Oxazolidinium compounds and use as hydrate inhibitors
View Patent ↗Oxazolidinium compounds are formed by the reaction of a halohydrin or an epoxide with a secondary amine and an aldehyde or a ketone. The oxazolidinium compounds are formed directly and do not require the reaction of a pre-formed oxazolidine with an alkylating agent. The compounds are useful as gas hydrate inhibitors in oil and gas production and transportation.
1. A method for preparing a mixture of oxazolidinium compounds, the method comprising reacting an aldehyde and/or a ketone with a secondary amine and a reactant selected from the group consisting of a halohydrin and an epoxide, under reaction conditions sufficient to produce a mixture of oxazolidinium compounds, where at least one oxazolidinium compound in the mixture has the formula:
where R is a hydrocarbon substituent containing from 1 to 20 carbon atoms, a hydrocarbon substituent containing from 1 to 20 carbon atoms substituted with a heteroatom selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof; R 1 and R 2 each independently have 1 to 20 carbon atoms, may be linear, branched or cyclic; linear, branched or cyclic groups having 1 to 20 carbon atoms substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups, and X is selected from the group consisting of chlorine, fluorine, bromine or iodine.
2. The method of claim 1 where the aldehyde has from 1 to 20 carbon atoms and the ketone has from 3 to 20 carbon atoms.
3. The method of claim 1 where the halohydrin has the formula:
wherein X is selected from the group consisting of chlorine, fluorine, bromine or iodine; and wherein R A , R B , R C and R D are each independently selected from the group consisting of hydrogen, hydrocarbon substituents containing from 1 to 20 carbon atoms, and heteroatoms selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof.
4. The method of claim 1 where the secondary amine has from 2 to 20 carbon atoms, may be linear, branched or cyclic and may be substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups.
5. The method of claim 1 where the reaction conditions comprise a temperature ranging from about ambient to about 120° C., and a pressure ranging from about ambient to that required to keep the reactants and solvents in the liquid phase.
6. A method for preparing a mixture of oxazolidinium compounds, the method comprising reacting an aldehyde having from 1 to 20 carbon atoms and/or a ketone having from 3 to 20 carbon atoms with a secondary amine and a reactant selected from the group consisting of a halohydrin and an epoxide, at a temperature ranging from about ambient to about 120° C., and a pressure ranging from about ambient to that required to keep the reactants and solvents in the liquid phase to produce a mixture of oxazolidinium compounds, where at least one oxazolidinium compound having the formula:
where R is a hydrocarbon substituent containing from 1 to 20 carbon atoms, a hydrocarbon substituent containing from 1 to 20 carbon atoms substituted with a heteroatom selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof; R 1 and R 2 each independently have 1 to 20 carbon atoms, may be linear, branched or cyclic; linear, branched or cyclic groups having 1 to 20 carbon atoms substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups, and X is selected from the group consisting of chlorine, fluorine, bromine or iodine.
7. The method of claim 6 where the halohydrin has the formula:
wherein X is chlorine, fluorine, bromine or iodine; and wherein R A , R B , R C and R D are each independently selected from the group consisting of hydrogen, hydrocarbon substituents containing from 1 to 20 carbon atoms, and heteroatoms selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof.
8. The method of claim 6 where the secondary amine has from 2 to 20 carbon atoms, may be linear, branched or cyclic and may be substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups.
9. A mixture of oxazolidinium compounds prepared by a method comprising reacting an aldehyde and/or a ketone with a secondary amine and a reactant selected from the group consisting of a halohydrin and an epoxide, under reaction conditions sufficient to produce a mixture of oxazolidinium compounds, where at least one oxazolidinium compound in the mixture has the formula:
where R is a hydrocarbon substituent containing from 1 to 20 carbon atoms substituted with a heteroatom selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof; R 1 and R 2 each independently have 1 to 20 carbon atoms, may be linear, branched or cyclic; linear, branched or cyclic groups having 1 to 20 carbon atoms substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups, and X is selected from the group consisting of chlorine, fluorine, bromine or iodine.
10. The mixture of oxazolidinium compounds of claim 9 where the aldehyde has from 1 to 20 carbon atoms and the ketone has from 3 to 20 carbon atoms.
11. The mixture of oxazolidinium compounds of claim 9 where the halohydrin has the formula:
wherein X is selected from the group consisting of chlorine, fluorine, bromine or iodine; and wherein R A , R B , R C and R D are each independently selected from the group consisting of hydrogen, hydrocarbon substituents containing from 1 to 20 carbon atoms, and heteroatoms selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof.
12. The mixture of oxazolidinium compounds of claim 9 where the secondary amine has from 2 to 20 carbon atoms, may be linear, branched or cyclic and may be substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups.
13. The mixture of oxazolidinium compounds of claim 9 where the reaction conditions comprise a temperature ranging from about ambient to about 120° C., and a pressure ranging from about ambient to that required to keep the reactants and solvents in the liquid phase.
14. An oxazolidinium compound having the structure:
where R is a hydrocarbon substituent containing from 1 to 20 carbon atoms substituted with a heteroatom selected from the group consisting of oxygen, nitrogen, phosphorus and combinations thereof; R 1 and R 2 each independently have 1 to 20 carbon atoms, may be linear, branched or cyclic; linear, branched or cyclic groups having 1 to 20 carbon atoms substituted with alkyl groups, aryl groups, alkylaryl groups, and aryl groups substituted with alkoxy groups, and X is selected from the group consisting of chlorine, fluorine, bromine or iodine.