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Synthetic method of racemic menthol and derivatives thereof

A synthesis method and menthol technology are applied in the synthesis field of racemic menthol and derivatives thereof, can solve the problems of high equipment requirements, harsh operating conditions, and cannot reuse hydrocarbon by-products, etc., and achieve a green process and a simple process. Effect

Active Publication Date: 2016-01-20
SHANGHAI WANXIANG FLAVORS & FRAGRANCES
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  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of pure optical active ingredients such as camphene without producing excessive amounts of water or other materials that are harmful when used on food products like chocolate milk powder.

Problems solved by technology

This patented technical problem addressed in these documents relates to improving methods for producing opioldal (rac)-magnesquid) type chemical compositions called menthanols, including α-,β-,γ-(R), delta-4'-substituted tetrahydroxy-1HMgLcα-) naptha-3asteroids, where each molecular structure consists essentially of two atoms from different positions. These structures have been found useful in various applications like cosmeceuticals and food products.

Method used

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  • Synthetic method of racemic menthol and derivatives thereof
  • Synthetic method of racemic menthol and derivatives thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0022] 25g of chlorobenzene was heated to 125°C, and a mixture of 7.6g of citronellol and 7g of di-tert-butyl peroxide was added dropwise under stirring, the addition was completed in 4 hours, and the reaction was continued at 125°C for 14 hours. Gas chromatography detection showed that the conversion rate of citronellol was 57.1%, and the ratio of racemic menthol / neomenthol / isomenthol / menthone / isopulegol was 12.93:1.65:5.31:12.03:3.85. The ratio of menthone to isomenthone is 7.66:4.37. The total selectivity of racemic menthol and its isomers was 34.83%; the selectivity of menthone was 21.64%. The selectivity of isopulegol was 6.74%.

Embodiment 2

[0024] 50g of diphenyl ether, heated to 160°C, added dropwise a mixture of 13g of citronellol, 10g of di-tert-butyl peroxide and 4g of tert-butyl hydroperoxide (70% aqueous solution) under stirring, and the addition was completed in 2 hours. The reaction was continued at 160°C for 12 hours. Gas chromatography detection showed that the conversion rate of citronellol was 81.9%, and the ratio of menthol / neomenthol / isomenthol / menthone / isopulegol was 9.54:2.71:2.25:3.16:19.18. The total selectivity of racemic menthol and its isomers was 17.7%; the selectivity of isopulegol was 23.4%.

Embodiment 3

[0026] 10g of n-decane was heated to 140°C, and a mixture of 3.2g of citronellol and 3g of di-tert-butyl peroxide was added dropwise with stirring, and the addition was completed in 3 hours, and the reaction was continued at 140°C for 8 hours. Gas chromatography detection showed that the conversion rate of citronellol was 68.3%, and the ratio of racemic menthol / neomenthol / isomenthol / menthone / isopulegol was 17.4:3.92:7.83:10.53:2.85. The ratio of menthone to isomenthone is 6.87:3.66. The total selectivity of racemic menthol and its isomers was 42.68%; the selectivity of menthone was 15.4%. The selectivity of isopulegol was 4.17%.

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Abstract

The invention discloses a synthetic method of racemic menthol and derivatives thereof. The synthetic method is characterized by comprising the following steps of adopting citronellol as raw materials, and carrying out intramolecular free radical addition reaction in a solvent at a certain temperature under the action of a peroxide free radical initiator to obtain the racemic menthol; meanwhile, obtaining a certain amount of isomer neomenthol, isomenthol, derivative menthone and isopulegol of the racemic menthol. Compared with the prior art, the synthetic method of the racemic menthol and the derivatives thereof has the following advantages that (1) no waste water is produced during a reaction process, and the technology is simple and green; (2) according to the method provided by the invention, the racemic menthol, and the isomer neomenthol, the isomenthol, the menthone and the isopulegol of the racemic menthol can be produced at the same time.

Description

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Claims

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Application Information

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Owner SHANGHAI WANXIANG FLAVORS & FRAGRANCES
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