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Synthesis process of natural delta-decalactone

A synthesis process and decanolide technology, applied in the field of food additives, can solve the problems of complicated synthesis process, low yield, low yield and the like, and achieve the effects of easy availability of raw materials, abundant sources and high yield

Active Publication Date: 2021-12-31
安徽华业香料合肥有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Regarding the synthetic method of δ-lactone, there are mainly the following two methods in combination: the one is to react with cyclohexanedione and brominated n-hexane, and then oxidize ring-opening, reduction and cyclization to obtain δ-decalactone. The synthetic process of method is loaded down with trivial details, and productive rate is lower; The other is to carry out Dieckmann condensation with diethyl glutarate, and then use anhydrous K 2 CO 3 React with n-bromoheptane in acetone, deacidify and oxidize to obtain δ-decalactone. This method has reasonable cost, but the steps are long and the yield is not high.

Method used

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  • Synthesis process of natural delta-decalactone
  • Synthesis process of natural delta-decalactone
  • Synthesis process of natural delta-decalactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Build a 2000mL synthetic fine-separation integrated device with a constant temperature magnetic stirrer, rectification device, and tail gas absorption device, add 800g of n-pentanol and 1035g of hydrochloric acid solution with a mass fraction of 32% into the reaction kettle, start stirring, raise the temperature to 85°C, and keep warm React for 2 hours; continue to heat up to 94°C, keep warm for 20 hours, and the crude product is extracted at a reflux ratio of 3 / 5 during the reaction; after the reaction is completed, post-processing is carried out to obtain intermediate 1; the weight is 350g, and the GC content is 99.56%.

[0034] The aftertreatment process is as follows: the crude product at the bottom of the kettle is layered, wherein the oil phase is a mixture of amyl alcohol and pentyl ether, and the water phase is dilute hydrochloric acid. Add 5% sodium bicarbonate solution to the crude product to adjust the pH value to 7; Add concentrated sulfuric acid, the amount ...

Embodiment 2

[0036] Build a 2000mL synthetic fine-separation integrated device with a constant temperature magnetic stirrer, rectification device, and tail gas absorption device, add 800g of n-pentanol and 1035g of hydrochloric acid solution with a mass fraction of 32% into the reaction kettle, start stirring, raise the temperature to 90°C, and keep warm React for 2 hours; continue to heat up to 98°C, keep warm for 20 hours, and the crude product is extracted at a reflux ratio of 3 / 5 during the reaction; after the reaction is completed, post-processing is carried out to obtain intermediate 1; the weight is 352g, and the GC content is 99.55%.

[0037] The aftertreatment process is as follows: the crude product at the bottom of the kettle is layered, wherein the oil phase is a mixture of amyl alcohol and pentyl ether, and the water phase is dilute hydrochloric acid. Add 5% sodium bicarbonate solution to the crude product to adjust the pH value to 8; Add concentrated sulfuric acid, the amount ...

Embodiment 3

[0039]Build a 1000mL synthetic reaction kettle with a constant temperature magnetic stirrer, a spherical condenser, and a dropping device. Under nitrogen protection, add 57g of magnesium chips, 50g of tetrahydrofuran and 5g of bromopentane into the kettle, maintain the temperature at 20°C, and stir for 10min To obtain the Grignard reagent, keep the reaction kettle at 60°C, add 120g of intermediate 1 dropwise to the Grignard reagent, and the dropwise addition ends in 2h. After maintaining the temperature and continuing the reaction for 1h, cool down to 20°C, then add 100g of furfural dropwise, and the dropwise addition ends in 2h. The temperature was maintained and the reaction was continued for 1 h; after the reaction, after-treatment was carried out to obtain intermediate 2; the weight was 170 g, and the GC content was 88.33%.

[0040] The post-treatment process is as follows: raise the temperature of the reaction solution under normal pressure to recover 1 / 3 of tetrahydrofura...

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Abstract

The invention relates to a synthesis process of natural delta-decalactone, and belongs to the technical field of food additives, and the natural delta-decalactone is obtained by taking furfural and n-amyl alcohol as raw materials through chlorination, Grignard coupling, Piancatelli rearrangement, hydrogenation and oxidation. The purity of the delta-decalactone prepared in the synthesis process of the natural delta-decalactone can reach 98% or above, the natural degree detected by isotope mass spectrometry C14 is 95% or above, and the problems that the synthesis route of the delta-decalactone is complex and the yield is low are solved; and the experimental method is simple, convenient and feasible, the reaction condition is mild, the experimental condition is easy to realize and control, and the method has the characteristics that the raw materials are easy to obtain and rich in source, the yield is relatively high, the used catalyst can be repeatedly used and the like.

Description

technical field [0001] The invention belongs to the technical field of food additives, and in particular relates to a synthesis process of natural δ-decalactone. Background technique [0002] Natural δ-decalactone is an important organic compound and intermediate, butyrolactone series compounds are important food flavors with milky, coconut, fruity and other aromas, widely used in candy, soft drinks, ice cream, baking food. In margarine, cakes, feed and other products. Among them, butyl decalactone and butyl laurolactone are the most important. GB2760 stipulates that it is allowed to use food spices. Used in food flavors such as almonds, cherries, butter, cream, etc., and also used in tobacco flavors. [0003] Regarding the synthetic method of δ-lactone, there are mainly the following two methods in combination: the one is to react with cyclohexanedione and brominated n-hexane, and then oxidize ring-opening, reduction and cyclization to obtain δ-decalactone. The synthet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/30
CPCC07D309/30Y02P20/584
Inventor 张政王天义梁立冬汪洋
Owner 安徽华业香料合肥有限公司
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