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Synthesis method for oxetane compounds

A technology for oxetane and a synthesis method, applied in directions such as organic chemistry, can solve the problems of complicated separation and purification of products and organic solvents, unfavorable industrial production of oxetane, large environmental pollution, etc., and achieves high utilization rate , less by-products, less environmental pollution

Active Publication Date: 2011-10-12
赵燕 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These preparation methods are not because the yield is low, solid sodium bromide is separated out in the reaction process, or because a large amount of organic solvents need to be used, the cost of alkaline solution needs to be added dropwise, etc., the cost is high, the environmental pollution is large, and the separation and refining of the product and the organic solvent More complex, not conducive to large-scale industrial production of oxetane

Method used

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  • Synthesis method for oxetane compounds
  • Synthesis method for oxetane compounds
  • Synthesis method for oxetane compounds

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Embodiment 1

[0033] The preparation of embodiment 1 3-ethyl-3-bromomethyl oxetane

[0034] With 37.75 gram (0.125mol) 2,2-bisbromomethyl-1-butanol acetate, 0.402 gram (0.00125mol) tetrabutylammonium bromide, 48.0 gram mass fraction 25% sodium hydroxide (0.3mol ) solution was added to the reaction flask together. Start to stir, heat to keep the reaction temperature at 70°C for 3 hours, and the reaction ends. 21.87 g of the organic phase was separated, and the content of the product 3-ethyl-3-bromomethyloxetane in the organic phase was analyzed by gas chromatography to be 76.0%. The reaction yield reached 74.3%.

Embodiment 2

[0035] Example 2 Preparation of 3-hydroxymethyl-3-bromomethyloxetane

[0036] Add 65.5 g (0.25 mol) of dibromoneopentyl glycol, 1.61 g (0.005 mol) of tetrabutylammonium bromide, and 60.0 g of 20% sodium hydroxide (0.3 mol) solution into the reaction flask. Start to stir, heat to keep the reaction temperature at 30°C for 6 hours, continue to heat up to 75°C for 1.5 hours, and the reaction ends. 35.75 g of the organic phase were separated off. With 15.0 grams of dichloromethane, extract the aqueous phase twice, and combine the organic phases to obtain 59.85 grams of organic phases. The content of product 3-hydroxymethyl-3-bromomethyloxetane in the gas chromatography analysis organic phase is 65.78%. The reaction yield reached 87%.

Embodiment 3

[0037] Embodiment 3 3, the preparation of 3-bismethyloxetane

[0038] 41.75 grams (0.25mol) of 2-methyl-2-bromomethylpropanol, 3.24 grams (0.0125mol) of tetrabutylammonium hydroxide, and 44.45 grams of sodium hydroxide (0.5mol) solution with a mass fraction of 45% were added together for reaction in the bottle. Stirring was started, and the reaction temperature was maintained at 40° C. for 10 hours by heating. After the reaction was completed, 20.65 grams of the organic phase was separated, and the content of the product 3 in the organic phase was analyzed by gas chromatography, and the content of 3-bismethyloxetane was 76.0%. The reaction yield reached 73.0%.

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Abstract

The invention provides a novel synthesis method for oxetane compounds, which comprises the following steps: adding 3-halo-1-propanol shown in formula (1) or an ester thereof used as a raw material in the presence of an alkaline water solution or water suspension, adding a proper amount of phase transfer catalyst, heating to carry out phase transfer reaction, removing hydrogen halide, and carrying out cyclization reaction to obtain products shown in formula (2) at high yield. According to the invention, no organic solvent is used during the reaction process; the reaction system only contains the alkaline water solution and the small amount of phase transfer catalyst besides the raw material; and the process is simple and feasible, has the advantages of low cost, no solvent recovery, few byproducts, easy refining of crude products, relative environmental friendliness, high yield and high equipment utilization rate, and facilitates the industrial mass production of oxetane.

Description

technical field [0001] The present invention relates to a novel synthesis method of oxetane compounds. Belongs to the field of organic chemistry technology Background technique [0002] Oxetane series monomers are very important organic compound monomers. After ring-opening polymerization of such monomers, they can form functional prepolymers whose main chain is polyether links. This prepolymer can be widely used in medicine, Coatings, lubricants, adhesives and many other fields are currently being researched on their synthesis and application at home and abroad. [0003] In the existing preparation method of oxetane, the raw material 3-halogenated-1-propanol compound is all dehydrohalogenated in the presence of an organic solvent, and undergoes a ring closure reaction. [0004] In the patent CN1759107, polyalkyl ether is used as a catalyst, 3-halogenated-1-propanol compounds are added to organic solvents such as toluene, and then sodium hydroxide solution is added dropwis...

Claims

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Application Information

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IPC IPC(8): C07D305/06
Inventor 赵燕熊丽
Owner 赵燕
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