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Continuous flow process for synthesis of hydroxamic acid

A technology of hydroxamic acid and hydroxyl group, applied in the field of synthesizing hydroxamic acid, can solve the problems of slowing down the reaction speed and long reaction time, etc.

Pending Publication Date: 2022-07-12
UNITED PHOSPHORUS LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is the long reaction time, which takes 12 hours, and the reaction temperature is kept as low as 0°C to 30°C, which slows down the reaction
[0008] In addition, the methods disclosed above are batch methods that may require intermittent introduction of frequently changing raw materials, different process conditions within the vessel, and different purification methods

Method used

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  • Continuous flow process for synthesis of hydroxamic acid
  • Continuous flow process for synthesis of hydroxamic acid
  • Continuous flow process for synthesis of hydroxamic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0166] The continuous reaction was carried out using a three-line plug flow reactor (PFR). Ethyl acetate (88.11 g) was fed to the reactor at a rate of 7.61 ml / min through the first feed line, and a 30% hydroxylamine sulfate solution (169 gm hydroxylamine sulfate in 395 gm water) was passed through the second feed line at 16.5 ml. 30% NaOH solution (42 gm sodium hydroxide in 92.5 gm water) was fed to the reactor at a rate of 9.2 ml / min through the third line. The flow rate was adjusted to maintain a stoichiometric ratio of hydroxylamine sulfate:ethyl acetate:sodium hydroxide of approximately 1:2.15:2.6. All three feed lines discharged their contents into the reaction vessel, which was maintained at 90°C, to form acetohydroxamic acid with a residence time of 3 minutes. The results of the reaction setup are highlighted in Table 1. Samples were analyzed by HPLC (HPLC purity 97%).

Embodiment 2

[0168] The continuous reaction was carried out using a three-line PFR reactor. Ethyl acetate (88.11 g) was fed to the reactor at a rate of 7.0 ml / min through the first feed line, and a 30% hydroxylamine hydrochloride solution (71 gm hydroxylamine hydrochloride in 161 gm water) was passed through the second feed line at 12.64 ml 30% NaOH solution (42 gm sodium hydroxide in 92.5 gm water) was fed to the reactor at a rate of 13.42 ml / min through the third line. The flow rate was adjusted to maintain a 1:1.15:2.0 stoichiometric ratio of hydroxylamine hydrochloride:ethyl acetate:sodium hydroxide. All three feed lines drain their contents into the reaction vessel, which is maintained at 90°C. The desired product, acetohydroxamic acid, was formed within a residence time of 3 minutes without changing the existing conditions. The results of the reaction setup are highlighted in Table 1. The samples were analyzed by HPLC (HPLC purity 96%).

Embodiment 3

[0170] The continuous reaction was carried out using a three-line PFR. Ethyl acetate (88.11 gm) was fed to the reactor through the first feed line at a rate of 7.4 ml / min, and a 30% hydroxylamine sulfate solution (169 gm hydroxylamine sulfate in 395 gm water) was fed through the second feed line at 15.6 ml. 30% NaOH solution (42 gm sodium hydroxide in 92.5 gm water) was fed to the reactor at a rate of 10.38 ml / min through the third line. The flow rate was adjusted to maintain a 1:2.2:3 stoichiometric ratio of hydroxylamine sulfate:ethyl acetate:sodium hydroxide. All three feed lines drain their contents into the reaction vessel, which is maintained at 90°C. The desired product, acetohydroxamic acid, was formed within a residence time of 3 minutes without changing the existing conditions. The results of the reaction setup are highlighted in Table 1. The samples were analyzed by HPLC (98% purity by HPLC).

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Abstract

The present invention relates to a process for the synthesis of hydroxamic acid by a continuous flow process, wherein the process comprises reacting an alkyl ester with a hydroxylamine salt in the presence of a base in a microreactor system and continuously producing hydroxamic acid.

Description

technical field [0001] The present invention relates to a continuous flow process for the synthesis of hydroxamic acids. The present invention more particularly relates to the synthesis of hydroxamic acids in a microreactor system. Background technique [0002] Hydroxamic acids can be represented by the structural formula R 1 C(O)N(OH)R 2 means, where R 1 Typically hydrogen or a hydrocarbon group such as an alkyl group, cycloalkyl group or aromatic group, and R 2 Can be a hydrogen atom or a hydrocarbon group such as an aromatic group or an alkyl group. [0003] Hydroxamic acids are known to exhibit microbicidal effects and can be used in practice to control unwanted microorganisms. These active compounds are suitable as plant protection agents, in particular as fungicides. Fungicides in plant protection are used for the control of clubroot, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes. [0004] In general, hydroxamic acids a...

Claims

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Application Information

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IPC IPC(8): C07C259/06
CPCC07C259/06B01J19/0093B01J2219/00033B01J2219/00894
Inventor 米林德·贾格纳什·皮姆帕尔普拉尚·瓦桑特·基尼
Owner UNITED PHOSPHORUS LTD
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