Nonpolymeric Citramide-Based Kinetic Hydrate Inhibitors: Good Performance with Just Six Alkylamide Groups

[Image: see text] The use of kinetic hydrate inhibitors (KHIs) is a well-known method for preventing gas hydrate formation in oil and gas production flow lines. The main ingredient in KHI formulations is one or more polymers with amphiphilic groups. Here, we report a series of citramide-based nonpolymeric KHIs. The KHI performance of these citramide derivatives has been studied using a synthetic natural gas mixture (forming structure II hydrate as the thermodynamically preferred phase) in slow constant cooling (ca. 1 °C/h starting from 20.5 °C) high-pressure (76 bar) rocking cell experiments. Isobutyl-substituted alkyl chains in the mono/bis(trialkyl citric acid) amide derivative gave better KHI performance than n-propyl-substituted citramide derivatives. Moreover, biscitramides with six alkylamide functional groups gave better performance than the equivalent monocitramides with three alkylamide groups. A solution of 2500 ppm of bis(tributyl citric acid) amide gave an average gas hydrate onset temperature (T(o)) of 8.4 °C compared to 8.9 °C for a low molecular weight N-vinyl pyrrolidone/N-vinyl caprolactam 1:1 copolymer. For the bis(tributyl citric acid) amide, addition of liquid hydrocarbon (n-decane) lowered further the average T(o) value to 6.2 °C, although this is at least partly due to lowering of the hydrate equilibrium temperature. This study demonstrates that good KHI performance can be obtained from molecules with as little as six amphiphilic alkylamide groups.