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Novel method for preparing taurine

A technology of taurine and bisulfite, applied in the preparation of sulfonic acid, organic chemistry and other directions, can solve the problems of high energy consumption, potential safety hazards, etc., and achieve the effects of high yield, convenient operation and low energy consumption

Active Publication Date: 2014-03-05
HUBEI GRAND LIFE SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The invention relates to a new method for producing taurine, which aims to solve the problems of potential safety hazards and high energy consumption in the existing method using ethylene oxide as raw material

Method used

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  • Novel method for preparing taurine

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1: the synthetic method one of 2-nitroethanol

[0035] At 30°C, add paraformaldehyde (50g, 1.56mol), nitromethane (285.6g, 4.7mol, 253mL), 2.5L of acetic acid into a 2000mL reactor and start stirring, add anhydrous potassium acetate (5g, 0.05mol ), continue to stir for 3h, then heat up and reflux for 30min. Unreacted nitromethane and solvent acetic acid were recovered by distillation under reduced pressure to obtain 139.8 g of red oil with a yield of 92.1%, which was directly carried out to the next step without purification. 1 H NMR (400MHz, CDCl 3 ): δ4.55(t, 2H, J=4.4Hz), 4.34(s, 1H), 4.14(s, 2H).

Embodiment 2

[0036] Embodiment 2: the synthetic method two of 2-nitroethanol

[0037] At room temperature, under stirring conditions, nitromethane (762.5g, 12.5mol, 675mL), paraformaldehyde (100g, 3.12mol), sodium hydroxide (3.2g, 0.08mol) were added to a 20L reactor, Methanol 8L continued to stir for 5h, then warmed to reflux for 2h. Unreacted nitromethane and solvent methanol were recovered by distillation under reduced pressure to obtain 286.6 g of a light yellow oil with a yield of 94.6%, which was directly carried out to the next step without purification.

Embodiment 3

[0038] Embodiment 3: the synthetic method one of taurine

[0039] At 20°C, add 500mL of 10% aqueous sodium hydroxide solution to a 2000mL reaction kettle, pass in sulfur dioxide gas until the pH value is 5.8, then add nitroethanol (164g, 1.8mol), stir for 18h, [concentrate to obtain nitroethyl Sodium sulfonate white solid, 1 H NMR (400MHz,D 2 O): δ4.73(t, 2H, J=4.0Hz), 3.47(t, 2H, J=4.0Hz)], add Ranney Ni20g, pass into hydrogen, wait for the reaction to be completed, separate the water layer and the catalyst, use concentrated Sulfuric acid was used to adjust the pH value to the equivalence point, and taurine was precipitated. Suction filtration and drying gave 180 g of taurine with a yield of 80% and a melting point of 319°C (dec). 1 H NMR (500MHz,D 2 O): δ3.34(t, 2H, J=5.0Hz), 3.17(t, 2H, J=5.0Hz).

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Abstract

The invention provides a novel method for preparing taurine. The method comprises the following steps: synthesizing nitroethanol by adopting nitromethane and formaldehyde as raw materials, reacting the nitroethanol with hydrosulphite, reducing, and acidizing through sulfuric acid to obtain the taurine. The method is easy in acquisition of raw materials, simple and convenient to operate and especially suitable for the industrial mass production.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and in particular relates to a new method for producing taurine by using nitromethane as a starting material. Background technique [0002] Taurine was extracted from ox bile in 1827, so it was named Taurine (a substance from ox bile) by scientists, and it was translated as taurine in China. Taurine is a sulfur-containing amino acid with a simple chemical structure, the chemical name is 2-aminoethanesulfonic acid, and the structural formula is NH2CH2CH2SO3H. It has long been considered as a non-functional terminal metabolite of sulfur-containing amino acids, and has not been taken seriously. Until 1975, reports such as Hayes that lack of taurine can cause blindness in cats, and Rfilha et al. proposed that artificially fed infants cannot maintain normal levels of taurine in blood plasma and urine due to lack of taurine. Great interest. [0003] Taurine is an important nutrient substance for hu...

Claims

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Application Information

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IPC IPC(8): C07C309/14C07C303/02
Inventor 孙华君刘年金张邦国王平张军桥
Owner HUBEI GRAND LIFE SCI & TECH CO LTD
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