WO2013174907A1 - Procede de purification de melanges gazeux contenant des gaz acides - Google Patents
Procede de purification de melanges gazeux contenant des gaz acides Download PDFInfo
- Publication number
- WO2013174907A1 WO2013174907A1 PCT/EP2013/060586 EP2013060586W WO2013174907A1 WO 2013174907 A1 WO2013174907 A1 WO 2013174907A1 EP 2013060586 W EP2013060586 W EP 2013060586W WO 2013174907 A1 WO2013174907 A1 WO 2013174907A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- absorbent solution
- activator
- chosen
- tertiary amine
- ppm
- Prior art date
Links
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- 238000000034 method Methods 0.000 title claims abstract description 85
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 239000002253 acid Substances 0.000 title claims abstract description 35
- 230000002745 absorbent Effects 0.000 claims abstract description 81
- 239000002250 absorbent Substances 0.000 claims abstract description 81
- 239000012190 activator Substances 0.000 claims abstract description 40
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 31
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- 150000003141 primary amines Chemical class 0.000 claims abstract description 14
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 14
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- 238000011282 treatment Methods 0.000 claims description 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 20
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- 229950006389 thiodiglycol Drugs 0.000 claims description 19
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 16
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 26
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- 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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- 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
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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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- 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
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- 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
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- C10L3/102—Removal of contaminants of acid contaminants
- C10L3/103—Sulfur containing contaminants
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- 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
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- C10L3/104—Carbon dioxide
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D2252/202—Alcohols or their derivatives
- B01D2252/2023—Glycols, diols or their derivatives
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- B01D2252/204—Amines
- B01D2252/20436—Cyclic amines
- B01D2252/20447—Cyclic amines containing a piperazine-ring
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- B01D2252/20489—Alkanolamines with two or more hydroxyl groups
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- B01D2252/20—Organic absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D—SEPARATION
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- 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
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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- 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
- C10L2290/54—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 a method for purifying gaseous mixtures.
- the present invention is applicable to the treatment of liquid hydrocarbon mixtures containing acid compounds and other sulfur compounds such as mercaptans and COS.
- the present invention further relates to an absorbent solution for carrying out this method.
- the invention finds particular application in the oil and gas industry.
- the invention is particularly applicable to the elimination of acid gases in natural gases. Indeed, acidic natural gases account for about 40% of the world's remaining gas reserves, and specifications for the sulfur content of these gases are becoming more severe.
- gaseous mixtures and in particular of gaseous hydrocarbon mixtures such as natural gas, which mainly comprises methane, or of synthesis gas, 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 sulphide (H 2 S) such as, for example, carbonyl sulphide (COS) and mercaptans (R-SH, where R is an alkyl group); water, and some hydrocarbons.
- Carbon dioxide and hydrogen sulphide may account for a significant portion of the gaseous mixture from a natural gas deposit, typically 3% to 70% by volume, while COS is present in smaller amounts, typically from 1 to 100 ppm by volume, and that the mercaptans are present at a content generally below 1000 ppm by volume, for example at a content between 5 ppm by volume and 500 ppm by volume.
- Contaminants that must be removed include mercaptans.
- the total amount of mercaptans in a gas mixture from a natural gas production site may be several hundred ppm by volume.
- the two main mercaptans concerned are methyl mercaptan and ethyl mercaptan, but other mercaptans, and in particular the C 3 SH to CeSH molecules, may be present, generally at a lower concentration.
- LPG liquefied petroleum gas
- the specifications for the acid gas content in the treated gas (resulting from the treatment) are specific to each of the products under consideration. Thus, levels of a few ppm are imposed for H 2 S or other sulfur compounds, while the specifications for CO 2 are between a few ppm if a liquefaction stage for producing liquefied natural gas is provided for. downstream of the purification process, and a few%, in general 2%.
- a similar problem is encountered for the deacidification of liquid hydrocarbon mixtures, in particular liquid hydrocarbon cuts, obtained in the degassing stages of natural gas, or during the fractionation of crudes in applications related to the refining of petroleum or crude oil. other mixtures of liquid hydrocarbons.
- carbon dioxide C0 2 and hydrogen sulfide 3 ⁇ 4S are generally removed during a a step employing a water-alkanolamine absorbent solution, while the other sulfur-containing compounds, such as mercaptans or COS, are removed during steps using dedicated processes such as absorption on a molecular sieve or washing with soda.
- primary or secondary alkanolamines have been used for the treatment of gaseous or liquid hydrocarbon streams charged with acid gases.
- alkanolamines particular mention may be made of: MonoEthanolAmine (MEA, 2-aminoethanol), Diethanolamine (DEA, N, N-bis (2-hydroxyethyl) amino), DilsoPropanolAmine (DIPA, N, N-bis (2- hydroxypropyl) amine) and 2-aminoethoxyethanol (AEE).
- MEA MonoEthanolAmine
- DEA Diethanolamine
- DIPA DilsoPropanolAmine
- AEE 2-aminoethoxyethanol
- MDEA MethylDiethanolAmine
- Such optimized absorbent solutions may in particular comprise a tertiary amine and an activator. Examples of these absorbent solutions are given in the following documents:
- Document US-A1-2008 / Q025893 relates to a method for removing CO 2 from a gaseous stream in which said gaseous stream is brought into contact with a liquid absorbing agent chosen from an aqueous solution of an amine compound with at least one minus two tertiary amino groups in their molecule and an activator selected from primary and secondary amines; or an aqueous solution of a tertiary aliphatic amine and an activator selected from 3-methylaminopropylamine, piperazine, 2-methylpiperazine, N-methylpiperazine (NMP),
- a liquid absorbing agent chosen from an aqueous solution of an amine compound with at least one minus two tertiary amino groups in their molecule and an activator selected from primary and secondary amines; or an aqueous solution of a tertiary aliphatic amine and an activator selected from 3-methylaminopropylamine, piperazine, 2-methylpiperazine, N-methylpiperaz
- aqueous absorbent comprising at least one tertiary alkanolamine chosen especially from methyldiethanolamine (MDEA), triethanolamine (TEA), ethyldiethanolamine or diethanolamine (DEA); an amine selected from hydroxyethylpiperazine (HEP) or a mixture thereof with bis (hydroxyethylpiperazine); and piperazine.
- MDEA methyldiethanolamine
- TEA triethanolamine
- DEA ethyldiethanolamine or diethanolamine
- HEP hydroxyethylpiperazine
- piperazine piperazine
- US-B1-6,852,144 relates to a process for selectively removing COS with respect to CO 2 in a stream of a hydrocarbon fluid which contains CO 2 and COS in which the hydrocarbon fluid is contacted with a washing liquid consisting of an aqueous amine solution containing a aliphatic alkanolamine having 2 to 12 carbon atoms, preferably a tertiary alkanolamine such as methyldiethanolamine (MDEA) or triethanolamine (TEA); and an activator selected from piperazine, methylpiperazine, and morpholine (MO).
- MDEA methyldiethanolamine
- TAA triethanolamine
- US-A-5 f 277 f 885 and US-A-5, 348, 714 relate to a CO 2 absorption process in a gas wherein said gas is brought into contact with an absorbent liquid which is generally in the form of an aqueous solution of one or more alkanolamines such as MDEA and an activator which improves the absorption of CO 2 by said alkanolamines.
- an absorbent liquid which is generally in the form of an aqueous solution of one or more alkanolamines such as MDEA and an activator which improves the absorption of CO 2 by said alkanolamines.
- the activator may especially be chosen from polyamines such as dipropylenetriamine (DPTA), diethylenetriamine (DETA), triethylenetetramine (TETA) and tetraethylenepentamine (TEPA); Aminoethylethanolamine (AEEA), hexamethylenediamine (HMDA), dimethylaminopropylamine (DMAP and diaminocyclohexane (DACH).
- polyamines such as dipropylenetriamine (DPTA), diethylenetriamine (DETA), triethylenetetramine (TETA) and tetraethylenepentamine (TEPA); Aminoethylethanolamine (AEEA), hexamethylenediamine (HMDA), dimethylaminopropylamine (DMAP and diaminocyclohexane (DACH).
- DPTA dipropylenetriamine
- DETA diethylenetriamine
- TETA triethylenetetramine
- TEPA tetraethylenepentamine
- ethoxypropylamine (MOPA), ethoxypropylamine, aminoethylpiperazine (AEPZ), aminopropylpiperazine, aminoethylpiperidine (AEPD), aminopropylpiperidine, furfuramine (FA), and the like.
- ethylmonoethanolamine (EMEA).
- another solution consists therefore of using a hybrid solvent, composed of water, of alkanolamine, and of an organic compound making it possible to solubilize in the solvent the sulfur compounds, such as than the mercaptans.
- the objective of the processes that use such hybrid solvents is to simultaneously remove CO 2 , 3 ⁇ 4S, and other sulfur compounds, such as mercaptans and COS.
- suifolane leads to a significant coabsorption of hydrocarbons, which causes many problems both with regard to the operation of downstream sulfur production facilities, as well as with regard to the quality of the products derived from these products. installations.
- methanol as cosolvent leads to significant losses of alcohol.
- the preferred alkanolamine is diethanolamine (DEJA), and the preferred thiodiglycol is thiodiglycol (TDG). .
- this method can not easily be adapted depending on the composition of the treated filler and / or the specifications to be complied with as regards the contents of each of the compounds to be eliminated.
- the object of the present invention is to provide a process for purifying a gaseous mixture containing acid gases that meets these needs, among others.
- the object of the present invention is still to provide such a method which does not have the disadvantages, defects, limitations and disadvantages of the processes of the prior art, and which provides a solution to the problems of the processes of the prior art.
- a process for purifying a gaseous mixture containing at least one acidic gas selected from hydrogen sulfide 3 ⁇ 4S and carbon dioxide CO 2 comprising a step of contacting said gaseous mixture with an absorbent solution comprising, preferably consisting of:
- the activator is preferably selected from primary amines and secondary amines, more preferably from primary alkanolamines and secondary alkanolamines.
- the method according to the invention is fundamentally different from the processes according to the prior art in that it implements a new absorbent solution which has never been described in the prior art.
- This absorbent solution comprises specific components in specific amounts.
- the absorbent solution used in the method according to the invention differs from the absorbent solution formed by water-alkanol mixtures in that it further comprises a thioalkanol C 2 to C ⁇ in a specific proportion in from 17% to 25% by mass relative to the total mass of the absorbent solution.
- the absorbing solution used in the process according to the invention is furthermore essentially different from the absorbing solution comprising an alkanolamine, a C 2 -C 4 thioalkanol and water used in the process described in the WO document. -Al-2007/083012 (FR-Al-2896244).
- the absorbent solution used in the process according to the invention comprises Advantageously, a mixture of specific amines, namely a mixture of at least one tertiary amine and at least one primary or secondary amine acting as an activator.
- Each of these amines, tertiary on the one hand, and primary or secondary on the other hand respectively, is present in a specific amount, defined by a narrow range, and the mixture of these amines is also present in a specific quantity also defined by a narrow beach.
- the other constituents of the mixture namely water and C 2 -C 4 thioalkanol are also present in specific amounts, defined by narrow ranges.
- the method for purifying a gas mixture containing acid gases according to the invention meets the needs mentioned above, it does not have the disadvantages, defects, limitations and disadvantages of the processes of the prior art, and it provides a solution to the problems of the processes of the prior art.
- the process according to the invention thanks to the specific absorbing solution which it implements, allows surprisingly a simultaneous elimination and, advantageously, in a single step not only of all the acid gases, that is to say the sulphide d hydrogen and carbon dioxide, but also other sulfur compounds such as mercaptans and COS, whereas the processes of the prior art require moreover several other treatment steps for all acid gases and all other compounds sulfur are removed.
- the elimination of acid gases CO 2 and 3 ⁇ 4S is generally carried out using a water-alkanolamine absorbent solution, for example using diethanolamine, methyldiethanolamine or a methyldiethanolamine-secondary amine mixture, such as, for example, HEP (hydroxyethylpiperazine) or piperazine.
- a water-alkanolamine absorbent solution for example using diethanolamine, methyldiethanolamine or a methyldiethanolamine-secondary amine mixture, such as, for example, HEP (hydroxyethylpiperazine) or piperazine.
- Processes using these water-alkanolamine absorbent solutions are effective in removing CO 2 and 3 ⁇ 4S, but do not allow the removal of other sulfur compounds such as mercaptans, and it is then necessary to carry out an additional step, by example with molecular sieves to eliminate mercaptans.
- the process according to the invention has the advantage of eliminating all the acid gases and all the other sulfur compounds during the step of absorbing or bringing the gaseous mixture into contact with the absorbing solution.
- the method according to the invention makes it possible to simultaneously remove not only CO 2 and H 2 S, but also other sulfur compounds such as mercaptans and COS, thus generally avoiding an additional step, in addition to the contacted for removal of mercaptans or COS.
- the method according to the invention thanks to the specific absorbing solution which it implements, allows a significant energy saving compared to the methods of the prior art which use a solution absorbent water-alkanolamines (see examples), but also with respect to the process described in the document O-A1-2007 / 083Q12 (FR-A1-2896244).
- the process according to the invention makes it possible to reduce the capital expenditure (“CAPEX”) and operating expenses (“OPEX”) of gas treatment plants and in particular natural gas thanks to the energy savings due to the optimization of the absorbent solution implemented, and the reduction of the size of downstream facilities for the removal of other sulfur compounds such as mercaptans or even the removal of some of these facilities (see examples).
- CAEX capital expenditure
- OPEX operating expenses
- Another of the advantages of the process according to the invention is the high stability of the absorbent solution used.
- Another essential advantage of the process according to the invention is its great flexibility. Indeed, the process according to the invention can be very easily adapted depending on the composition of the gaseous mixture to be treated and / or the specifications to be respected for each of the acid gases and each of the other sulfur compounds in the gaseous mixture resulting from the treatment.
- a larger proportion of activator will bring more reactivity and give a purified mixture containing less CO 2 whereas a lower proportion of activator will bring about less reactivity and give a purified mixture containing more CO 2 .
- the gaseous mixture to be treated by the process according to the invention may be any gaseous mixture containing at least one acidic gas chosen from sulfS hydrogen sulfide and CO 2 carbon dioxide.
- this gaseous mixture may contain, in addition to said at least one acid gas, for example in addition to H 2 S and CO 2 , at least one sulfur compound other than hydrogen sulfide 3 ⁇ 4S.
- Said at least one sulfur-containing compound other than hydrogen sulphide H 2 S may be chosen preferably from mercaptans and carbonyl sulphide COS.
- mercaptans which have the formula R-SH (where R is an alkyl radical comprising, for example, from 1 to 10 carbon atoms, in particular from 1 to 6 carbon atoms) include methyl mercaptan and ethyl mercaptan, but of other mercaptans, and in particular the C 3 SH to CeSH molecules may be present, generally at lower concentrations than methyl mercaptan and ethyl mercaptan.
- the hydrogen sulfide content of the gaseous mixture to be treated is generally from 40 ppm to 40% by volume, and after the contacting step this content can be lowered to 1 ppm. in volume.
- the CO 2 content of the gaseous mixture to be treated is generally 0.2% to 40% by volume, and after the contacting step this content can be lowered to 50 ppm by volume.
- the mercaptan content of the gaseous mixture to be treated is generally from 10 ppm to 1000 ppm by volume, and after the contacting step this content can be lowered to 1 ppm by volume.
- the SOC content of the gaseous mixture to be treated is generally from 5 ppm to 100 ppm by volume, and after the contacting step this content can be lowered to 2 ppm by volume.
- Gaseous mixtures containing acid gases are, for example, natural gas, synthesis gas, cracking gas, coke oven gas, gas from coal gasification, landfill gas, biogas combustion, and the gases obtained at a refinery's gas processing facilities.
- 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-C4 alkanes such as methane, ethane, propane and butane, unsaturated hydrocarbons such as ethylene or propylene, or aromatic hydrocarbons such as benzene, benzene, methacrylate and the like. 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% by volume.
- the tail gases obtained at the outlet of the sulfur chains, or the feed gases of the 3 ⁇ 4S enrichment units located upstream of the CLAUS processes, have a generally very low pressure, 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 C0 2 contents of these tail gases are variable and can reach 80% by volume.
- the present invention can also be applied to the treatment of mixtures, or of liquid hydrocarbon feeds.
- the tertiary amine of the absorbent solution used in the process according to the invention there is no limitation as to the tertiary amine of the absorbent solution used in the process according to the invention.
- the tertiary amine used should generally be soluble in water at the concentrations used in the absorbent solution.
- This amine can be, for example, aliphatic, cyclic or aromatic.
- the tertiary amine is selected from tertiary alkanolamines.
- 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 alkyl groups and the hydroxyalkyl groups may 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.
- 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
- TMPDA Diisopropylaminoethanol
- TEPDA Dimethylamino-2- dimethylaminoethoxyethane
- DMDEEDA N, N-dimethyl-N ', N' -diethylethylenediamine
- tris (2-hydroxyethyl) amine triethanolamine, EA
- tris (2-hydroxypropyl) amine triisopropanol
- tributylethanolamine TEA
- bis (2-hydroxyethyl) methylamine methyldiethanolamine, MDEA 2-diethylaminoethanol (dimethylethanolamine DMEA), 3-dimethylamino-1-propanol, 3-diethylamino-1-propanol, 2-diisopropylaminoethanol (DIEA)
- DIEA 2-diisopropylaminoethanol
- MDIPA N, N-bis (2-hydroxypropyl) methylamine or methyl diisopropanolamine
- tertiary alkanolamines which can be used in the process according to the invention are given in US-A-5,209,914 to the description of which reference may be made, in particular N methyldiethanolamine, triethanolamine, N-ethyldiethanolamine, 2-dimethylaminoethanol, 2-dimethylamino-1-propanol, 3-dimethylamino-1-propanol, 1-dimethylamino-2-propanol, N-methyl N-ethethanolamine, 2-diethylaminoethanol, 3-dimethylamino-1-butanol, 3-dimethylamino-2-butanol, N-methyl-N-isopropylethanolamine, N-methyl-N-ethyl-3 amino-1-propanol, 4-dimethylamino 1-butanol, 4-dimethylamino-2-butanol, 3-dimethylamino-2-methyl-1-propanol, 1-dimethylamino
- tertiary bis (diamines) such as ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylethylenediamine, N, N-diethyl-
- N r ⁇ '-diméthyléthylènediamine, ⁇ , ⁇ , ⁇ ', ⁇ '- tetraethylethylenediamine, N, N, N', N 'tetramethyl-1, 3- propanediamine (TMPDA), N, N, N', N ' 3-tetraethyl-1,3-propanediamine (TEPDA), N, N-dimethyl-N ', N' -diethylethylenediamine (DMDEEDA), 1-dimethylamino-2-dimethylaminoethoxyethane (bis [2- dimethylamino) ethyl] ether) in document US-A1-2010 / 0288125.
- the tertiary amine is selected from N-methyldiethanolamine (MDEA), triethanolamine (TEA), tributanolamine (TBA), and mixtures thereof.
- MDEA N-Methyldiethanolamine
- primary amine generally means a compound comprising at least one primary amine function.
- secondary amine in the meaning of the invention generally means a compound comprising at least one secondary amine function.
- This primary or secondary amine may be chosen from aliphatic, cyclic, aromatic or other amines.
- the primary or secondary amine used should generally be water soluble at the concentrations used in the absorbent solution.
- This primary or secondary amine can be, for example, aliphatic, cyclic or aromatic.
- the primary amines are selected from primary alkanolamines and secondary amines are selected from secondary alkanolamines.
- the secondary alkanolamines may be dialkanolamines, or alkylalkanolamines and the primary alkanolamines are monoalkanolamines.
- the alkyl groups and hydroxyalkyl groups are as defined above.
- activators are given in document US-A1-2008 / 0025893, these are 3-methylaminopropylamine (MAPA), piperazine, 2-methyl-piperazine, N-methylpiperazine (NMP), homopiperazine, piperidine, and morpholine (MO).
- MAA 3-methylaminopropylamine
- NMP N-methylpiperazine
- MO morpholine
- activators which can be used in the process according to the invention are given in WO-A1-2004 / 071624: it is piperazine, hydroxyethylpiperazine (HEP) and, bis (hydroxyethyl) piperazine, and mixtures thereof.
- activators that can be used in the process according to the invention are given in US-A-5, 209, 914; U.S.-A-5,277,885; and US-A-5,348,714, these are polyamines such as dipropylenetriamine (DPTA), diethylene triamine (DETA), triethylenetetramine (TETA) and tetraethylenepentamine (TEPA).
- DPTA dipropylenetriamine
- DETA diethylene triamine
- TETA triethylenetetramine
- TEPA tetraethylenepentamine
- Other activators mentioned in these documents which can be used in the process according to the invention are aminoethylethanolamine (AEEA), hexamethylenediamine (HMDA), dimethylaminopropylamine (DMAP) and 1,2-diaminocyclohexane (DACH).
- MOPA methoxypropylamine
- AEPZ aminoethoxypropylamine
- AEPD aminoethylpiperidine
- FA furfurylamine
- EMEA ethylmonoethanolamine
- the activator is selected from monoethanolamine (MEA), butylethanolamine (BEA), diethanolamine (DEA), aminoethylethanolamine (AEEA), piperazine, hydroxyethylpiperazine (HEP), aminoethylpiperazine (AEP), and their mixtures.
- MEA monoethanolamine
- BEA butylethanolamine
- DEA diethanolamine
- AEEA aminoethylethanolamine
- HEP hydroxyethylpiperazine
- AEP aminoethylpiperazine
- the C2-C thioalkanol has the formula: RS- (C 2 -C 4 alkylene) -OH, where R is any group, for example an alkyl group (generally C 1 -C 6 ) or an alkanol group ( generally C 1 -C 6 ), or a thiol group, or an alkylthioalkanol (generally C 1 -C 6 ) group.
- R is any group, for example an alkyl group (generally C 1 -C 6 ) or an alkanol group ( generally C 1 -C 6 ), or a thiol group, or an alkylthioalkanol (generally C 1 -C 6 ) group.
- the C 2 -C 4 thioalkanol is a dimeric molecule.
- C 2 to C 4 thioalkanol that can be used according to the invention is ethylene dithioethanol of formula (HO-CH 2 -CH 2 ) -S- (CH 2 -CH 2 ) -S- (CH 2 - CH 2 -OH).
- the preferred thioalkanol is ThioDiethylene Glycol or ThioDiGlycol (TDG) which is the compound of formula S (CH 2 -CH 2 -OH) 2 ⁇
- thioalkanols are very slightly soluble in the higher hydrocarbons (ethane, propane, butane, etc.) which may be present in the gaseous mixture, such as natural gas. Thioalkanols are therefore very little involved in the treatments downstream of the deacidification step.
- the invention uses a conventional method of absorption but with a new absorbent solution.
- a preferred absorbent solution is a solution consisting of water, MDEA, HEP and / or piperazine and TDG, in the respective proportions of 30%, 42%, 8%, and 20% by weight. .
- the contacting step is carried out at a temperature generally of 40.degree. 100 ° C, preferably 50 ° C to 90 ° C and a pressure of 1 to 150 bar, preferably 10 to 70 bar.
- the purification process as described above further comprises, after the contacting step, a regeneration step of the absorbent solution loaded with at least one acid gas and optionally at least one sulfur compound.
- this regeneration step of 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 further relates to an absorbent solution comprising, preferably consisting of:
- tertiary amine and activator from 4% to 12% by weight relative to the total mass of the absorbent solution of at least one activator; the total content of tertiary amine and activator being from 38% to 50% by weight relative to the total mass of the absorbent solution, the total concentration of tertiary amine and activator being between 3.8 and 4.2 mol / L;
- the tertiary amine is selected from tertiary alkanolamines.
- the tertiary amine is chosen from N-methyldiethanolamine (MDEA), triethanolamine (TEA), tributanolamine (TBA), and mixtures thereof.
- the activator is chosen from primary amines and secondary amines, more preferably from primary alkanolamines and secondary alkanolamines.
- the activator is chosen from monoethanolamine (MEA), butylethanolamine (BEA), diethanolamine (DEA), aminoethylethanolamine (AEEA), piperazine, hydroxyethylpiperazine (HEP) and aminoethylpiperazine (AEP). and their mixtures.
- MEA monoethanolamine
- BEA butylethanolamine
- DEA diethanolamine
- AEEA aminoethylethanolamine
- HEP hydroxyethylpiperazine
- AEP aminoethylpiperazine
- the thioalkanol is ethylene dithioethanol or ThioDiGlycol (TDG).
- a preferred absorbent solution is a solution consisting of water, MDEA, HEP and / or piperazine and TDG, in the respective proportions of 30%, 42%, 8%, and 20% by weight. .
- the invention can be implemented in any conventional absorption and regeneration installation using chemical absorbent solutions.
- Any gas-liquid or liquid-liquid contact apparatus may be used to carry out the contacting, absorption step.
- any type of column may be used as an absorption column. It may be in particular a column with perforated trays, a column with flaps 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.
- step of contacting, absorption can be carried out, for example in an absorption column, generally under the conditions of temperature and pressure already specified above.
- the absorption is carried out by contacting the gaseous mixture with the absorbent solution to a gas mixture flow generally 0, 23xl0 6 NnrV journey to 56xl0 6 NmV journey and an absorbent solution flow rate typically 800-50000 nrV journey.
- the purification process as described above further comprises, at the end of the contacting step, a regeneration step of the absorbent solution loaded with at least one acidic gas. and optionally at least one sulfur compound.
- the regeneration step of the absorbent solution is carried out conventionally by heating and separating at least one acid gas, which 1 'H 2 S, and optionally at least one sulfur compound, in a regeneration column.
- This regeneration step of the absorbent solution is generally carried out under the conditions of pressure and temperature already specified above.
- gases resulting from the expansion of the rich amine can be used as fuel gas "fuel gas", however according to the invention, these gases generally heavily loaded H 2 S are preferably treated, or possibly directly sent to a unit Sulfur production unit implementing the Claus reaction of controlled oxidation of 3 ⁇ 4S or in a synthesis facility of thio-organic compounds.
- Rich famine is then reheated in an amine / amine exchanger by the hot amine of the bottom of the regenerator, and optionally partially vaporized and recycled to feed the regeneration column.
- a reboiler generates steam which flows upstream in the column, resulting in acidic constituents such as H 2 S and C0 2 and possibly the 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 treatment is carried out of a gaseous mixture which is a natural gas, saturated with water, containing inter alia 5% by volume of CO 2 , 5% by volume of 3 ⁇ 4S, and 65 ppm by volume of mercaptans (50 ppm by volume of methyl mercaptan and 15 ppm by volume ethyl mercaptan) with aqueous absorbent solutions to remove acid gases.
- a gaseous mixture which is a natural gas, saturated with water, containing inter alia 5% by volume of CO 2 , 5% by volume of 3 ⁇ 4S, and 65 ppm by volume of mercaptans (50 ppm by volume of methyl mercaptan and 15 ppm by volume ethyl mercaptan) with aqueous absorbent solutions to remove acid gases.
- composition of this gaseous mixture is representative of the compositions of gaseous mixtures encountered in certain regions of the globe, particularly in Russia or the Middle East.
- This treatment is carried out either with an absorbent solution of the prior art consisting of water, MDEA, and HEP in weight (Comparative Example 1), or with an absorbent solution according to the invention constituted by water, MDEA, HEP and TDG, in the respective proportions of 30%, 2%, 8%, and 20% by weight.
- Example 1 (Comparative Example).
- a given gas flow is treated either
- Regeneration of this solvent requires an energy input of 53 MW.
- the treatment of the gaseous mixture described above with an absorbent solution according to the invention consisting of water, DEA, HEP and TDG, in the respective proportions of 30%, is carried out. 42%, 8%, and 20% by weight.
- a given gas flow is treated either
- the absorbent solution according to the invention achieved in a single step the specifications on acid gases, namely less than 2 and 50 ppm of H 2 S and CO 2 in the treated gas. but also to remove 95% of the mercaptans, which corresponds to a mercaptan content in the treated gas of less than 5 ppm by volume.
- the process according to the invention implementing the specific absorbent solution according to the invention makes it possible, however, to eliminate the additional stage of treatment of the regeneration gas. molecular sieves with a specific solvent.
- the absorbent solution used according to the invention also makes it possible to obtain a reduction in the energy consumption of the deacidification plant compared with an installation. deacidification using a conventional absorbent water-amine solution such as that used in Example 1.
- the observed gain is 7 MW, or 13%.
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Abstract
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BR112014028972-7A BR112014028972B1 (pt) | 2012-05-25 | 2013-05-23 | processo de purificação de misturas gasosas contendo gases ácidos |
EA201491942A EA027606B1 (ru) | 2012-05-25 | 2013-05-23 | Способ очистки газовых смесей, содержащих кислые газы |
US14/402,559 US10071339B2 (en) | 2012-05-25 | 2013-05-23 | Process for purifying gaseous mixtures containing acidic gases |
CA2874362A CA2874362C (fr) | 2012-05-25 | 2013-05-23 | Procede de purification de melanges gazeux contenant des gaz acides. |
CN201380027141.6A CN104334252A (zh) | 2012-05-25 | 2013-05-23 | 纯化含酸性气体的气体混合物的方法 |
NO20141524A NO20141524A1 (no) | 2012-05-25 | 2014-12-17 | Fremgangsmåte for opprenskning av gassblandinger inneholdende sure gasser |
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FR1254844A FR2990878B1 (fr) | 2012-05-25 | 2012-05-25 | Procede de purification de melanges gazeux contenant des gaz acides. |
FR1254844 | 2012-05-25 |
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US (1) | US10071339B2 (fr) |
CN (1) | CN104334252A (fr) |
BR (1) | BR112014028972B1 (fr) |
CA (1) | CA2874362C (fr) |
EA (1) | EA027606B1 (fr) |
FR (1) | FR2990878B1 (fr) |
MY (1) | MY180805A (fr) |
NO (1) | NO20141524A1 (fr) |
WO (1) | WO2013174907A1 (fr) |
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US10434462B2 (en) * | 2015-01-22 | 2019-10-08 | Carbon Clean Solutions Limited | Solvent and method for removing acid gases from a gaseous mixture |
ES2744432T3 (es) * | 2015-07-03 | 2020-02-25 | Dorf Ketal Chemicals India Private Ltd | Composiciones aditivas de eliminación de sulfuro de hidrógeno, y medio que las comprende |
WO2017165339A1 (fr) * | 2016-03-21 | 2017-09-28 | Board Of Regents, The University Of Texas System | Mélanges d'amines thermiquement dégradées pour la capture de co2 |
CN107433108A (zh) * | 2016-05-26 | 2017-12-05 | 中国石油化工股份有限公司 | 一种用于炼厂催化干气中脱硫脱碳的吸收溶剂 |
CN110385022B (zh) * | 2018-04-19 | 2022-07-15 | 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 |
CN115253600B (zh) * | 2022-08-08 | 2024-03-05 | 华北电力大学(保定) | 一种具有良好循环解吸稳定性、低腐蚀性的相变吸收剂的制备与应用 |
CN115178057A (zh) * | 2022-08-08 | 2022-10-14 | 北京清新环境技术股份有限公司 | 一种二氧化碳的化学吸收剂及其制备方法、应用和再生方法 |
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- 2013-05-23 BR BR112014028972-7A patent/BR112014028972B1/pt active IP Right Grant
- 2013-05-23 WO PCT/EP2013/060586 patent/WO2013174907A1/fr active Application Filing
- 2013-05-23 CN CN201380027141.6A patent/CN104334252A/zh active Pending
- 2013-05-23 MY MYPI2014003218A patent/MY180805A/en unknown
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Publication number | Publication date |
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CA2874362C (fr) | 2020-07-14 |
BR112014028972B1 (pt) | 2020-12-29 |
FR2990878B1 (fr) | 2014-05-16 |
CA2874362A1 (fr) | 2013-11-28 |
US10071339B2 (en) | 2018-09-11 |
FR2990878A1 (fr) | 2013-11-29 |
MY180805A (en) | 2020-12-09 |
BR112014028972A2 (pt) | 2017-07-25 |
EA027606B1 (ru) | 2017-08-31 |
CN104334252A (zh) | 2015-02-04 |
EA201491942A1 (ru) | 2015-04-30 |
US20150139877A1 (en) | 2015-05-21 |
NO20141524A1 (no) | 2014-12-17 |
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