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Method for synthesizing (E)-2-hexenoic acid

A synthesis method, a technology of hexenoic acid, applied in chemical instruments and methods, preparation of carboxylic acids by ozone oxidation, organic compounds/hydrides/coordination complex catalysts, etc., can solve the use of toxic solvents, harsh reaction conditions, and side reactions. Serious problems, to achieve the effect of less side reactions, easy availability of raw materials and low prices

Inactive Publication Date: 2012-07-04
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The object of the present invention is to provide a kind of mild reaction conditions, few side reactions, A new environmentally-friendly method for high-yield, aqueous-phase synthesis of (E)-2-hexenoic acid

Method used

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  • Method for synthesizing (E)-2-hexenoic acid
  • Method for synthesizing (E)-2-hexenoic acid
  • Method for synthesizing (E)-2-hexenoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 10 milliliters of water, 5.0 millimoles of diethyl malonate, 5.0 millimoles of n-butyraldehyde and 0.15 millimoles of catalyst TBAB were added to the reaction flask equipped with a reflux condenser and agitator, and the reaction mixture was stirred at 25° C. for 12 hours. Afterwards, the temperature was raised to 60°C, and the stirring was continued for 6.0 hours, then the temperature was raised to 90°C, and the stirring was continued for 2 hours, then a 10% sodium hydroxide solution was added, stirred and refluxed for 0.5 hours, and then 10% hydrochloric acid was added to acidify , stirred and refluxed for 0.5 hour, stopped the reaction, distilled under reduced pressure, and dried in vacuum to obtain 0.485 g of (E)-2-hexenoic acid with a yield of 85%.

[0021] The reaction equation is as follows:

[0022]

[0023] Data characterization of hexenoic acid:

[0024] Mp: 125~127℃ / 2.66KPa

[0025] 1 H NMR (500MHz, CDCl 3 , 25°C) δ=0.87(3H), 1.41(2H), 2.14(2H), 5.76(2H...

Embodiment 2

[0030] The consumption of n-butyraldehyde is 0.48 mmol, and other operating conditions are all the same as in Example 1, and the yield of (E)-2-hexenoic acid is 82%, 124~125°C / 2.66KPa.

Embodiment 3

[0032] Except that the consumption of n-butyraldehyde was 0.52 mmol, other operating conditions were the same as in Example 1, and the yield of (E)-2-hexenoic acid was 80%, 125~126°C / 2.66KPa.

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Abstract

The invention provides a method for synthesizing (E)-2-hexenoic acid. The method comprises the following steps: using ethyl malonate as a raw material, and performing Knovenagel reaction, hydrolysis and decarboxylation on the ethyl malonate in a water phase to synthesize the (E)-2-hexenoic acid. Aiming at problems of strict reaction condition, serious side reaction, low yield and usage of a toxicreagent in the prior method for synthesizing the (E)-2-hexenoic acid, the method uses water as a reaction medium to realize clean and environment-friendly production without pollution, and has accessible raw materials with low cost, mild reaction condition, simple operation and easy industrialization. The synthesis method has few side reactions, and yield up to 75 to 85 percent.

Description

technical field [0001] The invention provides a method for synthesizing (E)-2-hexenoic acid. Background technique [0002] (E)-2-hexenoic acid, commonly known as butylene acetic acid, has a special oily aroma. It is a carboxylic acid safe edible synthetic flavor announced by the FDA. The FEMA number is 3169. [0003] - The edible synthetic spices allowed to be used in Appendix 86 are sold under the English name of trans-2-Hexenoic acid (trans-2-hexenoic acid), and its structural formula is as follows: [0004] [0005] (E)-2-hexenoic acid can be used in the formulation of apple, banana, and caramel flavors, and it can also be used in the formulation of flavors for food, beverages and daily chemical products with fruity aroma. (E)-2-hexenoic acid has a sweet berry aroma with a long-lasting smell, and is generally considered suitable for the formulation of food flavors. In recent years, because the fruity aroma has become more and more popular, the market demand for (E)-2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/03C07C51/38B01J31/02A23L1/226A23L27/20
Inventor 董德文梁永久周扬
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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