Organic compound and preparation method and application thereof

An organic compound and condensation reaction technology, applied in organic chemistry, sulfide preparation, flotation, etc., can solve the problems of poor solubility, poor short-chain hydrophobicity of amido hydroxamic acid, etc., and achieve easy operation and good flotation Effect, the effect of mild reaction conditions

Active Publication Date: 2021-04-02
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] In order to solve the above-mentioned technical problems existing in the prior art, one of the purposes of the present invention is to provide a kind of organic compound, by combining sulfide, amido and hydroxamic acid groups, develop efficient hydroxamic acid organic compound, according to The structural design of the present invention enables each functional group to have a strong synergistic effect, effectively solving the problems of poor solubility of thioether-based hydroxamic acid in aqueous solution and poor short-chain hydrophobicity of amidohydroxamic acid

Method used

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  • Organic compound and preparation method and application thereof
  • Organic compound and preparation method and application thereof
  • Organic compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Embodiment 1: the preparation of N-benzylthioacetylaminohexyl hydroxamic acid

[0048] Weigh 3.64g 96.15% benzylthioacetic acid into 50ml dichloromethane, add 3.24g 99% 1,1'-carbonyldiimidazole and 3.63g 98% 6-aminocaproic acid methyl ester hydrochloride, room temperature React under the conditions for 6 hours, after the reaction is finished, distill under reduced pressure, wash with water, and dry to obtain methyl N-benzylthioacetylaminocaproate; weigh 2.94g of 96% sodium hydroxide and slowly add it dropwise to 2.68g of 99.5% hydroxylamine hydrochloride Stir in the solution for 0.5h; weigh 10.82g of N-benzylthioacetylaminocaproic acid methyl ester, add the mixed solution of hydroxylamine hydrochloride and sodium hydroxide, heat to 40°C under stirring, and react for 4h to obtain the desired N-benzyl The thioacetylaminohexyl hydroxamic acid product has the structure figure 1 Shown; The optimal configuration at DFT / B3LYP 6-311G(d) level is as follows Figure 5 Shown; DF...

Embodiment 2

[0056] Embodiment 2: the preparation of N-benzylthioacetylaminohexyl hydroxamic acid

[0057] Weigh 18.20g of 96.15% benzylthioacetic acid into 50ml of dichloromethane, add 16.20g of 99% 1,1'-carbonyldiimidazole and 18.15g of 98% 6-aminocaproic acid methyl ester hydrochloride, room temperature Under the conditions of reaction for 10 hours, after the reaction was completed, distilled under reduced pressure, washed with water, and dried to obtain methyl N-benzylthioacetamide caproate; weighed 4.20g of 96% sodium hydroxide and slowly added dropwise to 3.82g of 99.5% hydroxylamine hydrochloride Stir in the solution for 0.5h; weigh 15.45g of N-benzylthioacetylaminocaproic acid methyl ester, add the mixed solution of hydroxylamine hydrochloride and sodium hydroxide, heat to 40°C under stirring, and react for 4h to obtain the desired N-benzyl Thioacetamidohexyl hydroxamic acid product. The yield based on benzylthioacetic acid was 76.21%.

Embodiment 3

[0059] Embodiment 3: Iron ion in N-benzylthioacetylaminohexyl hydroxamic acid analysis solution

[0060] Mix 50ml of 1% N-benzylthioacetylaminohexyl hydroxamic acid solution with 10ml of Fe of unknown concentration 3+ The solution was mixed and shaken in a constant temperature oscillator at 30°C for 10 minutes. By measuring the absorbance in the aqueous phase and the absorbance of the original N-benzylthioacetylaminohexyl hydroxamic acid solution, it can be known that Fe 3+ The concentration is 0.12g / L. It can be seen that N-benzylthioacetylaminohexyl hydroxamic acid can be used as an analytical reagent for iron ions, and compared with o-phenanthroline, a common analytical reagent for iron ions, it is less toxic and more environmentally friendly.

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Abstract

The invention discloses an organic compound as well as a preparation method and application thereof. The organic compound has a structure as shown in a formula I in the description, wherein R is C1-C12 alkyl; and the organic compound is obtained by carrying out amino acid condensation on alkyl thioether acetic acid and methyl 6-aminoacetate hydrochloride and then carrying out hydroximation by adopting hydroxylamine and alkali. According to the invention, thioether, acylamino and hydroxamic acid groups are combined to develop an efficient hydroxamic acid organic compound, the functional groupshave a strong synergistic effect according to the structural design of the invention, and the compound can be used as an analytical reagent for metal ions and a collecting agent for mineral flotation.In addition, the preparation method disclosed by the invention is simple, mild in reaction condition and easy to operate.

Description

technical field [0001] The present invention relates to the field of organic compounds, in particular to an organic compound and its preparation method and application, more specifically, to a 6-thioetheramidohexyl hydroxamic acid organic compound, its preparation method and its analysis as a metal ion Application of reagents and collectors for mineral flotation. Background technique [0002] Because of its strong ability to chelate metal ions, chelating agents can interact with metal ions to form chelates with completely different properties, reduce and control the concentration of metal ions, and are used in mineral flotation, hydrometallurgy, extraction and separation of metal elements, etc. widely used in the process. Due to its unique structure and chemical reactivity, hydroxamic acid can form a five-membered ring structure by combining two O atoms in the carbonyl group and the hydroxyl group with metal cations, and is a relatively common chelating agent. Chinese pate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/20B03D1/012B03D101/02B03D103/02
CPCC07C323/52C07C319/20B03D1/012B03D2201/02B03D2203/02Y02P10/20
Inventor 钟宏孙青王帅
Owner CENT SOUTH UNIV
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