A kind of preparation method of perfume 6-methyl-3-hepten-2-one

A technology of methyl and heptene, applied in the field of preparation of 6-methyl-3-hepten-2-one, can solve the problems of low conversion rate of raw materials, poor selectivity, high cost and unsuitability, and achieve overall yield High, high conversion rate, good for environmental protection

Active Publication Date: 2018-09-25
SHANDONG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. The catalytic time is longer, that is, the reaction time and dehydration time are longer;
[0007] 2. The solvent DMSO is a solvent, which is not conducive to environmental protection and the cost is too high to be suitable for large-scale industrial production;
[0008] 3. The yield is low, and there is no precedent for industrial application. The ratio of 6-methyl-4-heptanol-2-one to 6-methyl-3-hepten-2-one is 60:10. The selectivity is poor, the conversion rate of raw materials is low, and it is not suitable for the production and preparation of 6-methyl-3-hepten-2-one

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 A preparation method of spice 6-methyl-3-hepten-2-one

[0042] Include the following steps:

[0043] (1) Dissolution of the main catalyst and co-catalyst

[0044] Mix 10.1g (0.1mol) of prolinol, 180g (10mol) of water, and 12.02g (0.1mol) of di-n-butylamine into a 1000ml four-neck flask, cool and stir;

[0045] (2) Add solvent

[0046] Add solvent cyclohexane 300g (3.57mol);

[0047] (3) Add acetone

[0048] Then add acetone 58g (1mol);

[0049] (4) Add isovaleraldehyde dropwise

[0050] After cooling down to 10°C, start to add 86g (1mol) of isovaleraldehyde dropwise for 2 hours;

[0051] (5) Insulation reaction

[0052] After the dropwise addition, keep the temperature for 1.5 hours until the gas phase analysis of the isovaleraldehyde content is less than 0.60%; the gas phase analysis of the reaction mixture is 6-methyl-3 hepten-2-one and 6-methyl-4-heptanol-2- The total ketone content of ketones is greater than 96.00%;

[0053] (6) Distillation

[0...

Embodiment 2

[0055] Example 2 A preparation method of spice 6-methyl-3-hepten-2-one

[0056] Include the following steps:

[0057] (1) Dissolution of the main catalyst and co-catalyst

[0058]Mix 10.1g (0.1mol) of prolinol, 180g (10mol) of water, and 12.02g (0.1mol) of di-n-butylamine into a 1000ml four-necked flask, and stir;

[0059] (2) Add solvent

[0060] Add solvent n-hexane 300g (3.49mol);

[0061] (3) Add acetone

[0062] Then add acetone 58g (1mol);

[0063] (4) Add isovaleraldehyde dropwise

[0064] Raise the temperature to 30°C, start to add 86g (1mol) of isovaleraldehyde dropwise, and the dropwise addition time is 3 hours;

[0065] (5) Insulation reaction

[0066] After the dropwise addition, keep the heat for 1.0 hours until the gas phase analysis of the isovaleraldehyde content is less than 0.70%; the gas phase analysis of the reaction mixture is 6-methyl-3 hepten-2-one and 6-methyl-4-heptanol-2- The total ketone content of ketones is greater than 96.00%;

[0067] (6...

Embodiment 3

[0069] Embodiment 3 A kind of preparation method of perfume 6-methyl-3-hepten-2-one

[0070] Include the following steps:

[0071] (1) Dissolution of main catalyst and auxiliary catalyst

[0072] Mix 10.1g (0.1mol) of prolinol, 180g (10mol) of water, and 12.02g (0.1mol) of di-n-butylamine into a 1000ml four-necked flask, and stir;

[0073] (2) Add solvent

[0074] Add solvent toluene 400g (4.32mol);

[0075] (3) Add acetone

[0076] Then add acetone 58g (1mol);

[0077] (4) Add isovaleraldehyde dropwise

[0078] Raise the temperature to 50°C, start to add 86g (1mol) of isovaleraldehyde dropwise, and the dropwise addition time is 4 hours;

[0079] (5) Insulation reaction

[0080] After the dropwise addition, keep warm for 0.5 hours until the gas phase analysis of the isovaleraldehyde content is less than 0.60%; gas phase analysis of the reaction mixture 6-methyl-3 hepten-2-one and 6-methyl-4-heptanol-2- The total ketone content of ketones is greater than 96.00%;

[008...

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PUM

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Abstract

The invention provides a preparation method of a perfume 6-methyl-3-heptene-2-one. The method mainly comprises the following steps: dissolving a major catalyst and a cocatalyst, adding a solvent, adding acetone, and adding isovaleraldehyde in a dropwise manner. The overall yield of the above product is high, and the total yield of two compounds 6-methyl-3-heptene-2-one and 6-methyl-4-heptanol-2-one is 95.4-96.41%; the content of 6-methyl-3-heptene-2-one is 94.27-96.41%; the content of 6-methyl-4-heptanol-2-one is 1.00-3.00%; the content of 6-methyl-3-heptene-2-one obtained after rectification reaches 99.10% or above; the raw material conversion rate is high, and the isovaleraldehyde conversion rate is 99.10-99.40%; the catalysis time is short and is 3.5-4.5h; and the solvent adopts cyclohexane, n-hexane and other alkane solvents, so the solvent can be easily obtained by factories, so environmental protection is facilitated, and the cost is reduced.

Description

technical field [0001] The invention relates to a preparation method of 6-methyl-3-hepten-2-one, in particular to the improvement of the process and catalyst in the preparation method, and belongs to the technical field of chemical synthesis. Background technique [0002] 6-Methyl-3-hepten-2-one is an α, β-unsaturated methyl ketone compound. This type of organic compound is widely used in many aspects such as pesticides and food additives. It is also an important Flavor raw material, 6-methyl-3-heptan-2-one is a newly announced new fragrance raw material, which has an apple smell and stable chemical properties. In recent years, proline, as a new catalyst, has been used in the synthesis of α, β-unsaturated ketone compounds. [0003] In the article "Proline-CatalyzedAsymmetric Aldol Reactions between Ketones and r-Unsubstituted Aldehydes" in "ORGANNIC LETEERS" Vol.3, No.4 in 2001, it was pointed out that at room temperature, with DMSO as the solvent and only proline as the ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/72C07C49/203
CPCC07C45/72C07C49/203
Inventor 胡水涛马啸徐玉之颜肖兵付振达刘丛锦姜晓阳
Owner SHANDONG NHU PHARMA
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