CN1193018A - Process for preparing alky 2-methyl-3-furyl-disulfo ether - Google Patents
Process for preparing alky 2-methyl-3-furyl-disulfo ether Download PDFInfo
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- CN1193018A CN1193018A CN97100647A CN97100647A CN1193018A CN 1193018 A CN1193018 A CN 1193018A CN 97100647 A CN97100647 A CN 97100647A CN 97100647 A CN97100647 A CN 97100647A CN 1193018 A CN1193018 A CN 1193018A
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Abstract
The preparation method of alkyl 2-methyl-3-furyl disulfide ether includes the following steps: under the condition of normal pressure and zero deg.C to reflex temp. making alkyl halide react with sodium thiosulfate, then making the obtained mixture react with alkali solution of 2-methyl-3-furamercaptan to obtain the invented product. The obtained alkyl-2-methyl-3-furyl disulfide ether can be used to prepare edible perfume compound.
Description
The present invention relates to the preparation method of a kind of alkyl 2-methyl-3-furan dithioether.Alkyl 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 alkyl 2-methyl-3-furan dithioether is represented with 2-methyl-3-furanthiol and dialkyl group disulfide:
Wherein R is an alkyl, and main process is: at first under agitation sodium methylate is added in the dialkyl group disulfide, then, add 2-methyl-3-furanthiol gradually, react generation alkyl 2-methyl-3-furan dithioether after about 20 hours.Preparation process mainly experiences following step: see Fig. 3.
The subject matter that aforesaid method exists: the one, the dialkyl group 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 alkyl 2-methyl-3-furan dithioether is to solve the problem that aforesaid method exists.
Preparation method of the present invention does not use the dialkyl group 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 is very little.
The present invention relates to the preparation method of the alkyl 2-methyl-3-furan dithioether of formula (I):
(I) alkyl 2-methyl-3-furan dithioether
R is an alkyl in the formula (I).It is characterized in that with 2-methyl-3-furanthiol, haloalkane and Sulfothiorine be raw material, preparation alkyl 2-methyl-3-furan dithioether.Haloalkane 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:
Wherein R is an alkyl, and X is Cl, Br or I.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 haloalkane 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 alkyl 2-methyl-3-furan dithioether by underpressure distillation or wet distillation.
Among the preparation method of the present invention, when R can adopt the wet distillation product separation during for methyl, when R preferably adopts the method product separation of underpressure distillation during for other alkyl.When adopting the underpressure distillation product separation, use solvent extraction earlier, preferred solvent is ether, methylene dichloride, trichloromethane, benzene and sherwood oil.
Alkyl 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 accompanying drawing 1. Fig. 2.
Fig. 1 methyl 2-methyl-3-furan dithioether mass spectrum
Fig. 2 propyl group 2-methyl-3-furan dithioether mass spectrum
Fig. 3 preparation process process flow sheet
Preparation method of the present invention has overcome existing preparation method's shortcoming, and major advantage is:
1. preparation method of the present invention is with equimolar alkyl halide, sodium thiosulfate and 2-methyl-3-furans sulphur The alcohol reaction, reactant almost all transforms, and post processing is easy to.
2. the reaction time shortens greatly.
3. accessory substance is few.
The preparation method of alkyl 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 158g Sulfothiorine, 500ml deionized water, stir under the room temperature and make the Sulfothiorine dissolving.Under stirring at room, drip the 142g methyl iodide then, add the back and refluxed 1 hour.Mixture is cooled to 10 ℃, 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 barbecue fragrance.
The preparation of embodiment 2 ethyl 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, 300ml deionized water, stir under the room temperature and make the Sulfothiorine dissolving.Dropwise 5 5g monobromethane under stirring at room adds the back and stirred 1 hour then, and 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 100ml 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 80-90 ℃/760Pa cut is product.Product is a light yellow transparent liquid.
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 79g n-propyl chloride 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 solution that 114g 2-methyl-3-furanthiol and 81ml pyridine are 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.
Claims (3)
1. the preparation method of alkyl 2-methyl-3-furan dithioether is characterized in that with 2-methyl-3-furanthiol, Sulfothiorine and haloalkane be feedstock production alkyl 2-methyl-3-furan dithioether, and reaction equation is:
Wherein R is an alkyl, and X is Cl, Br or I.
2. the preparation method of a kind of alkyl 2-methyl according to claim 1-3-furan dithioether, it is characterized in that haloalkane 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 alkyl 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 |
|---|---|---|---|
| CN97100647A CN1193018A (en) | 1997-03-07 | 1997-03-07 | Process for preparing alky 2-methyl-3-furyl-disulfo ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN97100647A CN1193018A (en) | 1997-03-07 | 1997-03-07 | Process for preparing alky 2-methyl-3-furyl-disulfo ether |
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| CN1193018A true CN1193018A (en) | 1998-09-16 |
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| CN97100647A Pending CN1193018A (en) | 1997-03-07 | 1997-03-07 | Process for preparing alky 2-methyl-3-furyl-disulfo ether |
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1997
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