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Preparation methods of 3-nitrile-2,4-dihalogeno phenylphosphonic acid and salts thereof

A technology of dihalophenylphosphonic acid and dihalophenylphosphonate is applied in the technical field of polymer materials, and can solve the problems of easy deformation, narrow pH range, increasing water treatment process technology and the like

Active Publication Date: 2014-08-27
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cellulose acetate membranes are susceptible to microbial attack, are easily deformed under high temperature or high pressure conditions, and are only suitable for a narrow pH range; aromatic polyamide composite membranes show rather weak resistance to continuous exposure to oxidizing agents such as free chlorine Therefore, the process of water treatment process is increased, and the cost of water purification treatment is also increased

Method used

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  • Preparation methods of 3-nitrile-2,4-dihalogeno phenylphosphonic acid and salts thereof
  • Preparation methods of 3-nitrile-2,4-dihalogeno phenylphosphonic acid and salts thereof
  • Preparation methods of 3-nitrile-2,4-dihalogeno phenylphosphonic acid and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of sodium 3-cyano-2,4-difluorophenylphosphonate:

[0042] (1) Preparation of 3-bromo-2,6-difluorobenzonitrile:

[0043]

[0044] Take a 2 L four-neck flask, add 600 mL of 60% sulfuric acid, add 139.0 g (1.0 mol) of 2,6-difluorobenzonitrile under electric stirring, and 2 Under protection, control the reaction temperature below 35°C, add 250.5 g of KBrO in 10 batches 3 (1.5 mol), monitored by TLC, reacted for 5-6 days, stopped the reaction after the raw material point disappeared, prepared 800 mL of 20% ice-salt solution, and poured the reaction solution into ice-salt water. After the product settles, quickly carry out suction filtration to obtain an orange crude product, which is washed with CCl 4 Dissolve the crude product with 5% NaHSO 3 solution, saturated Na 2 CO 3 Wash the solution and water until the solution is neutral, dry it with anhydrous sodium sulfate, filter the solution, and steam in a water bath at 60°C to obtain a light yellow liquid, ...

Embodiment 2

[0052] Preparation of sodium 3-cyano-2,4-dichlorophenylphosphonate:

[0053] (1) Preparation of 3-bromo-2,6-dichlorobenzonitrile:

[0054]

[0055] Take a 2 L four-neck flask, add 600 mL of 60% sulfuric acid, add 172.0 g (1.0 mol) of 2,6-dichlorobenzonitrile under electric stirring, and 2 Under protection, control the reaction temperature below 35°C, add 250.5 g of KBrO in 10 batches 3 (1.5 mol), monitored by TLC, reacted for 5-6 days, stopped the reaction after the raw material point disappeared, prepared 800 mL of 20% ice-salt solution, and poured the reaction solution into ice-salt water. After the product settles, quickly carry out suction filtration to obtain an orange crude product, which is washed with CCl 4 Dissolve the crude product with 5% NaHSO 3 solution, saturated Na 2 CO 3 Wash the solution and water until the solution is neutral, dry it with anhydrous sodium sulfate, filter the solution, and steam in a water bath at 60°C to obtain a light yellow liquid, ...

Embodiment 3

[0063] Preparation of lithium 3-cyano-2,4-difluorophenylphosphonate:

[0064]

[0065] Mix diethyl 3-cyano-2,4-difluorophenylphosphonate with a certain amount of concentrated hydrochloric acid, raise the temperature to 110°C, heat to reflux for 24 h, and extract the reaction solution with ethyl acetate several times after cooling. Combine the organic phases, overnight with anhydrous magnesium sulfate, filter, and rotary evaporate to obtain the crude product of 3-cyano-2,4-difluorophenylphosphonic acid, dissolve the crude product in water, adjust the pH value to 7-8 with lithium hydroxide solution, and evaporate to dryness water, the obtained solid was dissolved in methanol, the insoluble matter was filtered off, methanol was spin-dried, and the obtained solid was recrystallized from water and ethanol to obtain lithium 3-cyano-2,4-difluorophenylphosphonate with a yield of 94%. 1 H-NMR (D 2 O): δ = 7.96-7.87 (m, 1 H), 7.08 (t, J = 8.8 Hz, 1 H) ppm; 31 P-NMR (D 2 O): δ = ...

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Abstract

The invention discloses a series of polymerizable novel organic monomers 3-nitrile-2,4-dihalogeno phenylphosphonic acids and salts and preparation method thereof. The 3-nitrile-2,4-dihalogeno phenylphosphonic acid is a product prepared through mixing 3-nitrile-2,4-dihalogeno phenylphosphonate with acids, heating the obtained mixture for reaction, adding alkaline into the obtained product so as to adjust the pH value to 7-8, drying water by distillation, dissolving obtained solids by using methanol, removing insolubles by filtering, drying the methanol by spinning, and recrystallizing obtained solids by using water and ethyl alcohol. The novel organic monomers have a polymerization reaction with other monomers in a high-boiling-point aprotic organic solvent and in the presence of a mid-strong base, and then the obtained products are acidified, so that novel polymer materials containing phosphonate and a phosphonic acid are respectively obtained. The materials show good nanofiltration / reverse osmosis desalination and proton conduction properties.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to the fields of nanofiltration, reverse osmosis membrane water treatment and fuel cell application materials preparation, in particular to the synthesis of polyarylether polymers and new important phosphonic acids and salts thereof required The preparation method of the body, specifically the new organic monomer 3-cyano-2,4-dihalophenylphosphonic acid and its salts, and the related new polymers containing phosphonic acid and phosphonate groups materials, and methods for their efficient preparation. Background technique [0002] As an energy technology, fuel cells have the advantages of energy security, supply security and environmental friendliness. The proton exchange membrane is the core component of the fuel cell. The proton exchange membrane in the high-efficiency fuel cell has the following characteristics: high proton conductivity, low electron conductivity, low perm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/38C08G75/23B01D71/68H01M8/10H01M8/02H01M8/1034H01M8/1039
CPCY02E60/523Y02E60/50
Inventor 宋凡波张中标李华芸汤红英王智强宋爱茹
Owner TIANJIN NORMAL UNIVERSITY
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