CN105384675B - The preparation method of the Phenylindole of plastic heat stabilizer 2 - Google Patents
The preparation method of the Phenylindole of plastic heat stabilizer 2 Download PDFInfo
- Publication number
- CN105384675B CN105384675B CN201510960662.8A CN201510960662A CN105384675B CN 105384675 B CN105384675 B CN 105384675B CN 201510960662 A CN201510960662 A CN 201510960662A CN 105384675 B CN105384675 B CN 105384675B
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- CN
- China
- Prior art keywords
- preparation
- heat stabilizer
- phenylindone
- plastic heat
- piperidines
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
The invention belongs to the preparation method of chemosynthesis technical field, more particularly to 2 Phenylindoles.This method is that ortho-aminotoluene and methyl benzoate are added into pyridine and piperidines in the mixed solvent, and heating systems terminate to 95~105 DEG C and insulation reaction liquid to reaction after stirring, and mixture is evaporated off after solvent into residue through being recrystallized to give 2 Phenylindoles.Mild condition of the present invention, it is not necessary to which traditional highly basic is used as catalyst.Raw material is cheap and easy to get；A new selection is provided for 2 Phenylindoles of synthesis.
Description
Technical field
The invention belongs to the preparation method of chemosynthesis technical field, more particularly to 2-phenylindone.
Background technology
2-phenylindone is as the heat stabilizer of igelite, and he is because toxicity is atomic and the premium properties such as non-carcinogenesis
It is permitted for manufacturing packed video membrane material in states such as America and Europes.At present, the method for commercial synthesis 2-phenylindone is a lot, substantially
It is divided into and uses phenylhydrazine with acetophenone for the Fisher methods of raw material, the Madllung methods that benzoyl-ortho-aminotoluene is raw material, adjacent aniline
The Bischer methods that benzoylformaldoxime is the Reissert methods and bromination acetophenone of raw material and aniline is raw material.These methods all possess
Improved space, such as Madllung methods are accomplished by using Sodamide as base catalyst, and the material alkalescence is extremely strong, expensive.
The present invention makees solvent using the cheap pyridine easily reclaimed and piperidines mixed liquor, and the mixed solvent substitutes Sodamide synthesis 2- phenyl Yin
Diindyl is there is not yet document report.
The content of the invention
A kind of method for synthesizing 2-phenylindone of offer of the present invention.
The technical scheme is that：
By ortho-aminotoluene and methyl benzoate be added to pyridine and piperidines in the mixed solvent, wherein piperidines and pyridine
Volume ratio is not less than 1/100；Heating systems terminate to 95~105 DEG C and insulation reaction liquid to reaction after stirring, and will mix
Residue is evaporated off after solvent through being recrystallized to give 2-phenylindone in thing.
The present invention reaction equation be：
The present invention is using ortho-aminotoluene and methyl benzoate as raw material, the reaction generation 2- in mixed solvent pyridine and piperidines
Phenylindole.This method is simple to operate, and raw material and solvent are cheap and easy to get.Ortho-aminotoluene and methyl benzoate feeds intake during production
Mol ratio is 1 ︰ 1.Pyridine and piperidines volume ratio are preferably 100 ︰ 1, and when piperidines amount is less than this consumption, the reaction time will extend simultaneously
And reaction is incomplete, when piperidines amount is more than this consumption, because piperidines is more expensive than pyridine, so causing unnecessary waste.In the throwing
Optimal catalytic effect can be reached under doses.
The insulation reaction time is 2~3 hours.When time is not enough, react not thorough, experiment showed within the time,
Products collection efficiency highest.
The reaction temperature is 95~105 DEG C, and during less than this temperature, the reaction speed is slower.Experiment shows that the temperature is
Optimal reaction temperature.
In the present invention, recrystallization solvent can be chloroform, ethanol, methanol, ethyl acetate etc., but ethyl acetate.
Advantages of the present invention and effect are：
1. mild condition of the present invention, it is not necessary to which traditional highly basic is used as catalyst.
2. the present invention provides a new selection for synthesis 2-phenylindone.
3. raw material of the present invention is cheap and easy to get.
Embodiment
First, reactions steps：
The adjacent ammonia of mixed solution, the 7.5kg of the 40L piperidines containing 0.4L piperidines and pyridine is sequentially added into 50L reactors
Base toluene and 6.8kg methyl benzoates, heating response system is reacted to 100 DEG C, after 2h to be completed, and is divided exactly after solvent, mixture is used
100L re-crystallizing in ethyl acetate, obtains 3,4,5- triphenyl -1,2- pyrazoles.
The present invention reaction equation be：
2nd, product is identified：
1st, 2-phenylindone, white solid, mp:186.8-187.2℃.It is consistent with document.
2nd, melting point is not reduced after product is mixed with the sterling of market sale, tests fusing point or 186.8-187.2 DEG C.
Claims (5)
1. a kind of preparation method of plastic heat stabilizer 2-phenylindone, it is characterised in that：By ortho-aminotoluene and benzoic acid first
Ester is added to pyridine and piperidines in the mixed solvent, and the wherein volume ratio of piperidines and pyridine is not less than 1/100；Heated after stirring
System terminates to 95~105 DEG C and insulation reaction liquid to reaction, and mixture is evaporated off after solvent into residue through being recrystallized to give 2-
Phenylindole.
2. the preparation method of plastic heat stabilizer 2-phenylindone according to claim 1, it is characterised in that the adjacent ammonia
The molar ratio of base toluene and methyl benzoate is 1 ︰ 1.
3. the preparation method of plastic heat stabilizer 2-phenylindone according to claim 1, it is characterised in that the piperidines
Volume ratio with pyridine is 1：100.
4. the preparation method of plastic heat stabilizer 2-phenylindone according to claim 1, it is characterised in that insulation reaction
Time is 2~3 hours.
5. the preparation method of plastic heat stabilizer 2-phenylindone according to claim 1, it is characterised in that make in recrystallization
Recrystallization solvent is used as with ethyl acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510960662.8A CN105384675B (en) | 2015-12-21 | 2015-12-21 | The preparation method of the Phenylindole of plastic heat stabilizer 2 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510960662.8A CN105384675B (en) | 2015-12-21 | 2015-12-21 | The preparation method of the Phenylindole of plastic heat stabilizer 2 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105384675A CN105384675A (en) | 2016-03-09 |
| CN105384675B true CN105384675B (en) | 2017-08-25 |
Family
ID=55417503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510960662.8A Expired - Fee Related CN105384675B (en) | 2015-12-21 | 2015-12-21 | The preparation method of the Phenylindole of plastic heat stabilizer 2 |
Country Status (1)
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| CN (1) | CN105384675B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105885087B (en) * | 2016-04-19 | 2018-04-13 | 东莞市宏福新材料有限公司 | Pvc heat stabilizer and preparation method thereof |
| CN105802074B (en) * | 2016-04-19 | 2017-08-25 | 佛山市稳格家居用品有限公司 | heat-resistant PVC |
| CN105713320B (en) * | 2016-04-19 | 2017-09-22 | 赖树兴 | heat stabilizer for PVC and preparation method thereof |
| CN105713319B (en) * | 2016-04-19 | 2017-07-21 | 汕头市升平塑胶制刷厂有限公司 | A kind of heat-resistant PVC |
-
2015
- 2015-12-21 CN CN201510960662.8A patent/CN105384675B/en not_active Expired - Fee Related
Non-Patent Citations (3)
| Title |
|---|
| 2-苯基吲哚合成的研究;钱明等;《山东化工》;20011231;第30卷(第3期);第8-10页 * |
| 2-苯基吲哚的合成—推荐一个大学有机化学实验;李厚金等;《大学化学》;20141031;第29卷(第5期);第75-78页 * |
| 超声辐射下2-苯基吲哚的合成;蔡可迎等;《化工中间体》;20070430(第4期);第5-6页 * |
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| Publication number | Publication date |
|---|---|
| CN105384675A (en) | 2016-03-09 |
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Granted publication date: 20170825 Termination date: 20181221 |