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Method for preparing 1-propone-1,3-sultone

A technology of sultone and propylene, which is applied in the field of preparation of organic materials, can solve the problems of no industrial value and low yield, and achieve the effects of low cost, high product quality and mild reaction conditions

Active Publication Date: 2013-03-13
SHIJIAZHUANG SAN TAI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The process is simple, and the three wastes are less, but the yield is too low and has no industrial value

Method used

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  • Method for preparing 1-propone-1,3-sultone
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  • Method for preparing 1-propone-1,3-sultone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] A 500mL four-necked flask is equipped with a mechanical stirrer, an air inlet tube, and a dropping funnel. Put 50mL of propargyl alcohol and 100mL of water into the flask, and the temperature of the water bath is 30-35°C. Dissolve 20g of potassium bisulfite in 100mL of water to form a solution. Stirring was started, air was introduced at a rate of 10mL / min, and potassium bisulfite solution was added dropwise. After the dropwise addition was completed, the mixture was incubated and stirred for 3 hours.

[0062] Add 20mL of hydrochloric acid to the reaction system, concentrate with a rotary evaporator to the remaining 80mL, add 100mL of hydrochloric acid and 100mL of methanol, cool down to 10°C, and a large amount of crystals appear.

[0063] filter. The filtrate was concentrated until no liquid was evaporated, and the residue was heated to 120-130°C in an oil bath, reduced to 20mmHg, and kept ring-closed until anhydrous was evaporated.

[0064] The residue after cycli...

Embodiment 2

[0066] The reaction is the same as in Example 1. After the reaction is complete, add 30 mL of hydrochloric acid to the reaction system, concentrate to dryness with a rotary evaporator, place the residue in an oil bath and heat to 120-130° C., reduce the pressure to 20 mmHg, and keep warm until anhydrous and evaporate.

[0067] The residue after cyclization was extracted three times with 200mL×2 dichloromethane under reflux, the dichloromethane extracts were combined and concentrated, and a large number of white needle-like crystals were precipitated, filtered and recrystallized to obtain 6.4g of the product, with a yield of 32%, mp: 84~85℃, content: 99.9% (GC)

Embodiment 3

[0069] The reaction is the same as that in Example 1. After the reaction is complete, 30 mL of hydrochloric acid is added to the reaction system for acidification, and the obtained mixed solution is separated by column chromatography. The mobile phase is dichloromethane: methanol=1: 1, and the obtained 1-sulfonic acid-1-propenol After the solvent was evaporated from the solution, 12.5g of the product was obtained by direct high-vacuum ring-closure distillation, with a yield of 62.5%, mp: 84-85°C, content: 99.9% (GC)

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Abstract

The invention relates to a method for preparing 1-propene-3-sultone, and the technical field of preparation of organic materials. The method mainly comprises the processes of addition, acidation and cyclization: a, addition, namely an addition reaction of propargyl ethanol and alkali metal sulphite or hydrosulfite is carried out in an aqueous solution, the molar ratio of the propargyl alcohol to the alkali metal sulphite or the hydrosulfite is 1:1-10, and inorganic acid or organic acid is added to stop reaction after the addition reaction is ended; and b, a product of the addition reaction is separated out, and then the separated product is subjected to cyclization and separation to obtain a 1-propene-3-sultone product. The PST product can be refined. The method overcomes the defect of the prior art, and has the remarkable advantages of unique method, simple manufacturing process, easy operation, mild reaction conditions, cheap and easily-obtained raw materials, higher yield, good selectivity, high and stable quality of products, few three wastes, lower cost, remarkable economic benefit, and the like.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic materials, and in particular relates to a preparation method of 1-propene-1,3-sultone. Background technique [0002] 1-propene-1,3-sultone, English name Prop-1-ene-1,3-sulton (referred to as PST) Molecular formula: C 3 h 4 o 3 S CAS: 21806-61-1 [0003] Structural formula: [0004] [0005] The compound is an important pharmaceutical intermediate and electronic chemical. The structure of 1-propene-1,3-sultone contains unsaturated bonds and heteroatoms, and its unique structure makes it play an irreplaceable role in the synthesis of heterocyclic drugs. In recent years, PST has been widely used as an additive to lithium battery electrolyte, which can improve battery performance and greatly extend the rechargeable life of the battery. [0006] In 1999, Jiang L.S et al. [Tetrahedron 55, 2245 (1999)] started from allyl chloride and eliminated the preparation of PST through subst...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D327/04
Inventor 郭秀彬梅银平
Owner SHIJIAZHUANG SAN TAI CHEM CO LTD
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