CN1861554A - Production tech, of 3,4,5 trifluorophenol - Google Patents
Production tech, of 3,4,5 trifluorophenol Download PDFInfo
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- CN1861554A CN1861554A CN 200510049766 CN200510049766A CN1861554A CN 1861554 A CN1861554 A CN 1861554A CN 200510049766 CN200510049766 CN 200510049766 CN 200510049766 A CN200510049766 A CN 200510049766A CN 1861554 A CN1861554 A CN 1861554A
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- trifluoromethyl
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- phenol
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- benzene
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005751 Copper oxide Substances 0.000 claims abstract description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims abstract description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 22
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims description 18
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 235000010288 sodium nitrite Nutrition 0.000 claims description 11
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 10
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 10
- 238000006193 diazotization reaction Methods 0.000 claims description 8
- 238000010792 warming Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- XNQLVVSDYOHIND-UHFFFAOYSA-N 3,4,5-tris(fluoromethyl)phenol Chemical compound FCC=1C=C(C=C(C1CF)CF)O XNQLVVSDYOHIND-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 6
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- WOPBXSIKBXNMFE-UHFFFAOYSA-N 3,4,5-tris(fluoromethyl)aniline Chemical compound FCC=1C=C(N)C=C(C1CF)CF WOPBXSIKBXNMFE-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- SZRDJHHKIJHJHQ-UHFFFAOYSA-N 3,4,5-trifluoroaniline Chemical compound NC1=CC(F)=C(F)C(F)=C1 SZRDJHHKIJHJHQ-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000010949 copper Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- HKJCELUUIFFSIN-UHFFFAOYSA-N 5-bromo-1,2,3-trifluorobenzene Chemical compound FC1=CC(Br)=CC(F)=C1F HKJCELUUIFFSIN-UHFFFAOYSA-N 0.000 description 6
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical class FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 6
- 238000009413 insulation Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 2
- 229960004643 cupric oxide Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- -1 boric acid ester Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Abstract
A process for preparing 3,4,5-trifluorophenol from 1-halo-3,4,5-trifluorobenzene includes such steps as high-pressure reacting on ammonia water at 100-200 deg.C under existence of cuprous salt, Cu salt or copper oxide as catalyst to obtain 3,4,5-trifluorophenylamine, diazotizing reaction, and hydrolyzing. It has high output (74-77%) of product.
Description
Technical field
The present invention relates to chemical field, relate in particular to and produce 3,4, the method for 5-trifluoromethyl phenol.
Background technology
3,4, the 5-trifluoromethyl phenol is a kind of important chemical intermediate, is mainly used in preparation liquid crystal, medicine intermediate.Its English name: 3,4,5-Trifluoro phenol, molecular formula is: C
6H
3F
3Be for OCAS number: the 99627-05-1 structural formula is:
At present, seen bibliographical information preparation 3,4,5-trifluoromethyl phenol technology is, adopt 3,4, the 5-trifluorobromobenzene makes Grignard reagent and generates 3 with the boric acid ester reaction again, 4,5-trifluorophenyl boric acid is then with hydroperoxidation preparation 3,4, the 5-trifluoromethyl phenol, this processing method need use a large amount of organic solvents during its synthetic production, and grignard reaction needs to react under anhydrous state, so there are a plurality of shortcomings in this technology, 1, a large amount of solvent aftertreatment difficulties of in suitability for industrialized production, using, 2, the Grignard reaction conditions harshness, 3, overall yield of reaction is low, its yield has only≤and 50%, the unit consumption height.
Summary of the invention
It is new 3,4 that technical problem to be solved by this invention provides that a kind of yield improves, the production technique of 5-trifluoromethyl phenol.For this reason, the present invention is by the following technical solutions: it is with 1-halo-3,4, and the 5-trifluoro-benzene is a starting raw material, and successively through following steps:
(1), make 1-halo-3,4,5-trifluoro-benzene and ammoniacal liquor carry out temperature of reaction to be 100～200 ℃ reaction under high pressure, to be catalyzer with cuprous salt, mantoquita or copper oxide, synthetic 3,4, the 5-trifluoromethyl aniline,
(2), with 3,4, the 5-trifluoromethyl aniline carries out diazotization reaction,
(3), " step (2) " product hydrolysis is generated 3,4, the 5-trifluoromethyl phenol.
In starting raw material, with 1-bromo-3,4, the 5-trifluoro-benzene is preferred.
In " step (1) ", the concentration of ammoniacal liquor is big more to add fast response more, generally serving as preferred greater than 20%, and with 28% for most preferably, 1-halo-3,4, the mol ratio of 5-trifluoro-benzene and ammoniacal liquor is preferably 1: 5～15mol, and better scope is 8～10mol.
The add-on of catalyzer is a 1-halo-3,4 in " step (1) ", 1%～5% of 5-trifluoro-benzene weight, and catalyzer is preferably cuprous salt or Red copper oxide.
In " step (1) ", reacting to 1-halo-3,4,5-trifluoro-benzene content reduces to＜and below 1%, reaction is finished.
In " step (1) ", when temperature surpassed 170 ℃, pressure increased the afterreaction excessive velocities and causes by product to increase, and from the angle of economy, serves as preferred with 150～160 ℃.
In " step (2) ", 3,4, the reactant of 5-trifluoromethyl aniline diazotization reaction is the vitriol oil, Sodium Nitrite, 3,4, the 5-trifluoromethyl aniline.3,4,5 trifluoromethyl anilines and sulfuric acid mol ratio be preferably 1: 4～and 8,3,4,5 trifluoromethyl anilines and Sodium Nitrite mol ratio be preferably 1: 0.9～and 1.2.In " step (2) ", add 98%H in the diazotization still
2SO
4, be warming up to 45～50 ℃, add 3,4, the 5-trifluoromethyl aniline rises to 60～70 ℃ of insulations, is incubated after 20～30 minutes, is cooled to-5 ℃, drips sodium nitrite in aqueous solution, drips and finishes, and drips water at≤10 ℃ in still, then≤10 ℃ of heat preservation for standby use.
In " step (3) ", in hydrolysis kettle, add the vitriol oil, copper sulfate, splash into " step (2) " product at 100～150 ℃, collect distillate simultaneously.3,4,5-trifluoromethyl aniline and sulfuric acid mol ratio be preferably 1: 1.3～and 1.6,3,4,5-trifluoromethyl aniline and copper sulfate mol ratio are preferably: 1: 0.4～1.2.When dripping " step (2) " product, can control its rate of addition according to practical situation, the temperature of reaction solution is remained in the setting range, to guarantee in reaction, constantly producing and collect distillate, so, can reduce the generation of by product and tar, significantly improve the yield of product.
For the product of " step (3) ", the oil reservoir of rectifying distillate is collected 103～105 ℃/80mmHg fraction, gets 3,4,5-trifluoromethyl phenol product.
Adopt production method provided by the present invention, raw material is easy to get, and aftertreatment is simple, need not special equipment, and product yield can reach 74%～77%, far above the getable yield of technology in the past.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Embodiment 1
With 1-bromo-3,4, the 5-trifluoro-benzene is a starting raw material, carries out following steps successively:
(1), add Red copper oxide 6kg in the 3000L autoclave, 1-bromo-3,4,5-trifluoro-benzene 600kg pumps into 28% ammoniacal liquor 2000L again.Airtight autoclave stirs down and is warming up to 150～160 ℃, and pressure 3.0MPa reacts sampling analysis behind the 8h, and 1-bromo-3,4,5-trifluoro-benzene content reduce to＜and 1%, reaction is finished.Be cooled to 50 ℃, material N
2Be pressed into crystallizing pan, stir and be cooled to 0 ℃, filter, obtain 3,4,5-trifluoromethyl aniline product, yield 95%, content＞99.5%.Reaction equation:
(2), add 98%H in the 1000L diazotization still
2SO
4300kg is warming up to 45～50 ℃, adds 3,4 under this temperature in still, 5-trifluoromethyl aniline 75kg; Finish, rise to 65 ℃ of insulation 25min, be cooled to-5 ℃, drip and to be dissolved in the solution that 120kg water is made into, temperature-5～0 ℃ by the 36kg Sodium Nitrite; Drip and finish, in still, dripping water 450kg below 10 ℃, stand-by at＜10 ℃ of insulation 20min then.Reaction equation:
(3), in hydrolysis kettle, add water 75kg, add 98%H again
2SO
475kg, copper sulfate 100kg is warming up to 130 ℃ then, and, splashes into " step (2) " product at 125～135 ℃, and about 12h of dropping time collects distillate simultaneously, tells lower floor's oil reservoir from distillate.103～105 ℃/80mmHg fraction is collected in oil reservoir rectifying, gets 3,4,5-trifluoromethyl phenol product, yield 77%, content＞99.5%.Reaction equation:
Embodiment 2
With 1-bromo-3,4, the 5-trifluoro-benzene is a starting raw material, carries out following steps successively:
(1), add cuprous sulfate 5g in the 3L autoclave, 1-bromo-3,4,5-trifluoro-benzene 600g pumps into 28% ammoniacal liquor 1800ml again.Airtight autoclave stirs down and is warming up to 150～160 ℃, and pressure 3.0MPa reacts sampling analysis behind the 8h, and 1-bromo-3,4,5-trifluoro-benzene content reduce to＜and 1%, reaction is finished.Be cooled to 50 ℃, material N
2Be pressed into crystallizing pan, stir and be cooled to 0 ℃, filter, obtain 3,4,5-trifluoromethyl aniline product, yield 94%, content＞99.5%.
(2), add 98%H in the 1000ml diazotization still
2SO
4300g is warming up to 45～50 ℃, adds 3,4 under this temperature in still, 5-trifluoromethyl aniline 75g; Finish, rise to 65 ℃ of insulation 30min, be cooled to-5 ℃, drip and to be dissolved in the solution that 115g water is made into, temperature-5～0 ℃ by the 35g Sodium Nitrite; Drip and finish, in still, dripping water 400g below 10 ℃, stand-by at＜10 ℃ of insulation 20min then.
(3), in hydrolysis kettle, add water 70g, add 98%H again
2SO
475g, copper sulfate 100g is warming up to 130 ℃ then, and, splashes into " step (2) " product at 125～135 ℃, and about 11h of dropping time collects distillate simultaneously, tells lower floor's oil reservoir from distillate.103～105 ℃/80mmHg fraction is collected in oil reservoir rectifying, gets 3,4,5-trifluoromethyl phenol product, yield 77.5%, content＞99.5%.
Embodiment 3～11
With 1-bromo-3,4, the 5-trifluoro-benzene is a starting raw material, and step and operation be with embodiment 2, each processing parameter and the results are shown in following cartogram.
| Step (1) | |||||
| Temperature (℃) | Catalyzer and add-on | Ammoniacal liquor add-on (mol) | Reaction times (hour) | Average yield | |
| Embodiment 3 | 105～135 | Cupric chloride 0.01～0.02 | 5 | 13 | 91.3％ |
| Embodiment 4 | 155～165 | Cuprous sulfate 0.02～0.04 | 10 | 8 | 95.8％ |
| Embodiment 5 | 165～180 | Cuprous chloride 0.04～0.05 | 15 | 6.5 | 90.9％ |
| Embodiment 6 | 140～155 | Red copper oxide 0.02～0.04 | 10 | 8.3 | 94.3％ |
| Embodiment 7 | 155～165 | Red copper oxide 0.04～0.05 | 8 | 7 | 95.5％ |
| Embodiment 8 | 165～180 | Cupric nitrate 0.01～0.02 | 5 | 9.5 | 92.0％ |
| Embodiment 9 | 140～155 | Copper sulfate 0.04～0.05 | 15 | 7.5 | 92.0％ |
| Embodiment 10 | 155～165 | Cupric oxide 0.01～0.02 | 5 | 10.2 | 92.8％ |
| Embodiment 11 | 170～195 | Red copper oxide 0.02～0.04 | 10 | 7 | 93.6％ |
| Step (2) | Step (3) | |||||
| 98% sulfuric acid add-on | The Sodium Nitrite add-on | 98% sulfuric acid add-on | The copper sulfate add-on | Temperature of reaction | Yield | |
| Embodiment 3 | 4.1 | 1.18 | 1.58 | 0.7 | 100～150℃ | 73.5％ |
| Embodiment 4 | 4.9 | 1.07 | 1.32 | 0.9 | 110～130℃ | 74.0％ |
| Embodiment 5 | 5.0 | 1.10 | 1.38 | 1.0 | 120～130℃ | 75.2％ |
| Embodiment 6 | 6 | 1.0 | 1.4 | 0.8 | 120～130℃ | 77.1％ |
| Embodiment 7 | 5.5 | 1.08 | 1.42 | 0.9 | 120～140℃ | 77.7％ |
| Embodiment 8 | 7 | 0.95 | 1.45 | 0.6 | 120～130℃ | 76.9％ |
| Embodiment 9 | 6.4 | 1.05 | 1.5 | 1.2 | 120～150℃ | 76.5％ |
| Embodiment 10 | 7 | 1.15 | 1.55 | 1.1 | 100～130℃ | 75.3％ |
| Embodiment 11 | 7.8 | 1.12 | 1.35 | 0.5 | 120～130℃ | 75.9％ |
In the last table, the catalyzer add-on is every 1kg1-bromo-3,4,5-trifluoro-benzene, the add-on of catalyzer (kg); The concentration of ammoniacal liquor is 28%, and its add-on is per 1 mole of 1-bromo-3,4,5-trifluoro-benzene, the mole number that ammoniacal liquor adds; 98% sulfuric acid add-on, Sodium Nitrite add-on, copper sulfate add-on are per 1 mole of 1-bromo-3,4,5-trifluoro-benzene, the added separately mole number of mentioned reagent.
As can be seen from the above table, when temperature surpassed 170 ℃, pressure increased the afterreaction excessive velocities and causes by product to increase, and from the angle of economy, was the preferred of step (1) with 150～160 ℃.In step (2), trifluoromethyl aniline and vitriolic mol ratio are about 6, specifically be 5.5～7, the mol ratio of trifluoromethyl aniline and Sodium Nitrite is 0.95～1.05, trifluoromethyl aniline and vitriolic mol ratio are 1.4～1.45 in the step (3), the mol ratio of trifluoromethyl aniline and copper sulfate is 0.6～0.9, and hydrolysising reacting temperature is in the time of 120～130 ℃, and reaction process is more economical, yield is higher.
Embodiment 12-13
Embodiment 12 adopts 1-chloro-3,4, and the 5-trifluoro-benzene substitutes the 1-bromo-3,4 of the foregoing description, the 5-trifluoro-benzene, and embodiment 13 adopts 1-iodo-3,4, and the 5-trifluoro-benzene substitutes the 1-bromo-3,4 of the foregoing description, 5-trifluoro-benzene.
Embodiment 12 adopts the processing condition of embodiment 2, and 3,4,5-trifluoromethyl phenol yield is 57%, embodiment 13 also adopts step and the parameter of embodiment 2, and 3,4,5-trifluoromethyl phenol yield is 55%.
Claims (10)
1, a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that it with 1-halo-3,4, and the 5-trifluoro-benzene is a starting raw material, and successively through following steps:
(1), make 1-halo-3,4,5-trifluoro-benzene and ammoniacal liquor carry out temperature of reaction to be 100～200 ℃ reaction under high pressure, to be catalyzer with cuprous salt, mantoquita or copper oxide, synthetic 3,4, the 5-trifluoromethyl aniline,
(2), with 3,4, the 5-trifluoromethyl aniline carries out diazotization reaction,
(3), " step (2) " product hydrolysis is generated 3,4, the 5-trifluoromethyl phenol.
2, as claimed in claim 1 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that in " step (1) ", and the concentration of ammoniacal liquor to be serving as preferred greater than 20%, 1-halo-3,4, and the mol ratio of 5-trifluoro-benzene and ammoniacal liquor is preferably 1: 5～15mol.
3, as claimed in claim 1 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that the add-on of catalyzer in " step (1) " is a 1-halo-3,4,1%～5% of 5-trifluoro-benzene weight, and catalyzer is preferably cuprous salt or Red copper oxide.
4, as claimed in claim 1 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that reacting to 1-halo-3,4 in " step (1) ", and 5-trifluoro-benzene content reduces to＜and below 1%, reaction is finished.
5, as claimed in claim 1 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that in " step (1) ", temperature of reaction serves as preferred with 150～160 ℃.
6, as claimed in claim 1 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that in " step (2) ", 3,4, and the reactant of 5-trifluoromethyl aniline diazotization reaction is the vitriol oil, Sodium Nitrite, 3,4, the 5-trifluoromethyl aniline.3,4,5-trifluoromethyl aniline and sulfuric acid mol ratio are preferably: 1: 4～8,3,4, and 5-trifluoromethyl aniline and Sodium Nitrite mol ratio be preferably 1: 0.9～and 1.2.
7, as claimed in claim 6 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that adding 98%H in the diazotization still in " step (2) "
2SO
4, be warming up to 45～50 ℃, add 3,4, the 5-trifluoromethyl aniline rises to 60～70 ℃, is incubated after 20～30 minutes, is cooled to-5 ℃, drips sodium nitrite in aqueous solution, drips and finishes, and drips water in the time of≤10 ℃, then≤10 ℃ of heat preservation for standby use in still.
8, as claimed in claim 1 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that adding the vitriol oil, copper sulfate in " step (3) " in hydrolysis kettle, splashes into " step (2) " product at 100～150 ℃, collects distillate simultaneously.
9, as claimed in claim 8 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that in " step (3) ", 3,4,5-trifluoromethyl aniline and sulfuric acid mol ratio be preferably 1: 1.3～and 1.6,3,4,5-trifluoromethyl aniline and copper sulfate mol ratio are preferably: 1: 0.4～1.2.
10, as claimed in claim 8 a kind of 3,4, the production technique of 5-trifluoromethyl phenol is characterized in that the oil reservoir of rectifying distillate, collects 103～105 ℃/80mmHg fraction, 3,4,5-trifluoromethyl phenol product.
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| CN102108044A (en) * | 2011-01-28 | 2011-06-29 | 常州吉恩化工有限公司 | Purification method of liquid crystal intermediate 3,4,5-trifluoro phenol |
| CN102260143A (en) * | 2011-05-18 | 2011-11-30 | 郓城县世炬化工有限公司 | Production process for 3-fluorophenol |
| CN101445431B (en) * | 2008-12-30 | 2012-02-29 | 衢州康鹏化学有限公司 | Method for preparing fluorophenol |
| CN102503779A (en) * | 2011-11-18 | 2012-06-20 | 江苏联化科技有限公司 | Preparation method of 3, 4, 5-trifluoromethylphenol |
| CN102887817A (en) * | 2012-09-11 | 2013-01-23 | 浙江永太科技股份有限公司 | Novel method for synthesizing 2,3,4,5,6-pentafluorophenol |
| CN103497111A (en) * | 2013-09-09 | 2014-01-08 | 江苏德峰药业有限公司 | Synthetic method for 2, 3, 4-trifluoroaniline |
| CN106946659A (en) * | 2017-03-03 | 2017-07-14 | 上海康鹏科技有限公司 | A kind of preparation method of Pentafluorophenol |
| CN109456150A (en) * | 2018-10-25 | 2019-03-12 | 浙江林江化工股份有限公司 | A kind of synthetic method of 3,4,5-Trifluoro phenol |
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2005
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| CN102108044B (en) * | 2011-01-28 | 2013-09-25 | 常州吉恩化工有限公司 | Purification method of liquid crystal intermediate 3,4,5-trifluoro phenol |
| CN102108044A (en) * | 2011-01-28 | 2011-06-29 | 常州吉恩化工有限公司 | Purification method of liquid crystal intermediate 3,4,5-trifluoro phenol |
| CN102260143A (en) * | 2011-05-18 | 2011-11-30 | 郓城县世炬化工有限公司 | Production process for 3-fluorophenol |
| CN102503779A (en) * | 2011-11-18 | 2012-06-20 | 江苏联化科技有限公司 | Preparation method of 3, 4, 5-trifluoromethylphenol |
| CN102887817A (en) * | 2012-09-11 | 2013-01-23 | 浙江永太科技股份有限公司 | Novel method for synthesizing 2,3,4,5,6-pentafluorophenol |
| CN102887817B (en) * | 2012-09-11 | 2015-04-01 | 浙江永太科技股份有限公司 | Novel method for synthesizing 2,3,4,5,6-pentafluorophenol |
| CN103497111A (en) * | 2013-09-09 | 2014-01-08 | 江苏德峰药业有限公司 | Synthetic method for 2, 3, 4-trifluoroaniline |
| CN103497111B (en) * | 2013-09-09 | 2015-10-21 | 江苏德峰药业有限公司 | A kind of synthetic method of 2,3,4-trifluoromethyl aniline |
| CN106946659A (en) * | 2017-03-03 | 2017-07-14 | 上海康鹏科技有限公司 | A kind of preparation method of Pentafluorophenol |
| CN106946659B (en) * | 2017-03-03 | 2020-08-25 | 上海康鹏科技股份有限公司 | Preparation method of pentafluorophenol |
| CN109456150A (en) * | 2018-10-25 | 2019-03-12 | 浙江林江化工股份有限公司 | A kind of synthetic method of 3,4,5-Trifluoro phenol |
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