CN108727254A - A kind of synthetic method of 4- picolines quaternary ammonium salt - Google Patents
A kind of synthetic method of 4- picolines quaternary ammonium salt Download PDFInfo
- Publication number
- CN108727254A CN108727254A CN201710264551.2A CN201710264551A CN108727254A CN 108727254 A CN108727254 A CN 108727254A CN 201710264551 A CN201710264551 A CN 201710264551A CN 108727254 A CN108727254 A CN 108727254A
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- temperature
- picolines
- synthetic method
- ammonium salt
- quaternary ammonium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a kind of synthetic methods of 4- picolines quaternary ammonium salt.Include the following steps：4- picolines are dissolved in a certain amount of solvent, certain temperature is cooled to, dimethyl suflfate are then added dropwise, and control temperature, after being added dropwise, are warming up to certain temperature, continues to keep the temperature 5-6h, filter, wash, it is dry.
Description
Technical field
The present invention relates to a kind of synthetic methods of 4- picolines quaternary ammonium salt
Background technology
Pyridine quaternary ammonium salt can be made by pyridine and hydrocarbylating agent, be a kind of ionic compound, intermolecular dependence
The more ionic bonds bigger than Van der Waals force combine, and can be used as phase transfer catalyst, polymerization initiator, the antibacterial used on a large scale
Agent, enzyme inhibitor, acylating reagent, dyestuff, cationic surfactant, asphalt emulsifier etc..
Quaternized pyridinium salt cation has the easy transfer of good flatness, electronics, delocalization good, the suction electricity on nitrogen-atoms
Sub- effect makes the chemical property of pyridylium more active, and nucleophilic addition, Michael addition reaction, 1 can occur,
3 dipole polarization addition reactions, nucleophilic displacement of fluorine and rearrangement reaction are the good synthetic agents of synthesizing heterocyclic compound, in synthesis chemistry
In be widely used.Therefore the synthesis of research pyridine quaternary ammonium salt is of great significance.
4- picolines quaternary ammonium salt of the present invention is a kind of important intermediate of synthesis photosensitive monomer, but due to present
The 4- picolines quaternary ammonium salt of production directly carries out next step reaction in the solution, not by crystallization and purification, is unfavorable for season
The industrialization and storage of ammonium salt.
Therefore in order to overcome the problems referred above, 4- picolines quaternary ammonium salt is individually handled, is finally obtained brilliant with rule
Type 4- picoline quaternary ammonium salts, color are white, crystal form rule.
Advantages of the present invention：Process safety, temperature-controllable and the condition there is no high temperature and pressure, crystallization process need not drop
Temperature, reaction, which finishes, directly obtains crystal, substantially reduces the reaction time, haves laid a good foundation for its industrialization.
Invention content
The object of the present invention is to provide a kind of safety, efficiently, easy, high income, product purity high 4- picoline seasons
The synthetic method of ammonium salt.
Specific implementation mode
It is further illustrated the present invention with reference to embodiment, rather than limits the present invention.
Embodiment 1：
（1）30ml toluene is added in 500ml there-necked flasks, 10 grams of 4- picolines are then added, is cooled to 10 DEG C, stirring is molten
Solution.
（2）13.7 grams of dimethyl suflfates are added in the form of being added dropwise in above-mentioned system, maintain the temperature at 5 DEG C -10 DEG C
（3）After being added dropwise, 20 DEG C or so are warming up to, continues to keep the temperature 5-6h, sample detection.
（4）Reaction finishes, and filters, washs, dries, and obtains 10.7 grams of products, yield 85.6%
Embodiment 2：
（1）30ml acetone is added in 500ml there-necked flasks, 10 grams of 4- picolines are then added, is cooled to 10 DEG C, stirring is molten
Solution.
（2）13.7 grams of dimethyl suflfates are added in the form of being added dropwise in above-mentioned system, maintain the temperature at 5 DEG C -10 DEG C
（3）After being added dropwise, 20 DEG C or so are warming up to, continues to keep the temperature 5-6h, sample detection.
（4）Reaction finishes, and filters, washs, dries, and obtains 11.2 grams of products, yield 89.6%
Embodiment 3：
（1）30ml methanol is added in 500ml there-necked flasks, 10 grams of 4- picolines are then added, is cooled to 10 DEG C, stirring is molten
Solution.
（2）13.7 grams of dimethyl suflfates are added in the form of being added dropwise in above-mentioned system, maintain the temperature at 5 DEG C -10 DEG C
（3）After being added dropwise, 20 DEG C or so are warming up to, continues to keep the temperature 5-6h, sample detection.
（4）After completion of the reaction, 2 DEG C, crystallization 1h are cooled to, filters, washing, dry, obtain 9.5 grams of products, yield 76%.
Claims (5)
1. a kind of synthetic method of 4- picolines quaternary ammonium salt, which is characterized in that include the following steps：
（1）4- picolines are dissolved in a certain amount of solvent, certain temperature is cooled to.
（2）Dimethyl suflfate is added dropwise into above-mentioned system, and controls temperature.
（3）After being added dropwise, it is warming up to certain temperature, continues to keep the temperature 5-6h.
2. synthetic method according to claim 1, which is characterized in that step（1）Used in solvent be methanol, toluene,
One or more of acetone.
3. synthetic method according to claim 1, which is characterized in that step（1）Described in temperature be 10 DEG C or less.
4. synthetic method according to claim 1, which is characterized in that step（2）Described in temperature be 5 DEG C -10 DEG C.
5. synthetic method according to claim 1, which is characterized in that step（3）Described in temperature be 18 DEG C -22 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710264551.2A CN108727254A (en) | 2017-04-21 | 2017-04-21 | A kind of synthetic method of 4- picolines quaternary ammonium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710264551.2A CN108727254A (en) | 2017-04-21 | 2017-04-21 | A kind of synthetic method of 4- picolines quaternary ammonium salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108727254A true CN108727254A (en) | 2018-11-02 |
Family
ID=63933778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710264551.2A Pending CN108727254A (en) | 2017-04-21 | 2017-04-21 | A kind of synthetic method of 4- picolines quaternary ammonium salt |
Country Status (1)
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| CN (1) | CN108727254A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115678152A (en) * | 2021-07-27 | 2023-02-03 | 中国石油化工股份有限公司 | Thermal-aging-resistant asphalt modifier and preparation method and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323362A (en) * | 1979-01-18 | 1982-04-06 | Basf Aktiengesellschaft | Dyed paper |
| JPS6325581B2 (en) * | 1983-04-18 | 1988-05-26 | Kogyo Gijutsu Incho | |
| CN101454398A (en) * | 2006-03-24 | 2009-06-10 | 莱雅公司 | Dyeing composition containing a thiol/disulphide fluorescent colorant comprising a heterocycle, with an external cationic charge, and method for lightening keratin materials using said colorant |
| CN102070769A (en) * | 2009-11-23 | 2011-05-25 | 比亚迪股份有限公司 | Pyridine quaternary ammonium salt polyurethane and preparation method thereof |
| CN105693599A (en) * | 2016-04-02 | 2016-06-22 | 田菱精细化工（大连）有限公司 | Synthesis method of novel SBQ photosensitive monomer |
| CN105777623A (en) * | 2016-02-29 | 2016-07-20 | 北京颖泰嘉和生物科技股份有限公司 | Method for preparing pyridine side chain methyl quaternary ammonium compound |
-
2017
- 2017-04-21 CN CN201710264551.2A patent/CN108727254A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323362A (en) * | 1979-01-18 | 1982-04-06 | Basf Aktiengesellschaft | Dyed paper |
| JPS6325581B2 (en) * | 1983-04-18 | 1988-05-26 | Kogyo Gijutsu Incho | |
| CN101454398A (en) * | 2006-03-24 | 2009-06-10 | 莱雅公司 | Dyeing composition containing a thiol/disulphide fluorescent colorant comprising a heterocycle, with an external cationic charge, and method for lightening keratin materials using said colorant |
| CN102070769A (en) * | 2009-11-23 | 2011-05-25 | 比亚迪股份有限公司 | Pyridine quaternary ammonium salt polyurethane and preparation method thereof |
| CN105777623A (en) * | 2016-02-29 | 2016-07-20 | 北京颖泰嘉和生物科技股份有限公司 | Method for preparing pyridine side chain methyl quaternary ammonium compound |
| CN105693599A (en) * | 2016-04-02 | 2016-06-22 | 田菱精细化工（大连）有限公司 | Synthesis method of novel SBQ photosensitive monomer |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115678152A (en) * | 2021-07-27 | 2023-02-03 | 中国石油化工股份有限公司 | Thermal-aging-resistant asphalt modifier and preparation method and application thereof |
| CN115678152B (en) * | 2021-07-27 | 2023-11-03 | 中国石油化工股份有限公司 | Thermal aging resistant asphalt modifier and preparation method and application thereof |
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