Imidazoline-derived compounds and use as natural gas hydrate inhibitors
Imidazoline-derived compounds are used in compositions and methods for inhibiting natural gas hydrate agglomerates. The imidazoline-derived compounds are reaction products between a tall oil fatty acid and an amine. The methods include introducing a composition downhole, the composition comprising an imidazoline-derived compound formed by reacting a tall oil fatty acid with an amine; and contacting the composition with a downhole fluid to inhibit formation of hydrate agglomerates, wherein the downhole fluid comprises natural gas or hydrocarbons.
1. A method comprising:
introducing a composition downhole, the composition comprising an imidazoline-derived compound; and
contacting the composition with a downhole fluid to inhibit formation of hydrate agglomerates, wherein the downhole fluid comprises natural gas or hydrocarbons, wherein formation of hydrate agglomerates in the downhole fluid is inhibited, and wherein the imidazoline-derived compound has the formula I or VIII::
wherein R 4 is C 1 -C 30 carbon chain (linear or branched, saturated or unsaturated), C 3 -C 8 cycloalkyl, carboxylate, or amidate;
R 1 and R 2 are independently a C 2 linker to a carboxylic acid, ester, amide, or a ring structure; R 1 is hydrogen or C 1 -C 4 alkyl and R 2 is C 1 -C 4 alkyl; or R 1 is hydrogen or —C(O)—(CH 2 )n-NH—(CH 2 ) 3 —N(butyl) 2 and R 2 is —C(O)—(CH 2 )n-NH—(CH 2 ) 3 —N(butyl) 2 ; or R 1 is hydrogen or —(CH 2 ) 3 —C(O)—NH—(CH 2 ) 3 —N(butyl) 2 and R 2 is —(CH 2 ) 3 —C(O)—NH—(CH 2 ) 3 —N(butyl) 2 ; and
R 3 is C 1 -C 10 linear or branched, saturated or unsaturated carbon chain linking the imidazoline ring to the nitrogen atom.
2. The method of claim 1 , wherein introducing is by injecting or pumping.
3. The method of claim 1 , wherein the fluid is contained in an oil or natural gas production operation or pipeline.
4. The method of claim 1 , wherein the fluid comprises water, natural gas, and liquid hydrocarbon.
5. The method of claim 1 , wherein the fluid comprises water of about 1% to about 80% weight/weight with respect to a hydrocarbon phase.
6. The method of claim 1 , wherein the composition further comprises one or more thermodynamic gas hydrate inhibitors, kinetic gas hydrate inhibitors, anti-agglomerants, asphaltene inhibitors, paraffin inhibitors, scale inhibitors, corrosion inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, or any combination thereof.
7. The method of claim 1 , wherein R 4 is derived from stearic acid, oleic acid, or a mixture of fatty acids.
8. The method of claim 1 , wherein, the imidazoline-derived compound comprises 2-(2-TOFA-1-imidazolinyl)ethyl]dibutylamine, 3-[3-(dibutylamino) propylamino]-1-[2-(2-TOFA-1-imidazolinyl)ethylamino]-1-propanone, N-dibutylaminopropylamidoethylene TOFA-imidazoline, N-amidoethylenyl dibutylaminopropylamine TOFA-imidazoline, and salts thereof.
9. A composition comprising at least one imidazoline-derived compound to inhibit formation of natural gas hydrate agglomerates, the at least one imidazoline-derived compound, has the formula I or VIII:
wherein R 4 is C 1 -C 30 carbon chain (linear or branched, saturated or unsaturated), C 3 -C 8 cycloalkyl, carboxylate, or amidate;
R 1 and R 2 are independently a C 2 linker to a carboxylic acid, ester, amide, or a ring structure; R 1 is hydrogen or C 1 -C 4 alkyl and R 2 is C 1 -C 4 alkyl; or R 1 is hydrogen or —C(O)—(CH 2 )n-NH—(CH 2 ) 3 —N(butyl) 2 and R 2 is —C(O)—(CH 2 )n-NH—(CH 2 ) 3 —N(butyl) 2 ; or R 1 is hydrogen or —(CH 2 ) 3 —C(O)—NH—(CH 2 ) 3 —N(butyl) 2 and R 2 is —(CH 2 ) 3 —C(O)—NH—(CH 2 ) 3 —N(butyl) 2 ; and
R 3 is C 1 -C 10 linear or branched, saturated or unsaturated carbon chain linking the imidazoline ring to the nitrogen atom.
10. The composition of claim 9 , wherein R 4 is derived from stearic acid, oleic acid, or a mixture of fatty acids.
11. The composition of claim 9 , wherein the at least one imidazoline-derived compound comprises 2-(2-TOFA-1-imidazolinyl)ethyl]dibutylamine, 3-[3-(dibutylamino) propylamino]-1-[2-(2-TOFA-1-imidazolinyl)ethylamino]-1-propanone, N-dibutylaminopropylamidoethylene TOFA-imidazoline, N-amidoethylenyl dibutylaminopropylamine TOFA-imidazoline, and salts thereof.
12. The composition of claim 9 , wherein concentration of the one or more imidazoline-derived compound is from about 1 wt/v % to about 80 wt/v % based on the total weight of the composition.
13. The composition of claim 9 , wherein the composition further comprises one or more thermodynamic gas hydrate inhibitors, kinetic gas hydrate inhibitors, anti-agglomerants, asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, or a combination thereof.
14. The composition of claim 9 , wherein concentration of the one or more imidazoline-derived compound is 1000 ppm to 50,000 ppm.