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Preparation of N-alkyl thiophosphoryl triamide by one-pot method

A technology of hydrocarbyl thiophosphoryl triamine and hydrocarbyl thiophosphoryl dichloride, which is applied in the field of chemical synthesis, can solve the problems of long working hours, many reaction steps and high cost, and achieves a simple process, suitable reaction conditions and low cost. Effect

Inactive Publication Date: 2009-04-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a one-step ("one-pot method") preparation process of a urease inhibitor N-hydrocarbyl thiophosphoryltriamide with simplified process, continuous, high efficiency, low cost, and recyclable solvent and acid-binding agent , to solve the problems of low yield, long working hours, high cost and many reaction steps in the prior art

Method used

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  • Preparation of N-alkyl thiophosphoryl triamide by one-pot method
  • Preparation of N-alkyl thiophosphoryl triamide by one-pot method
  • Preparation of N-alkyl thiophosphoryl triamide by one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1 Preparation of N-n-propylthiophosphoric triamide

[0020] One-pot preparation reaction equation:

[0021]

[0022] Under nitrogen protection, THF134.40g was added to a 1000ml four-neck flask equipped with mechanical stirring, a thermometer, a constant pressure titration funnel, and a reflux condenser, and phosphorus trichloride (PSCl 3 ) 51.9g; 18.3g of n-propylamine (NPA) and 30.4g of triethylamine (TEA) were mixed and dissolved in 136.0g of THF and added to a 250ml constant-pressure titration funnel; The rate of addition was completed dropwise in 2 hours and 30 minutes, and the dropwise addition was completed, and the stirring was continued for 1 hour. Install the ammonia intubation tube, open the ammonia valve to feed ammonia gas, control the ammonia pressure to less than 0.12MPa; control the temperature at 5°C, pass ammonia gas for 2 hours, and at the same time the system will no longer absorb ammonia gas, slowly warm up to room temperature, stop S...

Embodiment 2

[0023] Embodiment 2 Preparation of N-n-butylthiophosphoric triamide

[0024] The one-pot preparation reaction equation is as follows:

[0025]

[0026] Under nitrogen protection, THF158.6g was added to a 1000ml four-necked flask equipped with mechanical stirring, a thermometer, a constant pressure titration funnel, and a reflux condenser, and phosphorus trichloride (PSCl 3 ) 50.9g; 22.6g of n-butylamine (NBA) and 30.4g of triethylamine (TEA) were mixed and dissolved in 138.9g of THF and added to a 250ml constant pressure titration funnel; the reaction temperature was controlled to reach -5°C, and the dropwise addition , control the rate of addition, the dropwise addition is completed in 3 hours and 30 minutes, and the dropwise addition is completed, and the stirring is continued for 1 hour. Install the ammonia intubation tube, open the ammonia valve to feed ammonia gas, and control the pressure of ammonia gas to be less than 0.12MPa; control the temperature at 0°C to 5°C, ...

Embodiment 3

[0027] Embodiment 3 Preparation of N-isobutylphosphorothiotriamide

[0028] The one-pot preparation reaction equation is as follows:

[0029]

[0030] Under nitrogen protection, THF135.7g was added to a 1000ml four-necked flask equipped with mechanical stirring, a thermometer, a constant pressure titration funnel, and a reflux condenser, and phosphorus trichloride (PSCl 3 ) 51.9g; 22.6g of iso-n-butylamine and 30.4g of triethylamine (TEA) were mixed and dissolved in 136.6g of THF and added to a 250ml constant pressure titration funnel; the reaction temperature was controlled to reach 0°C, and the dropwise addition was started. Acceleration, the dropwise addition was completed in 3 hours, and the dropwise addition was completed, and the stirring was continued for 1 hour. Install the ammonia intubation tube, open the ammonia valve to feed ammonia gas, control the pressure of ammonia gas to less than 0.12MPa, control the temperature at 5°C, pass ammonia gas for 2 hours, slowly ...

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Abstract

The invention discloses a method for preparing N-alkyl thiophosphoryl triammonium through a favorable one-pot method in industry. The method is characterized in that in an organic solvent, in the presence of a tertiary amine acid-binding agent, and at an reaction temperature of between 10 below zero and 50 DEG C, thiophosphoryl chloride and alkyl primary amine react to generate N-alkyl thiophosphoryl bichloride and tertiary amine acid-binding agent hydrochloride as intermediate products; the generated intermediate products continuously react with ammonia gas in the same reaction system without purification and separation to generate the N-alkyl thiophosphoryl triammonium, the acid-binding agent and ammonium chloride as target products; the target products are filtered and condensed to obtain the product (as the right upper formula); and the yield of the N-alkyl thiophosphoryl triammonium is more than or equal to 85 percent. The method has the advantages of compact preparation process, low cost, high yield and suitablility for scale industrialized production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a preparation method of an N-hydrocarbylthiophosphoryl urease inhibitor, in particular to a novel industrially advantageous "one-pot method" for preparing a urease inhibitor N-hydrocarbylthiophosphorus Acyl triamide method. Background technique [0002] N-hydrocarbylthiophosphoric triamide is one of the effective soil urease inhibitors used in agriculture. The main research reports on the synthesis of this type of compound include: [0003] In 1985, Jaroslav F.Kolc etc. first disclosed in US4530714 that N-hydrocarbylthiophosphoric triamide compounds had urease inhibitory activity, adding urea of ​​this type of compound can improve the utilization rate of urea, promote the growth of plants, and improve the crop yield . Also disclosed in this patent is the synthetic preparation method of N-hydrocarbyl thiophosphoric triamide, that is, a two-step method ("two-pot method"...

Claims

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Application Information

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IPC IPC(8): C07F9/22
Inventor 孟庆伟都健鞠志永赵伟杰
Owner DALIAN UNIV OF TECH
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