Method for synthesizing 1, 8-cineole by catalyzing alpha-terpilenol through solvent-free system

A terpineol, solvent-free technology, applied in the field of organic synthesis, can solve the problems of low selectivity and no practical value of 1,8-cineole, and achieve the effect of simple operation

Pending Publication Date: 2022-03-25
NANCHANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The isomerization reactions of α-terpineol reported in the literature all need to be completed in organic solvents such as dichloromethane and n-hexane, and the selectivity of 1,8-cineole is low, which is basically of no practical value

Method used

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  • Method for synthesizing 1, 8-cineole by catalyzing alpha-terpilenol through solvent-free system
  • Method for synthesizing 1, 8-cineole by catalyzing alpha-terpilenol through solvent-free system
  • Method for synthesizing 1, 8-cineole by catalyzing alpha-terpilenol through solvent-free system

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The method for catalyzing α-terpineol to synthesize 1,8-cineole in a solvent-free system comprises the following steps:

[0018] Step 1: Add 0.364g of cetyltrimethylammonium bromide and 2.880g of phosphotungstic acid to 30 mL of ethanol with a volume fraction of 95% in sequence, reflux and stir at 90°C for 10 hours, and the stirring speed is 900 rpm. The solvent was removed under reduced pressure, and vacuum-dried at 60°C for 3 hours to obtain 3.100 g of white solid catalyst hexadecyltrimethylammonium phosphotungstic acid;

[0019] Step 2: Add 1.000g cetyltrimethylammonium phosphotungstic acid to 10mL α-terpineol, heat to 60°C and stir for 10 hours at a stirring speed of 900 rpm. After the reaction, cool the reaction product to 5 ℃, the catalyst was recovered by suction filtration, and the obtained oily product was detected by GC ( figure 1 ), with toluene as the internal standard, the calculated 1,8-cineole content was 40%, and the residual α-terpineol content was 5%....

Embodiment 2

[0021] The method for catalyzing α-terpineol to synthesize 1,8-cineole in a solvent-free system comprises the following steps:

[0022] Step 1: Add 0.640g of hexadecyltrimethylammonium chloride and 5.760g of phosphotungstic acid to 60 mL of ethanol with a volume fraction of 95% in sequence, reflux and stir at 90°C for 10 hours, and the stirring speed is 900 rpm. The solvent was removed under reduced pressure, and vacuum-dried at 60°C for 6 hours to obtain 6.188 g of white solid catalyst hexadecyltrimethylammonium phosphotungstic acid;

[0023] Step 2: Add 0.120g of cetyltrimethylammonium phosphotungstic acid into 2mL of α-terpineol, heat to 55°C and stir for 10 hours at a stirring speed of 900 rpm. After the reaction, cool the reaction solution to 5 ℃, the catalyst was recovered by suction filtration, and the obtained oily product was detected by GC ( figure 2 ), using toluene as the internal standard, the calculated 1,8-cineole content was 33%, and the residual α-terpineol ...

Embodiment 3

[0025] The method for catalyzing α-terpineol to synthesize 1,8-cineole in a solvent-free system comprises the following steps:

[0026] Step 1: Add 0.207g of n-octyltrimethylammonium chloride and 1.440g of phosphotungstic acid to 20 mL of ethanol with a volume fraction of 95% in sequence, and reflux and stir at 90°C for 8 hours at a stirring speed of 900 rpm. The solvent was removed under pressure, and vacuum-dried at 60°C for 4 hours to obtain 1.600 g of white solid catalyst n-octyltrimethylammonium phosphotungstic acid;

[0027] Step 2: Add 0.240g of n-octyltrimethylammonium phosphotungstic acid into 8mL of α-terpineol, heat to 60°C and stir for 10 hours at a stirring speed of 900 rpm. After the reaction, cool the reaction solution to 5°C , the catalyst was recovered by suction filtration, and the obtained oily product was detected by GC ( image 3 ), using toluene as the internal standard, the calculated 1,8-cineole content was 35%, and the residual α-terpineol content was...

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Abstract

The invention relates to a method for synthesizing 1, 8-cineole by catalyzing alpha-terpilenol in a solvent-free system, which adopts a solid catalyst prepared from a quaternary ammonium salt compound and phosphotungstic acid to catalyze the alpha-terpilenol to synthesize the 1, 8-cineole in a solvent-free environment. Wherein the molar ratio of the quaternary ammonium salt compound to the phosphotungstic acid is (1: 1)-(1: 3), the dosage of the solid catalyst is 10%-25% of the mass of the raw material alpha-terpilenol, and the alpha-terpilenol is stirred to react for 10-15 hours at the temperature of 50-80 DEG C and the speed of 500-900 r / min. The prepared solid catalyst can be recycled, no solvent needs to be added, nitrogen protection is not needed, operation is easy, environment friendliness is achieved, the terpilenol conversion rate reaches 81%-98%, the content of 1, 8-cineole in the product reaches 30%-45%, by-products limonene and pinene can serve as fragrant raw materials, and commercial value is achieved.

Description

technical field [0001] The invention relates to a method for catalyzing α-terpineol to synthesize 1,8-cineole in a solvent-free system, and specifically belongs to the technical field of organic synthesis. Background technique [0002] 1,8-Cineole is a fragrance raw material for preparing flavors, and is widely used in food flavors, medicinal soaps, sprays, cosmetic flavors and other hygiene products. More importantly, 1,8-cineole has antibacterial and anti-inflammatory effects, and high-purity 1,8-cineole is an important active ingredient of some antipyretic and cough-relieving drugs. Natural 1,8-cineole is mainly derived from eucalyptus oil. Restricted by environmental factors, the output of eucalyptus oil has been declining year by year, which can no longer meet the market demand. Therefore, the chemical synthesis of 1,8-cineole has gradually attracted people's attention. α-Terpineol is a downstream product of turpentine, which is abundant in output and only one-tenth o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08B01J27/188B01J31/02B01J31/34
CPCC07D493/08B01J31/0239B01J31/34B01J27/188Y02P20/584
Inventor 王振希曹锰刘颖婷刘瑞铧杨凌峰
Owner NANCHANG INST OF TECH
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