CN1308075A - Preparation of propyl-2-methyl-3-furan dithioether - Google Patents
Preparation of propyl-2-methyl-3-furan dithioether Download PDFInfo
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- CN1308075A CN1308075A CN 01100084 CN01100084A CN1308075A CN 1308075 A CN1308075 A CN 1308075A CN 01100084 CN01100084 CN 01100084 CN 01100084 A CN01100084 A CN 01100084A CN 1308075 A CN1308075 A CN 1308075A
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Abstract
The present invention provides a preparation method of propyl2-methyl-3-furyldithioether. Said preparation method includes the following steps: at normal pressure and under the condition of zero temperature to refluxing temp. making 1-halopropane react with sodium thiosulfate to obtain a mixture, then 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 propyl group 2-methyl-3-furan dithioether.Propyl group 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 propyl group 2-methyl-3-furan dithioether is represented with 2-methyl-3-furanthiol and dipropyl disulfide:
Main process is: at first under agitation sodium propylate is added in the dipropyl 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, dipropyl 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 propyl group 2-methyl-3-furan dithioether is to solve the problem that aforesaid method exists.
Preparation method of the present invention does not use dipropyl 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 propyl group 2-methyl-3-furan dithioether, it is characterized in that with 2-methyl-3-furanthiol, 1-halogenopropane and Sulfothiorine be raw material, preparation propyl group 2-methyl-3-furan dithioether.The 1-halogenopropane 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:
X is CI, Br, I in the formula.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 the 1-halogenopropane 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 propyl group 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.
Propyl group 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 1-halogenopropane, 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 propyl group 2-methyl of the present invention-3-furan dithioether will be described more specifically by the following examples.
The preparation of embodiment 1 propyl group 2-methyl-3-furan dithioether
In having the 500ml four-hole boiling flask of electric mixer, nitrogen ingress pipe, thermometer and dropping funnel, add 79g Sulfothiorine, 300ml deionized water, stirred 0.5 hour under the room temperature.Stir and drip 62g 1-N-PROPYLE BROMIDE down, add the back and refluxed 1 hour.Mixture is cooled to 0～5 ℃, and the mixed solution of Dropwise 5 7g 2-methyl-3-furanthiol and 85g piperidines adds the back and continues to stir 2 hours.Mixture is used the 50ml 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 76～79 ℃/187Pa cut is product.Product is a light yellow transparent liquid, has barbecue fragrance.
The preparation of embodiment 2 propyl group 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 79g n-propyl chloride then, add the back and refluxed 1 hour.Mixture is cooled to 3 ℃, maintains the temperature at 10～15 ℃, drips the solution that 114g 2-methyl-3-furanthiol, 40g sodium hydroxide and 100ml water are made into, and is warming up to 60 ℃ of restir after adding 1 hour.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 roast beef fragrance.
The preparation of embodiment 3 propyl group 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, 600ml deionized water, drip the 170g propyl iodide under the stirring at room, add the back and stirred 1 hour.Mixture is cooled to 5 ℃, maintains the temperature at 5～10 ℃, drips the 114g 2-solution that methyl-3-furanthiol 81ml pyridine is made into, and adds the back and continues to stir 1 hour.The mixture chloroform extraction, each 100ml, coextraction 3 times.Three extract anhydrous sodium sulfate dryings.Normal pressure reclaims trichloromethane, the resistates underpressure distillation, and collecting 76～79 ℃/187Pa cut is product.Product is a light yellow transparent liquid, has roast beef fragrance.
The preparation of embodiment 4 propyl group 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, 2500ml deionized water, stirred 0.5 hour under the room temperature.Stir down and drip the 395g n-propyl chloride, add the back and refluxed 2 hours.Reaction mixture is cooled to room temperature, and the solution that Dropwise 5 70g 2-methyl-3-furanthiol, 280g potassium hydroxide and 1000ml water are made into was warming up to 60 ℃ of restir 2 hours after adding.Mixture is respectively with 500ml 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 76～79 ℃/187Pa cut is product.Product is a light yellow transparent liquid, has barbecue fragrance.
Claims (3)
1, the preparation method of a kind of propyl group 2-methyl-3-furan dithioether is characterized in that with 2-methyl-3-furyl mercaptan, Sulfothiorine and 1-halogenopropane be feedstock production propyl group 2-methyl-3-furan dithioether, and reaction equation is:
X is CI, Br, I in the formula.
2, the preparation method of a kind of propyl group 2-methyl according to claim 1-3-furan dithioether, it is characterized in that the 1-halogenopropane 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 propyl group 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.
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| CN 01100084 CN1308075A (en) | 2001-01-09 | 2001-01-09 | Preparation of propyl-2-methyl-3-furan dithioether |
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| CN 01100084 CN1308075A (en) | 2001-01-09 | 2001-01-09 | Preparation of propyl-2-methyl-3-furan dithioether |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106032360A (en) * | 2015-03-10 | 2016-10-19 | 江苏兄弟维生素有限公司 | Preparation method of thiamine propyl disulfide |
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2001
- 2001-01-09 CN CN 01100084 patent/CN1308075A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106032360A (en) * | 2015-03-10 | 2016-10-19 | 江苏兄弟维生素有限公司 | Preparation method of thiamine propyl disulfide |
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