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Method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion

An alkyl salicylate and ionic liquid technology, applied in the field of organic compound preparation, can solve the problems of complex process, unfriendly environment, long reaction time, etc., and achieve the realization of catalytic process, convenient separation and recovery, high catalytic activity Effect

Inactive Publication Date: 2011-03-16
ZHENJIANG GAOPENG PHARMA
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  • Abstract
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Problems solved by technology

[0004] The technical problem to be solved by the present invention is: in order to overcome the disadvantages of the known synthesis method, such as complex process, unfriendly environment, and long reaction time, a kind of ionic liquid containing pyridine functional group under the promotion of microwave is provided to catalyze the synthesis of salicylic acid alkyl A new approach to esters
This synthetic method conforms to the principles of green chemistry

Method used

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  • Method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion
  • Method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion
  • Method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion

Examples

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Effect test

example 1

[0027] Example 1: Add 0.02mol salicylic acid and 0.06mol methanol (the molar ratio of salicylic acid to methanol is 1:3) into a microwave-specific reaction vessel, add 10mmol of ionic liquid [PSPy][HSO 4 ], stirred and dissolved, and placed in a microwave-assisted synthesizer to react; set the reaction temperature to 105°C, the rated power to 1360W, and the radiation time to 20min. After the reaction, the upper layer of the system is methyl salicylate, and the product and unreacted salicylic acid can be separated from the system by ether extraction. The conversion rate of salicylic acid was 93.7%, and the selectivity of methyl salicylate was 99.9%. The ionic liquid in the lower layer was dried in a blast drying oven at 90°C for 6 hours, and then the substrate was added, and the reaction could be repeated 8 times as above. The reaction results are shown in Table 1.

[0028] Table 1 The relationship between catalyst use times and catalytic activity

[0029]

example 2

[0030] In Example 2, except that the molar ratio of salicylic acid and methanol in the raw material was changed to 1:2, other experimental conditions and ionic liquid were the same as in Example 1 to prepare methyl salicylate. The conversion rate of salicylic acid was 81.3%, and the selectivity of methyl salicylate was 99.9%.

example 3

[0031] In Example 3, except that the amount of the ionic liquid in the reaction condition was changed to 8 mmol, other experimental conditions and ionic liquid were the same as in Example 1, and methyl salicylate was prepared. The conversion rate of salicylic acid was 82.2%, and the selectivity of methyl salicylate was 99.9%.

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Abstract

The invention belongs to the technical field of preparation of organic compounds and relates to a method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion. The method is carried out according to the following reaction formula and comprises the following steps: (1) adding salicylic acid and fatty alcohol into a microwave special reactor according to the amount-of-substance ratio of 1:2-3, further adding the ionic liquid, stirring and dissolving, wherein the reaction temperature is 85-115 DEG C, the rated power is 1360W, and the microwave radiation time is 15-30min; the fatty alcohol is methanol, ethanol, n-butanol, n-pentanol, n-hexanol or n-octanol; the ionic liquid is (PSPy) (HSO4), (PSPy) (H2PO4), (PSPy) (pTSA), (BSPy) (HSO4), (BSPy) (H2PO4) or (PSPy) (pTSA); and the amount-of-substance ratio of the ionic liquid to the salicylic acid is 0.4-0.6:1; and (2) cooling reactants to room temperature, adding ethyl ether for dissolving the salicylic acid which is not reacted and reaction products, and pouring and separating the ionic liquid; and placing in an air blowing drying box for drying for 6h at 90 DEG C, and being directly used for the next reaction. The synthesis process is simple and easy to operate, and the used ionic liquid has no environmental pollution and can be recycled.

Description

[0001] Technical field: the invention belongs to the technical field of organic compound preparation, and relates to a method for catalyzing and synthesizing an important intermediate salicylate of medicines, pesticides, spices and coatings under the promotion of microwaves. Background technique: [0002] Alkyl salicylate is an important class of chemical products, which are widely used in food preservatives, solvents, spices, intermediates, pharmaceuticals, plasticizers, cosmetics and other chemical fields. Fisher esterification is the easiest way to obtain this organic ester, however these reactions usually use some liquid inorganic acids as catalysts, such as sulfuric acid, phosphoric acid, hydrofluoric acid, etc. As we all know, these liquid inorganic acids have many disadvantages: such as corrosion of equipment, many by-products, difficulty in recycling and reuse, and pollution of the environment. There are also many reports on the use of solid acid catalysts. "React.Fun...

Claims

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Application Information

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IPC IPC(8): C07C69/84C07C67/08B01J31/02B01J19/12
Inventor 王志高李华明时花闫永胜朱文帅黄卫红
Owner ZHENJIANG GAOPENG PHARMA
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