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ChemicalBook CAS DataBase List Benzanthrone
82-05-3

Benzanthrone synthesis

13synthesis methods
Benzanthrone is prepared commercially by reacting anthraquinone with glycerol, sulfuric acid, and a reducing agent, usually iron. This involves reduction of anthraquinone to anthrone (122), which condenses immediately with the acrolein formed by dehydration of glycerol, and is finally oxidized by the sulfuric acid , , . An improved process is described in , . More recently, the use of phosphorus or a phosphorus compound, e.g., sodium hypophosphite, has been proposed as the reducing agent . Electrochemical procedures have been also suggested , . It is possible to start with anthrone prepared in a separate step, e.g., by hydrogenation . Benzanthrone is best purified by sublimation.
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Yield:82-05-3 98.8%

Reaction Conditions:

Stage #1:9,10-phenanthrenequinone with sulfuric acid;hydrogen;sodium dodecyl-sulfate in chlorobenzene under 10501.1 Torr;Heating;
Stage #2:glycerol with sulfuric acid in chlorobenzeneHeating;Reagent/catalyst;Pressure;

Steps:

1; 2; 3 Example 1
Prepare 21kg of anthraquinone (molecular weight 208.2, 101mol),Ruthenium carbon(With 5% palladium carbon)0.26kg,60% sulfuric acid 0.08kg,Phase transfer catalyst 210g sodium dodecyl sulfate,100kg of chlorobenzene,Put the above materials into a 600L pressure reactor,While breathing H2 gas,Make the pressure in the container reach 1400kPa,Stir for 6.5h at a temperature of 175 ;Cool the reaction solution to 110 ° C,After draining the remaining H2,Filtering the reaction liquid,Then wash with 30L chlorobenzene in batches,The filter cake is used for the recycling of the next batch of catalyst;Then the above chlorobenzene residual liquid and washing liquid,Pour into a 500L clean reactor,Then add glycerol with a concentration of 85%(glycerine) 20.6kg (molecular weight 92.1, 200mol),Heat to 105 ° C while stirring;Control the reaction temperature to 105 120 Add 35.8kg of 85% sulfuric acid(Molecular weight 98, 310mol),After the addition is complete,Continue stirring for 4.5h;After the reaction is completed, the reaction solution is cooled to below 80 ° C,Steam distillation in a 1000L distillation kettle,The vapor phase is condensed to the separator,The upper water returns to the kettle,The lower chlorobenzene collection chlorobenzene intermediate tank is applied to the next batch of reaction; after the chlorobenzene is completely distilled,filter,Collect mother liquor,Wash with hot water until neutral,Unloading,To get the phenanthrone filter cake,Further drying to obtain dry product benzanthrone, the purity is 98.5%, the yield is 98.8%;The mother liquor and the first washing water are collected,After treatment with 0.5 1.5% (mass percentage) activated carbon,Distillation and concentration under reduced pressure,Partially concentrated to sulfuric acid mass concentration of about 60% for the first batch of raw materials for reduction reaction recycling,The remaining part is concentrated to about 80% of sulfuric acid mass concentration,Then use fuming sulfuric acid (104%) or concentrated sulfuric acid (98%) to adjust the sulfuric acid mass concentration to 85% for the second step of condensation feeding.Other washing water is collected for environmental protection and centralized treatment.

References:

Jiangsu Yabang Dyeing Liao Co., Ltd.;Xiong Jun;Tang Xuebin;Zhou Jianbiao CN110668930, 2020, A Location in patent:Paragraph 0031-0043

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