CN1252036C - Method for producing chloropropham - Google Patents
Method for producing chloropropham Download PDFInfo
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- CN1252036C CN1252036C CN 200410071068 CN200410071068A CN1252036C CN 1252036 C CN1252036 C CN 1252036C CN 200410071068 CN200410071068 CN 200410071068 CN 200410071068 A CN200410071068 A CN 200410071068A CN 1252036 C CN1252036 C CN 1252036C
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- chloro aniline
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- chlorpropham
- chloroaniline
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Abstract
The present invention discloses a method for producing chloropropham, which comprises: firstly, m-chloroaniline is added into an alkali solution under a cooling condition, and isopropyl chloroformate is added after the m-chloroaniline and the alkali solution are uniformly mixed; then, a reaction is carried out at the temperature of 10DEG C to 70DEG C for 0.25 to 4h to obtain the chlorpropham; the molar ratio of the m-chloroaniline to the isopropyl chloroformate to the alkali solution is 1: (0.5 to 2.0): (1 to 1.2). The present invention reduces the reactant charging and the material cost for the production of the chlorpropham by altering the charging sequence; simultaneously, the present invention performs the functions of reaction temperature raising, high energy consumption cooling process omission and reaction time shortening; due to the adoption of high-efficiency liquid chromatography for monitoring the reaction process, the reaction yield is improved to reach higher than 99 %; the discharge amount of waste water is reduced. The present invention has the advantage of simple technology, and simple and convenient operation. The produced chlorpropham with high product purity, which can be further manufactured into medicament forms, such as powder, emulsifiable solutions, aerosols, etc., for storing potatoes as marketable products, has great popularization values and application values.
Description
Technical field
The present invention relates to the production method of compound, particularly relate to the production method of Y 3.
Background technology
The English general chlorpropham by name of Y 3, chemistry 3-chloroanilino isopropyl formate (Isopropyl N-(3-chlorophenyl) carbamate) by name, molecular formula is C
10H
12ClNO
2, molecular weight is 213.66, formula I is its structural formula.Y 3 is a white crystal, and fusing point is 38-41.5 ℃, and the ultraviolet maximum absorption band is 220nm, is insoluble in water, is dissolved in alcohols, aromatic hydrocarbon and most of organic solvent.Y 3 is stable in being lower than 100 ℃ of environment, slowly hydrolysis in acid, alkaline medium.
Y 3 is a kind of fragrant carbamic acid ester class plant-growth regulator, and nineteen fifty-one E.D.Witman etc. has reported its weeding activity, and the same year, exploitation became commodity.This product low toxicity is fed rat with 2000 milligrams of/kilogram skies, has no adverse effects in 2 years.In American-European developed country, the chemistry that always is used as ware potato as over 30 years safely presses down the bud agent.
At present, Y 3 synthetic mainly contains two operational paths: one, carry out condensation reaction with m-chloro aniline and isopropyl chlorocarbonate; Its two, carry out condensation reaction with m-chlorophenyl isocyanate ester and Virahol.The employing m-chlorophenyl isocyanate ester is a raw material, can synthesize Y 3, but because the treating process difficulty of m-chlorophenyl isocyanate ester is bigger, still difficulty is put to practicality at present.Adopt m-chloro aniline and isopropyl chlorocarbonate reaction formula such as II for the synthetic Y 3 of preparation raw material, isopropyl chlorocarbonate and sodium hydroxide solution be added drop-wise to reaction can obtain product after 7-8 hour in the m-chloro aniline, (0-10 ℃) carries out under the pressure cool condition but reaction needs, reaction yield is lower than 95%, there is severe reaction conditions, defectives such as reaction process energy consumption height, time length.
Summary of the invention
The method that the purpose of this invention is to provide a kind of productive rate height, production Y 3 that energy consumption is low.
A kind of method of producing Y 3, under cooling conditions, m-chloro aniline is joined in the alkaline solution earlier, mix the back and add isopropyl chlorocarbonate, react 0.25-4h down at 10-70 ℃ then, obtain Y 3, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, finish reaction; Described m-chloro aniline: isopropyl chlorocarbonate: the mol ratio of alkali is 1: 0.5-2.0: 1-1.2.
Wherein, described alkali sodium hydroxide commonly used or potassium hydroxide, its solution quality percentage concentration is 5%-50%; In order to strengthen mass transfer, the heat transfer in the reaction process, can also contain in the described alkaline solution with the m-chloro aniline mol ratio be 0-10: 1 toluene.
Reaction process can adopt high performance liquid chromatography to detect, when product chromatogram content is not less than 98.5%, and can finish reaction during the m-chloro aniline of noresidue, through obtaining purity at the solid Y 3 more than 98.5% after separation and the drying and other steps.
The present invention has reduced feeding intake of reactant by changing feeding sequence, has reduced the Material Cost that Y 3 is produced.Condensation reaction of the present invention is carried out under 10-70 ℃ of condition, requires reaction to maintain below 5 ℃ with prior art and compares, exempted the high process of cooling of energy consumption, can save a large amount of energy.Under processing condition of the present invention, the speed of response of raw material improves greatly, and the reaction times is 1/16 of prior art only, effectively reduces production cost.Adopt the high-efficient liquid phase chromatogram technique monitoring reaction process, can reach the purpose that raw material all is converted into target compound, improved reaction yield, productive rate can reach more than 99%, and has greatly reduced wastewater discharge.Technology of the present invention is simple, and is easy and simple to handle, and carry out owing to being reflected under the alkaline condition, conversion unit is not had corrosion, and equipment requirements is simple, the reactor that can adopt carbon steel material to make, can avoid the high enamel reactor of use cost, reduce facility investment more than 30%.With the Y 3 product purity height that method of the present invention is produced, cost is low, can be widely used in the storage of potato, has great application value.
Embodiment
Embodiment 1, preparation Y 3
5.23g30% industrial sodium hydroxide solution is joined in 8g water and the 30mL toluene, add the 5.00g m-chloro aniline in cooling with under stirring.After mixing, under the ice-water bath cooling (about 10 ℃), in 15min, drip the 4.80g isopropyl chlorocarbonate continuously.Tear drop is finished, and is warmed up to 70 ℃ of stirring reaction 15min.Sampling detects (the beautiful Fan's energy of the Wang Wen sesame Zhao Yu court of a feudal ruler with high performance liquid chromatograph, " reversed-phased high performace liquid chromatographic detects and presses down bud agent Y 3 in the potato ", Modern Scientific Instruments, 2003,1:59), when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can think that reaction finishes.With the organic layer steam distillation, steam and remove toluene solvant, water layer obtains the solid phase prod Y 3 in cooled and filtered, and output 8.29g, productive rate are 99%.Product detects with high performance liquid chromatography, and purity is 99%.
Embodiment 2, preparation Y 3
6.28930% industrial sodium hydroxide solution is joined in 8g water and the 10mL toluene, add the 5.00g m-chloro aniline in cooling with under stirring.After mixing, under the ice-water bath cooling (about 10 ℃), in 15min, drip the 4.80g isopropyl chlorocarbonate continuously.Tear drop is finished, and is warmed up to 70 ℃ of stirring reaction 15min.Sampling detects with the method for embodiment 1, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can thinks to react and finish.With the organic layer steam distillation, steam and remove toluene solvant, water layer obtains the solid phase prod Y 3 in cooled and filtered, and output 8.29g, productive rate are 99%.Product detects with high performance liquid chromatography, and purity is 99%.
Embodiment 3, preparation Y 3
5.23g30% industrial sodium hydroxide solution is joined in 8g water and the 10mL toluene, add the 5.00g m-chloro aniline in cooling with under stirring.After mixing, under the ice-water bath cooling (about 10 ℃), in 15min, drip the 2.40g isopropyl chlorocarbonate continuously.Tear drop is finished, and is warmed up to 70 ℃ of stirring reaction 15min.Sampling is carried out high performance liquid chromatograph with the method for embodiment 1 and is detected, and when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can thinks to react and finish.With the organic layer steam distillation, steam and remove toluene solvant and reclaim the 2.50g m-chloro aniline, water layer obtains the solid phase prod Y 3 in cooled and filtered, and output 4.14g, productive rate are 99%.Product detects with high performance liquid chromatography, and purity is 99%.
Embodiment 4, preparation Y 3
5.23g30% industrial sodium hydroxide solution is joined in 8g water and the 10mL toluene, add the 5.00g m-chloro aniline in cooling with under stirring.After mixing, bathe under the cooling (about 0 ℃), in 15min, drip the 9.60g isopropyl chlorocarbonate continuously at cryosel.Tear drop is finished, and is warmed up to 70 ℃ of stirring reaction 15min.Sampling detects with the method for embodiment 1, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can thinks to react and finish.With the organic layer steam distillation, steam and remove toluene solvant, water layer obtains the solid phase prod Y 3 in cooled and filtered, and output 8.29g, productive rate are 99%.Product detects with high performance liquid chromatography, and purity is 99%.
Embodiment 5, preparation Y 3
4.59g48% industrial hydrogen potassium oxide solution is joined in 8g water and the 10mL toluene, add the 5.00g m-chloro aniline in cooling with under stirring.After mixing, under the ice-water bath cooling (about 10 ℃), in 15min, drip the 4.80g isopropyl chlorocarbonate continuously.Tear drop is finished, and is warmed up to 70 ℃ of stirring reaction 15min.Sampling detects with the method for embodiment 1, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can thinks to react and finish.With the organic layer steam distillation, steam and remove toluene solvant, water layer obtains the solid phase prod Y 3 in cooled and filtered, and output 8.29g, productive rate are 99%.Product detects with high performance liquid chromatography, and purity is 99%.
Embodiment 6, preparation Y 3
5.23930% industrial sodium hydroxide solution is joined in the 8g water, add the 5.00g m-chloro aniline in cooling with under stirring.After mixing, under the ice-water bath cooling (about 10 ℃), in 15min, drip the 4.80g isopropyl chlorocarbonate continuously.Tear drop is finished, still (about 10 ℃) stirring reaction 4h under the ice-water bath cooling.Sampling detects with the method for embodiment 1, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can thinks to react and finish.Reactant is tied up to cooled and filtered, obtain the solid phase prod Y 3, output 8.29g, productive rate are 99%.Product detects with high performance liquid chromatography, and purity is 99%.
Embodiment 7, preparation Y 3
550kg30% industrial sodium hydroxide solution is joined in the 200-800kg water, add the 500kg m-chloro aniline in cooling with under stirring.After mixing, under the recirculated water cooling (about 20 ℃), continuous Dropwise 5 30kg isopropyl chlorocarbonate, the dropping process is kept temperature of reaction system and is no more than 40 ℃.Tear drop is finished, and is warmed up to 60 ℃ of stirring reaction 1h.Sampling detects with the method for embodiment 1, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, can thinks to react and finish.Organic layer is washed with 1200L hot water (60 ℃) violent stirring, and organic layer is emitted leaving standstill back decline.Cooling, obtain the about 830kg of solid phase prod Y 3, productive rate 99% after turning over the 72h that dries in the air.Product detects with high performance liquid chromatography, and purity is 99%.
Claims (6)
1, a kind of method of producing Y 3, under cooling conditions, m-chloro aniline is joined in the alkaline solution earlier, mix the back and add isopropyl chlorocarbonate, react 0.25-4h down at 10-70 ℃ then, obtain Y 3, when product chromatogram content is not less than 98.5%, and during the m-chloro aniline of noresidue, finish reaction; Described m-chloro aniline: isopropyl chlorocarbonate: the mol ratio of alkali is 1: 0.5-2.0: 1-1.2.
2, method according to claim 1 is characterized in that: described alkaline solution is sodium hydroxide or potassium hydroxide solution.
3, method according to claim 2 is characterized in that: described sodium hydroxide or potassium hydroxide solution mass percentage concentration are 5%-50%.
4, according to claim 1 or 2 or 3 described methods, it is characterized in that: can also contain in the described alkaline solution with the m-chloro aniline mol ratio be 0-10: 1 toluene is as solvent.
5, according to claim 1 or 2 or 3 described methods, it is characterized in that: the described Y 3 that obtains also through after separation and the drying, obtains product.
6, method according to claim 4 is characterized in that: the described Y 3 that obtains obtains product after also desolventizing toluene and drying through steaming.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410071068 CN1252036C (en) | 2004-07-28 | 2004-07-28 | Method for producing chloropropham |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410071068 CN1252036C (en) | 2004-07-28 | 2004-07-28 | Method for producing chloropropham |
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|---|---|
| CN1587256A CN1587256A (en) | 2005-03-02 |
| CN1252036C true CN1252036C (en) | 2006-04-19 |
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| CN 200410071068 Expired - Fee Related CN1252036C (en) | 2004-07-28 | 2004-07-28 | Method for producing chloropropham |
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| CN102167670B (en) * | 2011-03-23 | 2013-04-24 | 南通泰禾化工有限公司 | Method for producing chlorpropham |
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