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Method for efficiently synthesizing N-methyltaurine and sodium N-methyltaurate

A technology of sodium methyl taurine and methyl taurine, which is applied in the direction of sulfonic acid preparation, sulfonate preparation, chemical instruments and methods, etc., can solve the problems of complex operation, excessive raw material surplus, harsh reaction conditions, etc. Achieve the effects of high reaction conversion rate, lower production cost, and less difficult operation

Active Publication Date: 2021-12-21
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions of this method are harsh, and due to the incomplete methylation, there are many raw materials remaining, the yield is low, the operation is complicated, and there are great problems in the reaction and storage process of industrialization.
[0005] CN106674061 discloses the preparation of N-methyl sodium taurate with N-methyl acetamide and concentrated sulfuric acid reaction, although the reaction conditions are improved compared with the common method at this stage, there are also limited sources of raw materials, high cost, low conversion rate, etc. question

Method used

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  • Method for efficiently synthesizing N-methyltaurine and sodium N-methyltaurate
  • Method for efficiently synthesizing N-methyltaurine and sodium N-methyltaurate
  • Method for efficiently synthesizing N-methyltaurine and sodium N-methyltaurate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] 1) Preparation of catalyst a

[0078] S1: Dissolve 229.1g of binaphthyldiol in 1L of toluene and lower the temperature to 0°C. At this temperature, add N,N-dimethylformamide (DMF) containing 329.6g of phosphorus trichloride dropwise into the solution. ) solution, the temperature was raised to 55° C. and stirred for 2 h after dripping. The toluene and DMF in the system were removed by rotary evaporation under reduced pressure, and the remaining materials were placed in a vacuum drying oven at -0.1MpaG and dried at 50°C for 12 hours to obtain a yellow fluffy compound binaphthyldioxyphosphorus chloride.

[0079] S2: at N 2 Under protection, the obtained compound was dissolved in 1.5L of tetrahydrofuran, cooled to 0°C, and 1.2L of newly prepared menthyl magnesium chloride with a concentration of 1.0mol / L was added dropwise to the system. 4h, the catalyst precursor binaphthyldioxymenthylphosphine was obtained.

[0080] S3: Under a nitrogen atmosphere, add 1.2 L of 0.8 mol...

Embodiment 2

[0114] (1) Synthesis of sodium isethionate

[0115] Add 300g of water to the reactor, add 0.68g of catalyst a, and feed SO 2 Raise the temperature until the pH=5.9, wait until the temperature of the system rises to 75°C, and add SO to the system at the same time 2 and a NaOH solution with a concentration of 15.8wt% to adjust the SO 2 and NaOH feed rate are 15.8g / min and 65.5g / min respectively, open the EO feed valve, and adjust the EO feed rate to be 11.4g / min. The system pressure at this stage is 0.2MpaG. The discharge rate of the reactor was adjusted to 92.7 g / min, and a sample was taken after 5 hours of discharge. The conversion rate of the reaction was 99.87% and the selectivity was 98.27% as measured by the IC external standard method.

[0116] NMR characterization results are 1 H NMR (CDCl 3 , 400MHz) δppm 4.11 (t, J = 7.1Hz 2H), 3.67 (s, 1H), 2.65 (t, J = 7.1Hz, 2H).

[0117] (2) Synthesis of sodium N-methyl taurate

[0118] Put 5562.3 g of the crude sodium iseth...

Embodiment 3

[0131] (1) Synthesis of sodium isethionate

[0132] Add 300g of water to the reactor, add 2.27g of catalyst b, and feed SO 2 Until PH = 6.3, raise the temperature until the temperature of the system rises to 78°C, and at the same time, feed SO into the system 2 and a NaOH solution with a concentration of 10.4wt%, adjusting the SO 2 and NaOH feed rate are 16.0g / min and 97.8g / min respectively, open the EO feed valve, and adjust the EO feed rate to be 11.3g / min. The system pressure at this stage is 0.3MpaG. The discharge rate of the reactor was adjusted to 125.1 g / min, and a sample was taken after 6 hours of discharge. The conversion rate of the reaction was 98.56% and the selectivity was 93.70% as measured by the IC external standard method.

[0133] (2) Synthesis of sodium N-methyl taurate

[0134] Put 5007.5 g of the crude sodium isethionate solution prepared in the previous step into the reactor, continue to add 372.9 g of methylamine, heat up to 150 ° C, and use N 2 Pre...

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PUM

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Abstract

The invention relates to a method for efficiently synthesizing N-methyltaurine and sodium N-methyltaurate, which comprises the following steps of: preparing sodium isethionate in situ from ethylene oxide, sulfur dioxide and sodium hydroxide under the action of a boron phosphine ligand catalyst, adding methylamine into a reactor, and generating the sodium N-methyltaurate under the action of the same catalyst, and then generating N-methyltaurine and sodium sulfate through sulfating of sodium N-methyltaurate. The process has the advantages of high catalytic efficiency of the catalyst, convenience in post-treatment of the product and high reaction yield, and is a green and environment-friendly process.

Description

technical field [0001] The invention belongs to the field of nutritional chemical synthesis, and in particular relates to a method for efficiently synthesizing N-methyl taurine and sodium N-methyl taurine. Background technique [0002] Sodium N-methyl taurate, also known as sodium methyl taurate, is an important derivative of taurine and can be used as a daily chemical and pharmaceutical intermediate. In the field of daily chemicals, it can be used to synthesize sodium cocoyl-N-methyl taurate, sodium polyacryloyl dimethyl taurate, polydimethylsiloxane PEG-7 acetyl methyl taurine A variety of high value-added products such as sodium acrylate and sodium hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer, these products are generally considered mild surfactants due to their mild properties, as people The demand for leather in personal care is increasing day by day, and the mild surfactant market is showing a rapid growth trend. N-methyl taurine sodium series surfa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14C07C303/32C07C303/02C07C309/08B01J31/02C07F9/50
CPCC07C303/32C07C303/02B01J31/0272B01J31/0275C07F9/5018C07F9/5022C07F9/5031C07F9/505C07C309/08C07C309/14Y02P20/584
Inventor 郭斌桂振友刘杰张昊蔺海政张静钟子太丰茂英付广权
Owner WANHUA CHEM GRP CO LTD
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