Preparation method of weedicide hexazinone

A technology of hexazinone and herbicide, which is applied in the field of preparation of the herbicide hexazinone, can solve the problems of narrow operating flexibility range, potential safety hazards in the use of dimethylamine, strict equipment requirements, etc., and achieves simple synthetic route method and high reaction rate. Effects with low equipment requirements

Active Publication Date: 2015-03-11
XINYI AGRI CHEM PLANT JIANGSU PROV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Both of these schemes have disadvantages: in the first scheme, the gas dimethylamine introduced needs to be removed by adding water, and the waste water generated increases the pressure on environmental protection, and the use of dimethylamine has potential safety hazards. In addition, this scheme cannot completely Inhibit side reactions, and about 10% of side reactions still occur; the second option has stricter requirements on equipment, and the operating flexibility range is very narrow, which also increases production costs

Method used

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  • Preparation method of weedicide hexazinone
  • Preparation method of weedicide hexazinone
  • Preparation method of weedicide hexazinone

Examples

Experimental program
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Effect test

Embodiment 1

[0028] In the reactant guanidine used in this embodiment, R=ethyl, and the molecular weight is 173.

[0029] Mechanical stirring, thermometer and inner diameter 15mm are housed, add the toluene solution 346g of 800g toluene, guanidine in the 2000mL reaction bottle of length 300mm built-in triangular stainless steel packed tower (wherein the mass content of guanidine is 50%, the amount of substance of guanidine is 1mol) and Cyclohexylamine 100g (1mol), reacted at 65~70°C for 2h, then under vacuum at 200mmHg, rectified under reduced pressure to remove the ethanol generated by the reaction, took samples for analysis during the rectification process, and stopped the rectification after all the guanidines had been converted. The toluene solution of the intermediate compound guanidinourea was obtained.

[0030] Add 1800g of toluene and the guanidinourea toluene solution obtained by the above reaction in a 5000mL reaction flask equipped with a mechanical stirrer, a thermometer, a dro...

Embodiment 2

[0032] In the reactant guanidine used in this embodiment, R=ethyl, and the molecular weight is 173.

[0033] Mechanical stirring, thermometer and internal diameter 15mm are housed, and in the 2000mL reaction bottle of length 300mm built-in triangular stainless steel packing tower, add the benzene solution 346g of 800g benzene, guanidine (wherein the mass content of guanidine is 50%, the amount of substance of guanidine is 1mol) and Cyclohexylamine 102g (1.02mol), react at 70-80°C for 3h, then under vacuum at 200mmHg, rectify under reduced pressure to remove the ethanol generated by the reaction, take samples for analysis during the rectification process, and stop the rectification after all guanidines have been converted , to obtain the benzene thin solution of the intermediate compound guanidyl urea.

[0034] Add 1800g of benzene and the guanidinourea benzene solution obtained by the above reaction in a 5000mL reaction flask equipped with a mechanical stirrer, a thermometer, ...

Embodiment 3

[0036] In the reactant guanidine used in this embodiment, R=ethyl, and the molecular weight is 173.

[0037] Mechanical stirring, thermometer and internal diameter 15mm are housed, add the chloroform solution 346g of 1400g chloroform, guanidine in the 2000mL reaction bottle of length 300mm built-in triangular stainless steel packed tower (wherein the mass content 50% of guanidine, the amount of substance of guanidine is 1mol) and Cyclohexylamine 105g (1.05mol), react at 55-60°C for 4h, then azeotropic distillation to remove the ethanol generated by the reaction, sampling and analysis during the rectification process, stop the rectification after all the guanidines have been converted to obtain the intermediate compound Guanidylurea dilute solution in chloroform.

[0038] Add 3000g chloroform and the dilute guanidinourea chloroform solution obtained by the above reaction in a 5000mL reaction flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, a clear tub...

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Abstract

In order to solve the problems of side reaction and difficulty in inhibiting side reaction in the existing weedicide hexazinone preparation method, the invention discloses a new hexazinone preparation method which comprises the following steps: 1. reacting guanidine and cyclohexylamine so that the ester group on the guanidine is aminolyzed to generate an intermediate guanido urea; 2. reacting the intermediate guanido urea with phosgene under the action of an acid-binding agent so that the intermediate guanido urea is cyclized to generate hexazinone; and 3. cooling the mixture obtained in the step 2 to room temperature, carrying out vacuum filtration, washing, washing the mother solution with water, desolventizing under reduced pressure, adding petroleum ether to crystallize, filtering and drying to obtain the hexazinone crystal. The preparation method has the advantages of simple steps, no side reaction, high yield and low cost, and can obtain the high-purity hexazinone.

Description

technical field [0001] The invention belongs to the technical field of herbicides, and in particular relates to a preparation method of the herbicide hexazinone. Background technique [0002] Hexazinone is a systemic selective, post-emergence contact triazepine herbicide developed by DuPont Company of the United States in 1974. Due to its strong killing power to weeds and shrubs, it is widely used in the United States, Australia, and New Zealand. It has been widely used in many countries, and it is a highly efficient, low-toxic and environmentally friendly herbicide. [0003] At present, the synthesis methods of hexazinone at home and abroad mainly refer to U.S. Patents US4178448 and US4150225. The synthesis of triazine rings uses a strong base as a cyclization catalyst, so that the alcohol generated by the cyclization is exchanged with the dimethylamine group of hexazinone to form Cyclization side reaction products affect the yield. These two patents point out that there ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/46
CPCC07D251/46
Inventor 刘宇邓玉智李强顾思雨杨海松孙新许思如李欣
Owner XINYI AGRI CHEM PLANT JIANGSU PROV
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