CN1907945B - Process for preparing trifluoroethyl methacrylate - Google Patents
Process for preparing trifluoroethyl methacrylate Download PDFInfo
- Publication number
- CN1907945B CN1907945B CN2006100302026A CN200610030202A CN1907945B CN 1907945 B CN1907945 B CN 1907945B CN 2006100302026 A CN2006100302026 A CN 2006100302026A CN 200610030202 A CN200610030202 A CN 200610030202A CN 1907945 B CN1907945 B CN 1907945B
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- China
- Prior art keywords
- trifluoroethyl methacrylate
- trifluoroethanol
- stopper
- reaction
- methacrylic chloride
- Prior art date
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Abstract
The invention discloses a preparation method for trifluoroethyl methacrylate. The method comprises taking trifluoroethanol and methacryloyl chloride as raw materials, carrying out esterification reaction under the inhibitor protection, and collecting the final product trifluoroethyl methacrylate with the purity above 99%, yield above 80% and boiling point of 100.8-101.2DEG C. Compared with the existing technology, the invention has the advantages of mild reaction conditions, stable product quality, low cost, and being suitable for industrial production.
Description
Technical field
The present invention relates to a kind of preparation method for trifluoroethyl methacrylate.
Background technology
Trifluoroethyl methacrylate is a kind of intermediate of important organic synthesis, especially can be used as the intermediate of preparation fluoro-containing coating, in fluorine-containing exterior coating field and weaving is whole dyes, is widely used in the paper manufacturing.Its structure is:
CH
2＝CCH
3COOCH
2CF
3
Trifluoroethyl methacrylate is a kind of of fluorinated acrylate, in the prior art, because fluorinated acrylate can be introduced fluoro-containing group in polymkeric substance, greatly reduced the surface tension of polymeric material, improve thermostability, therefore performances such as light stability day by day increase the research of fluorinated acrylate and the report of application.Polym.Int.50; 863-868 (2001) reported method: it is with fluorine-containing alcohol, methacrylic chloride, stopper, organic bases are raw material, ether is made solvent, low-temp reaction obtains fluorinated acrylate, and this method is used lower boiling ether solvent, operates dangerous, reaction is produced and is held than low, wastewater flow rate is big, the cost height, and industrial prospect is undesirable.
Summary of the invention
The object of the invention provides a kind of preparation method for trifluoroethyl methacrylate, uses ether solvent dangerous big in the prior art to overcome, and reaction is produced and held than low the deficiency that cost is high.
Technical conceive of the present invention is such: with trifluoroethanol, methacrylic chloride is a raw material, carries out esterification under the stopper protection, collects the target product trifluoroethyl methacrylate then from reaction product.
Method of the present invention comprises the steps:
Trifluoroethanol, methacrylic chloride and stopper reacted 7-15 hour under 30-80 ℃ condition, collected the target product trifluoroethyl methacrylate from reaction product.
Stopper used in the present invention is a phenolic compound, is selected from Resorcinol, p methoxy phenol or 2, and the 6-toluene di-tert-butyl phenol, preferred 2, the 6-toluene di-tert-butyl phenol.
According to the present invention, the mass ratio of trifluoroethanol and stopper is 1000-700:1, and the mol ratio of trifluoroethanol and methacrylic chloride is 1:0.9-1:1.5.
Collect trifluoroethyl methacrylate and comprise the steps: cooling from reaction product, with sodium carbonate solution washing reaction liquid, washing, drying steams target product of the present invention.The purity of the trifluoroethyl methacrylate that is obtained is greater than more than 99%, and productive rate is greater than 80%, and boiling point is 100.8-101.2 ℃, consistent (document Polym.Int., 50 with bibliographical information; 863-868,2001 values: 101 ℃).Infared spectrum confirms the structure of product.
Beneficial effect
Synthetic method of the present invention is directly carried out esterification with trifluoroethanol and methacrylic chloride, avoids using ether solvent and as the organic bases of acid absorber.The present invention compared with prior art, the reaction process mild condition, constant product quality, cost reduces, and is suitable for suitability for industrialized production.
Specific implementation method
Below by embodiment the present invention is done further, but embodiment does not limit protection scope of the present invention.
Embodiment 1
Heating is being housed, stir, thermometer, add 10.0g (0.1mol) trifluoroethanol in the reactor of reflux condensing tube respectively, 0.01g2,6-toluene di-tert-butyl phenol and 13.6g (0.13mol) methacrylic chloride, stir, temperature of reaction is controlled at 60-65 ℃, reacted 8 hours, the reaction solution that obtains is cooled to room temperature,, stirs 1 hour to neutral with 5% sodium carbonate solution (concentration expressed in percentage by weight) washing, side reaction thing in the decomposition reaction liquid and excessive methacrylic chloride raw material, anhydrous magnesium sulfate drying is used in washing, filters, the filtrate decompression distillation that obtains, obtain the 13.6g trifluoroethyl methacrylate, productive rate 81%, purity 99.2% (HPLC), boiling point 100.8-101.2 ℃ (literature value is 101 ℃)
IR(liquid?film)：1740cm
-1，1638cm
-1，1350-1270cmu
-1，1180-1135cm
-1，980-945cm
-1。
Embodiment 2
Heating is being housed, stir, thermometer, add 10.0g (0.1mol) trifluoroethanol in the reactor of reflux condensing tube respectively, 0.01g2,6-toluene di-tert-butyl phenol and 14.6g (0.14mol) methacrylic chloride, heated and stirred gradually, temperature of reaction is controlled at 50-70 ℃, reacted 7 hours, the reaction solution that obtains is cooled to room temperature, to neutral, stirred side reaction thing in the decomposition reaction liquid and excessive methacrylic chloride raw material with 5% sodium carbonate solution (concentration expressed in percentage by weight) washing 1 hour, washing, use anhydrous magnesium sulfate drying, filter, the filtrate decompression distillation that obtains, obtain the 13.7g trifluoroethyl methacrylate, productive rate 81.5%, purity 99.3% (HPLC), boiling point 100.9-101.2 ℃.
Embodiment 3
Heating is being housed, stir, thermometer, add 10.0g (0.1mol) trifluoroethanol in the reactor of reflux condensing tube respectively, 0.01g2, the 6-toluene di-tert-butyl phenol, 14.6g (0.14mol) methacrylic chloride, heated and stirred gradually, temperature of reaction is controlled at 40-60 ℃, reacts 3 hours, temperature of reaction is controlled at 60-80 ℃, reacted 5 hours, the reaction solution that obtains is cooled to room temperature, and is extremely neutral with 5% sodium carbonate solution (concentration expressed in percentage by weight) washing, stirred 1 hour, side reaction thing in the decomposition reaction liquid and excessive methacrylic chloride raw material, anhydrous magnesium sulfate drying is used in washing, filter, the filtrate decompression distillation that obtains obtains the 14.0g trifluoroethyl methacrylate, productive rate 83.4%, purity 99.4% (HPLC), boiling point 100.9-101.2 ℃.
Claims (5)
1. a preparation method for trifluoroethyl methacrylate comprises the steps:
Trifluoroethanol, methacrylic chloride and stopper reacted 7-15 hour under 30-80 ℃ condition, collected the target product trifluoroethyl methacrylate then from reaction product;
Described stopper is a Resorcinol, p methoxy phenol or 2,6-tertiary butyl p-cresol.
2. method according to claim 1 is characterized in that, described stopper is preferred 2, the 6-toluene di-tert-butyl phenol.
3. method according to claim 1 and 2 is characterized in that, the mass ratio of described trifluoroethanol and stopper is 1000-700: 1.
4. method according to claim 1 is characterized in that, the mol ratio of described trifluoroethanol and methacrylic chloride is 1: 0.9-1: 1.5.
5. method according to claim 1 is characterized in that, collects trifluoroethyl methacrylate and comprise the steps: cooling from reaction product, and with sodium carbonate solution washing reaction liquid, washing, drying steams target product of the present invention.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006100302026A CN1907945B (en) | 2006-08-18 | 2006-08-18 | Process for preparing trifluoroethyl methacrylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2006100302026A CN1907945B (en) | 2006-08-18 | 2006-08-18 | Process for preparing trifluoroethyl methacrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1907945A CN1907945A (en) | 2007-02-07 |
| CN1907945B true CN1907945B (en) | 2011-04-27 |
Family
ID=37699198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006100302026A Expired - Fee Related CN1907945B (en) | 2006-08-18 | 2006-08-18 | Process for preparing trifluoroethyl methacrylate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1907945B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101168507B (en) * | 2007-11-22 | 2011-11-16 | 上海化学试剂研究所 | Method for preparing 2,2,2-trifluoroethyl methacrylate |
| EP3109230B1 (en) | 2014-02-17 | 2019-11-20 | Li, Qingeng | Class of carboxylic acid derivatives and use thereof in preparation of prodrugs |
| CN104045561A (en) * | 2014-05-21 | 2014-09-17 | 江苏德峰药业有限公司 | Synthetic method for 3,3,5-trimethylcyclohexanol salicylate |
| CN108774134A (en) * | 2018-05-29 | 2018-11-09 | 江苏蓝色星球环保科技股份有限公司 | The production method of trifluoroethyl methacrylate |
| CN111454123B (en) * | 2020-05-18 | 2022-08-05 | 新元化学(山东)股份有限公司 | Flexible reaction device and method for trifluoroethanol/trifluoroethyl methacrylate |
| CN112920046A (en) * | 2021-01-26 | 2021-06-08 | 宁波南大光电材料有限公司 | Hexafluoroisopropyl methacrylate and preparation method thereof |
| CN114292191A (en) * | 2021-12-17 | 2022-04-08 | 重庆新氟科技有限公司 | Preparation method of fluorine-containing methacrylic acid monomer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4859793A (en) * | 1985-06-18 | 1989-08-22 | Societe Chimique Des Charbonnages S.A. | Process for the production of fluoroalkyl acrylates |
-
2006
- 2006-08-18 CN CN2006100302026A patent/CN1907945B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4859793A (en) * | 1985-06-18 | 1989-08-22 | Societe Chimique Des Charbonnages S.A. | Process for the production of fluoroalkyl acrylates |
Non-Patent Citations (2)
| Title |
|---|
| 陈先进等.甲基丙烯酸三氟乙酯的制备.浙江化工35 6.2004,35(6),19. |
| 陈先进等.甲基丙烯酸三氟乙酯的制备.浙江化工35 6.2004,35(6),19. * |
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|---|---|
| CN1907945A (en) | 2007-02-07 |
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Granted publication date: 20110427 Termination date: 20130818 |