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A kind of synthetic method of 4-oxo-beta-ionone

A technology of ionone and synthesis method, applied in the field of perfume synthesis, can solve the problems of low yield, large environmental pollution, long reaction steps, etc., and achieve the effects of high yield, good reaction selectivity and mild reaction conditions

Inactive Publication Date: 2015-09-23
CHANGSHA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the biggest disadvantage of the chromium salt oxidation method is that the large amount of chromium salt is used, which is easy to cause serious environmental pollution.
However, the halide oxidation method is not easy to control the conditions, and the reaction yield fluctuates greatly.
The biological oxidation method is difficult to achieve mass production, and the electrolytic oxidation method has many by-products, low yield and high energy consumption
[0004] At present, the molecular oxygen oxidation method catalyzed by transition metals has received more attention. However, the molecular oxygen oxidation method is also difficult to achieve mass production due to the disadvantages of catalyst removal, long reaction steps, and certain dangers in the reaction, such as Oonoshi et al. (JP : 56161370, 1981-12-11.) report β-ionone enol esterification, molecular oxygen catalytic oxidation again, hydrolysis obtains 4-oxo-β-ionone, the reaction step of this method is long, and total productive rate lower
[0005] Patent CN101244992A discloses that N-bromosuccinimide can oxidize β-ionone in one step to prepare 4-oxo-β-ionone. In this method, the oxidant NBS is relatively unstable, which is relatively irritating to the human body and slightly pollutes the environment. big disadvantage

Method used

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  • A kind of synthetic method of 4-oxo-beta-ionone
  • A kind of synthetic method of 4-oxo-beta-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1.92g β-ionone, 0.6g sodium hydroxide (equivalent to 1.5 times the molar ratio of β-ionone), 20mL water, 3.3g dibromohydantoin (equivalent to 1.1 times the molar ratio of β-ionone), stirring at room temperature , reacted for 5h, the reaction was completed, and purified by column chromatography to obtain 1.75g ​​of 4-oxo-β-ionone with a yield of 85%. In addition, there was a little 3,4-dehydro-β-ionone in the crude product by GC-MS analysis. The isolated 4-oxo-β-ionone is a light yellow crystal with a melting point of 50°C to 52°C. Through GC-MS analysis, its molecular ion peak is 206 (molecular ion peak M + , abundance 72%), fragment peaks are 163 (100%), 149 (20%), 135 (25%), 121 (47%); 1 H-MNR (CD 3 Cl, 400MHz) δ: 1.20(s, 6H), 1.80(d, J=0.9Hz, 3H), 1.88~1.93(m, 2H), 2.36(s, 3H), 2.52~2.57(m, 2H), 6.19(d, J=16.5Hz, 1H), 7.25(dd, J=16.5Hz, J=0.9Hz, 1H); 13 C-MNRδ: 13.3, 27.2, 27.9, 34.1, 35.4, 37.2, 131.3, 133.5, 140.3, 157.7, 197.4, 198.5. Consistent with literatu...

Embodiment 2

[0025] Example 1 was repeated according to the same steps described, the amount of dibromohydantoin was reduced to 1.5g (equivalent to 0.5 times the molar ratio of β-ionone), after 6 hours of reaction, the reaction was completed, and column chromatography was separated and purified to obtain 4- Oxo-β-ionone 0.76g, yield 37%. After GC-MS analysis, the result was the same as above.

Embodiment 3

[0027] Example 1 was repeated according to the same steps described, the amount of dibromohydantoin was increased to 4.5g (equivalent to 1.5 times the molar ratio of β-ionone), after 4 hours of reaction, the reaction was completed, and column chromatography was separated and purified to obtain 4- Oxo-β-ionone 1.28g, the yield is 62%. After GC-MS analysis, the result was the same as above.

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Abstract

The invention relates to a method for synthesizing 4-oxo-beta-ionone, concretely a method of adding dibromohydantoin into beta-ionone, and reacting under exist of an alkali and a solvent. The yield of 4-oxo-beta-ionone synthesized by the method can reach 85%, and the method has advantages of simpleness, mild reaction condition, high yield, and easy implementation of batch production.

Description

technical field [0001] The present invention relates to a synthetic method of spices, in particular to a synthetic method of 4-oxo-β-ionone. Background technique [0002] 4-Oxo-β-ionone is an important one of a series of carotenoid degradation products and spices in tobacco. It can soften and delicate smoke in cigarette smoking and improve the sensory quality of cigarettes. [0003] Direct oxidation of β-ionone to prepare 4-oxo-β-ionone mainly includes chromium salt oxidation method, halogen salt oxidation method, biological oxidation method, electrolytic oxidation method, transition metal catalyzed molecular oxidation method, N-bromo Succinimide (NBS) oxidation method, etc. Among them, the biggest disadvantage of the chromium salt oxidation method is that the amount of chromium salt is large, which is easy to cause serious environmental pollution. However, in the halide oxidation method, the conditions are not easy to control, and the reaction yield fluctuates greatly. T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/603C07C45/28
CPCC07C45/28C07C2601/16C07C49/647
Inventor 黎成勇陈雄杨华武王超黎艳玲
Owner CHANGSHA UNIVERSITY