Method for producing N-(hydrocarbon)isocyanuric acid
A novel production method enables selective production of an isocyanuric acid N-substituted product of interest in one pot, requiring neither multiple steps nor cumbersome treatment, the method producing an N-(hydrocarbon)isocyanuric acid which includes a step N for reacting, in a solvent, a dihalogenated isocyanuric acid derivative with at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound.
1. A method for producing an N-(hydrocarbon)isocyanuric acid, the method comprising:
a step N of reacting, in a solvent, at least one dihalogenated isocyanuric acid derivative selected from the group consisting of a dihalogenated isocyanuric acid, a dihalogenated isocyanuric acid salt, and a dihalogenated isocyanuric acid salt hydrate with at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound.
2. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 1 , wherein:
the step N comprises a step X of providing a solution or dispersion of at least one dihalogenated isocyanuric acid derivative selected from the group consisting of a dihalogenated isocyanuric acid, a dihalogenated isocyanuric acid salt, and a dihalogenated isocyanuric acid salt hydrate, and
a step Y of mixing the solution or dispersion of the dihalogenated isocyanuric acid derivative with at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound; or comprises
a step S of providing a solution or dispersion of at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound, and
a step T of mixing the solution or dispersion of the hydrocarbonization agent with at least one dihalogenated isocyanuric acid derivative selected from the group consisting of a dihalogenated isocyanuric acid, a dihalogenated isocyanuric acid salt, and a dihalogenated isocyanuric acid salt hydrate.
3. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 2 , wherein the solution or dispersion of the dihalogenated isocyanuric acid derivative is an aqueous solution or an aqueous dispersion.
4. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 3 , wherein the aqueous solution or aqueous dispersion of the dihalogenated isocyanuric acid derivative contains water at a mixing ratio (by mass) of the water to the solvent of 0.1:99.9 to 99.9:0.1.
5. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 2 , wherein the step Y is a step of mixing the solution or dispersion of the dihalogenated isocyanuric acid derivative with at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound, and with a surfactant.
6. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 5 , wherein the surfactant contains at least one selected from the group consisting of a quaternary ammonium salt, a crown ether, and an alkylbenzenesulfonic acid salt.
7. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 2 , wherein the step X is a step of providing a solution or dispersion containing at least one dihalogenated isocyanuric acid derivative selected from the group consisting of a dihalogenated isocyanuric acid, a dihalogenated isocyanuric acid salt, and a dihalogenated isocyanuric acid salt hydrate, and a base.
8. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 7 , wherein the base contains an inorganic base.
9. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 2 , wherein the solution or dispersion of the hydrocarbonization agent is an aqueous solution or an aqueous dispersion.
10. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 9 , wherein the aqueous solution or aqueous dispersion of the hydrocarbonization agent contains water at a mixing ratio (by mass) of the water to the solvent of 0.1:99.9 to 99.9:0.1.
11. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 2 , wherein the step S is a step of providing a solution or dispersion containing at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound, and a surfactant.
12. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 11 , wherein the surfactant contains at least one selected from the group consisting of a quaternary ammonium salt, a crown ether, and an alkylbenzenesulfonic acid salt.
13. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 2 , wherein the step S is a step of providing a solution or dispersion containing at least one hydrocarbonization agent selected from the group consisting of a halogenated hydrocarbon compound, a pseudo-halogenated hydrocarbon compound, and a dialkyl sulfate compound, and a base.
14. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 13 , wherein the base contains an inorganic base.
15. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 1 , wherein the hydrocarbonization agent contains at least one selected from the group consisting of methyl p-toluenesulfonate, ethyl p-toluenesulfonate, methyl methanesulfonate, ethyl methanesulfonate, dimethyl sulfate, and diethyl sulfate.
16. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 15 , wherein the hydrocarbonization agent contains at least one selected from the group consisting of dimethyl sulfate and diethyl sulfate.
17. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 1 , wherein the dihalogenated isocyanuric acid derivative contains at least one selected from the group consisting of dichloroisocyanuric acid, sodium dichloroisocyanurate, and sodium dichloroisocyanurate dihydrate.
18. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 17 , wherein the dihalogenated isocyanuric acid derivative contains sodium dichloroisocyanurate.
19. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 1 , wherein the amount of the hydrocarbonization agent is 0.3 mole equivalent to 4.0 mole equivalent relative to 1 mole equivalent of the dihalogenated isocyanuric acid derivative.
20. The method for producing an N-(hydrocarbon)isocyanuric acid according to claim 1 , wherein the amount of the dihalogenated isocyanuric acid derivative is 0.03 to 0.3 times by mass that of the solvent used.