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Preparation method for purified 3-methyl-2-butenyl acetate

A technology of methyl and acetic acid, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, etc. It can solve the problems of many impurities, dissatisfaction, and wastewater treatment with amine compounds

Active Publication Date: 2007-03-14
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the former method has a problem in treating waste water due to the use of an excessive amount of amine compound
The latter method has low yield and many impurities, or there are problems with catalyst availability and its handling
Therefore, either method is industrially unsatisfactory

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 (reaction steps)

[0036] Under a nitrogen atmosphere, 140.6g (1.60mol) of 3-methyl-2-buten-1-ol (content: 98% by weight) and 16.2g (0.16mol) of potassium acetate (content: 97% by weight) Mixing is performed and the mixture is heated to 48 to 52°C. 176.85 g (1.68 mol) of acetic anhydride (content: 97% by weight) was added dropwise to the mixture over 5 hours, and then the mixture was continuously stirred at the same temperature for 6 hours. The reaction mixture was analyzed by gas chromatography internal standard method, and the yield of (3-methyl-2-butenyl) acetate was found to be 100% (based on 3-methyl-2-buten-1-ol). The reaction mixture was cooled to 28 to 32°C. After 35.2 g of water was added dropwise thereto within 1 hour, 105.5 g of water was added thereto, and the mixture was continuously stirred at the same temperature for 1 hour. The reaction mixture was left standing and separated to obtain 261.5 g of an organic layer containing (3-methyl-2-bu...

Embodiment 2

[0040] Embodiment 2 (purification step)

[0041] 83.7 g of a 5% aqueous solution of sodium bisulfite was added to the organic layer obtained in Example 1, the mixture was stirred at 20 to 30° C. for 1 hour, and then the mixture was left to stand and separated to obtain an organic layer. 70.3 g of water was added to the organic layer, the mixture was stirred at the same temperature for 30 minutes, and then the mixture was left to stand and separated to obtain an organic layer. The organic layer was cooled to 15 to 25°C, 44.9 g of a 30% aqueous solution of potassium carbonate was added dropwise thereto, and then 67.3 g of a 5% aqueous solution of sodium bicarbonate was added thereto. The mixture was stirred at the same temperature for 30 minutes, and then the mixture was left to stand and separated to obtain an organic layer. 70.3 g of water was added to the organic layer, the mixture was stirred at the same temperature for 30 minutes, and then, the mixture was left to stand an...

Embodiment 3

[0045] Embodiment 3 (reaction steps)

[0046] Under a nitrogen atmosphere, 552.9 g (6.40 mol) of 3-methyl-2-buten-1-ol (content: 99.7% by weight) and 48.6 g (0.48 mol) of potassium acetate (content: 97% by weight) Mixing is performed and the mixture is heated to 48 to 52°C. 707.3 g (6.72 mol) of acetic anhydride (content: 97% by weight) was added dropwise to the mixture over 5.5 hours, and then the mixture was continuously stirred at the same temperature for 9 hours. The reaction mixture was analyzed by gas chromatography internal standard method, and the yield of (3-methyl-2-butenyl) acetate was found to be 100% (based on 3-methyl-2-buten-1-ol). The reaction mixture was cooled to 28 to 32°C. After 138 g of water was added dropwise thereto within 1 hour, 415 g of water was added thereto, and the mixture was continuously stirred at the same temperature for 1 hour. The reaction mixture was left to stand and separated to obtain 1045.7 g of an organic layer containing (3-methyl...

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Abstract

The present invention relates to a process for the preparation of (3-methyl-2-butenyl) acetate comprising the reaction of 3-methyl-2-buten-1-ol with acetic anhydride in the presence of an inorganic base catalyst , and relates to a process for the preparation of purified (3-methyl-2-butenyl) acetate comprising subjecting crude (3-methyl-2-butenyl) acetate to an alkali metal Either step (A) of contacting an aqueous solution of bisulfite is carried out, or step (B) of contacting it with an aqueous solution of base is carried out, or steps (A) and (B) are carried out.

Description

technical field [0001] The present invention relates to a process for the preparation of (3-methyl-2-butenyl) acetate. Background technique [0002] (3-Methyl-2-butenyl) acetate is a useful compound as a raw material for various chemicals such as pharmaceuticals and agricultural chemicals. For example, by reacting (3-methyl-2-butenyl) acetate with ethyl diazoacetate, it can be used to prepare cyclopropane compounds, which are important intermediates in the synthesis of pyrethroids (e.g., Non-Patent Document 1). [0003] For example, as a method for producing (3-methyl-2-butenyl) acetate, there is known a method comprising 3-methyl-2-buten-1-ol and acetic anhydride in the presence of an excess amount of an amine compound. Methods of reaction (for example, Non-Patent Documents 2 and 3) and methods including the reaction of 3-methyl-2-buten-1-ol with acetic anhydride in the presence of acid catalysts such as magnesium perchlorate and indium chloride (eg, Non-Patent Documents...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C67/58C07C69/145
Inventor 增本胜久板垣诚
Owner SUMITOMO CHEM CO LTD
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