CN110041289A - A kind of synthetic method of Buprofezin - Google Patents
A kind of synthetic method of Buprofezin Download PDFInfo
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- CN110041289A CN110041289A CN201910406086.0A CN201910406086A CN110041289A CN 110041289 A CN110041289 A CN 110041289A CN 201910406086 A CN201910406086 A CN 201910406086A CN 110041289 A CN110041289 A CN 110041289A
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- buprofezin
- acetate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/34—1,3,5-Thiadiazines; Hydrogenated 1,3,5-thiadiazines
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Abstract
The present invention provides a kind of synthetic method of Buprofezin, include the following steps: that raw material is N- chloromethyl-N-phenyl amino formyl chloride and N- tertiary butyl-N'- isopropylthiourea, using acetate as main component, cyclization reaction obtains acid binding agent.Synthetic method of the invention replaces ammonium hydrogen carbonate as alkali needed for synthesis Buprofezin using sodium acetate, not only solve the carbon dioxide release bring solvent loss problem that ammonium hydrogen carbonate generates during sintetics, side product chlorinated sodium can directly filter removal, and recoverable forms certain economic benefit, the energy consumption of wastewater treatment generation is reduced simultaneously, realize wastewater zero discharge, reach 86% or more by using the average yield that synthetic method of the invention prepares Buprofezin, finished product Buprofezin content is up to 97.0% or more.
Description
Technical field
The present invention relates to the preparation fields of Buprofezin, in particular to a kind of synthetic method of Buprofezin.
Background technique
Buprofezin, also known as buprofezin belong to insect growth regulator, IGR insecticides.By inhibiting chitin synthesis and interference new
Old metabolism prevents pest from normally casting off a skin and abnormal and gradually dead.Have the characteristics that high activity, highly selective, long residual period.
Synthetic method reported at present mainly uses N- chloromethyl-N-phenyl amino formyl chloride (acid chloride intermediate) and N- spy's fourth
Base-N'- isopropylthiourea (fourth propyl thiourea) does alkali in dichloroethanes, toluene equal solvent, with ammonium hydrogen carbonate, carries out cyclization reaction
Preparation.
For example it is reported in patent CN101863859 and two kinds of raw materials of acid chloride intermediate and fourth propyl thiourea is added drop-wise to bicarbonate
Buprofezin is prepared in aqueous ammonium.Patent CN101973962, which is reported, does reaction dissolvent, ammonium bicarbonate aqueous solution using chlorobenzene
Alkali is done, the method that acid chloride intermediate solution is added dropwise after mixing with fourth propyl thiourea prepares Buprofezin.
It is it can be seen that the shortcomings that being all made of ammonium hydrogen carbonate in the prior art does alkali, but use ammonium hydrogen carbonate does alkali: reaction
By-product is carbon dioxide gas and aqueous ammonium chloride solution, and the release of great amount of carbon dioxide gas carries solvent toluene, causes
Toluene loss increases, while the release of carbon dioxide increases carbon emission, is unfavorable for environmental-friendly, and the side product sodium chloride of generation is led
Cause ammonia nitrogen in waste water higher, it is difficult to handle, the industrialized production for limiting the technique is implemented, and the clean manufacturing of product is unfavorable for.
In view of this, the present invention is specifically proposed.
Summary of the invention
The first object of the present invention is to provide a kind of synthetic method of Buprofezin, which is replaced using sodium acetate
Ammonium hydrogen carbonate not only solves the carbon dioxide that ammonium hydrogen carbonate generates in the synthesis process and releases as alkali needed for synthesis Buprofezin
Bring solvent loss problem is put, side product chlorinated sodium can directly filter removal, and recoverable forms certain economy
Benefit, while the energy consumption of wastewater treatment generation is reduced, it realizes wastewater zero discharge, is prepared by using synthetic method of the invention
The average yield of Buprofezin reaches 86% or more, and finished product Buprofezin content is up to 97.0% or more, high income, and purity is good.
In order to realize above-mentioned purpose of the invention, the following technical scheme is adopted:
The present invention provides a kind of synthetic method of Buprofezin, include the following steps: that raw material is N- Chloromethyl-N-phenyl ammonia
Base formyl chloride and N- tertiary butyl-N'- isopropylthiourea, using acetate as main component, cyclization reaction obtains acid binding agent.
In the prior art, patent US101863859 reports that the synthetic method of Buprofezin uses ammonium hydrogen carbonate and does alkali, toluene
Solvent is made, reaction equation is as follows:
Above-mentioned byproduct of reaction is carbon dioxide gas and aqueous ammonium chloride solution, and the release of great amount of carbon dioxide gas is taken
With solvent toluene, toluene loss is caused to increase, while the release of carbon dioxide increases carbon emission, is unfavorable for environmental-friendly.
The generation of aqueous ammonium chloride solution brings the processing problem of high ammonia-nitrogen wastewater.Process above condition limits the industry of current technology
Change and implement, the higher cost of three-protection design is unfavorable for product clean manufacturing.
Therefore, Buprofezin cyclization process method in the prior art is improved, the yield of process gas is reduced, reduces waste water ammonia
Nitrogen content mitigates environmental protection pressure, reduces economic cost, becomes technical problem urgently to be resolved in the prior art.
In view of the three wastes caused by currently used ammonium hydrogen carbonate are difficult to handle, change lye and each material are carried out
The work of dropwise addition mode, if making alkali using sodium hydroxide, due to alkalinity it is stronger, raw material under the reaction conditions stability compared with
Difference, reaction raw materials needs are reacted in the environment of pH value alkali on the weak side, are more advantageous to the progress of reaction, use in the prior art
Alkali be ammonium hydrogen carbonate, but there is pollution greatly in ammonium hydrogen carbonate, the problem of solvent loss, therefore in the solution of the present invention, adopt again
The synthesis of product is carried out with acetate more weaker than sodium hydroxide and sodium carbonate.
In above-mentioned acid binding agent other than acetate, hydroxide may also comprise, the hydroxide is preferably hydroxide
Sodium.
Preferably as further enforceable scheme, acetate is at least one of potassium acetate, sodium acetate.
Preferably as further enforceable scheme, acetate is sodium acetate.
Preferably as further enforceable scheme, acid binding agent is configured to mixing water of the pH between 7.5-12 in advance
Solution, preferably pH control between 8.5-9.
Preferably as further enforceable scheme, the preparation method of the mixed aqueous solution includes: by acetic acid and alkali
20-35 DEG C of mixing, detects pH, and agitation and filtration obtains.
Preferably as further enforceable scheme, the by-product acetic acid that cyclization reaction obtains retrieves after adding alkali
Acetate as acid binding agent to reuse.
Preferably as further enforceable scheme, reaction dissolvent is dichloroethanes or toluene, it is therefore preferable to toluene.
Preferably as further enforceable scheme, N- chloromethyl-N-phenyl amino formyl chloride, N- spy's fourth are first added
Base-N'- isopropylthiourea and reaction dissolvent, are then added dropwise acid binding agent.
Preferably as further enforceable scheme, the matter of the N- chloromethyl-N-phenyl amino formyl chloride and toluene
Amount is than being 1:(2-6).
Preferably as further enforceable scheme, the matter of the N- chloromethyl-N-phenyl amino formyl chloride and toluene
Amount is than being 1:3.
Preferably as further enforceable scheme, the temperature of cyclization reaction is controlled between 30-50 DEG C, time control
System is in 2-7h.
When specific operation, it can carry out in accordance with the following steps, it is sodium acetate that acetate, which specifically uses:
Step 1: the configuration of chloride solution: toluene and acid chloride intermediate are taken, and 20-30min is mixed at room temperature
Sampling is quantitative afterwards, and for the temperature that solution is prepared at 20-35 DEG C, the weight ratio of acid chloride intermediate and toluene is 1:3.
Step 2: the preparation of sodium acetate aqueous solution: acetic acid is added to the water, and sodium hydroxide sodium, control stirring is added portionwise
20-35 DEG C of temperature be sufficiently stirred after survey pH value, pH range 7.5~12.0 stirs 1 hour, to filter after completely dissolution, obtains acetic acid
Sodium water solution.
Step 3: fourth propyl thiourea being added in the toluene solution of acid chloride intermediate, stirs 30min, and temperature is down to 30 DEG C, drop
Add sodium acetate solution, temperature is no more than 35 DEG C；After dripping off sodium acetate solution, 45~50 DEG C are warming up to, keeps the temperature 2~6h.
Step 4: after heat preservation, middle control, after qualified, stirring cooling, temperature is down to 30-35 DEG C, and filtering is floated with toluene
The desalinization of soil by flooding or leaching, gained liquid static layering, water phase processing rear enclosure are used, and oil phase decompression (- 0.095MPa), which is distilled to 110-120 DEG C, steams first
Benzene, cooling are added methanol, are warming up to 60-65 DEG C of 0.5~1h of stirring, have been naturally cooling to a large amount of solids and have been precipitated, then have been dropped with ice water
To 0 DEG C, filtering drying obtains Buprofezin solid.
Compared with prior art, the invention has the benefit that
1) synthetic method of the invention replaces ammonium hydrogen carbonate as alkali needed for synthesis Buprofezin using sodium acetate, not only solves
The carbon dioxide that ammonium hydrogen carbonate of having determined generates during sintetics discharges bring solvent loss problem, side product chlorinated sodium
Removal can be directly filtered, it is simple and convenient；
2) synthetic method of the invention sufficiently lowers the energy consumption of wastewater treatment generation, realizes wastewater zero discharge；
3) average yield that synthetic method of the invention prepares Buprofezin reaches 86% or more, and finished product Buprofezin content reaches
97.0% or more.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the invention.It is not specified in embodiment specific
Condition person carries out according to conventional conditions or manufacturer's recommended conditions.Reagents or instruments used without specified manufacturer is
The conventional products that can be obtained by commercially available purchase.
The present invention provides a kind of synthetic method of Buprofezin, include the following steps: that raw material is N- Chloromethyl-N-phenyl ammonia
Base formyl chloride and N- tertiary butyl-N'- isopropylthiourea, using acetate as main component, cyclization reaction is prepared acid binding agent.
In view of the three wastes caused by currently used ammonium hydrogen carbonate are difficult to handle, change lye and each material are carried out
The work of dropwise addition mode, if making alkali using sodium hydroxide, due to alkalinity it is stronger, raw material under the reaction conditions stability compared with
Difference, reaction raw materials needs are reacted in the environment of pH value alkali on the weak side, are more advantageous to the progress of reaction, use in the prior art
Alkali be ammonium hydrogen carbonate, but there is pollution greatly in ammonium hydrogen carbonate, the problem of solvent loss, therefore in the solution of the present invention, adopt again
The synthesis of product is carried out with acetate more weaker than sodium hydroxide and sodium carbonate.
In above-mentioned acid binding agent other than acetate, hydroxide may also comprise, the hydroxide is preferably hydroxide
Sodium.
Acetate can generate acetic acid along with reaction, and such acetic acid is formed by buffer system (phase with acetate
Compared with previous ammonium hydrogen carbonate, sodium hydroxide system) it is more conducive to the stability of two kinds of raw materials (acyl chlorides, thiocarbamide).
Preferably as further enforceable scheme, acetate is at least one of potassium acetate, sodium acetate.
Preferably as further enforceable scheme, acetate is sodium acetate.
Preferably as further enforceable scheme, acid binding agent is configured to mixing water of the pH between 7.5-12 in advance
Solution, preferably pH control between 8.5-9.
Preferably as further enforceable scheme, the preparation method of the mixed aqueous solution includes: by acetic acid and alkali
20-35 DEG C of mixing, detects pH, and agitation and filtration obtains.
Acid binding agent is configured to mixed aqueous solution in advance, adjusts acid binding agent itself by adjusting the ratio of acetic acid and alkali
PH, when base excess, acid binding agent is the mixture of acetate and alkali, and pH value may be more than 9, when acetic acid is micro- excessive,
PH value may be between 7-8.Alkali is preferably selected sodium hydroxide.
By taking sodium acetate as an example, specific reaction equation is as follows:
In above-mentioned reaction, in addition to purpose product Buprofezin is there are also by-product acetic acid and sodium chloride, sodium chloride passes through simple
Filtering can remove, and acetic acid retrieves acetate to reuse as acid binding agent, by using this hair after can adding alkali
Entire wastewater zero discharge after reaction may be implemented in bright acid binding agent, sufficiently environmentally protective.
Preferably as further enforceable scheme, reaction dissolvent is dichloroethanes or toluene, it is therefore preferable to toluene.
Preferably as further enforceable scheme, N- chloromethyl-N-phenyl amino formyl chloride, N- spy's fourth are first added
Base-N'- isopropylthiourea and reaction dissolvent, are then added dropwise acid binding agent.
If acid binding agent is added earlier than N- chloromethyl-N-phenyl amino formyl chloride, the stability of raw material, institute may be will affect
Preferably finally to add acid binding agent, and carried out preferably with the mode of dropwise addition.
Preferably as further enforceable scheme, the matter of the N- chloromethyl-N-phenyl amino formyl chloride and toluene
Amount is than being 1:(2-6).
Preferably as further enforceable scheme, the matter of the N- chloromethyl-N-phenyl amino formyl chloride and toluene
Amount is than being 1:3.
Preferably as further enforceable scheme, cyclization reaction temperature is controlled between 30-50 DEG C, time control
In 2-7h.
The solution of the present invention is illustrated below by specific embodiment:
Embodiment 1
The synthetic method of Buprofezin carries out in accordance with the following steps:
Sodium acetate aqueous solution is prepared: sodium hydroxide 29g being added in 150g water, acetic acid 41g, control reaction temperature are added dropwise thereto
20-25 DEG C of degree, is added dropwise, and keeps the temperature 15min, obtains sodium acetate aqueous solution 220g, and measurement solution ph is 8.5, for use.
Buprofezin synthesis: 50g acid chloride intermediate (content 93%) is added into 150g toluene, and 40g fourth propyl thiourea is added,
30-35 DEG C of reaction temperature of control is added dropwise sodium acetate aqueous solution 220g, time for adding 0.5 hour, is added dropwise, is warming up to 46 DEG C,
Insulation reaction 2h is cooled to 30 DEG C, and filtering, filtrate stands 15min, layering, and upper organic phase negative pressure precipitation recycles toluene, lower layer
Water phase is collected rear enclosure to be processed and is used, and organic phase precipitation finishes, to precipitation after material 100g methanol is added, be warming up to 60-65 DEG C, entirely
After molten, 30min is kept the temperature, for slow cooling to 0 DEG C, filtering, a small amount of methanol elutes filter cake, Buprofezin finished product 61.8g is obtained after drying,
Content 97.5%, yield 86.5%.
The hydrogen nuclear magnetic resonance modal data for measuring obtained solid product is as follows: 1HNMR (500MHz, d6-CDCl3):7.35-
7.39(t,2H),7.31-7.33(d,2H),7.20-7.24(t,1H),4.76(s,2H),4.60-4.70(m,1H),1.46-
1.49(d,6H),1.33(s,9H)。
Embodiment 2
The synthetic method of Buprofezin carries out in accordance with the following steps:
Sodium acetate aqueous solution recycling is prepared: 20.1g sodium hydroxide is added portionwise in the water phase in Example 1, controls solution
Preparing temperature is 20-25 DEG C, stirs 15min, is removed by filtration the salt of precipitation, obtains sodium acetate solution 251g, and measurement solution ph is
11.5 for use.
Buprofezin synthesis: 50g acid chloride intermediate (content 93%) is added into 150g toluene, and 40g fourth propyl thiourea is added,
30-35 DEG C of reaction temperature of control is added dropwise sodium acetate aqueous solution 251g, time for adding 0.3 hour, is added dropwise, is warming up to 44 DEG C,
Insulation reaction 2h is cooled to 30 DEG C, and filtering, filter cake is eluted with a small amount of toluene, and filtrate stands 15min, layering, and upper organic phase is born
The molten recycling toluene of pressure-off, lower layer's water phase are collected rear enclosure to be processed and are used, and organic phase precipitation finishes, and 100g is added to the material after precipitation
Methanol is warming up to 60-65 DEG C, Quan Ronghou, keeps the temperature 30min, and slow cooling is to 0 DEG C, filtering, and a small amount of methanol elutes filter cake, drying
After obtain Buprofezin finished product 61.3g, content 97.6%, yield 86.0%.
Embodiment 3
The synthetic method of Buprofezin carries out in accordance with the following steps:
Sodium acetate aqueous solution recycling is prepared: 19.5g sodium hydroxide is added portionwise in the water phase in Example 2, controls solution
Preparing temperature is 20-25 DEG C, stirs 15min, and filtering obtains solution 246g, and measurement solution ph is 9.0, for use.
Buprofezin synthesis: 50g acid chloride intermediate (content 93%) is added into 150g toluene, and 40g fourth propyl thiourea is added,
Sodium acetate aqueous solution 246g is added dropwise in 30-35 DEG C of reaction temperature of control, and time for adding 0.2h is added dropwise, and is warming up to 45 DEG C, protects
Temperature reaction 2h, is cooled to 30 DEG C, and filtering, filter cake is eluted with a small amount of toluene, and filtrate stands 15min, layering, upper organic phase negative pressure
Precipitation recycles toluene, and lower layer's water phase is collected rear enclosure to be processed and used, and organic phase precipitation finishes, to precipitation after material 100g first is added
Alcohol is warming up to 60-65 DEG C, Quan Ronghou, keeps the temperature 30min, and slow cooling is to 0 DEG C, and filtering, a small amount of methanol elutes filter cake, after drying
Obtain Buprofezin finished product 61.9g, content 97.8%, yield 87.0%.
Embodiment 4
Other operating procedures and above-described embodiment 1 are consistent, and 29g sodium hydroxide is only replaced with 40.6 potassium hydroxide.
Separated, dry after obtain Buprofezin finished product 61.7g, content 97.2%, yield 86.2%.
Embodiment 5
Other operating procedures and above-described embodiment 1 are consistent, and only the mass ratio of phenyl amino formyl chloride and toluene is 1:
2.5。
Separated, dry after obtain Buprofezin finished product 61.2g, content 97.9%, yield 86.1%.
Embodiment 6
Other operating procedures and above-described embodiment 1 are consistent, and only the mass ratio of phenyl amino formyl chloride and toluene is 1:6.
Separated, dry after obtain Buprofezin finished product 62.1g, content 97.0%, yield 86.6%.
Comparative example 1
The synthetic method of Buprofezin carries out in accordance with the following steps:
Buprofezin synthesis: 50g acid chloride intermediate (content 93%) is added into 150g toluene, and 40g fourth third is then added
Thiocarbamide controls 30-35 DEG C of reaction temperature, ammonium hydrogen carbonate 46.5g is added portionwise, charging finishes, and is warming up to 46 DEG C, insulation reaction
Water 150g is added in 2h, is cooled to 30 DEG C, and filtering, filter cake is eluted with a small amount of toluene, and filtrate stands 15min, is layered, and upper layer is organic
Phase negative pressure precipitation recycles toluene, and lower layer's water phase is collected rear enclosure to be processed and used, and organic phase precipitation finishes, to precipitation after material be added
100g methanol is warming up to 60-65 DEG C, Quan Ronghou, keeps the temperature 30min, and for slow cooling to 0 DEG C, filtering, a small amount of methanol elutes filter cake,
Buprofezin finished product 60.5g, content 97.2%, yield 84.5% are obtained after drying.
Comparative example 2
The synthetic method of Buprofezin carries out in accordance with the following steps:
Buprofezin synthesis: 50g acid chloride intermediate (content 93%) is added into 150g toluene, and 40g fourth third is then added
Thiocarbamide controls 30-35 DEG C of reaction temperature, and 10% sodium hydrate aqueous solution 190g is added dropwise, and charging finishes, and is warming up to 46 DEG C, heat preservation
2h is reacted, is cooled to 30 DEG C, filtering, filter cake is eluted with a small amount of toluene, and filtrate stands 15min, layering, and upper organic phase negative pressure takes off
Molten recycling toluene, lower layer's water phase are collected rear enclosure to be processed and are used, and organic phase precipitation finishes, to precipitation after material 100g methanol is added,
It is warming up to 60-65 DEG C, Quan Ronghou, keeps the temperature 30min, for slow cooling to 0 DEG C, filtering, a small amount of methanol elutes filter cake, obtains after drying
Buprofezin finished product 57.1g, content 96.7%, yield 79.3%.
Although illustrate and describing the present invention with specific embodiment, it will be appreciated that without departing substantially from of the invention
Many other change and modification can be made in the case where spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (10)
1. a kind of synthetic method of Buprofezin, which comprises the steps of: raw material is N- Chloromethyl-N-phenyl amino
Formyl chloride and N- tertiary butyl-N'- isopropylthiourea, for acid binding agent using acetate as main component, cyclization reaction obtains Buprofezin；
It preferably, further include hydroxide in the acid binding agent, the hydroxide is preferably sodium hydroxide；
Preferably, the by-product acetic acid that cyclization reaction obtains retrieves acetate to reuse as acid binding agent after adding alkali.
2. synthetic method according to claim 1, which is characterized in that the acetate be potassium acetate, in sodium acetate extremely
Few one kind.
3. synthetic method according to claim 2, which is characterized in that the acetate is sodium acetate.
4. synthetic method according to claim 1, which is characterized in that reaction dissolvent be dichloroethanes or toluene, preferably
For toluene.
5. synthetic method according to claim 1-4, which is characterized in that the acid binding agent is configured to pH in advance and exists
Mixed aqueous solution between 7.5-12, between preferably pH8.5-9.
6. synthetic method according to claim 5, which is characterized in that the preparation method of the mixed aqueous solution include: by
Acetic acid is mixed with 20-35 DEG C of alkali, detects pH, and agitation and filtration obtains.
7. synthetic method according to claim 1-4, which is characterized in that in N- Chloromethyl-N-phenyl amino first
In the mixed system of acyl chlorides, N- tertiary butyl-N'- isopropylthiourea and reaction dissolvent, the acid binding agent is added dropwise.
8. synthetic method according to claim 1-4, which is characterized in that the N- Chloromethyl-N-phenyl amino
The mass ratio of formyl chloride and toluene is 1:(2-6).
9. synthetic method according to claim 8, which is characterized in that the N- chloromethyl-N-phenyl amino formyl chloride with
The mass ratio of toluene is 1:3.
10. synthetic method according to claim 1-4, which is characterized in that 30-50 DEG C of the temperature of cyclization reaction it
Between, time 2-7h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113651771A (en) * | 2021-08-10 | 2021-11-16 | 安徽广信农化股份有限公司 | Synthesis method of combined buprofezin |
| CN113896691A (en) * | 2020-06-22 | 2022-01-07 | 北京颖泰嘉和生物科技股份有限公司 | Continuous preparation method of buprofezin |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113896691A (en) * | 2020-06-22 | 2022-01-07 | 北京颖泰嘉和生物科技股份有限公司 | Continuous preparation method of buprofezin |
| CN113896691B (en) * | 2020-06-22 | 2023-08-11 | 北京颖泰嘉和生物科技股份有限公司 | Continuous preparation method of buprofezin |
| CN113651771A (en) * | 2021-08-10 | 2021-11-16 | 安徽广信农化股份有限公司 | Synthesis method of combined buprofezin |
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