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Method for producing nonandioic acid, pelargonic acid by ozonization-oxidative decomposition of oleic acid

A technology of oxidative decomposition and ozonation, applied in the preparation of carboxylic acid by ozone oxidation, organic chemistry, etc., can solve the problems of severe solvent loss, reduced yield of azelaic acid, complicated separation and purification process, etc., to achieve convenient separation Effect of purification process, reduction of self-decomposition, and improvement of reaction efficiency

Active Publication Date: 2011-09-14
SICHUAN SIPO CHEMICAL CO LTD
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  • Summary
  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

However, the existing oleic acid ozonation process needs to use a catalyst, and the subsequent separation and purification process is complicated and the production cost is high; and the solvents used in the existing process are nucleophilic solvents such as glacial acetic acid, formic acid or nonanoic acid, and The self-decomposition rate of acid ozonide in this type of solvent is faster, and the self-decomposition of oleic acid ozonide will produce ketoacid (ketoacid), which will not only reduce the yield of product azelaic acid, but also make the product unsafe because of its ketoacid content exceeding the standard. Cannot meet the quality requirements (the content index of keto acid in azelaic acid is required to be below 0.05)
The use of glacial acetic acid or formic acid as a solvent also has the following disadvantages: First, the corrosion resistance of the reaction equipment, wetted parts, pipelines, pumps, etc. need to be considered, which requires high equipment, especially electronic grade azelaic acid products , the iron ion and chloride ion in azelaic acid are all required to be below 2ppm. For the use of such a reaction solvent, it is difficult to meet this requirement if conventional equipment is used; Oxygen source, the dew point of the gas before entering the ozone generator is usually below -45°C, and the dryness is very high. After the prepared ozonated gas enters the reactor, it contacts with the solvent in the reaction system, and the gas-liquid two-phase transmission occurs. quality, a large amount of solvent is entrained by the gas, and the loss of solvent in the reaction system will be very severe

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] With 300kg oleic acid (the actual content of oleic acid is 76%, linoleic acid 12%), 500kg of C 2 ~C 9 Monobasic saturated fatty acids (containing 45% nonanoic acid, 35% caproic acid, and the rest are other C 2 ~C 9 monobasic saturated fatty acid) mixed, and the ozonated gas with an ozone content of 2.5% is introduced, and the gas flow rate is 450m 3 / h, co-flow into the static mixing reactor, control the temperature of the reaction system to react at 30 ° C, until the ozone content in the ozonated gas introduced is consistent with the ozone content in the ozonated tail gas exiting the reaction system, and the ozone reaction is terminated to obtain Oleic acid ozonide; transfer the ozonide to the oxidation reactor, and the flow rate to the reaction system is 15-25m 3 Oxygen per hour, control the reaction temperature at 60-120°C, stir, react for 4.5 hours, take samples at intervals of 0.5 hours, use gas chromatography to analyze the composition of the oxidation solution...

Embodiment 2

[0017] 300kg vegetable oil is hydrolyzed to generate mixed fatty acids containing oleic acid and linoleic acid (the actual content of oleic acid is 73%, linoleic acid 12%), 350kg of C 2 ~C 9 Monobasic saturated fatty acids (containing 50% nonanoic acid, 30% caproic acid, and the rest are other C 2 ~C 9 monobasic saturated fatty acid) mixed into the ozonation reactor, mixed, stirred, the ozone content of 2.5% into the ozonated gas, gas flow control at 450m 3 / h, control the temperature of the reaction system at 33°C, react for 5.5h, transfer the generated ozonide to an oxidation reactor equipped with 120kg of monobasic saturated fatty acid solvent, the reaction system is ventilated with oxygen, and the flow rate is 15-25m 3 / h, the temperature is controlled at 60-120°C, stirring; after the reaction for 5 hours, the composition of the oxidation solution is sampled and analyzed at intervals of 30 minutes, and the reaction is terminated when the content of azelaic acid no longer...

Embodiment 3

[0019] 300kg animal fats are hydrolyzed to generate mixed fatty acids containing oleic acid and linoleic acid (the actual content of oleic acid is 45%, linoleic acid 10%), 300kg of C 2 ~C 9 Monobasic saturated fatty acids (containing 55% nonanoic acid, 25% caproic acid, and the rest are other C 2 ~C 9 monobasic saturated fatty acid) into the ozonation reactor, mix well, stir, pass into ozonation gas with an ozone content of 4%, control the temperature of the reaction system at 40°C, and react for 3.5h; In the oxidation reactor of non-nucleophilic solvent, the reaction system is ventilated with oxygen, and the oxygen flow rate is controlled at 15-25m 3 / h, control the temperature of the reaction system at 60-120°C, stir, after 3 hours of reaction, take samples and analyze the composition of the oxidation solution at intervals of 0.5 hours, stop the reaction when the content of azelaic acid no longer increases, and obtain The mixture of 748kg, wherein, nonanoic acid 290kg, az...

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PUM

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Abstract

The present invention discloses a method for preparing azelaic acid and pelargonic acid, which comprises the following steps: oleic acid and non-nucleophilic solvent are mixed, and then takes the ozonizing reaction in a static mix reactor; the oleic acid ozonide obtained from the reaction is taken oxidation reaction, and oxidation product mixture with azelaic acid and pelargonic acid is obtained; low carbon dibasic acid in the oxidation product mixture is eliminated by distillation method; high carbon dibasic acid is eliminated by fractionation, and azelaic acid and pelargonic acid are obtained. The method for preparing azelaic acid and pelargonic acid has ozone as oxidant, adopts the mixing monocarboxylic acid organic acid of C2-C9 as solvent, co-flows with oleic acid to react in the static mixing reactor, has high reaction efficiency and safety, and can reduce keto acid content in product when azelaic acid yield is improved; ozonide adopts oxygen to oxidize and decompose, with no introduction of other chemical reagent, which can simplify subsequent separation and purification technique and reduce the pollution towards environment; the reaction system is carried out in normal pressure, with mild condition, low requirement for the equipment and low production cost.

Description

technical field [0001] The invention relates to a method for preparing an organic acid, in particular to a method for preparing azelaic acid and pelargonic acid by ozonation-oxidative decomposition of oleic acid. Background technique [0002] Both azelaic acid and nonanoic acid are important fine chemical intermediates, and their industrial uses are very extensive. The industrial use of azelaic acid is mainly for the production of azelaic acid plasticizers, and secondly for the synthesis of fragrances, lubricating oils and polyamides. In addition, it can also be used for the manufacture of electrolytic capacitors, skin protection and skin protection. disease treatment. Nonanoic acid is a by-product of the production of azelaic acid. Nonanoic acid is widely used in the field of plastics and spices, and can be used to produce nonanoic acid ester plasticizers, paint dryers, and food flavors. [0003] At present, the production methods of azelaic acid include the oxidation of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/34C07C55/18C07C53/126
Inventor 朱进杜俊超周一民谢小俊
Owner SICHUAN SIPO CHEMICAL CO LTD
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