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A kind of method utilizing 4,4'-diisopropoxydiphenylsulfone to prepare 4-hydroxyl-4'-isopropoxydiphenylsulfone

A technology of propoxydiphenyl sulfone and hydroxyl, which is applied in the chemical field, can solve the problems of expensive hydrobromic acid and long reaction time, and achieve the effect of recycling resources and shortening reaction time

Active Publication Date: 2021-08-13
JIANGSU AOLUNDA HIGH TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] But this technique has disadvantages: the reaction system must add solvent acetic acid, and hydrobromic acid must be used as a dealkylation agent. If acetic acid and hydrogen bromide are not added, the reaction time of other acidic substances needs to be very long, and the use of acetic acid also brings In addition to the problem of acetic acid recovery, hydrobromic acid is also very expensive, and the highest yield is only 45%, so this process still has a lot of shortcomings

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Put 33.4 grams (0.1mol) of 4,4'-diisopropoxydiphenylsulfone and 53.3 grams of 30% sodium hydroxide, 267.2 grams of isopropanol, 100 grams of water and catalyst N-bis(dimethylamino) Add 0.007 g of methylene-1.3-dimethylimidazoline-2-imonium chloride salt into a 1-liter autoclave, stir and heat to 160°C, react for 2 hours, and detect by liquid chromatography that no 4,4' -Diisopropoxydiphenyl sulfone, stop the reaction, distill isopropanol under reduced pressure, adjust the pH value of the system with dilute hydrochloric acid, filter, and the filtrate contains 4,4'-dihydroxydiphenyl sulfone, which can be used as synthetic 4-hydroxy- The starting material of 4'-isopropoxydiphenyl sulfone, the obtained filter cake was dissolved in water, the pH value was adjusted to 5-6, filtered, and the filter cake was dried to obtain 20.4g (yield 69.1%) 4-hydroxy -4'-isopropoxydiphenyl sulfone, content 99%.

Embodiment 2

[0025] Put 33.4 grams (0.1mol) of 4,4'-diisopropoxydiphenylsulfone and 5.67 grams of 99% potassium hydroxide, 66.8 grams of isopropanol, 308 grams of water and catalyst N-bis(dimethylamino) Add 0.835 g of methylene-1.3-dimethylimidazoline-2-imonium chloride salt into a 1-liter autoclave, stir and heat to 130°C, react for 5 hours, and detect by liquid chromatography that there is no 4,4' -Diisopropoxydiphenylsulfone, after the reaction, distill isopropanol under reduced pressure, adjust the pH value of the system with dilute hydrochloric acid, filter, and the filtrate contains 4,4'-dihydroxydiphenylsulfone, which can be used as a synthetic 4-hydroxy - The starting material of 4'-isopropoxydiphenyl sulfone, the obtained filter cake was dissolved in water, the pH value was adjusted to 5-6, filtered, and the filter cake was dried to obtain 21.6g (73.1% yield) of 4- Hydroxy-4'-isopropoxydiphenyl sulfone, content 99%.

Embodiment 3

[0027] Put 33.4 grams (0.1mol) of 4,4'-diisopropoxydiphenyl sulfone and 20 grams of 30% sodium hydroxide, 133.6 grams of isopropanol, 380 grams of water and catalyst N-bis(dimethylamino) Add 0.42 g of methylene-1.3-dimethylimidazoline-2-imonium chloride salt into a 1-liter autoclave, stir and heat to 110°C, react for 6 hours, and detect by liquid chromatography that no 4,4' exists -Diisopropoxydiphenylsulfone, after the reaction, distill isopropanol under reduced pressure, adjust the pH value of the system with dilute hydrochloric acid, filter, and the filtrate contains 4,4'-dihydroxydiphenylsulfone, which can be used as a synthetic 4-hydroxy - The starting material of 4'-isopropoxydiphenyl sulfone, the obtained filter cake was dissolved in water, the pH value was adjusted to 5-6, filtered, and the filter cake was dried to obtain 19.6g (66.4% yield) of 4- Hydroxy-4'-isopropoxydiphenyl sulfone, content 99%.

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Abstract

The invention relates to a method for preparing 4-hydroxy-4'-isopropoxydiphenyl sulfone by using 4,4'-diisopropoxydiphenylsulfone. Under the action of a phase transfer catalyst, 4,4'-diphenylsulfone Isopropoxydiphenyl sulfone undergoes alkaline hydrolysis reaction in a solvent in the presence of alkaline substances, the reaction temperature is 110-160°C, the reaction time is 2-6 hours, and the product is post-treated and acidified to obtain 4-hydroxy-4'-iso Propoxydiphenylsulfone. The invention can realize higher yield of 4-hydroxyl-4'-isopropoxydiphenyl sulfone, thereby solving the problem of recovery and reuse of by-product 4,4'-diisopropoxydiphenyl sulfone.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to an industrial preparation method of 4-hydroxyl-4'-isopropoxydiphenyl sulfone used as a color developer for thermosensitive recording materials. Background technique [0002] 4-Hydroxy-4'-isopropoxydiphenyl sulfone is a heat-sensitive developer with excellent performance, and its preparation method has been published in the Japanese Patent Publication for a long time, such as patent No. 58-20493, No. 60-13852 , Zhao 58-82788, etc., WO91 / 11433 and Chinese patent 00805402.9 also disclose the synthesis method. Route synthesis mostly adopts 4-hydroxyl-4'-isopropoxydiphenyl sulfone synthesized from bisphenol S and 2-bromopropane or 2-iodopropane as raw materials. [0003] Reaction equation: [0004] , [0005] However, in the reaction process, the double-substituted by-product 4,4'-diisopropoxydiphenyl sulfone is inevitably produced simultaneously. If it is too high in the pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/04C07C317/22
CPCC07C315/04C07C317/22
Inventor 陈律陈盘强王崇玥
Owner JIANGSU AOLUNDA HIGH TECH IND