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Preparation method of 1,3-propane sultone

A technology of propane sultone and propane sultone is applied in the field of preparation of 1,3-propane sultone, can solve the problems of flammability, explosion, strong corrosiveness, environmental hazards, etc. Inexpensive and readily available, mild reaction conditions and ideal yields

Active Publication Date: 2018-06-15
SUZHOU HUAYI NEW ENERGY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After that, people continued to improve the synthesis process for preparing 3-hydroxypropanesulfonic acid, but the basic raw material is allyl alcohol, which is a highly toxic substance and is flammable and explosive, so the risk of chemical production is very high
At the same time, sodium sulfite and sodium bisulfite are also used. A large amount of sulfur dioxide is produced during the acidification process, which has a high hazard to the environment. Concentrated hydrochloric acid and concentrated sulfuric acid are used in the acidification process, which is highly corrosive and unfavorable for safe production. , is not conducive to the protection of the environment

Method used

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  • Preparation method of 1,3-propane sultone
  • Preparation method of 1,3-propane sultone
  • Preparation method of 1,3-propane sultone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 450 g of anhydrous acetonitrile, 1,3-dichloropropane (113 g, 1 mol) and tetraethylammonium bromide (10 g, 0.05 mol) into a 1 L four-necked flask connected with a glassy carbon electrode, and feed a constant current. The density is 100mA / cm 2 After being heated to 40°C, 128g of dry sulfur dioxide gas is slowly passed through for 8 hours, and the tail gas is absorbed with liquid caustic soda. Gas chromatographic tracking of the reaction process, the product content unchanged after the ventilation is over, the reaction is over, concentrated acetonitrile under reduced pressure, added 400g of dichloromethane to dissolve the concentrated solution, washed twice with 100g of water, dried over anhydrous magnesium sulfate, concentrated to give 1,3 - 42 g of propane sultone, yield 39.6%, purity 99.4%.

[0031] product: 1 H-NMR (CDCl 3 ): δ(ppm)1.82(m,-CH 2 -), 2.57(t, J=6.3Hz, CH 2 S), 4.42(t, J=5.8Hz, CH 2 O)

[0032] Add 42g of 1,3-propane sultone, 100g of dichloromet...

Embodiment 2

[0035] Add 450 g of anhydrous acetonitrile, 1,3-dichloropropane (113 g, 1 mol) and tetraethylammonium bromide (10 g, 0.05 mol) into a 1 L four-necked flask connected with a glassy carbon electrode, and feed a constant current. The density is 100mA / cm 2 After being heated to 80°C, 96g of dry sulfur dioxide gas is slowly passed through for 6 hours, and the tail gas is absorbed with liquid caustic soda. Gas chromatographic tracking reaction process, product content constant after ventilating finishes, reaction finishes, acetonitrile is concentrated under reduced pressure, adds 200g dimethyl carbonate to dissolve concentrated solution, 50g water washes twice, anhydrous magnesium sulfate is dried, concentrates after filtering and obtains 1, 90 g of 3-propane sultone, yield 84.9%, purity 99.1%.

[0036] Add 90g of 1,3-propane sultone and 300g of dichloromethane into a 500mL three-necked flask, slowly add 160g of hydrogen peroxide with a mass fraction of 20% at room temperature, and...

Embodiment 3

[0038] Add 450 g of anhydrous acetonitrile, 1,3-dichloropropane (113 g, 1 mol) and tetraethylammonium bromide (10 g, 0.05 mol) into a 1 L four-necked flask connected with a glassy carbon electrode, and feed a constant current. The density is 100mA / cm2 After being heated to 80°C, 64g of dry sulfur dioxide gas is slowly passed through for 6 hours, and the tail gas is absorbed with liquid caustic soda. Gas chromatography traced the reaction process, and the product content remained unchanged after aeration. After the reaction was completed, the acetonitrile was concentrated under reduced pressure, and 200 g of dimethyl carbonate was added to dissolve the concentrate, washed twice with 100 g of water, dried over anhydrous magnesium sulfate, and concentrated to obtain 1,3 - Propylene sultone 89g, yield 83.9%, purity 99.2%.

[0039] Add 89g of 1,3-propane sultone and 200g of dimethyl carbonate into a 500mL three-neck flask, slowly add 157g of hydrogen peroxide with a mass fraction o...

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Abstract

The invention discloses a preparation method of 1,3-propane sultone. The preparation method of the 1,3-propane sultone comprises the following steps of (1) under the existence of tetraethylammonium bromide, reacting 1,3-dichloropropane and sulfur dioxide in acetonitrile under the action of a constant current so as to obtain 1,3- propane sulfincacid lactone; (2) carrying out oxidation reaction on the prepared 1,3-propane sulfincacid lactone and an oxidizing agent in an organic solvent to obtain the 1,3-propane sultone. The preparation method of the 1,3-propane sultone provided by the inventionhas the advantages of higher yield, high purity, cheap and easy-to-get raw materials, mild reaction conditions, simple preparation process and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 1,3-propane sultone. Background technique [0002] 1,3-propane sultone (1,2-Oxathiolane, 2,2-dioxide) is a colorless transparent crystal at room temperature, with a melting point of 30-33°C, a boiling point of 180°C / 30mmHg, and a density (20°C) of 1.392g / cm 3 , mainly used in pharmaceutical intermediates and lithium battery electrolyte and other fields. Its structural formula is as follows: [0003] [0004] The current method for preparing 1,3-propane sultone is mainly prepared by high temperature dehydration and ring closure of 3-hydroxypropanesulfonic acid. In 1939, Kharasch et al first synthesized 3-hydroxypropanesulfonic acid (J.Org.Chem., 3, 175 (1939)) using allyl alcohol and sodium bisulfite under an oxygen environment. In 1954, Helberger et al. used sodium hydroxide, sulfur dioxide and allyl alcohol to prepare 3-hydroxypropanesu...

Claims

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Application Information

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IPC IPC(8): C07D327/04
CPCC07D327/04
Inventor 周龙王小龙周洋管晓东
Owner SUZHOU HUAYI NEW ENERGY TECH CO LTD
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