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A biomimetic aqueous heterogeneous catalytic system catalyzes the condensation reaction between aromatic aldehydes and malonate diesters

A malonate diester, heterogeneous catalysis technology, applied in the field of fine chemicals of chemical engineering, can solve the problems of useless value by-products, reduced reaction selectivity, loss of raw materials and products, etc., to achieve saving and full utilization, Improve selectivity and yield, reduce the effect of oxidation

Active Publication Date: 2016-09-14
重庆市化工研究院有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the traditional synthesis method, the condensation reaction of aromatic aldehyde and malonate diester is carried out in a homogeneous base catalyst system. After the reaction, a neutralization operation is required, which will generate a large amount of waste water; because the catalyst is not easy to recycle and use, In the post-treatment process, the loss and waste of raw materials and products are caused, which indirectly causes a waste of energy, and this catalytic system will also cause a variety of side reactions during the reaction process, producing many by-products that are almost useless, resulting in decrease in reaction selectivity

Method used

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  • A biomimetic aqueous heterogeneous catalytic system catalyzes the condensation reaction between aromatic aldehydes and malonate diesters
  • A biomimetic aqueous heterogeneous catalytic system catalyzes the condensation reaction between aromatic aldehydes and malonate diesters
  • A biomimetic aqueous heterogeneous catalytic system catalyzes the condensation reaction between aromatic aldehydes and malonate diesters

Examples

Experimental program
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Embodiment 1

[0044] Embodiment 1 A kind of method that adopts clean technology to synthesize benzoylidene dimethylmalonate comprises the following steps:

[0045] (1) At room temperature, put 50% of the total amount of dimethyl malonate, soluble amino-containing substances, protonic acid, metal salt, and aqueous mixed solvent into the reactor, adjust the pH to 5-6, and , after heating to 30° C., gradually add benzaldehyde or its mixture with the remaining 50% dimethyl malonate. Continue to react at this temperature until the product phase no longer continues to increase;

[0046] (2) From the reaction mixture obtained in step (1), separate out the product-rich phase and the catalyst-containing solvent phase by means of the difference in specific gravity, wherein the solvent phase is recycled;

[0047] (3) The product-rich phase obtained in step (2) is washed with a 1:1 methanol-water solution to remove a small amount of unreacted raw materials to obtain the condensation product dimethyl p...

Embodiment 2

[0048] Embodiment 2 A kind of method that adopts clean technique to synthesize diethyl phenylidene malonate comprises the following steps:

[0049] (1) Put diethyl malonate accounting for 50% of the total amount, amine-containing substances insoluble in solvents, protonic acids, metal salts, and water-containing mixed solvents into the reactor, adjust pH 7 to 8, and simulate sunlight irradiation After heating up to 50°C, gradually add the mixture of benzaldehyde and the remaining 50% diethyl malonate. Continue the reaction at this temperature until the product phase does not continue to increase;

[0050] (2) From the reaction mixture obtained in step (1), use the difference in specific gravity to separate the product-rich phase, solvent phase and solvent-insoluble solid phase containing amine-based substances, and the latter two can be recycled;

[0051] (3) adopt underpressure distillation to the rich product phase that step (2) obtains, to slough a small amount of unreacte...

Embodiment 3

[0052] Embodiment 3 A kind of method that adopts clean technology to synthesize dimethyl benzomalonate comprises the following steps:

[0053] (1) Put all insoluble amine-containing substances, protonic acids, metal salts, aqueous mixed solvents, aromatic aldehydes and dimethyl malonate into the reactor, adjust the pH to 6-7, and heat up to 25 After ℃, maintain this temperature and continue the reaction until the product phase does not continue to increase;

[0054] (2) From the reaction mixture obtained in step (1), use the difference in specific gravity to separate the product-rich phase, the solvent phase and the solid phase amine-containing substance insoluble in the solvent phase, and the latter two can be recycled;

[0055] (3) The product-rich phase obtained in step (2) is washed with 1:1 (volume ratio) methanol-water solution to remove a small amount of unreacted raw materials to obtain the condensation product dimethyl phenylidene malonate or substituted phenylidene ...

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Abstract

The invention discloses a method for catalyzing the condensation reaction between aromatic aldehyde and malonic diester with a bionic water-containing heterogeneous catalytic system. According to the method, aromatic aldehyde and malonic diester are adopted as raw materials. Under illumination, with an amine-containing substance as a catalyst, a Knoevenagel condensation reaction is carried out in a water-containing mixed solvent. After the reaction, a product-rich phase is separated with specific gravity difference, and the solvent and the catalyst can be recycled. The Knoevenagel condensation reaction is a common organic reaction used for producing C=C double bond and synthesizing alpha, beta-unsaturated acids and esters. The most prominent problems in the traditional processes of the reaction are as follows: a homogeneous base catalysis system is adopted, product and raw material separation cost is high, catalyst recycling difficulty is high, product yield is low, and resource waste and environment pollution are caused. According to the invention, the traditional non-recyclable solution catalysis system is replaced by the recyclable catalyst system, the original processes are improved with clean production processes, resources are saved and fully utilized, and environment protection is realized.

Description

【Technical field】 [0001] The present invention relates to the field of fine chemicals in chemical engineering—the preparation method of spices and / or pharmaceutical intermediates, that is, to replace the original process with clean production technology, and at the same time realize resource conservation and full utilization, as well as environmental protection, especially with a An environmentally friendly biomimetic aqueous heterogeneous catalytic system catalyzes the condensation reaction between aromatic aldehydes and malonate diesters. 【Background technique】 [0002] The Knoevenagel condensation reaction (brain Wenger reaction, or Knovenagel condensation reaction, or Konovanog condensation reaction, or Knoevenagel condensation reaction) is to generate a C=C double bond and synthesize α, β- A common method for unsaturated acids and esters is a very important class of organic synthesis reactions. It is widely used in the synthesis of many important fine chemical intermed...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/612C07C69/65C07C67/343
CPCY02P20/584
Inventor 孙波申玉海张春雪吴新世万钧
Owner 重庆市化工研究院有限公司
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