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Synthesis method of dimethyl octenone

A technology for the finished product of dimethyl octenone and dimethyl octenone, which is applied to the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, etc., can solve problems such as poor safety and no reported synthesis, and achieve Effects of mild conditions, less pollution, and simple process routes

Pending Publication Date: 2021-02-05
TIANJIN ANKAITE CATALYST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Dimethyl octenone, another name: 2,5-dimethyl-2-octen-6-one, is a kind of artificially synthesized fragrance, which has not been reported in nature, and there is almost no report on the synthesis of this kind of fragrance in China.
[0003] According to foreign reports, it is synthesized with isobutylene and isopentenone at 300 ° C and a pressure of 15 MPa, and the safety of high temperature and high pressure synthesis is poor.

Method used

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  • Synthesis method of dimethyl octenone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 25.8g of 3-pentanone, 64g of NaOH solution with a mass fraction of 50%, and 0.6g of trioctylmethylammonium chloride into a stirred four-necked flask, stir and heat up to 30°C, and dropwise add 3,3-di 14.9g of methallyl bromide, the dropping rate is 12ml / h, after the dropwise addition, continue to stir for 1h, take a sample for detection, all 3,3-dimethylallyl bromide has reacted, stop stirring, let stand and separate , to obtain an aqueous phase and an organic phase, the aqueous phase was extracted 3 times with 25.8g 3-pentanone to obtain an organic phase, and then the organic phase was combined with the organic phase obtained by the reaction; the 3-pentanone solvent was first distilled out, and then the vacuum distillation Dimethyl octenone was extracted to obtain 12.6 g of finished product (95%) of dimethyl octenone, and the yield of dimethyl octenone was 82%.

Embodiment 2

[0033] Add 25.8g of 3-pentanone, 64g of KOH solution with a mass fraction of 50%, and 0.6g of trioctylmethylammonium chloride into a stirred four-neck flask, stir and raise the temperature to 25°C, and dropwise add 3,3-di 14.9g of methallyl bromide, the dropping rate is 12ml / h, after the dropwise addition, continue to stir for 1h, take a sample for detection, all 3,3-dimethylallyl bromide has reacted, stop stirring, let stand and separate , to obtain an aqueous phase and an organic phase, the aqueous phase was extracted 3 times with 25.8g 3-pentanone to obtain an organic phase, and then the organic phase was combined with the organic phase obtained by the reaction; the 3-pentanone solvent was first distilled out, and then the vacuum distillation Dimethyl octenone was extracted to obtain 12.8 g of finished product (95%) of dimethyl octenone, and the yield of dimethyl octenone was 83.1%.

Embodiment 3

[0035] Add 25.8g of 3-pentanone, 64g of NaOH solution with a mass fraction of 50%, and 0.8g of benzyltriethylammonium chloride into a stirred four-necked flask, stir and heat up to 30°C, and dropwise add 3,3-diethylammonium chloride 14.9g of methallyl bromide, the dropping rate is 12ml / h, after the dropwise addition, continue to stir for 1h, take a sample for detection, all 3,3-dimethylallyl bromide has reacted, stop stirring, let stand and separate , to obtain an aqueous phase and an organic phase, the aqueous phase was extracted 3 times with 25.8g 3-pentanone to obtain an organic phase, and then the organic phase was combined with the organic phase obtained by the reaction; the 3-pentanone solvent was first distilled out, and then the vacuum distillation Dimethyl octenone was extracted to obtain 12.1 g of finished product (95%) of dimethyl octenone, and the yield of dimethyl octenone was 78.5%.

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Abstract

The invention provides a synthesis method of dimethyl octenone. The method comprises the following steps: (1) adding 3-pentanone, 50 wt% of basic catalyst, and a phase transfer catalyst into a four-neck flask with a stirring function, and heating to 20-50 DEG C while stirring; (2) dropwise adding 3, 3-dimethyl allyl bromide, continuously stirring for 1 hour after dropwise adding, sampling and detecting, stopping stirring when the 3, 3-dimethyl allyl bromide is completely reacted, and standing for layering to obtain an organic phase and a water phase; and (3) extracting the water phase obtainedin the step (2) by using 3-pentanone to obtain an organic phase, combining the organic phase with the organic phase obtained in the step (2), and distilling to obtain a dimethyl octenone finished product. According to the synthesis method of the dimethyl octenone, a bimolecular nucleophilic substitution reaction (SN2) of halogenated hydrocarbon is carried out, and a-site hydrogen of carbonyl is substituted with long-chain branched chain brominated hydrocarbon; the method is simple in process route, capable of being completed in one step and mild in condition.

Description

technical field [0001] The invention belongs to the field of artificially synthesized perfumes, in particular to a method for synthesizing dimethyl octenone. Background technique [0002] Dimethyl octenone, another name: 2,5-dimethyl-2-octen-6-one, is a synthetic fragrance, which has not been reported in nature, and there is almost no report on the synthesis of this fragrance in China. Orange fragrance, fresh fruity fragrance, the best use effect in orange fragrance type, can evoke the bitterness of natural orange. Combining with fresh fragrance can improve the hair permeability of the whole composition. Use with certain modern fragrances for a natural grapefruit aroma effect. Smell the fragrance paper for 2 hours. Used in high-grade daily chemical essence, beauty products, soap, washing and ironing care products, and household products. [0003] According to foreign reports, it is synthesized with isobutylene and isopentenone at 300°C and a pressure of 15 MPa. The safet...

Claims

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Application Information

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IPC IPC(8): C07C45/68C07C49/203B01J31/02
CPCC07C45/68B01J31/0239B01J2231/4205
Inventor 辛永民高志国高深
Owner TIANJIN ANKAITE CATALYST
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