85.0%.

[0035] figure 1 HPLC analysis spectrum of n...

Embodiment 3

[0037] This embodiment is the synthesis of 2-diazo-1-naphthoquinone-5-sulfonyl chloride:

[0038]Add 25.02g (0.1mol) of 2-diazo-1-naphthoquinone-5-sulfonic acid and 600mL of 1,2-dichloroethane into a 1000mL reaction flask, and add 19.6g of bis(trichloromethyl)carbonate (0.067 mol). Under the condition of ice-water bath, 10.1 g (0.1 mol) of triethylamine was added dropwise to the reaction flask, and a white solid was produced in the reaction mixture at this time. After dropping, stir and react for 30min; slowly warm the reaction mixture to 40oC and stir for 2.0h. Cooled down to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was added to 500mL of ice-water mixture, stirred for 5min, and a solid precipitated out. Filter and wash the filter cake with a small amount of ice-water mixture. The solid product was dried under vacuum. 24.2 g of the product was obtained with a yield of 85%. HPLC detection purity: 97.4%.

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Abstract

The invention discloses a method for synthesizing naphthoquinone sulfonyl chloride and belongs to the technical field of organic synthesis.The method includes the step that naphthoquinone sulfonyl chloride is synthesized by naphthoquinone sulfonic acid and di(trichloromethyl) carbonic ester in an inert solvent under the condition that organic base serves as a catalyst.Naphthoquinone sulfonic acid serves as a raw material, safe and environment-friendly di(trichloromethyl) carbonic ester serves as an acylating chlorination reagent, the organic base is used, naphthoquinone sulfonyl chloride is prepared at moderate temperature under simple and convenient operating conditions, industrial production of the compound is promoted, and the whole reaction process meets the requirements on safety and environment friendliness.The yield of the prepared naphthoquinone sulfonyl chloride product is larger than 80%, and the purity of the prepared naphthoquinone sulfonyl chloride product is larger than 95%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing naphthoquinonesulfonyl chloride. Background technique [0002] Naphthoquinone compounds are a class of photosensitive compounds, mainly used in the field of photosensitive materials, such as color film, offset printing, electronic imaging and other industries, and are an important class of chemical products. Naphthoquinonesulfonyl chloride is an intermediate with the best optical activity in this type of compound. After it undergoes an esterification reaction with a compound containing a hydroxyl group, it generates a compound with photosensitive properties. It is used in the material of the positive PS plate SCPG has the characteristics of high power, good resolution, and wide photosensitive range, especially when combined with novolac resin, it has the advantages of developing alkaline water, environmental protection, and large tolerance, so ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/85C07C309/88
CPCC07C303/02C07C309/85C07C309/88
Inventor 赵宏赵世龙任相武
Owner DENBISHI FINE CHEM DALIAN CO LTD
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