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Method for synthesizing delta-dodecalactone

A technology of laurolactone and condensation, applied in chemical recovery, organic chemistry and other directions, can solve the problems of difficult industrialized production, cumbersome synthesis process, low yield, etc., and achieve the effects of improved purity, high reactivity, and easy method.

Inactive Publication Date: 2012-03-21
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] About the synthetic method of δ-laurolactone, there are many reports at home and abroad at present, according to its synthetic route, mainly contain 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-dodecanolide, the synthesis process of this method is cumbersome and the yield is low; the second is to carry out Dieckmann condensation with diethyl adipate, and then use anhydrous K 2 CO 3 React with n-bromoheptane in acetone, deacidify and oxidize to obtain δ-dodecalactone. This method has reasonable cost, but the steps are long and the yield is not high, so it is difficult to apply to industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Condensation and dehydration:

[0038] Add the sodium hydroxide solution with a concentration of 0.5% or 1% or 5.0% or 10% or 20%, cyclopentanone and a phase transfer catalyst into the three-necked flask, at 10°C or 20°C or 30°C or 40°C or 50°C Add n-heptanal dropwise at ℃ for 1h or 2h or 3h or 4h, and ensure that the mass ratio of cyclopentanone to n-heptanal is 1:1 or 1.2:1 or 1.5:1 or 1.8 :1 or 2:1 or 3:1 or 4:1 or 5:1. After the dropwise addition, keep the system at 10°C or 20°C or 30°C or 40°C or 50°C, and track the end of the reaction by TLC. Neutralize with acetic acid to make the pH of the mixture = 5 or 6, cool and stand to separate layers, extract the water layer with an extractant, combine the extract with the organic phase, and use 5% NaHCO 3 Wash twice with saturated NaC aqueous solution, transfer to a flask with an oil-water separator, add 10ml or 20ml or 30ml or 40ml or 50ml of toluene, heat to 90°C or 92 or 94°C or 96°C or 98°C or 100°C and stir un...

Embodiment 2

[0046] (1) Condensation and dehydration:

[0047] Add 0.5% or 1% or 5.0% sodium hydroxide solution, 25ml of cyclopentanone and phase transfer catalyst PEG-400 into the three-necked flask, slowly add 20.90ml dropwise at 10°C or 20°C or 30°C The n-heptanal, the time is 1h or 2h, and the amount ratio of cyclopentanone and n-heptanal added is 1:1 or 1.2:1 or 1.5:1 or 1.8:1. After the dropwise addition, keep the system at 10°C or 20°C or 30°C, and follow the end of the reaction by TLC. Neutralize with acetic acid to make the pH of the mixture = 5 or 6, cool and static to separate the layers, extract the aqueous layer with toluene, combine the extract with the organic phase, and successively wash with 5% NaHCO 3 Wash twice with saturated NaCl aqueous solution, transfer to a flask with an oil-water separator, add 10ml or 20ml or 30ml of toluene, heat to 90°C or 92°C or 94°C or 96°C or 98°C or 100°C and stir until no more Moisture out. After cooling, and then through saturated NaCl...

Embodiment example 3

[0058] (1) Condensation and dehydration

[0059] The concentration is 1% or 5.0% or 10% sodium hydroxide solution, cyclopentanone and phase transfer catalyst are added in the there-necked flask, and n-heptanal is slowly added dropwise at 20°C or 30°C or 40°C to ensure that the added The mass ratio of cyclopentanone to n-heptanal is 1.5:1 or 1.8:1 or 2:1 or 3:1. After the dropwise addition, keep the system at 20° C. or 30° C. or 40° C. or 50° C., and track the end of the reaction by TLC. Neutralize with acetic acid to make the pH of the mixture = 5 or 6, cool and static to separate the layers, extract the aqueous layer with cyclohexane, combine the extract with the organic phase, and successively wash with 5% NaHCO 3 Wash twice with saturated NaCl aqueous solution, transfer to a flask with an oil-water separator, add 20ml or 30ml or 40ml of toluene, heat at 90°C or 92°C or 94°C or 96°C or 98°C or 100°C and stir until no more Moisture out. After cooling, and then through satu...

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Abstract

The present invention discloses a method for synthesizing delta-dodecalactone, which comprises the following steps: (1) condensating and dehydrating: under the present of a phase-transfer catalyst under an alkaline condition, causing aldol condensation between cyclopentanone and heptanal, and dehydrating for generating 2-heptene cyclopentanone under the function of an acid catalyst; (2) hydrogenating: causing the 2-heptene cyclopentanone to hydrogenate under the presence of ion exchange resin for obtaining 2- heptyl cyclopentanone; (3) oxidizing: causing a Baeyer-Villiger oxidation reaction between the 2- heptyl cyclopentanone and hydrogen peroxide for obtaining a crude product; and (4) refining: obtaining a pure product from the crude product through molecular distillation. The method for synthesizing delta-dodecalactone has the following advantages: easy method application, simple operation, higher yield, and easy available raw material. The yield of the target product delta-dodecalactone is improved, and the purity is greatly improved. The product purity is larger than 99.0%, and the yield is above 80%. The catalyst used in the method has the characteristics such as capability of being used repeatedly.

Description

technical field [0001] The invention relates to the technical field of synthesis of δ-lactone, and more specifically relates to a method for synthesizing δ-laurolactone. The product δ-laurolactone of the present invention has a strong fat aroma of fresh fruit, and as a new lactone fragrance, it is widely used in the preparation of strong floral fragrances such as aldehyde-scented perfumes, gardenia and tuberose. In addition, because natural animal butter contains a lot of fat, excessive inhalation can easily cause cardiovascular disease. Therefore, add butter flavor to vegetable oil as margarine instead of natural cream, and δ-laurolactone is the main component of cream flavor. Therefore, the synthesis of δ-laurolactone is of great significance in the food industry. Background technique [0002] Lactone is an important organic compound and intermediate, and has broad application prospects in the fields of fragrance, flavor and drug synthesis. For example, γ- and δ-lactone...

Claims

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Application Information

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IPC IPC(8): C07D309/30
CPCY02P20/584
Inventor 李广学卜佳赵明珠李家鸣姜丰储杨詹华露
Owner ANHUI UNIV OF SCI & TECH
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