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Synthesis method of deltalactone

A synthesis method and lactone technology, applied in the direction of organic chemistry, can solve the problems of three wastes in the process, expensive mercaptans, not easy to obtain, etc., and achieve the effect of reducing the discharge of three wastes

Inactive Publication Date: 2017-05-10
SHANGHAI WANXIANG FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

5-Oxo fatty aldehyde is not easy to get, SmI2 is expensive and bad smell of thiol
The process is cumbersome or the reagents used are expensive, and the three wastes in the process are serious

Method used

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  • Synthesis method of deltalactone
  • Synthesis method of deltalactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 250ml autoclave. Add 70ml of dioxane, 8.6g of 5-oxononanoic acid, 0.5g of 5% Ru / C; 4g of 3A molecular sieves are wrapped with glass cloth and placed in the solid feeding port tube. Replace air with nitrogen, replace nitrogen with hydrogen, fill with hydrogen to 10atm, and heat to 170°C with stirring. Continue to stir the reaction until the pressure drops no longer, about 12 hours. Cool to room temperature and filter off the catalyst. The solvent was recovered under normal pressure, 20ml of toluene was added to the material, washed with sodium bicarbonate solution, and washed with brine until neutral. The toluene was evaporated under reduced pressure by the water ring pump, and the 112-114°C / 260Pa fraction was collected by the oil pump vacuum distillation to obtain 5.36g of colorless liquid with a yield of 68.2%.

[0021] [MS: m / e(%): 29(34), 42(58), 55(43), 71(47), 99(100), 114(10), 152(2), 170(m+, 1 )].

Embodiment 2

[0023] In a 250ml autoclave, add 80ml of toluene, 10.7g of 5-oxododecanoic acid, 0.6g of 5% Pt / C respectively; 4g of 3A molecular sieves are wrapped with glass cloth and placed in the solid feed inlet tube. Replace air with nitrogen, replace nitrogen with hydrogen, fill with hydrogen to 12atm, and heat to 175°C with stirring. Continue to stir the reaction until the pressure drops no longer, about 16 hours. Cool to room temperature and filter off the catalyst. The material was washed with sodium bicarbonate solution and brine until neutral. The water ring pump decompressed to distill out the toluene, and the oil pump decompressed to collect the 130-132°C / 133Pa fraction to obtain 6.25g of viscous liquid with a yield of 63.1%.

[0024] [MS: m / e(%), 29(35), 41(82), 55(54), 71(52), 99(100), 84(11), 114(10), 180(2), 198 (m+, 2)].

Embodiment 3

[0026] 100ml autoclave. Electromagnetic stirring, oil bath; 40ml tetrahydrofuran, 6.02g 5-oxononanoic acid, 0.3g 5% Pt / C were added respectively; 2g of 3A molecular sieve was wrapped with glass cloth and placed on the temperature detection tube. Replace air with nitrogen, replace nitrogen with hydrogen, fill with hydrogen to 12atm, and heat to 160°C with stirring. Continue to stir the reaction until the pressure drops no longer, about 16 hours. Cool to room temperature and filter off the catalyst. The solvent was recovered under normal pressure, 20ml of toluene was added to the material, washed with sodium bicarbonate solution, and washed with brine until neutral. The toluene was evaporated under reduced pressure by the water ring pump, and the 112-114°C / 260Pa fraction was collected by the oil pump under reduced pressure distillation to obtain 3.36g of colorless liquid with a yield of 61%.

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Abstract

The invention discloses a synthesis method of deltalactone. The synthesis method is characterized by comprising the following steps: taking 5-oxo fatty acid as a starting raw material, and reacting under hydrogen pressure of 5atm to 30atm and at 120 DEG C to 180 DEG C in the presence of catalysts including Ru / C and the like; firstly, carrying out a hydrogenation reaction of carbonyl to obtain an intermediate product 5-hydroxyl fatty acid M1; meanwhile, carrying out intramolecular dehydration and esterification on M1 and carrying out a one-pot reaction to generate the deltalactone. A specific reaction formula is shown in the description, wherein R=CH3(CH2)n- and n is equal to 1 to 8.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing butyl lactone. Background technique [0002] Butyrolactone, also known as δ-lactone, naturally exists in peaches, coconuts, raspberries, asparagus, etc., and some also exist in milk, cream, and meat; most of them have creamy aroma and fruity aroma such as coconut. For example, butyl decanolide has a creamy aroma, coconut and peach-like fruity aroma; butyl undecalactone has a strong coconut aroma, coconut and tropical fruit-like aroma. It is mainly used in the formulation of food flavors, used to prepare creamy, coconut, peach, apricot and other fruity flavors, and can be used for flavoring margarine, soft drinks, ice cream, cold and baked foods, etc. Butyl caprolactone and butyl myristalactone are also used in daily chemical fragrances; since the real natural products cannot be extracted at a reasonable cost. Therefore, its synthesis has been widely va...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/30
CPCC07D309/30
Inventor 黄战鏖侯峰钱正刚裴继红张长征王勇卞余东
Owner SHANGHAI WANXIANG FLAVORS & FRAGRANCES