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Synthesis process of whisky lactone

A technology of whisky lactone and synthesis process, applied in the direction of organic chemistry and the like, can solve the problems of difficulty in recovery, low conversion rate of n-valeraldehyde, etc., and achieve the effects of improving economic benefits, reducing the difficulty of wastewater treatment, and reducing energy consumption and input cost.

Active Publication Date: 2019-11-12
ANHUI HYEA AROMAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The molar ratio of n-valeraldehyde to crotonic acid as the reaction raw material of this patent is 4:1, and the n-valeraldehyde is far in excess. However, under acidic medium conditions, n-valeraldehyde is unstable, so the conversion rate of n-valeraldehyde is low and recovery is difficult.

Method used

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  • Synthesis process of whisky lactone
  • Synthesis process of whisky lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1) Synthesis of Ketoesters

[0027] In a 1000mL three-necked flask equipped with a thermometer, a stirrer, and a dropping funnel, add 184g (4mol) of ethanol and 114g (1mol) of ethyl crotonate, mix the above materials evenly, and heat up to reflux, and then pour the mixture through the dropping funnel Add 86 g (1 mol) of n-valeraldehyde (1 mol) and 92 g (2 mol) of ethanol dropwise into a three-necked flask, and stir while dropping. After 2 hours, the dropwise addition is completed, and then continue stirring to react the above reactants at 80° C. for 2 hours, and collect 138 g of distillate. After the reaction finished, the reaction crude product weighed 338g, detected by GC, and recorded that the main fraction was ketoester, and the content was 92%; ethyl crotonate had 6% unreacted (after deducting the solvent ethanol peak).

[0028] 2) Synthesis of whiskey lactone

[0029] In an autoclave with a stirring bar, add 338 g of crude keto ester and 6 g of a Pd / C catalyst wi...

Embodiment 2

[0031] 1) Synthesis of Ketoesters

[0032] In a 1000mL three-necked flask equipped with a thermometer, a stirrer, and a dropping funnel, add 230g (5mol) of ethanol and 114g (1mol) of ethyl crotonate, mix the above materials evenly, and heat up to reflux, and then pour the mixture through the dropping funnel. Add 86 g (1 mol) of n-valeraldehyde and 46 g (1 mol) of ethanol dropwise into a three-necked flask, and stir while dropping. After 2 hours, the dropwise addition is completed, and then continue to stir to react the above reactants at 80° C. for 2 hours, and collect 132 g of distillate. After the reaction finished, the reaction crude product weighed 342g, detected by GC, and recorded that the main fraction was ketoester, and the content was 89.2%; ethyl crotonate had 8% unreacted (after deducting the solvent ethanol peak).

[0033] 2) Synthesis of whiskey lactone

[0034] Add 342g of ketoester crude product and 6g of mass fraction 5% Pd / C catalyst in an autoclave with a st...

Embodiment 3

[0036] 1) Synthesis of Ketoesters

[0037] In a 1000mL three-necked flask equipped with a thermometer, a stirrer, and a dropping funnel, add 300g (5mol) of propanol and 128g (1mol) of propyl crotonate, mix the above materials evenly, heat up to reflux, and then pass through the dropping funnel Add 86g (1mol) of n-valeraldehyde and 60g (1mol) of propanol dropwise to the three-necked flask, and stir while dropping. After 2h, the dropwise addition is completed, and then continue to stir, so that the above reactants are reacted at 102°C for 2h, and the distillate is collected. 180g. After the reaction finished, the reaction crude product weighed 480g, and GC was detected, and the main fraction was recorded as ketoester, and the content was 93%; 4% of propyl crotonate was unreacted (after deducting the peak of solvent propanol).

[0038] 2) Synthesis of whiskey lactone

[0039] In an autoclave with a stirring bar, add 480 g of crude keto ester and 10 g of a 5% Pd / C catalyst by ma...

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Abstract

The invention discloses a synthesis process of whisky lactone, and relates to the technical field of organic synthesis. According to the method, n-valeraldehyde and crotonate are used as reaction rawmaterials, alcohol is used as a reaction solvent, and keto ester is prepared through an addition reaction; and hydrogenation reaction is carried out under the action of a catalyst to obtain the whiskylactone. In the method, the keto ester can be prepared by taking the n-valeraldehyde and the crotonate as reaction raw materials without an initiator and a cocatalyst, so that the problem that the conversion rate of the n-valeraldehyde is reduced due to instability of the n-valeraldehyde when an acidic medium is taken as the cocatalyst is avoided.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis process of whiskey lactone. Background technique: [0002] Whiskey lactone (Whiskey lactone) naturally exists in whiskey and oak. It has a strong and long-lasting coconut and creamy aroma. It is mainly used in food, alcohol and tobacco flavor formulations. It is a high-end and precious spice. [0003] Patent CN200610047696.9 discloses a preparation method of whiskey lactone, using crotonic acid and n-valeraldehyde as starting materials, reacting under the action of initiator and cocatalyst, then washing and flashing to obtain keto acid, and then Catalytic hydrogenation and distillation to obtain whiskey lactone. [0004] [0005] The molar ratio of n-valeraldehyde to crotonic acid as the reaction raw material of this patent is 4:1, and the n-valeraldehyde is far in excess. However, under acidic medium conditions, n-valeraldehyde is unstable, so the conv...

Claims

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Application Information

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IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 张政储新宇汪洋
Owner ANHUI HYEA AROMAS
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