Preparation method capable of improving yield of alpha-isomer in ionone product

A technology of ionone and pseudo-ionone, which is applied in the field of preparation to increase the yield of α-isomers in ionone products, can solve the problems of the lack of optimal performance of ionone series products and poor aroma, and achieve the goal of preparing The method is simple and the effect of increasing output

Inactive Publication Date: 2017-06-13
广州百花香料股份有限公司
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  • Abstract
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Problems solved by technology

But no matter what method, it is always difficult to completely separate the α-ionone from the α-position, which makes the production of high-content α-ionone produce a large amount of ionone rear fractions with bad aroma (commonly known as ionone for soap, α-isomer 45-53%, β-isomer 32~40%), the benefits of the entire ionone series products will not be optimally reflected

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  • Preparation method capable of improving yield of alpha-isomer in ionone product
  • Preparation method capable of improving yield of alpha-isomer in ionone product
  • Preparation method capable of improving yield of alpha-isomer in ionone product

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preparation example Construction

[0026] The preparation method for improving the α-isomer output in the ionone product of the present invention comprises the following steps:

[0027] (1) Prepare pseudo-ionone products and ionone post-distillate products with a β-isomer content of more than 35%, for subsequent use;

[0028] (2), carry out the acidification cyclization reaction that inhibits the formation of β-isomers with the fraction after ionone: add acid solution and organic solvent accounting for 1 / 2 of the total catalyst acid solution in the container (reactor or flask), and then Add a certain amount of ionone fraction with the above-mentioned β-isomer content above 35% into the container and stir evenly, heat up to 35-80°C, and then start to add pseudo-ionone dropwise for 1-3 hours. After the dropwise addition is completed, add the remaining 1 / 2 of the acid solution, and continue to maintain the temperature and stir for 1-4 hours;

[0029] (3) After the reaction is completed and left to stand, slowly s...

Embodiment 1

[0039] Add 400g of benzene and 50g of phosphoric acid with a mass concentration of 85% into a 2000ml three-neck flask, stir well, then raise the temperature to 35-50°C, add 160g of ionone after the fraction (α-isomer content 50%, β-isomer content 35%), then start to drop 400g of pseudo-ionone, and control the dropping time for 1.5-3 hours. After the drop of pseudo-ionone is completed, add the remaining 50g of phosphoric acid; then raise the temperature to 50~55℃ to keep the reaction for 2- After 3 hours, follow the reaction process by chromatography until the PI content is ≤2%, stop stirring, and let stand to separate layers. After standing still, slowly separate the viscous acid solution in the lower layer (the acid solution is weighed, and it can be recycled after adding a small amount of fresh to a sufficient amount in the next batch). The upper organic phase is washed with soda water and brine until it is neutral. After recovering benzene, vacuum distillation is carried ou...

Embodiment 2

[0042] Add 400g of toluene and 100g of phosphoric acid with a mass concentration of 85% into a 2000ml three-necked flask, stir evenly, then raise the temperature to 35-50°C, add 160g of the ionone for soap obtained in the above example (the content of α-isomer is 53%, the content of β- Isomer content is about 35%), then start to drop 400g of pseudo-ionone, control the dropping time for 1.5-3 hours, after the addition of pseudo-ionone is completed, add the remaining 100g of phosphoric acid; Keep the reaction at ℃ for 2-3 hours, follow the reaction process by chromatography until the PI content is ≤2%, stop stirring, and let it stand for stratification. After standing still, slowly separate the viscous acid solution in the lower layer (the acid solution is weighed, and it can be recycled after adding a small amount of fresh to a sufficient amount in the next batch). The upper organic phase was washed with soda water and brine until it was neutral. After recovering the toluene, v...

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Abstract

The invention discloses a preparation method capable of improving yield of an alpha-isomer in an ionone product. The method comprises the following steps of: 1, preparing a spurious ionone product and an ionone after-cut product with beta-isomer content of 35% or more; 2, adding acid solution and an organic solvent, of which a quantity occupies for half of a total quantity of catalyst acid solution, into a container, then adding the ionone after-cut product, uniformly stirring, heating to a temperature of 35 to 80 DEG C, dropwise adding the spurious ionone product, completing replenishment of the residual acid solution after finishing dropwise adding, and continuously keeping the temperature to stir for 1 to 4 hours; 3, after completing the reaction and standing, separating out viscous acid solution on the bottom layer, washing an organic phase on the upper layer to a neutral state, and after recovering the solvent, carrying out vacuum rectification to obtain a high-content alpha-ionone product with alpha-isomer content of 86% or more. According to the preparation method disclosed by the invention, yield of the alpha-isomer in the ionone product is effectively improved, and the preparation method is simple, economic, practical and suitable for industrial continuous production of high-content alpha-ionone.

Description

technical field [0001] The invention belongs to the field of spice chemistry, in particular to a preparation method for increasing the yield of α-isomers in ionone products. Background technique [0002] Ionone, its chemical name is: 4-(2,6,6-trimethyl-2-cycloocten-1-yl)-3-buten-2-one, the usual reaction products are α—, γ —, β—a mixture of three isomers. Commercial ionone usually refers to a mixture with an α-body (also called a-position) content of 68-72% and a β-body (also called a-position) content of 18-23%. Ionone is light yellow transparent liquid. The α body has an excellent and rich violet and floral aroma, with a little warm wood-like iris fragrance; boiling point 146-147°C (28 mm Hg), density 0.9298 g / cm3 (21°C); ionone is widely used in Various types of blended flavors, especially blended flavors that can be used for ionone, rose, citrus, but also for berry food flavors. High content of methionone is also often found in the formulations of various perfume frag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/21C07C45/67
CPCC07C45/67C07C49/21
Inventor 张建斌钟炼军吴习荧庄子翀姚菓
Owner 广州百花香料股份有限公司
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