CN111100050A - Novel method for synthesizing allicin - Google Patents
Novel method for synthesizing allicin Download PDFInfo
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- CN111100050A CN111100050A CN201811262418.4A CN201811262418A CN111100050A CN 111100050 A CN111100050 A CN 111100050A CN 201811262418 A CN201811262418 A CN 201811262418A CN 111100050 A CN111100050 A CN 111100050A
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
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Abstract
The invention discloses a new method for synthesizing allicin, which is technically characterized in that tetrabutylammonium bromide is used as a phase transfer catalyst to synthesize diallyl trisulfide, thereby shortening the reaction time and improving the yield. The advantages are that: at present, the synthesis is mainly carried out by adopting an allyl chloride-sodium thiosulfate-sodium sulfide method in the industry, but the yield of a two-phase reaction is low because the reactant allyl chloride is insoluble in water. The invention uses tetrabutyl ammonium bromide, TBAI for short as a phase transfer catalyst to synthesize the diallyl trisulfide, shortens the reaction time and improves the yield, and the reaction equation is as follows.
Description
Technical Field
The invention relates to the field of chemical synthesis, in particular to a method for synthesizing diallyl trisulfide serving as a main component of allicin.
Background
Allicin belongs to the medicines for treating deep fungal and bacterial infections, such as fungal infection of lung and digestive tract, candida albicans bacteremia, acute and chronic bacillary dysentery, acute and chronic enteritis, whooping cough and the like, can also be used as a feed additive and a flavor enhancer of food, and the currently common synthesis method is mainly synthesized by adopting an allyl chloride-sodium thiosulfate-sodium sulfide method in the current industry, but because the reactant allyl chloride is insoluble in water, the yield of two-phase reaction is lower, and the reaction equation is as follows:
the invention uses tetrabutylammonium bromide, TBAI for short as a phase transfer catalyst to synthesize the diallyl trisulfide, shortens the reaction time, improves the yield and has important practical significance.
Disclosure of Invention
The invention aims to establish a novel method for synthesizing allicin, which shortens the synthesis time of the main component diallyl trisulfide in the synthesized allicin and improves the yield of products by adding tetrabutylammonium bromide as a phase transfer catalyst in a reaction system, and comprises the following steps:
adding 28-38 g of sodium thiosulfate and 95ml of distilled water into a reaction vessel with a magnetic stirring and refluxing device, stirring, heating to about 35 ℃, adding 1-3.5 g of tetra-n-butylammonium iodide serving as a phase transfer catalyst after the temperature is stable, uniformly stirring, then 9ml of allyl chloride is transferred into a dropping funnel and slowly dropped into a reaction container, the reaction temperature is controlled to be about 5O-60 ℃ for reflux, after reaction for 1.5-2.5 h, cooling to room temperature, dropping 10 mL1.8mol/L sodium sulfide solution into the reaction solution after the temperature is reduced to the room temperature, stirring for 30min at the room temperature, transferring the reaction solution into a separating funnel, standing for 12 h, discarding the lower water phase, washing the oil phase with distilled water for 3 times, separating the water phase to obtain light yellow oily substance, drying with anhydrous sodium sulfate, filtering to remove sodium sulfate, distilling under reduced pressure at 133.33Pa, and collecting the fraction at 59-60 deg.C.
The specific implementation mode is as follows:
example 1 establishment of synthetic route:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature to be about 5O +/-2 ℃ for refluxing, after reacting for 2 hours, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, and standing in a roomStirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower water phase, washing the oil phase with distilled water for 3 times, separating the water phase to obtain light yellow oily substance, and adding anhydrous Na2SO4Drying, filtering to remove Na2SO4. Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield to be 32%;
and (4) conclusion: this example demonstrates that allicin can be prepared in 32% yield and in a low yield by synthesis using the allyl chloride-sodium thiosulfate-sodium sulfide process.
Example 2 selection of catalyst:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.05 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature to about 5O +/-2 ℃, refluxing, reacting for 2 hours, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the aqueous phase to obtain a light yellow oily substance, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield to be 56%;
and (4) conclusion: this example can demonstrate that 0.5% tetrabutylammonium bromide (TBAB) was introduced into the system during the synthesis of allicin using the allyl chloride-sodium thiosulfate-sodium sulfide method, with a 56% yield of diallyl trisulfide, compared to the absence of a phase transfer catalyst. The yield is improved.
Example 3 selection of catalyst concentration:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.1 g of phase transfer catalyst tetra-n-butylammonium iodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, and slowly dropping the allyl chloridePlacing into a reaction bottle, controlling the reaction temperature to be about 5O +/-2 ℃ for reflux, after 2h of reaction, cooling to room temperature, dripping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the aqueous phase to obtain light yellow oily substance, and using anhydrous Na for removing the aqueous phase to obtain light yellow oily substance2SO4Drying, filtering to remove Na2SO4Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield to be 67%;
and (4) conclusion: this example can demonstrate that 1.0% tetrabutylammonium bromide (TBAB) was introduced into the system during the preparation of allicin by the allyl chloride-sodium thiosulfate-sodium sulfide synthesis, with a yield of diallyl trisulfide of 67%. In comparison with example 2, 0.5% tetrabutylammonium bromide was introduced into the system. The yield is improved.
Example 4 selection of catalyst concentration:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.20 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature to about 5O +/-2 ℃ for refluxing, after reacting for 2 hours, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction liquid, stirring at room temperature for 30min, transferring the reaction liquid into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the aqueous phase to obtain light yellow oily substance, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield to be 78%;
and (4) conclusion: this example can demonstrate that 2.0% tetrabutylammonium bromide (TBAB) was introduced into the system during the synthesis of allicin using the allyl chloride-sodium thiosulfate-sodium sulfide method, with a 78% yield of diallyl trisulfide. In comparison with example 3, 1.0% tetrabutylammonium bromide was introduced into the system. The yield is further improved.
Example 5 selection of catalyst concentration:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.30 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature to about 5O +/-2 ℃, refluxing, reacting for 2 hours, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the aqueous phase to obtain a light yellow oily substance, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield to be 72%;
and (4) conclusion: this example can demonstrate that 3.0% tetrabutylammonium bromide (TBAB) was introduced into the system during the synthesis of allicin using the allyl chloride-sodium thiosulfate-sodium sulfide method, with a 72% yield of diallyl trisulfide. Compared with example 4, the yield is reduced by introducing 2.0% of tetrabutylammonium bromide into the system.
Example 6 selection of catalyst concentration:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.35 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature to about 5O +/-2 ℃, refluxing, reacting for 2 hours, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the aqueous phase to obtain a light yellow oily substance, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield to be 71%; .
And (4) conclusion: this example can demonstrate that 3.5% tetrabutylammonium bromide (TBAB) was introduced into the system during the synthesis of allicin using the allyl chloride-sodium thiosulfate-sodium sulfide method, with a diallyl trisulfide yield of 71%. Compared with example 5, 3.0% of tetrabutylammonium bromide is introduced into the system, and the yield is equivalent.
As can be seen from examples 1 to 6, the introduction of tetrabutylammonium bromide (TBAB) into the reaction system can effectively improve the yield of diallyl trisulfide. When the introduction amount is 1.0% -3.5%, the yield of the diallyl trisulfide is over 60%, and when the introduction amount is 2.0%, the yield is highest.
Example 7 selection of reaction time:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping the allyl chloride into the reaction bottle, controlling the reaction temperature to about 5O +/-2 ℃ for refluxing, reacting for 1.0h, 1.5h, 2.0h, 2.5h, 3.0h and 3.5 respectively, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the aqueous phase to obtain light yellow oily matter, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4And carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield as shown in the following table 1:
and (4) conclusion: example 7 can demonstrate that the yield of allicin produced by the allyl chloride-sodium thiosulfate-sodium sulfide synthesis increases with time, and the reaction time reaches the maximum at 3.5 h.
Example 8 selection of catalyst addition reaction time:
a250 mL three-necked round bottom reaction flask with magnetic stirring and refluxing apparatus was charged with 36g of sodium thiosulfate (containing 5 crystal waters) and 95mLDistilled water, stirring and heating to about 35 ℃, adding 0.2 g of phase transfer catalyst tetra-n-butyl amine iodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into a reaction bottle, controlling the reaction temperature to be about 5O +/-2 ℃ for reflux, respectively reacting for 1.0h, 1.5h, 2.0h, 2.5h, 3.0h and 3.5, cooling to room temperature, adding 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the water phase to obtain light yellow oily matter, adding anhydrous Na2SO4Drying, filtering to remove Na2SO4. Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield shown in the following table 2:
and (4) conclusion: example 8 can prove that, in the process of preparing the allicin by adopting the allyl chloride-sodium thiosulfate-sodium sulfide method, the product yield is continuously improved along with the passage of time by introducing tetra-n-butyl ammonium iodide, the reaction time reaches the maximum within 1.5h, and the introduction of the tetra-n-butyl ammonium iodide in the reaction system greatly shortens the reaction time and improves the efficiency. The yield of 78 percent can be achieved after 2 hours; without tetra-n-butyliodinated amine, the reaction took 3.5 hours to reach a 77% yield.
Example 9 selection of reaction temperature:
adding 36g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-opening round bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.2 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature at about 4O +/-2 ℃, 45 +/-2 ℃, 5O +/-2 ℃, 55 +/-2 ℃ and 6O +/-2 ℃, refluxing after reacting for 2.0h, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring for 30min at room temperature, transferring the reaction solution into a separating funnel, standing overnight, removing the lower-layer water phase, washing the oil phase for 3 times with distilled water, and removing waterMixing to obtain light yellow oil, and adding anhydrous Na2SO4Drying, filtering to remove Na2SO4. Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield shown in the following table 3:
and (4) conclusion: it can be seen that the reaction temperature is 50 deg.CoC, the yield was the highest, and example 9 demonstrated that the reaction temperature was 50 deg.CoThe range of C. + -.2 is most suitable.
Example 10 selection of molar ratios of the starting materials for the reaction:
respectively adding 28g, 32g, 34g, 36g, 38g, sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.2 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dropping into the reaction bottle, controlling the reaction temperature to be about 5O +/-2 ℃ for refluxing, after reacting for 2.0h, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction liquid, stirring at room temperature for 30min, transferring the reaction liquid into a separating funnel, standing overnight, discarding the lower water phase, washing the oil phase for 3 times with distilled water, separating the water phase to obtain light yellow oily matter, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4. Carrying out reduced pressure distillation, collecting fractions (59-60 ℃/133.33 Pa), and calculating the yield shown in the following table 4:
and (4) conclusion: from the molar ratio of the starting materials in example 10, 1.5 gave the highest yield, as demonstrated in example 9, the reaction temperature was 50 deg.CoThe range of C. + -.2 is most suitable.
Example 11
A250 mL three-necked round bottom reaction flask with magnetic stirring and refluxing apparatus was charged with 36.2 g of sodium thiosulfate (containing 5 crystal waters) and 95mLDistilled water, stirring and heating to about 35 ℃, adding 0.21 g of phase transfer catalyst tetra-n-butyl amine iodide, then transferring 9.1 mL of allyl chloride into a dropping funnel, slowly dropping into a reaction bottle, controlling the reaction temperature to be about 5O +/-2 ℃ for reflux, after 2h of reaction, cooling to room temperature, dropping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring for 30min at room temperature, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the water phase to obtain light yellow oily matter, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4Then, distillation was carried out under reduced pressure, and fractions (59 to 60 ℃ C./133.33 Pa) were collected to calculate a yield of 78%.
Example 12
Adding 35.8 g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-opening round bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.20 g of phase transfer catalyst tetra-n-butyl amine iodide, then transferring 9.1 mL of allyl chloride into a dropping funnel, slowly dripping into the reaction bottle, controlling the reaction temperature to about 5O +/-2 ℃, refluxing, reacting for 2 hours, cooling to room temperature, dripping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring for 30min at room temperature, transferring the reaction solution into a separating funnel, standing overnight, discarding the lower aqueous phase, washing the oil phase with distilled water for 3 times, separating the water phase to obtain light yellow oily matter, and using anhydrous Na2SO4Drying, filtering to remove Na2SO4The distillation was carried out under reduced pressure, and fractions (59 to 60 ℃ C./133.33 Pa) were collected to calculate a yield of 77%.
Example 13
Adding 36.0 g of sodium thiosulfate (containing 5 crystal water) and 95mL of distilled water into a 250 mL three-mouth round-bottom reaction bottle with a magnetic stirring and refluxing device, stirring and heating to about 35 ℃, adding 0.19 g of phase transfer catalyst tetra-n-butylaminoiodide, then transferring 9.0 mL of allyl chloride into a dropping funnel, slowly dripping into the reaction bottle, controlling the reaction temperature to reflux at about 5O +/-2 ℃, reacting for 2 hours, cooling to room temperature, dripping 10mL of 1.8 mol/L sodium sulfide solution into the reaction solution, stirring at room temperature for 30min, transferring the reaction solution into a separating funnel, and stirring at room temperatureStanding overnight, removing lower water phase, washing oil phase with distilled water for 3 times, removing water phase to obtain light yellow oily substance, and adding anhydrous Na2SO4Drying, filtering to remove Na2SO，The distillation was carried out under reduced pressure, and fractions (59-60 ℃ C./133.33 Pa) were collected, and the calculated yield was 78%.
Claims (4)
1. A novel method for synthesizing allicin is characterized by comprising the following steps:
adding 28-38 g of sodium thiosulfate and 95ml of distilled water into a reaction container with a magnetic stirring and refluxing device, stirring, and heating to about 35 ℃; after the temperature is stable, adding 1-3.5 g of tetra-n-butyl ammonium iodide serving as a phase transfer catalyst, and uniformly stirring; then 9ml of allyl chloride is transferred into a dropping funnel and slowly dropped into a reaction container, the reaction temperature is controlled to be about 5O-60 ℃ for reflux, and after reaction for 1.5-2.5 h, the mixture is cooled to room temperature; after the temperature is reduced to room temperature, 10 mL1.8mol/L sodium sulfide solution is dripped into the reaction liquid, the reaction liquid is stirred for 30min at room temperature, the reaction liquid is transferred into a separating funnel, the reaction liquid is kept stand for 12 h, the lower-layer water phase is discarded, the oil phase is washed for 3 times by distilled water, the water phase is separated to obtain light yellow oily matter, the light yellow oily matter is dried by anhydrous sodium sulfate, and the sodium sulfate is filtered out; carrying out reduced pressure distillation at an operating pressure of 133.33Pa, and collecting the fraction at 59-60 ℃.
2. The novel process for the synthesis of allicin according to claim 1, characterized in that it comprises the following steps:
adding 36g of sodium thiosulfate and 95ml of distilled water into a reaction vessel with a magnetic stirring and refluxing device, stirring, and heating to about 35 ℃; after the temperature is stable, adding 2g of tetra-n-butylammonium iodide serving as a phase transfer catalyst, and uniformly stirring;
then 9ml of allyl chloride is transferred into a dropping funnel and slowly dropped into a reaction container, the reaction temperature is controlled to be about 50 ℃ for reflux, and after 2 hours of reaction, the mixture is cooled to room temperature; after the temperature is reduced to room temperature, 10 mL1.8mol/L sodium sulfide solution is dripped into the reaction liquid, the reaction liquid is stirred for 30min at room temperature, the reaction liquid is transferred into a separating funnel, the reaction liquid is kept stand for 12 h, the lower-layer water phase is discarded, the oil phase is washed for 3 times by distilled water, the water phase is separated to obtain light yellow oily matter, the light yellow oily matter is dried by anhydrous sodium sulfate, and the sodium sulfate is filtered out; carrying out reduced pressure distillation at an operating pressure of 133.33Pa, and collecting the fraction at 59-60 ℃.
3. The novel process for the synthesis of allicin according to claim 1, characterized in that it comprises the following steps:
adding 28g of sodium thiosulfate and 95ml of distilled water into a reaction vessel with a magnetic stirring and refluxing device, stirring, and heating to about 35 ℃; after the temperature is stable, adding 1g of tetra-n-butyl amine iodide serving as a phase transfer catalyst, and uniformly stirring; then 9ml of allyl chloride is transferred into a dropping funnel and slowly dropped into a reaction container, the reaction temperature is controlled to be about 55 ℃ for reflux, and after reaction for 1.5h, the mixture is cooled to room temperature; after the temperature is reduced to room temperature, 10 mL1.8mol/L sodium sulfide solution is dripped into the reaction liquid, the reaction liquid is stirred for 30min at room temperature, the reaction liquid is transferred into a separating funnel, the reaction liquid is kept stand for 12 h, the lower-layer water phase is discarded, the oil phase is washed for 3 times by distilled water, the water phase is separated to obtain light yellow oily matter, the light yellow oily matter is dried by anhydrous sodium sulfate, and the sodium sulfate is filtered out; carrying out reduced pressure distillation at an operating pressure of 133.33Pa, and collecting the fraction at 59-60 ℃.
4. The novel process for the synthesis of allicin according to claim 1, characterized in that it comprises the following steps:
adding 38g of sodium thiosulfate and 95ml of distilled water into a reaction vessel with a magnetic stirring and refluxing device, stirring, and heating to about 35 ℃; after the temperature is stable, adding 3.5g of tetra-n-butylammonium iodide serving as a phase transfer catalyst, and uniformly stirring; then 9ml of allyl chloride is transferred into a dropping funnel and slowly dropped into a reaction container, the reaction temperature is controlled to be about 60 ℃ for reflux, and after 2.5 hours of reaction, the mixture is cooled to room temperature; after the temperature is reduced to room temperature, 10 mL1.8mol/L sodium sulfide solution is dripped into the reaction liquid, the reaction liquid is stirred for 30min at room temperature, the reaction liquid is transferred into a separating funnel, the reaction liquid is kept stand for 12 h, the lower-layer water phase is discarded, the oil phase is washed for 3 times by distilled water, the water phase is separated to obtain light yellow oily matter, the light yellow oily matter is dried by anhydrous sodium sulfate, and the sodium sulfate is filtered out; carrying out reduced pressure distillation at an operating pressure of 133.33Pa, and collecting the fraction at 59-60 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116162049A (en) * | 2023-02-21 | 2023-05-26 | 石河子大学 | Diallyl trisulfide and preparation method thereof |
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| CN101337917A (en) * | 2008-08-08 | 2009-01-07 | 淮阴工学院 | Method for catalytic synthesis of garlic oil of different combinations by phase-transfer method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101337917A (en) * | 2008-08-08 | 2009-01-07 | 淮阴工学院 | Method for catalytic synthesis of garlic oil of different combinations by phase-transfer method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116162049A (en) * | 2023-02-21 | 2023-05-26 | 石河子大学 | Diallyl trisulfide and preparation method thereof |
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Application publication date: 20200505 |