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Method for synthesis of gamma-nonyl lactone

A technology of nonolactone and methyl acrylate, applied in the field of synthesizing γ-nonolactone, can solve the problems of reducing reaction rate and product yield, unfavorable reaction process, difficulty in removing methanol and tert-butanol, etc., and achieves increasing feeding speed. and reaction speed, improve product yield and reduce production cost

Inactive Publication Date: 2012-08-01
XIAMEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent CN101735180 reports the use of tert-butyl peroxybenzoate as an initiator, n-hexanol and acrylate as raw materials, and a method for synthesizing γ-nonalactone by free radical addition reaction, but is verified according to the method reported in this Chinese patent, It was found that the yield was also lower
Chinese patent CN101973968 also reports using n-hexanol and acrylate as raw materials to synthesize gamma-nonanolide by free radical addition reaction under high pressure. Product yield, but the method reported in this patent requires high pressure conditions, and the production process is relatively complicated, so the method equipment cost and operating cost reported in this patent are also relatively high
[0005] After analysis, it is found that using n-hexanol and acrylate as raw materials to prepare the target product through free radical addition reaction is an ideal method for preparing γ-nonalactone, but the by-product methanol and tert-butanol generated in the reaction process are difficult to obtain. Bleeding from the system, thereby reducing the reaction rate and product yield
This is because the reaction is carried out at a higher temperature (170-190° C.), and the reaction temperature is higher than the boiling point of the raw material methyl acrylate, di-tert-butyl peroxide and by-product tert-butanol and methanol. It is very difficult for the distillation unit to remove methanol and tert-butanol. According to the reaction mechanism, the existence of by-product methanol and tert-butanol will be very unfavorable to the reaction process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Add 150mL n-hexanol and 3.0g zinc bromide in a 500mL three-necked flask equipped with a constant pressure dropping funnel, thermometer, alcohol removal device and condenser, add 25mL water and 10mL n-hexanol in the alcohol removal device. Heat and stir with a heat-collecting magnetic stirrer. After the temperature stabilizes to 180°C, start to add a mixture consisting of 50 mL of n-hexanol, 5 mL of di-tert-butyl peroxide and 23.5 mL of methyl acrylate dropwise at a rate of 5 mL / h. After the dropwise addition of the raw material mixture was completed, the temperature was kept at 180° C., and the reaction was terminated after reflux for 12 hours. The yield was 70.3%.

[0017] The nuclear magnetic analysis result of embodiment 1:

[0018] 1 H-NMR (400MHz, CDCl 3 ), δ: 4.53-4.44(m, 1H), 2.52(dd, J=9.5, 6.9Hz, 2H), 2.33-2.25(m, 1H), 1.87-1.77(m, 1H), 1.75-1.52(m , 2H), 1.48-1.25(m, 6H), 0.92-0.86(m, 3H). 13 C-NMR (100MHz, CDCl 3 ), δ: 177.39, 81.11, 35.52, 31...

Embodiment 2

[0019] Example 2: (comparative test, reactor is not equipped with alcohol removal device) 150mL n-hexanol and 3.0g zinc bromide were added in a 500mL three-necked flask equipped with a constant pressure dropping funnel, a thermometer and a condenser. Heat and stir with a heat-collecting magnetic stirrer. After the temperature stabilizes to 180°C, start to add a mixture consisting of 50 mL of n-hexanol, 5 mL of di-tert-butyl peroxide and 23.5 mL of methyl acrylate dropwise at a rate of 5 mL / h. After the dropwise addition of the raw material mixture was completed, the temperature was kept at 180° C., and the reaction was completed after refluxing for 12 hours, and the yield was 47.7%.

[0020] The nuclear magnetic analysis result of embodiment 2:

[0021] 1 H-NMR (400MHz, CDCl 3 ), δ: 4.53-4.44(m, 1H), 2.52(dd, J=9.5, 6.9Hz, 2H), 2.33-2.25(m, 1H), 1.87-1.77(m, 1H), 1.75-1.52(m , 2H), 1.48-1.25(m, 6H), 0.92-0.86(m, 3H). 13 C-NMR (100MHz, CDCl 3 ), δ: 177.39, 81.11, 35.52, 31...

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Abstract

The invention discloses a method for synthesis of gamma-nonyl lactone, and relates to gamma-nonyl lactone. Three fourths of hexanol and catalyst by consumption are added into a reactor equipped with an alcohol removal device and are heated, residual hexanol, initiator, and methyl acrylate are added into the reactor after being mixed to obtain the gamma-nonyl lactone. The defects in the prior art are overcome via matching with the alcohol removal device in the reactor and adding a certain amount of water and hexanol into the alcohol removal device, thus methanol and tertbutyl alcohol generated in the reaction process are easy to remove from a system, the feeding speed and reaction speed are increased, side reactions are prevented from occurring as much as possible, and the yield of the gamma-nonyl lactone is increased. Additionally, the generated methanol can be recycled, and thus the production cost can be reduced.

Description

technical field [0001] The invention relates to a gamma-nonanolide, in particular to a new method for synthesizing gamma-nonanolide. Background technique [0002] γ-nonanolide is also known as γ-pentyl-butyrolactone, and its trade name is coconut aldehyde or octadecaldehyde. It has a strong aroma of coconut, cream, star anise, licorice and peach, etc. It is a commonly used lactone One of the spices, usually used in the preparation of flavors such as coconut, milk and cream. [0003] At present, the γ-nonanolide fragrances on the market are mainly derived from chemical synthesis. There are many chemical synthesis methods for γ-nonanolide. The more traditional methods are as follows: 7-hydroxy nonanoic acid and sulfuric acid are used as raw materials to prepare γ-nonanolide; α-heptene and acetic acid are used as raw materials, and cerium , vanadium and other high-valent acetate or manganese acetate (+3 valence) as oxidant to prepare γ-nonanolide; use β, γ-nonenoic acid as ra...

Claims

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Application Information

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IPC IPC(8): C07D307/33
Inventor 吐松董万方百发
Owner XIAMEN UNIV
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