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Synthesis method of dimethyl cyclohexenyl pentenone

A technology of dimethylcyclohexenylpentenone and dimethylcyclohexene, which is applied in the field of chemical synthesis, can solve the problems of many operation steps, many side reactions, and environmental pollution, and achieve the optimization of raw material ratio and high yield Improvement, high yield effect

Pending Publication Date: 2022-04-15
TENGZHOU TIANSHUI BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are very few domestic reports on the synthesis of dimethylcyclohexenylpentenone. Most of them use dehydrolinalool to dehydrate under the catalysis of boric acid to generate the corresponding olefins, and then react with allyl chloride under the catalysis of CuCl / OH- , followed by cyclization and isomerization in an acidic environment. It is not difficult to see that the above method has many operation steps, complex conditions, many side reactions, serious equipment corrosion, and a large amount of three wastes, which will cause serious pollution to the environment.

Method used

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  • Synthesis method of dimethyl cyclohexenyl pentenone
  • Synthesis method of dimethyl cyclohexenyl pentenone
  • Synthesis method of dimethyl cyclohexenyl pentenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1) Preparation of 4.4-dimethylcyclohexene;

[0032] Add 100ml of n-hexane, 274.5g of butadiene and 424.5g of isobutylene into a 1000ml autoclave, then add 1g of benzenesulfonic acid, immediately close the mouth of the autoclave to prevent gasification, stir, and maintain the temperature at -35°C and the pressure at 2.0Mpa. to 2.0MPa, pressurized with nitrogen, reacted at constant temperature for 1.5h, cooled, neutralized with saturated sodium carbonate solution, adjusted to pH 7, separated the organic layer, and precipitated to obtain 4.4-dimethylcyclohexene, mass It was 427.6 g, and the yield was 76.3%.

[0033] 2) Preparation of 4-pentenoyl chloride;

[0034] 2. Add 250ml of 4-pentenoic acid to a 1000ml three-neck round-bottomed flask, add 400g of thionyl chloride dropwise while stirring and cooling down, heat to reflux, and gradually increase the temperature as the reflux time prolongs, then raise the temperature to 100°C and react for 1 hour . Change reflux to di...

Embodiment 2

[0038] 1) Preparation of 4.4-dimethylcyclohexene;

[0039] Add 200ml of n-hexane, 550g of butadiene and 850g of isobutene into a 2000ml autoclave, then add 4g of benzenesulfonic acid, immediately close the mouth of the autoclave to prevent gasification, stir, and maintain the temperature at -30°C and the pressure at 2.0Mpa, if the pressure is less than 2.0 MPa, pressurized with nitrogen, reacted at constant temperature for 1.5h, cooled, neutralized with saturated sodium carbonate solution, adjusted pH to 7, separated the organic layer, and precipitated to obtain 4.4-dimethylcyclohexene with a mass of 800g , the yield was 71.2%.

[0040] 2) Preparation of 4-pentenoyl chloride;

[0041] Add 500ml of 4-pentenoic acid to a 2000ml three-neck round bottom flask, add 800g of thionyl chloride dropwise while stirring and cooling down, heat to reflux, and gradually increase the temperature as the reflux time prolongs, then raise the temperature to 100°C and react for 2 hours. Change r...

Embodiment 3

[0045] 1) Preparation of 4.4-dimethylcyclohexene;

[0046] Add 500ml of n-hexane, 1370g of butadiene and 2122g of isobutene into a 5000ml autoclave, then add 10g of benzenesulfonic acid, immediately close the mouth of the autoclave to prevent gasification, stir, and maintain the temperature at -40°C and the pressure at 2.0Mpa. If the pressure is less than 2.0MPa, pressurize with nitrogen, react at constant temperature for 1 hour, cool down, neutralize with saturated sodium carbonate solution, adjust the pH to 7, separate the organic layer, and desolventize to obtain 4.4-dimethylcyclohexene , the mass is 2080g, and the yield is 74.3%.

[0047] 2) Preparation of 4-pentenoyl chloride;

[0048] Add 1250ml of 4-pentenoic acid to a 5000ml three-necked round-bottomed flask, add 2000g of thionyl chloride dropwise while stirring and cooling down, heat to reflux, and gradually increase the temperature as the reflux time prolongs, then raise the temperature to 100°C and react for 1 hour...

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Abstract

The invention discloses a synthesis method of dimethyl cyclohexenyl pentenone. The method comprises the following steps: synthesizing 4, 4-dimethyl cyclohexene from isobutene and butadiene under medium pressure by taking n-hexane as a solvent and p-toluenesulfonic acid as a catalyst; 4-pentenoic acid reacts with thionyl chloride to produce 4-pentenoyl chloride; dichloromethane is used as a solvent, 4, 4-dimethyl cyclohexene and 4-pentenoyl chloride are synthesized in a saturated sodium bicarbonate aqueous solution, and dimethyl cyclohexenyl pentenone is obtained. According to the method, the raw material ratio and the reaction temperature of the reaction are optimized at the same time, so that high yield of the reaction is achieved, safe and stable operation of the test is effectively guaranteed, and unexpected effects are achieved; according to the invention, the preparation process of the 4-pentenoyl chloride is improved, so that the yield of the 4-pentenoyl chloride is greatly improved, and the yield of the whole preparation process is further improved.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing dimethylcyclohexenylpentenone. Background technique [0002] Dimethylcyclohexenylpentenone is a kind of spice with great application value. It has a strong aroma of Gepong, and has a fragrance like pineapple and hyacinth. It is mainly used in the formulation of daily chemical fragrances, and is mostly used in the fragrance of cosmetics, perfumes, soaps and detergents. [0003] At present, there are very few domestic reports on the synthesis of dimethylcyclohexenylpentenone. Most of them use dehydrolinalool to dehydrate under the catalysis of boric acid to generate the corresponding olefins, and then react with allyl chloride under the catalysis of CuCl / OH- , followed by cyclization and isomerization in an acidic environment. It is not difficult to see that the above method has many operating steps, complex conditions, many side reactions, ser...

Claims

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Application Information

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IPC IPC(8): C07C49/557C07C45/45
Inventor 张士金贾友良张翔洲马兆峰杨仲卿
Owner TENGZHOU TIANSHUI BIO TECH CO LTD
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