Bis-(1(2)H-tetrazol-5-yl) amine and production method therefor
High-quality bis-(1(2)H-tetrazol-5-yl)amine and a method for easily, safely, and inexpensively producing the compound are provided. The method for producing bis-(1(2)H-tetrazol-5-yl)amine includes the steps of heating to 50 to 120° C. a solution mixture in which a necessary amount of an azide salt and a dicyanamide salt in an amount corresponding to 1 to 80 wt % of a necessary amount are added to a solvent, adding an acid in an amount of 1.54 to 2.22 chemical equivalents of the dicyanamide salt in the solution mixture to carry out a reaction at 50 to 120° C., and then adding an acid and a dicyanamide salt solution in which the remaining dicyanamide salt is dissolved in a solvent to promote the reaction. Bis-(1(2)H-tetrazol-5-yl)amine is obtained according to the production method.
1. A method for producing bis-(1(2)H-tetrazol-5-yl)amine ammonium salt comprising the steps of:
heating to 50 to 120° C. a solution mixture in which an azide salt in a necessary amount and a dicyanamide salt in an amount corresponding to 1 to 80 wt% of a necessary amount are added to a solvent,
adding an acid in an amount of 1.54 to 2.22 chemical equivalents of the dicyanamide salt in the solution mixture to carry out a reaction at 50 to 120° C,
adding an acid and a dicyanamide salt solution in which remaining dicyanamide salt is dissolved in a solvent to promote the reaction,
heat-treating at 75° C. or greater the obtained metal salt compound,
adding a solution of a second acid to form at least one of bis-(1(2)H-tetrazol-5-yl)amine anhydrate and monohydrate, and
adding an amine to the obtained at least one of bis-(1(2)H-tetrazol-5-yl)amine anhydrate and monohydrate to convert the at least one of bis-(1(2)H-tetrazol-5-yl)amine anhydrate and monohydrate into bis-(1(2)H-tetrazol- 5 -yl)amine ammonium salt,
wherein the bis-(1(2)H-tetrazol-5-yl)amine ammonium salt has a purity of 99.0 wt% or greater on a weight basis and not showing a peak accounting for 0.1 wt% or greater on a weight basis within a relative retention time starting at 2.17 and ending at 2.24 assuming that a retention time to a main peak is 1 as determined according to an area percentage obtained by HPLC analysis,
provided that HPLC analysis conditions include:
detection with UV220 nm,
a column of Inertsil ODS-3 having 4.6 mm ID×250 mm,
a column bath temperature of 30° C.,
a mobile phase of:
solution A: 0.1% phosphoric acid solution/acetonitrile/methanol in a ratio of 950/25/25, and
solution B: 0.1% phosphoric acid solution/acetonitrile in a ratio of 400/600,
a gradient program of:
0-30 minutes: 100-50% solution A, 0-50% solution B,
30-60 minutes: 50% solution A, 50% solution B;
a mobile phase flow rate of 1.0 mL/min, and
an amount of a sample injected of 20 μL (loop).