WO2008049188A1 - Formulation pour l'élimination de sulfure d'hydrogène de courants d'hydrocarbures et son utilisation - Google Patents

Formulation pour l'élimination de sulfure d'hydrogène de courants d'hydrocarbures et son utilisation Download PDF

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Publication number
WO2008049188A1
WO2008049188A1 PCT/CA2006/001756 CA2006001756W WO2008049188A1 WO 2008049188 A1 WO2008049188 A1 WO 2008049188A1 CA 2006001756 W CA2006001756 W CA 2006001756W WO 2008049188 A1 WO2008049188 A1 WO 2008049188A1
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WO
WIPO (PCT)
Prior art keywords
formulation
hydrogen sulphide
dithiazine
triethylene glycol
amine
Prior art date
Application number
PCT/CA2006/001756
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English (en)
Inventor
Thomas Robert Owens
Original Assignee
Canwell Enviro-Industries Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Canwell Enviro-Industries Ltd. filed Critical Canwell Enviro-Industries Ltd.
Priority to CA2603022A priority Critical patent/CA2603022C/fr
Priority to PCT/CA2006/001756 priority patent/WO2008049188A1/fr
Publication of WO2008049188A1 publication Critical patent/WO2008049188A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1456—Removing acid components
    • B01D53/1468—Removing hydrogen sulfide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1493—Selection of liquid materials for use as absorbents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/06—Polluted air

Definitions

  • the present invention relates to a formulation comprising triethylene glycol for the reduction of hydrogen sulphide levels in hydrocarbon streams. Additionally, the present invention relates to a method for reducing hydrogen sulphide levels in hydrocarbon streams while alleviating solid dithiazine deposit buildup.
  • aldehyde and amine reaction products are based on aldehyde and amine reaction products, particularly triazines.
  • Formulations can consist of low molecular weight aldehydes such as formaldehyde but can also consist of ketones and various adducts thereof.
  • Amines used to produce triazines in prior formulations include alkylamines as disclosed in U.S. Pat. No. 5,674,377, alkanolamines as disclosed in U.S. Pat. No. 4,978,512 and in some cases a combination of amines can be used as disclosed in U.S. Pat. No. 5,347,004 and U.S. Pat. No. 5,554,349.
  • Patent No. 4,978,512 have been shown to be effective at removing hydrogen sulphide from hydrocarbon streams in in-line injection systems, hydrogen sulphide scrubber systems or chemical solvent systems. If glycol is added to the formulation, water can additionally be removed. Depending upon the amount of water present, the glycol content can be as high as 90%
  • the top layer consisted of an aqueous liquid phase containing water and other reaction components and impurities, while the bottom layer which primarily consisted of dithiazine, was in the form of a liquid at operating temperatures between about -5 0 C and 2O 0 C. At temperatures below about -5 0 C, the layer became an amorphous solid.
  • dithiazine solids can contribute to the formation of dithiazine solids in the field including conditions that lower the solubility of dithiazine in the dithiazine/methanol layer, conditions that strip methanol from the dithiazine layer and overspending the scavenger solution.
  • amorphous dithiazine is extremely problematic since substantial deposits can form blockages in chemical storage tanks, bulk truck tanks, gas processing equipment and in produced water disposal wells. Clean up procedures are often time consuming and requires equipment to be taken off-line or shut down. This makes cleaning up solid dithiazine deposits an expensive venture.
  • US Patent Application Serial No. 250436 discloses a process for the reduction or elimination of hydrogen sulphide that does not use triazine, and in fact, teaches away from the use of amines that result in triazines in the reaction products.
  • the hydrogen sulphide scavenging formulation is derived by the reaction of a carbonyl group- containing compound with an alcohol, thiol, amide, thioamide, urea or thiourea.
  • the carbonyl group-containing compound is preferably formaldehyde, and preferably the product is derivable by reaction of formaldehyde with an amine-free alcohol or urea selected from ethylene glycol, propylene glycol, glycerol, diethylene glycol, triethylene glycol, ethyl alcohol, n-butanol, a sugar, a low molecular weight polyvinyl alcohol, castor oil fatty acid and urea. More especially, the scavenger product is used with an amine, especially monoethanolamine.
  • the current invention provides a solution to the problem of dithiazine solid deposit buildup observed with triazine-based scavengers used for the removal of hydrogen sulphide from hydrocarbon streams.
  • triethylene glycol was added initially to the reaction products of monoethanolamine, diglycolamine and formaldehyde. After contacting the hydrocarbon stream, a spent product was produced that consisted substantially of a single phase. Any amorphous dithiazine solids that formed where suspended in the single phase, and the remainder of the dithiazine was in solution.
  • a scavenging formulation comprising triethylene glycol and the reaction products of monoethanolamine and formaldehyde produced a spent product that formed a substantially single phase, with the dithiazine either in solution or suspended in the phase and minimal crystalline dithiazine.
  • chemical formulation comprising triethylene glycol and the reaction products of monoethanolamine and formaldehyde, for the removal of hydrogen sulphide from hydrocarbon streams.
  • a hydrogen sulphide and mercaptan scavenging formulation for reducing dithiazine solids comprises triethylene glycol and the reaction products of reacting a first amine and an aldehyde.
  • the first amine is monoethanolamine and the aldehyde is formaldehyde.
  • the weight of triethylene glycol is about 15% to about
  • the weight of triethylene glycol is about 15% to about 50%.
  • the weight of triethylene glycol is about 15% to about 25%.
  • reaction products comprises 2-[3,5-bis-(2-hydroxy- ethyl)-[1 ,3,5]triazinan-1 -yl]-ethanol.
  • the formulation further comprises a second amine.
  • the second amine is diglycolamine.
  • a scavenging formulation comprising a mixture of triethylene glycol, and at least one triazine.
  • a method for reducing the levels of hydrogen sulphide and mercaptans in hydrocarbon streams comprising contacting said streams with a formulation comprising triethylene glycol and the reaction products of reacting a first amine and an aldehyde, and reacting said reaction products with hydrogen sulphide is provided, thereby reducing the levels of hydrogen sulphide, mercaptans and solid dithiazine deposits.
  • the first amine is monoethanolamine and the aldehyde is formaldehyde.
  • the weight of triethylene glycol is about 15% to about 95% .
  • the weight of triethylene glycol is about 15% to about 50%.
  • the weight of triethylene glycol is about 15% to about 25%.
  • the method further comprises reacting a second amine with the first amine and the aldehyde to produce the reaction product.
  • the second amine is diglycolamine.
  • the hydrocarbon stream is a gaseous or liquid stream.
  • the hydrocarbon stream is a sour natural gas stream.
  • the level of hydrogen sulphide is reduced to a level of about 16 ppm or less.
  • the hydrogen sulphide level is reduced to zero.
  • the step of contacting reacts the formulation with hydrogen sulphide to form a spent formulation comprising a single phase. In another aspect of the method, the step of contacting reacts the formulation with hydrogen sulphide to form a spent formulation comprising dithiazine.
  • the step of contacting reacts the formulation with hydrogen sulphide to form a spent formulation comprising dithiazine wherein the dithiazine may be either a suspended amorphous solid or dissolved in the single phase.
  • the step of contacting reacts the formulation with hydrogen sulphide to form a spent formulation comprising dithiazine, wherein the dithiazine deposits are minimized or eliminated.
  • Figure 1 is a graphical representation of the hydrogen sulphide scavenging performance of a triazine based scavenging formulation of the prior art.
  • Figure 2 is a graphical representation of the hydrogen sulphide scavenging performance of a scavenging formulation of the present invention which contains a 1 :1 molar ratio of total amine to formaldehyde and 24% by weight of triethylene glycol.
  • Figure 3 is a graphical representation of the hydrogen sulphide scavenging performance of a scavenging formulation of the present invention which contains a 1 : 1.5 molar ratio of total amine to formaldehyde and 20% by weight of triethylene glycol.
  • Mercaptans are a group of sulphur containing organic compounds in which the sulphur has replaced an oxygen of a hydroxyl group in the corresponding oxygenated compound.
  • sulphur a group of sulphur containing organic compounds in which the sulphur has replaced an oxygen of a hydroxyl group in the corresponding oxygenated compound.
  • methyl mercaptan in which the oxygen in methanol has been replaced
  • mercaptanol in which one oxygen in ethanol has been replaced
  • cyclohexyl mercaptan in which the oxygen in cyclohexanol is replaced.
  • Sulphides include HS 1 which is variously called hydrogen sulphide ion, hydrosulphide ion, sulfhydryl ion, or bisulphide ion, and H 2 S, hydrogen sulphide
  • Dithiazine solids include amorphous solids and crystalline dithiazine. Detailed Description
  • the formulation of the present invention can be used to scavenge hydrogen sulphide and mercaptans from a variety of hydrocarbon streams, including liquid hydrocarbon streams and sour natural gas.
  • the formulation can be contacted to hydrocarbon streams by various methods including but not limited to simple mixing, inline injection and with a contact scrubber tower.
  • the scavenger formulation of the present invention can be used to reduce the levels of hydrogen sulphide to levels below 16 ppm and as low as 0 ppm.
  • the reaction of hydrogen sulphide with the scavenging formulation of the present invention produces a spent formulation characterized by a single liquid phase that does not contain crystalline dithiazine solids. Any dithiazine that results from the scavenging solution reacting with hydrogen sulphide will be suspended or dissolved in solution and solid dithiazine deposit buildup will be minimized or eliminated. Examples of the embodiment of the invention are outline by Examples 2 to 9.
  • a solution was prepared from 56.2 wt% Formalin (37.5% formaldehyde; 25% methanol), 41.6 wt% monoethanolamine, and 2.2 wt% diglycolamine was formulated.
  • the molar ratio of total amines to formaldehyde was approximately 1 :1.
  • the scavenger solution was subjected to a hydrogen sulphide scavenging capacity test which was performed by passing a feed gas with a known hydrogen sulphide concentration at a known rate through a specified volume or mass of scavenger while the outlet hydrogen sulphide level was measured as a function of time.
  • the test used 57.14 grams of the scavenger formulation maintained at 50°C during the duration of the test and an inlet gas comprised of approximately 18.4% hydrogen sulphide balanced with carbon dioxide. These conditions were used to strip methanol from the spent solution.
  • a scavenger solution was formulated from 41.9 wt% Formalin (37.5% formaldehyde; 25% methanol), 32.4 wt% monoethanolamine (MEA), 1.7 wt% diglycolamine (DGA) and 24 wt% triethylene glycol (about 25 wt% triethylene glycol).
  • the solution was blended by adding the formalin and triethylene glycol to the MEA/DGA mixture.
  • the molar ratio of total amines to formaldehyde was approximately 1 :1.
  • the scavenger solution was subjected to a hydrogen sulphide scavenging capacity test.
  • the heavily overspent solution which resulted from the scavenging capacity test was an opaque yellow single phase liquid at 20 0 C.
  • the solution was thought to be opaque due to an over saturation of dithiazine in the spent solution.
  • the physical stability of the solution was first tested by allowing the solution to sit for an extended period of time (over a week) at approximately 20 0 C to observe whether dithiazine would settle out of the solution and form deposits on the bottom of the sample container. Interestingly, dithiazine did not settle out of the solution and no deposits were formed, in fact, the solution was so stable that it could be centrifuged at 3500 rpm for 30 minutes without observing the formation of a dithiazine layer or deposit.
  • the stability of the solution was also tested at low temperatures, a condition which is known to bring about the formation of dithiazine solids. A portion of the sample was placed in a scintillation vial and cooled in a fridge to a temperature of approximately 2 0 C.
  • a scavenger solution was formulated from 51.4 wt% Formalin (37.5% formaldehyde; 25% methanol), 27.2 wt% monoethanolamine (MEA), 1.4 wt% diglycolamine (DGA) and 20 wt% triethylene glycol.
  • the molar ratio of total amines to formaldehyde was approximately 1 :1.5.
  • the scavenger formulation was subjected to a hydrogen sulphide scavenging test.
  • the test used 57.14 grams of the scavenger formulation and an inlet gas comprised of approximately 18.7% hydrogen sulphide balanced with carbon dioxide.
  • the temperature was maintained at 50 0 C throughout the duration of the test.
  • the results of this capacity test are presented in Figure #3 and shows that breakthrough occurred at 106 minutes.
  • the capacity test was continued beyond breakthrough until the molar concentration of hydrogen sulphide in the outlet gas reached approximately 14.8%.
  • the resulting spent solution can be considered heavily overspent similar to that outlined in Example 2.
  • the spent solution was an opaque, yellow, single layered liquid similar to that observed in
  • Example 2 No solid dithiazine settled out of the solution upon allowing the spent solution to sit for 24 hours at 2O 0 C. Nitrogen gas was then bubbled through the spent solution at a rate of 250 mL/minute for 24 hours in order to simulate a high gas velocity which strips methanol out of spent solution. A small quantity of dithiazine began to settle out of the solution; however, unlike other forms of dithiazine such as that described in Example 1 or that observed in the field, this dithiazine was dispersed back into the spent solution by gentle agitation. The dithiazine in the present spent solution was not sticky or thick and was considered to still be "pump-able" which represents a marked improvement over the reference sample.
  • a scavenger solution was formulated from 51.4 wt% Formalin (37.5% formaldehyde; 25% methanol), 27.2 wt% monoethanolamine (MEA), 1.4 wt% diglycolamine (DGA) and 15% wt% triethylene glycol. It was determined that this concentration of TEG was approximately the minimum concentration needed to maintain the reacted chemical in a uniform solution.
  • the scavenger formulation disclosed in Example 3 was subjected to a scavenging capacity test using an inlet gas containing approximately 18% hydrogen sulphide and 82% carbon dioxide. The test was stopped after the level of hydrogen sulphide in the outlet gas reached approximately 1%. The spent solution produced by this test is more representative of field conditions relative to those outlined in Examples 2 and 3 since using a scavenging solution until well after breakthrough is not typically experienced in the field.
  • the capacity test produced a clear yellow single-phased spent solution.
  • the stability of said solution was first tested by bubbling nitrogen through it at a rate of 250 mL/minute for 72 hours.
  • the spent solution turned slightly turbid over the course of the experiment but no solid dithiazine formed.
  • This solution was then cooled to approximately -25 0 C for an extended period of time and although the solution did not freeze, the viscosity increased slightly and turned milky white.
  • the change in appearance is thought to be due to dithiazine solids beginning to form in the solution; however, no dithiazine settled out of solution and no solid deposits were formed. This process was found to be completely reversible since the milky white characteristic appearance disappeared after the temperature was increased to 20 0 C.
  • Example 6 A scavenger solution was formulated from 51.4 wt% Formalin (37.5% formaldehyde; 25% methanol), 27.2 wt% monoethanolamine (MEA), 1.4 wt% diglycolamine (DGA) and 15% wt% triethylene glycol.
  • the scavenger formulation was field tested and shown to be effective in inhibiting formation of solid deposits.
  • a scavenger solution was formulated from 51.4 wt% Formalin (37.5% formaldehyde; 25% methanol), 27.2 wt% monoethanolamine (MEA), 1.4 wt% diglycolamine (DGA) and 20wt% triethylene glycol.
  • the scavenger formulation was field tested and shown to be effective in inhibiting formation of solid deposits.
  • a formulation comprising of an 80 wt% triazine blend (the reaction products of 95% MEA and 5% DGA) and 20 by wt% triethylene glycol was manufactured and loaded into the contact vessel.
  • the processing system operated for 3 weeks with the triethylene glycol enhanced product with no detection of newly formed dithiazine solids.
  • the processing facility continues to operate with no formation of dithiazine solids; recovered reaction product is a low viscosity, pumpable liquid solution.
  • the triethylene glycol enhanced liquid scavenger formulation this particular facility has attained a record number of operating days with no unscheduled down time.
  • the gas stream contained hydrogen sulphide. Accordingly, the formulation and method is effective in removing hydrogen sulphide from the gas stream and inhibiting the formation of dithiazine solids.
  • a scavenger composition was formulated from 56.6% wt% Formalin (37.5%formaldehyde; 10-15% methanol), 28.4% monoethanolamine (MEA) and 15% triethylene glycol.
  • the scavenger composition was subjected to a scavenging capacity test at 2O 0 C using an inlet gas containing approximately 18.5% hydrogen sulfide and 81.5% carbon dioxide. The test was stopped after the level of hydrogen sulfide in the outlet gas reached approximately 3%.
  • the spent solution consisted of a single phase and more importantly, neither crystalline nor amorphous dithiazine solids formed at 2O 0 C.
  • the spent solution was further tested by cooling the solution to -10 0 C and then -25 0 C for extended periods of time. Although these are conditions that are known to promote the formation of dithiazine solids, neither crystalline nor amorphous dithiazine solids formed at these sub-zero temperatures.
  • spent solutions of the present invention consist of a single liquid phase for the reason that triethylene glycol acts as a co-solvent for water, methanol, dithiazine and the other reaction byproducts.
  • the spent solution retains a single phase even after high temperature conditions since the co-solvent is nonvolatile and is not stripped out of the formulation.
  • the dithiazine remains dissolved in the spent formulation.
  • the solubility of dithiazine in the spent formulation also decreases and amorphous dithiazine solids begin to form; this is observed as an increase in the turbidity of the solution.
  • the percentage of triethylene glycol could be greater than 24%, for example, 30%, or 35%.
  • the limiting factor is the cost of triethylene glycol and at the present time, a percentage above about 24% is considered to be uneconomical.
  • the amount of triethylene glycol will vary depending on the application, field conditions and desired effect, however, as would be known to one skilled in the art, as the triethylene glycol content is increased above a threshold the scavenging capacity of the formulation decreases thus less dithiazine is produced.

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  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Gas Separation By Absorption (AREA)
  • Treating Waste Gases (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé destiné à réduire la teneur en sulfure d'hydrogène de courants d'hydrocarbures. Le procédé comprend la mise en contact d'un gaz ou fluide acide avec une formulation chimique constituée de triéthylène glycol et les produits de réaction d'une amine et d'un aldéhyde. L'utilisation de ce procédé et de ces formulations chimiques permet d'obtenir des produits usés constitués d'une seule phase, ce qui atténue ainsi les problèmes liés au dépôt de dithiazine solide normalement associés aux agents d'épuration à base de triazine.
PCT/CA2006/001756 2006-10-26 2006-10-26 Formulation pour l'élimination de sulfure d'hydrogène de courants d'hydrocarbures et son utilisation WO2008049188A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA2603022A CA2603022C (fr) 2006-10-26 2006-10-26 Formulation d'evacuation du sulfure d'hydrogene des jets d'hydrocarbures et son utilisation
PCT/CA2006/001756 WO2008049188A1 (fr) 2006-10-26 2006-10-26 Formulation pour l'élimination de sulfure d'hydrogène de courants d'hydrocarbures et son utilisation

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PCT/CA2006/001756 WO2008049188A1 (fr) 2006-10-26 2006-10-26 Formulation pour l'élimination de sulfure d'hydrogène de courants d'hydrocarbures et son utilisation

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8022018B2 (en) 2009-12-21 2011-09-20 Baker Hughes Incorporated Quaternized dithiazines and method of using same in treatment of wells
US8022017B2 (en) 2009-12-21 2011-09-20 Baker Hughes Incorporated Method of using dithiazine to inhibit corrosion
US8354361B2 (en) 2009-12-21 2013-01-15 Baker Hughes Incorporated Method of using dithiazines and derivatives thereof in the treatment of wells
RU2482163C1 (ru) * 2012-03-12 2013-05-20 Ахматфаиль Магсумович Фахриев Нейтрализатор сероводорода и способ его использования
US8512449B1 (en) 2010-12-03 2013-08-20 Jacam Chemical Company 2013, Llc Oil-soluble triazine sulfide scavenger
US8920568B2 (en) 2011-03-28 2014-12-30 Baker Hughes Incorporated Method for the dissolution of amorphous dithiazine
US9296940B2 (en) 2009-12-21 2016-03-29 Baker Hughes Incorporated Dithiazine derivatives
WO2022066969A1 (fr) * 2020-09-25 2022-03-31 Ascend Performance Materials Operations Llc Solvants nitriles
WO2022076460A1 (fr) * 2020-10-08 2022-04-14 Conocophillips Company Procédé de dissolution de dithiazines amorphes
US11572514B2 (en) 2020-10-08 2023-02-07 Conocophillips Company Elemental sulfur dissolution and solvation

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US11584879B1 (en) 2021-12-21 2023-02-21 Halliburton Energy Services, Inc. Increasing scavenging efficiency of H2S scavenger by adding linear polymer
US11814576B2 (en) 2021-12-21 2023-11-14 Halliburton Energy Services, Inc. Increasing scavenging efficiency of H2S scavenger by adding linear polymer

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US5688479A (en) * 1994-12-22 1997-11-18 Uop Process for removing HCl from hydrocarbon streams
US5980845A (en) * 1994-08-24 1999-11-09 Cherry; Doyle Regeneration of hydrogen sulfide scavengers
WO2002051968A1 (fr) * 2000-12-27 2002-07-04 M-I L.L.C. Procede de reduction ou d'elimination de sulfure d'hydrogene
US6582624B2 (en) * 2001-02-01 2003-06-24 Canwell Enviro-Industries, Ltd. Method and composition for removing sulfides from hydrocarbon streams

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US4978512A (en) * 1988-12-23 1990-12-18 Quaker Chemical Corporation Composition and method for sweetening hydrocarbons
US4978512B1 (en) * 1988-12-23 1993-06-15 Composition and method for sweetening hydrocarbons
US5980845A (en) * 1994-08-24 1999-11-09 Cherry; Doyle Regeneration of hydrogen sulfide scavengers
US5688479A (en) * 1994-12-22 1997-11-18 Uop Process for removing HCl from hydrocarbon streams
WO2002051968A1 (fr) * 2000-12-27 2002-07-04 M-I L.L.C. Procede de reduction ou d'elimination de sulfure d'hydrogene
US6582624B2 (en) * 2001-02-01 2003-06-24 Canwell Enviro-Industries, Ltd. Method and composition for removing sulfides from hydrocarbon streams
US20030234383A1 (en) * 2001-02-01 2003-12-25 Canwell Enviro-Industries, Ltd. Method and composition for removing sulfides from hydrocarbon streams

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8022018B2 (en) 2009-12-21 2011-09-20 Baker Hughes Incorporated Quaternized dithiazines and method of using same in treatment of wells
US8022017B2 (en) 2009-12-21 2011-09-20 Baker Hughes Incorporated Method of using dithiazine to inhibit corrosion
US8354361B2 (en) 2009-12-21 2013-01-15 Baker Hughes Incorporated Method of using dithiazines and derivatives thereof in the treatment of wells
US9296940B2 (en) 2009-12-21 2016-03-29 Baker Hughes Incorporated Dithiazine derivatives
US8512449B1 (en) 2010-12-03 2013-08-20 Jacam Chemical Company 2013, Llc Oil-soluble triazine sulfide scavenger
US8920568B2 (en) 2011-03-28 2014-12-30 Baker Hughes Incorporated Method for the dissolution of amorphous dithiazine
RU2482163C1 (ru) * 2012-03-12 2013-05-20 Ахматфаиль Магсумович Фахриев Нейтрализатор сероводорода и способ его использования
WO2022066969A1 (fr) * 2020-09-25 2022-03-31 Ascend Performance Materials Operations Llc Solvants nitriles
US12006493B2 (en) 2020-09-25 2024-06-11 Ascend Performance Materials Operations Llc Nitrile solvents
WO2022076460A1 (fr) * 2020-10-08 2022-04-14 Conocophillips Company Procédé de dissolution de dithiazines amorphes
US11572514B2 (en) 2020-10-08 2023-02-07 Conocophillips Company Elemental sulfur dissolution and solvation
US11814588B2 (en) 2020-10-08 2023-11-14 Conocophillips Company Elemental sulfur dissolution and solvation

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CA2603022A1 (fr) 2008-02-13

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