Synthesis method of 2-(2-chloroethoxy) acetic acid

一种氯乙氧基乙醇、合成方法的技术，应用在2-乙酸的合成领域，能够解决影响产品质量、制备过程复杂、产品纯化困难等问题，达到高优越性、后处理简单、危害小的效果

Inactive Publication Date: 2010-09-29
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, the compound is synthesized by condensation of 2-chloroethanol and chloroacetic acid, and the by-products are many and difficult to remove
It has been reported that 2-oxo-1,4-dioxane was prepared by catalytic dehydrogenation of diethylene glycol, and then reacted with thionyl chloride and corresponding lower alcohols to generate 2-(2-chloroethoxy Base) acetate, and then acid hydrolysis to obtain 2-(2-chloroethoxy) acetic acid (Chemical Research and Application, 2001, 13 (5), 534-536), diethylene glycol is used for the industrial preparation of ethylene glycol The by-product of diol, the source is limited, the preparation process is complicated, and the yield is not high (about 48%); It is reported that 2-(2-chloroethoxy)ethanol is oxidized to prepare 2-(2-chloroethane) by microbial method Oxy)acetic acid (KIENER ANDREASDR, GLOCKLER RAINER. Microbiological prepn. of glycolic acid ether(s): CH, 686003[P], 1995-11-30), the yield is 87%, but the process requirements are high, and product purification is difficult; It has been reported that hydroxyzine is directly oxidized to cetirizine (TA0Y, KARIMIAN K TAM T.Methods for the manufacture of cetirizine: WO, 02425) with Jones reagent (chromium trioxide-sulfuric acid), or with oxygen and platinum dioxide as oxidants [P], 1998-01-22), the reaction process is simple, but it is easy to introduce chromium ions and nitrogen oxide by-products in the product, which seriously affects the product quality; there are also related documents that directly oxidize alcohol with nitric acid direct oxidation to obtain the corresponding acid (Journal of Hunan Normal University, 2008, 31 (2) 84-86), but use n-butanol as extractant in the post-processing of this document, the cost is higher

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Cool a 150ml three-neck flask equipped with a reflux and gas absorption device to 0-5°C, add 12.45g (0.1mol) of 2-(2-chloroethoxy)ethanol, and slowly add 24.9mL of water diluted with Concentrated nitric acid 9.7ml (0.1mol). After the addition is completed, stir and react in a water bath at 30-35°C for 20 hours, then heat to 80-90°C to produce a large amount of reddish-brown NO 2 gas, stir the reaction until no more gas is produced. Cool to room temperature, pour the reaction solution into 100ml of ice water, stir for 1-2h, evaporate most of the water under reduced pressure, dry with anhydrous sodium sulfate, filter, and then carry out vacuum distillation to collect 130~132℃, 0.67kPa Distillation yielded 13.2 g of a colorless liquid, namely 2-(2-chloroethoxy)acetic acid, yield: 95%.

[0020] 1 HNMR (400MHz, CDCl 3 ): δ (ppm) 4.24 (s, 2H), 3.86 (t, 2H,), 3.69 (t, 2H,).

Embodiment 2

[0022] Cool the 150mL three-neck flask equipped with a reflux and gas absorption device to 0-5°C, add 12.45g (0.1mol) of 2-(2-chloroethoxy)ethanol, and slowly add 24.9mL of water diluted with Concentrated nitric acid 24.3ml (0.25mol). After the addition, stir and react in a water bath at 30-40°C for 20 hours, and then heat to 80-90°C to produce a large amount of reddish-brown NO 2 gas, stir the reaction until no more gas is produced. Cool to room temperature, pour the reaction solution into 100ml of ice water, stir for 1-2h, evaporate most of the water under reduced pressure, dry with anhydrous sodium sulfate, filter, and then carry out vacuum distillation to collect 130~132℃, 0.67kPa Distillation yielded 13.2 g of a colorless liquid, namely 2-(2-chloroethoxy)acetic acid, yield: 95%.

[0023] 1 HNMR (400MHz, CDCl 3 ): δ (ppm) 4.24 (s, 2H), 3.86 (t, 2H,), 3.69 (t, 2H,).

Embodiment 3

[0025] Cool the 150mL three-neck flask equipped with a reflux and gas absorption device to 0-5°C, add 12.45g (0.1mol) of 2-(2-chloroethoxy)ethanol, and slowly add in 2-(2-chloroethoxy)ethanol at this temperature Diluted with 49.8mL of water Concentrated nitric acid 48.5ml (0.5mol). After the addition, stir and react in a water bath at 50-60°C for 20 hours, then heat to 80-90°C to produce a large amount of reddish-brown NO 2 gas, stir the reaction until no more gas is produced. Cool to room temperature, pour the reaction solution into 100ml of ice water, stir for 1-2h, evaporate most of the water under reduced pressure, dry with anhydrous sodium sulfate, filter, and then carry out vacuum distillation to collect 130~132℃, 0.67kPa Distillation yielded 13.2 g of a colorless liquid, namely 2-(2-chloroethoxy)acetic acid, yield: 95%.

[0026] 1 HNMR (400MHz, CDCl 3 ): δ (ppm) 4.24 (s, 2H), 3.86 (t, 2H,), 3.69 (t, 2H,).

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Abstract

The invention relates to a synthesis method of 2-(2-chloroethoxy) acetic acid, which belongs to the technical field of the preparation and the application of fine chemical engineering products. The invention particularly belongs to the synthesis method of 2-(2-chloroethoxy) acetic acid. The invention uses 2-chloroethoxy ethanol as starting materials, uses water as solvents, and uses nitric acid for direct oxidization to obtain products. The reaction process is shown as the accompanying drawing. The invention adopts water as the solvents, and uses the nitric acid as oxidizing agents for efficiently oxidizing the 2-chloroethoxy ethanol into corresponding acids. The method has the advantages of simple operation, low price of raw materials, easy acquisition of raw materials, simple requirement on equipment, simple after treatment and the like. In addition, the use of the organic solvent has nearly zero cost, and the invention conforms to the environmental protection industrial production requirements, so the invention has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of fine chemical products, in particular to a synthesis method of 2-(2-chloroethoxy)acetic acid. Background technique [0002] 2-Chloroethoxyacetic acid, also known as: 2-(2-chloroethoxy)acetic acid, chloroethoxyacetic acid and 2-chloro 2′-carboxyethyl ether; English name: 2-Chloroethoxyacetic acid, chloroethoxyacetic acid and 2- Chloro-2'-carboxyl diethylether is a colorless transparent liquid that is easily soluble in water, alcohol, ether and other organic solvents. Density: 1.326g / ml, boiling point: 130-132°C (5mmHg). Molecular formula: C 4 h 7 o 3 Cl, molecular weight: 138.5, is a synthetic non-sedative histamine H 1 An important intermediate of receptor antagonist antiallergic drug cetirizine hydrochloride, cetirizine is currently one of the best-selling antiallergic drugs in the world. It is an antiallergic drug with long-acting selectivity and strong H 1 receptor ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/135C07C51/27
Inventor 徐凤波敖丽华张奉志孔晓菲柴德强
Owner NANKAI UNIV
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