CN1308076A - Preparation of methyl-2-methyl-3-furan dithioether - Google Patents
Preparation of methyl-2-methyl-3-furan dithioether Download PDFInfo
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- CN1308076A CN1308076A CN 01100085 CN01100085A CN1308076A CN 1308076 A CN1308076 A CN 1308076A CN 01100085 CN01100085 CN 01100085 CN 01100085 A CN01100085 A CN 01100085A CN 1308076 A CN1308076 A CN 1308076A
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- furan
- dithioether
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Abstract
The present invention provides a preparation method of methyl 2-methyl-3-furyldithioether. Said method includes the following steps: at normal pressure and under the condition of zero temp. to refluxing temp. making dimethyl carbonate or iodomethane react with sodium thiosulfate, and them making the obtained mixture react with alkaline solution of 2-methyl-3-furanthiol so as to obtain the invented product which can be used for preparing food essence.
Description
The present invention relates to the preparation method of a kind of methyl 2-methyl-3-furan dithioether.Methyl 2-methyl-3-furan dithioether is a kind of important flavoring compounds, uses very extensive in various food flavours especially seasoning essence.
Existing is that the available following reaction equation of method (English Patent 1538073) of feedstock production methyl 2-methyl-3-furan dithioether is represented with 2-methyl-3-furanthiol and dimethyl disulfide:
Main process is: at first under agitation sodium methylate is added in the dimethyl disulfide, then, add 2-methyl-3-furanthiol gradually, react generation methyl 2-methyl-3-furan dithioether after about 20 hours.
The subject matter that aforesaid method exists: the one, dimethyl disulfide is excessive in a large number, brings very big difficulty to aftertreatment; The 2nd, long reaction time; The 3rd, raw material 2-methyl-3-furanthiol transforms complete inadequately; The 4th, by product two (2-methyl-3-furyl) disulfide amount is more.
The preparation method who the purpose of this invention is to provide a kind of improved methyl 2-methyl-3-furan dithioether is to solve the problem that aforesaid method exists.
Preparation method of the present invention does not use dimethyl disulfide to be raw material, and the reaction times shortens dramatically, and 2-methyl-3-furanthiol is total overall reaction almost, and the amount of by product two (2-methyl-3-furyl) disulfide seldom.
The present invention relates to the preparation method of methyl 2-methyl-3-furan dithioether, it is characterized in that with 2-methyl-3-furanthiol, methylcarbonate or methyl iodide and Sulfothiorine be raw material, preparation methyl 2-methyl-3-furan dithioether.Methylcarbonate or methyl iodide earlier with the Sulfothiorine reaction, resulting mixture again with the alkaline solution reaction of 2-methyl-3-furanthiol.The alkaline solution of preparation 2-methyl-3-furanthiol can be used mineral alkali, as sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood; Also can use organic bases, as pyridine, piperidines, triethylamine etc.
Reaction equation:
Preparation method of the present invention is reflected in the aqueous solution and carries out, and operation is very easy.Its main process is: add Sulfothiorine and deionized water in the reactor, under stirring Sulfothiorine is dissolved fully, drip methylcarbonate or methyl iodide then, add the back and stir to reflux temperature in room temperature.After finishing, reaction continues to stir the alkaline solution that drips 2-methyl-3-furanthiol down.After reaction finishes, obtain methyl 2-methyl-3-furan dithioether by underpressure distillation or wet distillation.
Among the preparation method of the present invention, can adopt the wet distillation product separation, also can adopt the method product separation of underpressure distillation.When adopting the underpressure distillation product separation, use solvent extraction earlier, preferred solvent is ether, methylene dichloride, trichloromethane, benzene and sherwood oil.
Methyl 2-methyl-3-furan dithioether with the inventive method preparation has been confirmed its structure by the chromatography-mass spectroscopy on-line analysis.Mass spectrometry results is seen Fig. 1.
Preparation method of the present invention has overcome existing preparation method's shortcoming, and major advantage is:
1, preparation method of the present invention reacts with equimolar methylcarbonate or methyl iodide, Sulfothiorine and 2-methyl-3-furanthiol, and reactant almost all transforms, and aftertreatment is easy to.
2, the reaction times shortens greatly.
3, by product is few.
The preparation method of methyl 2-methyl of the present invention-3-furan dithioether will be described more specifically by the following examples.
The preparation of embodiment 1 methyl 2-methyl-3-furan dithioether
In having the 1000ml four-hole boiling flask of electric mixer, nitrogen ingress pipe, thermometer and dropping funnel, add 79g Sulfothiorine, 250ml deionized water, stir under the room temperature and make the Sulfothiorine dissolving.Under stirring at room, drip the 49g methylcarbonate then, add the back and refluxed 1 hour.Mixture is cooled to 10 ℃, maintains the temperature at 10～15 ℃, and the solution that Dropwise 5 7g 2-methyl-3-furanthiol, 40g sodium hydroxide and 100ml water are made into was warming up to 60 ℃ of restir 1 hour after adding.The mixture wet distillation is till no oily matter distillates to the distillate.After the distillate cooling, tell organic phase, with promptly obtaining product behind the anhydrous sodium sulfate drying.Product is a light yellow transparent liquid, has barbecue fragrance.
The preparation of embodiment 2 methyl 2-methyl-3-furan dithioethers
In having the 500ml four-hole boiling flask of electric mixer, nitrogen ingress pipe, thermometer and dropping funnel, add 79g Sulfothiorine, 250ml deionized water, stir under the room temperature and make the Sulfothiorine dissolving.Under stirring at room, drip the 71g methyl iodide then, add the back and stirred 1 hour.Mixture is cooled to 0 ℃, maintains the temperature at 0～5 ℃, and the solution that Dropwise 5 7g 2-methyl-3-furanthiol, 56g potassium hydroxide and 80ml water are made into adds the back and continues to stir 1 hour.The mixture extracted with diethyl ether, each 50ml, coextraction 3 times.Three extract anhydrous sodium sulfate dryings.Normal pressure reclaims ether, the resistates underpressure distillation, and collecting 75 ℃/733Pa cut is product.Product is a light yellow transparent liquid, has barbecue fragrance.
The preparation of embodiment 3 methyl 2-methyl-3-furan dithioethers
In having the 1000ml four-hole boiling flask of electric mixer, nitrogen ingress pipe, thermometer and dropping funnel, add 158g Sulfothiorine, 500ml deionized water, stir under the room temperature and make the Sulfothiorine dissolving.Under stirring at room, drip the 98g methylcarbonate then, add under the room temperature of back and stirred 3 hours.Drip the solution that 114g 2-methyl-3-furanthiol, 56g potassium hydroxide and 200ml water are made under the room temperature, be warming up to 60 ℃ of restir after adding 2 hours.Mixture is respectively with 100ml benzene extraction 3 times.Use the Anhydrous potassium carbonate drying after merging organic phase.Benzene is reclaimed in air distillation, the resistates underpressure distillation, and collecting 75 ℃/733Pa cut is product.Product is a light yellow transparent liquid, has barbecue fragrance.
The preparation of embodiment 4 methyl 2-methyl-3-furan dithioethers
In having the 5000ml four-hole boiling flask of electric mixer, nitrogen ingress pipe, thermometer and dropping funnel, add 790g Sulfothiorine, 3000ml deionized water, stirred 0.5 hour under the room temperature.Stir down and drip the 710g methyl iodide, add the back and refluxed 1 hour.Mixture is cooled to 0～5 ℃, and the solution that Dropwise 5 70g 2-methyl-3-furanthiol, 400g sodium hydroxide and 1000ml water are made into adds the back and continues to stir 2 hours.Mixture is used the 300ml dichloromethane extraction respectively 3 times.Organic phase is used dried over anhydrous sodium carbonate after merging.The air distillation organic phase reclaims methylene dichloride, the resistates underpressure distillation, and collecting 75 ℃/733Pa cut is product.Product is a light yellow transparent liquid, has barbecue fragrance.
Claims (3)
1, the preparation method of a kind of methyl 2-methyl-3-furan dithioether is characterized in that with 2-methyl-3-furyl mercaptan, Sulfothiorine and methylcarbonate or methyl iodide be feedstock production methyl 2-methyl-3-furan dithioether, and reaction equation is:
2, the preparation method of a kind of methyl 2-methyl according to claim 1-3-furan dithioether, it is characterized in that methylcarbonate or methyl iodide earlier with the Sulfothiorine reaction, resulting mixture again with the alkaline solution reaction of 2-methyl-3-furanthiol.
3, the preparation method of a kind of methyl 2-methyl according to claim 1-3-furan dithioether is characterized in that the alkaline solution of preparing 2-methyl-3-furyl mercaptan can use mineral alkali, as: sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood; Also can use organic bases, as: pyridine, piperidines, triethylamine etc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 01100085 CN1308076A (en) | 2001-01-09 | 2001-01-09 | Preparation of methyl-2-methyl-3-furan dithioether |
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| CN 01100085 CN1308076A (en) | 2001-01-09 | 2001-01-09 | Preparation of methyl-2-methyl-3-furan dithioether |
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| CN 01100085 Pending CN1308076A (en) | 2001-01-09 | 2001-01-09 | Preparation of methyl-2-methyl-3-furan dithioether |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI400040B (en) * | 2006-10-13 | 2013-07-01 | Ogawa & Co Ltd | Perfume composition |
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2001
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI400040B (en) * | 2006-10-13 | 2013-07-01 | Ogawa & Co Ltd | Perfume composition |
| US9167836B2 (en) | 2006-10-13 | 2015-10-27 | Ogawa & Co., Ltd. | Perfume composition |
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