Multi-tail hydrate inhibitors
View Patent ↗Low-dosage hydrate inhibitor (“LDHI”) compounds comprising multiple lipophilic tails and a hydrophilic head may be employed into fluids to inhibit agglomeration of hydrates, among other things. Suitable hydrophilic heads may include quaternary or tertiary ammonium cation moieties, and combinations thereof. Such LDHI compounds in some embodiments may include reaction products of DETA and/or other amines, fatty acid(s), and, optionally, alkyl halide(s). Compounds according to some embodiments may be employed in fluids in various environments, such as a conduit penetrating a subterranean formation, or a conduit carrying fluid in an industrial setting.
1. A composition comprising:
at least one compound having the structural formula:
wherein each of R 1 and R 2 is a C 1 to C 50 hydrocarbon chain;
wherein each of R 3 and R 4 is independently selected from the group consisting of: hydrogen and a C 1 to C 10 hydrocarbon chain; and
wherein X is an anion selected from the group consisting of a bromide, a carboxylate, an organic sulfonate, a hydroxide, and any combination thereof; and
at least one solvent selected from the group consisting of: toluene, xylene, methanol, isopropyl alcohol, glycol, and any combination thereof.
2. The composition of claim 1 , wherein each of R 1 and R 2 is a C 1 to C 50 hydrocarbon chain resulting from reaction between an amine having structure H 2 N—CH 2 —NH—CH 2 —NH 2 and a fatty acid.
3. The composition of claim 2 , wherein the fatty acid is selected from the group consisting of: corn oil, canola oil, and any combination thereof.
4. The composition of claim 1 , wherein R 3 is a C 4 to C 8 hydrocarbon chain.
5. The composition of claim 1 , wherein the compound is present in the composition in an amount equal to about 0.1 to about 3.0% volume based on a water cut of the composition.
6. The composition of claim 1 , wherein the composition has a water cut of about 30% to about 50%.
7. The composition of claim 1 , wherein:
R 3 is a C 4 to C 8 hydrocarbon chain; and
X is a bromide anion.
8. A composition comprising a fluid and a low dosage hydrate inhibitor additive comprising:
at least one compound having the structural formula:
wherein each of R 1 and R 2 is a C 1 to C 50 hydrocarbon chain;
wherein each of R 3 and R 4 is independently selected from the group consisting of: hydrogen and a C 1 to C 10 hydrocarbon chain; and
wherein X is an anion selected from the group consisting of a bromide, a carboxylate, an organic sulfonate, a hydroxide, and any combination thereof; and
at least one solvent selected from the group consisting of: toluene, xylene, methanol, isopropyl alcohol, glycol, and any combination thereof.
9. The composition of claim 8 , wherein each of R 1 and R 2 is a C 1 to C 50 hydrocarbon chain resulting from reaction between an amine having structure H 2 N—CH 2 —NH—CH 2 —NH 2 and a fatty acid.
10. The composition of claim 9 , wherein the fatty acid is selected from the group consisting of: corn oil, canola oil, and any combination thereof.
11. The composition of claim 8 , wherein R 3 is a C 4 to C 8 hydrocarbon chain.
12. The composition of claim 8 , wherein the low dosage hydrate inhibitor additive is present in the composition in an amount equal to about 0.1 to about 3.0% volume based on a water cut of the composition.
13. The composition of claim 8 , wherein the composition has a water cut of about 30% to about 50%.
14. The composition of claim 8 , wherein the fluid is selected from the group consisting of: water, a gas, a liquid hydrocarbon, and any combination thereof.
15. The composition of claim 8 , wherein:
R 3 is a C 4 to C 8 hydrocarbon chain; and
X is a bromide anion.