	US 11,898,091 B2
	Synergistic blends of anti-agglomerant gas hydrate inhibitors with quaternary benzyl ammonium compounds
Dirk Leinweber, Kelkheim (DE); Zachary Thomas Ward, Spring, TX (US); Felix Hoevelmann, Mühldorf (DE); Jonathan James Wylde, The Woodlands, TX (US); and Matthias Krull, Harxheim (DE)
Assigned to CLARIANT INTERNATIONAL LTD, Muttenz (CH)
Filed by Clariant International, Ltd., Muttenz (CH)
Filed on Nov. 16, 2020, as Appl. No. 17/099,233.
Claims priority of provisional application 62/946,679, filed on Dec. 11, 2019.
Prior Publication US 2021/0179918 A1, Jun. 17, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C09K 8/52 (2006.01); C10L 1/222 (2006.01); C10L 3/10 (2006.01); C07D 207/404 (2006.01)

CPC C09K 8/52 (2013.01) [C07D 207/404 (2013.01); C10L 1/2222 (2013.01); C10L 3/107 (2013.01); C09K 2208/22 (2013.01)]

31 Claims

1. A method for inhibiting the formation of gas hydrate agglomerates and plugs, the method comprising bringing a system containing hydrocarbons and water susceptible to gas hydrate formation into contact with a composition comprising

A) from 5 to 95 weight % of an amphiphile having a hydrophobic tail, R⁵, linked to a hydrophilic head group —N(R¹)(R²) or —[N(R¹)(R²)(R³)]⁺X⁻by a linking moiety, L,

the amphiphile having the general formula (1)

[R⁵-L-N(R¹)(R²)(R³)]⁺X⁻ (1)

wherein each of R¹and R²is independently an alkyl group having from 1 to 5 carbon atoms; or the nitrogen atom and the R¹and R²groups together form a substituted or unsubstituted heterocyclic group;

R³is optionally present; when present, R³is hydrogen or an alkyl group having from 1 to 8 carbon atoms which optionally bears a hydroxy group or a carboxy group at the 2-position;

L comprises an optionally substituted hydrocarbyl group having at least 2 adjacent carbon atoms, at least one heteroatom selected from nitrogen and oxygen, and optionally one or more further heteroatoms;

R⁵is a hydrocarbyl group having from 6 to 22 carbon atoms;

X− is present as an anion when R³is present; and

B) from 5 to 95 weight-% of a cationic surfactant which is selected from the group consisting of quaternary benzyl ammonium salts having, in addition to the benzyl group, at least one C₈-C₁₈-alkyl group bound to the nitrogen atom.