Method for synthesizing azelaic acid through single ionic liquid catalyzing oleic acid

A technology for ionic liquids and catalyzed oleic acid, which is applied in chemical instruments and methods, preparation of organic compounds, catalytic reactions, etc., can solve the problems of residual liquid pollution, ozone explosion, short reaction time, etc., and achieve environmental friendliness, reaction Increased speed and easy separation

Inactive Publication Date: 2015-12-30
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent No. 200710042766.6 discloses a method for preparing azelaic acid catalyzed by a solid acid catalyst. The method is characterized by a short reaction time and no pollution to the oxidant; the disadvantage is that there is a two-phase reaction between solid and liquid, and a phase transfer reagent needs to be added. polluted environment
Patent No. 200610029216.6 discloses a method for preparing azelaic acid by catalytic oxidation of an ozone-hydrogen peroxide mixed oxidant. The advantage of this method is that there is no solid reactant; the disadvantage is that two-step reactions are required, and ozone is prone to explosion when reacting at high temperature. And it is a two-phase reaction of gas and liquid, and it is also necessary to add a phase transfer reagent, and the residual liquid of the reaction will pollute the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Synthesis of 1-(α-acid)methyl-3-methylimidazolium phosphotungstic acid ionic liquid catalyst: 3 g of N-methylimidazole and 3 g of ethyl chloroacetate were dissolved in 10 mL of absolute ethanol, and the Fully react under the conditions to obtain the ionic liquid intermediate, take 3 grams of the above-mentioned ionic liquid intermediate and 20 mL of concentrated hydrochloric acid with a mass fraction of 37% and add it to 10 mL of acetonitrile solution, then add 3 grams of phosphotungstic acid, and react at room temperature for 24 hours to obtain 1-(α-acid)methyl-3-methylimidazolium phosphotungstic acid ionic liquid.

[0015] In a 500mL four-neck flask equipped with an electromagnetic stirrer, a thermometer, and a condenser tube, 50 grams of oleic acid and 5 grams of 1-(α-acid) methyl-3-methylimidazolium phosphotungstic acid ionic liquid catalyst were added. Quickly stir and heat to 70°C, add 200ml of hydrogen peroxide with a mass concentration of 20%, and react for 1 ho...

Embodiment 2

[0017] The synthetic method of 1-(alpha-acid) methyl-3-methylimidazolium phosphotungstic acid ionic liquid catalyst is the same as that in Example 1.

[0018] In a 500mL four-neck flask equipped with an electromagnetic stirrer, a thermometer, and a condenser tube, 50 grams of oleic acid and 5 grams of 1-(α-acid) methyl-3-methylimidazolium phosphotungstic acid ionic liquid catalyst were added. Quickly stir and heat to 85°C, add 200ml of hydrogen peroxide with a mass concentration of 30% in batches, and react for 4 hours. After the reaction, put the mixed solution in a separatory funnel for separation. top, easy to separate. The separated aqueous phase was refrigerated and crystallized at 0°C, a white powder was precipitated, and the calculated yield was about 87.01%. The melting point is 105.5-107.0°C.

Embodiment 3

[0020] The synthetic method of 1-(alpha-acid) methyl-3-methylimidazolium phosphotungstic acid ionic liquid catalyst is the same as that in Example 1.

[0021] In a 500mL four-neck flask equipped with an electromagnetic stirrer, a thermometer, and a condenser tube, 50 grams of oleic acid and 5 grams of 1-(α-acid) methyl-3-methylimidazolium phosphotungstic acid ionic liquid catalyst were added. Quickly stir and heat to 95°C, add 200ml of hydrogen peroxide with a mass concentration of 50% in batches, and react for 6 hours. After the reaction, put the mixed solution in a separatory funnel for separation. separate. The separated aqueous phase was refrigerated and crystallized at 5°C, a white powder was precipitated, and the calculated yield was about 91.01%. The melting point is 104.5-106.0°C.

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Abstract

The invention relates to a method for synthesizing azelaic acid through single ionic liquid catalyzing oleic acid. The method comprises the following steps: oleic acid and a 1-(alpha-acid) methyl-3-methylimidazole phosphotungstic acid ionic liquid catalyst are mixed, then a hydrogen peroxide solution is added, the mixture is fully stirred, after the reaction, an oil layer is on the upper layer, a water lay is on the lower layer, and separation is easy; a separated aqueous phase is refrigerated and crystallized, white powder is precipitated, and azelaic acid solid is obtained through suction filtration and drying. According to the method, other chemical apparatuses are not required to be added in the whole reaction process, energy is saved, the reaction speed is accelerated, the time is saved, and no large number of organic solvent is required in the reaction, so that the method is green and environment-friendly. The method for synthesizing azelaic acid through single ionic liquid catalyzing oleic acid has the advantages that the reaction yield is high, one step reaction process is simple, the reaction system is easy to separated, the production cost is effectively reduced, and environment is protected.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a method for synthesizing azelaic acid from oleic acid by a single ionic liquid, that is, using oleic acid, hydrogen peroxide as an oxidant, and an ionic liquid as a catalyst without adding a phase transfer reagent to oxidize the oil A method for the synthesis of azelaic acid. Background technique [0002] Azelaic acid can be used as a raw material for spices, lubricating oils, oils, polyamide resins and for alkyd resins, paints and chemical synthesis. Most of azelaic acid is used to produce dioctyl azelate (DOZ) plasticizers . [0003] The preparation of azelaic acid and pelargonic acid by oxidizing oleic acid with hydrogen peroxide is the main method of synthesizing azelaic acid and pelargonic acid at present. Patent No. 200710042766.6 discloses a method for preparing azelaic acid catalyzed by a solid acid catalyst. The method is characterized by a short...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/285C07C55/18B01J31/18
CPCB01J31/0285B01J2231/70C07C51/285C07C55/18Y02P20/10
Inventor 史春薇薛瑞赵杉林陈平仲崇民宋锦玉王亚新
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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