Chelating agent with high stability and high iron chelating ability and preparation method thereof

A high stability, chelating agent technology, applied in the preparation of organic compounds, chemical instruments and methods, cyanide reaction preparation, etc., can solve the problems of low yield ortho-body, poor selectivity, excessive phenol raw materials, etc., to achieve high iron Chelating ability, high stability and effective

Active Publication Date: 2013-09-18
SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the production process of EDDHA mainly adopts the one-step Mannich reaction preparation of phenol, ethylenediamine, glyoxylic acid and sodium oxide, such as the production process of EDDHA chelated iron reported in US Patent No. Low yield (61.4%), poor selectivity of ortho-body (o,o-EDDHA) and large excess of phenol raw materials

Method used

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  • Chelating agent with high stability and high iron chelating ability and preparation method thereof
  • Chelating agent with high stability and high iron chelating ability and preparation method thereof
  • Chelating agent with high stability and high iron chelating ability and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Add 10.81g (100mmol) p-cresol to a round bottom flask equipped with a condenser tube and a mechanical stirring paddle, heat to 45°C to 50°C to melt it; then add 3.0g (50mmol) ethylenediamine and 0.3g Tetrabutylammonium Hydroxide, stir 10min; Add 13.3g (100mmol) of 30% sodium hydroxide and 17.61g (100mmol) of 50% glyoxylic acid aqueous solution slowly to the above-mentioned mixture again after mixing, be warming up to After reacting at 70°C for 3 hours, cool to room temperature; add 100mL water and 150mL dichloromethane to the above reactants respectively, stir vigorously for 30min, separate the organic phase, and extract the aqueous phase with dichloromethane 3 times, 60ml each time; then water Adjust the pH to 5-6 with 5% HCl, filter and dry at room temperature for about 12 hours to obtain about 17.5 g of white solid, which is the finished product of the chelating agent N,N-m-methyl-o-hydroxyphenylacetoxyethylenediamine. Yield: 90%, Purity: >98% (HPLC).

Embodiment 2

[0022] Add 12.86g (100mmol) p-chlorophenol into a round bottom flask equipped with a condenser tube and a mechanical stirring paddle, heat it to 45°C to 50°C to melt it; then add 3.0g (50mmol) ethylenediamine to the above system and tetrabutylammonium hydroxide 0.3g, stirred for 10min; after mixing evenly, slowly added 13.3g (100mmol) of 30% sodium hydroxide and 17.61g (100mmol) of glyoxylic acid (100mmol) aqueous solution of 50% to the above mixture, and the temperature was raised. After reacting at 75°C for 3h, cool to room temperature; add water (100mL) and dichloromethane (150mL) to the above reactant respectively, stir vigorously for 10min, separate the organic phase, and extract the aqueous phase with dichloromethane three times, each time 60ml. Then the pH of the water phase was adjusted to 5-6 with 5% HCl, and after standing at room temperature for about 12 hours, it was filtered and dried to obtain about 18.67 g of a white solid, which was the product of the chelating...

Embodiment 3

[0024] Add 10.81g (100mmol) p-cresol to a round bottom flask equipped with a condenser tube and a mechanical stirring paddle, heat to 40°C to 45°C to melt it; then add 4.41g (50mmol)1,4 to the above system -Butanediamine and dodecyltrimethylammonium hydroxide 0.5g, stirred for 10min; after mixing evenly, slowly add 30% sodium hydroxide 13.3g (100mmol) and 50% ethyl alcohol dropwise to the above mixture successively 17.61g (100mmol) of aldehyde acid aqueous solution, heated up to 70°C for 3h, then cooled to room temperature; added water (100mL) and dichloromethane (150mL) to the above reactants, stirred vigorously for 10min, separated the organic phase and the aqueous phase Extract with dichloromethane 3 times, 60ml each time, then adjust the pH of the aqueous phase to 5-6 with 5% HCl, leave it at room temperature for about 12 hours, filter and dry to obtain about 17.7g of white solid, which is the chelating agent N,N- The finished product of m-methyl o-hydroxyphenylacetic acid...

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Abstract

The invention relates to a chelating agent with high stability and high iron chelating ability and a preparation method thereof. The chelating agent is a target compound which is prepared from phenol derivatives, aliphatic diamine and glyoxalic acid aqueous solution serving as initial materials by mannich reaction in a one-step synthesis manner. By adopting the preparation method disclosed by the invention, the defects of fussy synthesis steps, low yield and poor selectivity of the traditional chelating agents such as EDDHA (ethylenediamine-N,N'-diacetic acid) are overcome; and the obtained chelate has higher stability and iron chelating ability relative to EDTA (ethylene diamine tetraacetic acid) and EDDHA.

Description

technical field [0001] The invention belongs to the technical field of preparation of chemical products, and relates to a chelating agent with high stability and high iron chelating ability and a preparation method thereof. Background technique [0002] EDDHA (ethylenediamine-N,N-hydroxyphenylacetic acid) and its iron chelate can maintain a stable solution state within the pH range of 3 to 10, so it is extremely practical and widely used in the photosensitive film processing industry and high-end trace Element chelated fertilizers, etc. The most important step in the production of such chelated iron is the synthesis of the ligand EDDHA. At present, the production process of EDDHA mainly adopts the one-step Mannich reaction preparation of phenol, ethylenediamine, glyoxylic acid and sodium oxide, such as the production process of EDDHA chelated iron reported in US Patent No. Low yield (61.4%), poor selectivity of ortho-body (o,o-EDDHA) and large excess of phenol raw material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/10
Inventor 薛群翔宫飞祥
Owner SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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