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Method for preparing octanohydroxamic acid

A technology for octanoyl hydroxamic acid and octanoyl hydroxamic acid methyl ester, which is applied in the field of preparation of octanoyl hydroxamic acid, can solve problems such as low economic value, and achieve the effects of good purity, low cost and simple operation

Inactive Publication Date: 2017-04-26
禹城禹圳生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The production processes of the prior art all use hydroxylamine hydrochloride or hydroxylamine sulfate as the main raw material, and generate hydroxylamine under the action of sodium hydroxide with more than twice the equivalent, and further undergo hydroximation reaction with methyl octanoate or ethyl ester, acidify The main product caprylyl hydroxamic acid is processed, and a large amount of sodium chloride or sodium sulfate is produced correspondingly, but the economic value of the above-mentioned by-products is low, so there is an optimization need to further innovate the preparation process and improve the overall process value

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] At 0-10°C, add 44g of sodium hydroxide (1.1mol) in batches to a reaction flask containing 53g of hydroxylamine nitrate (0.55mol) and 200mL of methanol, and continue the reaction for 30 minutes after all the sodium hydroxide has been added. , 79g methyl octanoate (0.5mol) was added dropwise into the reaction flask within 30 minutes, then the temperature was raised to 50° C., and the reaction was carried out for 2 hours. After the reaction, cool down to room temperature, filter to obtain sodium nitrate as a by-product, then distill off methanol (GC shows a small amount of octanoic acid methyl ester), lower the temperature to 0°C, then slowly add 5% nitric acid dropwise to adjust the pH value to 3-4 , precipitated solid, filtered, and the filter cake was dried to obtain octanoylhydroxamic acid 67g, yield 84%, 1 H NMR (DMSO-d6,400MHz): δ10.33(br,1H),8.64(br,1H),1.92(t,2H),1.54-1.41(m,2H),1.34-1.15(m,8H) ,0.86(t,3H). The filtrate was separated to obtain 3g of oil, 1 H NMR...

Embodiment 2

[0019] At 0-10°C, add 40g of sodium hydroxide (1.0mol) in batches to a reaction flask containing 48g of hydroxylamine nitrate (0.5mol) and 200mL of methanol, and continue the reaction for 30 minutes after all the sodium hydroxide is added. , 79g methyl octanoate (0.5mol) was added dropwise into the reaction flask within 30 minutes, then the temperature was raised to 50° C., and the reaction was carried out for 2 hours. After the reaction is finished, cool down to room temperature, filter to obtain the by-product sodium nitrate, then distill off methanol (GC shows methyl octanoate), lower the temperature to 0°C, then slowly add 5% nitric acid dropwise, adjust the pH value to 3-4, The solid was precipitated, filtered, and the filter cake was dried to obtain 61 g of octanoylhydroxamic acid, with a yield of 77%; the filtrate was separated to obtain 2.1 g of an oil, 1 H NMR identified it as n-octanoic acid; the remaining aqueous phase was concentrated to obtain solid sodium nitrate...

Embodiment 3

[0021] At 0-10°C, add 50g of sodium hydroxide (1.25mol) in batches to a reaction flask containing 72g of hydroxylamine nitrate (0.75mol) and 200mL of methanol, and continue the reaction for 30 minutes after all the sodium hydroxide is added. , 79g methyl octanoate (0.5mol) was added dropwise into the reaction flask within 30 minutes, then the temperature was raised to 50° C., and the reaction was carried out for 2 hours. After the reaction is finished, cool down to room temperature, filter to obtain the by-product sodium nitrate, then distill off methanol (GC shows methyl octanoate), lower the temperature to 0°C, then slowly add 5% nitric acid dropwise, adjust the pH value to 3-4, The solid was precipitated, filtered, and the filter cake was dried to obtain 59 g of octanoylhydroxamic acid, with a yield of 74%; the filtrate was separated to obtain 1.4 g of an oil, 1 H NMR identified it as n-octanoic acid; the remaining aqueous phase was concentrated to obtain solid sodium nitra...

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Abstract

The invention discloses a method for preparing octanohydroxamic acid and belongs to the technical field of synthesis of cosmetic raw materials. The method is characterized by comprising the following steps: adding sodium hydroxide into a mixed system of hydroxylamine nitrate and methanol at the temperature of 0-10 DEG C under stirring conditions; adding methyl caprylate, carrying out a hydroxyl oximation reaction at the temperature of 30-60 DEG C for 2-6 hours, and filtering to remove sodium nitrate after the reaction is completed; distilling and recovering the methanol, cooling the reaction system to 0 DEG C, adding dilute nitric acid with the concentration of 5wt%, regulating the pH value to 3-4, separating out the solids, and filtering and drying so as to obtain octanohydroxamic acid; and separating the filtrate, recovering the oily matter, and performing water-phase concentration so as to obtain sodium nitrate solids, wherein the molar ratio of the methyl caprylate to hydroxylamine nitrate to sodium hydroxide is 1:(1-2):(2-3). According to the method disclosed by the invention, recycling of the solvent methanol is realized, a byproduct of sodium nitrate with relatively high economic value is obtained, and the method is mild in reaction conditions and favorable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of octanoyl hydroxamic acid, which belongs to the technical field of cosmetic raw material synthesis. Background technique [0002] Caprylyl hydroxamic acid is one of the components of cosmetics. Its function is similar to that of EDTA disodium salt. By chelating metal ions, it stabilizes part of the inorganic salts in the system and effectively inhibits the growth of Aspergillus niger. [0003] The production processes of the prior art all use hydroxylamine hydrochloride or hydroxylamine sulfate as the main raw material, and generate hydroxylamine under the action of sodium hydroxide with more than twice the equivalent, and further undergo hydroximation reaction with methyl octanoate or ethyl ester, acidify The main product caprylyl hydroxamic acid is processed, and a large amount of sodium chloride or sodium sulfate is produced correspondingly, but the economic value of the above-mentioned by-products is ...

Claims

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Application Information

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IPC IPC(8): C07C259/06
CPCC07C259/06
Inventor 赵景瑞焦志刚杨正龙邹忠华翟宏斌
Owner 禹城禹圳生物科技有限公司
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