Oxazolidinium compounds and use as hydrate inhibitors
AssigneeBaker Hughes Incorporated
InventorsGordon T. Rivers, Jun Tian, James A. Hackerott
Life of this patent
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Abstract
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.
Claims14
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;
- R1 and R2 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.
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;
- R1 and R2 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.
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;
- R1 and R2 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.
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;
- R1 and R2 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.
Dependencies are inferred from the claim text.