CN1045598C - Process for preparing di (2-methyl-3-furyl) dithioether - Google Patents
Process for preparing di (2-methyl-3-furyl) dithioether Download PDFInfo
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- CN1045598C CN1045598C CN 94100587 CN94100587A CN1045598C CN 1045598 C CN1045598 C CN 1045598C CN 94100587 CN94100587 CN 94100587 CN 94100587 A CN94100587 A CN 94100587A CN 1045598 C CN1045598 C CN 1045598C
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- Prior art keywords
- methyl
- furyl
- dithioether
- dimethyl sulfoxide
- furanthiol
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Abstract
The present invention provides an improved method for preparing di (2-methyl-3-furyl) dithioether. The method comprises the following steps: under the normal pressure and at the temperature of 10 DEG C to the return temperature, 2-methyl-3-furanthiol reacts with dimethyl sulfoxide, which generates di (2-methyl-3-furyl) dithioether, and the material used molar ratio of the 2-methyl-3-furanthiol to the dimethyl sulfoxide is from 1:0.5 to 1:10. The dithioether has the good meat scent and roasted meat scent. The dithioether can be used for various kinds of edible essence and especially for flavoring essence.
Description
The present invention relates to the preparation method of a kind of two (2-methyl-3-furyl) disulfide.
Two (2-methyl-3-furyl) disulfide has the fragrant and barbecue perfume (or spice) of good meat, can be used for allocating various food flavor(ing)s, especially seasoning essence.
Existing is that the available following reaction formula of method (United States Patent (USP) 4020175) of feedstock production two (2-methyl-3-furyl) disulfide is represented with 2-methyl-3-furanthiol:
2-methyl-3-furanthiol two (2-methyl-3-furyl) disulfide
Its main process is, under stirring at room, in the mixture of 2-methyl-3-furanthiol and hexane, blow air filled cavity, make oxygenant, 2-methyl-3-furanthiol is oxidized to two (2-methyl-3-furyl) disulfide with airborne oxygen, 20 hours reaction times, productive rate 60.5%.
The subject matter one that aforesaid method exists is long reaction time, the 2nd, and productive rate is low.
The purpose of this invention is to provide the method for a kind of improved preparation two (2-methyl-3-furyl) disulfide, this method has shortened the reaction times, has improved the productive rate of two (2-methyl-3-furyl) disulfide.
The present invention relates to the preparation method of two (2-methyl-3-furyl) disulfide of formula I:
It is characterized in that with 2-methyl-3-furanthiol being that the method for feedstock production two (2-methyl-3-furyl) disulfide adopts dimethyl sulfoxide (DMSO) to make oxygenant.Preparation method of the present invention can represent with following reaction formula:
2-methyl-3-furanthiol dimethyl sulfoxide (DMSO) two (2-methyl-3-furyl) disulfide
Its main process is, with the mixture of 2-methyl-3-furanthiol 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 and the water that generates in the reaction, and underpressure distillation obtains two (2-methyl-3-furyl) disulfide.
The molar ratio of 2-methyl-3-furanthiol and dimethyl sulfoxide (DMSO) is 1: 0.5～1: 10 among the preparation method of the present invention.
The present invention's resulting two (2-methyl-3-furyl) disulfide 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: 28.39%.
Infrared spectroscopy (liquid film):
Absorption peak wave number (cm
-1) explain
The C-H stretching vibration of 3120 furan nucleuss
The C-H asymmetrical stretching vibration of 2950 methyl
The C=C stretching vibration of 1585,155 furan nucleuss
The asymmetric bending vibration of 1445 methyl
The symmetric curvature vibration of 1385 methyl
The rocking vibration of 890 furan nucleuss
735 2, the C-H out-of-plane deformation vibration of 3-two substituted furans
Proton magnetic resonance (PMR) (CDCl
3): 7.25ppm (bimodal, 2 protons), 6.35ppm (bimodal, 2 protons), 2.10ppm (unimodal, 6 protons)
Major advantage of the present invention has following two aspects:
1. preparation method of the present invention operates very easyly, and the reaction times shortens greatly, is 0.5～10 hour.
2. preparation method of the present invention has improved the productive rate of two (2-methyl-3-furyl) disulfide, reaches 70.2%.
Embodiment 1
In the there-necked flask that has reflux exchanger, electric mixer and thermometer, add 11.5 gram 2-methyl-3-furanthiols and 9.4 gram dimethyl sulfoxide (DMSO), stirred 10 hours under the room temperature, normal pressure steams and removes dimethyl sulfide and water and the most of unreacted dimethyl sulfoxide (DMSO) that generates, the resistates underpressure distillation, collecting 77-78 ℃/40Pa cut is product, and product is a light yellow transparent liquid.
Embodiment 2
In the there-necked flask that has reflux exchanger, electric mixer and thermometer, add 13.0 gram 2-methyl-3-furanthiols, 66.0 gram dimethyl sulfoxide (DMSO), be heated to backflow under stirring, keep refluxing 1 hour, carry out air distillation then, steam and remove dimethyl sulfide, water and most of unreacted dimethyl sulfoxide (DMSO), the resistates underpressure distillation, collecting 77-78 ℃/40Pa cut is product, product is a light yellow transparent liquid.
Embodiment 3
In the there-necked flask that has reflux exchanger, electric mixer and thermometer, add 22.8 gram 2-methyl-3-furanthiols, 40.0 gram dimethyl sulfoxide (DMSO), be heated to 70 ℃ under stirring, maintain the temperature at 70～75 ℃ of reactions 2.5 hours, normal pressure steams and removes dimethyl sulfide, water and unreacted dimethyl sulfoxide (DMSO), the resistates underpressure distillation, collecting 77-78 ℃/40Pa cut is product, product is a light yellow transparent liquid.
Claims (1)
1. the preparation method of one kind two (2-methyl-3-furyl) disulfide is characterized in that with 2-methyl-3-furanthiol be raw material, makees oxygenant with dimethyl sulfoxide (DMSO).The molar ratio of 2-methyl-3-furanthiol and dimethyl sulfoxide (DMSO) is 1: 0.5～1: 10; Temperature of reaction at 10 ℃ between the reflux temperature; Reaction pressure is a normal pressure; 0.5～10 hour reaction times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94100587 CN1045598C (en) | 1994-01-27 | 1994-01-27 | Process for preparing di (2-methyl-3-furyl) dithioether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94100587 CN1045598C (en) | 1994-01-27 | 1994-01-27 | Process for preparing di (2-methyl-3-furyl) dithioether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1097747A CN1097747A (en) | 1995-01-25 |
| CN1045598C true CN1045598C (en) | 1999-10-13 |
Family
ID=5029734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 94100587 Expired - Fee Related CN1045598C (en) | 1994-01-27 | 1994-01-27 | Process for preparing di (2-methyl-3-furyl) dithioether |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1045598C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5173178B2 (en) | 2006-10-13 | 2013-03-27 | 小川香料株式会社 | Fragrance 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 |
-
1994
- 1994-01-27 CN CN 94100587 patent/CN1045598C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1097747A (en) | 1995-01-25 |
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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 |