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The synthetic method of hydroxamic acid compound

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of high reaction temperature, complex post-processing, and many wastes, and achieve the effects of high molecular concentration, simple post-processing, and avoiding environmental pollution.

Active Publication Date: 2020-07-14
CENT SOUTH UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the above-mentioned technical problems existing in the prior art, the present invention provides a method for synthesizing hydroxamic acid compounds to solve the problems of using a large amount of organic solvents, high reaction temperature, high waste, complex post-treatment, and unfavorable environmental protection. It has the advantages of wide source of raw materials, low cost, simple operation, high efficiency, easy separation of products, high yield, and easy realization of industrial production.

Method used

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  • The synthetic method of hydroxamic acid compound
  • The synthetic method of hydroxamic acid compound
  • The synthetic method of hydroxamic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Add 24.55g of benzoic acid (99.5% in content) and 21.05g of acetic anhydride (97% in content) into a ball mill, grind for 5 minutes, then add 14.11g of hydroxylamine hydrochloride (98.5% in content), and continue grinding for 45 minutes to obtain a white solid The product is the target collector product. Through analysis and detection, the content of benzyl hydroxamic acid is 51.82%, and the yield of benzyl hydroxamic acid based on benzoic acid is 95.81%.

[0067] The product was characterized after being separated and purified by column chromatography, and the infrared spectrum of benzohydroxamic acid was as follows: figure 1 As shown, its main characteristic peaks are (cm -1 ): 3297 belongs to the N-H stretching vibration peak, 3069 belongs to the C=C-H stretching vibration peak on the benzene ring, 2756 belongs to the O-H stretching vibration peak, 1645 and 1611 belong to the -HN-C=O vibration peak, 1561 belongs to the -C=N- Stretching vibration peaks, 1490 and 145...

Embodiment 2

[0071] Add 24.55g of benzoic acid (99.5% in content) and 21.05g of acetic anhydride (97% in content) into a ball mill, grind for 5 minutes, then add 14.11g of hydroxylamine hydrochloride (98.5% in content), and continue grinding for 45 minutes to obtain a white solid The product was washed three times with 50ml of distilled water, filtered, and the filter cake was vacuum-dried at 50°C to obtain a pure white solid product, which was the target collector product. Through analysis and detection, the content of benzohydroxamic acid is 90.55%, and the yield of benzoic acid-based benzohydroxamic acid is 91.79%.

Embodiment 3

[0073] 24.55g benzoic acid (content is 99.5%) and 41.68g dicyclohexylcarbodiimide (DCC) (content is 99%) add ball mill jar, grind 5min, then add 14.11g hydroxylamine hydrochloride (content is 98.5%), After continuing to grind for 45 minutes, a white solid product was obtained, which was the target collector product. Through analysis and detection, the content of benzohydroxamic acid is 37.04%, and the yield of benzoic acid-based benzohydroxamic acid is 94.74%.

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Abstract

The invention discloses a method for synthesizing a hydroximic acid compound. The method comprises the step of subjecting an organic carboxylic acid compound with a structure represented by a formula(I) shown in the description and a hydroxylamine compound with a structure represented by a formula (II) shown in the description to a grinding reaction in the presence of a coupling reagent, therebypreparing the hydroximic acid compound with a structure represented by a formula (III) shown in the description. According to the method, the technical problems that a large amount of organic solventis used, the reaction temperature is high, wastes are plenty, the aftertreatment is complicated, environmental protection is adverse and the like are solved, and the method has the advantages that thesource of the raw materials is wide, the cost is low, the operation is simple, the efficiency is high, the product is easy to separate, the yield is high, industrial production is easy to achieve andthe like.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic intermediates, in particular to a method for synthesizing hydroxamic acid compounds, in particular to a method for preparing hydroxamic acid compounds by grinding reaction. Background technique [0002] Hydroxamic acid contains active groups hydroxyl group (-OH) and oxime group (=C=NOH), and its molecule has C=N that cannot rotate freely, and mainly exists in the form of trans isomerism. The hydroxyl oxygen atom and the oxime nitrogen atom in the hydroxamic acid molecule can coordinate with most metal elements, usually forming a four-membered or five-membered ring chelate. Therefore, hydroxamic acid compounds are widely used in mineral flotation, metallurgy, medicine, water treatment and other fields. [0003] Traditional hydroxamic acid synthesis methods generally use lower alcohol esters of carboxylic acids and hydroxylamine to react in alkaline solvents. The commonly used solvents...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C259/06C07C259/08C07C259/10
Inventor 马鑫邓兰青钟宏王帅
Owner CENT SOUTH UNIV
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