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A kind of method for preparing sodium ethylenediamine ethanesulfonate

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 separation, low product purity, etc., to achieve good industrialization prospects, mild reaction conditions, and high product selectivity

Active Publication Date: 2020-06-02
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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  • A kind of method for preparing sodium ethylenediamine ethanesulfonate

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Experimental program
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Effect test

Embodiment 1

[0039] (1) Add 125 g of taurine, 118 g of 37wt% aqueous formaldehyde solution and 650 g of ethanol to a three-necked flask, stir at 25°C for 10 minutes, drop 68 g of nitromethane into the three-necked flask within 30 minutes, and heat to After stirring for 20 hours at 30°C, the reaction solution was distilled under reduced pressure to remove light components. The solid was washed with 300 grams of water and vacuum dried at 50°C for 4 hours to obtain a 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 (400MHz, 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 g of N-(2-nitroethyl) taurine to 66.7 g of 30wt% sodium hydroxide aqueous solution, control the temperature at 30°C, and continue stirring for 10 minutes after the solid is added completely; The water was removed by pressure distillation to ...

Embodiment 2

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

[0045] (2) Under stirring, slowly add 99 g of N-(2-nitroethyl) taurine to 220 g of 20wt% sodium bicarbonate aqueous solution, control the temperature at 40°C, and continue stirring for 15 minutes after the solid is added completely; The water was removed by pressure distillation to obtain 110 g of sodium N-(2-nitroethyl) taurate.

[0046] (3) Put 110 grams of sodium N-(2-nitroethyl) taurate, 7000 grams of ethanol, and 1 gram of Raney nickel catal...

Embodiment 3

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

[0050] (2) Under stirring, slowly add 99 grams of N-(2-nitroethyl) taurine to 200 grams of 10wt% aqueous sodium hydroxide solution, control the temperature at 35°C, and continue stirring for 10 minutes after the solids are completely added; The water was removed by pressure distillation to obtain 110 g of sodium N-(2-nitroethyl) taurate.

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

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Abstract

The invention discloses a method for preparing sodium ethylenediaminoethanesulfonate. The method comprises the following steps: taurine, nitromethane and formaldehyde occur Mannich reaction to generate N-(2-nitroethyl) taurine, and then N-(2-nitroethyl) taurine Sodium ethylenediaminoethanesulfonate can be obtained through alkali neutralization and hydrogenation reaction. The product selectivity is greater than 99%, and the product yield is greater than 97%. The process route has abundant sources of raw materials, is environmentally friendly, has high product selectivity and high product yield, and is suitable for industrial production.

Description

Technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically 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 resins, and is suitable for industries such as coatings, inks, adhesives and leather finishing agents. The polyurethane dispersion synthesized using sodium ethylenediamine ethanesulfonate has good hydrolytic stability and good compatibility with other anionic or non-ionic water dispersions. [0003] At present, the production routes of sodium ethylenediamine ethanesulfonate reported in the literature mainly include sodium chloroethyl sulfonate rout...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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