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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
  • C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
  • C10L2230/02—Absorbents, e.g. in the absence of an actual absorbent column or scavenger
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
  • C10L2290/14—Injection, e.g. in a reactor or a fuel stream during fuel production
  • C10L2290/141—Injection, e.g. in a reactor or a fuel stream during fuel production of additive or catalyst
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L2300/00—Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308

Definitions

• the present invention relates to a formulated composition useful for scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group, said formulated composition comprises an oxazolidine compound and an aromatic solvent.
• the present invention also relates to the use of an organic solvent, preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably Heavy Aromatic Naphta (HAN), for improving the efficiency of oxazolidine compound(s) in scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group contained in a liquid or gaseous stream, preferably in a hydrocarbon gas stream, especially in a sour gas stream for natural gas production.
• an organic solvent preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably Heavy Aromatic Naphta (HAN)
• HAN Heavy Aromatic Naphta
• the present invention also relates to a method for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream, preferably in a hydrocarbon gas stream, comprising contacting said stream with the formulated composition according to the invention.
• the formulated composition according to the invention is used for treating a hydrocarbon gas stream, for example a sour gas stream for natural gas production, and the method according to the invention comprises injecting said formulated composition into the gas stream to be treated.
• 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 is therefore 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.
• 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.
• promoters such as polyethylene glycol-based promoters
• H 2 S scavenging performance of MBO While enhancing the H 2 S scavenging performance of MBO, these compounds have a major drawback as they present a high viscosity and are solid at room temperature. Therefore, the compositions containing MBO combined with such promoters can hardly be used at cold temperatures nor be injected using high pressure systems due to their viscosity.
• the Applicant has now discovered that the formulated oxazolidine compounds in an organic solvent, preferably in an organic hydrocarbon solvent, more preferably in an aromatic solvent, preferably a Heavy Aromatic Naphta (HAN) solvent, was particularly efficient for scavenging hydrogen sulphide and unwanted organic compounds comprising at least one sulfhydryl group, and in particular enables to improve the scavenging performance of the pure oxazolidine compound.
• an organic solvent preferably in an organic hydrocarbon solvent, more preferably in an aromatic solvent, preferably a Heavy Aromatic Naphta (HAN) solvent
• the present text discloses a formulated composition useful for scavenging hydrogen sulphide and mercaptans in hydrocarbon streams, said composition comprising at least one oxazolidine compound and at least organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN solvent having a kinematic viscosity, measured at 40°C according to ASTM D445 standard, of less than 14 mm 2 /s, preferably between 1 and 10 mm 2 /s.
• the present invention as claimed thus relates to a formulated composition, preferably useful for scavenging hydrogen sulphide and mercaptans in hydrocarbon streams, said formulated composition comprising at least one oxazolidine compound and at least one organic hydrocarbon solvent, preferably at least one aromatic solvent, especially HAN solvent, in a weight ratio oxazolidine compound(s)/aromatic solvent(s) ranging from 40/60 to 95/5, preferably from 50/50 to 90/10, preferably from 55/45 to 80/20, especially from 60/40 to 70/30,said composition having a kinematic viscosity, measured at 40°C according to ASTM D445 standard, of less than 14 mm 2 /s, preferably between 1 and 10 mm 2 /s.
• the composition of the present invention allows achieving an improved scavenging of hydrogen sulphide and organic compounds comprising at least one sulfhydryl group in a short contact time.
• the inventors have surprisingly found that formulating the oxazolidine compound in an organic hydrocarbon solvent, in particular in an aromatic solvent, especially HAN solvent, enables to improve scavenging of hydrogen sulphide and organic compounds comprising at least one sulfhydryl group, compared to a composition of 100% of said oxazolidine compound (in other words, compared to a non-formulated form also called the concentrated or pure oxazolidine compound).
• the improvement of scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group comprised in a stream can be seen when the remaining amount of sulphur compounds in the stream is reduced and/or when the speed of the scavenging of sulphur compounds is increased when contacting the composition according to the invention with said stream compared with the values obtained by using the oxazolidine compounds alone.
• the amount of sulphur compounds in the stream is reduced by at least 10%, preferably by at least 15%, more preferably between 20 to 50%, more preferably between 20 to 40%, compared with the value obtained by using the oxazolidine compounds alone (non-formulated form).
• the reduction of the amount of sulphur compounds in the stream is particularly improved when the composition according to the invention is injected in the stream where the stream is in gas phase, especially for a hydrocarbon gas stream.
• the present invention also relates to the use of the formulated composition of the invention for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream, preferably in a gaseous stream.
• the formulated composition of the invention is used in the treatment of a hydrocarbon gas stream, for example of a sour gas stream for natural gas production.
• the reduction of the amount of sulphur compounds in the gas stream is particularly improved when the formulated composition according to the invention is injected downstream the high-pressure separator enabling the sulphur compounds removal in the gas treatment unit of an oil production device.
• the formulated composition of the present invention allows a faster scavenging, i.e. the amount of sulphur compounds is decreased more rapidly than with a composition comprising 100% of the oxazolidine compound(s).
• the formulated form makes it possible to achieve similar or even improved scavenging performance in comparison with the pure oxazolidine compound.
• the use of a formulated form of the oxazolidine compound to achieve similar or even better scavenging efficiency than the non-formulated form makes it possible to lower the active content of oxazolidine compound that is required for treating said stream, especially said hydrocarbon gas stream.
• toxicity is advantageously lowered as the diluted form is no more toxic by contact with skin.
• the invention also relates to the use of an organic solvent, preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, for improving the efficiency of oxazolidine compound(s) in scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group contained in a liquid or gaseous stream, preferably in a hydrocarbon stream such as crude oil, fuel or natural gas.
• an organic solvent preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN
• the invention relates to the use of an organic solvent, preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, for improving the efficiency of oxazolidine compound(s) in scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group contained in an hydrocarbon gas stream, for example in a sour gas stream for natural gas production, by formulating said oxazolidine compound(s) with said solvent, preferably HAN, and injecting the formulated form into the gas stream to be treated.
• an organic solvent preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN
• the present invention also relates to a method for improving the efficiency of oxazolidine compound(s) in scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group, the method comprising the step of formulating the oxazolidine compound(s) with an organic solvent, preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, preferably HAN.
• an organic solvent preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, preferably HAN.
• the present invention also relates to a method for improving the efficiency of oxazolidine compound(s) in scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group, in an hydrocarbon gas stream, for example in a sour gas stream for natural gas production, the method comprising the step of formulating the oxazolidine compound(s) with an organic solvent, preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, preferably HAN, and injecting the formulated form into the gas stream to be treated.
• an organic solvent preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, preferably HAN
• the present invention also relates to the use of a formulated form of at least one oxazolidine compound in at least one organic solvent, preferably organic hydrocarbon solvent, more preferably aromatic solvent, preferably HAN, especially in a weight ratio oxazolidine compound(s)/aromatic solvent(s) ranging from 40/60 to 95/5, in particular 50/50 to 90/10 and more particularly 55/45 to 80/20, especially 60/40 to 70/30, for improving scavenging of hydrogen sulphide and organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream, in particular in a hydrocarbon stream such as crude oil, fuel or natural gas, preferably in an hydrocarbon gas stream, for example in a sour gas stream for natural gas production, in comparison with the concentrated oxazolidine compound (formulation of 100 wt% of said oxazolidine compounds).
• the kinematic viscosity of the formulated form measured at 40°C according to ASTM D445 standard,
• the present invention also relates to a method for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group such as mercaptans in a liquid or gaseous stream, in particular in a hydrocarbon stream, such as crude oil, fuel or natural gas, comprising contacting said stream with a formulated composition of the invention.
• the present invention relates to a method for scavenging hydrogen sulphide and/or mercaptans in a hydrocarbon gas stream, for example in a sour gas stream for natural gas production, comprising injecting in said gas stream a formulated composition of the invention.
• C N compound or group designates a compound or a group containing in its chemical structure N carbon atoms.
• composition of the invention comprises at least one oxazolidine compound.
• oxazolidine compound refers to a compound comprising at least one oxazolidine cycle, said cycle being substituted or not substituted.
• the oxazolidine compound(s) is (are) selected from compounds comprising one oxazolidine cycle (i.e. mono-oxazolidines) or two oxazolidine cycles (i.e. bisoxazolidines).
• Oxazolidine compounds useful in the present invention and comprising one oxazolidine cycle preferably correspond to the following formula (I): wherein R1 and R2, identical or different, are selected from a hydrogen atom and linear or branched, cyclic or acyclic, alkyl or alkenyl groups having from 1 to 6 carbon atoms, preferably from a hydrogen atom, a methyl and an ethyl group, and
• R3 is selected from a hydrogen atom and linear or branched, cyclic or acyclic, saturated or unsaturated, aromatic or non aromatic hydrocarbon groups having from 1 to 30 carbon atoms, preferably from a hydrogen atom and from linear or branched, cyclic or acyclic, saturated or unsaturated, aromatic or non aromatic hydrocarbon groups having from 1 to 20 carbon atoms.
• R1 and R2, identical or different, are selected from a hydrogen atom and a methyl group.
• R1 and R2 are identical and represent a hydrogen atom and R3 represents a hydrogen atom.
• R1 represents a methyl group
• R2 represents a hydrogen atom
• R3 represents a hydrogen atom
• R1 and R2 are identical and represent a hydrogen atom
• R3 is selected from linear or branched, cyclic or acyclic, saturated or unsaturated, aromatic or non aromatic hydrocarbon groups having from 1 to 20 carbon atoms.
• Oxazolidine compounds useful in the present invention and comprising two oxazolidine cycles preferably correspond to the following formula (II): wherein:
• r denotes 1.
• Preferred bisoxazolidine compounds are 3,3'-methylenebis(oxazolidine) and 3,3'-methylenebis(5-methyloxazolidine) (also known as MBO), which correspond to the following formulae: 3,3'-Methylenebis(oxazolidine) 3,3'-Methylenebis(5-methyloxazolidine) (MBO)
• the oxazolidine compound(s) is (are) selected from 1,3-oxazolidine, 5-methyloxazolidine, 3-(C1-C20)alkyl-oxazolidines, 3,3'-methylenebis(oxazolidine), 3,3'-methylenebis(5-methyloxazolidine) (MBO) and mixtures thereof.
• the oxazolidine compound(s) is (are) present in an amount preferably ranging from 40 to 95 wt%, preferably from 50 to 90 wt%, preferably from 55 to 80 wt%, preferably from 60 to 70 wt%, relative to the total weight of the composition.
• the oxazolidine compound(s) chosen from mono-oxazolidines, bisoxazolidines and mixtures thereof are present in an amount ranging from 40 to 95 wt%, preferably from 50 to 90 wt%, preferably from 55 to 80 wt%, preferably from 60 to 70 wt%, relative to the total weight of the composition.
• the oxazolidine compound(s) chosen from 1,3-oxazolidine, 5-methyloxazolidine, 3-(C1-C20)alkyl-oxazolidines, 3,3'-methylenebis(oxazolidine), 3,3'-methylenebis(5-methyloxazolidine) (MBO) and mixtures thereof are present in an amount ranging from 40 to 95%wt, preferably from 45 to 90%wt, more preferably from 50 to 80%wt, even more preferably from 60 to 70%wt, relative to the total weight of the composition.
• the oxazolidine compound is 3,3'-methylenebis(5-methyloxazolidine) (MBO) and is present in an amount ranging from 40 to 95 wt%, preferably from 50 to 90 wt%, preferably from 55 to 80 wt%, preferably from 60 to 70 wt%, relative to the total weight of the composition.
• MBO 3,3'-methylenebis(5-methyloxazolidine)
• the invention is based on the formulation of said oxazolidine compound(s) in an organic solvent, preferably in an organic hydrocarbon solvent, preferably in an aromatic solvent, especially in a HAN solvent.
• the organic solvent is chosen such that it does not affect the integrity of the oxazolidine compound(s).
• the organic solvent is chosen in order to obtain a stable solution under a wide range of temperatures, especially ranging from -10°C to 60°C.
• the organic solvent is aromatic solvent.
• the aromatic solvent is Heavy aromatic Naphta (or HAN).
• HAN is a mixture of hydrocarbons obtained by the distillation of aromatic fraction.
• HAN consists predominantly of, preferably consists of, aromatic hydrocarbons having a carbon number between 9 and 16, preferably between 9 and 11, and having a boiling point, measured at atmospheric pressure (1,013.10 5 Pa), comprised between 165°C and 290°C, preferably between 181 and 205°C.
• HAN is a liquid solvent.
• the organic solvent preferably organic hydrocarbon solvent, more preferably aromatic solvent, preferably HAN
• a weight ratio oxazolidine compound(s)/solvent(s) ranging from 40/60 to 95/5, in particular 50/50 to 90/10 and more particularly 55/45 to 80/20, especially 60/40 to 70/30.
• the formulated composition of the invention preferably comprises an amount of aromatic solvent(s), preferably HAN, in a weight ratio oxazolidine compound(s)/aromatic solvent(s) ranging from 40/60 to 95/5, in particular 50/50 to 90/10 and more particularly 55/45 to 80/20, especially 60/40 to 70/30, relative to the total weight of the composition.
• aromatic solvent(s) preferably HAN
• the formulated composition of the present invention consists of the oxazolidine compound(s), for example NMO, and aromatic solvent(s), in particular HAN.
• the formulated composition of the invention is a formulation of oxazolidine compound(s), for example NMO, and organic solvent, preferably organic hydrocarbon solvent, preferably aromatic solvent(s), preferably HAN, in weight ratio oxazolidine compound(s)/aromatic solvent(s) ranging from ranging from 40/60 to 95/5, in particular 50/50 to 90/10 and more particularly 55/45 to 80/20, especially 60/40 to 70/30.
• organic solvent preferably organic hydrocarbon solvent, preferably aromatic solvent(s), preferably HAN
• the formulated composition according to the invention can further comprise from 0.1 to 30 wt%, preferably from 0.1 to 20 wt%, preferably from 0.5 to 15 wt%, more preferably from 1 to 10 wt%, based on the total weight of the composition, of one or more additive(s) enhancing the activity of the oxazolidine compounds(s), also known as booster(s).
• the weight ratio between the content of oxazolidine compound(s) and said booster(s) can range from 1 to 100, preferably from 1 to 50, more preferably from 2 to 30, even preferably from 2 to 10.
• the additive enhancing the activity of the oxazolidine compound can be chosen among:
• the resin is bio-based.
• the resin may be for example a non-modified alkylphenol-aldehyde condensation resin, obtainable by condensation of:
• the resin is based on bio-based phenol, for example on cardanol.
• Cardanol can be obtained in a known manner from an oil that is itself obtained from the shell of cashew kernels also known as cashew nutshell liquid.
• said resin can be cardanol-formaldehyde resin.
• the resin may also be a resin obtainable by condensation of:
• the resin is based on bio-based phenol, especially on a renewable compound, namely on Tyrosol which is a natural occurring nontoxic phenol.
• said resin can be a 4-(2-alkoxyethyl)phenol - formaldehyde resin (also named O-alkylated tyrosol formaldehyde resin).
• the resin may be a modified alkylphenol-aldehyde condensation resin that is obtainable by a Mannich reaction of an alkylphenol-aldehyde condensation resin with:
• the modified alkylphenol-aldehyde resin is obtainable by a Mannich reaction of an alkylphenol-aldehyde condensation resin with formaldehyde and at least one alkylpolyamine having at least two primary amine groups and comprising a fatty chain having from 12 to 22 carbon atoms; said alkylphenol-aldehyde condensation resin being itself obtainable by condensation of para-nonylphenol and formaldehyde.
• the polyol ester is chosen from partial sorbitan esters of an unsaturated fatty acid comprising from 10 to 24 carbon atoms, preferably from sorbitan oleate optionally alkoxylated, such as the product available from Oleon under the name Radiasurf ® , for example Radiasurf ® 7348.
• said additive can be the reaction product of a polyisobutenyl succinic anhydride (PIBSA) with a nitrogen-containing compound formula (II): H 2 N-[(CHR 3 -(CH 2 ) p -CHR 4 ) q -NH] m -H wherein:
• PIBSA polyisobutenyl succinic anhydride
• R 1 and R 2 are both methyl group
• R 3 represents a linear or branched alkyl group comprising from 8 to 20 and preferably from 12 to 18 carbon atoms or a phenyl group optionally substituted with an amino group of formula NR'R" wherein R' and R", identical or different, represent alkyl groups containing from 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms
• R 4 represents H, an alkyl group containing from 1 to 4 carbon atoms or an aromatic group such as in particular an alkyl-phenyl group
• X - is a halide ion, preferably a chloride ion.
• the additive may be chosen from dodecyltrimethylammonium chloride, N,N,N',N'-Tetramethyl-p-phenylenediamine dihydrochloride, Di(hydrogenated tallow)dimethylammonium chloride, Tallowtrimethylammonium chloride, Benzyldimethyldodecylammonium chloride, Benzyldimethylhexadecylammonium chloride, and mixture thereof;
• the alkanolamine may be selected from methyldiethanolamine, monoisopropanolamine, polyethanolamine, monoethanolamine, diethanolamine, methylmonoethanolamine, dimethylethanolamine, diethylethanolamine, ethylmonoethanolamine, ethyldiethanolamine, triisopropanolamine, and mixtures thereof, more preferably from methyldiethanolamine, monoisopropanolamine, polyethanolamine, monoethanolamine, and mixtures thereof.
• the alkoxylated amines may be of the following formula: wherein R represents a linear or branched hydrocarbon chain comprising from 1 to 30 carbon atoms, preferably from 6 to 30 carbon atoms, more preferably from 8 to 30 carbon atoms, R' represents an alkylene group comprising from 1 to 4 carbon atoms, preferably from 2 to 3 carbon atoms, more preferably R' represents an ethylene group or a propylene group, and x and y are numbers ranging from 0 to 15, with the proviso that x+y is within the range from 2 to 20, preferably from 5 to 15.
• the alkoxylated amines are chosen from ethoxylated amines, that is to say amines of formula above wherein R' represents an ethylene group, in particular from ethoxylated fatty amines, corresponding to the following general formula: wherein R represents a linear or branched hydrocarbon chain comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms, and x+y is within the range from 2 to 20, preferably from 5 to 15.
• the alkoxylated amine(s) is (are) chosen from ethoxylated fatty amines of formula, more preferably from ethoxylated tallow amines containing an average number of ethoxy units ranging from 5 to 15 (5-15 EO), ethoxylated stearyl amines containing an average number of ethoxy units ranging from 5 to 15 (5-15 EO), ethoxylated coco amines containing an average number of ethoxy units ranging from 5 to 15 (5-15 EO), ethoxylated oleyl amines containing an average number of ethoxy units ranging from 2 to 10 (2-10 EO) and mixtures thereof.
• ethoxylated fatty amines of formula more preferably from ethoxylated tallow amines containing an average number of ethoxy units ranging from 5 to 15 (5-15 EO)
• ethoxylated stearyl amines containing an average number of ethoxy
• Examples of particularly preferred compounds are ethoxylated tallow amine containing 5 ethoxy units (5 EO), ethoxylated tallow amine containing 10 ethoxy units (10 EO), ethoxylated stearyl amine containing 10 ethoxy units (10 EO), ethoxylated coco amine containing 10 ethoxy units (10 EO), ethoxylated oleyl amine containing 2 ethoxy units (2 EO), ethoxylated oleyl amine containing 5 ethoxy units (5 EO);
• the composition of the invention does not contain any booster of the oxazolidine compound.
• the composition according to the invention is free of polyalkylene glycol, preferably is free of polyethylene glycol.
• the formulated composition of the invention may further comprise at least one defoamer.
• the defoamer may be silicon-based or non-silicon-based defoamer.
• silicon-based defoamers mention may be made of polydimethylsiloxane polymers, more preferably from grafted polydimethylsiloxane polymers.
• the defoamer is preferably a bio-based/bio-degradable and non-silicon based defoamer.
• the formulated composition of the invention advantageously contains an amount of defoamer ranging from 0.1 to 10%wt, preferably from 0.5 to 5%wt, more preferably from 1 to 2.5%wt, relative to the total weight of the composition.
• the formulated composition of the invention comprises, in particular consists of at least one oxazolidine compound chosen from mono-oxazolidines, bisoxazolidines and mixtures thereof and at least one aromatic solvent, especially HAN solvent, in a weight ratio oxazolidine compound(s)/aromatic solvent(s) ranging from 40/60 to 95/5, in particular 50/50 to 90/10 and more particularly 55/45 to 80/20, especially 60/40 to 70/30, said composition having a kinematic viscosity, measured at 40°C according to ASTM D445 standard, less than 14 mm 2 /s, preferably between 1 and 10 mm 2 /s.
• said composition comprises, preferably consists of:
• the formulated composition of the invention comprises, in particular consists of:
• compositions are free of additive enhancing the activity of the oxazolidine compound(s).
• the formulated composition of the invention comprises, in particular consists of:
• compositions of the invention are free of polyalkylene glycol, preferably free of polyethylene glycol.
• the present invention also encompasses the use of the formulated 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 and 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 formulated composition of the invention is 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.
• hydrocarbon stream a stream, for example a gas stream, that contains mainly hydrocarbons but may contain a minor quantity of water, in particular in a content less than1 % vol.
• 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 formulated composition of the invention is used for treating a gas stream, preferably a hydrocarbon gas stream, for example a sour gas stream for natural gas production, for example in the gas treatment unit of an oil production device.
• a gas stream preferably a hydrocarbon gas stream, for example a sour gas stream for natural gas production, for example in the gas treatment unit of an oil production device.
• the present invention also concerns the use of an organic solvent, preferably an organic hydrocarbon solvent, more preferably an aromatic solvent, preferably HAN, for improving the efficiency of an oxazolidine compound for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream, in particular in hydrocarbon stream such as crude oil, fuel or natural gas.
• an organic solvent preferably an organic hydrocarbon solvent, more preferably an aromatic solvent, preferably HAN
• the use is for improving the efficiency of oxazolidine compound(s) in scavenging hydrogen sulphide and organic compounds comprising at least one sulfhydryl group contained in a hydrocarbon gas stream, in particular in a sour gas stream for natural gas production, in which said oxazolidine compound(s) is formulated with said solvent, preferably HAN, and the formulated form is injected into the gas stream to be treated.
• said solvent preferably HAN
• the weight ratio oxazolidine compound(s)/ solvent(s) ranges from 40/60 to 95/5, in particular 50/50 to 90/10 and more particularly 55/45 to 80/20, especially 60/40 to 70/30.
• the solvent preferably HAN
• the solvent is used to prepare a formulated composition according to the invention, as disclosed above.
• the specific embodiments as defined above for the formulated composition of the invention also define particular embodiments of the claimed use and method according to the invention.
• the present invention also relates to the use of a formulated composition comprising at least one organic solvent, preferably at least one organic hydrocarbon solvent, more preferably at least one aromatic solvent, and more preferably HAN and at least one oxazolidine compound, to improve scavenging of hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group in a liquid or gaseous stream, preferably in a hydrocarbon gas stream, in comparison with a composition of 100 wt% of said oxazolidine compound.
• the solvent and the oxazolidine compound are preferably such as described below.
• the present invention also relates to a method for scavenging hydrogen sulphide and/or organic compounds comprising at least one sulfhydryl group such as mercaptans in a liquid or gaseous stream comprising contacting said stream with a formulated composition of the invention.
• 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 formulated composition used per amount of stream depends on the concentration of said oxazolidine compound(s) in the formulated 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.
• the formulated 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.
• the formulated composition according to the invention is injected in the stream where the stream is in gas phase.
• the method of the invention is for treating a hydrocarbon gas stream, in particular a sour gas stream for natural gas production, for example in the gas treatment unit of an oil production device.
• the reduction of the amount of sulphur compounds in the gas stream is particularly improved when the composition according to the invention is injected downstream the high-pressure separator, currently used in the gas treatment unit for production natural gas.
• the composition of the invention is injected through a quill injector.
• quill injector it is meant an injection device without any nozzle.
• a quill injector differs from a quill with an atomizer head.
• the present invention also relates to a method for improving scavenging properties of an oxazolidine compound comprising the step of formulating said oxazolidine compound with an organic solvent, preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, preferably HAN.
• an organic solvent preferably an organic hydrocarbon solvent, in particular an aromatic solvent, preferably HAN, preferably HAN.
• the formulation is such that the active content of the formulated product is from 40 to 95 wt%, in particular from 50 to 90 wt%, more particularly from 55 to 80 wt% and preferably from 60 to 80 wt%.
• C1 is a scavenging product of 100% MBO.
• C1 has a kinematic viscosity at 40°C, measured according to ASTM D445 of 14.73 mm 2 /s.
• A1 is a formulated composition according to the invention comprising 60 wt% of MBO and 40 wt% of HAN having a kinematic viscosity at 40°C, measured according to ASTM D445 of 2.7 mm 2 /s.
• the performances of the two scavenging products were evaluated in a field test by injecting them in the gas treatment unit of an oil production plant.
• Injection point of H2S scavenger is located downstream high-pressure separator in gas outlet. Gas flow rate at the injection location during field test was estimated at an average of 12,243 MSm 3 /d.
• the products were injected using an injection quill device without any atomizer head.
• the scavenging potential was evaluated in comparison with MEA Triazine.
• Performances of the composition C1 and A1 are evaluated by the difference of MEA triazine injected downstream. If the composition injected shows improved performances in H 2 S scavenging, the MEA triazine injection will be reduced as the H 2 S measurement at the export is a fixed target.
• a formulated composition according to the invention makes it possible to achieve improved scavenging performance in comparison with pure MBO.

Landscapes

• 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)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Priority Applications (2)

Applications Claiming Priority (1)

Publications (1)

Family

ID=91530332

Family Applications (1)

Country Status (2)

Citations (9)

Family Cites Families (1)

• 2024
  • 2024-06-04 EP EP24305877.3A patent/EP4660284A1/fr active Pending
• 2025
  • 2025-06-04 WO PCT/EP2025/065528 patent/WO2025252824A1/fr active Pending

Patent Citations (9)

Also Published As

Similar Documents

Legal Events