Acylamide and Amine Oxide Derivatives of Linear and Hyperbranched Polyethylenimine. Part 2: Comparison of Gas Kinetic Hydrate Inhibition Performance

Kelland, Malcolm A.; Magnusson, Carlos D.; Lin, Hong; Abrahamsen, Eirin; Mady, Mohamed F.

doi:10.1021/acs.energyfuels.6b01519

Cited by 24 publications

(25 citation statements)

References 29 publications

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“…The amine oxide group (NO, also written as N + –O – ) is highly hydrophilic as a result of its strong polarity, and it also possesses three covalent bonds for connecting with hydrophobic groups. Recently, studies showed that amine oxide compounds can perform well as KHIs, which was demonstrated for linear or hyperbranched alkylated ethylene–amine oxides. − In addition, the amine oxide group has been proven to be rather biocompatible, which meets the criteria of designing environmentally friendly KHIs. , Thus, further investigation of amine oxide-containing polymers as KHIs is of particular interest, which motivated the studies presented here.…”

Section: Introductionmentioning

confidence: 93%

Amine N-Oxide Kinetic Hydrate Inhibitor Polymers for High-Salinity Applications

et al. 2020

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A series of glycidyl amine N-oxide polyethers with cyclic and acyclic amine N-oxide side groups and their block copolymers with poly(propylene) oxide (M n in the range of 1.8−6.4 kg/mol) have been synthesized and investigated as kinetic hydrate inhibitors (KHIs) using a structure II hydrate-forming gas mixture. Polymers based on cyclic amine N-oxides, containing poly(piperidine glycidyl amine N-oxide) units gave a remarkable KHI performance. The best polymers gave similar KHI performance to commercial poly(N-vinylcaprolactam) (PVCap) at the same concentration of 2500 ppm. In addition, upon heating to 95 °C, the best polymers had no cloud point at 2500 ppm (0.25 wt %), even in 15 wt % sodium chloride solution. Thus, these polymers possess excellent potential for injection into high-salinity-and high-temperature-produced fluids.

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Section: Introductionmentioning

confidence: 93%

Amine N-Oxide Kinetic Hydrate Inhibitor Polymers for High-Salinity Applications

et al. 2020

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“…Reports showed that hyperbranched polyethylenimine-alkyl-amine N-oxides (HPEI-R-AOs), especially those with large alkyl groups, can inhibit the formation of both sI and sII hydrates effectively. 17,22 Lately, Zhang et al reported that poly(piperidine glycidyl amine N-oxide) (PIGAO) showed considerable KHI performance on sII hydrate. The best results were on par with the highly established commercial PVCap.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Recently, several series of nonamide polymers, such as poly(isopropenyloxazoline), poly(vinylphosphonate) diesters, poly(alkyl ethylene phosphonate)s, poly(amine N -oxide)s, − poly(vinylsulfonamide)s, poly(vinylaminal)s, poly(sulfobetaine methacrylate)s, and polysaccharides like starch, chitosan, and pectin, have been reported to be excellent KHIs (Figure ). Poly(amine N -oxide) nonamide KHIs have attracted increasing attention, due to the immense structural variability, their superior hydrophilicity, and, most importantly, the remarkable inhibition performance of amine N -oxide polymers.…”

Section: Introductionmentioning

confidence: 99%

“…Poly(amine N -oxide) nonamide KHIs have attracted increasing attention, due to the immense structural variability, their superior hydrophilicity, and, most importantly, the remarkable inhibition performance of amine N -oxide polymers. Reports showed that hyperbranched polyethylenimine-alkyl-amine N -oxides (HPEI-R-AOs), especially those with large alkyl groups, can inhibit the formation of both sI and sII hydrates effectively. , Lately, Zhang et al reported that poly(piperidine glycidyl amine N -oxide) (PIGAO) showed considerable KHI performance on sII hydrate. The best results were on par with the highly established commercial PVCap .…”

Section: Introductionmentioning

confidence: 99%

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N-Oxide Polyethers as Kinetic Hydrate Inhibitors: Side Chain Ring Size Makes the Difference

et al. 2021

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The formation of gas hydrates in flow lines is one of the most severe problems for flow assurance in the gas and oil industry. Developing effective kinetic hydrate inhibitors (KHIs) to avoid the problem of gas hydrate formation has attracted widespread attention. In this study, a series of poly(glycidyl amine N-oxide)s (PGAOs) with 5–7-membered rings as side chains, poly(pyrrolidine glycidyl amine N-oxide)s (PPyrGAOs), poly(piperidine glycidyl amine N-oxide)s (PPiGAOs), and poly(azepane glycidyl amine N-oxide)s (PAzGAOs), with varying molecular weights, have been synthesized. The KHI performance of these glycidyl amine N-oxide polyethers has been evaluated in high-pressure rocking cells with the synthetic natural gas (SNG) mixture. The PGAOs with lower molecular weights gave better KHI performance, and at 2500 ppm, the best one gave an average T o value of 9.8 °C (ΔT = 10.4 °C), which is on a par with polyvinylcaprolactam (PVCap). Even in high concentration of brine solution, none of the PGAOs showed a cloud point up to 95 °C. Employing molecular weights of around 4 kg/mol, the KHI performance of the PGAOs follows the following trend, correlating with the ring size: PPyrGAO < PPiGAO < PAzGAO. However, at higher molecular weight, the ring size of the pendant group did not affect the KHI performance of the PGAOs. PPiGAO with the smaller piperidine ring groups gave better inhibition effect than PAzGAO when the molecular weights were at approximately 8 kg/mol. In addition, the KHI performance of one of the best PAzGAOs was tested in the concentration range from 1000 to 5000 ppm, and an increase of the KHI performance with increasing concentration of polymer was observed. The amine N-oxide functional group is critical for the KHI performance of these polymers, as poly(pyrrolidine glycidyl amine)s (PPyrGAs) and poly(azepane glycidyl amine)s (PAzGAs) with amine groups instead of the N-oxide gave a negligible inhibitory effect.

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“…There are a few examples of direct synthesis of KHIs from polymers such as hyperbranched polyethylenimines that form hyperbranched polyethylenimine-alkyl-amine oxides. , Therefore, we wondered if we could access KHI polymers based on the active monomers directly from more widely available polymeric starting materials. This would avoid using the more expensive acrylamido monomers in Figure and could possibly reduce the cost of (meth)acrylamido-based KHI polymers.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Direct Route to High-Performance Acrylamido-Based Kinetic Gas Hydrate Inhibitors from Poly(acrylic acid)

2020

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(Meth)acrylamido-based polymers are used commercially in kinetic hydrate inhibitor formulations to prevent gas hydrate formation in upstream oil and gas flow lines. The monomers used to make these polymers are relatively expensive. We have now synthesized a series of acrylamido-based polymers directly from low molecular weight poly(acrylic acid) (PAA) in a high-yield process, avoiding the use of expensive monomers. Cloud points of the polymers made from PAA were similar to the homopolymers made from the acrylamido monomers, indicating a good conversion from the acid to the amide group. Slow constant-cooling KHI screening tests were carried out on the new polymers in a series of steel rocking cells using a structure II-forming natural gas mixture. Poly(N-isopropylacrylamide), poly(N-(n-propyl) acrylamide), and polyacryloylpyrrolidine prepared directly from PAA all gave an excellent KHI performance, comparable to the homopolymers made from the acrylamido monomers. This direct synthesis method also allows for a very controlled comparison of the activity of the acrylamido functional groups because every polymer can be derived from the same PAA starting material. Thus, the number of monomer units in each homopolymer is kept constant. Conversion of the poly(methacrylic acid) or poly(methyl methacrylate) by the reaction with amines to give the methacrylamido polymers was not successful, probably due to the steric effect of the backbone methyl groups.

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Acylamide and Amine Oxide Derivatives of Linear and Hyperbranched Polyethylenimine. Part 2: Comparison of Gas Kinetic Hydrate Inhibition Performance

Cited by 24 publications

References 29 publications

Amine N-Oxide Kinetic Hydrate Inhibitor Polymers for High-Salinity Applications

Amine N-Oxide Kinetic Hydrate Inhibitor Polymers for High-Salinity Applications

N-Oxide Polyethers as Kinetic Hydrate Inhibitors: Side Chain Ring Size Makes the Difference

A Simple and Direct Route to High-Performance Acrylamido-Based Kinetic Gas Hydrate Inhibitors from Poly(acrylic acid)

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