CN101260070A - Method for preparing taurine - Google Patents

Abstract

The invention discloses a preparation method for taurine which comprises the following steps that: 1. ethylene thioglycol is oxidized by oxidizer in the solvent to prepare hydroxyethylsulfonate; 2. the hydroxyethylsulfonate is reacted with ammonia to prepare taurine. The preparation method for taurine of the invention has short process route and low cost. The first-step oxidation reaction has mild conditions, can be made at normal temperature and has low energy consumption. The total reaction process has no waste liquid and waste residue, and no escape of sulfur dioxide gas, so the production environment is good. Compared with the prior commonly used method, the preparation method is more clean, can reduce large power consumption and manpower consumption, and the reaction yield can be improved by 20 percent compared with the general process.

Description

A kind of preparation method of taurine

Technical field

The invention belongs to the organic chemistry synthesis technical field, be specifically related to a kind of preparation method of taurine.

Background technology

Taurine (Taurine) claim taurocholic acid again; it is a kind of sulfur-bearing nonprotein amino acid; chemistry 2-aminoethyl sulfonic acid by name; in recent years along with further investigation to taurine physiological action, nutritive value; its application is also more and more wider, at aspects such as medicine, food, fuel, tensio-active agent, pH buffer reagents important use is arranged all.Taurine can be used for cholagogic, protects the liver, detoxifcation, anti-inflammatory, analgesic, calm, anticonvulsion, anti-heart disorder, treatment Cardiac Insufficiency, regulates osmotic pressure, brings high blood pressure down, treats arteriosclerosis, suppresses nervus centralis, keeps eyesight etc. as medicine.Some developed country in the world at present, oneself has added an amount of taurine in the milk of supplying with consumption by infants and milk powder as the U.S., Japan, guarantees infant's health and normal development with this.There were many enterprises in China over the past two years for the attention to infant development, had developed a series of commodity that contain taurine.Modern study shows that taurine also has the function of a series of uniquenesses to adult cardiovascular systems, have build up health, preventing disease, relieving fatigue, the effect of improving work efficiency.

Taurine is since finding, people are just constantly exploring the approach of its synthetic.So far, the synthetic method of relevant taurine is not descended tens of kinds.The chemical synthesis that obtains taurine at present mainly contains following three kinds:

1, dichloroethane law:

Ethylene dichloride and S-WAT reaction obtain 2-one chloroethene sodium sulfonate, and it obtains 2-aminoethyl sulfonic acid sodium with ammonia react under heating and pressurizing, make taurine with hcl acidifying again, and chemical equation is as follows:

ClCH ₂CH ₂Cl+Na ₂SO ₃→ClCH ₂CH ₂SO ₃Na+NaCl

ClCH ₂CH ₂SO ₃Na+NH ₃→NH ₂CH ₂CH ₂SO ₃Na+NH ₄Cl

NH ₂CH ₂CH ₂SO ₃Na+HCl→NH ₂CH ₂CH ₂SO ₃H+NaCl

These method raw materials for production are many, and production stage is many, and by product is many, the cost height, and under heating and pressurizing, react, so full scale plant cost height.

2, epoxyethane method:

The reaction of oxyethane and sodium bisulfite makes 2-ethylenehydrinsulfonic acid sodium, and it makes 2-aminoethyl sulfonic acid sodium adding to depress with ammonia react, makes taurine with hcl acidifying again, and chemical equation is as follows:

HOCH ₂CH ₂SO ₃Na+NH ₃→NH ₂CH ₂CH ₂SO ₃Na+H ₂O

NH ₂CH ₂CH ₂SO ₃Na+HCl→NH ₂CH ₂CH ₂SO ₃H+NaCl

This method is reacted under heating and pressurizing, full scale plant cost height.

3, S-WAT is a reductive agent reduction thanomin sulfuric ester method:

With the thanomin is raw material, and two steps are synthetic, can be divided into esterification process, chlorination process, imines method again by synthetic route.Wherein because of raw material is easy to get, yield is higher than additive method to esterification process (also claiming esterification reduction method, sulfuric acid process), and becomes domestic and international most producers first-selection, and its chemical equation is as follows:

NH ₂CH ₂CH ₂OH+H ₂SO ₄→NH ₂CH ₂CH ₂OSO ₃H+H ₂O

NH ₂CH ₂CH ₂OSO ₃H+Na ₂SO ₃→NH ₂CH ₂CH ₂SO ₃H+Na ₂SO ₄

This method is divided into following a few step again in actual industrial chemical industry journey:

(1) salify:

NH ₂CH ₂CH ₂OH+H ₂SO ₄→NH ₂CH ₂CH ₂OH·H ₂SO ₄

Decompression

(2) esterification:

NH ₂CH ₂CH ₂OH·H ₂SO ₄→NH ₂CH ₂CH ₂OSO ₃H+H ₂O

Dehydration

(3) reduction:

NH ₂CH ₂CH ₂OSO ₃H+Na ₂SO ₃→NH ₂CH ₂CH ₂SO ₃H+Na ₂SO ₄

In above-mentioned three-step reaction, following side reaction is arranged:

(1) hydrolysis of ester:

NH ₂CH ₂CH ₂OSO ₃H+H ₂O→NH ₂CH ₂CH ₂OH·H ₂SO ₄

(2) the intermolecular dehydration of ester:

2NH ₂CH ₂CH ₂OSO ₃H→NH ₂CH ₂CH ₂OSO ₂NHCH ₂OSO ₃H+H ₂O

(3) Na ₂SO ₃Oxidation:

2Na ₂SO ₃+O ₂→2Na ₂SO ₄

(4) Na ₂SO ₃Hydrolysis:

Na ₂SO ₃+H ₂O→NaHSO ₃+NaOH

NaHSO ₃+H ₂O→H ₂SO ₃+NaOH

H ₂SO ₃→SO ₂+H ₂O

No matter hydrolysis reaction still all easily takes place at alkaline environment at sour environment in thanomin sodium sulfate, for this reason, above-mentioned acidulants will be adjusted to neutrality (pH=7) before the reduction reaction.Existing many producers (comprising the laboratory) all adopt soda ash (Na ₂CO ₃) the solution adjusting, chemical equation is as follows:

Na ₂CO ₃+H ₂SO ₄→Na ₂SO ₄+CO ₂+H ₂O

This method is difficult control in actual production process; be difficult to accurately measure potential of hydrogen; it is excessive that soda ash is added; more cumbersome is separating of taurine and sodium sulfate; because sodium sulfate is in the little characteristic of high-temperature digestion degree; need at high temperature separate taurine and sodium sulfate (saltcake), simultaneously again with a large amount of SO ₂Gas makes production environment very abominable.

This technology also exists in aqueous phase heating and cooling step many, and the time is long, causes taurine to decompose, and side reaction takes place.A large amount of taurines is carried secretly in the removal process of sodium sulfate in addition, and rate of loss is big.

Summary of the invention

Technical problem to be solved by this invention is the taurine preparation technology that a kind of yield height will be provided, clean.

For solving the problems of the technologies described above, the technical solution adopted in the present invention is as follows:

A kind of preparation method of taurine, this method comprises the steps:

1, hydroxyethyl mercaptan prepares hydroxyethylsulfonic acid through the oxygenant oxidation in solvent;

2, hydroxyethylsulfonic acid and ammonia react prepare taurine.

In the step 1, temperature of reaction is 10～40 ℃, preferred 25～30 ℃; Described solvent is a water, or the mixed solution of water and other mutual solvents; The reaction mol ratio of hydroxyethyl mercaptan and oxygenant is 1: 3～10, preferred 1: 3～6, and more preferably 1: 4; Described oxygenant is a superoxide, preferred hydrogen peroxide, Peracetic Acid or benzoyl hydroperoxide, more preferably hydrogen peroxide; Reaction times is 3～10 hours.

In the step 2, temperature of reaction is 250～300 ℃; The reaction mol ratio of hydroxyethylsulfonic acid and ammonia is 1: 10～20; Reaction times is 2～5 hours.

Reaction equation is as follows:

Beneficial effect: the preparation method of taurine of the present invention, operational path is short, and cost is low.The first step oxidation reaction condition gentleness can be reacted under the normal temperature, and energy consumption is low.Overall process does not have waste liquid, waste residue to produce, and no sulfur dioxide gas escapes, so production environment is good.Compare more cleaning with former method commonly used, can reduce a large amount of power consumptions and manpower consumption, and reaction yield can improve 20% than general technology.

Embodiment:

Embodiment 1:

Under 30 ℃, add 12% hydrogen peroxide (4mol) of 78g (1mol) hydroxyethyl mercaptan and 1133g in the 2000mL autoclave pressure, sealing back stirring reaction 3 hours gets hydroxyethylsulfonic acid solution after reaction finishes.

Add 11mol ammonia in the hydroxyethylsulfonic acid solution (containing the 1mol hydroxyethylsulfonic acid) of above gained, this solution is added in the pressure reactor, reaction is 5 hours under 260 degree, reduces to room temperature, and dripping hydrochloric acid is to separating out solid, and filtration drying gets the 100.2g taurine.

Embodiment 2:

Under 25 ℃, in the 2000mL autoclave pressure, add 78g (1mol) hydroxyethyl mercaptan and 342g (4.5mol) Peracetic Acid, adding 1000mL water, sealing back stirring reaction 6 hours gets hydroxyethylsulfonic acid solution after reaction finishes.

Add 15mol ammonia in the hydroxyethylsulfonic acid solution (containing the 1mol hydroxyethylsulfonic acid) of above gained, this solution is added in the pressure reactor, at 280 degree, reacted 3 hours, reduce to room temperature, dripping hydrochloric acid is to separating out solid, and filtration drying gets the 105.6g taurine.

Embodiment 3:

Under 20 ℃, in the 2000mL autoclave pressure, add the benzoyl hydroperoxide of 78g (1mol) hydroxyethyl mercaptan and 753g (5.5mol), adding 700mL water and 50mL DMF, sealing back stirring reaction 8 hours gets hydroxyethylsulfonic acid solution after reaction finishes.

Add 19mol ammonia in the hydroxyethylsulfonic acid solution (containing the 1mol hydroxyethylsulfonic acid) of above gained, this solution is added in the pressure reactor, reaction is 2 hours under 300 degree, reduces to room temperature, and dripping hydrochloric acid is to separating out solid, and filtration drying gets the 101.2g taurine.

Embodiment 4:

Method with embodiment 3 is identical, and different is under 10 ℃, adds the benzoyl hydroperoxide of 78g (1mol) hydroxyethyl mercaptan and 411g (3mol) in the 2000mL autoclave pressure, adds 700mL water and 50mL DMF, sealing back stirring reaction 10 hours.

Embodiment 5:

Method with embodiment 3 is identical, and different is under 40 ℃, adds the benzoyl hydroperoxide of 78g (1mol) hydroxyethyl mercaptan and 1369g (10mol) in the 2000mL autoclave pressure, adds 700mL water and 50mL DMF, sealing back stirring reaction 6 hours.

Embodiment 6:

Method with embodiment 3 is identical, adds 10mol ammonia in the hydroxyethylsulfonic acid solution (containing the 1mol hydroxyethylsulfonic acid) that different is to gained, and this solution is added in pressure reactor, and reaction is 4 hours under 250 degree.

Embodiment 7:

Method with embodiment 3 is identical, adds 20mol ammonia in the hydroxyethylsulfonic acid solution (containing the 1mol hydroxyethylsulfonic acid) that different is to gained.

Claims (10)

1, a kind of preparation method of taurine is characterized in that this method comprises the steps:

(1) hydroxyethyl mercaptan prepares hydroxyethylsulfonic acid through the oxygenant oxidation in solvent;

(2) hydroxyethylsulfonic acid and ammonia react prepare taurine.

2, the preparation method of taurine according to claim 1 is characterized in that in the step (1), temperature of reaction is 10～40 ℃.

3, the preparation method of taurine according to claim 1 is characterized in that in the step (1), described solvent is a water, or the mixed solution of water and other mutual solvents.

4, the preparation method of taurine according to claim 1 is characterized in that in the step (1), the reaction mol ratio of hydroxyethyl mercaptan and oxygenant is 1: 3～10.

5,, it is characterized in that in the step (1), described oxygenant is a superoxide according to the preparation method of claim 1 or 4 described taurines.

6, the preparation method of taurine according to claim 5 is characterized in that in the step (1), described oxygenant is hydrogen peroxide, Peracetic Acid or benzoyl hydroperoxide.

7, the preparation method of taurine according to claim 1 is characterized in that in the step (1), the reaction times is 3～10 hours.

8, the preparation method of taurine according to claim 1 is characterized in that in the step (2), temperature of reaction is 250～300 ℃.

9, the preparation method of taurine according to claim 1 is characterized in that in the step (2), the reaction mol ratio of hydroxyethylsulfonic acid and ammonia is 1: 10～20.

10, the preparation method of taurine according to claim 1 is characterized in that in the step (2), the reaction times is 2～5 hours.