Process for producing 4-azidosulfonylphthalic anhydride
The present disclosure provides a process for the production of 4-azidosulfonylphthalic anhydride. In an embodiment, a process is provided and includes chlorinating 4-sulfophthalic acid trisodium salt (1), under solvent reaction conditions, to form a dissolved 4-chlorosulfonylphthalic anhydride (2) and an insoluble sodium chloride. The process includes first removing the insoluble sodium chloride from the dissolved 4-chlorosulfonylphthalic anhydride to form an isolated 4-chlorosulfonylphthalic anhydride. The process includes reacting, under solvent reaction conditions, the isolated 4-chlorosulfonylphthalic anhydride with sodium azide to form a dissolved 4-azidosulfonylphthalic anhydride and an insoluble sodium chloride. The process includes second removing the insoluble sodium chloride from the dissolved 4-azidosulfonylphthalic anhydride to form an isolated 4-azidosulfonylphthalic anhydride. The process includes retrieving a solid 4-azidosulfonylphthalic anhydride (3) from the isolated 4-azidosulfonylphthalic anhydride.
1. A process comprising:
chlorinating 4-sulfophthalic acid trisodium salt (1), under solvent reaction conditions, to form a dissolved 4-chlorosulfonylphthalic anhydride (2) and an insoluble sodium chloride;
first removing the insoluble sodium chloride from the dissolved 4-chlorosulfonylphthalic anhydride to form an isolated 4-chlorosulfonylphthalic anhydride;
reacting, under solvent reaction conditions, the isolated 4-chlorosulfonylphthalic anhydride with sodium azide to form a dissolved 4-azidosulfonylphthalic anhydride and an insoluble sodium chloride;
second removing the insoluble sodium chloride from the dissolved 4-azidosulfonylphthalic anhydride to form an isolated 4-azidosulfonylphthalic anhydride; and
retrieving a solid 4-azidosulfonylphthalic anhydride (3) from the isolated 4-azidosulfonylphthalic anhydride.
2. The process of claim 1 wherein the chlorinating comprises reacting the 4-sulfophthalic acid trisodium salt with a chlorinating agent in toluene solvent and in the presence of dimethylformamide.
3. The process of claim 1 wherein the first removing comprises filtering the insoluble sodium chloride from the dissolved 4-chlorosulfonyl anhydride.
4. The process of claim 2 wherein the dissolved 4-chlorosulfonylphthalic anhydride (2) in toluene solvent is a liquid non-aqueous phase, and the first removing comprises:
adding water to dissolve the insoluble sodium chloride in a liquid aqueous phase; and
separating the liquid aqueous phase from the liquid nonaqueous phase.
5. The process of claim 1 wherein the reacting step comprises adding the sodium azide directly to the isolated 4-chlorosulfonylphthalic anhydride.
6. The process of claim 1 comprising performing the process in a single reaction vessel.
7. The process of claim 6 wherein the chlorinating occurs in a solvent under solvent reaction conditions and the isolated 4-chlorosulfonylphthalic anhydride remains dissolved in the solvent.
8. The process of claim 7 wherein the reacting step occurs in the solvent under solvent reaction conditions and the isolated 4-azidosulfonylphthalic anhydride remains dissolved in the solvent.
9. The process of claim 8 wherein the reacting step comprises adding aqueous sodium azide to the isolated 4-chlorosulfonylphthalic anhydride in toluene solvent.
10. The process of claim 9 wherein the reacting step comprises adding aqueous sodium azide comprising from 5 wt % to 60 wt % sodium azide, based on the total weight of the aqueous sodium azide, to the isolated 4-chlorosulfonylphthalic anhydride in toluene solvent.
11. The process of claim 10 wherein the chlorinating comprises reacting the 4-sulfophthalic acid trisodium salt with a chlorinating agent comprising oxalyl chloride, in toluene solvent and in the presence of dimethylformamide.
12. A process comprising:
chlorinating 4-sulfophthalic acid trisodium salt (1), in toluene under solvent reaction conditions, to form a dissolved 4-chlorosulfonylphthalic anhydride (2) and an insoluble sodium chloride;
first removing the insoluble sodium chloride from the dissolved 4-chlorosulfonylphthalic anhydride to form an isolated 4-chlorosulfonylphthalic anhydride that remains dissolved in the toluene;
reacting, in toluene under solvent reaction conditions, the isolated 4-chlorosulfonylphthalic anhydride with aqueous sodium azide to form a dissolved 4-azidosulfonylphthalic anhydride and an insoluble sodium chloride;
second removing the insoluble sodium chloride from the dissolved 4-azidosulfonylphthalic anhydride to form an isolated 4-azidosulfonylphthalic anhydride that remains dissolved in the toluene;
retrieving a solid 4-azidosulfonylphthalic anhydride (3) from the isolated 4-azidosulfonylphthalic anhydride.
13. The process of claim 12 comprising performing the chlorinating, first removing, reacting, and second removing in a single reaction vessel.
14. The process of claim 13 wherein the chlorinating comprises reacting the 4-sulfophthalic acid trisodium salt with a chlorinating agent in toluene solvent.
15. The process of claim 14 wherein the reacting step comprises adding the aqueous sodium azide to the isolated 4-chlorosulfonylphthalic anhydride in toluene solvent.
16. The process of claim 15 wherein the dissolved 4-chlorosulfonylphthalic anhydride (2) in toluene solvent is a liquid non-aqueous phase, and the first removing comprises:
adding water to dissolve the insoluble sodium chloride in a liquid aqueous phase; and
separating the liquid aqueous phase from the liquid nonaqueous phase, wherein the 4-chlorosulfonylphthalic anhydride remains dissolved in the liquid nonaqueous phase.
17. The process of claim 16 wherein the chlorinating comprises reacting the 4-sulfophthalic acid trisodium salt with a chlorinating agent comprising oxalyl chloride, in toluene solvent and in the presence of dimethylformamide.