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Synthesis production process of 9-cyclohexadecylene lactone

A production process, the technology of enolactone, which is applied in the field of 9-cyclohexadecenolactone synthesis production process, can solve the problems of complex process and difficult control, and achieve the effect of reducing cost, simplifying operation, and reducing washing wastewater treatment process

Inactive Publication Date: 2009-04-29
INT FLAVORS & FRAGRANCES (HANGZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims at the blank of this kind of product in China and the shortcoming of complex process and difficult control of this kind of product abroad, and provides a kind of 9-cyclohexadecenolactone synthesis production process, which is suitable for simple and easy-to-control industrial production. One-pot synthesis production process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: 304g lacgaric acid and 1200g trimethyl orthoformate are dropped into 1 liter of reaction bottle. Heating to raise the temperature, recovering methanol and trimethyl orthoformate while raising the temperature, until the temperature reaches 180°C. Add 60g of sodium bicarbonate, control the pressure of the reaction system below -0.096MPa, continue to raise the temperature, and at the same time continuously add polyethylene glycol, and azeotropically distill the product at a temperature of 240°C until no product is distilled out. The evaporated product was rectified under reduced pressure to obtain 141 g of 9-cyclohexadecenolactone finished product, with a yield of 55.9% and a product content of 99.3%.

Embodiment 2

[0014] Embodiment 2: 304g lacgaric acid and 250g trimethyl orthoformate were dropped into a 1 liter reaction flask. Heating to raise the temperature, recovering methanol and trimethyl orthoformate while raising the temperature, until the temperature reaches 180°C. Add 10 g of potassium carbonate, control the pressure of the reaction system below -0.096 MPa, continue to raise the temperature, and at the same time continuously add glycerol, and azeotropically distill the product at a temperature of 240° C. until no product is distilled out. The evaporated product was rectified under reduced pressure to obtain 144 g of 9-cyclohexadecenolactone finished product, with a yield of 57.1% and a product content of 99.5%.

Embodiment 3

[0015] Embodiment 3: 304g lacgaric acid and 600g trimethyl orthoformate were dropped into a 1 liter reaction flask. Heating to raise the temperature, recovering methanol and trimethyl orthoformate while raising the temperature, until the temperature reaches 180°C. Add 30g of potassium bicarbonate, control the pressure of the reaction system below -0.096MPa, continue to raise the temperature while continuously adding ethylene glycol, and azeotropically distill the product at a temperature of 240°C until no product is distilled out. The evaporated product was rectified under reduced pressure to obtain 139 g of 9-cyclohexadecenolactone finished product, with a yield of 55.1% and a product content of 99.1%.

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Abstract

The invention relates to a production process for synthesizing 9-cyclo-hexadecylene lactone, which comprises the following steps: (1) putting aleuritic acid and trimethyl orthoformate into a reactor according to weight ratio of between 1 to 0.5 and 1 to 4, and heating up the mixture to raise the temperature to finish a deshydroxy polyreaction at a temperature of between 60 and 180 DEG C; and (2) adding a depolymerization catalyst into the mixture to perform a depolymerization cyclization reaction under vacuum condition at a temperature of between 180 and 240 DEG C to generate the product of the 9-cyclo-hexadecylene lactone which is distilled out through adding an azeotropic agent to perform continuous azeotropic azeotropy, and rectifying and refining the distilled product to obtain the finished product of the 9-cyclo-hexadecylene lactone. The production process has the advantages that catalysts such as proton acid, low-carbon alkyl anhydride and the like are not used so that the cost is reduced, washing wastewater treatment processes are reduced, and no environmental pollution is caused; and the complex reaction processes are finished through simple process steps in a reaction pot, so that the operation is greatly simplified, and the industrial production is achieved.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a synthesis and production process of 9-cyclohexadecenylactone used as a perfume. Background technique [0002] 9-Cyclohexadecenolactone, also known as oxetaneheptadecan-10-en-2-one, isoambride lactone, has not been reported in nature. It is a macrocyclic musk synthetic fragrance with a strong musk aroma accompanied by floral fragrance and long-lasting aroma. It is used as a fixative to prepare daily chemical essence, mainly used in high-end daily chemical essence formulations. It belongs to small tonnage and high value-added musk products. At present, there is no report of successful industrialized production in China. U.S. Patent 4014902 reports a technical synthesis route using 9,10,16-trihydroxypalmitic acid as a raw material. This technology is realized through three reaction steps. The first step is to synthesize dioxolane derivatives under the catalysis of protonic ...

Claims

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Application Information

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IPC IPC(8): C07D313/00
Inventor 吴宪宏裘永明邱伟峰朱翠兰袁金慧
Owner INT FLAVORS & FRAGRANCES (HANGZHOU) CO LTD
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