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Thiogeraniol preparation method

A technology of geranyl mercaptan and absolute ethanol, which is applied in the field of fine chemistry, can solve the problems that the product purity and content cannot meet the production needs, and the product is difficult to purify and difficult to purify, so as to avoid geranyl mercaptan isomers and reduce The effect of purifying difficulty and reducing difficulty

Active Publication Date: 2016-12-21
石家庄和中科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) Using linalool as raw material, thiogeraniol was prepared by rearrangement and hydrolysis. The product obtained by this method has isomers and is extremely difficult to purify;
[0004] (2) Using geranyl bromide as a raw material, the product is obtained by nucleophilic substitution with different nucleophiles. The product obtained by this method is not easy to purify, and the purity and content of the product cannot meet the production needs

Method used

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preparation example Construction

[0055] Following is the synthetic route of the preparation method of described geranyl thiol:

[0056]

[0057] The preparation method of described geranthiol comprises the following synthetic steps:

[0058] step one:

[0059] Add A, CCl to the reaction kettle 4 , Triphenylphosphine in batches, after the addition is complete, heat the system to raise the temperature to 30-76°C, preferably to 50-60°C, and react for 8-12 hours; gas phase mass spectrometry tracking monitoring, raw materials ≤ 1%, Then stop the reaction; the molar ratio of A and triphenylphosphine is 1:1.3~1.4; A and CCl 4 The mass volume ratio is 1g:5~6ml;

[0060] Post-processing:

[0061] (11) Pad diatomaceous earth, filter with suction;

[0062] (12) Dry the filtrate and spin off the solvent, precipitate the solid, filter with suction, and wash the filter cake with petroleum ether;

[0063] (13) Repeat operation (2) until no solid is precipitated;

[0064] (14) get B;

[0065] Step two:

[0066] (...

Embodiment 1

[0076] The preparation method of described geranthiol, it comprises the following steps:

[0077] step one:

[0078] Add 50g of A with a purity of 93wt%, 233ml of CCl in the reactor 4 , add 102.8g triphenylphosphine in batches, after the addition is completed, the temperature of the system is raised to 55°C, and the reaction is carried out for 8h;

[0079] Gas phase mass spectrometry tracking monitoring, if the raw material is less than 1%, stop the reaction;

[0080] Post-processing:

[0081] (1) Cushion diatomaceous earth, filter with suction;

[0082] (2) Dry the filtrate and spin off the solvent, precipitate the solid, filter with suction, and wash the filter cake with petroleum ether;

[0083] (3) Repeat operation (2) until no solid is precipitated;

[0084] (4) 56.0 g of solid B was obtained, the purity of gas phase mass spectrometry was 80.0%, and the yield was 86.0%;

[0085] Step two:

[0086] Add 56.0g of solid B and 224ml of absolute ethanol to the reaction k...

Embodiment 2

[0096] The preparation method of described geranthiol, it comprises the following steps:

[0097] step one:

[0098] Add 50g of A with a purity of 93wt% and 279ml of CCl in the reactor 4 , add 110.7g triphenylphosphine in batches, after the addition is completed, the temperature of the system is raised to 60°C, and the reaction is carried out for 12 hours;

[0099] Gas phase mass spectrometry tracking monitoring, if the raw material is less than 1%, stop the reaction;

[0100] Post-processing:

[0101] (1) Cushion diatomaceous earth, filter with suction;

[0102] (2) Dry the filtrate and spin off the solvent, precipitate the solid, filter with suction, and wash the filter cake with petroleum ether;

[0103] (3) Repeat operation (2) until no solid is precipitated;

[0104] (4) 55.7g of solid B was obtained, the purity of gas phase mass spectrometry was 79.6%, and the yield was 85.1%;

[0105] Step two:

[0106] Add 55.7g of solid B and 222ml of absolute ethanol to the re...

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Abstract

The invention relates to the field of fine chemistry, and concretely relates to a thiogeraniol preparation method. The method comprises the following steps: carrying out a reaction on a raw material thiogeraniol with triphenyl phosphine in a solvent carbon tetrachloride, carrying out a reaction on the above obtained reaction product 1 with thiourea in a solvent anhydrous ethanol, carrying out a reaction on the above obtained reaction product 2 and p-toluenesulfonic acid to form a salt, and decomposing the salt to obtain a final product. The method has the advantages of avoiding of generation of isomers due to prevention of high-temperature distillation purification in a key purification step, easiness in obtaining of the raw material, low cost, short synthesis short, easiness in realization of reaction conditions, convenient and easy purification process, high yield, and realization of obtaining of highly-pure thiogeraniol.

Description

technical field [0001] The invention relates to the field of fine chemistry, in particular to a preparation method of geranthiol. Background technique [0002] Mercaptan spices are a very important class of sulfur-containing spices, and they are also important raw materials for the synthesis of other sulfur-containing spices. Thiogeraniol, as a thiol spice, has typical green aroma characteristics, and can exhibit a strong characteristic aroma in a solution with a concentration of 0.1% or less; it has a berry taste, so it can be used in food As well as beverages, it can also be applied to solid and liquid detergents, synthetic cleaning agents, aerosols and other products; it is reported that w=0.05% to 0.8% of thiogeraniol is added to the easily available black strawberry fragrance , you can get expensive Cassis fruity. However, thiogeraniol does not occur in nature. The synthesis of thiogeraniol currently reported is relatively small, mainly including: [0003] (1) Using...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/06C07C321/08
CPCC07C17/16C07C303/32C07C319/06C07C319/14C07C321/08C07C21/04C07C323/25C07C309/30
Inventor 郭军永张乱青
Owner 石家庄和中科技有限公司
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