CN102600761B - Surface active substance taking N-(4-nitrobenzophenone)-5-chlorosamide as parent, and preparation technology - Google Patents
Surface active substance taking N-(4-nitrobenzophenone)-5-chlorosamide as parent, and preparation technology Download PDFInfo
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- CN102600761B CN102600761B CN201110022202.2A CN201110022202A CN102600761B CN 102600761 B CN102600761 B CN 102600761B CN 201110022202 A CN201110022202 A CN 201110022202A CN 102600761 B CN102600761 B CN 102600761B
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Abstract
The invention relates to a surface active substance taking N-(4-nitrobenzophenone)-5-chlorosamide as a parent, and a preparation technology. The surface active substance prepared by the invention is obtained by the steps of taking N-(4-nitrobenzophenone)-5-chlorosamide as parent; reacting with epoxy low molecular weight compounds such as ethylene oxide, 1,2-epoxypropane, 2,3-epoxy butane and so on under action of a catalyst, thus, forming the surface active substance capable of diffusing to form a film on the water. After the surface active substance is put into the water, the surface active substance can diffuse quickly and automatically and then form a compact molecular film on the water, which floats on the water surface and has good killing effect for Schistosome cercaria on the water.
Description
Technical field
The present invention relates to the surfactant with N- (4- nitrobenzophenone) -5- chlorosamide as parent for the one kind and its system
Standby technology, belongs to field of fine chemical.
Background technology
N- (4- nitrobenzophenone) -5- chlorosamide, is a kind of light yellow crystalline powder, is practically insoluble in water, insoluble
In acid, it is slightly soluble in ethanol, acetone, be dissolved in dilute sodium hydrate aqueous solution, dimethyl sulfoxide and amine solution.4 '-nitro -2 ', 5-
Dichloro N-phenylsalicylamide can be used as molluscacide, also has killing action to schistosomulum, miracidium.Schistosomulum is mostly with static state
Mode swims on the water surface, during with N- (4- nitrobenzophenone) -5- chlorosamide directly as larvacide, due to easily analysing in water
Go out, settle, not only the big polluted-water of consumption, and drug effect is poor.
The present invention provides a kind of surfactant with N- (4- nitrobenzophenone) -5- chlorosamide as parent and its system
Standby technology, this surface-active substance confrontation schistosomulum has good killing effect.
Content of the invention
It is an object of the invention to provide one kind is with N- (4- nitrobenzophenone) surface-active substance as the parent for -5- chlorosamide
Matter and its technology of preparing.
Technology of preparing provided by the present invention is：In molar ratio by 1 part of 4 '-nitro -2 ', 5- dichloro N-phenylsalicylamide adds
In reactor, after being heated with stirring to 40～100 DEG C, add 1 part of catalyst, stir, be passed through nitrogen by after reactor evacuation
Gas shielded, in triplicate, is subsequently adding 4～20 parts of epoxiess micromolecular compound, isothermal reaction 24～72 hours, is cooled to
Room temperature, after adding water, with dichloromethane extraction, is dried, removes solvent, that is, obtain the surfactant of different molecular weight distribution.
The main component of catalyst described in invention is by sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, diethyl
Zinc, triethyl aluminum, butyl lithium composition, can be single compound or mixture.
Epoxy micromolecular described in invention, refer to oxirane, 1,2 epoxy prapane, 1,2- epoxy butane, 2,3-
Epoxy butane.
After surfactant prepared by the present invention meets water, you can automatically spread on the water surface and formed one layer fine and close
Molecular film, swims in surface layer of water.This molecular film has good killing to perching in the schistosomulum of water surface
Effect.
Specific embodiment
With reference to specific embodiment, the invention will be further described, but the present invention is not limited to following examples.
Experimental technique described in following embodiments, if no special instructions, is conventional method；Described reagent and material, all
Commercially obtain.
Embodiment 1
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 80 DEG C, add 1 part of carbon
Sour sodium, as catalyst, stirs, and is passed through nitrogen after evacuation, in triplicate, is passed through 3 parts of oxirane, 80 DEG C of reactions
24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off solvent and obtain N- (4- nitrobenzophenone) -5- chlorine
Salicylamide surfactant.Obtained surfactant is put into after the water surface containing schistosomulum, finds 45
In minute, cercaria mortality rate is 98%.
Embodiment 2
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 85 DEG C, add 1 part of carbon
Potassium hydrogen phthalate and triethyl aluminum mixture, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, add 6 part 1,
2- expoxy propane.85 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off solvent and obtain
N- (4- nitrobenzophenone) -5- chlorosamide surfactant.Obtained surfactant is put into containing schistosomicide
After the water surface of cercaria, find 60 minutes in, cercaria mortality rate is 96%.
Embodiment 3
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 90 DEG C, add 1 part of carbon
Sour sodium and diethyl zinc mixture, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, add 8 part 2,3-
Epoxy butane.90 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off solvent and obtain N-
(4- nitrobenzophenone) -5- chlorosamide surfactant.Obtained surfactant is put into containing schistosomicide tail
After the water surface of the larva of a tapeworm or the cercaria of a schistosome, find 90 minutes in, cercaria mortality rate is 98%.
Embodiment 4
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 95 DEG C, add 1 part of carbon
Sour potassium and butyl lithium, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, successively add 5 parts of oxirane
With 5 parts of 1,2- epoxy butanes.95 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off molten
Agent obtains N- (4- nitrobenzophenone) -5- chlorosamide surfactant.By obtained surfactant put into containing
After the water surface of schistosomulum, find 120 minutes in, cercaria mortality rate is 92%.
Embodiment 5
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 60 DEG C, add 1 part of carbon
Potassium hydrogen phthalate and butyl lithium, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, add 10 parts of 1,2- epoxies
Propane.60 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off solvent and obtain N- (4- nitre
Base phenyl) -5- chlorosamide surfactant.Obtained surfactant is put into the water containing schistosomulum
Behind face, find 120 minutes in, cercaria mortality rate is 90%.
Embodiment 6
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 100 DEG C, add 1 part
Sodium bicarbonate and triethyl aluminum, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, add 20 part 1,2-
Epoxy butane.100 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off solvent and obtain N-
(4- nitrobenzophenone) -5- chlorosamide surfactant.Obtained surfactant is put into containing schistosomicide tail
After the water surface of the larva of a tapeworm or the cercaria of a schistosome, find 150 minutes in, cercaria mortality rate is 90%.
Embodiment 7
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 50 DEG C, add 1 part of carbon
Sour potassium and butyl lithium, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, successively add 2 parts of 1,2- epoxies
Propane and 2 parts of 2,3- epoxy butanes.50 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, steam
Solvent is gone to obtain N- (4- nitrobenzophenone) -5- chlorosamide surfactant.Obtained surfactant is put into
After the water surface containing schistosomulum, find 60 minutes in, cercaria mortality rate is 95%.
Embodiment 8
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 100 DEG C, add 1 part
Potassium carbonate and triethyl aluminum, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, successively add 4 parts of epoxies
Ethane and 16 parts of 1,2- epoxy butanes.100 DEG C of reaction 48h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried,
Boil off solvent and obtain N- (4- nitrobenzophenone) -5- chlorosamide surfactant.Obtained surfactant is put
After entering the water surface containing schistosomulum, find 120 minutes in, cercaria mortality rate is 90%.
Embodiment 9
Take 1 part of N- (4- nitrobenzophenone) -5- chlorosamide to add in reactor, be heated with stirring to 85 DEG C, add 1 part of carbon
Sour potassium and diethyl zinc, as catalyst, stir, and are passed through nitrogen after evacuation, in triplicate, add 8 parts of 1,2- epoxy fourths
Alkane.85 DEG C of reaction 24h, cooling, add water, with dichloromethane extraction, be washed to neutrality, be dried, boil off solvent and obtain N- (4- nitro
Phenyl) -5- chlorosamide surfactant.Obtained surfactant is put into the water surface containing schistosomulum
Afterwards, find 60 minutes in, cercaria mortality rate is 95%.
Claims (2)
1. one kind is with the technology of preparing of N- (4- nitrobenzophenone) surfactant as the parent for -5- chlorosamide, its feature
It is：With N- (4- nitrobenzophenone) -5- chlorosamide molecule as parent, under catalyst action, with epoxy micromolecular
Compound react, formed can on the water surface self-diffusion film forming surfactant；Described epoxy micromolecular refers to epoxy second
Alkane, 1,2 epoxy prapane, 1,2- epoxy butane, 2,3- epoxy butane；
In molar ratio 1 part of N- (4- nitrobenzophenone) -5- chlorosamide is added in reactor, be heated with stirring to 40-100 DEG C
Afterwards, add 1 part of catalyst, stir, nitrogen protection will be passed through after reactor evacuation, in triplicate, be subsequently adding 4-20
The epoxiess micromolecular compound of part, isothermal reaction 24 hours, it is cooled to room temperature, after adding water, with dichloromethane extraction, be dried,
Remove solvent, that is, obtain the surfactant of different molecular weight distribution.
2. one kind according to claim 1 is with N- (4- nitrobenzophenone) surface-active substance as the parent for -5- chlorosamide
The technology of preparing of matter it is characterised in that：The main component of catalyst be by sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate,
Diethyl zinc, triethyl aluminum, butyl lithium composition.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110022202.2A CN102600761B (en) | 2011-01-20 | 2011-01-20 | Surface active substance taking N-(4-nitrobenzophenone)-5-chlorosamide as parent, and preparation technology |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110022202.2A CN102600761B (en) | 2011-01-20 | 2011-01-20 | Surface active substance taking N-(4-nitrobenzophenone)-5-chlorosamide as parent, and preparation technology |
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| CN102600761B true CN102600761B (en) | 2017-02-08 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101002553A (en) * | 2006-01-20 | 2007-07-25 | 赣南师范学院 | High efficiency agent for preventing and controlling shistosomulum, and preparing technique therefor |
| CN101712600A (en) * | 2008-10-07 | 2010-05-26 | 抚顺佳化聚氨酯有限公司 | Method for preparing ethylene glycol phenyl ether, propylene glycol phenyl ether and butylene glycol phenyl ether |
-
2011
- 2011-01-20 CN CN201110022202.2A patent/CN102600761B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101002553A (en) * | 2006-01-20 | 2007-07-25 | 赣南师范学院 | High efficiency agent for preventing and controlling shistosomulum, and preparing technique therefor |
| CN101712600A (en) * | 2008-10-07 | 2010-05-26 | 抚顺佳化聚氨酯有限公司 | Method for preparing ethylene glycol phenyl ether, propylene glycol phenyl ether and butylene glycol phenyl ether |
Non-Patent Citations (1)
| Title |
|---|
| "Synthesis and cercaricidal activities of a serial of novel self-diffused cercaricides derived from niphensamide";Wei Guo et al.;《Chinese Chemical Letters》;20081231;第19卷(第4期);406–408 * |
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