CN1097748A - A kind of preparation method of difurfuryl dithioether - Google Patents
A kind of preparation method of difurfuryl dithioether Download PDFInfo
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- CN1097748A CN1097748A CN 94100588 CN94100588A CN1097748A CN 1097748 A CN1097748 A CN 1097748A CN 94100588 CN94100588 CN 94100588 CN 94100588 A CN94100588 A CN 94100588A CN 1097748 A CN1097748 A CN 1097748A
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- China
- Prior art keywords
- dmso
- dimethyl sulfoxide
- difurfuryl
- difurfuryl dithioether
- preparation
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Abstract
The invention provides a kind of improved method for preparing difurfuryl dithioether.The method comprising the steps of: make furfurylmercaptan and dimethyl sulfoxide (DMSO) reaction obtain difurfuryl dithioether to reflux temperature for 10 ℃ at normal pressure, the molar ratio of furfurylmercaptan and methyl-sulphoxide is that 1: 0.5～1: 10 this disulfide has nutty, coffee perfume (or spice) and meat perfume (or spice), can be used for various food flavor(ing)s.
Description
The present invention relates to a kind of preparation method of difurfuryl dithioether.
Difurfuryl dithioether has nutty, coffee perfume (or spice) and meat perfume (or spice), can be used for allocating various food flavours, the report consumption in food such as soft drink, ice-creams, iced food, candy, bake, jelly and pudding, chewing gum, food flavouring, meat, gravy, soup class, milk, milk-product is 3.0ppm.
Existing is that the available following reaction formula of method [HenryGilman etc., J.Am.Chem.Soc., 52,2141 (1930)] of feedstock production difurfuryl dithioether is represented with furfural and Sodium sulfhydrate:
The furfural difurfuryl dithioether
Its main process is that at first logical exsiccant hydrogen sulfide in the furfural that is cooling off with the cryosel bath, 95% ethanol, sodium sulphite mixture makes then under the mixture room temperature and spends the night.Tell undissolved sodium sulphite, liquid return 1 hour steams and removes most of ethanol, and resistates is poured in the water, uses extracted with diethyl ether, and ether layer anhydrous sodium sulfate drying steams and remove ether, and underpressure distillation gets two chaff disulfides.
The subject matter that aforesaid method exists is complicated operation, long reaction time.
The purpose of this invention is to provide a kind of improved method for preparing difurfuryl dithioether, this method is easy and simple to handle, and the reaction times is short.
The present invention relates to the preparation method of the difurfuryl dithioether of formula (I):
It is characterized in that with furfurylmercaptan and dimethyl sulfoxide (DMSO) be the feedstock production difurfuryl dithioether, dimethyl sulfoxide (DMSO) is made oxygenant in reaction.
Preparation method of the present invention can represent with following reaction formula:
Furfurylmercaptan dimethyl sulfoxide (DMSO) difurfuryl dithioether
Its main process is, with the mixture of furfurylmercaptan and dimethyl sulfoxide (DMSO) normal pressure, 10 ℃ to stirring between the reflux temperature 0.5～10 hour, after reaction finished, normal pressure steamed and removes dimethyl sulfide, the water that generates in the reaction, underpressure distillation obtains difurfuryl disulfide, productive rate 83.0%.
The molar ratio of furfurylmercaptan and dimethyl sulfoxide (DMSO) is 1: 0.5～1: 10 among the preparation method of the present invention.
The resulting difurfuryl dithioether of the present invention has confirmed its structure through element sulphur analysis, Infrared spectroscopy, proton nuclear magnetic resonance analysis.Analytical results is as follows:
Element sulphur is analyzed: calculated value: 28.33%, and measured value: 28.28%.
Infrared spectroscopy (liquid film):
Absorption peak wave number (cm
-1) explain
The C-H stretching vibration of 3125 furan nucleuss
The C=C stretching vibration of 1590,1500,1400 furan nucleuss
The rocking vibration of 860 furan nucleuss
The C-H out-of-plane deformation vibration of 735 furan nucleuss
Proton magnetic resonance (PMR) (CDCl
3): 7.36 (bimodal, 2 protons), 6.30ppm (four peaks, 2 protons), 6.20ppm (bimodal, 2 protons), 3.65ppm (unimodal, 4 protons)
Major advantage of the present invention is to operate very easyly, and the reaction times shortens greatly, is 0.5～10 hour.
Embodiment 1
In the there-necked flask that has reflux exchanger, electric mixer and thermometer, add 115 gram furfurylmercaptans and 100 gram dimethyl sulfoxide (DMSO), stirred 10 hours under the room temperature, normal pressure steams and removes dimethyl sulfide and water and the unreacted dimethyl sulfoxide (DMSO) that generates, the resistates underpressure distillation, collecting 112～113 ℃/66.7Pa cut is product, and product is colourless to weak yellow liquid.
Embodiment 2
In the there-necked flask that has reflux exchanger, electric mixer and thermometer, add 710 gram furfurylmercaptans, 4500 gram dimethyl sulfoxide (DMSO), be heated to backflow under stirring, reflux and carry out air distillation after 1.5 hours, steam and remove dimethyl sulfide, water and most of unreacted dimethyl sulfoxide (DMSO), resistates underpressure distillation, collecting 112～113 ℃/66.7Pa cut is product, and product is colourless to weak yellow liquid.
Embodiment 3
Having reflux exchanger, in the there-necked flask of electric mixer and thermometer, add 400 gram furfurylmercaptans and 800 gram dimethyl sulfoxide (DMSO), be heated to 65 ℃ under stirring, maintain the temperature at 65～70 ℃ of reactions 3.5 hours, normal pressure steams and removes dimethyl sulfide, water and unreacted dimethyl sulfoxide (DMSO), resistates underpressure distillation, collecting 112-113 ℃/66.7Pa cut is product, and product is colourless to weak yellow liquid.
Claims (2)
1. the preparation method of a difurfuryl dithioether is characterized in that with furfurylmercaptan and dimethyl sulfoxide (DMSO) be raw material, and dimethyl sulfoxide (DMSO) is made oxygenant in reaction.
2. the preparation method of a kind of difurfuryl dithioether according to claim 1, the molar ratio that it is characterized in that furfurylmercaptan and dimethyl sulfoxide (DMSO) is 1: 0.5～1: 10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94100588A CN1045599C (en) | 1994-01-27 | 1994-01-27 | Process for preparing difurfuryl dithioether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94100588A CN1045599C (en) | 1994-01-27 | 1994-01-27 | Process for preparing difurfuryl dithioether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1097748A true CN1097748A (en) | 1995-01-25 |
| CN1045599C CN1045599C (en) | 1999-10-13 |
Family
ID=5029735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94100588A Expired - Fee Related CN1045599C (en) | 1994-01-27 | 1994-01-27 | Process for preparing difurfuryl dithioether |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1045599C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI400040B (en) * | 2006-10-13 | 2013-07-01 | Ogawa & Co Ltd | Perfume composition |
| CN103910662A (en) * | 2013-02-26 | 2014-07-09 | 湖北兴发化工集团股份有限公司 | Method for synthesizing and producing dimethyl disulfide from methyl mercaptan and dimethyl sulfoxide |
| CN106316901A (en) * | 2016-08-24 | 2017-01-11 | 安徽金邦医药化工有限公司 | Synthetic production process of dimethyl disulfide |
| CN113717084A (en) * | 2021-09-15 | 2021-11-30 | 云鹏医药集团有限公司 | Synthesis method of 2, 2' -dithiodiethylamine dihydrochloride |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4020175A (en) * | 1969-10-06 | 1977-04-26 | International Flavors & Fragrances Inc. | Certain 3-furyl sulfides |
| US4098910A (en) * | 1975-02-19 | 1978-07-04 | International Flavors & Fragrances Inc. | Flavoring with certain 3-furyl alkyl disulfides |
| US4092334A (en) * | 1977-07-28 | 1978-05-30 | International Flavors & Fragrances Inc. | 5-Acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones |
-
1994
- 1994-01-27 CN CN94100588A patent/CN1045599C/en not_active Expired - Fee Related
Cited By (5)
| 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 |
| CN103910662A (en) * | 2013-02-26 | 2014-07-09 | 湖北兴发化工集团股份有限公司 | Method for synthesizing and producing dimethyl disulfide from methyl mercaptan and dimethyl sulfoxide |
| CN106316901A (en) * | 2016-08-24 | 2017-01-11 | 安徽金邦医药化工有限公司 | Synthetic production process of dimethyl disulfide |
| CN113717084A (en) * | 2021-09-15 | 2021-11-30 | 云鹏医药集团有限公司 | Synthesis method of 2, 2' -dithiodiethylamine dihydrochloride |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1045599C (en) | 1999-10-13 |
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Owner name: BEIJING TECHNOLOGY AND BUSINESS UNIEERSITY Free format text: FORMER NAME OR ADDRESS: BEIJING LIGHT INDUSTRIAL COLLEGE |
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Patentee after: Beijing Technology and Business University Patentee before: Beijing Light Industry College |
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Granted publication date: 19991013 |