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Acetylene even-coupling method under temperate condition

A terminal alkyne and coupling technology, which is applied in the field of preparation and recovery of LDHs catalysts, can solve the problems of no literature reports and limited literature, and achieve good economic benefits, low requirements, and mild reaction conditions.

Inactive Publication Date: 2008-07-09
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the number of literatures on copper-containing hydrotalcites is limited, and there are no reports on the homocoupling reaction of terminal alkynes catalyzed by hydrotalcites.

Method used

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  • Acetylene even-coupling method under temperate condition
  • Acetylene even-coupling method under temperate condition
  • Acetylene even-coupling method under temperate condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Taking the preparation of NiAl-LDH catalyst as an example, the preparation of hydrotalcite catalyst adopts coprecipitation method. Ni(NO 3 ) 2 6H 2 O and Al(NO 3 ) 3 9H 2 O by Ni + / Al 3+ The molar ratio is 3:1 to form a solution, and the 3M NaOH solution is used as a coprecipitant. The above two solutions are added dropwise to the stirring 0.5M NaOH solution at a rate of 1 drop per second. 2 CO 3 In the solution, the pH of the solution was controlled to be 10, and the solution was aged in an oil bath at 65° C. for 18 hours. The reaction solution was filtered, the solid was washed with distilled water, and then dried in an oven at 80° C. for 12 hours to prepare the corresponding NiAl-LDH catalyst.

[0027] The reaction formula with phenylacetylene as the reaction substrate is as follows:

[0028]

[0029] Weigh 0.204g (2.0mmol) of the reaction substrate phenylacetylene, 0.464g (4.0mmol) of TMEDA, and 0.56g of NiAl-LDH catalyst, and place them in a glass fla...

Embodiment 2

[0031] Weigh 0.204g (2.0mmol) of the reaction substrate phenylacetylene, 0.232g (2.0mmol) of TMEDA, and 0.36g of CuCr-LDH catalyst, and place them together in a glass flask, add 10mL of organic solvent ethyl acetate, and The reaction was stirred for 12 hours. After the reaction was completed, the reaction mixture solution in the flask was filtered. The filtered solid was washed 2-3 times with ethyl acetate, then dried at 80° C. for 6 hours, and directly used for the next catalytic cycle. The filtrate was combined with the washed solvent, concentrated with a rotary evaporator, and then separated through a silica gel column, and the eluent was n-hexane / ethyl acetate to obtain the yield of 1,4-diphenyl-1,3-butadiyne 16%.

Embodiment 3

[0033]Weigh 0.204g (2.0mmol) of the reaction substrate phenylacetylene, 0.24g (3.0mmol) of pyridine, and 0.15g of CuAl-LDH catalyst, and place them together in a glass flask, add 10mL of organic solvent acetone, and stir the reaction at normal temperature and pressure 10 hours. After stopping the reaction, the reaction mixture solution in the flask was filtered. The filtered solid was washed 2-3 times with acetone, then dried at 80° C. for 6 hours, and directly used for the next catalytic cycle. The filtrate was combined with the washed solvent, concentrated with a rotary evaporator, and then separated through a silica gel column, and the eluent was n-hexane / ethyl acetate to obtain the yield of 1,4-diphenyl-1,3-butadiyne was 67%.

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Abstract

The invention discloses the method of end-alkynes coupling, using end-alkynes as raw material, and using hydrotalcite as accelerating agent. The accelerating agent uses double hydroxy compound of divalent transient metal ion and tervalent transient metal ion as plywood, and uses carbonate or nitrate anion as layer-to-layer negative ion. The reaction condition is normal temperature and normal pressure, the product is 1, 3-alkynyl compound, and the divalent transient metal positive ion possesses the particular accelerating effect. The method has the advantages of good catalytic activity, short reaction time, mild reaction condition, simple operation, low cost and no environmental pollution.

Description

technical field [0001] The invention relates to a method for synthesizing 1,3-diyne compounds by homocoupling of terminal alkynes under mild conditions (at room temperature and in air), in particular to a method for preparing and recovering LDHs catalysts. Background technique [0002] Glaser used phenylacetylene as raw material for the first time in 1869, used ammonia and ethanol as solvent, copper salt (CuCl) as catalyst, and successfully synthesized 1,3-diyne in the presence of air. This type of reaction is called Glaser The coupling reaction is also called the homo-coupling reaction of terminal alkynes (Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2422.). In 1962, Hay made important improvements to the reaction. He used CuCl and tetramethylethylenediamine (TMEDA) as catalysts, and successfully used O in solvents such as acetone or o-dichlorobenzene 2 Diacetylenes were synthesized by oxidation of terminal alkynes (Hay, A.S.J. Org. Chem. 1962, 27, 3320.). Since then, this rea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C2/38C07C11/22B01J21/10B01J23/72B01J23/755B01J23/745B01J23/75B01J21/02
Inventor 朱冰春姜玄珍
Owner ZHEJIANG UNIV
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