Method for preparing ionone by using super-strong acid or super-strong-acid-based ionic liquid as catalyst

An ionone and pseudoionone technology, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of low catalyst yield, large catalyst usage, etc., and achieve high reaction conversion rate and Yield effect

Active Publication Date: 2013-02-13
ZHEJIANG NHU CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of existing solid superacid catalysts such as low yield and large catalyst usage, and provide a kind of ionic liquid that utilizes superacid or based on superacid as a catalyst to catalyze pseudoionone A method for synthesizing ionone to achieve high reaction conversion rate and yield, and catalyst recovery and mechanical application for many times still make the reaction conversion rate and yield higher

Method used

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  • Method for preparing ionone by using super-strong acid or super-strong-acid-based ionic liquid as catalyst
  • Method for preparing ionone by using super-strong acid or super-strong-acid-based ionic liquid as catalyst
  • Method for preparing ionone by using super-strong acid or super-strong-acid-based ionic liquid as catalyst

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The preparation of embodiment 1 catalyst

[0020] Both methanesulfonic acid and methanedisulfonic acid involved in the present invention can be purchased through commercial channels.

[0021] 1. Referring to the existing literature (Sustainability 2009.1.161-168) to synthesize methanetrisulfonic acid superacid solid

[0022] 1. Slowly add acetone dropwise to 65% oleum at low temperature and constant temperature, and control the temperature at -2°C±1°C;

[0023] 2. After the dropwise addition is completed, keep the temperature at low temperature for 30 minutes;

[0024] 3. Move the reaction solution to a water bath at 85°C and keep it warm for 3 hours;

[0025] 4. Slowly add the reaction solution to 500ml of ice-cold distilled water, and refrigerate the solution overnight;

[0026] 5. Add KOH caustic soda to the solution to make the pH of the reaction solution around 7.0;

[0027] 6. Pour the reaction solution into a 3L beaker, add distilled water, and refrigerate fo...

Embodiment 2-7

[0038] Embodiment 2-7 Pseudo-ionone synthesizes ionone

[0039]Add 2g of dry methanetrisulfonic acid solid in a three-necked flask, then add 100ml of gasoline, keep stirring at a temperature of 60°C, add 6.5g of pseudo-ionone while stirring, and react at a temperature of 60°C for 1.3 hours, After the reaction, the methyltrisulfonic acid solid catalyst was separated by filtration, then gasoline was separated in a rotary evaporator, and finally the target products α-ionone and β-ionone were separated by vacuum distillation. The conversion rate of raw materials is above 99%, and the yield of ionone is 92%.

[0040] With reference to the above-mentioned synthetic method, select different methyltrisulfonic acid catalyst consumptions, reaction solvent and reaction temperature, the conversion rate and the yield obtained are shown in the following table:

[0041]

Embodiment 8-13

[0043] Referring to the above synthesis method, select different acid catalysts, use gasoline as a solvent, and see the following table for the reaction conversion rate and yield at a temperature of 80°C:

[0044] Example

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Abstract

The invention relates to a method for preparing ionone by catalyzing pseudoionone cyclization by using a super-strong acid or super-strong-acid-based ionic liquid as a catalyst. The existing solid acid catalyst for preparing ionone has obviously lower catalytic efficiency, and the ionone yield is basically lower than 80%, thereby being difficult to implement industrialization from the view of cost. The method comprises the following step: by using the super-strong acid or super-strong-acid-based ionic liquid as a catalyst, reacting at 60-100 DEG C in the presence of a solvent for 1-7 hours to cyclize pseudoionone into ionone. The super-strong acid or super-strong-acid-based ionic liquid is used as the catalyst, thereby implementing high reaction conversion rate and yield; and the catalyst still has high reaction conversion rate and yield after being recovered and used many times.

Description

technical field [0001] The invention relates to a synthesis method of ionone, in particular to a method for catalyzing pseudo-ionone to synthesize ionone by using superacid or ionic liquid based on superacid as a catalyst. Background technique [0002] Ionone is an important class of synthetic fragrance, which has important application value in the fragrance and pharmaceutical industry. There are two common isomers of α-ionone and β-ionone. α-ionone is a colorless to pale yellow liquid with a woody violet smell and is widely used in essences, perfumes and cosmetics. β-ionone is a yellowish liquid, mainly used as soap fragrance. High-purity β-ionone is an important raw material for the synthesis of vitamin A and β-carotene. [0003] Since Hibbert et al. first reported the cyclization of ionones under strong acid conditions by using pseudo-ionones in 1924, people have not stopped researching on this reaction. At present, pseudo-ionones are generally used as raw materials in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/21C07C45/67B01J31/02
CPCY02P20/584
Inventor 毛建拥陈航李浩然陈志荣
Owner ZHEJIANG NHU CO LTD
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