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Preparation method of high-purity 12-methyl tridecaldehyde

A methyl tridecaldehyde and high-purity technology is applied in the field of preparation of high-purity 12-methyl tridecaldehyde, can solve the problems of long reaction steps, heavy metal pollution and high risk, achieves low cost, mild reaction conditions, The effect of reducing production costs

Active Publication Date: 2018-10-12
石家庄和中科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Method 3 and method 4 have expensive raw materials and long reaction steps. In method 3, n-butyllithium is used, which is a flammable and dangerous reagent, and the risk is high. In method 4, mercury acetate is used as a reaction reagent, which is likely to cause heavy metal pollution. The three wastes are relatively large

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  • Preparation method of high-purity 12-methyl tridecaldehyde
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  • Preparation method of high-purity 12-methyl tridecaldehyde

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preparation example Construction

[0069] The synthetic route of the preparation method of described high-purity 12-methyl tridecaldehyde is as follows:

[0070] The preparation method of described high-purity 12-methyl tridecanal comprises the following steps:

[0071] A preparation method of high-purity 12-methyl tridecaldehyde, which uses 10-undecylenic acid as a raw material, undergoes four steps of amidation reaction, Grignard reaction, hydrogenation reduction and alkenyl ozonation, and obtains the final product , the specific operation is as follows:

[0072] Step one amidation reaction

[0073] At room temperature, add dichloromethane and 10-undecylenic acid to the reaction kettle, add thionyl chloride dropwise under stirring, and react at 10-40°C to detect the completion of the reaction, and then concentrate to obtain A; 10-undecylenic acid The mass volume ratio of enoic acid and dichloromethane is 1g:16~25ml; the molar ratio of 10-undecylenic acid and thionyl chloride is 1:2~4;

[0074]

[0075] ...

Embodiment 1

[0091] Step one amidation reaction

[0092] At room temperature, add 800ml of dichloromethane and 50g of 10-undecylenic acid into the reaction kettle, add 64.6g of thionyl chloride dropwise under stirring, and raise the temperature to 40°C to react after the dropwise completion, and then concentrate to obtain A;

[0093] At room temperature, add 291ml of dichloromethane and 29.1g of N,O-dimethylhydroxylamine hydrochloride to the reaction kettle, cool down to 0°C, add the dichloromethane solution of molecule A dropwise, and rise to 40°C to react after dropping;

[0094] GC detects the reaction, after the reaction is completed, add 150ml of dilute hydrochloric acid with a mass fraction of 20% to the reaction kettle dropwise, fully stir for 20-60min, separate the liquids, extract the aqueous phase with 270ml of dichloromethane in batches for three times, combine the dichloromethane phases, and dry. Concentrated to obtain 63.3gB, gas chromatography mass spectrometry purity 95.0%, ...

Embodiment 2

[0104] Step one amidation reaction

[0105] At room temperature, add 1250ml of dichloromethane and 50g of 10-undecylenic acid into the reaction kettle, add dropwise 129.1g of thionyl chloride under stirring, and react at 10°C to detect the completion of the reaction, and then concentrate to obtain A;

[0106] At room temperature, add 344ml of dichloromethane and 34.4g of N,O-dimethylhydroxylamine hydrochloride to the reaction kettle at one time, cool down to 5°C, add the dichloromethane solution of molecule A dropwise, and rise to 10°C for reaction ;

[0107] GC detects the reaction, after the reaction is completed, add 400ml of 5wt% dilute hydrochloric acid dropwise to the reaction kettle, fully stir for 20-60min, separate the liquids, extract the water phase with 300ml dichloromethane in batches for three times, combine the dichloromethane phases, dry, concentrate, Obtained 62.0g B, gas phase mass spectrometry purity 96.3%, yield 96.8%;

[0108] Step 2 Grignard reaction

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Abstract

The invention relates to the field of fine chemical engineering, in particular to a preparation method of high-purity 12-methyltridecanal: 10-undecylenic acid is taken as a raw material, and is subjected to four-step reactions including amidation, Grignard reaction, hydrogenation reduction and alkenyl ozonation. The method has the advantages that the raw material is low in cost and easy to obtain, steps are few, reaction conditions are mild, the impurity content is low, the purification is easy, the reaction repeatability is high, the stability is high, and the method is suitable for industrial mass production.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a preparation method of high-purity 12-methyl tridecanal. Background technique [0002] 12-methyl tridecaldehyde is a newly emerging monomer raw material for salty flavor in recent years. This compound naturally exists in beef stew juice, lamb, red deer, chicken and turkey, and can be used in food processing. It has the aroma of tallow, the first aroma of fried food, and the aroma of chicken fat. It is still fragrant under the condition of high dilution; at the same time, because of its large molecular weight and high boiling point, this compound can be widely used in high temperature resistance and retention. It can also be used in high-grade fruit flavors in long-lasting salty flavors. [0003] Due to its huge economic value and application value, its artificial synthesis process is also being continuously explored by chemists, and there are few records on the synthesis m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/40C07C47/02
CPCC07C1/2076C07C45/004C07C45/40C07C45/455C07C51/60C07C259/06C07C57/66C07C49/203C07C11/02C07C47/02
Inventor 郭军永张乱青
Owner 石家庄和中科技有限公司
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