US 11,753,576 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. 16/424,161.
Prior Publication US 2020/0377783 A1, Dec. 3, 2020
This patent is subject to a terminal disclaimer.
Int. Cl. C09K 8/52 (2006.01); C07C 233/09 (2006.01)
CPC C09K 8/52 (2013.01) [C07C 233/09 (2013.01); C09K 2208/22 (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, methyl, ethyl, ethenyl, or 2-propenyl 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 the formula (I) is produced by the condensation reaction of at least one fatty acid with at least one N,N-dialkylamino alkyl amine and subsequent neutralization with at least one carboxylic acid, and
wherein the at least one carboxylic acid used for neutralization is selected from the group consisting of formic acid, acetic acid, propionic acid, acrylic acid, methacrylic acid and mixtures thereof, and
wherein the at least one anti-agglomerant is essentially free of glycerol.