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Method for catalytic synthesis of cinnamic acid by water-soluble calixarene phenolate

A water-soluble, cinnamic acid technology, applied in chemical instruments and methods, catalytic reaction, preparation of carboxylic acid by ozone oxidation, etc., can solve problems such as inability to recycle, difficult separation, and no reports, and achieves the effect of low cost

Inactive Publication Date: 2018-06-15
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the Perkin and Knoevenagel reactions are all prepared under the catalysis of weak bases. The catalyst of Perkin reaction is strong base and weak salt (such as potassium carbonate, potassium acetate, etc.); while the Knoevenagel reaction is catalyzed by weak bases (amines, pyridine, etc.). It is difficult to separate these catalysts from reactants and products and cannot be recycled.
[0007] If the water-soluble calixarene containing sulfonic acid group is treated with alkali, the water-soluble calixarene phenate produced has weak alkalinity, and it is expected to replace the above-mentioned catalyst and be used in weak base-catalyzed reactions. At present, the relevant weakly alkaline water-soluble calixarene The application of aromatic hydrocarbon phenates in catalytic reactions has not been reported yet

Method used

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  • Method for catalytic synthesis of cinnamic acid by water-soluble calixarene phenolate
  • Method for catalytic synthesis of cinnamic acid by water-soluble calixarene phenolate
  • Method for catalytic synthesis of cinnamic acid by water-soluble calixarene phenolate

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Calix[4]arene phenol sodium salt catalyzed Perkin reaction to synthesize cinnamic acid: add freshly distilled benzaldehyde 1.5ml (15 mmol), acetic anhydride 4.0 ml (42 mmol) and 0.69 g calix[4]arene phenol Sodium salt, according to the installation of condenser, thermometer, magnetic stirring. After reacting at 170 °C for 2 h, the catalyst was removed by filtration and washed with 10% Na 2 CO 3 The pH of the solution was adjusted to 9, and the aqueous phase was extracted twice with 10 mL of ethyl acetate. The aqueous phase was filtered with a small amount of activated carbon to absorb impurities, and the filtrate was adjusted to pH = 3 to 4 with concentrated hydrochloric acid. A large number of white crystals were precipitated, filtered with suction, and dried. , weighing, the productive rate is 62.6%.

Embodiment 2

[0024] Calix[6]arene phenol sodium salt catalyzed Perkin reaction to synthesize cinnamic acid: add freshly distilled benzaldehyde 1.5ml (15 mmol), acetic anhydride 4.0 ml (42 mmol) and 1.04g calix[6]arene phenol Sodium salt, install a condenser, a thermometer, and magnetically stir. After reacting at 160 °C for 2 h, the catalyst was removed by filtration and washed with 10% Na 2 CO 3 Adjust the pH of the solution to 9, then extract the water phase twice with 10 mL of ethyl acetate, use a small amount of activated carbon to absorb impurities in the water phase, and filter with suction, adjust the filtrate to pH = 3 to 4 with concentrated hydrochloric acid, and precipitate white crystals, filter with suction, dry, Weighed, the yield was 55.0%.

Embodiment 3

[0026] Calix[8]arene phenol sodium salt catalyzed Perkin reaction to synthesize cinnamic acid: add freshly distilled benzaldehyde 1.5ml (15 mmol), acetic anhydride 5.7 ml (60 mmol) and 1.38g calix[8]arene phenol Sodium salt, equipped with a condenser, a thermometer, and magnetic stirring. The reaction was completed after 2 h at 150 °C, the catalyst was removed by filtration, and 10% Na 2 CO 3 Adjust the pH of the solution to 10, then extract the water phase twice with 10 mL of ethyl acetate, use a small amount of activated carbon to absorb impurities in the water phase, and filter with suction, adjust the filtrate to pH = 3 to 4 with concentrated hydrochloric acid, a large number of white crystals are precipitated, filter with suction, and dry , weighing, the productive rate is 51.5%.

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Abstract

The invention is a method for catalytic synthesis of cinnamic acid by water-soluble calixarene phenolate, belonging to the technical field of preparation of organic compounds. The method comprises thefollowing steps: with the water-soluble calixarene phenolate as a catalyst, allowing the water-soluble calixarene phenolate to catalyze benzaldehyde and acetic anhydride to generate a perkin reaction, or catalyze benzaldehyde and propane diacid to generate a Knoevenagel reaction so as to prepare the cinnamic acid, wherein the calixarene phenolate can be repeatedly utilized for a plurality of times. According to the invention, the calixarene phenolate is calixarene phenolate sodium(possitium) salt which is formed through a reaction of calix[n]arene sulfonic acid (n is equal to 4, 6 and 8) andthiocalix[4]arene sulfonic acid with NaOH, KOH, Na2CO3 and K2CO3; and the usage amount of the calixarene phenolate accounts for 5 to 10% of the mass of the benzaldehyde. In the perkin reaction, the mass ratio of the benzaldehyde to the acetic anhydride is 1: 1 to 1: 4; the temperature of the reaction is 140 to 170 DEG C; and the time of the reaction is 1 to 2 h. In the Knoevenagel reaction, the mass ratio of the benzaldehyde to the propane diacid is 1: 1 to 1: 4; the temperature of the reaction is 120 to 150 DEG C; and the time of the reaction is 1 to 2 h. The process of the reaction does notgenerate three industrial wastes like waste gas, waste water and waste residue and is a green chemical process, so the pollution to the environment is reduced; and after completion of the reaction, the product is easily to be separated from the catalyst. The method provided by the invention has the advantages of simple process, high yield, environmental friendliness and low cost, and is a method applicable to industrial production.

Description

technical field [0001] The invention relates to the field of organic catalysis, and specifically uses water-soluble calixarene phenoxide as a catalyst to catalyze the synthesis of cinnamic acid. Background technique [0002] The invention relates to a catalytic reaction of water-soluble calixarene phenate. [0003] Calixarenes are a class of macrocyclic oligomers formed by linking the 2 and 6 positions of multiple phenols through methylene groups. The phenolic hydroxyl group of calixarene and its para-position can introduce various functional groups to prepare a variety of calixarene derivatives, making it more widely used. However, calixarenes are insoluble in water and are limited in certain chemical reactions. Chemical modification of its upper and lower edges can improve its water solubility and expand the application range of calixarene. In 1984, the first case of preparation of water-soluble calixarene derivatives was reported: Arduini A, Pochini A, Reverberi A, et ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/083C07C51/38C07C57/44B01J31/02
CPCB01J31/0229B01J2231/4205C07C51/083C07C51/38C07C57/44
Inventor 陈平张国良
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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