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

Method for preparing raspberry ketone under catalysis of multi-sulfonic functionalized ionic liquid

A functional ionic liquid and polysulfonic acid-based technology is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds. It can solve problems such as limiting industrial application value, easy to pollute the environment, and harsh reaction conditions. Improve the industrial application value, reduce the reaction temperature, and improve the effect of reaction yield

Active Publication Date: 2017-07-04
SHANGYU NHU BIOCHEM IND
View PDF7 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has harsh reaction conditions, high cost, difficult recycling of the catalyst, and easy pollution of the environment.
The second is to synthesize raspberry ketone with the natural equivalent anisaldehyde. This method generally requires the use of toxic alkylamines, consumes a large amount of aluminum chloride and hydrochloric acid, and causes serious pollution.
The reaction side reaction of this method is more, aftertreatment is complicated, serious to equipment corrosion, acid is difficult to reclaim, someone uses acidic ionic liquid as catalyst to catalyze phenol and butenone reaction synthesis raspberry ketone later (CN102584554). Small size, less waste, and the catalyst can be recycled
However, the yield of this preparation method is not high, most of the yields are only 30-40%, and the highest yield is only about 50%, which limits the industrial application value of this method

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
  • Method for preparing raspberry ketone under catalysis of multi-sulfonic functionalized ionic liquid
  • Method for preparing raspberry ketone under catalysis of multi-sulfonic functionalized ionic liquid
  • Method for preparing raspberry ketone under catalysis of multi-sulfonic functionalized ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Preparation of catalyst: 145g of hexamethylenetetramine and 368g of 1,3-propane sultone were mixed and stirred at room temperature for 6 hours, and 500ml of ethyl acetate was added as a solvent; Washed three times with ethyl acetate, and dried in vacuum at 60°C to obtain 480 g of ylide, with a yield of 95% relative to 1,3-propane sultone;

[0027] (2) Preparation of raspberry ketone: 480 g of ylide and 400 g of concentrated sulfuric acid were weighed and stirred at 80° C. for 4 hours to obtain the corresponding ionic liquid. 0.6 mole of phenol, 0.8 mole of butenone and 0.2 mole of ionic liquid were put into the reaction vessel, and stirred at 30° C. for 8 hours. Add 2 moles of water, filter and separate to obtain raspberry ketone, and the reaction yield is 79%; unreacted raw materials and catalysts can be used next time after dehydration. The reaction formula is as follows:

[0028]

Embodiment 2～4

[0030] The addition reaction temperature of step (2) of Examples 2 to 4 is shown in Table 1, and other reaction conditions are the same as in Example 1, and the reaction results are shown in Table 1.

[0031] The reaction condition and reaction result of table 1 embodiment 2~4

[0032] Example Reaction temperature °C Yield% 2 40 91 3 50 93 4 60 74

Embodiment 5～7

[0034] The operation of Examples 5-7 is basically the same as that of Example 2, except that the step (2) does not use an ionic liquid as a catalyst, but directly uses an acid to catalyze the reaction. The acid used and the reaction results are shown in Table 2.

[0035] Example acid Yield% 5 sulfuric acid 72 6 phosphoric acid 51 7 p-Toluenesulfonic acid 38

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 discloses a method for preparing raspberry ketone under the catalysis of multi-sulfonic functionalized ionic liquid. According to the method, phenol and methyl vinyl ketone are used as raw materials and the multi-sulfonic functionalized ionic liquid is used as a catalyst for selective catalytic synthesis of raspberry ketone. The ionic catalyst has the advantages of high acid value, low synthesis cost, good catalysis efficiency and reaction activity at room temperature compared with conventional ionic catalysts.

Description

technical field [0001] The invention relates to a method for preparing raspberry ketone by catalyzing a polysulfonic acid group functional ionic liquid, belonging to the field of organic chemical synthesis. Background technique [0002] Raspberry ketone (p-hydroxybutyrophenone), CAS number: 5471-51-2, also known as rubus ketone, is a spice with elegant fruity aroma widely used at home and abroad; it can be used as a food additive in beverages, candies, Biscuits; As a modifier, it is used in jasmine, tuberose and other daily spices; as a fixative, it is widely used in strawberry, raspberry, pineapple, peach and other food flavors. [0003] At present, the synthetic technique of raspberry ketone has three kinds, and the first is to be raw material with p-hydroxybenzaldehyde and acetone, synthesize raspberry ketone (CN1097729) by condensation and hydrogenation reaction. The method has harsh reaction conditions, high cost, difficult recycling of the catalyst, and easy pollution...

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 Applications(China)
IPC IPC(8): C07C45/69C07C49/245B01J31/02
CPCB01J31/0282C07C45/69C07C49/245
Inventor 田金金牛少凤吕国锋黄国东李小军曾庆宇朱旭
Owner SHANGYU NHU BIOCHEM IND
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