WO2018001630A1 - Composition d'acétals mis en synergie et procédé d'épuration de sulfures et de mercaptans - Google Patents

Composition d'acétals mis en synergie et procédé d'épuration de sulfures et de mercaptans Download PDF

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Publication number
WO2018001630A1
WO2018001630A1 PCT/EP2017/061828 EP2017061828W WO2018001630A1 WO 2018001630 A1 WO2018001630 A1 WO 2018001630A1 EP 2017061828 W EP2017061828 W EP 2017061828W WO 2018001630 A1 WO2018001630 A1 WO 2018001630A1
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composition according
alkyl
formula
compound
aldehyde
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PCT/EP2017/061828
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English (en)
Inventor
Antonio Pedro De Oliveira Filho
Jonathan Wylde
Alina KINA
Grahame Taylor
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Clariant International Ltd
Clariant S. A.
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Publication of WO2018001630A1 publication Critical patent/WO2018001630A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/03—Specific additives for general use in well-drilling compositions
    • C09K8/035—Organic additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
    • C09K8/528—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning inorganic depositions, e.g. sulfates or carbonates
    • C09K8/532—Sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
    • C09K2208/20—Hydrogen sulfide elimination
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
    • C09K2208/26—Gel breakers other than bacteria or enzymes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
    • C09K2208/32—Anticorrosion additives

Definitions

  • the invention relates to a process for scavenging hydrogen sulfide from liquids and/or gas by using acetal in combination with a synergist, a solvent and optionally an emulsion breaker.
  • the formulations containing the inventive composition have particular applicability in scavenging hydrogen sulfide and/or mercaptans yet at the same time prevent the formation of unwanted emulsions and/or deposition of unwanted by products often associated with using chemistries and/or formulations of the prior art.
  • H2S hydrogen sulfide
  • organo-sulfur compounds containing S-H groups also called mercaptans
  • thiol carboxylic acids RC(O)SH dithio acids RC(S)SH
  • Hydrogen sulfide is a flammable, corrosive, and highly toxic gas.
  • H2S is the most reduced form of sulfur and is produced by sulfate reducing bacteria (SRB) that are often found in anaerobic oilfield environments, or caused by thermal cracking and thermochemical sulfate reduction (TSR) by hydrocarbons.
  • SRB sulfate reducing bacteria
  • TSR thermochemical sulfate reduction
  • H2S gas can create a significant integrity risk where it is present at as little as 0.01 psig partial pressure as it is an acid gas and upon dissolving into produced water creates a very corrosive environment.
  • H2S high-density polystyrene
  • SRB waste water treatment
  • biocidal compositions it is easy to lose control of the biology in the system which results in the production of hazardous H2S in the system.
  • biocides are inefficient at removing H2S after it forms and only anecdotally scavenge, via either oxidation (e.g.
  • Suifhydryl compounds and particularly H2S can present environmental, toxicity and integrity challenges in gaseous phases in confined spaces, as for instance in sewage treatment facilities and particularly in shipping and storage containers for moisture sensitive materials that may emit H2S which can sit in the gaseous headspace. It would be desirable to have a scavenger that could reduce the H2S concentrations in such locations. It would be particularly advantageous to have such a scavenger that is active in the absence of an aqueous phase. Furthermore it is desirable to have a scavenger that does not produce unwanted by-products or form emulsions that can inadvertently contaminate the very systems they are treating.
  • WO-98/02501 describes the use of 3,3'-methylene-bis-5-methyloxazolidine bisoxazolidines prepared by the reaction of 1 , 2 or 1 , 3 amino alcohols containing 3 to 7 carbon atoms with aldehydes containing 4 or fewer carbon atoms. The relative oil and water solubility of these products can be controlled through the correct choice of starting materials. These bisoxazolidines react with suifhydryl compounds present in oil and gas streams to neutralize and therefore scavenge them.
  • US-5347004 teaches the use of reaction products of alkoxyalkylene amine, ammonia, and dialkylamines with aldehydes. These products are used to remove H2S from gas streams which are sparged into water solutions of the products.
  • US-4978512 teaches a method for reducing H2S and organic sulfides from gaseous and/or liquid hydrocarbon streams by using a reaction product of a lower alkanolamine comprising 1 to about 6 carbons with a lower aldehyde comprising 1 to about 4 carbons.
  • a preferred embodiment is the reaction product of monoethanolamine and formaldehyde which is perhaps one of the most ubiquitously used triazine chemistries in the oil and gas industry today to scavenge H2S.
  • US-5347004 teaches the use of reaction products of alkoxyalkylene amine, ammonia, and dialkylamines with aldehydes. These products are used to remove H2S from gas streams which are sparged into water solutions of the products.
  • US-4978512 teaches a method for reducing H2S and organic sulfides from gaseous and/or liquid hydrocarbon streams by using a reaction product of a lower alkanolamine comprising 1 to about 6 carbons with a lower aldehyde comprising 1 to about 4 carbons.
  • a preferred embodiment is the reaction product of monoethanolamine and formaldehyde which is perhaps one of the most ubiquitously used triazine chemistries in the oil and gas industry today to scavenge H2S.
  • US-5128049 teaches a unique application method for scavenging agents whereby a dilute solution of a scavenging agent, such as triazine, is injected into an H2S containing fluid, followed by equilibration and a second injection of dilute solution of scavenging agent to further reduce the H2S content of the treated fluid.
  • a dilute solution of a scavenging agent such as triazine
  • EP-0636675 teaches the further use of a scavenging compound comprising a substantially formaldehyde free 1 ,3,5-trimethyl-hexahydro-1 ,3,5-triazine to scavenge gas or liquid hydrocarbon streams containing H2S and/or mercaptans.
  • the compound described is preferably prepared by the reaction of methylamine and formaldehyde.
  • US-8512449 teaches a method for formulating an oil-soluble triazine sulfide scavenger comprising a liquid sulfide-scavenging composition comprising from about 25 to 80 % by volume of a triazine, from about 15 to 50 % by volume of a glycol ether, and from about 5 to 40 % by volume of an alcohol, with a maximum water content of about 15 % by volume, and being oil soluble.
  • the triazine used is a reaction product of a Ci to C6 alkanolamine and a Ci to C6 aldehyde, where the Ci to C6 moiety in each instance is a straight or branched chain alkyl group.
  • WO-2014/031537 teaches the use of an aldehyde releasing compound, preferably hydantoins, to remove sulfhydryl compounds from hydrocarbon fluids.
  • US-3928211 describes the use of inorganic zinc salts (most preferably zinc carbonate) preferably dispersed into aqueous or non aqueous oil well drilling fluids with an organic dispersant such as lignin containing materials.
  • US-4147212 teaches the use of a water soluble zinc ammonium carbonate complex used to remove hydrogen sulfide from oils and gases by contact with aqueous solutions of the complex.
  • US-6599472 discloses the use of metal salt carboxylic acids that are soluble in hydrocarbon oils and are used to inactivate odor producing sulfhydryl compounds.
  • Preferred embodiments are zinc neodecanoic acid but equally claimed are carboxylic acids of naphthenic acids, neoacids, isoacids and Guerbet acids and mixtures thereof.
  • WO-2014/130503 teaches the use of zinc carboxylates, preferably zinc octoate or zinc 2-ethyl hexanoic acid in combination with viscosity improver selected from the group consisting of glycol ethers having from about 4 to about 15 carbon atoms, and/or alkyl alcohols having from about 1 to about 10 carbons, and/or with additional hydrocarbons from about 7 to about 30 carbons.
  • the resultant formulations are used to scavenge hydrogen sulfide gas.
  • WO-2013/181056 teaches the synergistic hydrogen sulfide scavenging obtained when use of a metal salt, preferably selected from zinc chloride, zinc acetate, zinc octanoate, and zinc salts containing at least one hydrocarbyl group of at least 4 carbon atoms in combination with an oil soluble amine formaldehyde reaction product (triazine).
  • WO-2002/051968 teaches a process for reducing the level of hydrogen sulphide in a liquid or gas by treatment of the liquid or gas with an H2S-scavenger product derivable 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.
  • US-2015/0025258 discloses the use of particulate zinc oxide salts blended in a mixture of two or more carboxylic acids selected from the group consisting of acetic acid, oleic acid, isobutyric acid, lineoleic acid and neodecanoic acid, for the scavenging of hydrogen sulfide.
  • the object of this invention is to provide formulations which can be used for scavenging of suifhydryl compounds in crude oil, gas production, water production, water injection and combinations thereof, preferably, but not limited to, H2S and/or mercaptans.
  • the formulations of the invention should have particular applicability in scavenging suifhydryl compounds and should be notable for improved
  • composition comprising of at least one reaction product between a mono- or polyhydric alcohol and an aldehyde or ketone ("acetal") combined with a synergist, optionally an emulsion breaker, and a solvent comes to overcome the very slow kinetics of scavenging H2S provided by acetals alone.
  • acetal aldehyde or ketone
  • Ra is Alkyl, hydroxyalkyl or alkoxyalkyl with Ci to C10.
  • Ra is Chh or CH2CH2OH.
  • the composition of the first aspect as a sulfhydryl scavenger for application in oilfield operations and process systems.
  • a process for scavenging sulfhydryl compounds in oilfield operations and process systems comprising adding to a system susceptible to production of sulfhydryl compounds the composition of the first aspect.
  • a compound of formula (1) there is provided the use of a compound of formula (1)
  • Ra Ci to Cio Alkyl, Ci to C-io hydroxyalkyl or Ci to Cio alkoxyalkyl Ra Ci to Cio Alkyl, Ci to C-io hydroxyalkyl or Ci to Cio alkoxyalkyl.
  • Ra is Chb or CH2CH2OH.
  • At least one demulsifier is present in any aspect of the invention.
  • the group 1 compound is the reaction product of an alcohol and an aldehyde or ketone.
  • the reaction product is a hemi-acetal.
  • An aldehyde or ketone starting material may contain one or more carbonyl groups, especially one or two carbonyl groups, and comprises aliphatic, alicyclic and/or aromatic moieties, usually aliphatic, alicyclic and/or aromatic hydrocarbon moieties or hydrogen. More especially the compound is aliphatic or cycloaliphatic or contains both aliphatic and cycloaliphatic moieties. Aliphatic or cycloaliphatic groups or moieties may be saturated or unsaturated, but are usually saturated.
  • the carbonyl compound is an aldehyde, more especially a mono- or di-aldehyde, commonly and most preferred formaldehyde.
  • formaldehyde includes paraformaldehyde, formalin and other chemical forms from which the basic structure HCHO can be derived.
  • suitable aldehydes include, for example, glyoxal, acetaldehyde, propionaldehyde, butyraldehyde and glutaraldehyde.
  • Suitable ketones include, for example, acetaone, methyl ethyl ketone, methyl isopropyl ketone, and hexanones and heptanones having a total of 6 or 7 carbon atoms respectively.
  • acetal shall refer to the reaction product of any alcohol and any aldehyde or ketone. It means the reaction products of formaldehyde, i.e. formals, as well.
  • Mixtures of two or more carbonyl compounds for example two or more of the aldehydes mentioned above, e.g. formaldehyde and one or more other aldehydes, may be used if desired.
  • An alcohol starting material contains one or more hydroxy groups.
  • the alcohol comprises aliphatic, alicyclic and/or aromatic moieties, usually aliphatic, alicyclic and/or aromatic hydrocarbon moieties, and more especially the compound is aliphatic or cycloaliphatic, or contains both aliphatic and cycloaliphatic moieties.
  • Aliphatic or cycloaliphatic groups or moieties may be saturated or unsaturated, but are usually saturated. More especially the compound is aliphatic.
  • the alcohol contains, for example, 1 to 6 hydroxy groups and is, for example, ethylene glycol, propylene glycol, glycerol, ethyl alcohol, methanol, n-butanol, a sugar molecule, or a polyvinyl alcohol of low molecular weight such that the reaction product with the carbonyl starting material remains a liquid.
  • the most preferred alcohol is glycerol.
  • reaction product is a hemi-acetal.
  • Ri is H or Ci to Cs alkyl
  • R 2 is CH 2 OH.
  • R 3 is H, CH 3 , (CH 2 )nCH 3 , (CHR 4 )nCH3, CH 2 OH
  • n 1 to 10
  • R 4 is H, CHs, (CH 2 )nCH 3 , (CHR 4 )nCH3, CH2OH.
  • n 1 to 10, preferably between 1 and 2
  • R5 is H, CH3, (CH2)zCH3, with the proviso that not all of R5 are hydrogen, z is 1 to 10, and
  • x 1 to 5.
  • the solvent may be any solvent suitable, for dissolving or suspending the hemi- acetal components described in Group 1.
  • the solvent is water, alcohol, a non-alcoholic organic solvent, and/or any combination thereof.
  • the alcohol may include any alcohol suitable as a solvent and for use with oil recovery operations.
  • Preferred are alkyl alcohols having from 1 to 10 carbon atoms, e.g. isopropyl alcohol, methanol, ethanol, propanol, butanol.
  • Another preferred type of alcohols is glycols, e.g. ethylene glycol, propylene glycol and butylene glycol.
  • Another preferred type of alcohols is glycol ethers having from 4 to 15 carbon atoms.
  • Suitable glycol ethers include oligoethylene glycols, oligopropylene glycols, or any combination thereof. Oligoethylene glycols and oligopropylene glycols as used herein preferably have a number average molecular weight between 200 and 1000 g/mol.
  • the organic solvent includes aromatic compounds, either alone or in any combination with the foregoing.
  • the aromatic compounds have a molecular weight from about 70 to about 400, preferably from about 100 to about 200 g/mol. In a preferred
  • aromatic hydrocarbon solvents having from 6 to 30 carbon atoms are used.
  • suitable aromatic compounds include toluene, xylene, naphthalene, ethylbenzene, trimethylbenzene, and aromatic naphtha (AN), other suitable aromatic compounds, and any combination of the foregoing.
  • AN aromatic naphtha
  • the amount of hemiacetal in the composition in relation to the solvent may vary in some embodiments depending upon factors such as temperature, time, and type of hemiacetal. For instance a higher ratio of
  • the group 3 component is optional.
  • This group comprises emulsion breakers, or demulsifiers or non-emulsifiers.
  • the purpose of having these compounds present is to prevent the formation of emulsions caused by the reaction products of such as iron present in oil mainly because of the corrosion of pipelines and equipment caused by H2S present. Fine solids of iron sulfide stabilize the water present in the oil generating a stable emulsion.
  • the purpose of the demulsifier molecule is to break the oil/water emulsion by creating a preferentially water wet surface on the metal sulfide and also to modify the surface tension at the oil/water interface which is stabilized by the metal sulfides to one allowing coalescence of the emulsion.
  • suitable polymeric nonionic surfactants include polysorbates, fatty alcohols such as cetyl alcohol and oleyl alcohol, polymers comprising ethylene oxide, polymers comprising propylene oxide, ethylene oxide-propylene oxide copolymers, alkyl polyglucosides such as decyl maltoside, alkylphenol polyethylene oxide, alkyl polyethylene oxide, and ethoxylated and/or propoxylated alkyl phenol-formaldehyde resins.
  • the emulsion breaker components refer to components or additives that may be added as part of the composition comprising the instant invention and can be described as polymeric nonionic surfactants.
  • suitable polymeric nonionic surfactants include
  • the emulsion breaker is a compound according to the formula (6)
  • n a number from 1 to 100 is.
  • Rio is an ethylene or a propylene group. Rio may represent mixtures of different C2 to C 4 alkylene groups, preferably ethylene and propylene groups.
  • Rn is a C 4 to C12 alkyl group, more preferably a tertiary butyl group or an iso-nonyl group.
  • R10, R11 and k may be the same in each of the repeating units, or they may differ from unit to unit.
  • k is a number from 2 to 20. In another preferred embodiment m is a number from 3 to 20.
  • the demulsifier is a mixture of at least one compound of formula (6) and at least one compound of formula (7).
  • Such mixture preferably contains (6) and (7) in a weight ratio of from 5:1 to 1 :5, more preferably in a weight ratio of from 3:1 to 1 :3.
  • the polymeric nonionic surfactant is preferably dissolved or suspended in a solvent.
  • Any solvent suitable for dissolving or suspending a polymeric nonionic surfactant may be used.
  • suitable solvents include water, butylglycol, ethylene glycol, propylene glycol, butylene glycol, oligoethylene glycols, oligopropylene glycols, ethers, alcohols, toluene, xylene, aromatic naphtha, or any combination thereof.
  • the alcohol may include any alcohol suitable for use with oil recovery and for dissolving the polymeric nonionic surfactant and is preferably selected from the group consisting of isopropyl alcohol, methanol, ethanol, propanol, butanol or any combination thereof.
  • This group comprises the synergist component of the formulation.
  • the synergist is a compound according to formula (1)
  • Ra is Ci to Cio Alkyl, Ci to Cio hydroxyalkyl or Ci to Cio alkoxyalkyl.
  • Ra is CH3 or CH2CH2OH.
  • corrosion inhibitors may be added to the target system separately and/or in association with the compounds described in group 1 , 2 and 3.
  • the addition of these Group 5 components serves to add corrosion inhibition functionality to the overall product.
  • the corrosion inhibitor serves to reduce the overall corrosivity of the treatment, protecting the tubulars and production equipment from corrosion caused by oilfield fluids into which the instant invention is deployed.
  • the corrosion inhibitor may also be formed in sites by the constituents of the instant invention together with H2S or other sulfhydryl compounds.
  • the product generated from the reaction with H2S with MBO is a morpholine and it is recognized as a good corrosion inhibitor protecting the integrity of the whole system.
  • a preferred embodiment of the current invention is to use alkyl dimethyl benzyl ammonium chloride according to formula (8) as a corrosion inhibitor that also provides functionality as an interfacial tension reducer.
  • R9 is Ce to C18 alkyl.
  • composition may additionally contain biocides, for example, formaldehyde or glutaraldehyde, water dispersants, antifoams, oxygen scavengers and/or flocculants. There may also be added to the water to be treated oxygen
  • scavengers such as polyacrylamide dispersants, antifoams such as acetylenic diols, silicones or polyethoxylated antifoams.
  • the inventive composition comprises 1 to 95 wt.-% of the hemiacetal described above in group 1 , preferably between 20 and 75 wt.-%.
  • the inventive composition comprises 1 to 50 wt.-% of the solvent described above in group 2, preferably between 5 and 25 wt.-%. In a preferred embodiment, the inventive composition comprises 0.1 to 10 wt.-% of at least one emulsion breaker described above in group 3, preferably between 0.5 and 2 wt.-%. In a preferred embodiment, the inventive composition comprises 1 to 20 wt.-% of the synergist described above in Group 4, preferably between 5 and 15 wt.-%.
  • the inventive composition comprises 0.1 to 5 wt.-% of the corrosion inhibitor described above in group 5, preferably between 0.2 and 2 wt.-%.
  • compositions may in a preferred embodiment comprise water.
  • the water in the composition may be formed during the manufacture of hemi-acetals, or it can added into the composition to balance the formulation. It can be present in concentration from 1 to 50 wt.-%, preferably between 5 and 15 wt.-%. In another preferred embodiment water is present to balance up to 100 wt.-%.
  • any balance remaining after addition of components of groups 1 - 4 or groups 1 - 5 described above is preferably made up with water and/or glycol and/or alcohol based solvents.
  • the alcohols and solvents are preferably selected from, but not limited to, methanol, ethanol, propan-1-ol, propan-2-ol, monoethylene glycol, triethylene glycol, propylene glycol and / or 2-butoxyethanol.
  • the inventive composition is preferably applied in concentrations between 50 and 35,000 mg/L, preferably between 100 and 30,000 mg/L based on the volume of oil or gas production to a production system where sulfhydryl compounds are present. The exact concentration will preferably depend on the formulation activity itself, the type of sulfhydryl compounds required to be scavenged, static
  • the inventive system can provide substantial scavenging of sulfhydryl compounds from the produced liquids in order to maintain the flowability of hydrocarbon production and the quality of the hydrocarbon produced product as it is transported to market.
  • concentrations refer to the concentration of the reaction product between a mono- or polyhydric alcohol and an aldehyde or ketone.
  • the present invention also includes a process for applications using the compositions above for application to be deployed in scavenging of sulfhydryl compounds present in the drilling and the production cycle, particularly as a component of well work-over, well intervention, production enhancement and flow assurance packages.
  • the injection fluid containing the composition of the instant invention may additionally contain other ingredients known to those familiar with the art.
  • Such other ingredients include acids, dispersants, viscosifiers, lubricity agents, scale inhibitors, friction reducers, crosslinker, surfactants, scavenger, pH adjuster, iron control agents, breakers; this is especially true if any produced water (or recycled water) is in contact with the compositions of the instant invention.
  • Employing the embodiments of the instant invention improves the scavenging of sulfhydryl compounds while not causing formation of complex and difficult to treat emulsions. Furthermore the embodiments of the instant invention will not corrode the oilfield equipment that it comes into contact with, nor will it allow the deposition of unwanted solids, such as metal sulfide scales, so often found with applications of the prior art. Other applications of the embodiments of the instantaneous invention include treating water for downhole injection for pressure support, treatment of drilling and work-over operations, wettability alteration and well cleanout.
  • Example 1 (comp.) - Preparation of MEG-hemi-acetal with active ingredient of
  • the second method of analysis was done by reacting the product with HCI first, then reacting the formaldehyde released in this reaction with 2,4-dinitrophenylhydrazine (DNPH) and finally, after derivation, it was analyzed by using HPLC/UV.
  • DNPH 2,4-dinitrophenylhydrazine
  • the second method of analysis was to determine the total amount of hemiacetal and formaldehyde in the final product, that was higher than 90 wt.-%, and
  • Example 2 (comp.) - Preparation of glycerol hemi-acetal with active ingredient of
  • paraformaldehyde (93 wt.-%) was added over a period of approximately
  • a comparison between the inventive and the comparative example shows that addition of a small amount of hexahydro-1 ,3,5-trimethyltriazine will increase the H2S scavenging activity of an acetal drastically.
  • the enhancement in scavenging efficiency exceeds the stoichiometric H2S scavenging capacity of the added hexahydro-1 ,3,5-trimethyltriazine considerably.

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  • General Life Sciences & Earth Sciences (AREA)
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Abstract

La présente invention a trait à une composition comprenant I. au moins un produit de réaction entre un alcool mono ou polyhydrique et un aldéhyde ou une cétone, et II. au moins un solvant, et IV. au moins un composé de formule (1) où Ra est un alkyle en C1 à C10, un hydroxyalkyle en C1 à C10 ou un alcoxyalkyle en C1 à C10, les constituants I, II et IV étant différents les uns des autres.
PCT/EP2017/061828 2016-07-01 2017-05-17 Composition d'acétals mis en synergie et procédé d'épuration de sulfures et de mercaptans WO2018001630A1 (fr)

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Cited By (6)

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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
WO2020256920A1 (fr) * 2019-06-19 2020-12-24 Bl Technologies, Inc. Solutions stabilisées concentrées en formaldéhyde et leurs procédés d'utilisation
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

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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
EP0405341A1 (fr) * 1989-06-26 1991-01-02 Henkel Corporation Composition masquante et procédÀ©
WO2002051968A1 (fr) * 2000-12-27 2002-07-04 M-I L.L.C. Procede de reduction ou d'elimination de sulfure d'hydrogene
EP2267098A1 (fr) * 2009-06-26 2010-12-29 M-i Swaco Norge As Compositions purificatrices et leur utilisation

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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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