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Preparation method of thiogeraniol

A technology for geraniol and geraniol, which is applied in the field of preparation of geraniol, can solve problems such as being unsuitable for industrial-scale production, uneconomical methods, and the like, and achieve the effects of good industrialization prospects, reduced production costs, and simple operation.

Inactive Publication Date: 2009-09-23
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] All in all, the existing methods are uneconomical and unsuitable for industrial-scale production.

Method used

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  • Preparation method of thiogeraniol
  • Preparation method of thiogeraniol
  • Preparation method of thiogeraniol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Preparation of Geranyl Chloride

[0032] At room temperature, 90 milliliters of carbon tetrachloride and 15.42 grams (0.1mol) of geraniol were mixed, and 34.09 grams (0.13mol) of triphenylphosphine were added in four portions within 30 minutes under stirring, and then heated to the reflux of carbon tetrachloride. The temperature was refluxed at 66° C. for 1 hour, and then the reaction system was lowered to room temperature. Add 100 ml of petroleum ether (specification: 30-60 degrees), and continue stirring for 10 minutes. The resulting precipitate was filtered, washed with a small amount of petroleum ether (specification: 30-60 degrees), the filtrate was rotary evaporated to remove the low boiling point solvent, and the residue was rectified under reduced pressure to obtain 6.29 g (37%) of geranyl chloride. The chemical purity measured by gas chromatography was >93%.

[0033] (2) Preparation of geranyl thiol from geranyl chloride

[0034] 22 g (0.128 mol) of gera...

Embodiment 2

[0036] (1) Preparation of Geranyl Bromide

[0037] At room temperature, 36.04 grams (0.11mol) of carbon tetrabromide and 15.42 grams (0.1mol) of geraniol were added to 200 milliliters of dry tetrahydrofuran, and 34.09 grams (0.13mol) of triphenylphosphine were added in four portions within 30 minutes under stirring. Then the reaction system was lowered to room temperature, and after stirring for 1 hour, 400 ml of petroleum ether (specification: 30-60 degrees) was added, and stirring was continued for 10 minutes. The resulting precipitate was filtered, washed with a small amount of petroleum ether (specification: 30-60 degrees), the filtrate was rotary evaporated to remove the low boiling point solvent, and the residue was rectified under reduced pressure to obtain 7.13 g (33%) of geranyl bromide. The chemical purity was >94% as determined by gas chromatography.

[0038] (2) Starting from geranyl bromide to prepare geranyl thiol

[0039] 21.6 g (0.1 mol) of geranyl bromide, 7...

Embodiment 3

[0041] (1) Amplified preparation of geranyl chloride

[0042] At room temperature, 1800 milliliters of carbon tetrachloride and 308.4 grams (2mol) of geraniol were mixed, and 681.8 grams (2.6mol) of triphenylphosphine were added in four portions within 30 minutes under stirring, and then heated to the reflux temperature of carbon tetrachloride Reflux reaction at 66° C. for 1 hour, and then lower the reaction system to room temperature. 2000 ml of n-hexane was added, and stirring was continued for 10 minutes. The resulting precipitate was filtered, washed with a small amount of n-hexane, the filtrate was rotary evaporated to remove the low boiling point solvent, and the residue was rectified under reduced pressure to obtain 179 g (52%) of geranyl chloride. The chemical purity measured by gas chromatography was >93%.

[0043] (2) Scale up the preparation of geranyl thiol from geranyl chloride

[0044] 220 g (1.28 mol) of geranyl chloride, 98 g (1.28 mol) of thiourea and 1000 ml...

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Abstract

The invention relates to a preparation method of thiogeraniol, which comprises the steps as follows: geraniol is used as raw material, and carbon tetrachloride and triphenylphosphine or carbon tetrabromide and triphenylphosphine are used as halogenating agents; the reaction temperature is respectively set at reflow temperature of 66 DEG C and room temperature; the reaction pressure is set as normal pressure and the reaction time is 1-2 hours; after treatment of the reaction system, geranylchlorine or geranylbromine is obtained by rectification and purification; reflow reaction is carried out on the obtained product and thiourea in 95% ethanol; alkali is then added for hydrolyzation; and acid is finally added for neutralization, thereby obtaining thiogeraniol by decompression and rectification after treatment of extracted solution. The method uses geraniol, which can be abundantly produced, as raw material to synthesize thiogeraniol, which has the advantages of easily available raw material, high product yield and low production cost.

Description

technical field [0001] The present invention relates to take geraniol as raw material, the method for preparing geranyl thiol by two-step reaction, particularly relate to in halogenation reaction process with carbon tetrachloride and triphenylphosphine or carbon tetrabromide and triphenylphosphine as Halogenation reagent, S-geranyl isosulfate is generated from geranyl halide and thiourea during the preparation of thiols. Background technique [0002] Mercaptan spices are the most important class of sulfur-containing spices. They are a new type of spices developed after the 1970s. Most of them are trace aroma components of food, and they are also important raw materials or intermediates for the synthesis of other sulfur-containing spices. body. As a mercaptan, geraniol does not exist in nature, it has the taste of berries such as grapes, so it can be used in food, as well as in beverages or as a scent for the manufacture of odor components, such as perfume, and can also be a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C321/08C07C319/02
Inventor 刘旭东刘泓希周跃范慧俐
Owner UNIV OF SCI & TECH BEIJING
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