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Synthesis method of alpha-cyclocitral

The technology of a cyclocitral and a synthesis method is applied in the directions of chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., and can solve the problems of unsatisfactory aroma, many beta isomers, large equipment investment, and the like, Achieve the effect of no by-products, high selectivity and less dosage

Active Publication Date: 2018-06-01
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] At present, the synthesis method of methyl ionone is facing the following problems: 1) the method is complicated, and the equipment investment is large; 2) the three wastes are produced; 3) the selectivity is poor, there are many β isomers, and the aroma is not satisfactory

Method used

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  • Synthesis method of alpha-cyclocitral

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Experimental program
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Effect test

Embodiment 1

[0051] 1) Add 84.12g of 1,3-pentadiene, 80.00g of prenal, and 14.67g of aluminum trichloride under the protection of nitrogen into the reaction kettle that has undergone dehydration and deoxidation treatment, and stir and react at 90°C for 1.0h; The temperature was lowered to room temperature, and 180.00 g of crushed ice was poured into the reaction solution, stirred thoroughly for 10 minutes, and then moved to a separatory funnel for static separation to obtain 184.66 g of the aqueous phase and 174.13 g of the organic phase; the organic phase was transferred to the reaction kettle, NMR qualitative, the data are as follows: 1 H-NMR (δ, ppm, 400MHz, CDCl 3 ):0.99(s,3H,-CH 3 ),0.99(s,3H,-CH 3 ),1.75-2.00(m,2H,-CH 2 ),1.11(m,3H,=C-CH 3 ), 1.62~1.69(m, 2H, -CH=CH-), 2.48(d, J=8.0Hz, 1H, -CH-CHO), 5.73(t, J=2.8Hz, 1H, -CH=), 9.72 (s, 1H, -CHO); 13C-NMR (400MHz, CDCl 3 )δ (ppm): 202.3; 131.3; 124.8; 71.8; 40.535.2; 28.2; 27.7; 27.7; Add 2.16g of nickel chloride, 1.42g of zinc...

Embodiment 2

[0055] In the reaction kettle that has been dehydrated and deoxygenated, 84.12g of 1,3-pentadiene, 80.00g of prenaldehyde and 14.67g of aluminum trichloride were added under the protection of nitrogen, and the reaction was stirred at 80°C for 1.0h; the temperature dropped to room temperature, poured 180.00 g of crushed ice into the reaction solution, stirred thoroughly for 10 min, and then moved to a separatory funnel for static separation to obtain 184.20 g of the aqueous phase and 175.23 g of the organic phase; Add 2.17g nickel chloride, 1.43g zinc powder, 0.05g ammonium chloride, 19.83g triphenylphosphine and 200.00g toluene, stir and react at 55°C for 1.7h, filter the reaction solution after cooling down, and remove toluene by rotary evaporation , the organic phase was distilled under reduced pressure at 1.86kPa, and the fractions at 84° C. to 92° C. were collected to obtain 158.38 g of pure α-cyclic citral. The gas chromatography analysis selectivity was 99.80%, and the yi...

Embodiment 3

[0057] In the reaction kettle that has been dehydrated and deoxygenated, 84.12g of 1,3-pentadiene, 80.00g of prenaldehyde and 14.67g of aluminum trichloride were added under the protection of nitrogen, and the reaction was stirred at 100°C for 1.0h; the temperature dropped to room temperature, poured 180.00 g of crushed ice into the reaction solution, stirred thoroughly for 10 min, and then moved to a separatory funnel for static separation to obtain 184.10 g of the aqueous phase and 175.00 g of the organic phase; Add 2.17g nickel chloride, 1.43g zinc powder, 0.05g ammonium chloride, 19.80g triphenylphosphine and 200.00g toluene, stir and react at 55°C for 1.7h, filter the reaction solution after cooling down, and remove toluene by rotary evaporation , the organic phase was distilled under reduced pressure at 1.86kPa, and the fractions at 84°C to 92°C were collected to obtain 156.57g of pure α-cyclocitral, with a gas chromatography selectivity of 99.80% and a yield of 95.40%. ...

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Abstract

The invention discloses a synthesis method of alpha-cyclocitral. The method comprises the steps of (1) carrying out Diels-Alder reaction on 1,3-pentadiene and methylcrotonaldehyde under the catalysisof lewis acid to obtain a 2,6,6-trimethyl-3-cyclohexenyl formaldehyde crude product; (2) carrying out isomerization reaction on the 2,6,6-trimethyl-3-cyclohexenyl formaldehyde crude product obtained in step (1) under the catalysis of a catalyzer to generate an alpha-cyclocitral crude product. The method provided by the invention is easy to get reaction raw materials, mild in conditions, easy to control, free of generating byproducts, simple in process, favorable in industrial production, green and environmentally friendly.

Description

technical field [0001] The invention relates to a synthesis method of α-cyclocitral, in particular to a method for preparing α-cyclocitral through Diels-Alder and isomerization reactions, and belongs to the field of organic synthesis. Background technique [0002] Methyl ionone is a homologue of ionone, but its aroma and taste are better than ionone. Its beautiful and soft fragrance and good stability are favored by people. There are six isomers of methyl ionone, namely α-isomethyl ionone (α-ISO), β-isomethyl ionone (β-ISO), γ-isomethyl ionone (γ-ISO ), α-n-methyl ionone (α-N), β-n-methyl ionone (β-N), and γ-n-methyl ionone (γ-N), among which the aroma of α-ISO The most pure and pleasant, the price of commercially available methyl ionone fragrance also increases with the increase of α-ISO isomer content, such as the price of α-ISO content of 90wt% is obviously higher than that of 60wt% product s price. [0003] There are multiple synthetic routes of methyl ionone in the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/69C07C47/42C07C45/67
CPCC07C45/67C07C45/69C07C47/42
Inventor 谢硕信勇李晶崔娇英张静张永振
Owner WANHUA CHEM GRP CO LTD
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