Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Process for producing 2-(l-menthoxy)ethanol compound

A technology of menthyl oxygen and compounds, which is applied in the field of preparation of 2-ethanol compounds, can solve the problems of not being cheap, cumbersome procedures, and high costs

Inactive Publication Date: 2008-02-06
TAKASAGO INTERNATIONAL CORPORATION
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among the above-mentioned compounds, although the (1'R, 2'S, 5'R)-3-L-menthoxyalkan-1-ol compounds described in JP-A-2001-294546 have a good cooling and refreshing feeling effect, but so far cannot be prepared in a simple and inexpensive way
According to JP-A-2001-294546, the compound is prepared by using lithium aluminum hydride to reduce the ether compound obtained from L-menthol and chloroacetic acid, and the procedure is cumbersome and the cost is high

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for producing 2-(l-menthoxy)ethanol compound
  • Process for producing 2-(l-menthoxy)ethanol compound
  • Process for producing 2-(l-menthoxy)ethanol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of 2-(L-menthyloxy)ethanol using anhydrous aluminum chloride

[0036] (1) In a 1000ml four-neck flask, add 100.0g (641mmol) of L-menthol and 42.7g (320mmol) of anhydrous aluminum chloride, replace with nitrogen, add 500ml of toluene while ice-cooling and start stirring. After confirming that the temperature of the reaction liquid had dropped to about 5°C, 57 g of ethylene oxide was added while maintaining the liquid temperature at 5 to 10°C. After the feed was complete, further stirring was carried out at room temperature for 1 hour to complete the reaction.

[0037] (2) Next, the reaction solution was cooled again and washed with 150 ml of 10% hydrochloric acid while keeping the temperature below 20°C. Next, wash with 50 ml of saturated sodium bicarbonate and 100 ml of saturated brine, remove water with sodium sulfate, and recover the solvent under reduced pressure to obtain 123.1 g of crude 2-(L-menthoxy)ethanol. Carry out Vigoreux distillatio...

Embodiment 2

[0045] Example 2: Preparation of 2-(L-menthoxy)ethanol using various Lewis acid catalysts

[0046] With respect to the L-menthol of 1mol, respectively use the Lewis acid catalyst shown in table 2 below 0.2mol, adopt the reaction temperature and the reaction time as shown in table 2, other conditions are the same as embodiment 1, make L-menthol and Ethylene oxide reacts to produce 2-(L-menthoxy)ethanol. The results are shown in Table 2 below, and the conversion, selectivity and yield have the same meanings as in Table 1.

[0047] Table 2

[0048] experiment

Numbering

Catalyst (Reagent)

temperature reflex

(℃)

Reaction time

(hr)

Conversion rates

(%)

selectivity

(%)

Yield

(%)

type

Usage amount 1)

1

Anhydrous AlCl 3

0.2mol

40

2.0

38.8

86.2

33.5

2

ZnCl 2

0.2mol

40

3.0

27.4

91.2

25.0

...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A process by which a 2-(L-menthoxy)ethanol compound which can enable foods or beverages, cigarettes, cosmetics, etc. to give a refreshing cool feeling can be produced from inexpensive materials through a simple step at low cost. The process, which is for producing a 2-(L-menthoxy)ethanol compound represented by the general formula (1) (wherein R represents hydrogen, alkyl, or 1-hydroxyalkyl), comprises reacting L-menthol with a 1,2-epoxyalkane in the presence of a catalyst comprising a Lewis acid.

Description

technical field [0001] The invention relates to a preparation method of 2-(L-menthoxy)ethanol compounds. More specifically, the present invention provides a kind of 2-(L-menthoxy)ethanols with cooling effect and refreshing feeling prepared by simple process steps and at a lower cost compound method. Background technique [0002] It is known that there are many substances that can produce a cooling sensation (cooling sensation) or refreshing sensation (cooling sensation) on human skin and mucous membranes, especially the oral cavity, nasal cavity, throat, and eyes (hereinafter collectively referred to as "cooling and refreshing sensation"). An example of a representative substance is L-menthol, a main component of peppermint oil, which is widely used in chewing gum, toothpaste, shampoo and the like. Although L-menthol has a strong cooling and refreshing feeling, its effect cannot last for a long time, and its use and dosage are often limited due to its strong mint-type arom...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/03C07C43/196C07B53/00C07B61/00
CPCC07C43/196C07C2101/14C07C41/03C07C2601/14C07C41/26
Inventor 足立谦一郎石田贤哉松田洋幸
Owner TAKASAGO INTERNATIONAL CORPORATION
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com