US 12,168,751 B2
Imidazoline-derived compounds and use as natural gas hydrate inhibitors
Jeremy Wayne Bartels, Sugar Land, TX (US); Kousik Kundu, Sugar Land, TX (US); and Jeff Michael Servesko, Sugar Land, TX (US)
Assigned to ChampionX LLC, Sugar Land, TX (US)
Appl. No. 18/003,035
Filed by ChampionX LLC, Sugar Land, TX (US)
PCT Filed Jun. 24, 2021, PCT No. PCT/US2021/038902
§ 371(c)(1), (2) Date Dec. 22, 2022,
PCT Pub. No. WO2021/262981, PCT Pub. Date Dec. 30, 2021.
Claims priority of provisional application 63/044,087, filed on Jun. 25, 2020.
Prior Publication US 2023/0250329 A1, Aug. 10, 2023
Int. Cl. C09K 8/52 (2006.01); E21B 37/06 (2006.01); E21B 43/22 (2006.01)
CPC C09K 8/52 (2013.01) [E21B 37/06 (2013.01); C09K 2208/22 (2013.01)] 14 Claims
OG exemplary drawing
 
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::

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein R4 is C1-C30 carbon chain (linear or branched, saturated or unsaturated), C3-C8 cycloalkyl, carboxylate, or amidate;
R1 and R2 are independently a C2 linker to a carboxylic acid, ester, amide, or a ring structure; R1 is hydrogen or C1-C4 alkyl and R2 is C1-C4 alkyl; or R1 is hydrogen or —C(O)—(CH2)n-NH—(CH2)3—N(butyl)2 and R2 is —C(O)—(CH2)n-NH—(CH2)3—N(butyl)2; or R1 is hydrogen or —(CH2)3—C(O)—NH—(CH2)3—N(butyl)2 and R2 is —(CH2)3—C(O)—NH—(CH2)3—N(butyl)2; and
R3 is C1-C10 linear or branched, saturated or unsaturated carbon chain linking the imidazoline ring to the nitrogen atom.