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A kind of synthetic method of trans 2-methyl-2-pentenoic acid

A synthesis method and technology of pentenoic acid, which are applied to the reaction of carbon monoxide to prepare carboxylic acid, organic chemical methods, chemical instruments and methods, etc., can solve the problems of insignificant industrial application benefits, many reaction steps, poor selectivity, etc., and achieve atomic utilization. The effect of good efficiency, low production cost and less three wastes

Active Publication Date: 2022-07-15
SHANDONG NHU PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 2. Using 2-methylpentanoic acid as the starting material, strawberry acid was synthesized through 5 steps of α-bromo, esterification, hydrolysis dehydration, saponification and acidification. This method has many reaction steps and low yield. Industrial Application benefits are not obvious
[0010] 4. Propionaldehyde and butanone are condensed under the catalysis of sulfuric acid to obtain 3-methyl-3-hexen-2-one; afterward, strawberry acid is obtained through haloform reaction, and the yield of this method is not high
In these patents, the reaction adopts palladium salt as a catalyst, but what is mainly obtained is a mixture of 2-, 3- and 4-pentenoic acid, and the selectivity is poor

Method used

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  • A kind of synthetic method of trans 2-methyl-2-pentenoic acid
  • A kind of synthetic method of trans 2-methyl-2-pentenoic acid
  • A kind of synthetic method of trans 2-methyl-2-pentenoic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1-25

[0063] Catalyst 1 (rhodium salt and ligand) was added to the autoclave, solvent was added and stirred to coordinate and dissolve the rhodium salt and ligand, and then piperylene and water were added. The reaction kettle was closed, and the air in the kettle was first replaced with nitrogen three times, followed by carbon monoxide three times, heated to the set temperature, and supplemented with carbon monoxide to the set pressure. The reaction is started, the end of the reaction is detected in the gas phase, and then the reaction solution is moved to a rectifying tower for rectification under reduced pressure to obtain cis-trans isomers of 2-methyl-3-pentenoic acid. The specific experimental results are shown in Table 1 below.

[0064] Table 1 Step (1) experimental results

[0065]

[0066]

[0067] According to the results in the above table, we can draw the following conclusions: Comparative Examples 1-4, the rhodium salt is preferably Rh 2 (CO) 4 Cl 2 ; Comparativ...

Embodiment 26-36

[0069] A certain amount of catalyst 2 (zinc chloride / acetic acid solution) is added to the cis-trans isomer of 2-methyl-3-pentenoic acid obtained in step (1), and the temperature is raised to a set temperature to carry out isomerization reaction. The end point of the reaction was detected by the gas phase. After the reaction was completed, the reaction was washed twice with distilled water, and the upper oil phase was obtained by liquid separation. Subsequently, the reaction solution was moved to a rectifying tower for vacuum distillation and separation to obtain trans-strawberry acid. The specific experimental results are shown in Table 2 below.

[0070] Table 2 Step (2) experimental results

[0071]

[0072] According to the results in the above table, we can draw the following conclusions: the feeding amount of the zinc chloride / acetic acid catalyst is preferably 8-13% (mass ratio to the cis-trans isomer), and the zinc chloride / acetic acid solution is chlorinated The ma...

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Abstract

The present invention adopts the Reppe synthesis method to prepare strawberry acid. First, piperylene, carbon monoxide and water are used as raw materials, and noble metal rhodium salt and organic phosphine ligand are used as catalysts to obtain the cis-trans iso-iso of 2-methyl-3-pentenoic acid. The intermediate product is then isomerized to generate trans-2-methyl-2-pentenoic acid, i.e. trans-strawberry acid.

Description

technical field [0001] The invention relates to a reaction for synthesizing acid by using olefin as a raw material, in particular to a method for synthesizing trans-2-methyl 2-pentenoic acid, which belongs to the fields of fine chemicals and flavors and fragrances. Background technique [0002] Strawberry acid, also known as 2-methyl-2-pentenoic acid, naturally exists in strawberries, mostly in trans form. With a sweet, berry-like aroma and acidity, the flavour is full-bodied and persistent. It is mainly used for the preparation of edible strawberry, hawthorn, cheese, raspberry and tropical fruit flavors; it can also be used to manufacture citrus flavored food flavors, which can be directly used in beverage and food processing. In addition to being used in food flavors, strawberry acid is also used in the formulation of daily chemical flavors. [0003] At present, 2-methyl-2-pentenoic acid mainly has 6 kinds of synthesis methods: [0004] 1. Using 2-pentanone as the start...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/14C07C51/353C07C57/03B01J31/22B01J31/20B01J31/18B01J31/24
CPCC07C51/14C07C51/353B01J31/2213B01J31/20B01J31/1845B01J31/2414C07B2200/09B01J2531/822B01J2531/0238B01J2531/0288B01J2231/321C07C57/03
Inventor 李守垒马啸于明董士琪王勇郝广果尹婵
Owner SHANDONG NHU PHARMA
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