Method for preparing methyl cedryl ketone from Chinese fir wood oil

A technology of methyl cedryl ketone and fir oil, which is applied to the preparation of carboxylic acid esters, carbon-based compounds, chemical instruments and methods, etc., can solve the problems of scarcity of cedar resources, long growth cycle of cedar wood, and difficulty in cedar wood oil, etc., to achieve Avoid the hazards of production operators and the environment, facilitate the range of fragrance blending, and facilitate separation

Active Publication Date: 2014-09-17
JIANGXI HUAYU AROMATIC TECH
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AI Technical Summary

Problems solved by technology

However, the growth cycle of cypress is very long, and it takes about 60 years to become useful, resulting in a shortage of cypress resources. Therefore, it is difficult for cypress oil to meet the needs of the spice market.

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  • Method for preparing methyl cedryl ketone from Chinese fir wood oil

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preparation example Construction

[0032] The preparation of niobic acid supported aluminum chloride catalyst in each embodiment:

[0033] Soak 250 grams of niobic acid in 1 mol / L nitric acid solution at room temperature, take it out after 24 hours, then dry it at 120°C for 5 hours, and then bake it at 350°C for 3 hours to obtain pore-expanding niobic acid.

[0034] Add 250 g of pore-expanding niobic acid to 1 liter of saturated solution of aluminum chloride at 70°C in absolute ethanol, heat and reflux for 2.5 h, filter with suction, wash with ethanol until no chloride ions are detected, and dry at 105°C for 2 h , ground through a 120-mesh sieve, solidified in a muffle furnace at 350° C. for 2 hours, cooled at room temperature and placed in a desiccator to obtain a niobic acid-supported aluminum chloride catalyst. The used niobic acid-supported aluminum chloride catalyst was regenerated by calcining at 300° C. for 2 h in a muffle furnace, and the regenerated catalyst was used in the synthesis reaction of methyl...

Embodiment 1

[0036] Chinese fir oil is distilled to obtain firne, which mainly contains α-pinene, β-pinene and α-terpineol.

[0037] Add 210 grams of fircene and 20 grams of niobic acid-loaded aluminum chloride catalyst into the reaction kettle, stir and heat up to 55°C for isomerization reaction for 2 hours, β-pinene is converted into α-pinene, and then start to drop 410 grams of acetic anhydride , After 30 minutes of dropwise addition, stir and heat up to 60°C for acetylation reaction for 5 hours, α-pinene is converted into methyl cedryl ketone through acetylation, and α-terpineol is converted into terpineyl acetate through acetylation. After the reaction, the product was rectified first to distill out acetic anhydride and acetic acid, and then an appropriate amount of crushed ice was added to keep the reaction mixture below 40°C. Stirring was continued for 0.5 h, and the layers were allowed to stand to separate the oil layer and the water layer. % sodium carbonate solution until weakly al...

Embodiment 2

[0039] Add 210 grams of picrene and 15 grams of niobic acid-supported aluminum chloride catalyst into the reaction kettle, stir and heat up to 55°C for isomerization reaction for 2 hours, β-pinene is converted into α-pinene, and then start to drop 320 grams of acetic anhydride , After 30 minutes of dropwise addition, the temperature was raised to 60°C for 7 hours for acetylation reaction with stirring, α-pinene was acetylated into methyl cedryl ketone, and α-terpineol was acetylated into terpineyl acetate. After the reaction, the product was rectified first to distill out acetic anhydride and acetic acid, and then an appropriate amount of crushed ice was added to keep the reaction mixture below 40°C. Stirring was continued for 0.5 h, and the layers were allowed to stand to separate the oil layer and the water layer. % sodium carbonate solution until weakly alkaline, then washed with saturated salt and deionized water until neutral, and the water layer was separated. The washed...

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Abstract

The invention discloses a method for preparing methyl cedryl ketone from Chinese fir wood oil. Methyl cedryl ketone is prepared by using Chinese fir wood alkene obtained by rectifying the Chinese fir wood oil as a raw material, using niobic acid loaded aluminum chloride as an isomerization catalyst of beta-Chinese fir wood alkene and an acetylation catalyst of alpha-Chinese fir wood alkene and alpha-terpilenol, and adopting excessive amounts of acetic anhydride as an acetylation reagent and a reaction solvent, wherein isomerization of Chinese fir wood alkene is performed at 50-60 DEG C, the reaction is performed for 2+ / -0.2 hours, and the dosage of the niobic acid loaded aluminum chloride catalyst accounts for 7-15% of the mass of Chinese fir wood alkene; the acetylation temperature is 60-70 DEG C, the acetylation reaction is performed for 5-7 hours, and the molar dosage of acetic anhydride accounts for 3-5 times of Chinese fir wood alkene. A synthetic method is environment-friendly and simple and convenient in operation, and is suitable for industrial production. A methyl cedryl ketone product prepared by using Chinese fir wood alkene contains terpinyl acetate components, has modification effects on the fragrance of methyl cedryl ketone, is wide in flavor blending application range, and can be used for replacing methyl cedryl ketone prepared by using the Chinese fir wood oil as the raw material so as to solve the limitation of Chinese fir wood oil resources.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and relates to a method for preparing synthetic spices, in particular to a method for preparing methyl cedryl ketone from fir oil. Background technique [0002] Methyl cedryl ketone is an important fragrance raw material, with musk-ambergris woody fragrance, suitable for blending daily-use essences such as sandalwood, woody, ambergris, oriental. Methyl cedryne is usually made from cedarwood oil, which can be obtained by rectification of cedrene, which mainly contains components such as α-cedrene, β-cedrene and phoenix cedrene. [0003] The synthesis of methyl cedryl ketone usually uses cedrene as raw material, sulfuric acid, polyphosphoric acid, superphosphoric acid or solid acid as catalyst, toluene, xylene, methylene chloride or chloroform as organic solvent, β in cedrene - Cedrene is first isomerized into α-cedrene, and cedrene is isomerized into Olefin B, and then α-cedrene and Olef...

Claims

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Application Information

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IPC IPC(8): C07C49/553C07C45/68B01J23/20C07C69/145C07C67/08
CPCB01J23/20C07C5/255C07C45/455C07C2523/20C07C2603/66C07C49/553C07C13/605
Inventor 俞忠华张天古周振华王发祥郑井泉
Owner JIANGXI HUAYU AROMATIC TECH
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