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Application of acidic ionic liquid in high-selectivity synthesis of n-borneol

An acidic ionic liquid, high-selectivity technology, applied in the chemical industry, can solve the problems of potential safety hazards, unfavorable industrial production, and unfavorable industrialization of active components, and achieve the effects of short cycle, strong acidity, and pollution reduction.

Active Publication Date: 2020-11-03
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But S 2 o 8 2- It is an active component that has safety hazards and is prone to explosion, which is not conducive to industrialization; acidic ionic liquids, acetic acid and chloroacetic acid form a composite catalytic system, the conversion rate of α-pinene is up to 95.90%, and the selectivity of bornyl acetate is the highest It is 45.07%, although this ionic liquid embodies good catalytic performance, the compound system that adopts chloroacetic acid to form is not environmentally friendly, and chloroacetic acid belongs to dangerous goods, is unfavorable for industrialized production; The content is only 82.05%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: The method for catalyzing the synthesis of orthoborneol by this acidic ionic liquid is as follows:

[0020] (1) According to the molar ratio of N-methylimidazole:1,4-butane sultone is 1:1, add N-methylimidazole and 1,4-butane sultone into the single-necked flask in sequence , then measure toluene as a solvent and add it to a single-necked flask, place the single-necked flask in a water bath and heat it to 50°C, and stir for 7 hours. After the reaction, filter under reduced pressure, wash the filter cake with ether three times, and dry it under vacuum at 80°C for 12 hours , to obtain a white solid;

[0021] (2) According to the ratio of concentrated sulfuric acid: white solid molar ratio of 1:1, add concentrated sulfuric acid to the white solid, mix well and place it in an oil bath at 80°C for 8 hours, wash with ethyl acetate after the reaction, 80 °C rotary evaporation to obtain a light yellow viscous liquid, that is, an acidic ionic liquid;

[0022] (3)...

Embodiment 2

[0023] Embodiment 2: The method for catalyzing the synthesis of orthoborneol by this acidic ionic liquid is as follows:

[0024] (1) According to the molar ratio of N-methylimidazole:1,4-butane sultone is 1:0.9, add N-methylimidazole and 1,4-butane sultone into a single-necked flask in sequence , then measure toluene as a solvent and add it to a single-necked flask, place the single-necked flask in a water bath to heat and stir, the reaction temperature of the water bath is 60°C, and react for 6h. Drying at lower temperature for 12h gave a white solid;

[0025] (2) According to the ratio of concentrated sulfuric acid: white solid intermediate molar ratio of 0.5:0.6, add concentrated sulfuric acid to the white solid, mix well and react in 80°C oil bath for 12h, wash with ethyl acetate after the reaction, 80 °C rotary evaporation to obtain a light yellow viscous liquid, that is, an acidic ionic liquid;

[0026] (3) Add the acidic ionic liquid and α-pinene to the flask at a mas...

Embodiment 3

[0027] Embodiment 3: The method for catalyzing the synthesis of orthoborneol by this acidic ionic liquid is as follows:

[0028] (1) According to the molar ratio of N-methylimidazole:1,4-butane sultone is 0.9:0.5, add N-methylimidazole and 1,4-butane sultone into the single-necked flask in sequence , then measure toluene as a solvent and add it to a single-necked flask, place the single-necked flask in a water bath to heat and stir, the temperature of the water bath is 40°C, and react for 10 hours. Drying at lower temperature for 12h gave a white solid;

[0029] (2) According to the ratio of concentrated sulfuric acid: white solid intermediate molar ratio of 0.7:0.5, after mixing, react at 80°C for 10h, wash with ethyl acetate after the reaction, and rotary evaporate to obtain a light yellow viscous liquid, that is, acidic Ionic liquid catalyst;

[0030](3) Add the acidic ionic liquid catalyst and α-pinene into the flask according to the mass ratio of 9%, and then add acetic...

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Abstract

The invention discloses an application of an acidic ionic liquid in high-selectivity synthesis of n-borneol, which comprises the following steps: synthesizing an intermediate by using Nmethylimidazoleand 1,4-butane sultone by using toluene as a solvent, washing the reaction product with diethyl ether, drying the product, and reacting the dried product with concentrated sulfuric acid to obtain anacidic ionic liquid catalyst 1-sulfonic acid butyl-3-methylimidazole hydrogen sulfate [HSO3(CH2)4mim][HSO4]; then applying the acidic ionic liquid catalyst to alpha-pinene esterification saponification reaction to obtain n-borneol with high selectivity. The application method changes the current situation that chloroacetic acid and the like need to be introduced as cocatalysts to improve the borneol selectivity; the ionic liquid as the catalyst has the advantages of greenness, environmental protection, simple preparation method, easy separation of the product and the catalyst, high conversionrate, high selectivity and the like.

Description

technical field [0001] The invention relates to the application of an acidic ionic liquid in highly selective synthesis of borneol, which belongs to the field of chemical industry. Background technique [0002] Turpentine oil is a kind of natural essential oil obtained from Pinaceae plants. It has a large output in nature and is cheap. Moreover, my country's turpentine oil resources are abundant, and its annual output ranks among the top in the world. Due to its excellent properties, turpentine is widely used in many fields such as medicine, paint, spices and agronomy. The main components of turpentine are α-pinene and β-pinene, and the content of α-pinene is more than 90%. α-pinene has good reactivity in structure, and can undergo many chemical reactions such as esterification, addition, oxidation, reduction, rearrangement, etc., and generate a large number of derivative compounds. Among these compounds, there are not only compounds with ideal aroma, but also functional m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C35/30C07C29/00
CPCC07C29/00C07C35/30
Inventor 蒋丽红黄金艳王亚明杨文娟黄鹏鹏
Owner KUNMING UNIV OF SCI & TECH
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