A kind of synthetic method of α-isomethyl ionone

The technology of isomethyl ionone and methyl ionone is applied in the field of synthesizing α-isomethyl ionone fragrance and can solve the problem of low selectivity of α-isomethyl ionone and content of α-isomethyl ionone low production cost, few processing steps, and high selectivity

Active Publication Date: 2020-12-01
SHANDONG NHU PHARMA
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the existing industrial technology, the reaction temperature is low, the amount of catalyst is large, and there are many three wastes. At the same time, the synthesis of α-isomethyl ionone is mainly carried out by adding raw materials, condensation solvents, and condensation catalysts. The crude product is purified by washing, solvent recovery, distillation and other steps; then the crude product, cyclization solvent, and cyclization catalyst are put into the second step of cyclization reaction, and after multiple washings, solvent recovery, rectification and purification, α-isomethyl violet is obtained ketone
The operation is cumbersome, the equipment investment is doubled, the energy consumption is high, the three wastes are more, and the total production cost is high
[0006] The prior art prepares α-isomethyl ionone products, but there are also low yields and other isotropes such as α-n-methyl ionone, β-isomethyl ionone, and β-n-methyl ionone in the prepared product. High isomer content, low content of α-isomethyl ionone, i.e. low selectivity for α-isomethyl ionone

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
  • A kind of synthetic method of α-isomethyl ionone
  • A kind of synthetic method of α-isomethyl ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 A kind of synthetic method of α-isomethyl ionone

[0031] Include the following steps:

[0032] (1) Add 228.0g of citral, 432.5g of methyl ethyl ketone and 648.5g of solvent methanol into the autoclave for mixing under the protection of nitrogen, add 1.50g of catalyst 1 (pyrrolidine) into the autoclave, replace with nitrogen, and control the reaction temperature at 50°C, heat preservation for 25 hours to detect 0.45% citral residue, and obtain pseudo-methylionone;

[0033] (2) Add 6.32g of catalyst 2 (trifluoromethanesulfonic acid) under the protection of nitrogen, stir evenly and raise the temperature to 110°C, continue the reaction, keep it warm for 5h, and detect that the content of pseudomethyl ionone is 0.3%. After the reaction is completed, add Sodium carbonate was neutralized, solvent 647.5g was reclaimed, butanone 321g was reclaimed to obtain the crude product, and then 304.7g of α-isomethylionone pure product was rectified at an absolute pressure ...

Embodiment 2

[0034] Embodiment 2 A kind of synthetic method of α-isomethyl ionone

[0035] Include the following steps:

[0036] (1) Add citral 228.0g, butanone 216.2g and solvent polyethylene glycol 200:600.6g into the autoclave for mixing under nitrogen protection, add catalyst 1 (potassium carbonate) 0.21g into the autoclave, and replace with nitrogen , control the reaction temperature at 40°C, keep the temperature for 40 hours to detect 0.48% of the residual citral, and obtain pseudo-methylionone;

[0037] (2) Add 0.78g of catalyst 2 (p-toluenesulfonic acid) under the protection of nitrogen and stir evenly, then raise the temperature to 130°C, continue the reaction, keep it warm for 10h, and detect that the content of pseudomethylionone is 0.35%, and the reaction is over , add sodium carbonate to neutralize; reclaim 600g of solvent, reclaim butanone 103.7g, obtain crude product, then rectify 302.1g of α-isomethyl ionone pure product at absolute pressure 100pa, in terms of citral, the ...

Embodiment 3

[0038] Embodiment 3 A kind of synthetic method of α-isomethyl ionone

[0039] Include the following steps:

[0040] (1) Add 228.2g of citral, 648.1g of methyl ethyl ketone and 810.4g of solvent water into the autoclave for mixing under the protection of nitrogen, add 4.05g of catalyst 1 (sodium methoxide) into the autoclave, replace with nitrogen, and control the reaction temperature at -10°C, heat preservation for 40 hours to detect 0.42% citral residue, and obtain pseudo-methylionone;

[0041] (2) Add 17.10 g of catalyst 2 (trifluoroacetic acid) under the protection of nitrogen and stir evenly, then raise the temperature to 80°C, continue the reaction, keep it warm for 8 hours, and detect that the content of pseudomethyl ionone is 0.52%. After the reaction is completed, add carbonic acid Sodium neutralization; recovery of solvent 809.7g, recovery of methyl ethyl ketone 535.74g, to obtain the crude product, and then rectifying 295.6g of pure α-isomethyl ionone at an absolute...

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

The invention provides a synthesizing method of alpha-iso-methyl violet ketone. The method includes the steps of preparing false methyl violet ketone, and preparing alpha-iso-methyl violet ketone. When false methyl violet ketone is prepared, the reaction temperature is minus 10 DEG C to 85 DEG C; when alpha-iso-methyl violet ketone is prepared, the reaction temperature is 80-130 DEG C. In the method, by inputting different catalysts in different steps, alpha-iso-methyl violet ketone is efficiently synthesized through a one-pot method, the reaction catalyst consumption is small, three wastes are few, yield is high, and selectivity is good. The selectivity of alpha-iso-methyl violet ketone in the obtained finished product reaches 95.0% or above, the molar yield reaches 95.0% according to citral, and the industrial and green synthesis of alpha-iso-methyl violet ketone is facilitated.

Description

technical field [0001] The invention relates to a method for synthesizing perfume, in particular to the synthesis of alpha-isomethyl ionone perfume. Background technique [0002] Methylionone is a kind of spice with a unique aroma. Its aroma is sweet, including the aroma of violets, the elegant sweetness of iris, and the smell of acacia, so it is widely used in spice blending. [0003] Methyl ionone is a colorless to pale yellow liquid composed of six isomers: α-isomethyl ionone, α-n-methyl ionone, β-isomethyl ionone, β- N-methyl ionone, γ-isomethyl ionone, and γ-n-methyl ionone; among them, α-isomethyl ionone has the most elegant and soft aroma, and its market demand is larger than other isomers. [0004] Patent CN 106045831 A and patent CN 1394841 A can only synthesize pseudoisomethyl ionone with citral and butanone as raw materials. The document "Synthesis of Methyl Ionone" published by Huang Xigen describes that under the action of solid super acid , Pseudomethyl ionon...

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): C07C45/67C07C49/21
CPCC07B2200/09C07C45/67C07C45/74C07C49/203C07C49/21
Inventor 马啸方万军许鹏宋江李玉祥殷治国徐玉之付振达钟娟娟
Owner SHANDONG NHU PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap