WO2013174902A1 - Procede d'elimination selective du sulfure d'hydrogene de melanges gazeux et utilisation d'un thioalcanol pour l'elimination selective du sulfure d'hydrogene - Google Patents
Procede d'elimination selective du sulfure d'hydrogene de melanges gazeux et utilisation d'un thioalcanol pour l'elimination selective du sulfure d'hydrogene Download PDFInfo
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- B01D—SEPARATION
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- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1468—Removing hydrogen sulfide
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- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1462—Removing mixtures of hydrogen sulfide and carbon dioxide
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- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1425—Regeneration of liquid absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D—SEPARATION
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- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/48—Sulfur compounds
- B01D53/52—Hydrogen sulfide
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20405—Monoamines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2252/20—Organic absorbents
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- B01D2252/20431—Tertiary amines
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- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20478—Alkanolamines
- B01D2252/20484—Alkanolamines with one hydroxyl group
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20478—Alkanolamines
- B01D2252/20489—Alkanolamines with two or more hydroxyl groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/205—Other organic compounds not covered by B01D2252/00 - B01D2252/20494
- B01D2252/2056—Sulfur compounds, e.g. Sulfolane, thiols
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/50—Combinations of absorbents
- B01D2252/504—Mixtures of two or more absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/60—Additives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/60—Additives
- B01D2252/602—Activators, promoting agents, catalytic agents or enzymes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/304—Hydrogen sulfide
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/306—Organic sulfur compounds, e.g. mercaptans
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/308—Carbonoxysulfide COS
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- 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
- C10L2290/12—Regeneration of a solvent, catalyst, adsorbent or any other component used to treat or prepare a fuel
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
Definitions
- the present invention relates to a process for selectively removing hydrogen sulfide from gaseous mixtures.
- the present invention relates to a process for selectively removing hydrogen sulfide in the presence of carbon dioxide in a gaseous mixture containing hydrogen sulfide and carbon dioxide.
- the present invention further relates to the use of a thioalkanol for the selective removal of hydrogen sulfide.
- the present invention further relates to the use of an absorbent solution comprising a thioalkanol for the selective removal of hydrogen sulfide in the presence of carbon dioxide in a gaseous mixture containing hydrogen sulfide and carbon dioxide.
- an absorbent solution comprising a thioalkanol for the selective removal of hydrogen sulfide in the presence of carbon dioxide in a gaseous mixture containing hydrogen sulfide and carbon dioxide.
- carbon as well as the use of a thioalkanol as an additive to an absorbent solution to increase the selectivity of said absorbent solution with respect to the removal of hydrogen sulfide in the presence of carbon dioxide in a gaseous mixture containing hydrogen sulphide and carbon dioxide.
- the invention applies in particular to the selective elimination of 3 ⁇ 4S in natural gases, in order to provide on the one hand a gas stream free of 3 ⁇ 4S or having a 3 ⁇ 4S content below a specified threshold, for example for supplying a natural gas distribution network for domestic use, and other a directedS-enriched acidic gas stream is for example intended for supplying a sulfur production plant, for example by the CLAUS process, or for the synthesis of thio-organic compounds.
- gaseous mixtures and in particular of gaseous hydrocarbon mixtures such as natural gas, or others such as synthesis gases, in order to remove contaminants and impurities is a common operation in industry.
- impurities and contaminants include “acid gases” such as, for example, carbon dioxide (CO 2 ) and hydrogen sulphide (H 2 S); other sulfur compounds different from hydrogen sulfide (3 ⁇ 4S) such as for example carbonyl sulphide (COS) and mercaptans (R-SH, where R is an alkyl group); the water ; and some hydrocarbons.
- acid gases such as, for example, carbon dioxide (CO 2 ) and hydrogen sulphide (H 2 S)
- other sulfur compounds different from hydrogen sulfide (3 ⁇ 4S) such as for example carbonyl sulphide (COS) and mercaptans (R-SH, where R is an alkyl group)
- COS carbonyl sulphide
- R-SH mercaptans
- Carbon dioxide and hydrogen sulphide can account for a significant portion of the gaseous mixture from a natural gas pool, typically from 3% to 70% by volume, while COS is present in smaller amounts, typically ranging from from 1 to 100 ppm by volume, and that the mercaptans are present at a content generally lower than 1000 ppm by volume, for example between 5 ppm by volume and 500 ppm by volume.
- Natural gas from a deposit undergoes several treatments to meet specifications dictated in particular by commercial constraints, transportation constraints or constraints related to safety.
- This last treatment consists of separating methane gas, which is sent into the distribution network, ethane, propane, butane and gasolines forming liquefied petroleum gas ("LPG").
- LPG liquefied petroleum gas
- the specifications on the acid gas content in the treated gas are specific to each of the products in question.
- the richeS-rich gas sent to the CLAUS facility should generally comprise at least 30% by volume of 3 ⁇ 4S.
- the known methods for the selective removal of 3 ⁇ 4S can be classified into three main categories.
- the processes which implement physical solvents and which are based on the physical absorption of acid gases in this solvent belong the processes which implement physical solvents and which are based on the physical absorption of acid gases in this solvent.
- Typical physical solvents are methanol, N-methylpyrrolidone, and dialkyl (dimethyl) ethers of polyethylene glycol.
- amines preferably tertiary amines. These amines form salts in contact with acid gases which can be decomposed by heating and / or purified ("stripping") with steam.
- the document FR-A1-2 328 657 relates to a process for enriching in 3 ⁇ 4S acid gases containing 3 ⁇ 4S, CO 2 and a hydrocarbon proportion of less than 5% in which the gases are washed at counteracting with an aqueous solution of Methyldiethanolamine (MDEA).
- MDEA Methyldiethanolamine
- the document WO-A1-87 / 01961 describes a method and a device for the selective elimination of the 3 ⁇ 4S of a gas containing it in which the gas to be treated is brought into contact, in an absorption zone, with a absorbS selective absorbing liquid and regenerable by heating.
- the absorbent liquid may be based on one or more physical-acting solvents or consist of a chemical-acting solvent formed, for example, by an aqueous solution of an alkanolamine such as methyldiethanolamine (MDEA) or triethanolamine (TEA).
- the absorbing liquid may also be selected from the mixtures of the two types of solvent with chemical action and physical action mentioned above. It is specified that an aqueous solution of an alkanolamine such as methyldiethanolamine or triethanolamine is especially suitable as a selective absorbent liquid for H 2 S.
- an alkanolamine such as methyldiethanolamine or triethanolamine is especially suitable as a selective absorbent liquid for H 2 S.
- US-A-4, 519, 991 relates to the enrichment of a gas in 3 ⁇ 4S by selective absorption with an aqueous solution of methyl ⁇ diethanolamine.
- US-A-4, 545, 965 relates to the selective separation of 3 ⁇ 4S from gaseous mixtures which also contain CO 2 by chemical absorption with an anhydrous solution of a tertiary amine such as methyldiethanolamine, and an auxiliary organic solvent such as sulfolane.
- Mercaptan removal rates are often less than 20% with these technologies.
- sulfur-containing compounds such as mercaptans which are not removed during the Deacidification can end up in the gas distribution network, and impose additional steps for their disposal in the dehydration, or degassing-separation facilities.
- the inventors have demonstrated that, surprisingly, the addition of a C 2 -C 4 thioalkanol, such as ThioDiGlycol (TDG), to an absorbent solution, an absorption mixture, comprising an amine and water, allowed to greatly improve the selectivity of said absorbent solution for removal of hydrogen sulfide from carbon dioxide in a gaseous mixture containing hydrogen sulfide and carbon dioxide.
- TDG ThioDiGlycol
- MDEA MetalDiEthanolAmine
- DEA (DiEthanolAmine) -TDG presents, because of the presence of TDG, a selectivity towards the 3 ⁇ 4S much higher than that of a water-DEA absorbing solution without TDG.
- Thioalkanol such as TDG, proves to be a determining element in the formulation of the absorbent solution which makes it possible to optimize the selective removal of H 2 S with respect to CO 2 .
- the absorbent solution comprising an amine, water and a thioalkanol
- the water-MDEA-TDG absorbing solution also surprisingly has the presence of the thioalkanol, such as TDG, compared to a similar absorbent solution not comprising thioalkanol, such as the water-absorbing solution MDEA, the advantageous property of improving the elimination of other sulfur compounds such as mercaptans possibly contained in the gaseous mixture.
- the invention makes it possible to reduce capital expenditure ("CAPEX”) and operating expenses.
- OPEX organic compound
- the invention thus relates to a process for selectively removing hydrogen sulfide 3 ⁇ 4S from carbon dioxide CO2 in a gaseous mixture containing at least hydrogen sulfide 3 ⁇ 4S and carbon dioxide CO2, comprising a step of contacting said gaseous mixture with an absorbent solution comprising, preferably consisting of, at least one amine, water, and at least one thioalkanol C2 -C 4.
- the gaseous mixture to be treated may be any gaseous mixture containing 3 ⁇ 4S and CO2 carbon dioxide.
- this gaseous mixture may contain, in addition to 3 ⁇ 4S and CO2, at least one other sulfur compound (different from 3 ⁇ 4S) preferably chosen from mercaptans and carbonyl sulphide COS.
- the mercaptans which have the formula R-SH include methyl mercaptan and ethyl mercaptan, but of other mercaptans, and cells of the type C 3 SH to CeSH, may be present, generally at lower concentrations than methylmercaptan and
- the hydrogen sulfide content 3 ⁇ 4S of the gaseous mixture to be treated is generally between 30 ppm by volume and 40% by volume, and after the contacting step this content can be lowered to 1 ppm by volume.
- the CO 2 content of the gaseous mixture to be treated is generally between 0.5% by volume and 80% by volume, preferably between 1% by volume and 50% by volume, and even more preferably between 1%. in volume and 15% in volume.
- the gaseous mixture to be treated may contain at least one mercaptan at a content generally less than 1000 ppm by volume, preferably between 5 ppm by volume and 500 ppm by volume, and the method according to the invention makes it possible to eliminate a proportion of mercaptans 2 to 3 times higher than that observed with the processes using a solution without thioalkanol.
- the gaseous mixture to be treated may contain COS at a content generally less than 200 ppm by volume, preferably between 1 ppm and 100 ppm by volume.
- Gaseous mixtures which contain hydrogen sulphide, carbon dioxide, and possibly at least one other sulfur compound are, for example, natural gas, synthesis gas, cracking gas, coke oven gas, gasification of coal, landfill gas, biogas, and flue gases.
- the gaseous mixture may be a hydrogenated gaseous mixture, that is, it contains as the major component hydrogen, or hydrogen and carbon dioxide or hydrogen and carbon monoxide. carbon.
- the gaseous mixture is a gaseous hydrocarbon mixture, that is to say that it contains as majority component one or more hydrocarbons.
- hydrocarbons are, for example, saturated hydrocarbons such as C1 to C4 alkanes such as methane, ethane, propane and butane, unsaturated hydrocarbons such as ethylene or propylene, or aromatic hydrocarbons such as toluene or xylene.
- Said gaseous hydrocarbon mixture can be chosen from natural gases, tail gases obtained at the output of sulfur chains (CLAUS plant), and gases obtained in the gas processing plants ("gas plant") of a refinery.
- Natural gases have very variable pressures, which can range, for example, from 10 to 100 bar, and temperatures that can range from 20 ° C. to 60 ° C.
- the CO 2 and 3 ⁇ 4S contents of natural gases are also very variable. They can be up to 15% by volume for each of these two compounds and can even be up to 40% for 3 ⁇ 4S.
- the tail gases obtained at the outlet of the sulfur chains, or the feed gases of the unixS enrichment units situated upstream of the CLAUS processes, have a pressure that is generally very low, for example less than 3 bar, most often less than 2 bar, and the temperatures of these gases are generally between 40 ° C and 70 ° C.
- the tenS contents of these tail gases are generally less than 5% by volume, and often less than 2% by volume.
- the CO 2 contents of these tail gases are variable and can reach 80% by volume.
- selectivity S of the absorbent solution vis-à-vis the 3 ⁇ 4S, relative to CO 2 given by the next formula is greater than 1:
- - c (3 ⁇ 4S) mixture after treatment is the volume concentration in 3 ⁇ 4S in the gaseous mixture after treatment with the absorbent solution
- - c (CO2) mixture is the volume concentration of CO2 in the gaseous mixture before treatment with the absorbent solution
- the selectivity S of the absorbent solution containing a thioalkanol is greater than 5% to 50%, for example greater than 8% to 15%, with the selectivity S of the same solution without thioalkanol.
- the C2 to C4 thioalkanol has the formula: RS- (C2-C4 alkylene) -OH, where R is any group, for example an alkyl group (generally C1 to C6) or an alkanol group (generally C 1 to C e), or a thiol group, or an alkylthioalkanol group (generally C 1 to C e).
- the thioalkanol C 2 -C 4 is a dimeric molecule.
- thioalkanol C2 -C 4 is ethylene dithioethanol of formula (HO-CH 2 -CH 2) -S- (CH 2 -CH 2) -S- (CH 2 - CH2-OH).
- the preferred thioalkanol is thiodiethylene glycol or thiodiglycol (TDG) which is the compound of formula S (CH 2 -CH 2 -OH) 2 .
- C 2 -C 4 thioalkanols can still be used according to the invention, especially methylthioethanol. It is also possible to use a mixture of several thioalkanols. Any amine can be used in the absorbent solution, especially the amines used in the known processes of selective removal of 3 ⁇ 4S.
- the amine may be, for example, a primary, secondary or tertiary amine, aliphatic, cyclic, or aromatic amine.
- the amine used should generally be soluble in water at the concentrations used in the absorbent solution.
- primary amine generally means a compound comprising at least one primary amine function.
- the term “secondary amine” generally means a compound comprising at least one secondary amine function.
- tertiary amine generally means a compound comprising at least one tertiary amine function and preferably comprising only tertiary amine functions.
- These primary, secondary or tertiary amines may be chosen from aliphatic amines, cyclic amines, or the like.
- the amine is chosen from alkanolamines (aminoalcohols).
- alkanolamines can be primary, secondary or tertiary.
- the alkanolamines or aminoalcohols are amines comprising at least one hydroxyalkyl group (comprising, for example, from 1 to 10 carbon atoms) bonded to the nitrogen atom.
- Tertiary alkanolamines may be trialkanolamines, alkyldialkanolamines or dialkylalkanolamines.
- the secondary alkanolamines may be dialkanolamines, or alkylalkanol amines, and the primary alkanolamines are monoalkanolamines.
- the alkyl groups and the hydroxyalkyl groups of the alkanolamines can be linear or branched and generally comprise from 1 to 10 carbon atoms, preferably the alkyl groups comprise from 1 to 4 carbon atoms, and the hydroxyalkyl groups comprise from 2 to 4 carbon atoms. carbon.
- alkanolamines examples include 2-aminoethanol (monoethanolamine, MEA), N, N-bis (2-hydroxethyl) amine (diethanolamine, DEA), N, N, -bis (2-hydroxypropyl) amine (diisopropanolamine, DIPA), tris (2-hydroxyethyl) amine (triethanolamine, TEA), tributanolamine, bis (2-hydroxyethyl) methylamine (methyldiethanolamine, MDEA), 2-diethylaminoethanol (diethylethanolamine, DEEA), 2-dimethylaminoethanol ( dimethyletanolamine, DMEA), 3-dimethylamino-1-propanol (N, -dimethylpropanolamine), 3-diethylamino-1-propanol, 2-diisopropylaminoethanol (DIEA), N, -bis (2-hydroxypropyl) methylamine
- tertiary amines and especially tertiary alkanolamines are given in US-A1-2008 / 0025893 to the description of which we can refer.
- Methyldiethanolamine N, N-
- DMEA Dimethylethanolamine
- DIEA Diisopropylaminoethanol
- TMPDA ⁇ , ⁇ , ⁇ ', ⁇ '-Tetramethylpropanediamine
- TEPDA ⁇ , ⁇ , ⁇ ', ⁇ '-tetraethylpropanediamine
- Miax dimethylamino-2-dimethylaminoethoxyethane
- DMDEEDA dimethylamino-2-dimethylaminoethoxyethane
- tertiary alkanolamines which can be used in the process according to the invention are also given in US-A1-2010 / 0288125, to the description of which reference may be made.
- tris (2-hydroxyethyl) amine triethanolamine, TEA
- tris (2-hydroxypropyl) amine triisopropanol
- tributylethanolamine TEA
- bis (2-hydroxyethyl) methylamine methyldiethanolamine, MDEA
- 2-diethylaminoethanol diethylethanolamine, DEEA
- 2-dimethylaminoethanol dimethylethanolamine DMEA
- 3-dimethylamino-1-propanol 3-diethylamino-1-propanol
- 2-diisopropylaminoethanol DIEA
- N -bis (2-hydroxypropyl) methylamine
- the amine may also be selected from aminoethers.
- aminoethers examples include 2-2- (Aminoethoxy) ethanol (AEE), 2- (2-t-butylaminoethoxy) ethanol (EETB), and 3-methoxypropyldimethylamine.
- the amine may also be chosen from saturated 3, 5, 6, or 7-membered heterocycles comprising at least one NH group contained in the ring.
- the ring may optionally further comprise one or two other heteroatoms in the ring selected from nitrogen and oxygen, and may be optionally substituted with one or more substituents selected from alkyl radicals comprising from 1 to 6 carbon atoms. like the ethyl or methyl radicals, aminoalkyl radicals comprising 1 to 6 carbon atoms, and hydroxyalkyl radicals comprising 1 to 6 carbon atoms.
- heterocycles examples include piperazine, 2-methylpiperazine, N-methylpiperazine, N-ethylpiperazine, N-aminoethylpiperazine (AEPZ), aminopropylpiperazine, N-hydroxyethylpiperazine (HEP), homopiperazine, bis ( hydroxyethyl) piperazine, piperidine, aminoethylpiperidine (AEPD), aminopropylpiperidine, furfurylamine (FA) and morpholine (MO).
- the amine used according to the invention may finally be chosen from polyamines such as alkylene polyamines, tertiary bis (diamines) and polyalkylene polyamines.
- alkylene diamines mention may be made of hexamethylenediamine, 1,4-diaminobutane, 1,3-diaminopropane, 2,2-dimethyl-1,3-diaminopropane, 3-methylaminopropylamine and N (2-hydroxyethyl).
- ethylenediamine 3 (dimethylaminopropylamine) (DMAPA), 3
- DTPA dipropylenetriamine
- TETA triethylenetetramine
- TEPA tetraethylene pentamine
- HMDA tris (3-aminopropyl) amine
- 2-aminoethyl) amine tris (3-aminopropyl) amine
- the absorbent solution comprises only amines comprising only tertiary amine groups and / or sterically hindered amine groups.
- Preferred amines comprising only tertiary amine groups are tris (2-hydroxyethyl) amine (triethanolamine, TEA), tris (2-hydroxypropyl) amine (triisopropanol), tributanolamine, bis (2-hydroxyethyl) methylamine
- Preferred amines comprising only sterically hindered amine groups are 2-amino-2-methyl-1-propanol (AMP) and 1-amino-2-methylpropan-2-ol.
- the absorbent solution preferably comprises:
- absorbent solutions which include MDEA as amine, TDG as thioalkanol, and water in the aforementioned proportions are preferred.
- a most preferred absorbent solution is the absorbent solution consisting of water, MDEA, and TDG in the respective proportions of 38%, 45%, and 17% by weight.
- the contacting step is carried out at a temperature generally of 40 ° C to 100 ° C, preferably of 50 ° C to 90 ° C, and at a pressure of 1 to 150 bar, preferably of 10 to 70 bar.
- the selective elimination process as described above further comprises, after the contacting step, a regeneration step of the absorbent solution.
- said step of regenerating the absorbent solution is carried out at a pressure of 0 to 20 bar, preferably of 1 to 3.5 bar, more preferably of 1 to 2 bar, and at a temperature of 100 ° C. to 140 bar. ° C.
- the invention can be implemented in any conventional absorption and regeneration installation using chemical absorbent solutions.
- Any gas-liquid contact apparatus may be used to perform the contacting, absorption step.
- any type of column can be used as an absorption column. It may be in particular a perforated plate column, a valve column or a column with bells.
- Packed, loose or structured columns can also be used.
- absorption column or “column” are used for simplification to designate the gas-liquid contact apparatus, but it is clearly understood that any gas-liquid contact apparatus may be used for perform the absorption step.
- the contacting and absorption step can be carried out, for example in an absorption column, at a temperature generally of from 40 ° C. to 100 ° C., preferably from 50 ° C. to 90 ° C. and a pressure of 1 to 150 bar, preferably 10 to 70 bar.
- the absorption is carried out by contacting the gaseous mixture with the absorbing solution at a gaseous mixture flow rate generally from 0.23 ⁇ 10 6 Nm 3 / day to 56 ⁇ 10 6 Nm 3 / day and at a flow rate of absorbing solution generally from 800 to 50000 m 3 / day.
- the regeneration step of the absorbent solution is carried out conventionally by heating and separating RSH mercaptans and acid gases, including 3 ⁇ 4S, in a regeneration column.
- This step of regeneration of the absorbent solution is generally carried out under the conditions of temperature and pressure already indicated above.
- the amine solution loaded with acid gases such as 3 ⁇ 4S, CO 2 and mercaptans RSH-rich amine-dite from the bottom of the absorption column is sent into an intermediate pressure flash drum.
- gases resulting from the expansion of the rich amine can be used as "fuel-gas" fuel gas, however, according to the invention, these gases heavily loaded with 3 ⁇ 4S are preferably treated, or possibly directly sent to a production unit.
- the gas sent to the Claus installation is very rich in 3 ⁇ 4S and the size of this installation and the related costs can be greatly reduced.
- the rich amine is then reheated in an amine / amine exchanger by the hot amine of the regenerator bottom, and optionally partially vaporized and then recycled to feed the regeneration column.
- a reboiler generates steam that flows upstream into the column, resulting in acidic constituents such as H 2 S and CO 2 and RSH mercaptans. This desorption is favored by the low pressure and the high temperature prevailing in the regenerator.
- the acid gases are cooled in a condenser.
- the condensed water is separated from the acid gas in a reflux flask and returned either to the top of the regeneration column or directly to the lean amine solution tank.
- the regenerated amine which is therefore also called poor amine is then recycled to the absorption step.
- a semi-regenerated mode of operation can also be envisaged.
- a fraction of the partially regenerated solvent taken from the intermediate expansion tanks or at an intermediate level of the regeneration column can be sent to an intermediate level of the absorption section.
- the gaseous mixture treated such as natural gas
- the invention also relates to the use of an absorbent solution comprising, preferably consisting of, at least one amine, water, and at least one C 2 -C 4 thioalkanol for the selective removal of hydrogen sulfide relative to carbon dioxide in a gaseous mixture containing at least hydrogen sulfide and carbon dioxide.
- the invention finally relates to the use of at least one C 2 to C 4 thioalkanol as an additive to an absorbent solution comprising at least one amine, and water, to increase the selectivity of said absorbent solution for treating removal of hydrogen sulfide from carbon dioxide in a gaseous mixture containing at least hydrogen sulfide and carbon dioxide.
- the gaseous mixture contains, in addition to 3 ⁇ 4S and CO 2 , at least one other sulfur compound (other than 3 ⁇ 4S) preferably chosen from mercaptans and COS, and the use of at least one thioalkanol in As an additive to the absorbent solution comprising at least one amine and water, it also makes it possible to increase the elimination of said sulfur compound.
- Figure 1 is a graph which shows the results of comparative absorption tests of CO 2 contained in a gaseous mixture, by two absorbent solutions, made in a pilot plant comprising an absorption column comprising 11 trays.
- the plate number of the absorption column is plotted, and the CO 2 elimination rate is plotted on the ordinate ( ⁇ ⁇ % relative to the initial CO 2 content in the gaseous mixture).
- Figure 2 is a graph which shows the results of comparative absorption tests of the 3 ⁇ 4S contained in a gaseous mixture, by two absorbent solutions, made in a pilot plant comprising an absorption column comprising 11 trays.
- FIG. 3 is a graph which shows the results of comparative absorption tests of CO 2 contained in a gas mixture by two absorbent solutions, made in a pilot plant comprising an absorption column having 11 trays.
- the plate number of the absorption column is plotted, and the CO 2 removal rate ( ⁇ % relative to the initial content of CO 2 in the gaseous mixture) is plotted on the ordinate.
- Figure 4 is a graph which shows the results of comparative absorption tests of the 3 ⁇ 4S contained in a gaseous mixture, by two absorbent solutions, made in a pilot plant comprising an absorption column comprising 11 trays.
- the plate number of the absorption column is plotted, and the CO 2 removal rate ( ⁇ % relative to the initial content of CO 2 in the gaseous mixture) is plotted on the ordinate.
- FIG. 5 is a graph which shows the results of absorption tests of gaseous CO 2 by absorbent solutions, including three absorbent solutions used according to the invention, carried out in the laboratory, in a reactor that makes it possible to control the contact area between the gas and the absorbent solution.
- the absorption tests were carried out at a temperature of 60 ° C. with solutions comprising water, DEA in equal amounts by weight and TDG in amounts of 0%, 10%, 20% and 30%, respectively. % in weight.
- FIG. 6 is a graph which shows the results of absorption tests for gaseous CO 2 by absorbent solutions of which three absorbent solutions used according to the invention, carried out in the laboratory, in a reactor to control the contact area between the gas and the absorbent solution.
- the absorption tests were carried out at a temperature of 60 ° C. with solutions comprising water, MDEA in equal amounts by weight, and TDG in amounts of 0%, 10%, 20% and 30% by weight.
- the pilot plant for washing gas treatment implemented in this example makes it possible to treat from 50 to 1500 Nm 3 / h of gas under a pressure of 10 to 40 bar with a solvent flow rate of 100 to 3500 L / h and she understands : • an absorption loop (maximum 40 bar), consisting of a column containing 11 trays each of a diameter of 20 cm, and a system of compressors, ejectors and exchangers ensuring the flow of gas.
- a regeneration section (maximum 5 bar) composed of a packed column with a diameter of 30 cm, a preheater, a steam reboiler, a return pump, a water head condenser , a head condenser with a cold group, and a decompression of the acid gas.
- a storage section consisting of a water cooler, a storage tank and a recovery pump.
- the gas flow rate is set at 283 Nm 3 / h.
- the gas consists of an inert gas, namely nitrogen for these tests.
- the gas to be treated contains from 1.5 to 1.6 mol% of H 2 S, and from 1.6 to 1.7 mol% of CO 2 for the tests at 18 bar; and 1.5 to 1.6 mol% H 2 S, and 1.3 to 1.5 mol% CO 2 for the 40 bar tests.
- the gas is contacted with the solvent in the absorber.
- the solvent flow rate is set at 295 L / h for the tests.
- the tests were carried out with an absorbent solution called reference water-MDEA 55-45 ⁇ 6 by mass and an absorbent solution used according to the invention water-MDEA-TDG 38-45-17% by mass.
- the concentration of 3 ⁇ 4S or CO 2 is measured by gas chromatography assay at the different trays along the column.
- the reactor used is a closed reactor.
- the absorbent solution is first introduced into the reactor, then a given amount of carbon dioxide is in turn introduced into the reactor.
- the pressure drop resulting from the absorption phenomenon of the gas in the absorption solution is then measured.
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Organic Chemistry (AREA)
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2874361A CA2874361C (fr) | 2012-05-25 | 2013-05-23 | Procede d'elimination selective du sulfure d'hydrogene de melanges gazeux et utilisation d'un thioalcanol pour l'elimination selective du sulfure d'hydrogene |
US14/402,515 US20150147254A1 (en) | 2012-05-25 | 2013-05-23 | Process for selectively removing hydrogen sulphide from gaseous mixtures and use of a thioalkanol for selectively removing hydrogen sulphide |
EA201491941A EA201491941A1 (ru) | 2012-05-25 | 2013-05-23 | Способ селективного удаления сульфида водорода из газовых смесей и применение тиоалканола для селективного удаления сульфида водорода |
BR112014028971-9A BR112014028971A2 (pt) | 2012-05-25 | 2013-05-23 | processo de remoção seletiva de sulfeto de hidrogênio de misturas gasosas e uso de um tioalcanol para remoção seletiva de sulfeto de hidrogênio |
CN201380027182.5A CN104334253A (zh) | 2012-05-25 | 2013-05-23 | 从气体混合物中选择性去除硫化氢的方法以及硫代烷醇用于选择性去除硫化氢的用途 |
NO20141522A NO20141522A1 (no) | 2012-05-25 | 2014-12-17 | Fremgangsmåte for selektiv fjerning av hydrogensulfid fra gassblandinger samt anvendelse av en tioalkanol for selektivt å fjerne hydrogensulfid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR1254842 | 2012-05-25 | ||
FR1254842A FR2990880B1 (fr) | 2012-05-25 | 2012-05-25 | Procede d'elimination selective du sulfure d'hydrogene de melanges gazeux et utilisation d'un thioalcanol pour l'elimination selective du sulfure d'hydrogene. |
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PCT/EP2013/060578 WO2013174902A1 (fr) | 2012-05-25 | 2013-05-23 | Procede d'elimination selective du sulfure d'hydrogene de melanges gazeux et utilisation d'un thioalcanol pour l'elimination selective du sulfure d'hydrogene |
Country Status (9)
Country | Link |
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US (2) | US20150147254A1 (fr) |
CN (1) | CN104334253A (fr) |
BR (1) | BR112014028971A2 (fr) |
CA (1) | CA2874361C (fr) |
EA (1) | EA201491941A1 (fr) |
FR (1) | FR2990880B1 (fr) |
MY (1) | MY175564A (fr) |
NO (1) | NO20141522A1 (fr) |
WO (1) | WO2013174902A1 (fr) |
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CN110385022A (zh) * | 2018-04-19 | 2019-10-29 | 中国石油化工股份有限公司 | 脱硫剂及其应用和轻烃脱硫加工的方法 |
WO2022129975A1 (fr) | 2020-12-17 | 2022-06-23 | Totalenergies Onetech | Procédé pour l'élimination sélective du sulfure d'hydrogène à partir d'un courant de gaz |
WO2022129977A1 (fr) | 2020-12-17 | 2022-06-23 | Totalenergies Onetech | Procédé de récupération de dioxyde de carbone de haute pureté à partir d'un mélange gazeux |
WO2022129974A1 (fr) | 2020-12-17 | 2022-06-23 | Totalenergies Onetech | Milieu d'élimination sélective de sulfure d'hydrogène à partir d'un courant gazeux |
WO2024180358A1 (fr) | 2023-02-27 | 2024-09-06 | Totalenergies Onetech | Procédé de séparation sélective de sulfure d'hydrogène d'un mélange gazeux |
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CN105531013A (zh) * | 2013-07-29 | 2016-04-27 | 埃克森美孚研究工程公司 | 从天然气分离硫化氢 |
DE102014118345A1 (de) * | 2014-12-10 | 2016-06-16 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Verfahren und Anlage zur Reinigung von Rohsynthesegas |
WO2016116815A1 (fr) * | 2015-01-22 | 2016-07-28 | Carbon Clean Solutions Limited | Solvant et procédé permettant d'éliminer des gaz acides d'un mélange gazeux |
EP3250311A4 (fr) | 2015-01-28 | 2019-02-13 | Fluor Technologies Corporation | Procédés et systèmes d'amélioration du rendement énergétique de la capture du dioxyde de carbone |
US11241652B2 (en) * | 2017-05-15 | 2022-02-08 | Basf Se (Reitstötter, Kinzebach & Partner) | Absorbent and process for selectively removing hydrogen sulfide |
US10376829B2 (en) | 2017-06-13 | 2019-08-13 | Fluor Technologies Corporation | Methods and systems for improving the energy efficiency of carbon dioxide capture |
CN109529541B (zh) * | 2017-09-21 | 2022-07-22 | 株式会社东芝 | 二氧化碳吸收剂及二氧化碳分离回收装置 |
CN110052119B (zh) * | 2019-03-26 | 2021-12-07 | 昆明理工大学 | 有机溶剂吸收提浓工业酸性气中硫化氢及资源利用的方法 |
EP4028148B1 (fr) | 2019-09-10 | 2023-11-15 | Basf Se | Procédé d'élimination de gaz acides d'un flux de fluide |
CN111013368B (zh) * | 2019-11-25 | 2021-12-21 | 北京化工大学 | 同时吸收多种酸性气体的反应系统、吸收液及方法 |
WO2022010874A1 (fr) * | 2020-07-07 | 2022-01-13 | Exxonmobil Research And Engineering Company | Procédés de lavage de gaz acide comprenant une séparation de phase amine pour la capture de sulfure d'hydrogène |
CN113318586B (zh) * | 2021-06-09 | 2022-07-19 | 华东理工大学 | 一种胺类化合物在提高有机硫溶解和吸收脱除中的应用 |
CN114768477B (zh) * | 2022-03-18 | 2023-11-17 | 中国科学技术大学 | 一种二氧化碳捕集方法 |
CN114797425A (zh) * | 2022-04-18 | 2022-07-29 | 成都中科绿生环境科技有限公司 | 一种可针对性去除h2s与硫醇的试剂及其制备方法和应用 |
CN116139657A (zh) * | 2023-03-01 | 2023-05-23 | 昆明理工大学 | 一种用于捕集二氧化碳的胺类非水吸收剂及其使用方法 |
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- 2013-05-23 EA EA201491941A patent/EA201491941A1/ru unknown
- 2013-05-23 WO PCT/EP2013/060578 patent/WO2013174902A1/fr active Application Filing
- 2013-05-23 CA CA2874361A patent/CA2874361C/fr active Active
- 2013-05-23 BR BR112014028971-9A patent/BR112014028971A2/pt not_active Application Discontinuation
- 2013-05-23 MY MYPI2014003217A patent/MY175564A/en unknown
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2014
- 2014-12-17 NO NO20141522A patent/NO20141522A1/no not_active Application Discontinuation
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WO2022129975A1 (fr) | 2020-12-17 | 2022-06-23 | Totalenergies Onetech | Procédé pour l'élimination sélective du sulfure d'hydrogène à partir d'un courant de gaz |
WO2022129977A1 (fr) | 2020-12-17 | 2022-06-23 | Totalenergies Onetech | Procédé de récupération de dioxyde de carbone de haute pureté à partir d'un mélange gazeux |
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Also Published As
Publication number | Publication date |
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US20170320008A1 (en) | 2017-11-09 |
NO20141522A1 (no) | 2014-12-17 |
FR2990880B1 (fr) | 2017-04-28 |
CN104334253A (zh) | 2015-02-04 |
US20150147254A1 (en) | 2015-05-28 |
CA2874361A1 (fr) | 2013-11-28 |
EA201491941A1 (ru) | 2015-03-31 |
BR112014028971A2 (pt) | 2020-11-03 |
FR2990880A1 (fr) | 2013-11-29 |
CA2874361C (fr) | 2021-03-30 |
MY175564A (en) | 2020-07-01 |
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