Method for preparing nopinone

A technology of nopinone and preparation process, which is applied in the field of organic synthesis and achieves the effects of high conversion rate, suitable reaction temperature and high selectivity

Active Publication Date: 2019-09-20
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still room for improvement in the process of the existing potassium permanganate oxidation method, such as: the conversion rate of β-pinene, the selectivity of nopinone and the reaction time, etc.

Method used

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  • Method for preparing nopinone
  • Method for preparing nopinone
  • Method for preparing nopinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A preparation method of nopinone, the reagents needed in the preparation process are: β-pinene, potassium permanganate, acetone, acid and catalyst, the preparation method steps are:

[0021] (1) Preparation: In the solvent acetone, mix β-pinene with the catalyst, then add potassium permanganate and acid, set the reaction temperature at 20-30°C, and continue the reaction time of 1-4h to obtain nopinene crude product;

[0022] (2) Purification: add 50mL ethyl acetate to the crude product of nopinone obtained above for extraction, then add a mass fraction of 5% sodium sulfite solution for washing, suction filtration, and the filtrate is washed with water and saturated saline, and finally Anhydrous sodium sulfate is dried to obtain the finished product of nopinone.

[0023] Wherein the catalyst is a surfactant, the molar ratio of β-pinene to potassium permanganate is 1:1 to 1:4, the molar ratio of β-pinene to acetone is 1:30 to 1:300, and the molar ratio of β-pinene to pot...

Embodiment 2

[0027] Take 5.000g (37mmol) of β-pinene in a 100mL three-necked flask, accurately weigh 0.2g (0.55mmol) of hexadecyltrimethylammonium bromide in the beaker, and continue to add 30mL of acetone and 3mL of soluble 2mol / L sulfuric acid to completely dissolve cetyl ammonium bromide, then pour it into a three-necked flask, use mechanical stirring, control the speed at 220r / min, and condense with a condenser. Keep the temperature steady at 21 °C. Add 18.6g (118mmol) potassium permanganate powder to there-necked flask, add in 1 minute. Continuous reaction 2h. After the reaction is completed, use 50 mL of ethyl acetate to wash twice and filter with suction. If the filtrate is purple, use an appropriate amount of 5% sodium sulfite solution for washing. After the filtrate is purple, a solid precipitate of manganese dioxide will be produced. , and then filter. Use 75mL water to wash 2 times, then wash with 80mL saturated salt water (2 times), after detecting neutrality with pH test pa...

Embodiment 3

[0029] Take 5.000g (37mmol) of β-pinene in a 100mL three-necked flask, accurately weigh 0.2g (2.2mmol) of 2-bromoethyltrimethylammonium bromide in the beaker, and continue to add 30mL of acetone and 2.5mL of Hydrochloric acid with a solubility of 2mol / L completely dissolves 2-bromoethyltrimethylammonium bromide, then pours it into a three-necked flask, uses mechanical stirring, controls the speed at 220 r / min, and condenses with a condenser tube. Keep the temperature steady at 23°C. Add 15.0g (95mmol) potassium permanganate powder to the three-necked flask, and finish adding within 1 minute. Continuous reaction 3h. After the reaction is completed, use 50 mL of ethyl acetate to wash twice and filter with suction. If the filtrate is purple, use an appropriate amount of 5% sodium sulfite solution for washing. After the filtrate is purple, a solid precipitate of manganese dioxide will be produced. , and then filter. Use 75mL of water to wash twice, and then wash twice with 80mL...

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Abstract

The invention discloses a method for preparing nopinone. The method for synthesizing the nopinone comprises the following steps: taking beta-pinene as a raw material and acidic potassium permanganate as an oxidant for selectively oxidizing under the action of a surfactant to synthesize the nopinone, the conversion rate of the beta-pinene is more than 99%, and the selectivity of the nopinone is more than 90%. Compared with the prior method, the method has mild reaction conditions, short reaction time, high conversion rate of the raw material and high selectivity of the product, and the method reduces the preparation cost of the nopinone.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic matter, and in particular relates to a preparation method of nopinone. Background technique [0002] my country is a large country of turpentine production, mainly producing gum turpentine by cutting fat. The main components of gum turpentine are gum rosin and gum turpentine, wherein the main components of gum turpentine are α-pinene and β-pinene. Most of the gum turpentine produced in my country is masson pine gum turpentine, in which the content of β-pinene is relatively low, about 5%-10%. It was later found that the β-pinene content in the gum turpentine produced by the Simao pine planted in the Simao area of ​​Yunnan is as high as about 30%, and the β-pinene content in the gum turpentine produced by the slash pine introduced from the United States is as high as 34%. With the increasing yield of β-pinene, how to further process and utilize it has gradually become a hot research i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/34C07C49/433
CPCC07C45/34C07C2602/42C07C49/433
Inventor 廖圣良石云飞王宗德司红燕范国荣陈尚钘王鹏罗海贺璐
Owner JIANGXI AGRICULTURAL UNIVERSITY
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