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Preparing method for 3-e Menthyloxy -1,2-propanediol

A technology of propylene glycol and oxypropane, which is applied in the preparation of ethers from alkylene oxides, the preparation of organic compounds, and the preparation of ethers by dehydration of hydroxyl-containing compounds, etc., can solve the problems of not being equal, and achieve a better refreshing effect

Inactive Publication Date: 2002-12-04
TAKASAGO INTERNATIONAL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the case of this method, it is necessary to heat the reaction mixture at a high temperature of 100-230° C., especially 150-200° C., in the presence of a salt formed of a strong base compound and a weak acid compound, so that the glycidyl ether hydrolyzate The contained organohalogens decompose, therefore it is not an effective method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Synthesis of 1-Chloro-3-l-oxy-2-propanol

[0115] (1) In a nitrogen atmosphere, 136.7 g (0.8763 mol) of l-menth alcohol (Takasago International Corporation) and 295 ml of n-heptane were charged into a reaction flask (500 ml capacity) and dissolved at room temperature. Then, 3.5 grams (26.88 milliliters) of anhydrous aluminum chloride were added therein, stirred to dissolve it, and the solution was heated to 70° C., and 61 grams (0.6572 moles) of epichlorohydrin was added dropwise to the solution at the same temperature, and the solution was added dropwise. Add time is 2 hours. After completion of the dropwise addition, the reaction was carried out at the same temperature for 2 hours. After this time, the reaction mixture was cooled to room temperature.

[0116] (2) The reaction mixture obtained in (1) was washed with water and then with 10% aqueous sodium carbonate solution, and an oil was obtained by evaporating n-heptane. By distilling this oil under reduced press...

Embodiment 2

[0123] Synthesis of 1-Acetoxy-3-l-oxy-2-propanol

[0124] (1) In a nitrogen atmosphere, 20 grams of 1-chloro-3-l-menthoxyl-2-propanol (chemical purity 97.86%, 78.78 mmol), 7.13 grams (86.92 mmol) mol) of anhydrous sodium acetate and 0.51 g (1.582 mmol) of tetrabutylammonium bromide were added to a reaction flask (100 ml capacity), and then reacted at 150-160° C. for 4 hours. Thereafter, the reaction mixture was cooled to 50°C or lower.

[0125] (2) The reaction mixture prepared in (1) was mixed with 30 ml of water and 50 ml of heptane for separation, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was recovered to obtain an oily substance. Partially purified 1-acetoxy-3-l-menthoxy-2-propanol obtained by distillation of this oil under reduced pressure at a boiling point of 111-120°C / 25 Pa (0.19 mmHg) . When analyzed by gas chromatography, the product composition consisted of 5.53% by mass of 3-l-menthoxyl-1,2-p...

Embodiment 3

[0133] Synthesis of 1-formyloxy-3-l-oxy-2-propanol

[0134] The reaction was carried out under the same conditions as in Example 2, except that anhydrous sodium formate was used instead of anhydrous sodium acetate to obtain 1-formyloxy-3-l-menthoxyl-2-propane with a yield of 60.9% alcohol.

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Abstract

Process for safe and efficient manufacture of high-purity 3-е-oxy-1,2-propanediol and intermediates for this process. As shown in the following reaction formula, the production method of 3-е-oxyl-1,2-propanediol represented by chemical formula (IV) is: make е-alcohol and general formula (I) in a solvent with Lewis acid The 1,2-epoxy-3-halopropane (wherein X represents a halogen atom) is added to produce 1-halogen-3-е-oxyl-2 represented by the general formula (II) - propanol, make this first intermediate react with the alkali metal salt of aliphatic carboxylic acid containing 1-5 carbon atoms to make 1-acyloxy-2-substituting group-3 represented by general formula (III) -е-oxypropane, and then hydrolyze this second intermediate.

Description

technical field [0001] The present invention relates to a preparation method of 3-l-menthoxy-1,2-propanediol and 1-acyloxy-2-substituent-3-l-menthoxy propane and a preparation method thereof, 3-l-menthoxy Base-1,2-propanediol is used as cooling agent (cool-feeling) or refreshing agent (refreshment improving agent), 1-acyloxy-2-substituent-3-l-menthoxypropane is used to make 3-l -Intermediate in the case of oxy-1,2-propanediol. According to the present invention, high-purity 3-l-menthoxyl-1,2-propanediol can be obtained in high yield and used as a synthetic intermediate of 3-l-menthoxyl-1,2-propanediol through safe and simple operation 1-acyloxy-2-substituent-3-l-menthoxypropane. [0002] In addition, according to the present invention, high optical purity (2S)-3-l-menthoxy-1,2-propanediol with better refreshing feeling and controlled configuration of 2-position of propane moiety can be obtained. Background technique [0003] 3-l-menthoxy-1,2-propanediol is a known compou...

Claims

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Application Information

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IPC IPC(8): C07C41/09C07B53/00C07B61/00C07C41/03C07C41/26C07C43/196C07C67/10C07C69/003C07C69/10C07C69/18
CPCC07C41/03C07C41/26C07C67/11C07C41/42C07B2200/07C07C2601/14C07C69/16C07C69/08C07C43/196C07C41/09
Inventor 天野章秋山照善三浦孝志荻原利光
Owner TAKASAGO INTERNATIONAL CORPORATION
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