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Preparation of N-[Tris(hydroxymethyl)methyl]-3-aminopropanesulfonic acid (TAPS)

2022-02-15 10:17:14

TAPS is a widely used zwitterionic buffer in the fields of biochemistry and molecular biology with pH buffer range from 7.7 to 9.1, and is soluble in water (25g/50ml). It can be used as biobuffer in clinical diagnosis, such as biochemical diagnosis kits, DNA/RNA extraction kits, and PCR diagnostic kits. The molecular structure of TAPS is as follows:

TAPS molecular structure

At present, there are few reports on the synthesis of TAPS. Chen Guixi et al. [1] studied the synthesis method of TAPS in detail. They used Tris and 1, 3-propane sultone (1, 3-PS) as raw materials, and alcoholic substances as solvents. The main reaction formulas are as follows:


TAPS synthesis route

Concrete steps: Weigh equimolar amounts of Tris and 1,3-PS, and take the appropriate amount of alcohol as solvent into a 250 ml three-necked flask with condensation reflux. Under stirring, heat up and reflux; the reaction is terminated after reacting for a period of time. At room temperature, the reaction solution was allowed to cool to room temperature, and then vacuum filtration. Coarse TAPS filter cake washed with an appropriate amount of anhydrous ethanol 2 ~ 3 times, took the TAPS filter cake and placed in a vacuum drying oven. And the obtained filtered filtrate using vacuum pump was used for recovery.


During the synthesis, the reaction time, different alcohol solvents and cyclic utilization of reaction solvents have an effect on the yield and purity of TAPS. The experimental results show that the reaction time is controlled at 6 hours, the yield is the highest, reaching 70.3%, and the reaction time is prolonged, the yield is slightly decreased; for the investigated ethanol, n-propanol, isopropanol and n-butanol as solvent, n-butanol gives the highest yield (70.3%) and purity (94.36%) of TAPS. During the reaction, the cyclic utilization of reaction solvent was beneficial to increase the yield and purity of TAPS.


In summary, the synthesis of TAPS using Tris and 1, 3-PS as raw materials, the optimal reaction is the time controlled at 6 hours; n-butanol as the solvent and cyclic utilization.


References:

[1]Chen Guixi, Xia Xiaozhong, et al., Studies on the synthesis of N-[tris(hydroxymethyl)]-3-aminopropanesulfonic acid, Chemical World, 2010, 9, 559


Edited by Suzhou Yacoo Science Co. Ltd


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