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Manufacture method of 3-menthoxy propanol and cooling agent composition

A kind of technology of mentholoxy propanol and mentholoxy, applied in the field of manufacture of 3-menthoxy propanol, can solve the problems of complex cooling sensation presentation mechanism and the like, and achieve the effects of excellent cooling sensation and high yield

Active Publication Date: 2016-01-20
上海高砂·鉴臣香料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] On the other hand, the mechanism for expressing the cool feeling is complicated, and it is known that the effect of enhancing the cool feeling is produced by combining multiple groups of compounds having a cool feeling. Therefore, a method for easily producing a combination that exhibits a strong cool feeling is expected.

Method used

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  • Manufacture method of 3-menthoxy propanol and cooling agent composition
  • Manufacture method of 3-menthoxy propanol and cooling agent composition
  • Manufacture method of 3-menthoxy propanol and cooling agent composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0066] Next, the present invention will be described in further detail through examples, but the present invention is not limited to these examples.

[0067] In addition, the product measurement in the synthesis example and the Example was carried out using the following apparatuses.

[0068] NMR: DRX500 (manufactured by Bruker)

[0069] GC / MS: GCMS-QP2010 (manufactured by Shimadzu Corporation)

[0070] Chromatographic column: RTX-1 (length 30m×inner diameter 0.25mm, liquid film thickness 0.25μm)

[0071] GC purity: GC-14A (manufactured by Shimadzu Corporation)

[0072] Column: Cromatpack CR-4A (manufactured by Shimadzu Corporation)

[0073] Capillary column DB-1 (length 30m x inner diameter 0.25mm, liquid phase film thickness 0.25μm)

[0074] Injection temperature 250°C, detection temperature 250°C

[0075] 100°C-10°C / min-300°C (5 minutes)

[0076] (Example 1) Manufactured by Raney cobalt catalyst

[0077] [Chem 3]

[0078]

[0079] Under nitrogen flow, add 3-L-men...

Embodiment 3～5）

[0101] [chemical 5]

[0102]

[0103] Change the catalyst and reaction conditions in Example 2 to carry out the hydrogenation of 3-L-menthoxy-1,2-propylene oxide (2.1g, 0.01mol) to synthesize 3-L-menthoxy-1-propanol and 1-L-Menthaoxy-2-propanol.

[0104] The results are shown in Table 1. In the table, wt% is relative to the amount ratio of 3-L-menthoxy-1,2-propylene oxide catalyst. mL is the amount of solvent used. Conversion rate and production weight ratio were measured by GC. (A) in the production weight ratio represents 3-menthoxy-1-propanol, and (B) represents 1-menthoxy-2-propanol.

[0105] [Table 1]

[0106]

Embodiment 6）

[0107] (Example 6) Sensory comparative evaluation of 3-L-menthoxyl-1-propanol, 3-L-menthyloxyl-1-propanol and 1-L-menthyloxyl-2-propanol mixture

[0108] The 3-L-menthoxyl-1-propanol (1) obtained in Example 1, the 3-L-menthyloxyl-1-propanol obtained in Example 2 and the 1-L-menthyloxyl-2 - The mixture (2) in which the weight ratio of propanol is 93:7, and the 1-L-menthyloxy-2-propanol (3) further obtained in Example 1 were respectively prepared into 50 ppm aqueous solutions.

[0109] Sensory evaluation of 3 kinds of 50ppm aqueous solutions in the oral cavity was carried out by a professional team of 10 people with more than 5 years of experience.

[0110] As a result, all 10 panelists answered (1) and (2) that there was no unpleasant stimulation, etc., and it had excellent refreshing property. In addition, 7 out of 10 panelists answered that (1) 3-L-menthoxy-1-propanol and (2) mixtures containing 1-L-menthoxy-2-propanol have strong cooling properties sense of continuity. In...

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Abstract

Object of the present invention is to provide a coolant composition containing 3-menthol and a method of using 3-menthol-1,2-propylene oxide as a raw material, highly selective and high yield to manufacture 3-menthol oxypropanol. The present invention relates to a cobalt catalyst, ruthenium catalyst or nickel catalyst and other heterogeneous metal catalysts, by 3- menthoxy -1,2-epoxy catalytic hydrogenation reaction, highly selective and high yield method of manufacturing 3-menthoxypropanol; And an excellent coolant composition comprising a mixture of 3-menthol-1-propanol and 1-menthol-2-propanol.

Description

technical field [0001] The present invention relates to a kind of manufacture method of 3-menthoxypropanol, specifically, in the presence of catalyst, preferably heterogeneous metal supported catalyst, 3-menthoxyl-1,2-epoxypropane method of hydrogenation reduction. The 3-menthoxypropanol obtained by the method of the present invention can be used as a cooling agent or the like. Background technique [0002] Known to impart a cooling sensation (cooling sensation) and a refreshing sensation (cooling sensation) to the human epidermis or mucous membranes (especially the oral cavity, nasal cavity, throat, and eyes) (hereinafter, also collectively referred to as "cooling sensation / cooling sensation") There are many kinds of substances. As a representative substance, L-menthol (L-menthol), the main component of peppermint oil, is widely used in products such as chewing gum, toothpaste, and shampoo. However, although L-menthol has a strong cooling / refreshing feeling, its effect c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/26A23L1/226A61K8/34A61Q5/02A61Q11/00A61Q13/00C07B53/00C07B57/00C07C43/196C07B61/00A23L27/20
CPCA23L27/203A23L2/52A61K8/34A61Q5/02A61Q11/00C07C41/26C07C2601/14C07C43/196C07B53/00C07B57/00A61K2800/244A23L27/2052C11B9/0015A23G4/06A23V2002/00A61K8/33C07C41/18
Inventor 田中茂石田贤哉
Owner 上海高砂·鉴臣香料有限公司
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