Method for synthesizing (E)-2-hexenoic acid

A synthesis method and technology of hexenoic acid, applied in chemical instruments and methods, preparation of carboxylic acid by ozone oxidation, organic compound/hydride/coordination complex catalyst, etc., can solve harsh reaction conditions, use of toxic solvents, side reactions Serious problems, to achieve the effect of less side reactions, mild reaction conditions and low price

Inactive Publication Date: 2009-12-16
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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

[0019] Add 10 ml of water, 5.0 mmoles of diethyl malonate, 5.0 mmoles of n-butyraldehyde and 0.15 mmoles of catalyst TBAB to a reaction flask equipped with a reflux condenser and a stirrer. The reaction mixture was stirred at 25°C for 12 hours. After that, the temperature was raised to 60°C, and the stirring was continued for 6.0 hours, and then the temperature was raised to 90°C, and the stirring was continued for 2 hours, then 10% by mass sodium hydroxide solution was added, stirred and refluxed for 0.5 hours, and then 10% by mass hydrochloric acid was added to acidify , Stirring and refluxing for 0.5 hours, stopping the reaction, distillation under reduced pressure, and vacuum drying to obtain 0.485 g of (E)-2-hexenoic acid with a yield of 85%.

[0020] The reaction equation is as follows:

[0021]

[0022] Data characterization of hexenoic acid:

[0023] Mp: 125~127℃ / 2.66KPa

[0024] 1 H NMR(500MHz, CDCl 3 , 25℃)δ=0.87(3H), 1.41(2H), 2.14(2H), 5.76(2H), 6.80(1H), 12.14(1H). ...

Embodiment 2

[0029] The dosage of n-butyraldehyde was 0.48 mmol, and other operating conditions were the same as in Example 1. The yield of (E)-2-hexenoic acid was 82%, 124-125°C / 2.66KPa.

Embodiment 3

[0031] Except that the dosage of n-butyraldehyde is 0.52 mmol, other operating conditions are the same as in Example 1, and the yield of (E)-2-hexenoic acid is 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 toxic reagent 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 present invention provides a method for synthesizing (E)-2-hexenoic acid. Background technique [0002] (E)-2-Hexenoic acid, commonly known as butenylidene acetic acid, has a special oily aroma. It is a carboxylic acid safe edible synthetic fragrance published by the FDA. The FEMA number is 3169. It is also in the appendix of the Chinese Food Additives Standard GB2760-86. The permitted edible synthetic fragrance is sold under the English name of trans-2-Hexenoic acid (trans-2-hexenoic acid), and its structural formula is as follows: [0003] [0004] (E)-2-hexenoic acid can be used in the preparation of apple, banana, caramel flavors, and can be used in the preparation of fruity foods, beverages and daily chemical products. (E)-2-hexenoic acid has a sweet berry aroma and a long lasting odor, and is generally considered suitable for the preparation of edible flavors. In recent years, since the fruit aroma has become more and more popular, the market ha...

Claims

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Application Information

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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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