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Method for preparing 2-((2-aminoethyl) amino)-ethanesulfonic acid monosodium salt

A technology of sodium ethylenediaminoethanesulfonate and sodium taurine, which is applied in the direction of sulfonic acid preparation, sulfonate preparation, organic chemistry, etc., and can solve the problem that sulfonic acid-type hydrophilic chain extenders do not have cost advantages and impurities Difficult to separate, high cost of raw materials and other problems, to achieve the effect of good industrialization prospects, high product selectivity, mild reaction conditions

Active Publication Date: 2018-04-20
WANHUA CHEM GRP CO LTD
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Problems solved by technology

[0003] At present, the production routes of sodium ethylenediaminoethanesulfonate reported in the literature mainly include sodium chloroethylsulfonate route and sodium vinylsulfonate route, which have the problems of high raw material cost, difficult separation of impurities, and low product yield.
[0004] Kang Pingping (Organic Chemistry, 2009, 29(6):904~908) used ethylenediamine and 2-sodium chloroethanesulfonate as raw materials, and produced ethylenediaminoethanesulfonic acid by nucleophilic substitution reaction in the presence of NaOH Sodium, this method has high raw material conversion rate and high product selectivity, but it is difficult to remove the by-product sodium chloride, and the product purity is low.
[0005] Chinese patent CN101240057 and Japanese patent JPS5859959 use polyamine and alkenyl sulfonate as raw materials to prepare sulfonic acid type hydrophilic chain extender, and alkenyl sulfonate is relatively expensive, so the sulfonic acid type hydrophilic chain extender produced by this method Chain agent does not have a cost advantage
[0006] Chinese patent CN102702037 uses β-hydroxyethyl ethylenediamine as a raw material to be esterified into ethylenediaminoethanol esterified products, and then uses sulfite as a sulfonating agent to carry out sulfonation reaction on ethylenediaminoethanol esterified products. 1. Purification and preparation of ethylenediamino ethyl sulfonate, the reaction time of this route is longer, the yield is not high, and a large amount of three wastes are produced
[0007] Therefore, need to find a kind of new production method of sodium ethylenediamine ethanesulfonate, to solve the problems such as high raw material cost, difficult separation of impurities, low product yield in the traditional process

Method used

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  • Method for preparing 2-((2-aminoethyl) amino)-ethanesulfonic acid monosodium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) add 125 gram taurine, 118 gram 37wt% formaldehyde aqueous solution and 650 gram ethanol in the there-necked flask, stir 10 minutes under 25 ℃, in 30 minutes, 68 gram nitromethanes are added dropwise in the there-necked flask, be warming up to 30°C, stirred for 20 hours, the reaction solution was distilled under reduced pressure to remove light components, the solid was washed with 300 grams of water, and dried in vacuum at 50°C for 4 hours to obtain light yellow solid N-(2-nitroethyl)taurine 194.4 g, yield 98.0%, selectivity 99.8%. IR(KBr):ν=3340cm -1 (N-H), ν=1550cm -1 (NO 2 ), ν=1200cm -1 (SO 3 ); 1 H NMR (400 MHz, DMSO-D6), δ = 2.76 (t, 2H), δ = 3.01 (t, 2H), δ = 3.14 (t, 2H), δ = 4.69 (t, 2H).

[0040] (2) under stirring, slowly add 99 grams of N-(2-nitroethyl) taurine in 66.7 grams of 30wt% sodium hydroxide aqueous solution, temperature control 30 ℃, continue to stir for 10 minutes after the solid is added completely; Water was distilled off under pressu...

Embodiment 2

[0044] (1) Add 125 grams of taurine, 35 grams of paraformaldehyde and 2500 grams of methanol in a three-necked flask, stir at 25°C for 20 minutes, add 88 grams of nitromethane dropwise to the three-necked flask in 30 minutes, and heat up to 70 ℃, stirred for 4 hours, the reaction solution was distilled under reduced pressure to remove light components, the solid was washed with 260 grams of water, and dried in vacuum at 50 ℃ for 4 hours to obtain light yellow solid N-(2-nitroethyl) taurine 195.3 grams, yield 98.5%, selectivity 99.9%.

[0045](2) under stirring, slowly add 99 grams of N-(2-nitroethyl) taurine in 220 grams of 20wt% sodium bicarbonate aqueous solution, temperature control 40 ℃, continue to stir for 15 minutes after the solid is added completely; Water was distilled off under pressure to obtain 110 g of sodium N-(2-nitroethyl)taurate.

[0046] (3) 110 grams of N-(2-nitroethyl) sodium taurate, 7000 grams of ethanol, and 1 gram of Raney's nickel catalyst are added ...

Embodiment 3

[0049] (1) Add 125 grams of taurine, 95 grams of 37wt% formaldehyde solution and 1500 grams of dimethyl sulfoxide in a three-necked flask, stir at 25°C for 10 minutes, and add 76 grams of nitromethane dropwise to the three-necked flask within 30 minutes , heated to 55°C and stirred for 6 hours, the reaction solution was distilled under reduced pressure to remove light components, the solid was washed with 300 g of water, and dried under vacuum at 50°C for 4 hours to obtain a pale yellow solid N-(2-nitroethyl ) 194.9 grams of taurine, yield 98.2%, selectivity 99.8%.

[0050] (2) under stirring, slowly add 99 grams of N-(2-nitroethyl) taurine in the aqueous sodium hydroxide solution of 200 grams of 10wt%, temperature control 35 ℃, continue to stir for 10 minutes after solid is added completely; Water was distilled off under pressure to obtain 110 g of sodium N-(2-nitroethyl)taurate.

[0051] (3) 110 grams of N-(2-nitroethyl) sodium taurate, 3000 grams of N,N-dimethylformamide, ...

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Abstract

The invention discloses a method for preparing 2-((2-aminoethyl) amino)-ethanesulfonic acid monosodium salt. The method comprises the following steps: ensuring that taurine, nitromethane and formaldehyde are subjected to Mannich reaction, so as to produce N-(2- nitryl ethyl) taurine, and then the N-(2- nitryl ethyl) taurine is subjected to alkali neutralization and hydrogenation reaction, so as toform the 2-((2-aminoethyl) amino)-ethanesulfonic acid monosodium salt. The product selectivity is greater than 99 percent, and the product yield is greater than 97 percent. The process route is richin raw material resources, green and environmentally friendly, high in product selectivity and product yield, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a method for preparing sodium ethylenediaminoethanesulfonate. Background technique [0002] Sodium ethylenediaminoethanesulfonate (H 2 NCH 2 CH 2 NHCH 2 CH 2 SO 3 Na) is a new type of high solid content anionic waterborne polyurethane chain extender. Due to the sulfonate group, it has excellent hydrophilicity. As a hydrophilic chain extender or hydrophilic monomer, it is used in the preparation of waterborne polyurethane resin, and is suitable for industries such as coatings, inks, adhesives, and leather finishing agents. Polyurethane dispersions synthesized by sodium ethylenediaminoethanesulfonate have good hydrolytic stability and good compatibility with other anionic or nonionic aqueous dispersions. [0003] The current production routes of sodium ethylenediaminoethanesulfonate reported in the literature mainly include sodium chloroethylsulfonate r...

Claims

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Application Information

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IPC IPC(8): C07C303/32C07C303/22C07C309/14
CPCC07C303/22C07C303/32C07C309/14
Inventor 崔乾何光文王鹏丛鑫郑超董科刘超黎源
Owner WANHUA CHEM GRP CO LTD
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