CN103936550A - Preparation method of 3,4,5-trichlorobenzotrifluoride - Google Patents
Preparation method of 3,4,5-trichlorobenzotrifluoride Download PDFInfo
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- CN103936550A CN103936550A CN201410058115.6A CN201410058115A CN103936550A CN 103936550 A CN103936550 A CN 103936550A CN 201410058115 A CN201410058115 A CN 201410058115A CN 103936550 A CN103936550 A CN 103936550A
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Abstract
The invention discloses a preparation method of 3,4,5-trichlorobenzotrifluoride. The preparation method comprises steps of chlorination, fluorination, rectification, and neutralization and filtration, and 3,4,5-trichlorobenzotrifluorideis obtained via the processing steps. Raw materials of the preparation method are widely available, and are low in cost, so that production cost of the target compound is reduced, economic benefits are increased, using of a large amount of sulfuric acid and nitric acid is avoided, corrosion of equipment is less, pollution is reduced greatly, and environmental harm is reduced. In addition, ferric chloride anhydrous is used as a catalyst in the preparation processes, so that cost is low, efficiency is high, reaction is mild, and potential safety hazard and side reaction caused by excessively fierce reaction are avoided, wherein the excessively fierce reaction is caused by catalysts with excessively high activity.
Description
Technical field
The present invention relates to a kind of preparation method of pesticide chemical product, be specifically related to p-chloro benzo trifluoride-99 be raw material, through chlorination, fluoridize, rectifying, neutralization obtains 3,4,5-trichlorobenzotrifluoride.
Background technology
3,4,5-trichlorobenzotrifluoride is colourless oil liquid.200～202 DEG C of boiling points, 98 DEG C of flash-points, relative density 1.600, refractive index 1.5000.Aromatic fluorine compound is the important intermediate of the physiologically active compounds such as medicine, agricultural chemicals.Because fluorine atom volume is little, electronegativity is large, and cloud density is high, the introducing of fluorine atom or fluoro-containing group, make compound there is good thermostability, antioxidant, drug effect strengthens, effect is lasting, the advantages such as reduced side effects, therefore extremely people's concern of the research and development of fluorine-containing medicines, agricultural chemicals.
Existing synthetic method is as follows:
1) phenylfluoroform chlorination process
This method is taking phenylfluoroform as starting raw material, makes catalyzer by FERRIC CHLORIDE ANHYDROUS, reacts in 80～130 DEG C with chlorine, generates the mixture of the trichlorine that is difficult to separate, dichloro, a chlorobenzotrifluoride, and aftertreatment is more difficult.
2) parachlorotoluene chlorination process
This method is taking parachlorotoluene as starting raw material, after parachlorotoluene side chain optical chlorinating reaction, generates chlorine benzenyl trichloride, reacts with Finkelstein, with anhydrous hydrogen fluoride as fluorizating agent, generate p-chloro benzo trifluoride-99, then, under FERRIC CHLORIDE ANHYDROUS catalysis, obtain target compound with chlorine reaction.
3) chloro denitration method
Day disclosure special permission 60-158142 is with 3,5-dinitrobenzene-4-chlorobenzotrifluoride for raw material, and iron trichloride, aluminum chloride, phenyl-sulfhydrate compounds are co-catalysis agent, 200 DEG C of logical chlorine in left and right, and chloro denitration under high temperature, directly generates 3,4,5-trichlorobenzotrifluoride.But the reaction times reaches 97 hours, yield is not high.
Chinese patent CN1086374C discloses a kind of method, above reactor, access the rectifying tower of a preparation condenser, reaction product is made to rectifying separation, 3,5-dinitrobenzene-4-chlorobenzotrifluoride is raw material, is warming up to 190～250 DEG C and passes into chlorine reaction and obtain target compound.
Above-mentioned these method temperature of reaction are high, the time is long, processing condition harshness, complex steps, and react raw material 4-chloro-3 used, 5-dinitro-p-trifluorotoluene, a large amount of sulfuric acid, nitric acid of using is as raw material, large to the corrodibility of equipment, and pollutes, endangers environment.Can not meet environment, economical effects.In addition, taking p-chloro benzo trifluoride-99 as raw material, produce 3,4-, bis-chlorobenzotrifluorides, by-product is 3,4,5-trichlorobenzotrifluoride, but general content is in 1.5% left and right, and target compound is not had to use value.
Summary of the invention
Technical problem to be solved by this invention is: provide a kind of simple and convenient process for preparing of 3,4,5-trichlorobenzotrifluoride, taking p-chloro benzo trifluoride-99 as raw material, through chlorination, fluoridize, rectifying, neutralization obtains 3,4,5-trichlorobenzotrifluoride, reactions steps is easy, and cost is low, pollutes little.
For addressing the above problem, the technical solution used in the present invention is: a kind of 3, 4, the preparation method of 5-trichlorobenzotrifluoride, the steps include: to produce 3, when 4-bis-chlorobenzotrifluoride, in chlorination workshop section adjusting process condition, after reaction 4 hours, temperature is increased to 110 DEG C, continuing logical chlorine to reaction finishes, the method by-product 3, 4, 5-trichlorobenzotrifluoride content generally can reach in 8～10% left and right, afterwards again by 3, after 4-bis-chlorobenzotrifluoride rectifying out, form containing 3, 4, the rectification residue of 5-trichlorobenzotrifluoride, repeat afterwards rectifying, generally rectifying for the first time can arrive 70～80%, rectifying for the second time can reach more than 96%.
Technical solution detailed step of the present invention is as follows:
1) chlorination: 3,4-toluene dichloride is dropped in reactor, be warmed up to 95 DEG C, add after FERRIC CHLORIDE ANHYDROUS catalyzer, start to pass into dry chlorine, flow 40～80m
3/ h, after reacting 4 hours, is increased to 110～115 DEG C by temperature, continues logical chlorine and carries out chlorination reaction 20～24 hours, and reaction finishes; Pass into dry air and discharge hydrogen chloride gas and the gaseous impurities of unreacted chlorine in reactor, reaction generation, obtain the mixture of 3,4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichlorides;
2) fluoridize: by step 1) gained 3, 4-trichloro toluene dichloride and 3, 4, the mixture of 5-tri-chlorobenzotrichlorides and anhydrous hydrogen fluoride are pressed in reactor and (check the unlatching situation of each valve), open and stir, in chuck, slowly pass into steam, in the time that reaching 1.5MPa, still internal pressure opens exhaust emissions valve exhaust, continue to heat up, control temperature in the kettle being 110～115 DEG C is 1.5～2.5MPa with still internal pressure, sampling analysis when still internal pressure no longer rises when not needing exhaust, 3, 4, when reaching 8～10%, opens 5-trichlorobenzotrifluoride content exhaust relief valve pressure release (time of fluoridation is 4～10 hours), after pressure release finishes, in reactor, pass into hydrogen chloride gas and the gaseous impurities that dry air is discharged unreacted hydrogen fluoride in reactor, reacted generation, obtain the mixture of 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride,
3) rectifying: step 2) mixture that obtains, after 3,4-, bis-chlorobenzotrifluoride rectifying out, form the rectification residue containing 3,4,5-trichlorobenzotrifluoride, repeat afterwards rectifying, generally rectifying for the first time can arrive 70～80%, and rectifying for the second time can reach more than 96%;
4) neutralization packaging: more than the purity 96wt% that step 3) is obtained 3,4, during 5-trichlorobenzotrifluoride proceeds to and still, add soda ash, open to stir to neutralize after pH presents neutrality (pH=6.8～7.2 conventionally) and filter, then pack 3,4,5-trichlorobenzotrifluoride finished product.
In step 1) chlorination process, described 3, the mass ratio of 4-toluene dichloride and catalyzer is 1:0.01～0.05.
Step 2) in fluorination process, described 3,4-trichloro toluene dichloride and hydrofluoric mol ratio are 1:3～3.5.
Described in step 3), rectifying condition is: reflux ratio 5:2～3:1, collect the cut of 199～202 DEG C of top gaseous phase temperature, and after condensation, obtain target compound.
Chemical equation of the present invention is:
Owing to having adopted technique scheme, beneficial effect of the present invention:
1) the present invention's raw material used has been avoided a large amount of uses of sulfuric acid, nitric acid, little to the corrodibility of equipment, has greatly reduced pollution, has reduced the harm to environment.
2) raw material 3 that the present invention uses, 4-toluene dichloride wide material sources, cheap, can reduce the production cost of target compound, increase economic efficiency.
3) the present invention's FERRIC CHLORIDE ANHYDROUS catalyzer used, cost is low, efficiency is high, reaction temperature and, avoided the catalyzer of hyperactivity to make the too fierce potential safety hazard causing of reaction, and the increasing of other side reaction.
4) the present invention, by regulating reaction conditions that 3,4,5-trichlorobenzotrifluoride content is reached 8～10%, separates 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride by rectifying, easy and simple to handle.
Embodiment
The present invention will be further described for the following examples, its objective is and can better understand content of the present invention.But the scope that embodiment does not limit the present invention in any way.The improvement that the technician of this professional domain makes within the scope of the claims in the present invention and adjustment also should belong to right of the present invention and protection domain.
Embodiment 1
1) chlorination: by 800g3,4-toluene dichloride drops in 3L reactor, is warmed up to 95 DEG C, adds 20g catalyzer, starts to pass into dry chlorine, flow 40～80m
3/ h, after reacting 4 hours, is increased to 110 DEG C by temperature, continues logical chlorine and finishes to reacting for 20 hours.Pass into dry air and discharge hydrogen chloride gas and the gaseous impurities of unreacted chlorine in reactor, reaction generation, obtain 3,4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures.
2) fluoridize: by previous step react obtain 3, the anhydrous hydrogen fluoride of 4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures and 12 moles is pressed in 3L reactor, checks the unlatching situation of each valve.Open and stir, in chuck, slowly pass into steam, in the time that reaching 1.5MPa, still internal pressure opens exhaust emissions valve exhaust, continue to heat up until 110 DEG C of temperature in the kettle, control still internal pressure 1.5～1.7MPa, sampling analysis when still internal pressure no longer rises when not needing exhaust, 3 simultaneously, 4,5-trichlorobenzotrifluoride content reaches opens exhaust relief valve pressure release 8～10% time.After pressure release finishes, in reactor, pass into hydrogen chloride gas and the gaseous impurities that dry air is discharged unreacted hydrogen fluoride in reactor, reacted generation, obtain 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride mixture.
3) rectifying: under reflux ratio 5:2 condition, the mixture that second step obtains is by after 3,4-, bis-chlorobenzotrifluoride rectifying out, form the rectification residue containing 3,4,5-trichlorobenzotrifluoride, repeat afterwards rectifying, collect the cut of 199～202 DEG C of top gaseous phase temperature, after condensation, obtain target compound.Generally rectifying for the first time can arrive 70～78%, and rectifying for the second time can reach more than 96%.
4) neutralization packaging: by more than purity 96wt% 3,4, during 5-trichlorobenzotrifluoride proceeds to and still, add a certain amount of soda ash, open and stir neutralization and present after neutrality through filtration to pH, then pack 3,4,5-trichlorobenzotrifluoride finished product.
Embodiment 2
1) chlorination: by 800g3,4-toluene dichloride drops in 3L reactor, is warmed up to 95 DEG C, adds 40g catalyzer, starts to pass into dry chlorine, flow 40～80m
3/ h, after reacting 4 hours, is increased to 115 DEG C by temperature, continues logical chlorine and finishes to reacting for 16 hours.Pass into dry air and discharge hydrogen chloride gas and the gaseous impurities of unreacted chlorine in reactor, reaction generation, obtain 3,4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures.
2) fluoridize: by previous step react obtain 3, the anhydrous hydrogen fluoride of 4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures and 14 moles is pressed in 3L reactor, checks the unlatching situation of each valve.Open and stir, in chuck, slowly pass into steam, in the time that reaching 1.5MPa, still internal pressure opens exhaust emissions valve exhaust, continue to heat up until 115 DEG C of temperature in the kettle, control still internal pressure 2.2～2.5MPa, sampling analysis when still internal pressure no longer rises when not needing exhaust, 3 simultaneously, 4,5-trichlorobenzotrifluoride content reaches opens exhaust relief valve pressure release 8～10% time.After pressure release finishes, in reactor, pass into hydrogen chloride gas and the gaseous impurities that dry air is discharged unreacted hydrogen fluoride in reactor, reacted generation, obtain 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride mixture.
3) rectifying: under reflux ratio 3:1 condition, the mixture that second step obtains is by after 3,4-, bis-chlorobenzotrifluoride rectifying out, form the rectification residue containing 3,4,5-trichlorobenzotrifluoride, repeat afterwards rectifying, collect the cut of 199～202 DEG C of top gaseous phase temperature, after condensation, obtain target compound.Generally rectifying for the first time can arrive 78～80%, and rectifying for the second time can reach more than 96%.
4) neutralization packaging: by more than purity 96wt% 3,4, during 5-trichlorobenzotrifluoride proceeds to and still, add a certain amount of soda ash, open and stir neutralization and present after neutrality through filtration to pH, then pack 3,4,5-trichlorobenzotrifluoride finished product.
Embodiment 3
1) chlorination: by 800g3,4-toluene dichloride drops in 3L reactor, is warmed up to 95 DEG C, adds 8g catalyzer, starts to pass into dry chlorine, flow 40～80m
3/ h, controls 115～115 DEG C of temperature, continues logical chlorine and finishes to reacting for 18 hours.Pass into dry air and discharge hydrogen chloride gas and the gaseous impurities of unreacted chlorine in reactor, reaction generation, obtain 3,4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures.
2) fluoridize: by previous step react obtain 3, the anhydrous hydrogen fluoride of 4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures and 13 moles is pressed in 3L reactor, checks the unlatching situation of each valve.Open and stir, in chuck, slowly pass into steam, in the time that reaching 1.5MPa, still internal pressure opens exhaust emissions valve exhaust, continue to heat up until 110 DEG C of temperature in the kettle, control still internal pressure 1.8～2.0MPa, sampling analysis when still internal pressure no longer rises when not needing exhaust, 3 simultaneously, 4,5-trichlorobenzotrifluoride content reaches opens exhaust relief valve pressure release 8～10% time.After pressure release finishes, in reactor, pass into hydrogen chloride gas and the gaseous impurities that dry air is discharged unreacted hydrogen fluoride in reactor, reacted generation, obtain 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride mixture.
3) rectifying: under reflux ratio 3:1 condition, the mixture that second step obtains is by after 3,4-, bis-chlorobenzotrifluoride rectifying out, form the rectification residue containing 3,4,5-trichlorobenzotrifluoride, repeat afterwards rectifying, collect the cut of 199～202 DEG C of top gaseous phase temperature, after condensation, obtain target compound.Generally rectifying for the first time can arrive 72～76%, and rectifying for the second time can reach more than 96%.
4) neutralization packaging: by more than purity 96wt% 3,4, during 5-trichlorobenzotrifluoride proceeds to and still, add a certain amount of soda ash, open and stir neutralization and present after neutrality through filtration to pH, then pack 3,4,5-trichlorobenzotrifluoride finished product.
Embodiment 4
1) chlorination: by 600kg3,4-toluene dichloride drops in 3000L reactor, is warmed up to 95 DEG C, adds 8.0kg catalyzer, starts to pass into dry chlorine, flow 40～80m
3/ h, controls 110～115 DEG C of temperature, continues logical chlorine and finishes to reacting for 16 hours.Pass into dry air and discharge hydrogen chloride gas and the gaseous impurities of unreacted chlorine in reactor, reaction generation, obtain 3,4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures.
2) fluoridize: by previous step react obtain 3, the anhydrous hydrogen fluoride of 4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichloride mixtures and 250kg is pressed in 3000L reactor, checks the unlatching situation of each valve.Open and stir, in chuck, slowly pass into steam, in the time that reaching 1.5MPa, still internal pressure opens exhaust emissions valve exhaust, continue to heat up until 110～115 DEG C of temperature in the kettle, control still internal pressure 1.5～2.5MPa, sampling analysis when still internal pressure no longer rises when not needing exhaust, 3 simultaneously, 4,5-trichlorobenzotrifluoride content reaches opens exhaust relief valve pressure release 8～10% time.After pressure release finishes, in reactor, pass into hydrogen chloride gas and the gaseous impurities that dry air is discharged unreacted hydrogen fluoride in reactor, reacted generation, obtain 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride mixture.
3) rectifying: under reflux ratio 3:1 condition, the mixture that second step obtains is by 3, after 4-bis-chlorobenzotrifluoride rectifying out, form the rectification residue containing 3,4,5-trichlorobenzotrifluoride, repeat afterwards rectifying, the cut of collecting 199～202 DEG C of top gaseous phase temperature, obtains target compound after condensation, content is more than 96%.
4) neutralization packaging: by more than purity 96wt% 3,4, during 5-trichlorobenzotrifluoride proceeds to and still, add a certain amount of soda ash, open and stir neutralization and present after neutrality through filtration to pH, then pack 3,4,5-trichlorobenzotrifluoride finished product.
Gas product facies analysis condition:
Method: gas chromatographic analysis (GC);
Detector: flame ionization ditector;
Chromatogram lives in OV-1,30m*0.32mm*0.5 μ m;
Carrier gas: 99.99% high pure nitrogen;
Column temperature: 140 DEG C;
Vaporization temperature: 220 DEG C;
Detector temperature: 220 DEG C;
Calculate: area normalization method;
According to above-mentioned condition, products obtained therefrom is analyzed, generally about 4.3 minutes, gone out 3,4,5-trichlorobenzotrifluoride main peak (consistent with standard specimen spectrogram), content >=96%.
Claims (9)
1. one kind 3,4, the preparation method of 5-trichlorobenzotrifluoride, its step comprises:
1) chlorination: for starting raw material, under catalyzer exists, carry out chlorination reaction with chlorine with 3,4-toluene dichloride, obtain the mixture of 3,4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichlorides;
2) fluoridize: by step 1) gained 3, mixture and the anhydrous hydrogen fluoride of 4-trichloro toluene dichloride and 3,4,5-, tri-chlorobenzotrichlorides carry out fluoridation, obtain the mixture of 3,4-, bis-chlorobenzotrifluorides and 3,4,5-trichlorobenzotrifluoride;
3) rectifying: step 2) mixture that obtains is through rectifying, obtains 3,4,5-trichlorobenzotrifluoride.
2. according to claim 1 a kind of 3, the preparation method of 4,5-trichlorobenzotrifluoride, is characterized in that: described 3,4, the preparation process of 5-trichlorobenzotrifluoride also comprises neutralization packaging: soda ash is added to step 3) obtains 3,4, in 5-trichlorobenzotrifluoride product, regulate pH to filter after neutral, obtain 3,4,5-trichlorobenzotrifluoride finished product.
3. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: in step 1) chlorination process, described catalyzer is FERRIC CHLORIDE ANHYDROUS.
4. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: in step 1) chlorination process, described 3, the mass ratio of 4-toluene dichloride and catalyzer is 1:0.01～0.05.
5. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: step 2) in fluorination process, described 3,4-trichloro toluene dichloride and hydrofluoric mol ratio are 1:3～3.5.
6. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: the chlorination reaction temperature described in step 1) is 110～115 DEG C, and the chlorination reaction time is 20～24 hours; Step 2) described fluorination reaction temperature is that 110～115 DEG C, pressure are 1.5～2.5MPa, the time of fluoridation is 4～10 hours.
7. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: in the chlorination reaction process described in step 1), chlorine flowrate is 40～80m
3/ h.
8. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: the rectifying condition described in step 3) is: reflux ratio 5:2～3:1, collects the cut of 199～202 DEG C of top gaseous phase temperature.
9. according to claim 1 and 2 a kind of 3,4, the preparation method of 5-trichlorobenzotrifluoride, is characterized in that: described quality product percentage composition reaches 96% when above, and rectifying finishes.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106892792A (en) * | 2017-03-18 | 2017-06-27 | 山东道可化学有限公司 | A kind of method for continuously synthesizing and its synthesis device of 3,4 2 chlorobenzotrifluoride |
| CN110317150A (en) * | 2019-07-30 | 2019-10-11 | 江苏超跃化学有限公司 | A method of preparing 3,4- dichlorobenzonitrile |
| CN115055144A (en) * | 2022-07-15 | 2022-09-16 | 常州新东化工发展有限公司 | System and process for producing o-chlorotrifluoromethylene |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1528052A1 (en) * | 2003-10-29 | 2005-05-04 | FINCHIMICA S.p.A. | Process for the production of 4-amino-3,5-dichlorobenzotrifluoride with high purity commercial products being obtained in parallel |
-
2014
- 2014-02-21 CN CN201410058115.6A patent/CN103936550A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1528052A1 (en) * | 2003-10-29 | 2005-05-04 | FINCHIMICA S.p.A. | Process for the production of 4-amino-3,5-dichlorobenzotrifluoride with high purity commercial products being obtained in parallel |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106892792A (en) * | 2017-03-18 | 2017-06-27 | 山东道可化学有限公司 | A kind of method for continuously synthesizing and its synthesis device of 3,4 2 chlorobenzotrifluoride |
| CN106892792B (en) * | 2017-03-18 | 2023-05-23 | 山东道可化学有限公司 | Continuous synthesis method and equipment of 3, 4-dichloro benzotrifluoride |
| CN110317150A (en) * | 2019-07-30 | 2019-10-11 | 江苏超跃化学有限公司 | A method of preparing 3,4- dichlorobenzonitrile |
| CN115055144A (en) * | 2022-07-15 | 2022-09-16 | 常州新东化工发展有限公司 | System and process for producing o-chlorotrifluoromethylene |
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Application publication date: 20140723 |