WO2017201393A1 - Amines lourdes utilisées comme fixateurs de sulfure d'hydrogène et de mercaptans - Google Patents

Amines lourdes utilisées comme fixateurs de sulfure d'hydrogène et de mercaptans Download PDF

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WO2017201393A1
WO2017201393A1 PCT/US2017/033520 US2017033520W WO2017201393A1 WO 2017201393 A1 WO2017201393 A1 WO 2017201393A1 US 2017033520 W US2017033520 W US 2017033520W WO 2017201393 A1 WO2017201393 A1 WO 2017201393A1
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hydrocarbon
scavenger composition
composition
gas
containing fluid
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Kekeli Ekoue-Kovi
Ian Michael Jones
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Ecolab USA Inc
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Ecolab USA Inc
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    • 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
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12—Organic compounds only
    • C10G21/20—Nitrogen-containing compounds
    • 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
    • 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
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/104—Light gasoline having a boiling range of about 20 - 100 °C
    • 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
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1044—Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
    • 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
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1051—Kerosene having a boiling range of about 180 - 230 °C
    • 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
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1055—Diesel having a boiling range of about 230 - 330 °C
    • 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

  • the present invention generally relates to compositions and methods for scavenging hydrogen sulfide and/or mercaptans from fluids. More particularly, the invention relates to the use of compositions comprising a surfactant and the reaction product between a polyamine and a formaldehyde as a hydrogen sulfide or a
  • mercaptan scavenger for hydrocarbon-containing fluids, particularly for natural gas, crude oil, field oil, fuel oil, naphtha, gasoline, kerosene, diesel, slurry oil, gas oil, resid, refinery gas, coal gas, tar, asphalt, coke gas, ammonia synthesis gas, gas from an industrial gas stream, or a sulfurization plant.
  • Hydrogen sulfide is a very toxic, corrosive, flammable, explosive gas that causes problems in both upstream and downstream operations within the oil and gas industry. Exposure to this gas, even at low concentrations, can cause serious human injury or death. Hydrogen sulfide in natural gas and crude oil reserves is often accompanied by small amounts of mercaptans (RSH), sulfides (R 2 S), polysulfides, and carbonyl sulfide (COS). Considerable expense and effort are expended annually to reduce the amount of H 2 S within gas and oil streams to make them suitable for commercial use.
  • RSH mercaptans
  • R 2 S sulfides
  • COS carbonyl sulfide
  • Natural gas and crude oil streams containing substantial amounts of H 2 S are considered “sour.”
  • aqueous fluids that must be treated to reduce or remove H 2 S, such as waste water streams.
  • Treatments to reduce or remove H 2 S from hydrocarbon or aqueous streams are referred to as “sweetening” treatments because the odor of the processed products is improved by the absence of hydrogen sulfide.
  • a chemical compound that is used to remove or reduce H 2 S levels sometimes is called a “scavenger” or “scavenging agent.” Scavengers that react irreversibly with hydrogen sulfide or other sulfur species and convert them to a more inert form are considered nonregenerative.
  • alkanolamine include N-methyldiethanolamine (MDEA), diethanolamine (DEA), monoethanolamine (MEA) and diglycolamine (DGA). This process is known as gas sweetening.
  • MDEA N-methyldiethanolamine
  • DEA diethanolamine
  • MEA monoethanolamine
  • DGA diglycolamine
  • This process is known as gas sweetening.
  • the absorption compound(s) and H 2 S are then regenerated by various means including heat, pressure reduction, or a combination thereof.
  • the absorption compound(s) is/are reused in the system, and the separated H 2 S is treated by a modified Claus process to form elemental sulfur.
  • scavengers for hydrocarbon streams with small concentrations of H 2 S, the use of scavengers in batch or continuous injection treatments can provide a cost-effective alternative to conventional gas/liquid sweetening processes.
  • Known hydrogen sulfide scavengers includes solid scavengers (e.g. zinc-based or iron-based materials), oxidizing chemicals (e.g. chlorites, nitrites, bromates, iodates, and peroxides), aldehydes (e.g. formaldehyde, glutaraldehyde, acrolein, and glyoxal), reaction products of aldehydes and amines (e.g. triazines), metal carboxylates and other chelates, and other amine based products (e.g. amidines, maleimides, and amine oxides).
  • solid scavengers e.g. zinc-based or iron-based materials
  • oxidizing chemicals e.g. chlorites
  • Some of these known hydrogen sulfide scavengers may be corrosive to some metals such as steel, iron, and aluminum which can be detrimental to the infrastructure used within the upstream and downstream operations within the oil and gas industry.
  • One aspect of the invention is directed to a method of reducing the amount of hydrogen sulfide or mercaptans in a hydrocarbon-containing fluid.
  • the method comprises contacting an effective amount of a scavenger composition with a hydrocarbon-containing fluid.
  • the scavenger composition comprises a surfactant and a reaction product of a polyamine and formaldehyde.
  • Figure 1 is a graph of H 2 S reduction of sour fuel oil treated with various polyalkylamine/formaldehyde reaction products at a dose ratio of
  • Figure 2 is a graph of H 2 S reduction of sour kerosene treated with various polyalkylamine/formaldehyde reaction products at a dose ratio of
  • Figure 3 is a graph of H 2 S reduction of sour kerosene vs. dosage of diethylenetriamine/formaldehyde.
  • the scavenger compositions of a surfactant and a reaction product of a polyamine and formaldehyde described herein provide rapid, efficient, and effective reduction of hydrogen sulfide and mercaptan while being less corrosive to metal in the processing and transportation equipment than traditional scavengers.
  • the present invention is directed towards a method of reducing the amount of hydrogen sulfide or mercaptans in a hydrocarbon-containing fluid.
  • the method comprises contacting an effective amount of a scavenger composition with a hydrocarbon-containing fluid.
  • the scavenger composition comprising a surfactant and a reaction product of a polyamine and formaldehyde.
  • the hydrocarbon-containing fluid can comprise crude oil, field oil, asphalt, naphtha, gasoline, kerosene, diesel, natural gas, refinery gas, coal gas, coke gas, ammonia synthesis gas, an industrial gas stream, or gas from a sulfurization plant.
  • the hydrocarbon-containing fluid can comprise crude oil.
  • the polyamine can comprise ethylenediamine, propylenediamine, diethylenetriam ine, triethylenetetram ine, tetraethylenepentam ine,
  • the polyamine can comprise diethylenetriamine
  • the reaction product can comprise a molar ratio of formaldehyde to polyamine of from about 0.1 : 1 to about 25: 1 , from about 0.1 : 1 to about 20: 1 , from about 0.1 : 1 to about 15: 1 , from about 0.1 : 1 to about 10: 1 , from about 0.1 : 1 to about 5: 1 , from about 0.5:1 to about 25: 1 , from about 0.5:1 to about 20: 1 , from about 0.5: 1 to about 15:1 , from about 0.5:1 to about 10:1 , from about 0.5: 1 to about 5: 1 , from about 1 : 1 to about 25: 1 , from about 1 : 1 to about 20: 1 , from about 1 : 1 to about 15: 1 , from about 1 : 1 to about 10: 1 , from about 1 0.5: 1 to about 5: 1 , from about 1 : 1 to about 25: 1 , from about 1 : 1 to about 20: 1 , from about 1 : 1
  • the reaction product can comprise a molar ratio of
  • formaldehyde to polyamine of from about 1 :1 to about 5: 1 or from about 1 : 1 to about 2: 1 .
  • the surfactant can comprise a quaternary ammonium compound, a trialkylamine oxide, alkoxylated alkylalcohol, or a combination thereof.
  • the surfactant can comprise a tetraalkyl ammonium chloride, a tetraalkyl ammonium sulfate, a (C 8 -C 2 oalkyl)di(Ci-C 4 alkyl) amine oxide, ethoxylated C 4 -Ci 4 alcohol, or a combination thereof.
  • the surfactant can comprise tetralkyl ammonium chloride.
  • the surfactant can be added to the scavenger composition at a
  • the surfactant can be added to the scavenger composition at a concentration from about 1 to about 5 wt.%, based on the total weight of the scavenger composition and more preferably, the surfactant can be added to the scavenger composition at a concentration from about 4 to about 6 wt.%, based on the total weight of the scavenger composition.
  • the scavenger composition can be contacted with the hydrocarbon- containing fluid at a concentration from about 0.2 to about 5 ppm, from about 0.2 to about 4 ppm, from about 0.2 to about 3 ppm, from about 0.2 to about 2 ppm, from about 0.4 to about 5 ppm, from about 0.4 to about 4 ppm, from about 0.4 to about 3 ppm, or from about 0.4 to about 2 ppm, per 1 ppm of hydrogen sulfide or mercaptan detected in the vapor space of the hydrocarbon-containing fluid.
  • the scavenger composition can be contacted with the hydrocarbon-containing fluid at a concentration from 0.4 to 0.8 ppm per 1 ppm of hydrogen sulfide or mercaptan detected in the vapor space of the hydrocarbon- containing fluid.
  • the scavenger composition can be contacted with the hydrocarbon- containing fluid at a temperature from about 20 °C to about 290 °C, from about 20 °C to about 280 °C, from about 20 °C to about 270 °C, from about 20 °C to about 260 °C, from about 20 °C to about 250 °C, from about 20 °C to about 240 °C, from about 20 °C to about 230 °C, from about 20 °C to about 220 °C, from about 20 °C to about 210 °C, from about 20 °C to about 200 °C, from about 20 °C to about 190 °C, from about 20 °C to about 180 °C, from about 20 °C to about 170 °C, from about 20 °C to about 160 °C, from about 20 °C to about 150 °C, from about 20 °C to about 140 °C, from about 20 °C to about 130
  • the scavenger composition can be contacted with the hydrocarbon-containing fluid at a temperature from about 20 °C to about 100 °C.
  • the rate of reaction between the hydrogen sulfide or mercaptan and the reaction product of a polyamine and formaldehyde can be increased using the scavenger composition as compared to the rate of reaction using the reaction product of a polyamine and formaldehyde in the absence of the surfactant.
  • the increased rate of reaction can be demonstrated by a reduction in the hydrogen sulfide or mercaptan concentration of 2, 3, 4, 5, 6, 7, 8, or more times during a residence time of 2 hours at 100°C.
  • the scavenger composition can be injected into, or otherwise brought into contact with, the hydrocarbon-containing fluid in any convenient manner.
  • the scavenger composition may be injected into the hydrocarbon-containing fluid upstream of a refining unit as the fluid passes through a turbulent section of piping.
  • the scavenger composition can be admixed with a hydrocarbon-containing fluid in a holding vessel that is agitated.
  • the scavenger composition can be admixed with the hydrocarbon-containing fluid immediately upstream of a refining unit by injecting it into a turbulent flow.
  • the scavenger composition can be atomized and added to a vaporous hydrocarbon stream using, for example, an injection quill.
  • the methods can be performed wherein the scavenger composition is contacted with the hydrocarbon-containing fluid by injecting the composition into a rundown line for the hydrocarbon-containing fluid.
  • the scavenger composition can also be injected into hydrocarbon-containing fluid using a bubble tower contactor.
  • the scavenger composition can be injected as part of a continuous or batch process.
  • the methods can also include contacting the scavenger composition with the hydrocarbon-containing fluid by injecting the composition into a storage tank with mixing.
  • the scavenger composition may be formulated with a solvent, other suitable materials, or additives, such as dispersants and corrosion inhibitors.
  • suitable solvents for dissolving the compounds include polar and nonpolar solvents.
  • Preferred solvents include methanol, heavy aromatic naphtha, light aromatic naphtha, 2-ethylhexanol, or a combination thereof.
  • the scavenger composition can be used with or without a solvent.
  • the composition can be present at a concentration of from about 5 wt.% to about 95 wt.%, from about 5 wt.% to about 90 wt.%, from about 5 wt.% to about 85 wt.%, from about 10 wt.% to about 95 wt.%, from about 10 wt.% to about 90 wt.%, from about 10 wt.% to about 85 wt.%, from about 15 wt.% to about 95 wt.%, from about 15 wt.% to about 90 wt.%, from about 15 wt.% to about 85 wt.%, from about 20 wt.% to about 95 wt.%, from about 20 wt.% to about 90 wt.%, from about 20 wt.% to about 85 wt.%, from about 25 wt.% to about 95 w
  • the scavenger composition can also be used in applications outside of a refining process.
  • the scavenger composition can be introduced downhole or into the above ground equipment.
  • the scavenger composition can also be introduced into pipelines, storage vessels, and mobile vessels such as trucks, rail cars, and ship cargo holds.
  • the scavenger compositions can be actively or passively mixed with the hydrocarbon- containing fluid being treated.
  • Another aspect of the present invention is a method of reducing the amount of hydrogen sulfide or a mercaptan in an aqueous fluid having a high
  • the method comprises contacting a scavenger composition with the aqueous fluid.
  • the aqueous fluid can include an aqueous stream of a water injection system, waste water associated with a
  • hydrocarbon treatment system a waste water stream in transit to or from a wastewater treatment facility, or waste water from a tanning facility.
  • the reaction product of the polyamine and the formaldehyde are prepared by adding a polyamine to a round bottom flask and adding water slowly for 30 minutes; since the reaction is exothermic, the reaction temperature increases to about 55-60°C.
  • formalin in about a 1 .5: 1 to 3: 1 formalin:amine molar ratio
  • the rate of formalin addition is adjusted to keep the reaction temperature between 50 °C and 66 °C. Once the addition was complete, the reaction mixture is stirred for 1 hour at 60-90 °C.
  • the scavenger composition can comprise an effective amount of the anticorrosion composition described herein and a component selected from the group consisting of an organic solvent, a corrosion inhibitor, an asphaltene inhibitor, a paraffin inhibitor, a scale inhibitor, an emulsifier, a water clarifier, a dispersant, an emulsion breaker, a gas hydrate inhibitor, a biocide, a pH modifier, a surfactant, and a
  • the scavenger composition can comprise from about 20 to about 90 wt.% of the scavenger composition and from about 10 to about 80 wt.% of the component, preferably from about 50 to about 90 wt.% of the scavenger composition and from about 10 to about 50 wt.% of the component, and more preferably from about 65 to about 85 wt.% of the scavenger composition and from about 15 to about 35 wt.% of the component.
  • the component of the composition can comprise an organic solvent.
  • the composition can comprise from about 1 to 80 wt.%, from about 5 to 50 wt.%, or from about 10 to 35 wt.% of the one or more organic solvents, based on total weight of the composition.
  • the organic solvent can comprise an alcohol, a hydrocarbon, a ketone, an ether, an alkylene glycol, a glycol ether, an amide, a nitrile, a sulfoxide, an ester, or a combination thereof.
  • suitable organic solvents include, but are not limited to, methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, methylene glycol, ethylene glycol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, diethyleneglycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel, toluene, xylene, heavy aromatic naphtha, cyclohexanone, diisobutylketone, diethyl ether, propylene carbonate, N-methylpyrrolidinone, ⁇ ,
  • the component of the composition can comprise an additional corrosion inhibitor.
  • the composition can comprise from about 0.1 to 20 wt. %, 0.1 to 10 wt.%, or 0.1 to 5 wt. % of the corrosion inhibitors, based on total weight of the composition.
  • a composition of the invention can comprise from 0.1 to 10 percent by weight of the corrosion inhibitors, based on total weight of the composition.
  • the composition can comprise 1 .0 wt %, 1.5 wt %, 2.0 wt %, 2.5 wt %, 3.0 wt %, 3.5 wt %, 4.0 wt %, 4.5 wt %, 5.0 wt %, 5.5 wt %, 6.0 wt %, 6.5 wt %, 7.0 wt %, 7.5 wt %, 8.0 wt %, 8.5 wt %, 9.0 wt %, 9.5 wt %, 10.0 wt %, 10.5 wt %, 1 1 .0 wt %, 1 1.5 wt %, 12.0 wt %, 12.5 wt %, 13.0 wt %, 13.5 wt %, 14.0 wt %, 14.5 wt %, or 15.0 wt % by weight of the corrosion inhibitors, based on total weight of the composition
  • the corrosion inhibitor can comprise an imidazoline compound, a quaternary ammonium compound, a pyridinium compound, or a combination thereof.
  • the corrosion inhibitor component can comprise an imidazoline.
  • the imidazoline can be, for example, imidazoline derived from a diamine, such as ethylene diamine (EDA), diethylene triamine (DETA), triethylene tetraamine (TETA) etc. and a long chain fatty acid such as tall oil fatty acid (TOFA).
  • the imidazoline can be an imidazoline of Formula (I) or an imidazoline derivative.
  • Representative imidazoline derivatives include an imidazolinium compound of Formula (II) or a bis-quaternized compound of Formula (III).
  • the corrosion inhibitor component can include an imidazoline of Formula
  • R 10 is a C1 -C20 alkyl or a C1 -C20 alkoxyalkyl group
  • R 11 is hydrogen, C1 -C6 alkyl, C1 -C6 hydroxyalkyl, or C1 -C6 arylalkyl
  • R 12 and R 13 are independently hydrogen or a C1 -C6 alkyl group.
  • the imidazoline includes an R 10 which is the alkyl mixture typical in tall oil fatty acid (TOFA), and R 11 , R 12 and R 13 are each hydrogen.
  • the corrosion inhibitor component can include an imidazolinium
  • R 10 is a C1-C20 alkyl or a C1-C20 alkoxyalkyl group; R 11 and R 14 are
  • the imidazolinium compound includes 1 - benzyl-1 -(2-hydroxyethyl)-2-tall-oil-2-imidazolinium chloride.
  • the corrosion inhibitor can comprise a bis-quaternized compound having the formula (III):
  • R-i and R 2 are each independently unsubstituted branched, chain or ring alkyl or alkenyl having from 1 to about 29 carbon atoms; partially or fully oxygenized, sulfurized, and/or phosphorylized branched, chain, or ring alkyl or alkenyl having from 1 to about 29 carbon atoms; or a combination thereof;
  • R 3 and R 4 are each independently unsubstituted branched, chain or ring alkylene or alkenylene having from 1 to about 29 carbon atoms; partially or fully oxygenized, sulfurized, and/or phosphorylized branched, chain, or ring alkylene or alkenylene having from 1 to about 29 carbon atoms; or a combination thereof;
  • l_i and L 2 are each independently absent, H, -COOH, -SO3H, - PO3H2, -COOR5, -CONH2, -CONHR5, or -CON(R 5 ) 2 ;
  • R5 is each independently a
  • Ri and R 2 are each independently C6-C22 alkyl, C8-C20 alkyl, C12-C18 alkyl, C16-C18 alkyl, or a combination thereof;
  • R 3 and R 4 are C-i-C-io alkylene, C 2 -C 8 alkylene, C 2 -C 6 alkylene, or C 2 -C 3 alkylene;
  • n is 0 or 1 ;
  • x is 2;
  • y is 1 ;
  • R 3 and R 4 are -C2H2-; Li is -COOH, -SO3H, or - PO3H2; and L 2 is absent, H, -COOH, -SO3H, or -PO 3 H 2 .
  • Ri and R 2 can be derived from a mixture of tall oil fatty acids and are predominantly a mixture of C17H33 and C17H3-1 or can be Ci 6 -Ci 8 alkyl; R 3 and R 4 can be C 2 -C 3 alkylene such as - C2H2-; n is 1 and L 2 is -COOH or n is 0 and L 2 is absent or H; x is 2; y is 1 ; R 3 and R 4 are -C 2 H 2 -; and l_i is -COOH.
  • the corrosion inhibitor can comprise a bis-quaternized imidazoline compound having the formula (III) wherein Ri and R 2 are each independently C6-C22 alkyl, C8-C20 alkyl, C12-C18 alkyl, or C16-C18 alkyl or a combination thereof; R 4 is C1-C10 alkylene, C 2 -C 8 alkylene, C 2 -C 6 alkylene, or C 2 -C 3 alkylene; x is 2; y is 1 ; n is 0; L-i is- COOH, -SO3H, or -PO3H2; and L 2 is absent or H.
  • Ri and R 2 are each independently C6-C22 alkyl, C8-C20 alkyl, C12-C18 alkyl, or C16-C18 alkyl or a combination thereof; R 4 is C1-C10 alkylene, C 2 -C 8 alkylene, C 2 -C 6 alkylene, or C 2 -C 3
  • a bis-quaternized compound has the formula (III) wherein Ri and R 2 are each independently C16-C18 alkyl; R 4 is -C 2 H 2 -; x is 2; y is 1 ; n is 0; Li is-COOH, -SO3H, or -PO 3 H 2 and L 2 is absent or H.
  • the corrosion inhibitor can be a quaternary ammonium compound of Formula (IV):
  • Suitable alkyl, hydroxyalkyl, alkylaryl, arylalkyi or aryl amine quaternary salts include those alkylaryl, arylalkyi and aryl amine quaternary salts of the formula [N + R 5a R 6a R 7a R 8a ][X ⁇ ] wherein R 5a , R 6a , R 7a , and R 8a contain one to 18 carbon atoms, and X is CI, Br or I.
  • R 5a , R 6a , R 7a , and R 8a can each be independently selected from the group consisting of alkyl (e.g., Ci-Ci 8 alkyl),
  • the mono or polycyclic aromatic amine salt with an alkyl or alkylaryl halide include salts of the formula [N + R 5a R 6a R 7a R 8a ][X ⁇ ] wherein R 5a , R 6a , R 7a , and R 8a contain one to 18 carbon atoms and at least one aryl group, and X is CI, Br or I.
  • Suitable quaternary ammonium salts include, but are not limited to, a tetramethyl ammonium salt, a tetraethyl ammonium salt, a tetrapropyl ammonium salt, a tetrabutyl ammonium salt, a tetrahexyl ammonium salt, a tetraoctyl ammonium salt, a benzyltrimethyl ammonium salt, a benzyltriethyl ammonium salt, a phenyltrimethyl ammonium salt, a phenyltriethyl ammonium salt, a cetyl benzyldimethyl ammonium salt, a hexadecyl trimethyl ammonium salt, a dimethyl alkyl benzyl quaternary ammonium salt, a monomethyl dialkyl benzyl quaternary ammonium salt, or a trialkyi benzyl quaternary
  • the corrosion inhibitor component can comprise a pyridinium salt such as those represented by Formula (V):
  • R 9 is an alkyl group, an aryl group, or an arylalkyi group, wherein said alkyl groups have from 1 to about 18 carbon atoms and X " is a halide such as chloride, bromide, or iodide.
  • X " is a halide such as chloride, bromide, or iodide.
  • alkyl pyridinium salts and alkyl pyridinium benzyl quats.
  • Exemplary compounds include methyl pyridinium chloride, ethyl pyridinium chloride, propyl pyridinium chloride, butyl pyridinium chloride, octyl pyridinium chloride, decyl pyridinium chloride, lauryl pyridinium chloride, cetyl pyridinium chloride, benzyl pyridinium chloride and an alkyl benzyl pyridinium chloride, preferably wherein the alkyl is a Ci-C 6 hydrocarbyl group.
  • the pyridinium compound includes benzyl pyridinium chloride.
  • the corrosion inhibitor components can include additional corrosion inhibitors such as phosphate esters, monomeric or oligomeric fatty acids, or alkoxylated amines.
  • the corrosion inhibitor component can comprise a phosphate ester.
  • Suitable mono-, di- and tri-alkyl as well as alkylaryl phosphate esters and phosphate esters of mono, di, and triethanolamine typically contain between from 1 to about 18 carbon atoms.
  • Preferred mono-, di-and trialkyl phosphate esters, alkylaryl or arylalkyl phosphate esters are those prepared by reacting a C3-C18 aliphatic alcohol with phosphorous pentoxide. The phosphate intermediate interchanges its ester groups with triethylphosphate producing a more broad distribution of alkyl phosphate esters.
  • the phosphate ester can be made by admixing with an alkyl diester, a mixture of low molecular weight alkyl alcohols or diols.
  • the low molecular weight alkyl alcohols or diols preferably include C & to C10 alcohols or diols.
  • triethanolamine are preferred.
  • the corrosion inhibitor component can include a monomeric or oligomeric fatty acid.
  • Preferred monomeric or oligomeric fatty acids are C-H-C22 saturated and unsaturated fatty acids as well as dimer, trimer and oligomer products obtained by polymerizing one or more of such fatty acids.
  • the corrosion inhibitor component can comprise an alkoxylated amine.
  • the alkoxylated amine can be an ethoxylated alkyl amine.
  • the alkoxylated amine can be ethoxylated tallow amine.
  • the component of the composition can comprise an organic sulfur compound, such as a mercaptoalkyl alcohol, mercaptoacetic acid, thioglycolic acid, 3,3'-dithiodipropionic acid, sodium thiosulfate, thiourea, L-cysteine, tert-butyl mercaptan, sodium thiosulfate, ammonium thiosulfate, sodium thiocyanate, ammonium thiocyanate, sodium metabisulfite, or a combination thereof.
  • an organic sulfur compound such as a mercaptoalkyl alcohol, mercaptoacetic acid, thioglycolic acid, 3,3'-dithiodipropionic acid, sodium thiosulfate, thiourea, L-cysteine, tert-butyl mercaptan, sodium thiosulfate, ammonium thiosulfate, sodium thiocyanate,
  • the organic sulfur compound can constitute 0.5 to 15 wt. % of the composition, based on total weight of the composition, preferably about 1 to about 10 wt.% and more preferably about 1 to about 5 wt.%.
  • the organic sulfur compound can constitute 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14 or 15 wt. % of the composition.
  • the composition can be substantially free of or free of any organic sulfur compound other than the compound of formula (1 ).
  • a composition is substantially free of any organic sulfur compound if it contains an amount of organic sulfur compound below the amount that will produce hydrogen sulfide gas upon storage at a temperature of 25°C and ambient pressure.
  • the component of the composition can further include a demulsifier.
  • the demulsifier comprises an oxyalkylate polymer, such as a polyalkylene glycol.
  • the demulsifier can constitute from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of the composition, based on total weight of the composition.
  • the demulsifier can constitute 0.5, 1 , 1 .5, 2, 2.5, 3, 3.5, 4, 4.5 or 5 wt. % of the composition.
  • the component of the composition can include an asphaltene inhibitor.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.1 to 5 wt.%, or from about 0.5 to 4 wt.% of an asphaltene inhibitor, based on total weight of the composition.
  • Suitable asphaltene inhibitors include, but are not limited to, aliphatic sulfonic acids; alkyl aryl sulfonic acids; aryl sulfonates; lignosulfonates;
  • alkylphenol/aldehyde resins and similar sulfonated resins polyolefin esters; polyolefin imides; polyolefin esters with alkyl, alkylenephenyl or alkylenepyridyl functional groups; polyolefin amides; polyolefin amides with alkyl, alkylenephenyl or alkylenepyridyl functional groups; polyolefin imides with alkyl, alkylenephenyl or alkylenepyridyl functional groups; alkenyl/vinyl pyrrolidone copolymers; graft polymers of polyolefins with maleic anhydride or vinyl imidazole; hyperbranched polyester amides;
  • the component of the composition can include a paraffin inhibitor.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.1 to 5 wt.%, or from about 0.5 to 4 wt.% of an additional paraffin inhibitor, based on total weight of the composition.
  • Suitable additional paraffin inhibitors include, but are not limited to, paraffin crystal modifiers, and dispersant/crystal modifier combinations.
  • Suitable paraffin crystal modifiers include, but are not limited to, alkyl acrylate copolymers, alkyl acrylate vinylpyridine copolymers, ethylene vinyl acetate copolymers, maleic anhydride ester copolymers, branched polyethylenes, naphthalene, anthracene, microcrystalline wax and/or asphaltenes.
  • Suitable paraffin dispersants include, but are not limited to, dodecyl benzene sulfonate, oxyalkylated alkylphenols, and oxyalkylated alkylphenolic resins.
  • the component of the composition can include a scale inhibitor.
  • the composition can comprise from about 0.1 to 20 wt.%, from about 0.5 to 10 wt.%, or from about 1 to 10 wt.% of a scale inhibitor, based on total weight of the composition.
  • Suitable scale inhibitors include, but are not limited to, phosphates, phosphate esters, phosphoric acids, phosphonates, phosphonic acids, polyacrylamides, salts of
  • AMPS/AA acrylamidomethyl propane sulfonate/acrylic acid copolymer
  • PHOS/MA phosphinated maleic copolymer
  • the component of the composition can include an emulsifier.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of an emulsifier, based on total weight of the composition.
  • Suitable emulsifiers include, but are not limited to, salts of carboxyhc acids, products of acylation reactions between carboxyhc acids or carboxyhc anhydrides and amines, and alkyl, acyl and amide derivatives of saccharides (alkyl-saccharide emulsifiers).
  • the component of the composition can include a water clarifier.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of a water clarifier, based on total weight of the composition.
  • Suitable water clarifiers include, but are not limited to, inorganic metal salts such as alum, aluminum chloride, and aluminum chlorohydrate, or organic polymers such as acrylic acid based polymers, acrylamide based polymers, polymerized amines, alkanolamines, thiocarbamates, and cationic polymers such as
  • DADMAC diallyldimethylammonium chloride
  • the component of the composition can include a dispersant.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of a dispersant, based on total weight of the composition.
  • Suitable dispersants include, but are not limited to, aliphatic phosphonic acids with 2-50 carbons, such as hydroxyethyl diphosphonic acid, and aminoalkyl phosphonic acids, e.g. polyaminomethylene phosphonates with 2-10 N atoms e.g.
  • each bearing at least one methylene phosphonic acid group examples of the latter are ethylenediamine tetra(methylene phosphonate), diethylenetriamine penta(methylene phosphonate), and the triamine- and tetramine-polymethylene phosphonates with 2-4 methylene groups between each N atom, at least 2 of the numbers of methylene groups in each phosphonate being different.
  • suitable dispersion agents include lignin, or derivatives of lignin such as lignosulfonate and naphthalene sulfonic acid and derivatives.
  • the component of the composition can include an emulsion breaker.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of an emulsion breaker, based on total weight of the composition.
  • Suitable emulsion breakers include, but are not limited to, dodecylbenzylsulfonic acid (DDBSA), the sodium salt of xylenesulfonic acid (NAXSA), epoxylated and
  • propoxylated compounds anionic, cationic and nonionic surfactants, and resins, such as phenolic and epoxide resins.
  • the component of the composition can include an additional hydrogen sulfide scavenger.
  • the composition can comprise from about 1 to 50 wt.%, from about 1 to 40 wt. %, or from about 1 to 30 wt. % of a hydrogen sulfide scavenger, based on total weight of the composition.
  • Suitable additional hydrogen sulfide scavengers include, but are not limited to, oxidants (e.g., inorganic peroxides such as sodium peroxide or chlorine dioxide); aldehydes (e.g., of 1 -10 carbons such as formaldehyde, glyoxal, glutaraldehyde, acrolein, or methacrolein; triazines (e.g., monoethanolamine triazine, monomethylamine triazine, and triazines from multiple amines or mixtures thereof); condensation products of secondary or tertiary amines and aldehydes, and condensation products of alkyl alcohols and aldehydes.
  • oxidants e.g., inorganic peroxides such as sodium peroxide or chlorine dioxide
  • aldehydes e.g., of 1 -10 carbons such as formaldehyde, glyoxal, glutaraldehyde, acrolein
  • the component of the composition can include a gas hydrate inhibitor.
  • the composition can comprise from about 0.1 to 25 wt.%, from about 0.1 to 20 wt. %, or from about 0.3 to 20 wt. % of a gas hydrate inhibitor, based on total weight of the composition.
  • Suitable gas hydrate inhibitors include, but are not limited to,
  • thermodynamic hydrate inhibitors include, but are not limited to, sodium chloride, potassium chloride, calcium chloride, magnesium chloride, sodium bromide, formate brines (e.g.
  • polyols such as glucose, sucrose, fructose, maltose, lactose, gluconate, monoethylene glycol, diethylene glycol, triethylene glycol, mono-propylene glycol, dipropylene glycol, tripropylene glycols, tetrapropylene glycol, monobutylene glycol, dibutylene glycol, tributylene glycol, glycerol, diglycerol, triglycerol, and sugar alcohols (e.g. sorbitol, mannitol)), methanol, propanol, ethanol, glycol ethers (such as diethyleneglycol monomethylether,
  • alkyl or cyclic esters of alcohols such as ethyl lactate, butyl lactate, methylethyl benzoate.
  • the component of the composition can include a kinetic hydrate inhibitor.
  • the composition can comprise from about 5 to 30 wt.%, from about 5 to 25 wt. %, or from about 10 to 25 wt. % of a kinetic hydrate inhibitor, based on total weight of the composition.
  • Suitable kinetic hydrate inhibitors and anti-agglomerates include, but are not limited to, polymers and copolymers, polysaccharides (such as
  • hydroxyethylcellulose HEC
  • carboxymethylcellulose CMC
  • starch starch derivatives, and xanthan
  • lactams such as polyvinylcaprolactam, polyvinyl lactam
  • pyrrolidones such as polyvinyl pyrrolidone of various molecular weights
  • surfactants such as fatty acid salts, ethoxylated alcohols, propoxylated alcohols, sorbitan esters, ethoxylated sorbitan esters, polyglycerol esters of fatty acids, alkyl glucosides, alkyl polyglucosides, alkyl sulfates, alkyl sulfonates, alkyl ester sulfonates, alkyl aromatic sulfonates, alkyl betaine, alkyl amido betaines), hydrocarbon based dispersants (such as
  • lignosulfonates lignosulfonates, iminodisuccinates, polyaspartates), amino acids, and proteins.
  • the component of the composition can include a biocide.
  • composition can comprise from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of a biocide, based on total weight of the composition.
  • Suitable biocides include, but are not limited to, oxidizing and non-oxidizing biocides.
  • Suitable non-oxidizing biocides include, for example, aldehydes (e.g., formaldehyde, glutaraldehyde, and acrolein), amine-type compounds (e.g., quaternary amine compounds and cocodiamine), halogenated compounds (e.g., 2-bromo-2-nitropropane- 3-diol (Bronopol) and 2-2-dibromo-3-nitrilopropionamide (DBNPA)), sulfur compounds (e.g., isothiazolone, carbamates, and metronidazole), and quaternary phosphonium salts (e.g., tetrakis(hydroxymethyl)-phosphonium sulfate (THPS)).
  • aldehydes e.g., formaldehyde, glutaraldehyde, and acrolein
  • amine-type compounds e.g., quaternary amine compounds and cocodiamine
  • Suitable oxidizing biocides include, for example, sodium hypochlorite, trichloroisocyanuric acids, dichloroisocyanuric acid, calcium hypochlorite, lithium hypochlorite, chlorinated hydantoins, stabilized sodium hypobromite, activated sodium bromide, brominated hydantoins, chlorine dioxide, ozone, and peroxides.
  • the component of the composition can include a pH modifier.
  • the composition can comprise from about 0.1 to 20 wt.%, from about 0.5 to 10 wt.%, or from about 0.5 to 5 wt.% of a pH modifier, based on total weight of the composition.
  • Suitable pH modifiers include, but are not limited to, alkali hydroxides, alkali
  • pH modifiers include sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium oxide, sodium carbonate, potassium carbonate, sodium
  • bicarbonate potassium bicarbonate, magnesium oxide, and magnesium hydroxide.
  • the component of the composition can include a surfactant.
  • the composition can comprise from about 0.1 to 10 wt.%, from about 0.5 to 5 wt.%, or from about 0.5 to 4 wt.% of a surfactant, based on total weight of the composition.
  • Suitable surfactants include, but are not limited to, anionic surfactants and nonionic surfactants.
  • Anionic surfactants include alkyi aryl sulfonates, olefin sulfonates, paraffin sulfonates, alcohol sulfates, alcohol ether sulfates, alkyi carboxylates and alkyi ether carboxylates, and alkyi and ethoxylated alkyi phosphate esters, and mono and dialkyi sulfosuccinates and sulfosuccinamates.
  • Nonionic surfactants include alcohol alkoxylates, alkylphenol alkoxylates, block copolymers of ethylene, propylene and butylene oxides, alkyi dimethyl amine oxides, alkyl-bis(2-hydroxyethyl) amine oxides, alkyi amidopropyl dimethyl amine oxides, alkylamidopropyl-bis(2-hydroxyethyl) amine oxides, alkyi polyglucosides, polyalkoxylated glycerides, sorbitan esters and polyalkoxylated sorbitan esters, and alkoyl polyethylene glycol esters and diesters. Also included are betaines and sultanes, amphoteric surfactants such as alkyl amphoacetates and
  • Scavenger compositions made according to the invention can further include additional functional agents or additives that provide a beneficial property.
  • additional agents or additives can be sequestrants, solubilizers, lubricants, buffers, cleaning agents, rinse aids, preservatives, binders, thickeners or other viscosity modifiers, processing aids, carriers, water-conditioning agents, foam inhibitors or foam generators, threshold agents or systems, aesthetic enhancing agents (i.e., dyes, odorants, perfumes), or other additives suitable for formulation with a corrosion inhibitor composition, and mixtures thereof. Additional agents or additives will vary according to the particular corrosion inhibitor composition being manufactured and it's intend use as one skilled in the art will appreciate.
  • compositions can not contain any of the additional agents or additives.
  • the scavenger compositions can be formulated into a treatment fluid comprising the following components. These formulations include the ranges of the components listed and can optionally include additional agents.
  • formaldehyde means formaldehyde, formalin, and/or paraformaldehyde.
  • Hydrocarbon-containing fluid means a liquid, gas, or mixture thereof that predominantly comprises aliphatic and/or aromatic hydrocarbons.
  • the hydrocarbon- containing fluid may be crude, partially refined, or fully refined.
  • the hydrocarbon- containing fluid of the present invention includes, but is not limited to, natural gas, crude oil, field oil, fuel oil, naphtha, gasoline, kerosene, diesel, slurry oil, gas oil, resid, refinery gas, coal gas, tar, asphalt, coke gas, ammonia synthesis gas, gas from a sulfurization plant, or an industrial gas stream.
  • a surfactant can be added to the reaction mixture to comprise 1 -5 % (w/w) of the final solution, after the reaction mixture is allowed to cool to 45 °C.
  • Formulations with a surfactant are listed in Table 2. Table 2.
  • each compound's scavenging efficiencies was investigated using a modified version of the ASTM D5705 vapor phase "Can Test" method typically employed in the Petroleum and Refining Industry to determine H 2 S and mercaptan concentrations above a confined sour hydrocarbon before and after chemical addition.
  • H 2 S detector tubes are available for a wide range of concentrations.
  • mercaptan detector tubes are designed to detect and measure methyl, ethyl and isopropyl mercaptans simultaneously without distinguishing among the mercaptans contaminating the odiferous hydrocarbon.
  • Quart metal or glass cans were filled with 500 ml_ of sour hydrocarbon media (e.g., LVN or kerosene) and quickly capped to ensure H 2 S or mercaptans did not escape.
  • sour hydrocarbon media e.g., LVN or kerosene
  • Each sample was heated for a predetermined time in a hot water bath approximating refinery process and storage temperatures when possible. After the heating cycle had elapsed, the can was shaken to ensure that volatile compounds were in the vapor space of each can, and the vapor headspace concentrations of mercaptans or hydrogen sulfide were determined using detector tubes for the appropriate analyte.
  • Samples were treated with the scavenging compound of interest and then heated in the hot water bath for a second heating cycle for a specified residence time at a specified temperature. Once the second heating cycle had elapsed, reductions in hydrogen sulfide and/or mercaptan concentrations were determined. The method allowed for product evaluation and determination of scavenging efficiencies for each scavenging compound.

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Abstract

La présente invention concerne d'une manière générale des compositions et des procédés de fixation de sulfure d'hydrogène et/ou de mercaptans présents dans des fluides. Plus particulièrement, l'invention concerne l'utilisation de composés comprenant un tensioactif et le produit de la réaction entre une polyamine et un formaldéhyde comme fixateur d'un sulfure d'hydrogène ou d'un mercaptan pour fluides contenant des hydrocarbures, en particulier pour le gaz naturel, le pétrole brut, le pétrole de champs pétroliers, le mazout, le naphta, l'essence, le kérosène, le diesel, les boues de pétrole, le gas-oil, les résidus, le gaz de raffinerie, le gaz de houille, le goudron, l'asphalte, le gaz de coke, le gaz de synthèse de l'ammoniac, le gaz provenant d'une unité de sulfuration, ou de courants de gaz industriels.
PCT/US2017/033520 2016-05-19 2017-05-19 Amines lourdes utilisées comme fixateurs de sulfure d'hydrogène et de mercaptans Ceased WO2017201393A1 (fr)

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JP2021120136A (ja) * 2018-04-27 2021-08-19 株式会社クラレ 含硫黄化合物除去用の組成物
GB201813645D0 (en) * 2018-08-22 2018-10-03 Innospec Ltd Methods, products & uses relating thereto
CN109336293A (zh) * 2018-11-22 2019-02-15 福州宇澄环保工程设计有限公司 中密度纤维板干燥尾气喷淋除尘置换废水中甲醛的去除工艺
US12084615B2 (en) * 2021-09-13 2024-09-10 GAPS Technology, LLC. Chemical compositions and in-situ methods of using same for remediating sulfur-containing compositions and other contaminants in fluids being extracted from the earth
CN115893625B (zh) * 2022-10-26 2023-09-15 中国石油化工股份有限公司 一种用于压返液中有机硫去除的生物脱硫剂及其制备方法

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