Application of sludge carbon catalyst with modified surface

A technology of surface modification and sludge charcoal, which is applied in the direction of physical/chemical process catalysts, non-central analgesics, anti-inflammatory agents, etc., can solve problems such as no relevant literature reports, and achieve good yield, simple preparation, The effect of a wide range of sources

Active Publication Date: 2018-11-27
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, surface-modified sludge charcoal is used as a catalyst to realize the construction of C-O bond through the formation of metal carbene and O-H insertion reaction. The one-step reaction to generate α-(phenoxy)acetate derivatives has not been reported in relevant literature. Very innovative, providing a new idea for the selection of catalysts in organic synthesis

Method used

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  • Application of sludge carbon catalyst with modified surface
  • Application of sludge carbon catalyst with modified surface
  • Application of sludge carbon catalyst with modified surface

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0032] Catalyst preparation: Sludge from a sewage treatment plant in Dalian, China, was dried in a muffle furnace at 105 °C to constant weight, and heated to 600°C, continue carbonization for 4 hours, and when the temperature in the furnace drops to room temperature, the carbonaceous material (SW) derived from sewage sludge can be obtained. In order to change the surface activity of SW, different acids were used to treat SW. During acid treatment, by mixing carbonized SW with the same volume of HCl (20.5 wt%), HClO 4 (35.4wt%), H 2 SO 4 (63.4wt%) and HNO 3 (40.5wt%) were impregnated for 24 hours to prepare 50 mL of different acid-treated SWs. Then, wash SW-HCl and SW-HClO with deionized water, respectively 4 、SW-H 2 SO 4 and SW-HNO 3 Until the pH of the washing liquid reaches 6-7, the solid is recovered and dried at room temperature to obtain the corresponding acid-treated surface-modified sludge carbon catalyst SW-HCl, SW-HClO 4 、SW-H 2 SO 4 and SW-HNO 3 . Note: ...

Embodiment 1

[0036] Embodiment 1 (catalyst in the following examples refers to the preparation of catalyst in claim 3)

[0037]

[0038] At room temperature, weigh ethyl phenyldiazoacetate 1a (0.5mmol), p-bromophenol 2a (0.70mmol), SW-HClO 4 (50mg) into a dry and clean 25mL Schlenk reaction tube, under air atmosphere, add 5mL of 1,2-dichloroethane, stir at room temperature for 2-5 minutes, and transfer to an oil bath magnetic stirring heater at 70°C Reacted for 24 hours, TLC detected that the raw material had reacted completely, stopped the reaction, the reaction solution was cooled to room temperature, suction filtered, the filter cake was washed with dichloromethane until the filtrate was colorless, concentrated under reduced pressure to remove volatile components, and separated by silica gel column chromatography ( Eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1), the target product 3a (104mg, yield 62%) was obtained as colorless, transparent and viscous, and the target pro...

Embodiment 2

[0039] Embodiment 2 (comparative example: different catalyst contrasts)

[0040]

[0041] At room temperature, successively weigh ethyl phenyldiazoacetate 1a (0.5mmol), p-bromophenol 2a (0.70mmol), SW-HCl (50mg) in a dry and clean 25mL Schlenk reaction tube, under air atmosphere , add 5 mL of 1,2-dichloroethane, stir at room temperature for 2-5 minutes, transfer to an oil bath magnetic stirring heater at 70°C and react for 24 hours, TLC detects that the raw materials have reacted completely, stop the reaction, and remove the reaction solution Cool to room temperature, filter with suction, wash the filter cake with dichloromethane until the filtrate is colorless, concentrate under reduced pressure to remove volatile components, and separate by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1), the target product 3a (35 mg, yield 21%) was obtained as a colorless, transparent and viscous product, which was confirmed by NMR and GC-MS c...

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Abstract

The invention discloses application of a sludge carbon catalyst with a modified surface in reaction of inserting O-H into carbene and constructing a C-O bond. Alpha-diazonium ester and a phenolic compound serve as starting materials, modified sludge carbon treated by perchloric acid serves as a catalyst, the construction of the C-O bond is achieved by forming metal carbene to complete O-H insertion under the conditions of heating and air atmosphere, and an alpha-(phenoxy)acetate derivative is generated in one step. The catalyst is prepared by sludge remaining after municipal sewage treatment,and has the advantages of having a wide source, being prepared easily, having low cost, and being green and environmentally friendly; the reaction raw materials are easy to obtain, the conditions aremild, the yield is good, the gram-scale reaction can be achieved, the catalyst has an industrial prospect, the reuse of waste is achieved, and the purpose of green environmental protection and green chemistry is achieved.

Description

technical field [0001] The invention relates to the application of a surface-modified sludge carbon catalyst in O-H insertion reaction and construction of C-O bond. Using α-diazo esters and phenolic compounds as starting materials, the improved sludge charcoal catalyst treated with perchloric acid can realize the construction of C-O bond through the formation of metal carbene and N-H insertion reaction under heating conditions and in air atmosphere. A one-step reaction produces α-(phenoxy)acetate derivatives. [0002] Compared with the reported synthesis methods of α-(phenoxy) acetate derivatives, the present invention avoids the use of transition metal catalysts and selects sludge charcoal from a wide range of sources as the catalyst, which is easy to prepare, low in cost and environmentally friendly; The reaction raw materials are easy to obtain, the conditions are mild, and the yield is good (up to 85% of the separation yield). It can realize the gram-scale reaction and ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/736B01J27/06B01J35/10A61P29/00
CPCA61P29/00B01J27/06B01J35/10C07C67/31C07C69/736
Inventor 黄菲张志朋黄和于杨易享炎乔纳森贝尔
Owner NANJING UNIV OF TECH
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