US 11,753,577 B2
Method for inhibiting gas hydrate blockage in oil and gas pipelines
Scot Bodnar, Houston, TX (US); Dan Smith, Spring, TX (US); Felix Hoevelmann, Mühldorf (DE); Corinna Krüger, Kirchheim (DE); Matthias Krull, Harxheim (DE); Jonathan James Wylde, The Woodlands, TX (US); and Lisa Greaney Tejada, Spring, TX (US)
Assigned to Clariant International Ltd., Muttenz (CH)
Filed by Clariant International, Ltd., Muttenz (CH)
Filed on May 28, 2019, as Appl. No. 16/424,241.
Prior Publication US 2020/0377784 A1, Dec. 3, 2020
Int. Cl. C09K 8/52 (2006.01); C07C 231/02 (2006.01); C10L 1/224 (2006.01); C07C 233/09 (2006.01)
CPC C09K 8/52 (2013.01) [C07C 231/02 (2013.01); C07C 233/09 (2013.01); C09K 2208/22 (2013.01); C10L 1/224 (2013.01); C10L 2230/08 (2013.01)] 15 Claims
 
1. A method for inhibiting the agglomeration of gas hydrates, comprising the step of injecting at least one anti-agglomerant comprising at least one N,N-dialkyl-ammoniumalkyl fatty acid amide represented by the formula (I)

OG Complex Work Unit Chemistry
wherein
R1 is an alkyl or alkenyl group having from 7 to 21 carbon atoms,
R2 and R3 are each independently an alkyl group containing 1 to 10 carbon atoms, or together form an optionally substituted ring having 5 to 10 ring atoms, wherein the ring may carry up to 3 substituents,
R4 is hydrogen or an alkyl group having 1 to 6 carbon atoms,
R5 is hydrogen or an optionally substituted hydrocarbyl group having 1 to 22 carbon atoms and
A is an alkylene group having two or three carbon atoms,
into a fluid comprising gas, water and oil under conditions prone to the formation of gas hydrates,
wherein the at least one N,N-dialkyl-ammoniumalkyl fatty acid amide represented by formula (I) is produced by the aminolysis of a fatty acid ester of at least one fatty acid and at least one monohydric C1 to C4-alcohol with at least one N,N-dialkylamino alkyl amine and subsequent neutralization with at least one carboxylic acid,
wherein the fatty acid ester of the at least one fatty acid with the at least one monohydric C1-C4-alcohol has the formula (III)
R1—COOR6  (III)
wherein
R1 is defined above, and
R6 is an alkyl group having 1 to 4 carbon atoms,
and wherein the at least one N,N-dialkylamino alkyl amine has the general formula (V)

OG Complex Work Unit Chemistry
wherein
R2, R3, R4 and A are each independently defined above.