Triazine-based H<sub>2</sub>S Scavenging: Development of a Conceptual Model for the Understanding of Fouling Formation

Madsen, Henrik; Jensen, Carina; Søgaard, Erik Gydesen

doi:10.1080/10916466.2014.915852

Cited by 11 publications

(8 citation statements)

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“…Triazines of the type 1,3,5‐tris(2‐hydro‐xyethyl)‐symtriazine are mostly soluble in aqueous media whether the medium is acidic, basic, or neutral. They are based upon other triazine forms that are miscible with hydrocarbons and soluble in aqueous solutions, a good example being 2,2',2”‐(hexahydro‐1,3,5‐triazine‐1,3,5 triyl)triethanol , .…”

Section: Hydrogen Sulfide Scavengersmentioning

confidence: 99%

“…The nitrogen atoms in triazines are tertiary, i.e., they can only play the role of hydrogen bond acceptors, not donors. It is this structure that increases the affinity of triazines towards H 2 S. The water solubility of hexahydro‐s‐triazine is boosted due to the presence of the hydroxyl groups because they create active hydrogen bonds to the water molecules , , , . The most commonly used triazines can be found in Tab.…”

Section: Hydrogen Sulfide Scavengersmentioning

confidence: 99%

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A Comprehensive Review of H₂S Scavenger Technologies from Oil and Gas Streams

2017

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Sour crudes containing > 0.5 % sulfur are of low quality and cause harm to equipment, the environment, and to humans. Therefore, sustainable measures for crude oil sweetening are of significant importance. Removal of H2S directly at the wellhead before the transport increases the value of crude oil and may be necessary to adhere to legal transport laws. Chemical agents known as scavengers are used to scrub H2S from crude oils. Scavengers are either of the regenerative or non‐regenerative type and are used depending on the pH or water content of the crude stream. The literature has been surveyed to reveal those absorbents that allow the most effective scavenging of H2S at wellhead applications. The chemical processing, including recovery of scavenger or end use of products, is discussed for decision‐making at the confluence of chemistry and chemical engineering for H2S removal. This work investigates how and why some scavengers perform better for some crudes and environmental conditions than others with the intent to develop designer scavengers and processing conditions for the crude oil industry.

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Section: Hydrogen Sulfide Scavengersmentioning

confidence: 99%

Section: Hydrogen Sulfide Scavengersmentioning

confidence: 99%

A Comprehensive Review of H₂S Scavenger Technologies from Oil and Gas Streams

2017

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“…H 2 S. 94 The main problem with using triazines as scavengers is fouling, the formation of a solid byproduct that may interfere with later processes or cause blockages. The fouling product from triazine reacting with H 2 S is a dithiazine polymer, one example of which is shown in structure (10).…”

Section: Scheme 4 Proposed Reaction Scheme Of 135-(2-hydroxypropylmentioning

confidence: 99%

Problems Associated with Sour Gas in the Oilfield Industry and Their Solutions

2015

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. (2015) 'The problems associated with sour gas in the oil eld industry and their solutions.', Energy fuels., 29 (8). pp. 4667-4682. Further information on publisher's website:http://dx.doi.org/10.1021/acs.energyfuels.5b00952Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in Energy Fuels, copyright c 2015 American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see http://dx.doi.org/10.1021/acs.energyfuels.5b00952.Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractFossil fuels are still a necessary and important part of modern living, keeping cars running and houses heated for example. As demands have risen and reservoirs of oil and natural gas have depleted, it has become increasingly more important to tap in to fields that were once classified as undesirable. Sour fields, fields high in acidic gases such as hydrogen sulfide and carbon dioxide, are one such option. There are many difficulties and dangers associated with working sour fields, such as toxicity of the sour gases, hydrate formation and corrosion of equipment that have prevented these resources being used in the past. Many varied methods of overcoming these problems have been developed, from removing the sour components to inhibiting their effects. This review highlights the major issues raised by sour fields as well as a wide range of solutions in use today.

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“…This greatly facilities application of MS analysis to reaction monitoring and mechanism determination. − In the case of the reaction between triazine and H 2 S, some attempts have been made to elucidate the reaction mechanism using mass spectrometry. Madsen et al , investigated the reaction products and their fragmentation products from triazine and H 2 S using electrospray ionization mass spectrometry (ESI-MS), and possible pathways and structures were suggested to describe the observed products. They also studied the precipitate by use of triazines for H 2 S scavenging, and found the generated polymer, resulting from the decomposition of dithiazine to methanedithiol, followed by reaction between dithiazine and other methanedithiol molecules, had an empirical formula of (C 7 H 15 S 4.5 NO) n after identification by ESI-MS in tandem with infrared spectroscopy and X-ray diffraction .…”

mentioning

confidence: 99%

“…They also studied the precipitate by use of triazines for H 2 S scavenging, and found the generated polymer, resulting from the decomposition of dithiazine to methanedithiol, followed by reaction between dithiazine and other methanedithiol molecules, had an empirical formula of (C 7 H 15 S 4.5 NO) n after identification by ESI-MS in tandem with infrared spectroscopy and X-ray diffraction . Those investigations are of significance to better understand the reaction pathway and additional products, , as well as the fouling formation involved in H 2 S scavenging with triazine.…”

mentioning

confidence: 99%

Elucidating the Reaction Mechanisms between Triazine and Hydrogen Sulfide with pH Variation Using Mass Spectrometry

et al. 2018

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Triazine is one of the most economical and effective scavengers for hydrogen sulfide (HS) removal, but the reaction mechanisms between triazine and HS with pH variation in solution are still poorly understood. Herein, we show that the reaction process can be directly probed by means of paper spray mass spectrometry, in which an aprotic solvent (e.g., acetonitrile) is more favorable to the observation of reaction intermediates than a protic solvent (e.g., methanol), because of hydrogen bond interaction. Varying the pH of the reaction leads to completely different reaction pathways. With the pH in the range of 5.58 to 7.73, the major product was thiadiazine. With a pH of 3.02-3.69, thiadiazine is converted to 2-(5-(2-hydroxyethyl)-1,3,5-thiadiazinan-3-yl)acetaldehyde, which differs from the traditional pathway of analogous reactions. However, as ammonia was added into the reaction and the pH was adjusted to the range 8.45-9.43, triazine readily undergoes hydrolysis, and the formed intermediate reacts with ammonia and formaldehyde generated in situ from triazine to produce 1-(2-hydroxyethyl)-3,5,7-triaza-1-azoniatricyclo [3.3.1.1]decane (HTAD). Further increasing the pH up to 10.27-11.21 leads to the decomposition of HTAD. Based on the experimental observation and evidence from high-resolution and tandem mass spectrometry, we propose the plausible reaction mechanisms between triazine and HS, as well as the derived reaction from triazine under different pH conditions.

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Triazine-based H₂S Scavenging: Development of a Conceptual Model for the Understanding of Fouling Formation

Cited by 11 publications

References 5 publications

A Comprehensive Review of H₂S Scavenger Technologies from Oil and Gas Streams

A Comprehensive Review of H₂S Scavenger Technologies from Oil and Gas Streams

Problems Associated with Sour Gas in the Oilfield Industry and Their Solutions

Elucidating the Reaction Mechanisms between Triazine and Hydrogen Sulfide with pH Variation Using Mass Spectrometry

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Triazine-based H2S Scavenging: Development of a Conceptual Model for the Understanding of Fouling Formation

Cited by 11 publications

References 5 publications

A Comprehensive Review of H2S Scavenger Technologies from Oil and Gas Streams

A Comprehensive Review of H2S Scavenger Technologies from Oil and Gas Streams

Problems Associated with Sour Gas in the Oilfield Industry and Their Solutions

Elucidating the Reaction Mechanisms between Triazine and Hydrogen Sulfide with pH Variation Using Mass Spectrometry

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Product

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Triazine-based H₂S Scavenging: Development of a Conceptual Model for the Understanding of Fouling Formation

A Comprehensive Review of H₂S Scavenger Technologies from Oil and Gas Streams

A Comprehensive Review of H₂S Scavenger Technologies from Oil and Gas Streams