EP4279566A1 - Verbindungen und zusammensetzungen zum absaugen von schwefelwasserstoff und sulfhydrylhaltigen verbindungen - Google Patents

Verbindungen und zusammensetzungen zum absaugen von schwefelwasserstoff und sulfhydrylhaltigen verbindungen Download PDF

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Publication number
EP4279566A1
EP4279566A1 EP22305749.8A EP22305749A EP4279566A1 EP 4279566 A1 EP4279566 A1 EP 4279566A1 EP 22305749 A EP22305749 A EP 22305749A EP 4279566 A1 EP4279566 A1 EP 4279566A1
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EP
European Patent Office
Prior art keywords
compound
hydrocarbon
group
hydrogen sulphide
liquid
Prior art date
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EP22305749.8A
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English (en)
French (fr)
Inventor
Hemant Sunanda MONDKAR
Frederic Tort
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TotalEnergies Onetech SAS
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TotalEnergies Onetech SAS
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Priority to EP22305749.8A priority Critical patent/EP4279566A1/de
Priority to PCT/EP2023/062740 priority patent/WO2023222538A1/en
Publication of EP4279566A1 publication Critical patent/EP4279566A1/de
Pending 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
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • C10L3/101—Removal of contaminants
    • C10L3/102—Removal of contaminants of acid contaminants
    • C10L3/103—Sulfur containing contaminants
    • 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
    • C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
    • C10G75/02—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of corrosion inhibitors
    • 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
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/54—Specific separation steps for separating fractions, components or impurities during preparation or upgrading of a fuel
    • C10L2290/541—Absorption of impurities during preparation or upgrading of a fuel

Definitions

  • the present invention relates to novel compounds useful for scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group.
  • the present invention also relates to the use of such compounds for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream, in particular in hydrocarbon streams such as crude oils, hydrocarbon fractions derived from the distillation of crude oils, natural gas.
  • the present invention also relates to compositions containing such compounds and to a method for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream containing them, comprising contacting said stream with the scavenging compounds of the invention.
  • Hydrogen sulphide is a colourless and fairly toxic, flammable and corrosive gas which has a characteristic odour at a very low concentration. Hydrogen sulphide dissolves in liquid and gaseous streams such as hydrocarbon and water streams and can also be present in the vapour phase above liquid streams as well as in hydrocarbon gas such as LPG and natural gas. The hydrogen sulphide emissions can be harmful to workers operating in the drilling, production, transport, storage, and processing of such streams. It would therefore be desirable for the workers' comfort and safety to reduce or even eliminate the hydrogen sulphide emissions during the handling of said products.
  • a variety of chemical scavengers are available to reduce the concentration of hydrogen sulphide and sulfhydryl-containing compounds in liquid and gaseous streams containing them, in particular aqueous streams and hydrocarbon streams such as gas, crude oils and refined products.
  • Some of the most common methods for treating hydrogen sulphide consist in contacting them with a chemical scavenger such as compounds containing a triazine group, glyoxal, as well as metal-based scavengers.
  • Glyoxal has been used extensively as hydrogen sulphide scavenger but suffers from a major drawback since aqueous glyoxal solutions are highly corrosive and cannot be used for a gas tower application.
  • Triazines have recently become more common chemical scavengers used for treating hydrogen sulphide from hydrocarbon streams. However, many drawbacks are reported that are linked to the use of triazines, including in particular toxicity issues.
  • MBO 3,3'-methylenebis(5-methyloxazolidine
  • Formulations of MBO with promoters also named boosters, have been developed to enhance the efficiency of MBO.
  • WO 2017/102693 describes a composition comprising MBO and one or more additive selected among urea, urea derivatives, amino acids, guanidine, guanidine derivatives or 1,2-diols.
  • Such compounds have a high scavenging efficiency, and therefore allow a very efficient removal of hydrogen sulphide and sulfhydryl-containing compounds in a short contact time.
  • the compounds used in the present invention are not harmful to human beings and to the environment, they do not give rise to corrosive or other aggressive products, or to solid products which may plug lines or deposit in storage vessels.
  • the present invention therefore concerns a compound obtainable by reaction of at least:
  • the present invention further concerns a method for preparing such a compound.
  • the present invention additionally concerns a composition containing at least one liquid solvent and at least one compound as defined above.
  • the compound and the composition of the present invention are particularly useful for scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group such as mercaptans, thiocarboxylic acids, dithiocarboxylic acids.
  • the present invention also concerns the use of a compound as defined above for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream.
  • the present invention further encompasses a method for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream containing them.
  • a method for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream containing them comprises contacting said stream with a compound as defined above.
  • C N compound or group designates a compound or a group containing in its chemical structure N carbon atoms.
  • the compound of the invention is obtainable by reacting at least the following starting materials:
  • the compound of the present invention is effectively obtained by reacting starting materials (i), (ii) and (iii) as disclosed therein.
  • any compound which has the same chemical structure as the compound obtained by reacting starting materials (i), (ii) and (iii), but which is obtained from different stating materials (such as for example from chemical equivalents thereof) is intended to be part of the present invention.
  • the compound of the invention is obtainable by reacting at least starting materials (i), (ii) and (iii), which means that additional compounds, different from compounds (i), (ii) and (iii) may be involved, such as a quaternizing agent as described below.
  • the amino compound (i) is obtained by reacting an acylating agent substituted by a hydrocarbon group and of a compound comprising at least one primary amine group and at least one group selected from primary amines, secondary amines and alcohols.
  • the acylating agent is advantageously selected from mono-or poly-carboxylic acids and their derivatives, particularly their ester, amide or anhydride derivatives.
  • the acylating agent is preferably selected from succinic, phthalic and propionic acids and the corresponding anhydrides.
  • the acylating agent is succinic anhydride.
  • the acylating agent is substituted by a hydrocarbon group which can be chosen from any group containing at least 8 carbon atoms wherein a carbon atom is attached directly to the acylating agent.
  • Such hydrocarbon groups may also contain heteroatoms such as oxygen, nitrogen, halogens. Such heteroatoms may be inserted into the hydrocarbon main chain, or be part of substituent groups (such as hydroxy groups, amino groups, halogen containing groups or halogen atoms) attached to the hydrocarbon main chain.
  • hydrocarbon groups which do not contain such heteroatoms and thus only contain carbon and hydrogen atoms.
  • said hydrocarbon group containing at least 8 carbon atoms is chosen from linear or branched, saturated or unsaturated aliphatic C 8 -C 22 hydrocarbon groups, more preferably from C 8 -C 22 alkyl or mono or polyunsaturated alkenyl groups.
  • Such hydrocarbon groups preferably contain from 8 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms.
  • Examples of hydrocarbon groups substituting the acylating agent include the following groups: n-octyl, n-decyl, n-dodecyl, tetrapropenyl, n-octadecyl, oleyl, octadecyl, dodecenyl.
  • acylating agent substituted by a hydrocarbyl group is dodecenylsuccinic anhydride (DDSA), which corresponds to the following formula:
  • said hydrocarbon group containing at least 8 carbon atoms is chosen from homo- and co-polymers of mono-and di-olefins having from 2 to 10 carbon atoms, such as for example ethylene, propylene, 1-butene, isobutene, butadiene, isoprene, 1-hexene or 1-octene.
  • these olefins are 1-monoolefins.
  • said hydrocarbon group may contain up to approximately 200 carbon atoms.
  • the hydrocarbon substituent of the acylating agent is a polyisobutene (PIB) group.
  • PIB polyisobutene
  • Highly reactive polyisobutenes means polyisobutenes wherein at least 50% by moles, preferably at least 70% by moles or more, of the terminal olefinic double bonds are of the vinylidene type as described in the document EP0565285 .
  • the preferred PIB are those having more than 80% by moles and up to 100% by moles of terminal vinylidene groups such as described in the document EP1344785 .
  • acylating agents substituted by a hydrocarbon group are polyisobutenyl succinic anhydrides (PIBSA).
  • PIBSA polyisobutenyl succinic anhydrides
  • the polyisobutenyl group (PIB group) has, preferably, a number average molecular weight (Mn) between 170 and 2800, for example between 250 and 1500, more preferably between 500 and 1500 and, even more preferably between 500 and 1100.
  • Mn value range between 700 and 1300 is particularly preferred, for example from 700 to 1000.
  • the compound comprising at least one primary amine group and at least one group selected from primary amines, secondary amines and alcohols is preferably chosen from the following amines of formula (I) and (II) below: H 2 N-R'-NHR" (I) and H 2 N-R'-OH (II) wherein
  • Preferred compounds are diamines of formula (I) above, and in particular those wherein R" denotes hydrogen.
  • a particularly preferred compound is ethylenediamine.
  • Further preferred compounds include diamines of formula H 2 N-(CH 2 -CH 2 -O) n -NH 2 , wherein n is an integer ranging from 1 to 4 and preferably n is 2 or 3.
  • Such amines are commercially available under the name Jeffamine ® .
  • the polyhydroxy carboxylic acid (ii) is preferably chosen from those containing from 3 to 10 carbon atoms, more preferably from 4 to 8 carbon atoms, and bearing at least two hydroxy (-OH) groups.
  • Particularly preferred compounds (ii) are sugar acids - that is to say monosaccharides bearing a carboxyl group (-COOH)- and esters thereof, including internal esters (lactone forms).
  • More particularly preferred compounds are aldonic acids such as glyceric acid, xylonic acid, gluconic acid, and gluconolactone.
  • a particularly preferred compound is ⁇ -gluconolactone which corresponds to the following formula:
  • the compound the invention is obtainable by further reacting the condensation product of compounds (i), (ii) and (iii) with (iv) a quaternizing agent.
  • the compound of the invention is under the form of a quaternary ammonium salt of the condensation product of compounds (i), (ii) and (iii).
  • the quaternizing agent (iv) can advantageously be chosen from dialkyl sulfates, carboxylic acid esters, alkyl halides, benzyl halides, hydrocarbon carbonates, and hydrocarbon epoxides optionally mixed with an acid.
  • the present invention further concerns a method of preparation of the scavenging compounds of the invention, comprising the following steps:
  • the scavenging compounds of the invention are obtained by first (step a) reacting said amino compound (i) comprising at least one primary amine group with said polyhydroxy carboxylic acid or ester thereof (ii).
  • Compounds (i) and (ii) are preferably employed in stochiometric amounts, of 0.8 to 1.2 moles of compound (ii) per mole of compound (i).
  • step a the product of step a
  • formaldehyde (iii) The amount of formaldehyde employed typically ranges from 3 to 10 moles per mole of said product of step (a).
  • Steps (a) and (b) are carried out in a suitable medium, such as for example an aromatic solvent such as toluene.
  • a suitable medium such as for example an aromatic solvent such as toluene.
  • the method of the invention comprises:
  • the method of preparation according to the invention comprises after step (b) a further step (c) of quaternization of the compound resulting from step (b).
  • step (b) that is to say, the condensation product of compounds (i), (ii) and (iii)
  • a quaternizing agent (iv) is reacted with a quaternizing agent (iv).
  • Said quaternizing agent (iv) can advantageously be chosen from dialkyl sulfates, carboxylic acid esters, alkyl halides, benzyl halides, hydrocarbon carbonates, and hydrocarbon epoxides optionally mixed with an acid.
  • composition of the present invention contains one or more liquid solvent(s), and one or more scavenging compound(s) as defined above.
  • liquid it is meant a solvent which is in liquid form at ambient temperature (20°C) and atmospheric pressure (1,013.10 5 Pa).
  • the solvent may be chosen from water and organic solvents.
  • the solvent is selected from organic liquid solvents.
  • Such solvents may in particular be chosen from poly alkyl ethers, aliphatic hydrocarbons such as alkanes, aromatic solvents such as aromatic hydrocarbons and aromatic hetero-compounds, and mixtures thereof.
  • Preferred organic solvents are chosen from aromatic solvents, such as N-methylpyrrolidone, xylene, toluene, benzene; and poly alkyl ethers such as butyl carbitol (diethylene glycol monobutyl ether); as well as mixtures thereof.
  • aromatic solvents such as N-methylpyrrolidone, xylene, toluene, benzene
  • poly alkyl ethers such as butyl carbitol (diethylene glycol monobutyl ether); as well as mixtures thereof.
  • organic solvents include those derived from biomass, such as oils of vegetable origin.
  • a particularly preferred solvent is cashew nutshell liquid, also known as CSNL, which is a widely available vegetable oil derived from cashew nut shell.
  • CSNL cashew nutshell liquid
  • CNSL can be used as a mixture with any other solvent such as those described herein.
  • the choice of the solvent mainly depends on the final use of the composition.
  • water may be a solvent of choice.
  • an organic solvent will be preferred.
  • a solvent having a dual solubility i.e. a water solubility and a solubility in hydrocarbons
  • Poly alkyl ethers such as butyl carbitol are preferred solvents since they have such a dual solubility.
  • composition of the invention advantageously contains an amount of solvent ranging from 25 to 95% by weight, preferably from 40 to 90%wt of the composition, more preferably from 50 to 80%wt, relative to the total weight of the composition.
  • composition advantageously contains said scavenging compound in an amount ranging from 5 to 75% by weight, preferably from 10 to 60% by weight, more preferably from 20 to 50% by weight, relative to the total weight of the composition.
  • the compound of the invention as described above is particularly useful for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream.
  • the present invention encompasses the use of a compound as described above for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream.
  • such compound is used in a composition containing one or more liquid solvents as described previously.
  • the present invention also encompasses the use of a composition as described above for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream.
  • the organic compounds comprising at least one sulfhydryl group are especially chosen from mercaptans, thiocarboxylic acids, dithiocarboxylic acids.
  • the liquid or gaseous stream may be a monophasic stream such as in particular an aqueous stream or an organic stream, or a multiphasic stream containing both water and hydrocarbons (such as for instance oil/water or oil/water/gas or gas/water).
  • the compounds of the invention are used for scavenging hydrogen sulphide (H 2 S) and mercaptans (compounds of formula RSH) in a hydrocarbon containing stream.
  • the mercaptans which are eliminated are typically those of formula RSH wherein R is an alkyl or alkenyl group containing from 1 to 8, preferably from 1 to 6 and more preferably from 1 to 4 carbon atoms.
  • the hydrocarbon containing streams are typically selected from crude petroleum oils, hydrocarbon fractions and residues deriving from the distillation thereof, light petroleum gas (LPG) and natural gas, as well as mixtures thereof with aqueous phases such as brine.
  • LPG light petroleum gas
  • natural gas as well as mixtures thereof with aqueous phases such as brine.
  • Such streams contain H 2 S and/or mercaptans in total amounts which may range for example from 1 to 10 000 ppm by weight.
  • the compound of the invention is used in a molar amount which depends on the total content of hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in the liquid or gaseous stream.
  • the compound of the invention is used at a molar ratio of 0.2 to 5 moles per mole of hydrogen sulphide and of organic compounds comprising at least one sulfhydryl group in the liquid or gaseous stream, preferably 0.5 to 2 moles.
  • the method of the invention consists in contacting a liquid or gaseous stream containing hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group with a compound as described above, or with a composition containing such as compound as described above.
  • the liquid or gaseous stream may be monophasic such as in particular an aqueous stream or an organic stream, or multiphasic such as a stream containing both water and hydrocarbons (such as for instance oil/water or oil/water/gas or gas/water).
  • the stream contains hydrocarbons.
  • the stream may be especially selected from crude petroleum oils, hydrocarbon fractions and residues deriving from the distillation thereof such as in particular fuel oils and heavy fuel oils, light petroleum gas (LPG) and natural gas, as well as mixtures thereof with aqueous compositions such as brine.
  • LPG light petroleum gas
  • the amount of composition used par amount of stream depends on the concentration of scavenging active compound in the composition as well as the total content of hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in the liquid or gaseous stream, as explained above.
  • composition is contacted with the liquid or gaseous stream for a time sufficient to achieve an effective scavenging of hydrogen sulphide and of organic compounds comprising at least one sulfhydryl group.
  • DDSA Dodecyl succinic anhydride
  • EDA ethylene diamine
  • toluene 400 mL
  • the reaction mixture was heated to 140° C for 6 h and water released was collected and measured in Dean-Stark trap.
  • the reaction product was isolated by evaporating all the solvent under reduced pressure. 48.0 g (99% yield) of desired product DDSAEDA-IMIDE was obtained as viscous brown liquid, in pure form, it was used as such for further steps without any purifications.
  • DDSAEDA-IMIDE (1.0 eq, 30.8 g, 0.1 mole) and gluconolactone (GL) (1.2 eq, 21.36 g, 0.12 moles) were added to pyridine (50 mL) and the reaction mixture was heated to 85° C for 3 h. The solution turned dark brown after 3 h. Pyridine from the resulting reaction mixture was removed on rotavapor under reduced pressure. The crude dark brown solid was subjected to water wash for 2 h followed by addition of toluene for water removal on rotavapor. On removal of water, product was obtained as a dark brown solid in an average 80 % yield. Resulted product was further purified by precipitation techniques to obtained DDSAEDA-IMIDE-SUGARAMIDE with more than 96% purity.
  • scavenging compound C1 (DDSAEDA-IMIDE-SUGARAMIDE-FORMAL compound below) was obtained in accordance with the following reaction scheme and the synthesis procedure detailed hereunder (step (b) of the method of the invention):
  • DDSAEDA-IMIDE-SUGARAMIDE To a solution of 37% aq. formaldehyde was added DDSAEDA-IMIDE-SUGARAMIDE (12.72 g, 0.02 moles) followed by 2.0 g of 50% NaOH solution. The resultant solution was kept in glass vial for 24 h at 55°C in oven. Saturated brine was added to extract sodium hydroxide into aqueous phase and the organic phase was dried over sodium sulfate to obtain the product as a dark brown viscous liquid in an average 80 % yield. This product was characterized as DDSAEDA-IMIDE-SUGARAMIDE-FORMAL.
  • a DDSAJEDR-IMIDE compound (amino compound (i)) was prepared in accordance with the following reaction scheme and the synthesis procedure detailed hereunder:
  • DDSA Dodecyl succinic anhydride
  • JEDR Jeffamine-148
  • toluene 400 mL
  • the reaction mixture was heated to 140° C for 6 h and water released was collected and measured in Dean-Stark trap.
  • the reaction product was isolated by evaporating all the solvent under reduced pressure. 56.0 gm (99% yield) of desired product DDSAJEDR-IMIDE was obtained as viscous brown liquid, in pure form, it was used as such for further steps without any purifications.
  • DDSAJEDR-IMIDE-SUGARAMIDE compound was prepared in accordance with the following reaction scheme and the synthesis procedure detailed hereunder (step (a) of the method of the invention):
  • the DDSAJEDR-IMIDE-SUGARAMIDE compound was synthesized following exactly the same procedure as described above for the DDSAEDA-IMIDE-SUGARAMIDE compound of Example 1.
  • scavenging compound C2 (DDSAJEDR-IMIDE-SUGARAMIDE-FORMAL compound below) was obtained in accordance with the following reaction scheme and the synthesis procedure detailed hereunder (step (b) of the method of the invention):
  • the DDSAJEDR-IMIDE-SUGARAMIDE-FORMAL compound was synthesized following exactly the same procedure as described above for the DDSAEDA-IMIDE-SUGARAMIDE-FORMAL compound of Example 1.
  • DDSAJEDR-IMIDE-SUGARAMIDE-FORMAL 26.5 g (0.05 moles) of DDSAJEDR-IMIDE-SUGARAMIDE was reacted with 25 g (0.3 moles) of 37% aq. formaldehyde solution in presence of 50% aq. NaOH solution. DDSAJEDR-IMIDE-SUGARAMIDE-FORMAL was obtained as heavy viscous dark brown material.
  • the test was carried out at room temperature.
  • a 250 mL glass purger was charged with 100 mL of an inert solvent.
  • a gas consisting of N 2 containing H 2 S at a concentration of 50 ppm was released by a bubbling tube at a flow rate of 0.4 mL/min into the solvent contained in said purger.
  • the solvent was continuously agitated by using a magnetic stirrer.
  • the gas exiting the solvent and leaving the purger was conveyed to a H 2 S detector.
  • inventive compounds C1 and C2 exhibit an excellent efficiency in scavenging H 2 S.
  • the performances achieved are much above those obtained with the comparative compounds, including MBO which a well known hydrogen sulphide scavenger.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP22305749.8A 2022-05-20 2022-05-20 Verbindungen und zusammensetzungen zum absaugen von schwefelwasserstoff und sulfhydrylhaltigen verbindungen Pending EP4279566A1 (de)

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EP22305749.8A EP4279566A1 (de) 2022-05-20 2022-05-20 Verbindungen und zusammensetzungen zum absaugen von schwefelwasserstoff und sulfhydrylhaltigen verbindungen
PCT/EP2023/062740 WO2023222538A1 (en) 2022-05-20 2023-05-12 Compounds and compositions useful for scavenging hydrogen sulphide and sulfhydryl-containing compounds

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EP22305749.8A EP4279566A1 (de) 2022-05-20 2022-05-20 Verbindungen und zusammensetzungen zum absaugen von schwefelwasserstoff und sulfhydrylhaltigen verbindungen

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0565285A1 (de) 1992-04-10 1993-10-13 BP Chemicals Limited Polyisobutylenbernsteinsäureimide Detergens enthaltende Brennstoffzusammensetzungen
WO1998002501A1 (en) 1996-07-12 1998-01-22 Baker Hughes Incorporated Bisoxazolidine hydrogen sulfide scavenger
EP1344785A1 (de) 2002-03-15 2003-09-17 Bayer Ag Verfahren zur Herstellung hochreaktiver Polyisobutene
WO2017102693A1 (en) 2015-12-14 2017-06-22 Schülke & Mayr GmbH Use of compositions having a content of 3,3'-methylenebis(5-methyloxazolidine) in the removal of sulphur compounds from process streams
WO2020115132A1 (en) * 2018-12-04 2020-06-11 Total Marketing Services Hydrogen sulphide and mercaptans scavenging compositions

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WO2020115132A1 (en) * 2018-12-04 2020-06-11 Total Marketing Services Hydrogen sulphide and mercaptans scavenging compositions

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