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WO1997029834A1 - Procede permettant l'elimination de soufre sous forme liquide durant le traitement d'un gaz - Google Patents

Procede permettant l'elimination de soufre sous forme liquide durant le traitement d'un gaz Download PDF

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Publication number
WO1997029834A1
WO1997029834A1 PCT/US1996/018727 US9618727W WO9729834A1 WO 1997029834 A1 WO1997029834 A1 WO 1997029834A1 US 9618727 W US9618727 W US 9618727W WO 9729834 A1 WO9729834 A1 WO 9729834A1
Authority
WO
WIPO (PCT)
Prior art keywords
polar organic
organic solvent
sulfur
solvent
hydrogen sulfide
Prior art date
Application number
PCT/US1996/018727
Other languages
English (en)
Inventor
Mark A. Plummer
John J. Waycuilis
Original Assignee
Marathon Oil Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Marathon Oil Company filed Critical Marathon Oil Company
Priority to CA 2240319 priority Critical patent/CA2240319A1/fr
Priority to AU10227/97A priority patent/AU1022797A/en
Publication of WO1997029834A1 publication Critical patent/WO1997029834A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B17/00—Sulfur; Compounds thereof
    • C01B17/02—Preparation of sulfur; Purification
    • C01B17/04—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides
    • C01B17/05—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides by wet processes
    • 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
    • B01D53/1418—Recovery of products
    • 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
    • B01D53/1456—Removing acid components
    • B01D53/1468—Removing hydrogen sulfide

Definitions

  • the present invention relates to a process for removing liquid sulfur from a reaction mixture during a gas treating process, and more particularly, to a process for removing hydrogen sulfide from a gaseous stream wherein sulfur is removed from a reaction vessel as a slurry with a portion of the reaction mixture, heated to its melting point, and washed to remove any remaining reaction mixture therefrom.
  • gaseous by-products containing hydrogen sulfide either alone or in a mixture with water and/or other gases, such as, methane, carbon dioxide, low molecular weight hydrocarbons, nitrogen, ammonia etc.
  • natural gas which is produced from subterranean formations often contains similar gases to those gaseous by-products listed above.
  • these gaseous by-products were oxidized by common oxidation processes, such as the Claus process, to obtain sulfur.
  • hydrogen sulfide is oxidized by direct contact with air to produce sulfur and water.
  • one such alternative process involves contacting within a reactor a feed gas containing hydrogen sulfide with an anthraquinone which is dissolved in a polar organic solvent.
  • This polar organic solvent preferably has a polarity greater than about 3 Debye units. The resulting reaction between hydrogen sulfide and anthraquinone yields sulfur and the corresponding anthrahydroquinone.
  • the anthraquinone is recycled back to the reactor and the hydrogen gas is recovered as a product.
  • the insoluble sulfur e.g.
  • S 8 or other forms of polymerized sulfur is conventionally withdrawn from the reactor as a precipitate in the reaction solution, is separated from solution by filtration, centrifugation or other means known in the art, is washed to remove the polar organic solvent, dissolved anthrahydroquinone, any unreacted anthraquinone and complexing agent, and is dried or melted to a liquid form.
  • a significant disadvantage of this process is that the removal of sulfur as a solid with subsequent washing to obtain maximum purity is expensive due to the filtration and centrifuge equipment which is required. To date, however, removal of sulfur as a solid has been more practical than removal of sulfur as a liquid from the reaction solution.
  • one characterization of the present invention comprises a process for converting hydrogen sulfide to sulfur.
  • a feed gas containing hydrogen sulfide is contacted with a polar organic solvent having a quinone dissolved therein.
  • the hydrogen sulfide reacts with the quinone to produce sulfur and a corresponding hydroquinone in the solvent.
  • Sulfur is concentrated in a portion of the polar organic solvent which is heated to a temperature sufficient to melt the sulfur.
  • the molten sulfur is removed from the polar organic solvent.
  • the present invention relates to the removal of liquid sulfur from a reaction mixture obtained during a process for the conversion of hydrogen sulfide which is initially contained in a gaseous feed stream to elemental sulfur.
  • the gaseous feed containing hydrogen sulfide (H 2 S) is contacted in a reactor with a polar organic solvent having a quinone dissolved therein.
  • the polar organic solvent may also have a complexing agent dissolved therein.
  • the solvent preferentially solubilizes hydrogen sulfide from the feed gas to form a reaction solution which is maintained in the reactor at a temperature and a pressure, as hereinafter discussed, and for a time which is sufficient to convert the hydrogen sulfide and quinone to sulfur and the corresponding hydroquinone.
  • the solvent also solubilizes significant portion of the water, low molecular weight hydrocarbons, i.e. C 2 - C 8 , and/or carbon dioxide present in the gaseous feed stream. Should the feed gas contain large quantities of such gases other than hydrogen sulfide which are inert to this process, i.e.
  • the feed gas may contain other sulfur compounds, such as COS, CS, and mercaptans, which are dissolved in the polar organic solvent and converted in the process to H2S, recycled to the reactor, and converted to sulfur.
  • the absorber and reactor may be separate components of a single processing unit or a single reaction vessel, for example a stirred tank, in which both functions are performed.
  • the polar organic solvent utilized in the process of the present invention is chosen to have a high polarity, i.e.greater than about 3.0 Debye units, and yet remain stable at dehydrogenation temperatures.
  • Suitable polar organic solvents include N-methyl-2-pyrrolidinone, N,N-dimethylacetamide, N,N- dimethylformamaide, sulfolane (tetrahydrothiophene-1 ,1 -dioxide), acetonitrile, 2- nitropropane, propylene carbonate and mixtures thereof.
  • the most preferred solvent is N-methyl-2-pyrrolidinone (NMP).
  • NMP N-methyl-2-pyrrolidinone
  • a complexing agent may also be incorporated into the polar organic solvent.
  • the pK neighbor of the complexing agent is less than about 13.0, more preferably less than about 9.0, and most preferably less than about 6.0.
  • the pK favor values are based on , (equilibrium constant) of 14.0 for the dissociation of water and are measured at 25° C.
  • Suitable complexing agents are selected from amines, amides, ureas, nitrogen containing heterocyclic aromatics, quanidines, imidazoles, and mixtures thereof.
  • complexing agents can also be substituted with alkyl, aryl and organic alcohol groups.
  • suitable complexing agents are n- methylacetamide, pyridine, substituted pyridines, diethylmethylamine, tributylamine, methyldiethanolamine and tetramethylurea.
  • the preferred complexing agents are diethylmethylamine (DEMA), methyldiethanolamine (MDEA), tributylamine (TBA), pyridine (PY), and substituted pyridines.
  • the molar ratio of complexing agent to quinone in the polar organic solvent is about 1 :50 to about 2:1 and preferably about 1:6 to about 1:1.
  • the quinone utilized in the process of the present invention is selected from anthraquinones, benzoquinones, napthaquinones, and mixtures thereof and are chosen to maximize its reaction with H 2 S.
  • Choice of the quinone is based on such properties as the solubility of quinone in the polar organic solvent. Solubility is a function of the groups substituted on the quinone.
  • alkyl quinones have much higher solubilities than sulfonated quinones.
  • Useful alkylquinones are ethyl, t-butyl, t-amyl and s-amyl quinones and mixtures thereof because of their relatively high solubilities in most polar organic solvents.
  • the reaction solution i.e. the polar organic solvent having a suitable quinone, complexing agent and hydrogen sulfide dissolved therein, is maintained in the H 2 S reactor at a temperature of from about 0° C. to about 70°
  • the treated feed gas is removed from the reactor and transported for further treatment or for use.
  • the insoluble sulfur e.g. S ⁇ or other forms of polymerized sulfur
  • the insoluble sulfur is withdrawn from the reactor as a precipitate in the reaction solution and is allowed to separate from a significant portion, i.e. about 90 to 95 vol %, of the reaction solution by settling at a temperature of about 0° C. to about 30° C.
  • the insoluble sulfur is then removed from the vessel in which such separation occurs as a slurry with the remaining, about 5 to 10 vol%, reaction solution and is transported and introduced into a melter at a point immediately above any melted sulfur present therein. In the melter, the slurry is heated to a temperature slightly above the 112° C.
  • insoluble sulfur i.e. S8
  • any suitable means for example by using steam in an internal heat exchanger which is positioned within the liquid sulfur phase present in the melter. Any hydroquinone which is present in the slurry will be converted to quinone and hydrogen sulfide upon reaction with S 8 .
  • the reaction solution and the liquid sulfur are separately removed from the melter.
  • the liquid sulfur is washed with a suitable solvent, for example water, hydrocarbons or oxygenated hydrocarbons, such as, acetone, 3-pentanone, or mixtures thereof, to dissolve any remaining reaction solution from the liquid sulfur.
  • This wash solvent has a boiling point of at least about 50° C, preferably at least about 100° C, and most preferably at least about 150° C below that of the polar organic solvent.
  • the pressure on the wash solvent and the reaction solution is reduced to fractionate the solvent from the dissolved reaction mixture and the wash solvent is recycled back to the washing step. If water is utilized as the wash solvent, the water is recycled back to the reactor where it is dissolved in the polar organic solvent.
  • reaction solution which is removed from the melter is combined with the reaction solution from which the sulfur slurry was previously separated.
  • the combined reaction solution which contains hydroquinone, any unreacted quinone, complexing agent, solvent, and unreacted compounds from the feed gas, such as hydrogen sulfide, COS, CS 2> carbon dioxide, mecaptans, and unrecovered sulfur is maintained at a temperature of from about 70 " C. to about 220 ' C. and at a pressure of from about 0.01 to about 4.0 atmospheres to convert COS, CS 2 , mercaptans and unrecovered sulfur to hydrogen sulfide.
  • reaction solution is then fed to a flash tank or fractionator where substantially all unreacted feed gas constituents, including water, C0 2 and/or low molecular weight hydrocarbons, are removed from solution, separated and recovered as products.
  • the remaining gas which consists primarily of unreacted H 2 S is recycled to the reactor.
  • the solution is withdrawn from the flash tank or fractionator and is further processed to convert the hydroquinone to the corresponding quinone and products, such as hydrogen, hydrogen peroxide or water.
  • the reaction solution further heated to from about 220° C. to about 350° C. at a pressure sufficient to prevent solvent boiling.
  • the heated solution is then fed to a dehydrogenation reactor where the hydroquinone is catalytically or thermally converted to the initial quinone and hydrogen gas under the temperature and pressure conditions stated above.
  • the presence of a complexing agent in the reaction solution fed to the dehydrogenation reactor results in an unexpected and marked increase in the selectivity of hydroquinone to quinone and hydrogen product, and thus, the attendant decrease in unwanted hydrogenolysis by- products.
  • the 50.06 gms of liquid sulfur phase is slurried with 10.00 gm of liquid acetone at 123 -133° C. and 10 atmospheres pressure to keep the mixture as a liquid phase. Essentially all of the 0.73 gms of reaction mixture is extracted into the liquid acetone. The slurry is then separated and one essentially pure liquid sulfur product is withdrawn from the separator. The acetone and reaction mixture phase is also removed from the separator and fractionated at 2 atmospheres to remove essentially all of the acetone as vapor from the liquid reaction mixture. The liquid reaction mixture is mixed with the 49.27 gms of starting reaction mixture. The acetone is pressurized back to 10 atmospheres to form a liquid phase.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Industrial Gases (AREA)
  • Gas Separation By Absorption (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention, qui porte sur un procédé permettant d'éliminer du soufre liquide d'un mélange réactionnel durant le traitement d'un gaz, a notamment trait à un procédé d'extraction d'hydrogène sulfuré d'un courant gazeux. Le soufre qui s'est formé durant le processus est retiré d'un mélange réactionnel par le biais d'une première concentration de ce soufre dans une petite partie du mélange réactionnel puis d'un réchauffement de ladite partie à une température suffisante pour le faire fondre. Le soufre fondu est alors retiré du mélange réactionnel et lavé à l'aide d'un solvant approprié pour éliminer tout reliquat de mélange réactionnel.
PCT/US1996/018727 1996-02-14 1996-11-22 Procede permettant l'elimination de soufre sous forme liquide durant le traitement d'un gaz WO1997029834A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA 2240319 CA2240319A1 (fr) 1996-02-14 1996-11-22 Procede permettant l'elimination de soufre sous forme liquide durant le traitement d'un gaz
AU10227/97A AU1022797A (en) 1996-02-14 1996-11-22 Process for removing sulfur as a liquid during gas treating

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60122196A 1996-02-14 1996-02-14
US08/601,221 1996-02-14

Publications (1)

Publication Number Publication Date
WO1997029834A1 true WO1997029834A1 (fr) 1997-08-21

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PCT/US1996/018727 WO1997029834A1 (fr) 1996-02-14 1996-11-22 Procede permettant l'elimination de soufre sous forme liquide durant le traitement d'un gaz

Country Status (4)

Country Link
AU (1) AU1022797A (fr)
ID (1) ID15936A (fr)
MX (1) MX9804833A (fr)
WO (1) WO1997029834A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6887447B2 (en) * 2000-10-13 2005-05-03 Baker Hughes Incorporated Hydrogen sulfide abatement in molten sulfur
WO2012003267A2 (fr) 2010-07-01 2012-01-05 Baker Hughes Incorporated Formulation aqueuse de piégeur de h2s/mercaptan pour fluides dans des applications en champ pétrolifère et en raffinerie
EP2201086A4 (fr) * 2007-10-15 2013-03-13 Baker Hughes Inc Piégeur multifonctionnel pour fluides hydrocarbonés
WO2016105341A1 (fr) * 2014-12-22 2016-06-30 Halliburton Energy Services, Inc. Additifs synergiques d'épuration de sulfures destinés à être utilisés dans des opérations en champ pétrolifère

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020149A (en) * 1975-05-02 1977-04-26 Exxon Research And Engineering Company Process for the production of sulfur
US4069302A (en) * 1976-08-30 1978-01-17 Fmc Corporation Purification of sulfur
US4174383A (en) * 1973-12-17 1979-11-13 Institut Francais Du Petrole Process for purifying a sulfur dioxide containing gas with production of elemental sulfur
US4243648A (en) * 1979-06-20 1981-01-06 Union Oil Company Of California Method for removing hydrogen sulfide from gas streams
US4304570A (en) * 1979-02-09 1981-12-08 Gottfried Bischoff Bau Kompl. Gasreinigungs- und Wasserruckkuhlanlagen Gmbh & Co. KG. Method of separation of sulfur from a scrubbing liquid
US4592905A (en) * 1985-01-14 1986-06-03 Marathon Oil Company Conversion of hydrogen sulfide to sulfur and hydrogen
EP0207509A2 (fr) * 1985-07-03 1987-01-07 Linde Aktiengesellschaft Procédé et récipient de séparation pour séparer une suspension de lessive et de soufre
US4637926A (en) * 1984-08-01 1987-01-20 Ciba-Geigy Corporation Method of removing hydrogen sulphide from gases
US4664902A (en) * 1985-08-23 1987-05-12 Shell Oil Company Recovery of sulfur from a solid sulfur-containing solution of solubilized iron chelate of nitrilotriacetic acid
US4684514A (en) * 1985-07-22 1987-08-04 Air Products And Chemicals, Inc. High pressure process for sulfur recovery from a hydrogen sulfide containing gas stream
US4705676A (en) * 1985-08-23 1987-11-10 Shell Oil Company Recovery of sulfur from a solid sulfur-containing solution of a solubilized iron chelate
US5030438A (en) * 1986-07-10 1991-07-09 Societe Nationale Elf Aquitaine (Production) Catalytic removal of hydrogen sulfides from liquid sulfur
US5057298A (en) * 1988-08-16 1991-10-15 Pipco, Inc. Process for recovery of sulfur values from a gas stream
US5334363A (en) * 1992-12-01 1994-08-02 Marathon Oil Company Process for recovering sulfur and hydrogen from hydrogen sulfide

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4174383A (en) * 1973-12-17 1979-11-13 Institut Francais Du Petrole Process for purifying a sulfur dioxide containing gas with production of elemental sulfur
US4020149A (en) * 1975-05-02 1977-04-26 Exxon Research And Engineering Company Process for the production of sulfur
US4069302A (en) * 1976-08-30 1978-01-17 Fmc Corporation Purification of sulfur
US4304570A (en) * 1979-02-09 1981-12-08 Gottfried Bischoff Bau Kompl. Gasreinigungs- und Wasserruckkuhlanlagen Gmbh & Co. KG. Method of separation of sulfur from a scrubbing liquid
US4243648A (en) * 1979-06-20 1981-01-06 Union Oil Company Of California Method for removing hydrogen sulfide from gas streams
US4637926A (en) * 1984-08-01 1987-01-20 Ciba-Geigy Corporation Method of removing hydrogen sulphide from gases
US4592905A (en) * 1985-01-14 1986-06-03 Marathon Oil Company Conversion of hydrogen sulfide to sulfur and hydrogen
EP0207509A2 (fr) * 1985-07-03 1987-01-07 Linde Aktiengesellschaft Procédé et récipient de séparation pour séparer une suspension de lessive et de soufre
US4684514A (en) * 1985-07-22 1987-08-04 Air Products And Chemicals, Inc. High pressure process for sulfur recovery from a hydrogen sulfide containing gas stream
US4664902A (en) * 1985-08-23 1987-05-12 Shell Oil Company Recovery of sulfur from a solid sulfur-containing solution of solubilized iron chelate of nitrilotriacetic acid
US4705676A (en) * 1985-08-23 1987-11-10 Shell Oil Company Recovery of sulfur from a solid sulfur-containing solution of a solubilized iron chelate
US5030438A (en) * 1986-07-10 1991-07-09 Societe Nationale Elf Aquitaine (Production) Catalytic removal of hydrogen sulfides from liquid sulfur
US5057298A (en) * 1988-08-16 1991-10-15 Pipco, Inc. Process for recovery of sulfur values from a gas stream
US5334363A (en) * 1992-12-01 1994-08-02 Marathon Oil Company Process for recovering sulfur and hydrogen from hydrogen sulfide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HYDROCARBON PROCESSING, April 1987, PLUMMER M.A., "Gas Processing Developments: Sulfur and Hydrogen from Hydrogen Sulfide", pages 38-40. *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6887447B2 (en) * 2000-10-13 2005-05-03 Baker Hughes Incorporated Hydrogen sulfide abatement in molten sulfur
EP2201086A4 (fr) * 2007-10-15 2013-03-13 Baker Hughes Inc Piégeur multifonctionnel pour fluides hydrocarbonés
US9708547B2 (en) 2007-10-15 2017-07-18 Baker Hughes Incorporated Water-based formulation of H2S/mercaptan scavenger for fluids in oilfield and refinery applications
WO2012003267A2 (fr) 2010-07-01 2012-01-05 Baker Hughes Incorporated Formulation aqueuse de piégeur de h2s/mercaptan pour fluides dans des applications en champ pétrolifère et en raffinerie
EP2600966A4 (fr) * 2010-07-01 2014-09-24 Baker Hughes Inc Formulation aqueuse de piégeur de h2s/mercaptan pour fluides dans des applications en champ pétrolifère et en raffinerie
WO2016105341A1 (fr) * 2014-12-22 2016-06-30 Halliburton Energy Services, Inc. Additifs synergiques d'épuration de sulfures destinés à être utilisés dans des opérations en champ pétrolifère
GB2545614A (en) * 2014-12-22 2017-06-21 Halliburton Energy Services Inc Synergistic sulfide scavenging additives for use in oilfield operations
AU2014414855B2 (en) * 2014-12-22 2018-08-02 Halliburton Energy Services, Inc. Synergistic sulfide scavenging additives for use in oilfield operations
AU2014414855C1 (en) * 2014-12-22 2018-11-08 Halliburton Energy Services, Inc. Synergistic sulfide scavenging additives for use in oilfield operations
US10550309B2 (en) 2014-12-22 2020-02-04 Multi-Chem Group, Llc Synergistic sulfide scavenging additives for use in oilfield operations
US11078403B2 (en) 2014-12-22 2021-08-03 Halliburton Energy Services, Inc. Synergistic sulfide scavenging additives for use in oilfield operations
GB2545614B (en) * 2014-12-22 2022-02-23 Halliburton Energy Services Inc Synergistic sulfide scavenging additives for use in oilfield operations

Also Published As

Publication number Publication date
ID15936A (id) 1997-08-21
MX9804833A (es) 1998-09-30
AU1022797A (en) 1997-09-02

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