CN102260240A - Synthesis method of edible flavor 1,2,3,5,6-pentathiepane - Google Patents
Synthesis method of edible flavor 1,2,3,5,6-pentathiepane Download PDFInfo
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- CN102260240A CN102260240A CN2011102252592A CN201110225259A CN102260240A CN 102260240 A CN102260240 A CN 102260240A CN 2011102252592 A CN2011102252592 A CN 2011102252592A CN 201110225259 A CN201110225259 A CN 201110225259A CN 102260240 A CN102260240 A CN 102260240A
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Abstract
The invention relates to a synthesis method of edible flavor 1,2,3,5,6-pentathiepane. The synthesis method comprises the following steps: firstly carrying out sulfanylation: adding sodium tetrathiocarbonate and absolute ethanol into a three-neck reaction flask provided with a stirrer, a constant-pressure dropping funnel and a thermometer, stirring until the sodium tetrathiocarbonate is completely dissolved, dropwisely adding an absolute ethanol solution of diiodomethane at 25 DEG C within 2 hours by using the constant-pressure dropping funnel, and then stirring and reacting at the constant temperature of 25 DEG C for 10 hours; secondly extracting: diluting the above reaction solution with water, then extracting with cyclohexane three times, combining the extract solutions after separating the water layer, and adding anhydrous calcium chloride for drying; and finally distilling to obtain the finished product. Through the synthesis method provided by the invention, edible flavor 1,2,3,5,6-pentathiepane with dense characteristic aroma and good antibacterial activity and biological activity is provided, the process is simple to operate, and the yield is high; and the edible flavor can be used as a flavor to be safely applied in various cooking processes, and is a novel lenthionine.
Description
Technical field
The invention belongs to field of fine chemical, especially a kind of flavouring agent 1,2,3,5, the synthetic method of 6-five sulphur suberane.
Technical background
Current social people are all the more rich and varied to the selection of food, and except the nutritive value of being concerned about them, it is various also very to pay attention to its color, and therefore the demand to flavouring agent increases day by day.
Mushroom is one of internationally recognized health-care vegetable, can improve immune function of human body.1,2,3,5,6-five sulphur suberane are main fragrant compositions of mushroom, are that first that obtain from nature contains the organism of a plurality of sulphur atoms, have strong feature fragrance and good antibacterial activity and biological activity.
At present, existing 1,2,3,5, the preparation method of 6-five sulphur suberane is as follows: with Sodium sulphate anhydrous, 99min, elemental sulfur and carbon disulphide manufacture tetrathio yellow soda ash (productive rate 75%), methylene iodide is added drop-wise in the ethanolic soln of tetrathio yellow soda ash, back flow reaction 10h has obtained 1,2,3,5,6-five sulphur suberane, determine that best extraction solvent is a tetracol phenixin, and operation is simple, the reaction times shortens to 12h from 48h.Traditional synthetic 1,2,3,5, the method severe reaction conditions of 6-five sulphur suberane, it is many that low temperature reaches-78 ℃, operation steps, also need through repeatedly extracting, separate, and long reaction time, yield is low.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art part, provide that a kind of technological operation is simple, yield is high, the flavouring agent of synthesis technique environmental protection 1,2,3,5, the synthetic method of 6-five sulphur suberane.
The present invention realizes that the technical scheme of purpose is as follows:
A kind of flavouring agent 1,2,3,5, the synthetic method of 6-five sulphur suberane, step is as follows:
(1) sulfo-: in three mouthfuls of reaction flasks that agitator, constant pressure funnel, thermometer are housed, add tetrathio yellow soda ash and dehydrated alcohol and be stirred to tetrathio yellow soda ash and dissolve fully, at the ethanol solution that in 2 hours, drips methylene iodide under 25 ℃, drip off 25 ℃ of stirring reactions of back constant temperature 10 hours with constant pressure funnel;
(2) extraction: with above-mentioned reaction solution dilute with water, again with hexanaphthene extraction three times, combining extraction liquid behind the branch water-yielding stratum adds Calcium Chloride Powder Anhydrous and carries out drying;
(3) distillation: dried solution is filtered, and filtrate is poured in the matrass and is distilled, and normal pressure 70-80 ℃ obtains the xanchromatic oily liquids after steaming tetracol phenixin, and behind the crystallisation by cooling, the light yellow solid that obtains having mushroom fragrance is 1,2,3,5,6-five sulphur suberane,
Described proportioning raw materials is as follows:
And described methylene iodide is used anhydrous alcohol solution before dropping, is dissolved into behind the solution to drip again.
Advantage of the present invention and positively effect
1,1 of the present invention's development, 2,3,5,6-five sulphur suberane, have another name called the mushroom essence, it is widely used in jam product, meat product, ready-to-eat, the seasonings meat soup series, and its fragrance is pure, true to nature, strong mellow, voluptuousness is plentiful, mouthfeel good, can cover undesired off taste, and can be high temperature resistant, be that the ideal of canned mushroom, mushroom class sauce, ready-to-eat, seasonings is selected, have vast market prospect.
2, the invention provides a kind of have strong feature fragrance and good anti-microbial activity and bioactive flavouring agent 1,2,3,5,6-five sulphur suberane, technological operation is simple, yield is high, can be used as spices and be used safely in the cooking process such as Fried, fried, cooked, fried, is a kind of novel lenthionine.
3, not only technological operation is simple in the present invention, with toxicity greatly and have than strong and stimulating and narcotic extraction agent tetracol phenixin and change the low hexanaphthene of toxicity into, having avoided operator in the production process to be subjected to the harm of intense stimulus, is a kind of green synthesis process of environmental protection.
Embodiment:
Below in conjunction with embodiment, the present invention is further described, and following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
Embodiment 1:
A kind of flavouring agent 1,2,3,5, the synthetic method of 6-five sulphur suberane, the concrete operations step is as follows:
Proportioning raw materials:
Operation steps:
(1) sulfo-: in three mouthfuls of reaction flasks that agitator, constant pressure funnel, thermometer are housed, add 188g tetrathio yellow soda ash and 400ml dehydrated alcohol and be stirred to tetrathio yellow soda ash and dissolve fully, at the ethanol solution that in 2 hours, drips methylene iodide under 25 ℃, drip off 25 ℃ of stirring reactions of back constant temperature 10 hours with constant pressure funnel;
Treatment process before methylene iodide uses is: in beaker the 188g methylene iodide is dissolved in the 1000ml dehydrated alcohol;
(2) extraction: above-mentioned reaction solution with the dilution of 2000ml water, is extracted three times with hexanaphthene again, and combining extraction liquid behind the branch water-yielding stratum adds an amount of Calcium Chloride Powder Anhydrous and carries out drying;
(3) distillation: dried solution is filtered, and filtrate is poured in the matrass and is distilled, and normal pressure 75-80 ℃ obtains the xanchromatic oily liquids after steaming tetracol phenixin, behind the crystallisation by cooling, the light yellow solid that obtains having mushroom fragrance is 1,2,3,5,6-five sulphur suberane.
Embodiment 2:
A kind of flavouring agent 1,2,3,5, the synthetic method of 6-five sulphur suberane, the concrete operations step is as follows:
Proportioning raw materials:
Operation steps:
(1) sulfo-: in three mouthfuls of reaction flasks that agitator, constant pressure funnel, thermometer are housed, add 190g tetrathio yellow soda ash and 450ml dehydrated alcohol and be stirred to tetrathio yellow soda ash and dissolve fully, at the ethanol solution (in beaker, the 196g methylene iodide being dissolved in advance) that in 2 hours, drips methylene iodide under 25 ℃, drip off 25 ℃ of stirring reactions of back constant temperature 10 hours in the 1100ml dehydrated alcohol with constant pressure funnel.
(2) extraction: above-mentioned reaction solution with the dilution of 2000ml water, is extracted three times with hexanaphthene again, and combining extraction liquid behind the branch water-yielding stratum adds an amount of Calcium Chloride Powder Anhydrous and carries out drying.
(3) distillation: dried solution is filtered, and filtrate is poured in the matrass and is distilled, and normal pressure 74-78 ℃ obtains the xanchromatic oily liquids after steaming tetracol phenixin, behind the crystallisation by cooling, the light yellow solid that obtains having mushroom fragrance is 1,2,3,5,6-five sulphur suberane finished products.
Embodiment 3:
A kind of flavouring agent 1,2,3,5, the synthetic method of 6-five sulphur suberane, the concrete operations step is as follows:
Proportioning raw materials:
Operation steps:
(1) sulfo-: in three mouthfuls of reaction flasks that agitator, constant pressure funnel, thermometer are housed, add 195g tetrathio yellow soda ash and 500ml dehydrated alcohol and be stirred to tetrathio yellow soda ash and dissolve fully, at the ethanol solution (in beaker, the 198g methylene iodide being dissolved in advance) that in 2 hours, drips methylene iodide under 25 ℃, drip off 25 ℃ of stirring reactions of back constant temperature 10 hours in the 1100ml dehydrated alcohol with constant pressure funnel.
(2) extraction: above-mentioned reaction solution with the dilution of 2000ml water, is extracted three times with hexanaphthene again, and combining extraction liquid behind the branch water-yielding stratum adds an amount of Calcium Chloride Powder Anhydrous and carries out drying.
(3) distillation: dried solution is filtered, and filtrate is poured in the matrass and is distilled, and normal pressure 76-80 ℃ obtains the xanchromatic oily liquids after steaming tetracol phenixin, behind the crystallisation by cooling, the light yellow solid that obtains having mushroom fragrance is 1,2,3,5,6-five sulphur suberane finished products.
Claims (2)
1. flavouring agent 1,2,3,5, the synthetic method of 6-five sulphur suberane, it is characterized in that: step is as follows:
(1) sulfo-: in three mouthfuls of reaction flasks that agitator, constant pressure funnel, thermometer are housed, add tetrathio yellow soda ash and dehydrated alcohol and be stirred to tetrathio yellow soda ash and dissolve fully, at the ethanol solution that in 2 hours, drips methylene iodide under 25 ℃, drip off 25 ℃ of stirring reactions of back constant temperature 10 hours with constant pressure funnel;
(2) extraction: with above-mentioned reaction solution dilute with water, again with hexanaphthene extraction three times, combining extraction liquid behind the branch water-yielding stratum adds Calcium Chloride Powder Anhydrous and carries out drying;
(3) distillation: dried solution is filtered, and filtrate is poured in the matrass and is distilled, and normal pressure 70-80 ℃ obtains the xanchromatic oily liquids after steaming tetracol phenixin, and behind the crystallisation by cooling, the light yellow solid that obtains having mushroom fragrance is 1,2,3,5,6-five sulphur suberane,
Described proportioning raw materials is as follows:
2. flavouring agent 1,2,3,5 according to claim 1, the synthetic method of 6-five sulphur suberane is characterized in that: described methylene iodide is used anhydrous alcohol solution before dropping, is dissolved into behind the solution to drip again.
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| CN2011102252592A CN102260240A (en) | 2011-08-08 | 2011-08-08 | Synthesis method of edible flavor 1,2,3,5,6-pentathiepane |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018135417A1 (en) * | 2017-01-23 | 2018-07-26 | 三菱瓦斯化学株式会社 | Method for producing 1,2,3,5,6-pentathiepane |
| CN108456193A (en) * | 2017-02-21 | 2018-08-28 | 三菱瓦斯化学株式会社 | The manufacturing method of five thia cycloheptane of 1,2,3,5,6- |
| WO2019181484A1 (en) * | 2018-03-22 | 2019-09-26 | 三菱瓦斯化学株式会社 | Production method for 1,2,3,5,6-pentathiepane |
-
2011
- 2011-08-08 CN CN2011102252592A patent/CN102260240A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180090901A (en) * | 2017-01-23 | 2018-08-13 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | Production method of 1,2,3,5,6-pentatriene plate |
| CN108633276A (en) * | 2017-01-23 | 2018-10-09 | 三菱瓦斯化学株式会社 | The manufacturing method of five thia cycloheptane of 1,2,3,5,6- |
| KR101942059B1 (en) * | 2017-01-23 | 2019-01-24 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | Production method of 1,2,3,5,6-pentatriene plate |
| CN108633276B (en) * | 2017-01-23 | 2019-05-31 | 三菱瓦斯化学株式会社 | The manufacturing method of five thia cycloheptane of 1,2,3,5,6- |
| WO2018135417A1 (en) * | 2017-01-23 | 2018-07-26 | 三菱瓦斯化学株式会社 | Method for producing 1,2,3,5,6-pentathiepane |
| US10472343B2 (en) | 2017-01-23 | 2019-11-12 | Mitsubishi Gas Chemical Company, Inc. | Method for producing 1,2,3,5,6-pentathiepane |
| CN108456193B (en) * | 2017-02-21 | 2022-04-08 | 三菱瓦斯化学株式会社 | Method for producing 1,2,3,5, 6-pentathiazepan |
| CN108456193A (en) * | 2017-02-21 | 2018-08-28 | 三菱瓦斯化学株式会社 | The manufacturing method of five thia cycloheptane of 1,2,3,5,6- |
| WO2019181484A1 (en) * | 2018-03-22 | 2019-09-26 | 三菱瓦斯化学株式会社 | Production method for 1,2,3,5,6-pentathiepane |
| EP3770156A4 (en) * | 2018-03-22 | 2021-03-31 | Mitsubishi Gas Chemical Company, Inc. | Production method for 1,2,3,5,6-pentathiepane |
| JPWO2019181484A1 (en) * | 2018-03-22 | 2021-04-08 | 三菱瓦斯化学株式会社 | 1,2,3,5,6-Pentachie bread manufacturing method |
| CN111819171A (en) * | 2018-03-22 | 2020-10-23 | 三菱瓦斯化学株式会社 | Method for producing 1,2,3,5, 6-pentathiazepan |
| JP7226430B2 (en) | 2018-03-22 | 2023-02-21 | 三菱瓦斯化学株式会社 | Method for producing 1,2,3,5,6-pentathiepane |
| CN111819171B (en) * | 2018-03-22 | 2023-03-28 | 三菱瓦斯化学株式会社 | 1,2,3,5,6-pentathiazepan manufacturing method |
| US11919877B2 (en) | 2018-03-22 | 2024-03-05 | Mitsubishi Gas Chemical Company, Inc. | Production method for 1,2,3,5,6-pentathiepane |
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Application publication date: 20111130 |