CN100560571C - The preparation method of 2-nitro imido imidazolyl alkane - Google Patents
The preparation method of 2-nitro imido imidazolyl alkane Download PDFInfo
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- CN100560571C CN100560571C CNB200710023590XA CN200710023590A CN100560571C CN 100560571 C CN100560571 C CN 100560571C CN B200710023590X A CNB200710023590X A CN B200710023590XA CN 200710023590 A CN200710023590 A CN 200710023590A CN 100560571 C CN100560571 C CN 100560571C
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Abstract
A kind of preparation method of 2-nitro imido imidazolyl alkane belongs to the pesticide intermediate technical field.It is earlier acid and reacting ethylenediamine to be got ethylenediamine salt, ethylenediamine salt and nitroguanidine is reacted, then after filtration, dry and obtain finished product 2-nitro imido imidazolyl alkane again.The invention has the advantages that: raw materials cost is low, the reaction yield height, and good product quality, yield can reach more than 80%, and fusing point 232-234 ℃, content is more than 99%, and product has the sense organ of good white or light yellow crystal.
Description
Technical field
The present invention relates to the preparation method of 2-nitro imido imidazolyl alkane, belong to the pesticide intermediate technical field.
Background technology
The 2-nitro imido imidazolyl alkane is a kind of important pesticide intermediate, is the important source material that is used for Provado.Its structural formula is as follows:
Domestic have a bibliographical information (2-nitro-imine base imidazolidine new synthetic process, the Hebei chemical industry, 2002 (6), 40) by quadrol dihydrochloride and nitroguanidine prepared in reaction, it is that 2-nitro imido imidazolyl alkane yield is lower that this method shortcoming is to use quadrol dihydrochloride and nitroguanidine prepared in reaction compound III.
Other has bibliographical information (the synthetic and preliminary test of pesticide effectiveness of novel pesticide replacement-2-nitro imino--imidazolidine, agricultural chemicals, 2000 (1), 16-17) nitroguanidine and ethylenediamine-hydrochloride react in potassium hydroxide aqueous solution, the potassium hydroxide raw materials cost that this method shortcoming is to use is higher, and yield is low.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of 2-nitro imido imidazolyl alkane, this method yield height, good product quality, preparation cost is low.
The objective of the invention is to reach like this, a kind of preparation method of 2-nitro imido imidazolyl alkane, it is earlier acid and reacting ethylenediamine to be got ethylenediamine salt, again with ethylenediamine salt and nitroguanidine reaction, then after filtration, oven dry obtains finished product 2-nitro imido imidazolyl alkane, the temperature of reaction of described ethylenediamine salt and nitroguanidine reaction is 35-80 ℃, and the reaction times is 0.5-12h, and regulates pH8-12 with alkali in reaction process.
In one embodiment of the invention, described acid is sulfuric acid or hydrochloric acid or phosphoric acid, and described sulfuric acid is the vitriol oil.
In another embodiment of the present invention, described alkali is any one in potassium hydroxide, ammoniacal liquor, the liquid caustic soda.
In another embodiment of the present invention, described temperature of reaction is 60-65 ℃, and the described reaction times is 4-6h.
The invention has the advantages that: raw materials cost is low, the reaction yield height, and good product quality, yield can reach more than 80%, and fusing point 232-234 ℃, content is more than 99%, and product has the sense organ of good white or light yellow crystal.
Embodiment
The reaction formula of 2-nitro imido imidazolyl alkane provided by the invention is as follows:
Compound I Compound I I compound III
In the formula: Compound I, II, III are respectively quadrol vitriol, nitroguanidine, 2-nitro imido imidazolyl alkane.
Embodiment 1:
Suction 150Kg quadrol in the 1000L reactor, 300Kg water, the freezing vitriol oil that drips down drops into the 260Kg nitroguanidine to neutral, stirs, drip 30% liquid caustic soda to pH be 9, be warmed up to 60 ℃, reacted 6 hours, be cooled to room temperature, get rid of filter wet product, dry 254Kg finished product (content is more than 99%).
Embodiment 2:
Suction 150Kg quadrol in the 1000L reactor, 300Kg water, the freezing vitriol oil that drips down drops into the 260Kg nitroguanidine to neutral, stirs, drip 30% liquid caustic soda to pH be 10, be warmed up to 45 ℃, reacted 2 hours, be cooled to room temperature, get rid of filter wet product, dry 243Kg finished product (content is more than 99%).
Embodiment 3:
Suction 150Kg quadrol in the 1000L reactor, 300Kg water, the freezing vitriol oil that drips down drops into the 260Kg nitroguanidine to neutral, stirs, drip 30% liquid caustic soda to pH be 8, be warmed up to 80 ℃, reacted 10 hours, be cooled to room temperature, get rid of filter wet product, dry 230Kg finished product (content is more than 99%).
Embodiment 4:
Suction 150Kg quadrol in the 1000L reactor, 200Kg water, freezing dripping hydrochloric acid down drops into the 260Kg nitroguanidine to neutral, stir, drip 30% liquid caustic soda to pH be 9, be warmed up to 60 ℃, reacted 6 hours, be cooled to room temperature, get rid of filter wet product, dry 240Kg finished product (content is more than 99%).
Embodiment 5:
Suction 150Kg quadrol in the 1000L reactor, 300Kg water, the freezing vitriol oil that drips down is 9 to pH, input 260Kg nitroguanidine, stir, be warmed up to 60 ℃, reacted 6 hours, be cooled to room temperature, get rid of filter wet product, dry 225Kg finished product (content is more than 99%).
Embodiment 6:
Suction 150Kg quadrol in the 1000L reactor, 200Kg water, freezing dripping hydrochloric acid down drops into the 260Kg nitroguanidine to neutral, stir, drip 20% ammoniacal liquor to pH be 9, be warmed up to 60 ℃, reacted 6 hours, be cooled to room temperature, get rid of filter wet product, dry 252Kg finished product (content is more than 99%).
Embodiment 7:
Suction 150Kg quadrol in the 1000L reactor, 200Kg water, freezing dripping hydrochloric acid down drops into the 260Kg nitroguanidine to neutral, stirs, 30% potassium hydroxide that dropping is joined to pH be 9, be warmed up to 60 ℃, reacted 6 hours, be cooled to room temperature, get rid of filter wet product, dry 250Kg finished product (content is more than 99%).
Claims (4)
1, a kind of preparation method of 2-nitro imido imidazolyl alkane, it is characterized in that it is earlier acid and reacting ethylenediamine to be got ethylenediamine salt, again with ethylenediamine salt and nitroguanidine reaction, then after filtration, oven dry obtains finished product 2-nitro imido imidazolyl alkane, the temperature of reaction of described ethylenediamine salt and nitroguanidine reaction is 35-80 ℃, reaction times is 0.5-12h, and regulates pH8-12 with alkali in reaction process.
2, the preparation method of 2-nitro imido imidazolyl alkane according to claim 1 is characterized in that described acid is sulfuric acid or hydrochloric acid or phosphoric acid, and described sulfuric acid is the vitriol oil.
3, the preparation method of 2-nitro imido imidazolyl alkane according to claim 1 is characterized in that described alkali is any one in potassium hydroxide, ammoniacal liquor, the liquid caustic soda.
4, the preparation method of 2-nitro imido imidazolyl alkane according to claim 1 is characterized in that described temperature of reaction is 60-65 ℃, and the described reaction times is 4-6h.
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| CNB200710023590XA CN100560571C (en) | 2007-06-11 | 2007-06-11 | The preparation method of 2-nitro imido imidazolyl alkane |
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| CNB200710023590XA CN100560571C (en) | 2007-06-11 | 2007-06-11 | The preparation method of 2-nitro imido imidazolyl alkane |
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| CN100560571C true CN100560571C (en) | 2009-11-18 |
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558060A (en) * | 2011-12-29 | 2012-07-11 | 南通天泽化工有限公司 | Process for preparing imidazolidine |
| CN104672212B (en) * | 2013-11-26 | 2017-01-18 | 嘉兴学院 | Method for synthesizing imidacloprid employing cascade reaction |
| CN105061318B (en) * | 2015-07-28 | 2018-01-05 | 南通天泽化工有限公司 | The continuous production technology of imidazolidine |
| CN105330572A (en) * | 2015-12-09 | 2016-02-17 | 宁夏联森生物科技有限公司 | Method for preparing 3-beta-amino ethyl nitrourea |
| CN107162980A (en) * | 2017-05-25 | 2017-09-15 | 宁夏贝利特生物科技有限公司 | The method for producing imidazolidine with the discarded dilute sulfuric acid of production nitroguanidine |
| CN107759526A (en) * | 2017-11-09 | 2018-03-06 | 贝利特化学股份有限公司 | With the method for carbon dioxide production imidazolidine |
| CN112996775B (en) * | 2018-09-17 | 2023-09-19 | Upl有限公司 | Process for preparing 2-nitroiminoheterocyclic compounds |
| CN110028453B (en) * | 2019-05-10 | 2022-07-12 | 宁夏贝利特生物科技有限公司 | Preparation method of N-nitroiminoimidazolidine |
| CN112661774A (en) * | 2020-12-09 | 2021-04-16 | 南通天泽化工有限公司 | Preparation method of cycloxaprid |
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2007
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Non-Patent Citations (10)
| Title |
|---|
| 2-硝基亚胺基咪唑烷合成新工艺. 焦素霞，李涛，齐素忠.河北化工，第6期. 2002 |
| 2-硝基亚胺基咪唑烷合成新工艺. 焦素霞等.河北化工，第6期. 2002 |
| 2-硝基亚胺基咪唑烷合成新工艺. 焦素霞，李涛，齐素忠.河北化工，第6期. 2002 * |
| 2-硝基亚胺基咪唑烷合成新工艺. 焦素霞等.河北化工，第6期. 2002 * |
| Synthesis of 2-nitroimino-1,3-diazacycloalkanes.. B China Raju et al.Indian Journal of Chemistry,Vol.41B . 2002 |
| Synthesis of 2-nitroimino-1,3-diazacycloalkanes.. B China Raju et al.Indian Journal of Chemistry,Vol.41B . 2002 * |
| 新型杀虫剂取代-2-硝基亚氨基-咪唑烷的合成及初步药效试验. 潘英明，陈文纳等.农药，第39卷第1期. 2000 |
| 新型杀虫剂取代-2-硝基亚氨基-咪唑烷的合成及初步药效试验. 潘英明，陈文纳等.农药，第39卷第1期. 2000 * |
| 新型杀虫剂取代-2-硝基亚胺基-咪唑烷的合成及初步药效试验. 潘英明等.Pesticides,Vol.30 No.1. 2000 |
| 新型杀虫剂取代-2-硝基亚胺基-咪唑烷的合成及初步药效试验. 潘英明等.Pesticides,Vol.30 No.1. 2000 * |
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