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Preparation method of alpha-cyclopentadecanone

A kind of cyclopentadecanone, hydroxyl technology, applied in the field of preparing α-hydroxy cyclopentadecanone, can solve the problems of difficult separation, influence of cyclopentadecanone purification and the like

Inactive Publication Date: 2012-12-05
赵阳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, it is difficult to separate the by-products mixed in α-hydroxycyclopentadecone, which has a great influence on the subsequent synthesis and purification of cyclopentadecanone.

Method used

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  • Preparation method of alpha-cyclopentadecanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 11.52 g (0.03 mol) of dibutyl pentadecanedioate to an Erlenmeyer flask containing 30 ml of toluene, and mix well. Add 150ml of toluene and 20g of chlorobenzene into a 500ml four-neck flask equipped with a mechanical stirrer, a thermometer, a condenser, a dropping port, and a nitrogen port. Access to N 2 1. Heat up, when the temperature reaches 100°C, add 3.6g of metallic sodium to the flask, stir vigorously for 5min, and beat the sodium into fine sodium sand. Keeping the temperature at 100°C, a toluene solution of dibutyl pentadecanedioic acid was added dropwise, and the drop was completed in 3 hours. After the dropwise addition was completed, the reaction was kept for 1 hour. After the reaction was completed, 20ml of acetic acid was added dropwise to decompose the remaining metallic sodium. Cool down, filter, wash the filtrate with hot water to neutrality, and distill toluene under reduced pressure to obtain 7.2g. The reaction product was analyzed by gas chromat...

Embodiment 2

[0032] Add 30 g (0.1 mol) dimethyl pentadecanedioate to a Erlenmeyer flask containing 100 ml of toluene, and mix well. Add 328ml of toluene and 76g of bromopentane into a 1000ml four-neck flask equipped with a mechanical stirrer, a thermometer, a condenser, a dropping port, and a nitrogen port. Access to N 2 1. Heat up, when the temperature reaches 105°C, add 10.6g of metallic sodium to the flask, stir vigorously for 5min, and beat the sodium into fine sodium sand. Keeping the temperature at 105°C, a toluene solution of dimethyl pentadecanedioic acid was added dropwise, and the drop was completed in 4 hours. After the dropwise addition was completed, the reaction was kept for 3 hours. After the reaction was completed, the temperature was lowered, and 10 ml of methanol was added dropwise to decompose the remaining sodium metal, filtered, the filtrate was washed with hot water until neutral, and the toluene was distilled off under reduced pressure to obtain 24.2 g. The reactio...

Embodiment 3

[0035] Add 9.84 g (0.03 mol) diethyl pentadecanedioate to a Erlenmeyer flask containing 30 ml of toluene, and mix well. Add 150ml of toluene and 29g of iodobutane into a 500ml four-neck flask equipped with a mechanical stirrer, a thermometer, a condenser, a dropping port, and a nitrogen port. Access to N 2 1. Heat up, when the temperature reaches 100°C, add 3.6g of metallic sodium to the flask, stir vigorously for 5min, and beat the sodium into fine sodium sand. Keeping the temperature at 100°C, a toluene solution of diethyl pentadecanedioic acid was added dropwise, and the drop was completed in 3 hours. After the dropwise addition was completed, the reaction was kept for 2 hours. After the reaction was completed, 20ml of acetic acid was added dropwise to decompose the remaining metallic sodium. Cool down, filter, wash the filtrate with hot water to neutrality, and distill toluene under reduced pressure to obtain 6.8g. The reaction product was analyzed by gas chromatography...

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Abstract

The invention relates to a preparation method of alpha-cyclopentadecanone. According to the preparation method, pentadecane dicarboxylic acid produced by biological fermentation as a raw material is etherified to obtain diester pentadecanedioate; and methylbenzene as solvent and halogenated hydrocarbon as an assistant are subjected to a cyclization reaction to synthesize the alpha-cyclopentadecanone at high yield. The method for synthesizing the alpha-cyclopentadecanone has the characteristics of high conversion rate, fewer side reactions and high yield of alpha-cyclopentadecanone; and meanwhile, the method has the advantages of mild reaction condition, low energy consumption, high quality of products and low production cost of the product, is easy for realization of industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for preparing α-hydroxycyclic pentadecone by using pentadecane dibasic acid ester. Background technique [0002] Cyclopentadecanone (cyclopentadecanone), colorless or white needle-like crystals, has a sweet and powerful musk-like animal aroma, similar to the aroma of natural muscone, soft aroma, good fragrance diffusion and long-lasting. As an excellent deodorant, it is widely used in high-grade perfume, face powder, soap and other daily essences; it is also used in essences of beverages, candies and oral hygiene products. In addition, cyclopentadecanone is also an important intermediate for the synthesis of precious fragrances, raw material muskone and other macrolide musks. [0003] Cyclopentadecanone was first obtained from the glandular secretions of civets and muskrats by leaching. At present, there are fewer and fewer wild musk deer animals, ...

Claims

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Application Information

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IPC IPC(8): C07C49/487C07C45/45
Inventor 赵阳
Owner 赵阳
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