CN1861554A - Production tech, of 3,4,5 trifluorophenol - Google Patents
Production tech, of 3,4,5 trifluorophenol Download PDFInfo
- Publication number
- 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
- Authority
- CN
- China
- Prior art keywords
- trifluoromethyl
- production technique
- phenol
- trifluoro
- benzene
- 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
Links
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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% |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200510049766XA CN100488930C (en) | 2005-05-09 | 2005-05-09 | Production technology of 3,4,5 trifluorophenol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200510049766XA CN100488930C (en) | 2005-05-09 | 2005-05-09 | Production technology of 3,4,5 trifluorophenol |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1861554A true CN1861554A (en) | 2006-11-15 |
CN100488930C CN100488930C (en) | 2009-05-20 |
Family
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB200510049766XA Active CN100488930C (en) | 2005-05-09 | 2005-05-09 | Production technology of 3,4,5 trifluorophenol |
Country Status (1)
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CN (1) | CN100488930C (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102086147A (en) * | 2009-12-04 | 2011-06-08 | 联化科技股份有限公司 | Preparation method of substituted 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 |
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 |
-
2005
- 2005-05-09 CN CNB200510049766XA patent/CN100488930C/en active Active
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101445431B (en) * | 2008-12-30 | 2012-02-29 | 衢州康鹏化学有限公司 | Method for preparing fluorophenol |
CN102086147B (en) * | 2009-12-04 | 2014-04-09 | 联化科技股份有限公司 | Preparation method of substituted phenol |
CN102086147A (en) * | 2009-12-04 | 2011-06-08 | 联化科技股份有限公司 | Preparation method of substituted phenol |
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 |
Also Published As
Publication number | Publication date |
---|---|
CN100488930C (en) | 2009-05-20 |
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Owner name: BINHAI YONGTAI PHARMACEUTICAL CHEMICAL CO., LTD. Free format text: FORMER OWNER: ZHEJIANG YONGTAI TECHNOLOGY CO., LTD. Effective date: 20110216 |
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Free format text: CORRECT: ADDRESS; FROM: 317016 COASTAL INDUSTRIAL PARK, DUQIAO TOWN, LINHAI CITY, ZHEJIANG PROVINCE TO: 224500 BINHAI COUNTY, YANCHENG CITY, JIANGSU PROVINCE |
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TR01 | Transfer of patent right |
Effective date of registration: 20110216 Address after: 224500 Binhai County, Jiangsu, Yancheng City Patentee after: Binhai Yongtai Medical Chemical Co.,Ltd. Address before: 317016 coastal industrial zone Du Du Zhen, Linhai City, Zhejiang Province Patentee before: Zhejiang Yongtai Technology Co., Ltd. |
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CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 224500 Binhai County, Yancheng City, Jiangsu Province Patentee after: Binhai Yongtai Technology Co.,Ltd. Address before: 224500 Binhai County, Yancheng City, Jiangsu Province Patentee before: Binhai Yongtai Medical Chemical Co.,Ltd. |
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TR01 | Transfer of patent right |
Effective date of registration: 20211021 Address after: 016000 Hainan Industrial Park, Wuhai Economic Development Zone, Hainan District, Wuhai City, Inner Mongolia Autonomous Region Patentee after: Inner Mongolia Yongtai Chemical Co.,Ltd. Address before: 224500 Binhai County, Yancheng City, Jiangsu Province Patentee before: Binhai Yongtai Technology Co.,Ltd. |
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TR01 | Transfer of patent right |