US20120012507A1 - Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons - Google Patents

Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons Download PDF

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Publication number
US20120012507A1
US20120012507A1 US12/836,037 US83603710A US2012012507A1 US 20120012507 A1 US20120012507 A1 US 20120012507A1 US 83603710 A US83603710 A US 83603710A US 2012012507 A1 US2012012507 A1 US 2012012507A1
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United States
Prior art keywords
hydrogen sulfide
scavenger
alpha
bis
fluid
Prior art date
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Abandoned
Application number
US12/836,037
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English (en)
Inventor
Dennis R. Compton
J. Byron Strickland
Juan M. Garcia, III
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ChampionX LLC
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Nalco Co LLC
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 Nalco Co LLC filed Critical Nalco Co LLC
Priority to US12/836,037 priority Critical patent/US20120012507A1/en
Assigned to NALCO COMPANY reassignment NALCO COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: COMPTON, DENNIS R., GARCIA, JUAN M., STRICKLAND, J BYRON
Priority to EP20110807425 priority patent/EP2593535A4/en
Priority to RU2013102414/04A priority patent/RU2563633C2/ru
Priority to JP2013519783A priority patent/JP5890409B2/ja
Priority to ARP110102515A priority patent/AR082165A1/es
Priority to CN201180034667.8A priority patent/CN103403129B/zh
Priority to BR112013000890A priority patent/BR112013000890A2/pt
Priority to CA2805404A priority patent/CA2805404C/en
Priority to MX2013000507A priority patent/MX2013000507A/es
Priority to PCT/US2011/043793 priority patent/WO2012009396A2/en
Priority to SG2013002993A priority patent/SG187078A1/en
Priority to KR1020137003671A priority patent/KR20130047739A/ko
Publication of US20120012507A1 publication Critical patent/US20120012507A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
    • 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
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/207—Acid gases, e.g. H2S, COS, SO2, HCN

Definitions

  • This invention relates generally to the treatment of sour gas and liquid hydrocarbon to remove or reduce the levels of hydrogen sulfide therein.
  • the toxicity of hydrogen sulfide in hydrocarbon fluids is well known in the industry. This has caused considerable expense and efforts to be expended annually to reduce its content to a safe level.
  • a regenerative system for treating sour gas streams.
  • These systems typically employ a compound used in an absorption tower to contact the produced fluids and selectively absorb the hydrogen sulfide and possibly other toxic materials such as carbon dioxide and mercaptans. The absorption compound is then regenerated and reused in the system.
  • Typical hydrogen sulfide absorption materials include alkanolamines, PEG, hindered amines, and other species that can be regenerated.
  • Nonregenerative scavengers for small plant hydrogen sulfide removal fall into four general categories: 1) aldehyde based, 2) metallic oxide based, 3) caustic based, and 4) other processes.
  • the scavenger reacts with the hydrogen sulfide to form a nonlethal compound or a compound, which can be removed from the hydrocarbon.
  • formthionals e.g., trithiane
  • Prior Art aldehyde scavengers typically include low molecular weight aldehydes and ketones and adducts thereof.
  • the low molecular weight aldehydes may also be combined with an alkyl or alkanolamine as disclosed in U.S. Pat. No. 4,748,011.
  • Other aldehyde derived scavengers include the reaction product of low molecular weight alkanolamines and aldehydes as disclosed in U.S. Pat. No. 4,978,512.
  • PCT Application WO 92/01481 discloses a method of reducing sulfides in different applications using certain tri-substituted-hexahydro-s-triazines.
  • German reference DE4027300 discloses a regenerative solvent for removing H 2 S and mercaptans.
  • U.S. Pat. No. 5,347,004 discloses the use of 1,3,5 alkoxyalkylene hexahydro triazines.
  • PCT Application WO 91 US 5232 discloses hydroxyalkyl triazine scavengers, specifically an N,N′,N′′-tris(2-hydroxyethyl)hexahydro-s-triazine.
  • 5,774,024 discloses the combination of an alkyl triazine scavenger and quaternary ammonium salt, where the quaternary ammonium salt enhances the effectiveness of the alkyl-triazine.
  • At least one embodiment of the invention is directed towards a method for removing hydrogen sulfide from a hydrocarbon fluid.
  • the method comprises contacting the fluid with an effective amount of a composition comprising a hydrogen sulfide scavenger.
  • the amount of hydrogen sulfide scavenger is sufficient to react with the hydrogen sulfide to reduce the amount hydrogen sulfide released into the vapor space.
  • the reaction product of the hydrogen sulfide scavenger and the hydrogen sulfide remain soluble in the hydrocarbon fluid.
  • the hydrogen sulfide scavenger contains at least one alpha-amino ether.
  • composition may include one item selected from the list consisting of:
  • the reaction product of the sulfide scavenging formulation and the hydrogen sulfide may not form a separate fluid layer.
  • the method may also further comprise the step of reacting a secondary amine with a formaldehyde equivalent to form at least some of the scavenging formulation.
  • the hydrocarbon fluid may be a liquid.
  • Alpha-amino ether means a molecule according to the formula:
  • R 1 , R 2 , R 3 , R 4 are carbon containing side chains containing 1-20 carbon atoms and includes cyclic and acyclic compounds.
  • the cyclic compounds can be aromatic or non-aromatic. Examples include but are not limited to, methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl, morpholino, and phenyl, and they all can be the same group or one or more different groups.
  • B is an ether group, which is either an oxygen atom or a group having an oxygen atom at both ends (such as —OCH 2 O— or —OC 2 H 4 O—).
  • Formaldehyde equivalent means a composition of matter containing at least one group according to the formula: (CH 2 O) n in which n is an integer greater than or equal to 1, and/or a composition of matter including formaldehyde or related molecules such as paraformaldehyde, and/or s-trioxane.
  • Hydrocarbon fluid means a liquid or gas predominantly comprising organic material including but not limited to kerosene, crude oil, crude oil emulsions, oilfield condensate, petroleum residua, refined fuels, distillate fuels, fuel oil, heating oils, diesel fuel, gasoline, jet fuel, bunker fuel oils, and any combination thereof.
  • Non-Regenerative Scavenger means a scavenger, which is consumed by the process of scavenging.
  • Regenerative Scavenger means a scavenger, which is not consumed by the process of scavenging.
  • “Scavenger” means a composition of matter, such as but not limited to alpha-amino ethers, useful in reducing the amount of or mitigating the effects of some other composition of matter, such as but not limited to hydrogen sulfide, in a fluid medium.
  • the hydrogen sulfide in a hydrocarbon fluid is reduced by the introduction of an alpha-amino ether scavenger into the fluid.
  • the alpha-amino ether is a portion of a scavenging formulation is used in a hydrocarbon fluid.
  • the formulation comprises alpha-amino ether and can consist of a carrier liquid as well.
  • the formulation can be introduced into the hydrocarbon fluid by mechanical means including but not limited to injection pumps or any mechanism disclosed in U.S. Pat. Nos. 5,744,024 and 5,840,177.
  • the gas may be passed through an absorption tower containing a scavenging formulation.
  • alpha-amino ether scavenger is soluble in hydrocarbon fluids, since it is not a water-based product.
  • the hydrogen sulfide scavenger is produced by reacting a secondary amine with formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
  • formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
  • the reaction product also comprises 10-25% of the non-ether diamine (compound A).
  • Compound A is an unavoidable side product of the reaction mixture.
  • the reaction can be performed by mixing the reactants in solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
  • solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
  • the ratio of amine to formaldehyde in the reaction mixture is inclusively within the range of 1.5:1 to 1:1.5 and is preferably between 1.2:1 and 1:1.2.
  • any of the R and R′ groups correspond to any of the R 1 , R 2 , R 3 , and R 4 , groups described in the definition of “alpha-amino ether”.
  • Table 1 compares the inventive composition in naphtha at 22 degrees C., Table 2 kerosene at 22 degrees C., and Table 3 slurry oil (such as carbon black oil, decant oil, and clarified slurry oil produced in a refinery) at 97 degrees C.
  • the samples contained variable levels of hydrogen sulfide and were comparatively treated with various dosages of alpha-amino ether scavenger or left untreated, and the amounts H 2 S reduced in each sample was recorded.
  • Table 1 Naphtha 22° C. H2S levles ppm H2S Percent Dose Treatment (ppm) Reduced Reduction Ratio Time Untreated 800 Compounds A-C 20 780 97.5 0.2 2 h Compounds A-C 6 794 99.2 0.3 2 h Compounds A-C 3 797 99.6 0.2 24 h Compounds A-C ⁇ 1 >799 99.9 0.3 24 h Compounds A-C 12 788 98.5 0.2 2 h (4) (796) (99.5) (24 h) Table 2: Kerosine 22° C.
  • H2S levles ppm H2S Percent Dose Treatment (ppm) Reduced Reduction Ratio Time Untreated 1400 Compounds A-C 400 1000 71 0.1 2 h Compounds A-C 220 1180 84 0.2 2 h Compounds A-C 95 1305 93 0.3 2 h Table 3: Slurry oil 97° C.
  • the amount of H 2 S present in the vapor space was determined by measuring the vapor space hydrogen sulfide levels according to ASTM D5705-03. The test procedure was modified by running at temperatures other than 60° C. A one-gallon sample was divided into multiple 500 milliliter samples for testing. The treated containers were pre-dosed with Compounds A-C and then the fluid being tested was poured into the container.
  • the dose ratio was the number used to determine the ppm treat rate for the sample.
  • the untreated sample resulted in a vapor space hydrogen sulfide measurement of 800 ppm.
  • a dose ratio of 0.2 indicates the sample was treated with 160 ppm of additive.
  • a dose ratio of 0.3 indicates that the sample was treated with 240 ppm of additive.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Gas Separation By Absorption (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US12/836,037 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons Abandoned US20120012507A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
US12/836,037 US20120012507A1 (en) 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons
KR1020137003671A KR20130047739A (ko) 2010-07-14 2011-07-13 탄화수소로부터 황화수소를 제거하기 위한 알파-아미노 에테르의 용도
BR112013000890A BR112013000890A2 (pt) 2010-07-14 2011-07-13 método para reduzir a quantidade de sulfeto de hidrogênio em um fluido de hidrocarboneto
RU2013102414/04A RU2563633C2 (ru) 2010-07-14 2011-07-13 Использование простых альфа-аминоэфиров для удаления сероводорода из углеводородов
JP2013519783A JP5890409B2 (ja) 2010-07-14 2011-07-13 炭化水素から硫化水素を除去するためのアルファ−アミノエーテルの使用
ARP110102515A AR082165A1 (es) 2010-07-14 2011-07-13 USO DE a-AMINO ETERES PARA ELIMINAR SULFURO DE HIDROGENO DE HIDROCARBUROS
CN201180034667.8A CN103403129B (zh) 2010-07-14 2011-07-13 α-氨基醚用于从烃中除去硫化氢的用途
EP20110807425 EP2593535A4 (en) 2010-07-14 2011-07-13 USE OF ALPHA AMINO ETHERS FOR THE REMOVAL OF HYDROGEN SULPHIDE FROM HYDROCARBONS
CA2805404A CA2805404C (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons
MX2013000507A MX2013000507A (es) 2010-07-14 2011-07-13 Uso de alfa-amino eteres para eliminacion de sulfuro de hidrogeno a partir de hidrocarburos.
PCT/US2011/043793 WO2012009396A2 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons
SG2013002993A SG187078A1 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons

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US12/836,037 US20120012507A1 (en) 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons

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US (1) US20120012507A1 (enrdf_load_stackoverflow)
EP (1) EP2593535A4 (enrdf_load_stackoverflow)
JP (1) JP5890409B2 (enrdf_load_stackoverflow)
KR (1) KR20130047739A (enrdf_load_stackoverflow)
CN (1) CN103403129B (enrdf_load_stackoverflow)
AR (1) AR082165A1 (enrdf_load_stackoverflow)
BR (1) BR112013000890A2 (enrdf_load_stackoverflow)
CA (1) CA2805404C (enrdf_load_stackoverflow)
MX (1) MX2013000507A (enrdf_load_stackoverflow)
RU (1) RU2563633C2 (enrdf_load_stackoverflow)
SG (1) SG187078A1 (enrdf_load_stackoverflow)
WO (1) WO2012009396A2 (enrdf_load_stackoverflow)

Cited By (18)

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US20130131387A1 (en) * 2011-11-23 2013-05-23 General Electric Company Methods and compounds for improving sulfide scavenging activity
WO2013181056A1 (en) 2012-05-29 2013-12-05 Baker Hughes Incorporated Synergistic h2s scavengers
US20140166282A1 (en) * 2012-12-19 2014-06-19 Champion Technologies, Inc. Functionalized hydrogen sulfide scavengers
US20140166288A1 (en) * 2012-12-19 2014-06-19 Champion Technologies, Inc. Squeeze treatment for in situ scavenging of hydrogen sulfide
US20140166289A1 (en) * 2012-12-19 2014-06-19 Champion Technologies, Inc. Scavenging hydrogen sulfide
US9108899B2 (en) 2011-12-30 2015-08-18 General Electric Company Sulfide scavengers, methods for making and methods for using
US9273254B2 (en) 2013-12-20 2016-03-01 Ecolab Usa Inc. Amino acetals and ketals as hydrogen sulfide and mercaptan scavengers
US9458393B2 (en) 2014-04-15 2016-10-04 Ecolab Usa Inc. Hydantoins as hydrogen sulfide and mercaptan scavengers
US9663390B2 (en) 2013-05-10 2017-05-30 Ecolab Usa Inc. Reduction of hydrogen sulfide and/or malodor gassing from water via the addition of peroxyacetic acid/hydrogen peroxide product
US9719030B2 (en) 2013-06-27 2017-08-01 Ecolab Usa Inc. Epoxide-based hydrogen sulfide scavengers
WO2018207657A1 (ja) 2017-05-12 2018-11-15 株式会社クラレ 含硫黄化合物除去装置および含硫黄化合物除去方法
US10513662B2 (en) 2017-02-02 2019-12-24 Baker Hughes, A Ge Company, Llc Functionalized aldehydes as H2S and mercaptan scavengers
US10538710B2 (en) 2017-07-13 2020-01-21 Ecolab Usa Inc. Hydrogen sulfide scavengers
US10584286B2 (en) 2015-09-08 2020-03-10 Ecolab Usa Inc. Hydrogen sulfide scavengers
US10703710B2 (en) 2013-01-30 2020-07-07 Ecolab Usa Inc. Hydrogen sulfide scavengers
US11085002B2 (en) 2015-04-22 2021-08-10 Championx Usa Inc. Development of a novel high temperature stable scavenger for removal of hydrogen sulfide
US11499108B2 (en) 2019-01-23 2022-11-15 Championx Usa Inc. Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a Michael acceptor
WO2024064067A1 (en) 2022-09-21 2024-03-28 Championx Llc Compositions and methods for scavenging sulfur-containing compounds

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Cited By (31)

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Publication number Priority date Publication date Assignee Title
US8663457B2 (en) * 2011-11-23 2014-03-04 General Electric Company Methods and compounds for improving sulfide scavenging activity
US20130131387A1 (en) * 2011-11-23 2013-05-23 General Electric Company Methods and compounds for improving sulfide scavenging activity
US9108899B2 (en) 2011-12-30 2015-08-18 General Electric Company Sulfide scavengers, methods for making and methods for using
US9440909B2 (en) 2011-12-30 2016-09-13 General Electric Company Sulfide scavengers, methods for making and methods for using
WO2013181056A1 (en) 2012-05-29 2013-12-05 Baker Hughes Incorporated Synergistic h2s scavengers
EP2859067A4 (en) * 2012-05-29 2016-02-17 Baker Hughes Inc SYNERGISTIC H2S SCAVENGER
US9638018B2 (en) * 2012-12-19 2017-05-02 Ecolab Usa Inc. Scavenging hydrogen sulfide
US9896924B2 (en) 2012-12-19 2018-02-20 Ecolab Usa Inc. Squeeze treatment for in situ scavenging of hydrogen sulfide
US20140166289A1 (en) * 2012-12-19 2014-06-19 Champion Technologies, Inc. Scavenging hydrogen sulfide
WO2014100054A1 (en) * 2012-12-19 2014-06-26 Nalco Company Functionalized hydrogen sulfide scavengers
US20140166288A1 (en) * 2012-12-19 2014-06-19 Champion Technologies, Inc. Squeeze treatment for in situ scavenging of hydrogen sulfide
US10370951B2 (en) 2012-12-19 2019-08-06 Ecolab Usa Inc. Squeeze treatment for in situ scavenging of hydrogen sulfide
US9631467B2 (en) * 2012-12-19 2017-04-25 Ecolab Usa Inc. Squeeze treatment for in situ scavenging of hydrogen sulfide
US9630139B2 (en) * 2012-12-19 2017-04-25 Ecolab Usa Inc. Functionalized hydrogen sulfide scavengers
US20140166282A1 (en) * 2012-12-19 2014-06-19 Champion Technologies, Inc. Functionalized hydrogen sulfide scavengers
US10703710B2 (en) 2013-01-30 2020-07-07 Ecolab Usa Inc. Hydrogen sulfide scavengers
US11339118B2 (en) 2013-01-30 2022-05-24 Ecolab Usa Inc. Hydrogen sulfide scavengers
US9663390B2 (en) 2013-05-10 2017-05-30 Ecolab Usa Inc. Reduction of hydrogen sulfide and/or malodor gassing from water via the addition of peroxyacetic acid/hydrogen peroxide product
US10081561B2 (en) 2013-05-10 2018-09-25 Ecolab Usa Inc. Reduction of hydrogen sulfide and/or malodor gassing from water via the addition of peroxyacetic acid/hydrogen peroxide product
US9719030B2 (en) 2013-06-27 2017-08-01 Ecolab Usa Inc. Epoxide-based hydrogen sulfide scavengers
US9273254B2 (en) 2013-12-20 2016-03-01 Ecolab Usa Inc. Amino acetals and ketals as hydrogen sulfide and mercaptan scavengers
US9458393B2 (en) 2014-04-15 2016-10-04 Ecolab Usa Inc. Hydantoins as hydrogen sulfide and mercaptan scavengers
US11085002B2 (en) 2015-04-22 2021-08-10 Championx Usa Inc. Development of a novel high temperature stable scavenger for removal of hydrogen sulfide
US10584286B2 (en) 2015-09-08 2020-03-10 Ecolab Usa Inc. Hydrogen sulfide scavengers
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AR082165A1 (es) 2012-11-14
EP2593535A4 (en) 2014-04-23
BR112013000890A2 (pt) 2016-05-17
JP2013531728A (ja) 2013-08-08
RU2013102414A (ru) 2014-08-20
RU2563633C2 (ru) 2015-09-20
CN103403129B (zh) 2015-05-20
EP2593535A2 (en) 2013-05-22
WO2012009396A2 (en) 2012-01-19
CN103403129A (zh) 2013-11-20
SG187078A1 (en) 2013-02-28
CA2805404A1 (en) 2012-01-19
CA2805404C (en) 2018-11-27
MX2013000507A (es) 2013-02-27

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