WO2009156619A2 - Solution absorbante contenant un inhibiteur de dégradation dérivé du thiadiazole et méthode pour limiter la dégradation d'une solution absorbante - Google Patents
Solution absorbante contenant un inhibiteur de dégradation dérivé du thiadiazole et méthode pour limiter la dégradation d'une solution absorbante Download PDFInfo
- Publication number
- WO2009156619A2 WO2009156619A2 PCT/FR2009/000775 FR2009000775W WO2009156619A2 WO 2009156619 A2 WO2009156619 A2 WO 2009156619A2 FR 2009000775 W FR2009000775 W FR 2009000775W WO 2009156619 A2 WO2009156619 A2 WO 2009156619A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- thiadiazole
- degradation
- salt
- dithiobis
- dimercapto
- Prior art date
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- NEKCOKJRDOPRSK-UHFFFAOYSA-N Cc1nnc(SC)[s]1 Chemical compound Cc1nnc(SC)[s]1 NEKCOKJRDOPRSK-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
-
- 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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/38—Removing components of undefined structure
- B01D53/40—Acidic components
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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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2251/00—Reactants
- B01D2251/80—Organic bases or salts
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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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/50—Carbon oxides
- B01D2257/504—Carbon dioxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/05—Biogas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/06—Polluted air
-
- 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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/77—Liquid phase processes
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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 the field of the deacidification of a gaseous effluent. More specifically, the present invention provides compounds for reducing the degradation of an absorbent solution used to absorb the acidic compounds contained in a gaseous effluent, the absorbent solution comprising amines in aqueous solution.
- the deacidification of gaseous effluents is generally carried out by washing with an absorbent solution.
- the absorbent solution makes it possible to absorb the acid compounds present in the gaseous effluent (H 2 S, mercaptans, CO 2 , COS, SO 2 , CS 2 ).
- the amines have the disadvantage of degrading under the conditions of implementation.
- the amines can be degraded by oxygen forming acids such as, for example, formic acid, acetic acid or else oxalic acid in the amine solutions.
- HSS Heat Stable Sait
- HSAS Heat Stable Amine Sait
- the degraded solution is characterized by: a decrease in the absorption of the acidic compounds of the charge relative to a fresh solution of amine, an increase in the density of the absorbing solution, as well as its viscosity, which can lead to a loss of performance, the formation of more volatile amines polluting the treated gas and the acid gas from the regeneration step: ammonia, methylamine, dimethylamine and trimethylamine for example depending on the nature of the amine used, an accumulation of degradation products in the absorbent solution which may cause the need for treatment of the degraded solution, possible foaming problems due to degradation products.
- the degradation of the absorbing solution therefore penalizes the performance and the proper functioning of the gas deacidification units.
- degradation inhibiting agents compounds whose role is to prevent or limit the degradation of amino compounds, in particular the degradation caused by the oxidation phenomena. These compounds are commonly referred to as degradation inhibiting agents.
- the main known modes of action of the degradation-inhibiting agents are, depending on their nature, a reduction-type reaction and / or a capture, trapping and / or stabilization of the radicals formed in the absorbent solution in order to limit or prevent or interrupting reactions, including chain reactions, degradation.
- the patents US 5686016 and US 7056482 cite additives used to limit the degradation of absorbent solutions used respectively for the deacidification of natural gas and for the capture of CO 2 .
- the present invention proposes a family of degradation inhibiting agents which makes it possible in particular to reduce the degradation of an absorbent solution used for the absorption of acidic compounds contained in a gaseous effluent, the absorbent solution comprising compounds amines in aqueous solution.
- the absorbent solution according to the invention for absorbing the acidic compounds of a gaseous effluent, comprises: a) at least one amine, b) water, c) at least one degradation inhibiting compound for limiting the degradation of said amine, the degradation inhibitor compound having the general formula:
- X is selected from the group containing
- a hydrocarbon group containing 1 to 20 carbon atoms A hydrocarbon group containing 1 to 20 carbon atoms
- X may be a hydrocarbon group containing between 1 and 20 carbon atoms and including at least one heteroatom.
- the solution may comprise between 10% and 80% by weight of amine, between 10% and 90% of water and between 5 ppm and 5% by weight of degradation inhibiting compound.
- the degradation inhibiting compound may be selected from the group containing: 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), a salt of 5,5'-dithiobis (1, 3 4-thiadiazole-2 (3H) -thione), 2,5-dimercapto-1,3,4-thiadiazole, a salt of 2,5-dimercapto-1,3,4-thiadiazole, 5- (methylthio) -1,3,4-thiadiazole-2-thiol, a salt of 5- (methylthio) -1,3,4-thiadiazole-2-thiol, 5- (ethylthio) -1,3,4-thiadiazole; 2-thiol and a salt of 5- (ethylthio) -1,3,4-thiadiazole-2-thiol.
- the amine may be selected from the group containing: N, N, N ', N', N "-pentamethylethylenetriamine, piperazine, monoethanolamine, diethanolamine, methyldiethanolamine, diisopropanolamine, diglycolamine, a salt of glycine and a salt of taurine
- the degradation inhibiting compound may be chosen from among 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), the sodium salt of 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), 2,5-dimercapto-1,3,4-thiadiazole and the sodium salt of 2, 5-dimercapto-1,3,4-thiadiazole.
- the invention also proposes a process for absorbing acidic compounds contained in a gaseous effluent, in which the gaseous effluent is brought into contact with an aqueous solution containing at least one amine, and in which the degradation of said amine is controlled by introducing at least one degradation inhibiting compound having the general formula:
- X is selected from the group containing
- a hydrocarbon group containing 1 to 20 carbon atoms A hydrocarbon group containing 1 to 20 carbon atoms
- the aqueous solution can be used to absorb acidic compounds contained in one of the effluents of the group containing the natural gas, the combustion fumes, the synthesis gases, the refinery gases, tail gas from the Claus process, biomass fermentation gas, cement gas and incinerator fumes.
- At least one degradation inhibiting compound may be added to the aqueous solution selected from the group containing: 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), a salt of 5.5 1- dithiobis (1,3,4-thiadiazole-2 (3H) -thione), 2,5-dimercapto-1,3,4-thiadiazole, a salt of 2,5-dimercapto-1,3,4 thiadiazole, 5- (methylthio) -1,3,4-thiadiazole-2-thiol, a salt of 5- (methylthio) -1,3,4-thiadiazole-2-thiol, 5- (ethylthio) -1 , 3,4-thiadiazole-2-thiol and a salt of ⁇ - (ethylthio) -1,3,4-thiadiazole-2-thiol.
- At least one degradation inhibiting compound may be added chosen from: 5,5'-dithiobis (1,3,4-thiadiazole) -2 (3H) -thione), the sodium salt of 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), 2,5-dimercapto-1,3,4 thiadiazole, the sodium salt of 2,5-dimercapto-1,3,4-thiadiazole.
- an absorbent solution comprising organic compounds provided with an amine function in aqueous solution is substantially reduced in the presence of a small amount of inhibiting agents. degradation described below.
- the degradation inhibiting agents according to the invention are organic compounds derived from thiadiazole defined by the general formula:
- X is selected from the group containing
- ammonium defined broadly as the product of the protonation or quaternization of a molecule containing at least one nitrogen atom, and in which y is between 1 and 4, preferably between 1 and 2, n is between 0 and 4, preferably between 0 and 1.
- n is greater than 1, the pattern is repeated n times, the value of y is the same or different from one pattern to another.
- the absorbent solutions according to the invention can be used to deacidify the following gaseous effluents: natural gas, synthesis gases, combustion fumes, refinery gases, gases obtained at the bottom of the Claus process, the gases of fermentation of biomass, cement gas, incinerator fumes.
- gaseous effluents contain one or more of the following acidic compounds: CO 2 , 1 1 H 2 S, mercaptans, COS, SO 2 , NO 2 , CS 2 .
- the combustion fumes are produced in particular by the combustion of hydrocarbons, biogas, coal in a boiler or for a combustion gas turbine, for example for the purpose of producing electricity.
- These fumes can comprise between 50% and 80% of nitrogen, between 5% and 20% of carbon dioxide, between 1% and 10% of oxygen.
- the implementation of an absorbent solution for deacidifying a gaseous effluent is generally carried out by performing an absorption step followed by a regeneration step.
- the absorption stage consists in putting in contact the gaseous effluent with the absorbing solution.
- organic compounds having an amine function of the absorbent solution react with the acidic compounds contained in the effluent so as to obtain a gaseous effluent depleted of acidic compounds and an absorbent solution enriched in acidic compounds.
- the regeneration step includes heating and, optionally, relaxing, at least a portion of the absorbent solution enriched in acidic compounds to release the acidic compounds in gaseous form.
- the regenerated absorbent solution that is to say depleted in acidic compounds is recycled to the absorption step.
- the absorbent solution according to the invention comprises organic compounds in aqueous solution.
- the organic compounds are amines, that is to say that they comprise at least one amine function.
- the organic compounds may be in variable concentration, for example between 10% and 80% by weight, preferably between 20% and 60% by weight, in the aqueous solution.
- the absorbent solution may contain between 10% and 90% water.
- the organic compounds are amines such as N, N, N ', N', N "-pentamethylethylenetriamine or piperazine, for example piperazine is used for the treatment of natural gas and for the decarbonation of combustion fumes.
- the organic compounds can also be alkanolamines such as monoethanolamine (MEA), diethanolamine (DEA), methyldiethanolamine (MDEA), diisopropanolamine (DIPA) or diglycolamine, preferably MDEA and DEA are commonly used for deacidification of natural gas MEA is more particularly used for the decarbonation of combustion fumes.
- the organic compounds may also be amino acid salts such as glycine or taurine salts which are used in particular for the capture of CO2 in the combustion fumes.
- the absorbent solution according to the invention may contain compounds which physically absorb at least partially one or more acidic compounds of the gaseous effluent.
- the absorbent solution can comprise between 5% and 50% by weight of absorbent compounds of a physical nature such as methanol, sulfolane or N-formyl morpholine.
- the following degradation inhibiting agents are preferably used: 5,5'-dithiobis (1,3 ) 4-thiadiazole-2 (3H) -thione) , a salt of 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione) (especially the sodium, potassium, lithium, copper or ammonium salt of 5.5 1-dithiobis (1,3,4-thiadiazole-2 (3H) -thione)), 2,5-dimercapto-1,3,4-thiadiazole, a salt of 2,5-dimercapto-1,3,4 -thiadiazole (especially the sodium, potassium, lithium, copper or ammonium salt of 2,5-dimercapto-1,3,4-thiadiazole), 5- (methylthio) -i, 3,4 thiadiazole-2-thiol), a salt of 5- (methylthio) -1,3,4-thiadiazole-2-thiol) (in particular
- the following products are preferably used: the 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), the sodium salt of the 5 '5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thione), 2,5-dimercapto-1,3,4-thiadiazole, sodium salt of 2,5-dimercapto-1, 3,4-thiadiazole.
- the degradation inhibiting agents listed in the preceding paragraph are particularly well suited for the prevention of amine degradation in aqueous solution implemented in a process for capturing CO 2 contained in combustion fumes.
- one of the following compounds can be preferably used: '-dithiobis (1, 3,4-thiadiazole-2 (3H) -thione), the salt of sodium of 5,5'-dithiobis (1,3,4-thiadiazole-2 (3H) -thion ⁇ ), 2,5-dimercapto- 1, 3,4-thiadiazole, sodium salt of 2,5-dimercapto -1,3,4-thiadiazole.
- the absorbent solution according to the invention comprises an amount of degradation inhibiting agents defined by the general formula described above.
- the absorbent solution may comprise one or more different degradation inhibiting agents corresponding to said general formula.
- the degradation inhibiting agents according to the invention can be combined with other degradation inhibitor compounds of different chemical families.
- the absorbent solution comprises
- the degradation tests of an amine in aqueous solution are carried out according to the following procedure.
- amine solution 30% by weight in deionized water 100 ml of amine solution 30% by weight in deionized water are placed in a glass reactor surmounted by a condenser to prevent the evaporation of water.
- the degradation inhibiting agent incorporated in the aqueous amine solution is varied.
- the reactor is heated to 80 ° C. in an electric heating block.
- the solution is stirred at 1200 rpm by a magnetic bar.
- the presence of counter-blades prevents the formation of a vortex.
- 7 Nl / h of atmospheric air that is to say of unpurified ambient air, are brought into contact with the solution by means of a dip tube for 7 days at atmospheric pressure. An ion chromatographic analysis of the thus degraded solution is then carried out.
- the analytical method uses a column anion exchange, potash eluent and conductimetric detection. This analysis makes it possible to quantify the acetate, oxalate and formate ions, which are the species generally followed by those skilled in the art, since they bear witness to the degree of degradation of the amine.
- ppm contents of these different anions are given in the table below in the case of a solution of 30% by weight aqueous monoethanolamine (MEA) without degradation inhibitor, with 1% by weight of a conventional degradation inhibitor ( hydroquinone) and with 1% by weight of 5,5'-dithiobis (1, 3,4-thiadiazole-2 (3H) -thione), the sodium salt of 5,5'-dithiobis (1, 3,4 thiadiazole-2 (3H) -thione), 2,5-dimercapto-3,4-thiadiazole 1 I and sodium salt of 2,5-dimercapto-1, 3,4-thiadiazole.
- MEA monoethanolamine
- ND value not determined because below the detection limit of the analytical method for a given dilution of the sample analyzed.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09769460.8A EP2303428B1 (fr) | 2008-06-27 | 2009-06-23 | Solution absorbante contenant un inhibiteur de dégradation dérivé du thiadiazole et méthode pour limiter la dégradation d'une solution absorbante |
CA2723048A CA2723048C (fr) | 2008-06-27 | 2009-06-23 | Solution absorbante contenant un inhibiteur de degradation derive du thiadiazole et methode pour limiter la degradation d'une solution absorbante |
AU2009264120A AU2009264120B2 (en) | 2008-06-27 | 2009-06-23 | Absorbing solution containing a thiadiazole-derived degradation inhibitor and method for limiting the degradation of an absorbing solution |
US13/001,239 US8765088B2 (en) | 2008-06-27 | 2009-06-23 | Absorbent solution containing a thiadiazole-derived degradation inhibitor and method for limiting the degradation of an absorbent solution |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0803683A FR2933004B1 (fr) | 2008-06-27 | 2008-06-27 | Solution absorbante contenant un inhibiteur de degradation derive du thiadiazole et methode pour limiter la degradation d'une solution absorbante |
FR08/03683 | 2008-06-27 |
Publications (2)
Publication Number | Publication Date |
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WO2009156619A2 true WO2009156619A2 (fr) | 2009-12-30 |
WO2009156619A3 WO2009156619A3 (fr) | 2010-02-25 |
Family
ID=40317000
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/FR2009/000775 WO2009156619A2 (fr) | 2008-06-27 | 2009-06-23 | Solution absorbante contenant un inhibiteur de dégradation dérivé du thiadiazole et méthode pour limiter la dégradation d'une solution absorbante |
Country Status (6)
Country | Link |
---|---|
US (1) | US8765088B2 (fr) |
EP (1) | EP2303428B1 (fr) |
AU (1) | AU2009264120B2 (fr) |
CA (1) | CA2723048C (fr) |
FR (1) | FR2933004B1 (fr) |
WO (1) | WO2009156619A2 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011064469A1 (fr) * | 2009-11-30 | 2011-06-03 | IFP Energies Nouvelles | Solution absorbante contenant un inhibiteur de dégradation dérivé du thiazole ou de l'oxazole et procédé d'absorption de composés acides contenus dans un effluent gazeux |
FR2953145A1 (fr) * | 2009-11-30 | 2011-06-03 | Inst Francais Du Petrole | Solution absorbante contenant un inhibiteur de degradation derive de la pyrimidine ou de la triazine et procede d'absorption de composes acides contenus dans un effluent gazeux |
WO2011144823A1 (fr) * | 2010-05-20 | 2011-11-24 | IFP Energies Nouvelles | Solution absorbante contenant un inhibiteur de degradation derive soufre du thiadiazole et son utilisation dans un procede d'absorption |
WO2012012027A1 (fr) * | 2010-07-20 | 2012-01-26 | Powerspan Corp. | Milieux d'absorption servant à retirer le co2 d'un courant gazeux et procédé l'utilisant |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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TWI409136B (zh) | 2006-07-19 | 2013-09-21 | Innopad Inc | 表面具微溝槽之化學機械平坦化墊 |
FR2970424B1 (fr) * | 2011-01-19 | 2013-11-08 | IFP Energies Nouvelles | Solution absorbante contenant une combinaison d'inhibiteurs de degradation comportant un derive du thiadiazole et procede d'absorption de composes acides contenus dans un effluent gazeux |
CN102423606B (zh) * | 2011-09-06 | 2013-10-02 | 中电投远达环保工程有限公司 | 二氧化碳吸收剂的添加剂及其运用 |
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US2655543A (en) * | 1950-10-06 | 1953-10-13 | Du Pont | Stabilized aromatic amines |
EP0592956A1 (fr) * | 1992-10-13 | 1994-04-20 | The Lubrizol Corporation | Lubrifiants, graisses et fluides aqueux contenant des additifs derivés de dimercaptothiadiazoles |
WO2005035700A1 (fr) * | 2003-10-10 | 2005-04-21 | R.T. Vanderbilt Company, Inc. | Compositions lubrifiantes contenant de l'huile de base d'ester synthetique, des composes de molybdene et des composes a base de thiadiazole |
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2008
- 2008-06-27 FR FR0803683A patent/FR2933004B1/fr active Active
-
2009
- 2009-06-23 US US13/001,239 patent/US8765088B2/en active Active
- 2009-06-23 WO PCT/FR2009/000775 patent/WO2009156619A2/fr active Application Filing
- 2009-06-23 CA CA2723048A patent/CA2723048C/fr active Active
- 2009-06-23 EP EP09769460.8A patent/EP2303428B1/fr active Active
- 2009-06-23 AU AU2009264120A patent/AU2009264120B2/en active Active
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US2655543A (en) * | 1950-10-06 | 1953-10-13 | Du Pont | Stabilized aromatic amines |
EP0592956A1 (fr) * | 1992-10-13 | 1994-04-20 | The Lubrizol Corporation | Lubrifiants, graisses et fluides aqueux contenant des additifs derivés de dimercaptothiadiazoles |
WO2005035700A1 (fr) * | 2003-10-10 | 2005-04-21 | R.T. Vanderbilt Company, Inc. | Compositions lubrifiantes contenant de l'huile de base d'ester synthetique, des composes de molybdene et des composes a base de thiadiazole |
EP1582250A2 (fr) * | 2004-03-09 | 2005-10-05 | Basf Aktiengesellschaft | Absorbant avec une réstistance améliorée à l'oxidation et procédé pour désacidifier des courants de fluides |
FR2900842A1 (fr) * | 2006-05-10 | 2007-11-16 | Inst Francais Du Petrole | Procede de desacidification d'un effluent gazeux avec extraction des produits a regenerer |
Cited By (10)
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WO2011064469A1 (fr) * | 2009-11-30 | 2011-06-03 | IFP Energies Nouvelles | Solution absorbante contenant un inhibiteur de dégradation dérivé du thiazole ou de l'oxazole et procédé d'absorption de composés acides contenus dans un effluent gazeux |
FR2953145A1 (fr) * | 2009-11-30 | 2011-06-03 | Inst Francais Du Petrole | Solution absorbante contenant un inhibiteur de degradation derive de la pyrimidine ou de la triazine et procede d'absorption de composes acides contenus dans un effluent gazeux |
WO2011064470A1 (fr) * | 2009-11-30 | 2011-06-03 | IFP Energies Nouvelles | Solution absorbante contenant un inhibiteur de dégradation. dérivé de la pyrimidine ou de la triazine et procédé d'absorption de composés acides contenus dans un effluent gazeux |
FR2953147A1 (fr) * | 2009-11-30 | 2011-06-03 | Inst Francais Du Petrole | Solution absorbante contenant un inhibiteur de degradation derive du thiazole ou de l'oxazole et procede d'absortion de composes acides contenus dans un effluent gazeux |
US8562927B2 (en) | 2009-11-30 | 2013-10-22 | Ifp | Absorbent solution containing a breakdown inhibitor derived from thiazole or from oxazole and absorption process for acid compounds contained in a gaseous effluent |
US9211495B2 (en) | 2009-11-30 | 2015-12-15 | IFP Energies Nouvelles | Absorbent solution containing a breakdown inhibitor derived from pyrimidine or from triazine and absorption process for acid compounds contained in a gaseous effluent |
WO2011144823A1 (fr) * | 2010-05-20 | 2011-11-24 | IFP Energies Nouvelles | Solution absorbante contenant un inhibiteur de degradation derive soufre du thiadiazole et son utilisation dans un procede d'absorption |
FR2960163A1 (fr) * | 2010-05-20 | 2011-11-25 | Inst Francais Du Petrole | Solution absorbante contenant un inhibiteur de degradation derive soufre du thiadiazole et procede d'absorption de composes acides contenus dans un effluent gazeux |
WO2012012027A1 (fr) * | 2010-07-20 | 2012-01-26 | Powerspan Corp. | Milieux d'absorption servant à retirer le co2 d'un courant gazeux et procédé l'utilisant |
CN103097000A (zh) * | 2010-07-20 | 2013-05-08 | 鲍尔斯潘公司 | 用于从气流洗涤co2的吸收介质和使用所述介质的方法 |
Also Published As
Publication number | Publication date |
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CA2723048C (fr) | 2014-08-12 |
AU2009264120B2 (en) | 2014-05-15 |
FR2933004B1 (fr) | 2010-08-20 |
CA2723048A1 (fr) | 2009-12-30 |
WO2009156619A3 (fr) | 2010-02-25 |
AU2009264120A1 (en) | 2009-12-30 |
FR2933004A1 (fr) | 2010-01-01 |
US8765088B2 (en) | 2014-07-01 |
EP2303428A2 (fr) | 2011-04-06 |
EP2303428B1 (fr) | 2016-02-10 |
US20110110834A1 (en) | 2011-05-12 |
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