CN1390820A - Process for preparing trifluomethoxybenzene - Google Patents
Process for preparing trifluomethoxybenzene Download PDFInfo
- Publication number
- CN1390820A CN1390820A CN 01114041 CN01114041A CN1390820A CN 1390820 A CN1390820 A CN 1390820A CN 01114041 CN01114041 CN 01114041 CN 01114041 A CN01114041 A CN 01114041A CN 1390820 A CN1390820 A CN 1390820A
- Authority
- CN
- China
- Prior art keywords
- anisole
- reaction
- phenyl ether
- trifluoromethyl phenyl
- reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims abstract description 21
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000007670 refining Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 238000005660 chlorination reaction Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- 238000003682 fluorination reaction Methods 0.000 claims description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- CLYZNABPUKUSDX-UHFFFAOYSA-N trichloromethoxybenzene Chemical compound ClC(Cl)(Cl)OC1=CC=CC=C1 CLYZNABPUKUSDX-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing trifluoromethoxy benzene includes such steps as chlorinating methoxybenzene to obtain trichloromethoxy benzene, adding HF and catalyst, reacting at 80-100 deg.C and 1-2 MPa for 2-6 hr, and refining. Its advantages are simple process, high stability and high productivity.
Description
The present invention relates to a kind of production method of fluorine containing aromatic compound, especially relate to a kind of method of producing Trifluoromethyl phenyl ether.
Fluorine containing aromatic compound and fluorine containing aromatic compound ratio not have premium propertiess such as consumption is few, toxicity is low, drug effect is high, metabolic capacity is strong in fields such as medicine, agricultural chemicals, and be of many uses.Trifluoromethyl phenyl ether belongs to a kind of in the fluorine containing aromatic compound, at present the operational path of synthetic Trifluoromethyl phenyl ether have multiple, but the suitability for industrialized production that all is unrealized.
The objective of the invention is to, a kind of method of producing Trifluoromethyl phenyl ether is provided, realize suitability for industrialized production.
Produce Trifluoromethyl phenyl ether among the present invention, adopt fluorizated two-step approach after the first chlorination: 1. chlorination, with anisole
Organic solvent, proper catalyst add in the reactor, are heated to 50 ℃ under the normal pressure, feed chlorine Cl then
2, reaction is 6-15 hour under 50-100 ℃ of condition, makes intermediate product trichlorine anisole
2. fluoridize, in trichlorine anisole suction fluorination reactor, add hydrogen fluoride HF, proper catalyst, reaction is 2-6 hour under temperature 80-100 ℃, pressure 1.0-2.0MPa condition, makes Trifluoromethyl phenyl ether after refining
Finished product.Chemical equation is: 1. chlorination:
2. fluoridize:
Each reactant is by the required mol ratio of reaction.For making reaction more abundant, the chlorine that feeds in the chlorination reaction is excessive, with the mol ratio of anisole be that the organic solvent of 3.2-4 anisole is selected tetracol phenixin CCl for use
4, with the mol ratio of anisole be 4-6.
Technology of the present invention is simple, and is owing to adopt two-step approach to produce, reliable and stable, production efficiency is high.
The present invention will be further described below in conjunction with drawings and Examples:
Fig. 1 is a process flow sheet of the present invention;
Embodiment 1:
1 mole of anisole, 4 moles in tetracol phenixin, proper catalyst are added in the reactor, be heated to 50 ℃ under the normal pressure, feed 3.2 moles in chlorine then, reaction is 6 hours under 50-100 ℃ of condition, makes intermediate product trichlorine anisole.Tail gas after falling-film absorber absorbs can byproduct hydrochloric acid, the reaction recovery tetracol phenixin that finishes; Fluoridize, in 1 mole of suction fluorination reactor of trichlorine anisole, add 3 moles in hydrogen fluoride, proper catalyst, reaction is 2 hours under temperature 80-100 ℃, pressure 1.0MPa condition, after reaction finishes, make the Trifluoromethyl phenyl ether work in-process, add soda ash again, make the Trifluoromethyl phenyl ether finished product through steam distillation, rectifying.
Embodiment 2:
1 mole of anisole, 6 moles in tetracol phenixin, proper catalyst are added in the reactor, be heated to 50 ℃ under the normal pressure, feed 4 moles in chlorine then, reaction is 15 hours under 50-100 ℃ of condition, makes intermediate product trichlorine anisole.Tail gas after falling-film absorber absorbs can byproduct hydrochloric acid, the reaction recovery tetracol phenixin that finishes; Fluoridize, in 1 mole of suction fluorination reactor of trichlorine anisole, add 3 moles in hydrogen fluoride, proper catalyst, reaction is 6 hours under temperature 80-100 ℃, pressure 2.0MPa condition, after reaction finishes, make the Trifluoromethyl phenyl ether work in-process, add soda ash again, make the Trifluoromethyl phenyl ether finished product through steam distillation, rectifying.
Embodiment 3:
1 mole of anisole, 6 moles in tetracol phenixin, proper catalyst are added in the reactor, be heated to 50 ℃ under the normal pressure, feed 3.5 moles in chlorine then, reaction is 10 hours under 50-100 ℃ of condition, makes intermediate product trichlorine anisole.Tail gas after falling-film absorber absorbs can byproduct hydrochloric acid, the reaction recovery tetracol phenixin that finishes; Fluoridize, in 1 mole of suction fluorination reactor of trichlorine anisole, add 3 moles in hydrogen fluoride, proper catalyst, reaction is 4 hours under temperature 80-100 ℃, pressure 1.5MPa condition, after reaction finishes, make the Trifluoromethyl phenyl ether work in-process, add soda ash again, make the Trifluoromethyl phenyl ether finished product through steam distillation, rectifying.
Among the present invention, the organic solvent of anisole can be selected other solvent for use, preferentially selects tetracol phenixin for use.The time that provides in the foregoing description finishes to just in time with reaction, is not absolute reference.
Claims (2)
1. method of producing Trifluoromethyl phenyl ether, it is characterized in that: the fluorizated two-step approach makes after adopting first chlorination; 1. chlorination is with anisole
Organic solvent, proper catalyst add in the reactor, are heated to 50 ℃ under the normal pressure, feed chlorine Cl
2, temperature 50-100 ℃ of reaction 6-15 hour, make intermediate product trichlorine anisole then
2. fluoridize, in trichlorine anisole suction fluorination reactor, add hydrogen fluoride, proper catalyst, reaction 2-6 hour down of temperature 80-100 ℃, pressure 1.0-2.0MPa makes Trifluoromethyl phenyl ether after refining
Finished product.
2. the method for production Trifluoromethyl phenyl ether according to claim 1 is characterized in that: the chlorine that adds in the described chlorination reaction in the reactor is excessive, with the mol ratio of anisole be 3.2-4: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011140410A CN1156424C (en) | 2001-06-07 | 2001-06-07 | Process for preparing trifluomethoxybenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011140410A CN1156424C (en) | 2001-06-07 | 2001-06-07 | Process for preparing trifluomethoxybenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1390820A true CN1390820A (en) | 2003-01-15 |
| CN1156424C CN1156424C (en) | 2004-07-07 |
Family
ID=4660734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011140410A Ceased CN1156424C (en) | 2001-06-07 | 2001-06-07 | Process for preparing trifluomethoxybenzene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1156424C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102120717A (en) * | 2010-12-16 | 2011-07-13 | 金凯(辽宁)化工有限公司 | Method for producing trichloromethoxybenzene by using chlorobenzene as solvent |
| CN101450891B (en) * | 2008-12-30 | 2012-05-23 | 滨海康杰化学有限公司 | Method for preparing 2-fluoro-4-bromo trifluoromethoxyphenyl |
| CN102531421A (en) * | 2010-12-13 | 2012-07-04 | 北京金源化学集团有限公司 | Cement with low carbon dioxide emission and preparation method thereof |
| CN102557895A (en) * | 2010-12-28 | 2012-07-11 | 北京金源化学集团有限公司 | Method for preparing trichlorine metoxybenzene |
| WO2016125185A2 (en) | 2015-02-02 | 2016-08-11 | Srf Limited | Process for the preparation of 4-substituted-1-(trifluoromethoxy)benzene compounds |
| CN106008175A (en) * | 2016-05-19 | 2016-10-12 | 山东道可化学有限公司 | Production method of trifluoromethoxybenzene |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103553884B (en) * | 2013-11-15 | 2015-03-25 | 金凯(辽宁)化工有限公司 | Method for preparing trifluoromethoxybenzene |
-
2001
- 2001-06-07 CN CNB011140410A patent/CN1156424C/en not_active Ceased
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101450891B (en) * | 2008-12-30 | 2012-05-23 | 滨海康杰化学有限公司 | Method for preparing 2-fluoro-4-bromo trifluoromethoxyphenyl |
| CN102531421A (en) * | 2010-12-13 | 2012-07-04 | 北京金源化学集团有限公司 | Cement with low carbon dioxide emission and preparation method thereof |
| CN102120717A (en) * | 2010-12-16 | 2011-07-13 | 金凯(辽宁)化工有限公司 | Method for producing trichloromethoxybenzene by using chlorobenzene as solvent |
| CN102120717B (en) * | 2010-12-16 | 2013-07-10 | 金凯(辽宁)化工有限公司 | Method for producing trichloromethoxybenzene by using chlorobenzene as solvent |
| CN102557895A (en) * | 2010-12-28 | 2012-07-11 | 北京金源化学集团有限公司 | Method for preparing trichlorine metoxybenzene |
| WO2016125185A2 (en) | 2015-02-02 | 2016-08-11 | Srf Limited | Process for the preparation of 4-substituted-1-(trifluoromethoxy)benzene compounds |
| CN106008175A (en) * | 2016-05-19 | 2016-10-12 | 山东道可化学有限公司 | Production method of trifluoromethoxybenzene |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1156424C (en) | 2004-07-07 |
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Effective date of registration: 20130514 Address after: 123000 Fluorine Industry Development Zone, Fuxin City, Liaoning Province Patentee after: Liu Guangsheng Address before: 123000 Fuxin city of Liaoning province Fumeng Yima map town train station east 100 meters Patentee before: Kingchem (Liaoning) LLC |
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