Halide-mediated dealkylation of phosphotriesters
In one embodiment, a method includes contacting a phosphotriester and a halogen salt in a polar solvent. In another embodiment, a method for dealkylating tributylphosphate includes contacting tributylphosphate and a halogen salt in a polar solvent.
1. A method, comprising:
contacting a phosphotriester and a halogen salt in a polar solvent.
2. The method of claim 1 , wherein the phosphotriester is tributylphosphate.
3. The method of claim 2 , wherein the contacting results in conversion of the tributylphosphate to dibutylphosphate and monobutylphosphate.
4. The method of claim 1 , wherein the phosphotriester is a flame retardant.
5. The method of claim 1 , wherein the phosphotriester is a lubricant.
6. The method of claim 1 , wherein the phosphotriester is present in a mixture comprising the phosphotriester and a nonpolar solvent, wherein the mixture is contacted with the halogen salt in the polar solvent.
7. The method of claim 1 , wherein a halide component of the halogen salt is an iodide.
8. The method of claim 1 , wherein the halogen salt is present in at least a 1:1 molar ratio relative to the phosphotriester.
9. The method of claim 1 , wherein the halogen salt is present in at least a 2:1 molar ratio relative to the phosphotriester.
10. The method of claim 1 , wherein the halogen salt includes a Group I or Group II, or a transition metal, or a polyatomic cation.
11. The method of claim 1 , wherein the polar solvent is dimethylsulfoxide (DMSO).
12. The method of claim 1 , wherein the polar solvent is an organic solvent.
13. The method of claim 1 , wherein the polar solvent is water.
14. The method of claim 1 , wherein the contacting is conducted at a temperature below a boiling point of the polar solvent.
15. The method of claim 1 , wherein the phosphotriester is present in a nonpolar solvent during the contacting with the halogen salt in the polar solvent.
16. The method of claim 1 , wherein the phosphotriester is tributylphosphate, wherein the contacting results in a chemical reaction as follows:
where X is a halide, and Y is a metal or polyatomic cation.
17. A method for dealkylating tributylphosphate, the method comprising:
contacting tributylphosphate and a halogen salt in a polar solvent.
18. The method of claim 17 , wherein the polar solvent is dimethylsulfoxide (DMSO).
19. The method of claim 17 , wherein a halide component of the halogen salt is an iodide.
20. The method of claim 17 , wherein the halogen salt is present in at least a 1:1 molar ratio relative to the tributylphosphate.
21. The method of claim 17 , wherein the contacting is conducted at a temperature below a boiling point of the polar solvent.