Abstract
Poly(N-vinylamide) derivatives were synthesized to improve the performance of kinetic hydrate inhibitors (KHIs). In this work, we synthesized poly(N-vinylformamide) (PNVF) and poly(N-vinylcaprolactam) (PVCap) by free radical polymerization with several commercial chain transfer agents (CTAs), which afforded a few thousand Mn. The structures of synthesized PNVF and PVCap were then investigated by 1H NMR and MALDI-TOF/MS spectrograms. KHI properties of the synthesized PNVF and PVCap polymers were also evaluated by the high-pressure slow constant cooling KHI test method. Some of the tested polymers showed a better KHI effect than PVCap.
Similar content being viewed by others
References
Sloan ED, Koh CA (2008) Clathrate hydrates of natural gases, vol 119, 3rd edn. CRC Press, Boca Raton, FL
Hammerschmidt EG (1934) Formation of gas hydrates in natural gas transmission lines. Ind Eng Chem 26(8):851–855
Kelland MA (2006) History of the development of low dosage hydrate inhibitors. Energy Fuels 20:825
Kelland MA (2014) Production chemicals for the oil and gas industry, 2nd edn. CRC Press, Boca Raton, FL (For a good KHI review you could use this)
Kelland MA (2011) A review of kinetic hydrate inhibitors: tailormade water-soluble polymers for oil and gas industry applications. In: Wytherst MC (ed) Advances in materials science research, vol 8. Nova Science Publishers Inc, New York
Lederhos JP, Long JP, Sum A, Christiansen RL, Sloan ED (1996) Effective kinetic inhibitors for natural gas hydrates. Chem Eng Sci 51(8):1221
Sa JH, Kwak GH, Lee BR, Park DH, Han K, Lee KH (2013) Hydrophobic amino acids as a new class of kinetic inhibitors for gas hydrate formation. Sci Rep 3:7
Naeiji P, Arjomandi A, Varaminian F (2014) Amino acids as kinetic inhibitors for tetrahydrofuran hydrate formation: experimental study and kinetic modeling. J Nat Gas Sci Eng 21:64–70
Rad SA, Khodaverdiloo KR, Karamoddin M, Varaminian F, Peyvandi K (2015) Kinetic study of amino acids inhibition potential of glycine and l-leucine on the ethane hydrate formation. J Nat Gas Sci Eng 26:819–826
Sa JH, Kwak GH, Han K, Ahn D, Cho SJ, Lee JD, Lee KH (2016) Sci Rep 6:9
Sa J-H, Kwak G-H, Han K, Ahn D, Lee K-H (2015) Sci Rep 5:11526
Xu Y, Yang M, Yang X (2010) Chitosan as green kinetic inhibitors for gas hydrate formation. J Nat Gas Chem 19:431–435
Talaghat MR (2012) Experimental investigation of double gas hydrate formation in the presence of modified starch as a kinetic inhibitor in a flow mini‐loop apparatus. Can J Chem Eng 90:429–436
Colle KS, Costello CA, Talley LD, Longo JM, Oelfke RH, Berluche E (1996) WO patent application 96/08672
Daraboina N, Malmos C, von Solms N (2013) Synergistic kinetic inhibition of natural gas hydrate formation. Fuel 108:749–757
Zhao X, Qiu Z, Zhou G, Huang W (2015) Synergism of thermodynamic hydrate inhibitors on the performance of poly (vinyl pyrrolidone) in deepwater drilling fluid. J Nat Gas Sci Eng 23:47–54
Kang SP, Kim ES, Shin JY, Kim HT, Kang JW, Cha JH, Kim KS (2013) Unusual synergy effect on methane hydrate inhibition when ionic liquid meets polymer. RSC Adv 3:19920–19923
Kelland MA, Dirdal EG, Ree LHS (2020) High cloud point polyvinylaminals as non-amide-based kinetic gas hydrate inhibitors. Energy Fuels 34:8301–8307
Ajiro H, Takemoto Y, Akashi M, Chua PC, Kelland MA (2010) Study of the kinetic hydrate inhibitor performance of a series of Poly (N-alkyl-N-vinylacetamide) s. Energy Fuels 24:6400–6410
Kelland MA, Abrahamsen E, Ajiro H, Akashi M (2015) Kinetic hydrate inhibition with N-alkyl-N-vinylformamide polymers: comparison of polymers to n-propyl and isopropyl groups. Energy Fuels 29:4941–4946
Zhang Q, Kawatani R, Ajiro H, Kelland MA (2018) Optimizing the kinetic hydrate inhibition performance of N-alkyl-N-vinylamide copolymers. Energy Fuels 32:4925–4931
Kawatani R, Kawata Y, Yusa SI, Kelland MA, Ajiro H (2018) Synthesis of thermosensitive poly (N-vinylamide) derivatives bearing oligo ethylene glycol chain for kinetic hydrate inhibitor. Macromolecules 51:7845–7852
Seo SD, Paik H, Lim D, Lee JD (2017) Effects of poly (n-vinylcaprolactam) molecular weight and molecular weight distribution on methane hydrate formation. Energy Fuels 31:6358–6363
Zhang Q, Kelland MA (2018) Study of the kinetic hydrate inhibitor performance of poly (N-vinylcaprolactam) and poly (N-isopropylmethacrylamide) with varying end caps. Energy Fuels 32:9211–9219
Perdigão LMA, Staniec PA, Champness NR, Beton PH (2009) Langmuir 25:2278–228
Qin H-B, Sun C-Y, Sun Z-F, Liu B, Chen G-J (2016) Relationship between the interfacial tension and inhibition performance of hydrate inhibitors. Chem Eng Sci 148:182–189
Acknowledgments
This study is supported by Research Foundation for the Electrotechnology of Chubu (R-01206). This study is also supported by JSPS KAKENHI (JP20H05223). We appreciate Ms. Yoshiko Nishikawa for the measurements and analyses of MALDI-TOF/MS.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Choi, J., Kelland, M.A., Furumai, H. et al. Preparation of poly(N-vinyl caprolactam) with various end groups using chain transfer agents and evaluation of their effects on kinetic hydrate inhibition. Polym. Bull. 79, 3513–3522 (2022). https://doi.org/10.1007/s00289-021-03644-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-021-03644-7