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Synthesis method of di(2-halogenated ethyl) ether

A technology of haloethyl and synthesis method, which is applied in the field of synthesis of fine chemical intermediates, can solve the problems of high toxicity of chlorohydrin, low reaction selectivity, and large pollution, and achieve slow reaction, good selectivity, and high reaction temperature suitable effect

Active Publication Date: 2015-04-29
安徽伟祥新材料有限公司
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Problems solved by technology

The synthetic method of two (2-chloroethyl) ethers mainly contains following several kinds: 1. take diethylene glycol as raw material and sulfur oxychloride reaction, generate target product two (2-chloroethyl) ethers (Liu, Shu- Di; Zhang, Liang-Wei; Liu, Xiang; New Journal of Chemistry; vol. 37; nb. 3; (2013); p. 821 - 826), the method is simple and easy to obtain raw materials, but the reaction produces a large amount of The mixed acid tail gas of sulfur dioxide and hydrogen chloride is more polluting; 2. It is prepared by dehydrating chloroethanol with sulfuric acid (Kamm; Waldo; Journal of the American Chemical Society; vol. 43; (1921); p. 2225), the process is simple, However, it needs to consume a large amount of concentrated sulfuric acid to produce a lot of waste acid, and chlorohydrin is more toxic; 3. Ethylene reacts with chlorohydrin and chlorine to obtain the target product (Schilow; Zhurnal Obshchei Khimii; vol. 17; (1947); p. 1490), This method reaction selectivity is low, and yield is low, and uses the big chlorohydrin of toxicity and chlorine gas
The synthesis method of bis(2-bromoethyl)ether usually uses diethylene glycol as a raw material, and it is prepared by bromination with phosphorus tribromide under the catalysis of pyridine, which has serious pollution and high cost

Method used

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Experimental program
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Effect test

Embodiment 1

[0013] Embodiment 1: Preparation of raw material 1,4-thioxane-1,1-diox

[0014] According to the method of M.V.Rous (J.ORG.CHEM.2007, 72, 1143-47), 208 g of 1,4-thioxane, 300 ml of acetic acid and 400 ml of 30% hydrogen peroxide were stirred at room temperature for 2 days , after evaporating the solvent to dryness, recrystallized with dichloromethane-cyclohexane to obtain 204 g of 1,4-thioxane-1,1-dioxine, with a melting point of 76-78°C and a yield of 70%.

[0015] Product structure confirmation:

[0016] 1 HNMR (δppm, 400MHz , CDCl 3 ): 3.02-3.33(m, 4H); 4.05-4.23(m, 4H)

[0017] 13 CNMR (δppm, 100MHz, CDCl 3 ): 66.3; 53.0

[0018] IR: 2926, 1466, 1392, 1329, 1288, 1200, 1121, 1106

[0019] GC-MS: 15, 27, 28, 29, 43, 44(100%), 45, 65, 71, 72, 78, 109, 137

Embodiment 2

[0020] Embodiment 2: the preparation of two (2-chloroethyl) ethers

[0021] Add 68.1 grams of 1,4-thioxane-1,1-diox (0.5 moles) and 200 grams of hydrochloric acid (2 moles) with a mass concentration of 36.5% into a 500 mL four-neck flask, stir mechanically at 30°C and react in the gas phase Chromatography followed the reaction, and the reaction ended in 12 hours; layered, about 175 grams of the upper acid layer was set aside; the lower organic layer was washed with 50 ml of saturated sodium bicarbonate, layered, and the boiling range of 60-75 ° C was collected by water pump distillation to obtain Color liquid 59.2 grams, gas phase content 98.2%, yield 81.3%.

[0022] Product structure confirmation:

[0023] 1 HNMR (δppm, 400MHz , CDCl 3 ): 3.77 (4H, t, J =7.2 Hz, CH 2 O); 3.62 (4H, t, J = 7.2 Hz, CH 2 Cl)

[0024] 13 CNMR (δppm, 100MHz, CDCl 3 ): 71.3; 42.6

[0025] IR: 2866, 1301, 1126, 747, 659

[0026] GC-MS: 27, 28, 63, 65, 93, 95(100%), 142

Embodiment 3

[0027] Embodiment 3: apply mechanically hydrochloric acid to prepare two (2-chloroethyl) ethers

[0028] 68.1 grams of 1,4-thioxane-1,1-diox (0.5 moles), 175 grams of hydrochloric acid (about 1.5 moles) and 50 grams of new hydrochloric acid with a mass concentration of 36.5% (0.5 moles) were recovered in Example 2 ) into a 500mL four-neck flask, stirred mechanically and reacted at 30°C. The reaction was followed by gas chromatography, and the reaction was completed in 15 hours; the layers were separated, and the lower organic layer was washed with 50 mL of saturated sodium bicarbonate. Liquid 61.2 grams, gas phase content 98.5%, yield 84.3%. Product proton nuclear magnetic spectrum is identical with embodiment 2.

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Abstract

The invention relates to the synthesis of fine chemical intermediates, in particular to a synthesis method of di(2-halogenated ethyl) ether. According to the synthesis method, 1,4-thioxane-1,1-dioxo and a hydrogen halide water solution react with each other to obtain the target product, namely di(2-halogenated ethyl) ether. The synthesis method is simple and convenient in technical route, good in selectivity, high in yield, less in pollution and simple in post-processing, conforms to the tendency of the green chemical industry nowadays, and has great industrial value.

Description

technical field [0001] The invention relates to the synthesis of fine chemical intermediates, in particular to a synthesis method of bis(2-halogenated ethyl) ethers. Background technique [0002] Bis(2-halogenated ethyl) ether mainly includes bis(2-chloroethyl) ether and bis(2-bromoethyl) ether, etc. It is a colorless and transparent liquid with a spicy and fruity taste, commonly used It can be used as a high-grade solvent for fat, oil, wax, rubber, tar, asphalt, resin, ethyl cellulose, etc. It is also used as a dry-cleaning agent for high-grade woolen clothes, and it is also an important fine chemical intermediate. The synthetic method of two (2-chloroethyl) ethers mainly contains following several kinds: 1. take diethylene glycol as raw material and sulfur oxychloride reaction, generate target product two (2-chloroethyl) ethers (Liu, Shu- Di; Zhang, Liang-Wei; Liu, Xiang; New Journal of Chemistry; vol. 37; nb. 3; (2013); p. 821 - 826), the method is simple and easy to obt...

Claims

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Application Information

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IPC IPC(8): C07C43/12C07C41/01
CPCC07C41/01C07C43/12
Inventor 李毅唐鹏飞易思利沈润溥彭本军
Owner 安徽伟祥新材料有限公司
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