CN101735130A - Method for preparing dimethyl diselenide - Google Patents
Method for preparing dimethyl diselenide Download PDFInfo
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- CN101735130A CN101735130A CN201010019464A CN201010019464A CN101735130A CN 101735130 A CN101735130 A CN 101735130A CN 201010019464 A CN201010019464 A CN 201010019464A CN 201010019464 A CN201010019464 A CN 201010019464A CN 101735130 A CN101735130 A CN 101735130A
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- selenium powder
- alkali metal
- metal salt
- dimethyl diselenide
- diselenide
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Abstract
The invention discloses a method for preparing dimethyl diselenide, which comprises the following steps: adding selenium powder into borohydride alkali metal salt solution, reacting the selenium powder at the normal temperature, and heating the solution to perform full reaction on the selenium powder after the reaction is stable so as to obtain diselenide alkali metal salt solution; and stirring the solution at the room temperature, dripping methyl iodide into the obtained diselenide alkali metal salt solution, stirring and reacting the solution, standing and demixing the solution, demixing the lower layer, and washing the sediment to obtain the dimethyl diselenide. The method of the invention has mild reaction condition, can be carried out at the normal temperature and the normal pressure, has no special requirement for equipment and operations, and is suitable for large-scale industrialized production.
Description
Technical field
The present invention relates to a kind of preparation method of dimethyl diselenide.
Background technology
Selenium is one of necessary trace element of animal body, and it is to keep animal normal growth and breeding trace elements necessary.China has 100,000,000 to lack selenium or low selenium approximately at present, suffers from or very easily generation and scarce selenium diseases associated.Then mainly utilize organic selenium compounds to come supplement selenium abroad.Domestic inorganic salt Sodium Selenite sheet or the Sodium Selenite nutrient fortified food of generally utilizing comes supplement selenium.
Sodium methyl-hydroselenide is a kind of important intermediate in the organic synthesis, is usually used in synthetic various organic selenide, is the important source material of synthetic medicine, food and animal feedstuff additive and agricultural chemicals, has a very wide range of applications in a lot of reactions.Commonly be used to synthesize " selenomethionine " and " selenium-methyl selenium substituted aminothiopropionic ".
Synthetic sodium methyl-hydroselenide is many to be intermediate with the dimethyl diselenide, so plan manages to determine synthetic the play decisive role of the route of synthesization of dimethyl two selenium to sodium methyl-hydroselenide.The relatively complicated and high inadequately reason of productive rate does not still have suitability for industrialized production at present owing to the synthesis technique of dimethyl diselenide but for a long time.
Abroad, common metal sodium, selenium powder etc. obtain dimethyl diselenide through 2 step reactions in liquefied ammonia, and the raw materials used cost of this process is higher relatively, and reaction conditions is comparatively harsh, and sodium Metal 99.5 is a kind of hazardous chemical, are unfavorable for safety in production; Domestic also have the people with selenium powder, reagent such as hydrazine hydrate are that reaction makes dimethyl diselenide to raw material through 2 steps, the used reactant of this process is more common reagent, reaction conditions is loose, but all consumption of unexposed reactant and reaction conditions, operation steps is unclear, and data are few, and verity and reliability are worth suspecting; In addition, the somebody attempts using selenium powder, sodium hydroxide, and cetyl trimethylammonium bromides etc. prepare target product with the potassiumiodide effect again for reagent obtains two sodium selenides under nitrogen protection.Though this method reaction possibility of success is big, reactant is complicated, and reaction conditions relatively harsher (needing nitrogen protection and ice bath).
All there is the operational path complexity in traditional synthesis process, and yield is low, and facility investment is big, is difficult to realize suitability for industrialized production.
Summary of the invention
In order to overcome the problems referred to above, the invention provides a kind of reaction conditions gentleness, the dimethyl diselenide preparation method who is easy to control.
The technical solution used in the present invention is:
A kind of preparation method of dimethyl diselenide may further comprise the steps:
Selenium powder is added in the hydroboration alkali metal salt soln, and normal temperature is reaction down, and behind the reacting balance, heating reacts completely selenium powder, obtains two selenizing alkali metal salt solns;
Under stirring at room, methyl iodide is added drop-wise in the two selenizing alkali metal salt solns of above-mentioned gained, stirring reaction, standing demix is told lower floor, through washing, obtains dimethyl diselenide.。
The invention has the beneficial effects as follows: the reaction conditions gentleness, can carry out at normal temperatures and pressures, to equipment and the no particular requirement of operation, be suitable for large-scale industrial production.
Description of drawings
Fig. 1 is the infrared spectrum of product of the present invention.
Embodiment
Below in conjunction with example, further specify the present invention.
Embodiment 1
1) 1.55g (0.02mol) selenium powder is added in the 12mL water, stir, obtain the selenium powder aqueous suspensions;
2) with 0.04molKBH
4Be dissolved in the 12.5mL water, stir the above-mentioned selenium powder aqueous suspensions of adding down, behind the reacting balance, add 1.55g (0.02mol) selenium powder again, behind the stirring 15min, heated and stirred obtains two potassium selenide solution to the selenium powder complete reaction in 100 ℃ electric mantle;
3) under stirring at room, the 7.1g methyl iodide is dropped to above-mentioned two potassium selenide solution, added in about 1 minute, 25 ℃ of stirring reactions 2 hours, standing demix is told lower floor, through washing, obtains orange oily dimethyl diselenide, and yield is 86%.
Embodiment 2
1) 1.55g (0.02mol) selenium powder is added in the 12mL water, stir, obtain the selenium powder aqueous suspensions;
2) with 0.04mol NaBH
4Be dissolved in the 12.5mL water, stir the above-mentioned selenium powder aqueous suspensions of adding down, behind the reacting balance, add 1.55g (0.02mol) selenium powder again, behind the stirring 15min, heated and stirred obtains two potassium selenide solution to the selenium powder complete reaction in 100 ℃ electric mantle;
3) under stirring at room, the 7.1g methyl iodide is dropped to above-mentioned two potassium selenide solution, added in about 1 minute, 25 ℃ of stirring reactions 2 hours, standing demix is told lower floor, through washing, obtains orange oily dimethyl diselenide, and yield is 88%.
Embodiment 3
1) 1.55g (0.02mol) selenium powder is added in the 12mL water, stir, obtain the selenium powder aqueous suspensions;
2) with 0.06mol NaBH
4Be dissolved in the 12.5mL water, stir the above-mentioned selenium powder aqueous suspensions of adding down, behind the reacting balance, add 1.55g (0.02mol) selenium powder again, behind the stirring 15min, heated and stirred obtains two potassium selenide solution to the selenium powder complete reaction in 100 ℃ electric mantle;
3) under stirring at room, the 7.1g methyl iodide is dropped to above-mentioned two potassium selenide solution, added in about 1 minute, 25 ℃ of stirring reactions 2 hours, standing demix is told lower floor, through washing, obtains orange oily dimethyl diselenide, and yield is 85%.
Embodiment 4
1) 1.55g (0.02mol) selenium powder is added in the 12mL water, stir, obtain the selenium powder aqueous suspensions;
2) with 0.05mol KBH
4Be dissolved in the 12.5mL water, stir the above-mentioned selenium powder aqueous suspensions of adding down, behind the reacting balance, add 1.55g (0.02mol) selenium powder again, behind the stirring 15min, heated and stirred obtains two potassium selenide solution to the selenium powder complete reaction in 100 ℃ electric mantle;
3) under stirring at room, the 7.1g methyl iodide is dropped to above-mentioned two potassium selenide solution, added in about 1 minute, 25 ℃ of stirring reactions 2 hours, standing demix is told lower floor, through washing, obtains orange oily dimethyl diselenide, and yield is 87%.
Sample wire among Fig. 1 is the infrared rays spectrogram of the embodiment of the invention 1 product, is characterized by dimethyl diselenide.
The inventive method reaction conditions gentleness can be carried out at normal temperatures and pressures, to equipment and the no particular requirement of operation, is suitable for large-scale industrial production.
Among the present invention, selenium powder adds at twice, and easier reaction reacts also more complete, has improved expensive selenium powder utilization ratio of raw materials, has reduced product cost.
Claims (5)
1. the preparation method of a dimethyl diselenide may further comprise the steps:
1) selenium powder is added in the hydroboration alkali metal salt soln, normal temperature is reaction down, and behind the reacting balance, heating reacts completely selenium powder, obtains two selenizing alkali metal salt solns;
2) under stirring at room, methyl iodide is added drop-wise in the two selenizing alkali metal salt solns of above-mentioned gained, stirring reaction, standing demix is told lower floor, through washing, obtains dimethyl diselenide.
2. the preparation method of a kind of dimethyl diselenide according to claim 1 is characterized in that: earlier selenium powder is mixed with water, make the selenium powder aqueous suspensions, and then react in the adding hydroboration an alkali metal salt.
3. the preparation method of a kind of dimethyl diselenide according to claim 1, it is characterized in that: selenium powder adds at twice.
4. the preparation method of a kind of dimethyl diselenide according to claim 1, it is characterized in that: the adding mol ratio of selenium powder and hydroboration an alkali metal salt is 1: 1～1.5.
5. the preparation method of a kind of dimethyl diselenide according to claim 1, it is characterized in that: described hydroboration an alkali metal salt comprises KBH
4, NaBH
4
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010019464A CN101735130A (en) | 2010-01-15 | 2010-01-15 | Method for preparing dimethyl diselenide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010019464A CN101735130A (en) | 2010-01-15 | 2010-01-15 | Method for preparing dimethyl diselenide |
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| CN101735130A true CN101735130A (en) | 2010-06-16 |
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| CN201010019464A Pending CN101735130A (en) | 2010-01-15 | 2010-01-15 | Method for preparing dimethyl diselenide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739536A (en) * | 2013-12-04 | 2014-04-23 | 温州大学 | Diaryl diselenide compound synthesis method |
| CN107400074A (en) * | 2017-08-25 | 2017-11-28 | 云南核度生物产业发展有限公司 | A kind of method of one pot process dimethyl diselenide ether |
| CN114716874A (en) * | 2022-05-06 | 2022-07-08 | 安徽强邦新材料股份有限公司 | Hydrophilic treatment-free plate protective adhesive and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100417645C (en) * | 2006-11-02 | 2008-09-10 | 江西川奇药业有限公司 | Method of synthesizing selenium methyl selenium substituted cysteine through methyl seleno acetaldehyde |
-
2010
- 2010-01-15 CN CN201010019464A patent/CN101735130A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100417645C (en) * | 2006-11-02 | 2008-09-10 | 江西川奇药业有限公司 | Method of synthesizing selenium methyl selenium substituted cysteine through methyl seleno acetaldehyde |
Non-Patent Citations (3)
| Title |
|---|
| DANIEL L. KLAYMAN AND T. SCOTT GRIFFIN: "Reaction of Selenium with Sodium Borohydride in Protic Solvents. A Facile Method for the Introduction of Selenium into Organic Molecules", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| 徐才丁: "二硒醚在有机合成中的应用", 《化学试剂》 * |
| 王江等: "硒代蛋氨酸的合成", 《化学工程师》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739536A (en) * | 2013-12-04 | 2014-04-23 | 温州大学 | Diaryl diselenide compound synthesis method |
| CN103739536B (en) * | 2013-12-04 | 2015-07-01 | 温州大学 | Diaryl diselenide compound synthesis method |
| CN107400074A (en) * | 2017-08-25 | 2017-11-28 | 云南核度生物产业发展有限公司 | A kind of method of one pot process dimethyl diselenide ether |
| CN114716874A (en) * | 2022-05-06 | 2022-07-08 | 安徽强邦新材料股份有限公司 | Hydrophilic treatment-free plate protective adhesive and preparation method thereof |
| CN114716874B (en) * | 2022-05-06 | 2022-12-27 | 安徽强邦新材料股份有限公司 | Hydrophilic treatment-free plate protective adhesive and preparation method thereof |
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Application publication date: 20100616 |