Synthesis of non-cyclic amide and thioamide based ionic liquids

A method of making a non-cyclic amide or thioamide based ionic liquid comprising:

• reacting a non-cyclic amide or thioamide having a general formula:
• with a Brønsted acid HX to form an amidium or thioamidium reaction product wherein R1, R2, and R3 are independently selected from hydrogen, halide, a C1-C12 alkyl group, a C1-C12 alkenyl group, a C4-C12 cycloalkyl group, a C4-C12 cycloalkenyl group, an aryl group, a substituted C1-C12 alkyl group, a substituted C1-C12 alkenyl group, a substituted C4-C12 cycloalkyl group, a substituted C4-C12 cycloalkenyl group, a substituted aryl group, a C2-C12 ether group, or a silyl group;
• or wherein R1 is selected from hydrogen, halide, a C1-C12 alkyl group, a C1-C12 alkenyl group, a C4-C12 cycloalkyl group, a C4-C12 cycloalkenyl group, an aryl group, a substituted C1-C12 alkyl group, a substituted C1-C12 alkenyl group, a substituted C4-C12 cycloalkyl group, a substituted C4-C12 cycloalkenyl group, a substituted aryl group, a C1-C12 ether group, or a silyl group, and R2 and R3 form a C4-C12 cycloalkyl group, a C4-C12 cycloalkenyl group, a substituted C4-C12 cycloalkyl group, or a substituted C4-C12 cycloalkenyl group, wherein the substituted C1-C12 alkyl group, the substituted C1-C12 alkenyl group, the substituted C4-C12 cycloalkyl group, the substituted C4-C12 cycloalkenyl group, or the substituted aryl group is not substituted with a cyano group or a thiocyanate group;
• and
• wherein an anion in the Brønsted acid HX is a nitrate, a phosphate, a phosphinate, a phosphonate, an imide, a borate, a sulfate, a sulfonate, an acetate, a halide, a halometallate, and combinations thereof.