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Method for ozonization preparation of 2-nonenyl aldehyde

A nonenal and ozonation technology, which is applied in the field of ozonation to prepare 2-nonenal, can solve problems such as harsh implementation conditions, difficulty in large-scale production, and unsafety, and achieve rapid response, simple reaction process, and high yield Effect

Inactive Publication Date: 2011-09-28
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction process requires low temperature and harsh implementation conditions. The reducing agent dimethyl sulfide used is a liquid with low boiling point and toxicity, which is unsafe and difficult to carry out large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] a. Add 50 g of ricinoleic acid methyl ester to a mixed solution of 50 g of acetic acid and 200 g of n-hexane, stir evenly, and pass O at 0°C 3 / O 2 Mixed gas (the mass percent of ozone is 3.3%) is oxidized, and time 2 hours, ricinoleic acid methyl ester is oxidized to ozonide;

[0032] b. At room temperature, slowly add the ozonide in step a to 100ml of NaHSO 3 In the aqueous solution (its mass percentage is 5%), the temperature is raised to 50°C for reduction and decomposition, and the ozonide is reduced to 3-hydroxynonanal for 1 hour;

[0033] c. After the reduction reaction, lower the temperature to 30°C, adjust the pH to 9 with sodium hydroxide solution, transfer the reaction solution to a separatory funnel and let it stand for stratification, separate the water layer, and use a non-ionic Wash to neutral;

[0034] d. Add 2ml of dilute sulfuric acid (3% by mass) into the organic phase obtained in step c to reflux for 2 hours, and dehydrate 3-hydroxynonanal to 2-no...

Embodiment 2

[0037] a. Add 50 g of ricinoleic acid methyl ester to a mixed solution of 100 g of acetic acid and 150 g of n-hexane, stir evenly, and pass O at 8°C 3 / O 2 Mixed gas (the mass percent of ozone is 3.3%) is oxidized, and time 3 hours, ricinoleic acid methyl ester is oxidized to ozonide;

[0038] b. At room temperature, slowly add the ozonide in step a to 150ml of NaHSO 3 In the aqueous solution (mass percentage is 8%), the temperature is raised to 60° C. for reduction and decomposition, and the time is 2 hours, and the ozonide is reduced to 3-hydroxynonanal;

[0039] c. After the reduction reaction, lower the temperature to 30°C, adjust the pH to 10 with sodium hydroxide solution, transfer the reaction solution to a separatory funnel and let it stand for stratification, separate the water layer, and use a non-ionic Wash to neutral;

[0040] d. Add 5ml of dilute sulfuric acid (4% by mass) into the organic phase obtained in step c to reflux for 3 hours, and dehydrate 3-hydroxyn...

Embodiment 3

[0043] a. Add 55 g of ricinoleic acid methyl ester to the mixed solution of 55 g of acetic acid and 250 g of n-hexane, stir evenly, and pass O at 17°C 3 / O 2 Mixed gas (mass percentage of ozone is 3.3%) is oxidized, and time 4 hours, ricinoleic acid methyl ester is oxidized to ozonide;

[0044] b. At room temperature, slowly add the ozonide in step a to 200ml of NaHSO 3 In the aqueous solution (mass percentage is 15%), the temperature is raised to 65° C. for reduction and decomposition, and the time is 2.5 hours, and the ozonide is reduced to 3-hydroxynonanal;

[0045]c. After the reduction reaction, lower the temperature to 30°C, adjust the pH to 10 with sodium hydroxide solution, transfer the reaction solution to a separatory funnel and let it stand for stratification, separate the water layer, and use a non-ionic Wash to neutral;

[0046] d. Add 7ml of dilute sulfuric acid (5% by mass) into the organic phase obtained in step c to reflux for 3.5 hours, and dehydrate 3-hyd...

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Abstract

The invention relates to a method for preparing 2-nonenal by ozonization with castor methyl oleate as the raw material, ethanol and n-hexane as the solvent, comprising performing ozonization by ventilating O3 / O2 gas mixture after uniformly mixing the raw material and the solvent at the low temperature, slowly dropping aqueous solution of NaHSO3 in ozonides, raising temperature for reductive decomposition, regulating the pH to 9-11 by sodium hydroxide solution, setting the mixture aside for layering, removing the water layer, rinsing the organic phase to neutrality by de-ionized water, adding dilute sulphuric acid for reflux, and recovering solution through reduced pressure distillation, and obtaining the target product, 2-nonenal, through the molecular distillation of the reaction mixture. In the method, no high pressure is needed during the reaction; the solvent of n-hexane can be recovered for repeated use; the mixed solvent system solves the serious corrosion to the devices by using acetic acid as solvent; the method has clean process, environmental protection, safe execution, simple operation and convenient mass production. The separation and purification of the products are simple.

Description

technical field [0001] The present invention relates to the method for preparing 2-nonenal by ozonation, especially with NaHSO 3 Aqueous solution is used as a reducing agent to reduce the method of cracking ozonide. Background technique [0002] 2-Nonenal is an interesting flavoring, light yellow oily liquid, molecular formula C 9 h 16 O, molecular weight 140.23, boiling point 88-90°C / 12mmHg, relative density 0.846 (20°C), refractive index 1.4531 (20°C), slightly soluble in water, soluble in organic solvents. This aldehyde exists in trace amounts in volatiles such as apricot, rice, popcorn and narcissus, and it is the main component in the fragrance of cucumber. It exhibits very good aroma and aroma characteristics at very low concentrations, and can be added to natural or synthetic flavoring foods, such as meat, coffee and other beverages, to improve or enhance the aroma properties, making the aroma and aroma of food better than natural products It is also thick, and is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/21C07C45/66C07C45/41C07C45/54C11B9/00
Inventor 吾满江·艾力艾买提江·萨伍提司马义·努尔拉努尔买买提·阿布都克力木
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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