US20080312074A1 - Hydrotreating catalyst sulphiding agent and its use for in situ and ex situ presulphidation - Google Patents

Hydrotreating catalyst sulphiding agent and its use for in situ and ex situ presulphidation Download PDF

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US20080312074A1
US20080312074A1 US11/961,164 US96116407A US2008312074A1 US 20080312074 A1 US20080312074 A1 US 20080312074A1 US 96116407 A US96116407 A US 96116407A US 2008312074 A1 US2008312074 A1 US 2008312074A1
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sulphiding
catalyst
sulphiding agent
disulphide
situ
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US11/961,164
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English (en)
Inventor
Francis Humblot
Paul-Guillaume Schmitt
Georges Fremy
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Arkema France SA
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Arkema France SA
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Priority claimed from FR0655884A external-priority patent/FR2910349A1/fr
Application filed by Arkema France SA filed Critical Arkema France SA
Priority to US11/961,164 priority Critical patent/US20080312074A1/en
Assigned to ARKEMA FRANCE reassignment ARKEMA FRANCE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FREMY, GEORGES, HUMBLOT, FRANCIS, SCHMITT, PAUL-GUILLAUME
Publication of US20080312074A1 publication Critical patent/US20080312074A1/en
Priority to US12/858,647 priority patent/US9353054B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/20—Sulfiding
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G51/00—Compounds of cobalt
    • C01G51/04—Oxides; Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G53/00—Compounds of nickel
    • C01G53/04—Oxides; Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
    • C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
    • C10G45/06—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof
    • C10G45/08—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof in combination with chromium, molybdenum, or tungsten metals, or compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/882—Molybdenum and cobalt
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/80—Compositional purity

Definitions

  • the present invention relates to the field of the hydrotreating of hydrocarbon feedstocks and has more particularly as subject-matter a process for the presulphidation of the catalysts used for this purpose.
  • the catalysts for the hydrotreating of hydrocarbon feedstocks to which the present invention relates are used, under appropriate conditions, for converting, in the presence of hydrogen, organosulphur compounds to hydrogen sulphide, which operation is known as hydrodesulphurization (HDS), and for converting organonitrogen compounds to ammonia in an operation known as hydrodenitrogenation (HDN).
  • HDS hydrodesulphurization
  • HDN hydrodenitrogenation
  • catalysts are generally based on metals from Groups VI B and VIII of the Periodic Table of the Elements, such as molybdenum, tungsten, nickel and cobalt.
  • the most commonly used hydrotreating catalysts are formulated from cobalt-molybdenum (Co—Mo), nickel-molybdenum (Ni—Mo) and nickel-tungsten (Ni—W) systems, deposited on porous inorganic supports, such as aluminas, silicas or silicas/aluminas.
  • catalysts manufactured industrially at very large tonnages, are supplied to the user in their oxide forms (for example, catalysts formed of cobalt oxide-molybdenum oxide on alumina, symbolized by the abbreviation: Co—Mo/alumina).
  • Sulphur-comprising additives have been provided for improving the sulphidation of the catalysts.
  • the method consists in incorporating a sulphur compound (spiking agent) in a feedstock, such as a naphtha, or in a specific fraction, such as a VGO (vacuum gas oil) or an LGO (light gas oil).
  • a sulphur compound spikeking agent
  • VGO vacuum gas oil
  • LGO light gas oil
  • EP 64 429 describes an effective method for sulphidation by means of a sulphidation feedstock composed of a mixture of at least one sulphur compound and a hydrocarbon feedstock and of a specific temperature profile; mention is made, among sulphur compounds, of carbon disulphide, mercaptans, thiophene compounds, (di)sulphides and hydrogen sulphide, dimethyl disulphide (DMDS) being particularly preferred for the sulphidation of the catalysts and with dimethyl disulphide is described in the patent.
  • a sulphidation feedstock composed of a mixture of at least one sulphur compound and a hydrocarbon feedstock and of a specific temperature profile
  • dialkyl disulphides can be used as sulphiding agents; however, only dimethyl disulphide has been explicitly mentioned as sulphiding agent, dimethyl disulphide moreover being the reference sulphiding agent in the industry to date.
  • EP 298 111 describes a process for the sulphidation of a catalyst by simultaneously passing hydrogen and a hydrocarbon feedstock comprising a sulphiding agent of formula RS n R′ (R and R′ being C 1 -C 4 alkyl radicals which can be identical or different, with n between 3 and 10).
  • WO 01/96499 describes the use as sulphiding agent of mixtures of disulphides resulting from an LPG (liquefied petroleum gas) desulphurization unit of an oil refining unit, the caustic and sodium compounds having been removed from these mixtures.
  • LPG liquefied petroleum gas
  • These mixtures of disulphides generally consist, to greater than 98%, of dimethyl disulphide, diethyl disulphide and ethyl methyl disulphide.
  • EP 0 976 726 describes a composition based on DMDS with a masked odour comprising up to 1% by weight of an odour-masking agent chosen from vanillin, ethyl vanillin and some esters. This masking is effective only if the content of impurities in the DMDS is limited, typically less than 500 ppm of methyl mercaptan, less than 1% of dimethyl sulphide.
  • alkyl polysulphides RS x R′ decompose at a lower temperature than alkyl disulphides, such as DMDS, which exhibits the advantage of making possible faster sulphidation of the catalysts, an advantage which the industry turns to good account.
  • alkyl polysulphides also well known in the industry, is the formation of solid sulphur and/or of a solid deposit which is generated during the heat treatment for activation of the catalyst; the solid sulphur and/or the solid deposit can be deposited in the various components of the refinery and thus create blockages which are very harmful to the operation of the industrial unit.
  • EP 130 850 describes a process for the ex situ presulphidation of a catalyst which consists in treating the said catalyst using at least one sulphiding agent of typical formula RS n R′ (R and R′ being C 1 -C 150 organic radicals (alkyl, naphthenic, aryl, alkylaryl, arylalkyl) which may be identical or different, with n between 3 and 20) used in solution in a solvent; the catalyst in the oxide form is impregnated with a solution of organic polysulphides (for example TPS 37 or TNPS, sold by Arkema), preferably in a hydrocarbon of white spirit type.
  • organic polysulphides for example TPS 37 or TNPS, sold by Arkema
  • This preliminary stage of incorporation in the catalyst of a sulphur compound of specific nature is completed by heat treatment of the catalyst in the absence of hydrogen at temperatures not exceeding 150° C.
  • This operation has the effect of removing the organic solvent and of ensuring the attachment of the sulphur to the catalyst via organic polysulphides.
  • the catalyst is stable in air and can be handled without specific precautions. It is supplied in this state to the user who, after charging to the hydrotreating reactor, can complete the sulphidation of the catalyst under hydrogen for the complete conversion of the metals to metal sulphides in the hydrotreating reactor in the presence of hydrogen.
  • the “ex situ” techniques currently developed on the industrial scale use, as sulphur-comprising products, organic polysulphides or sulphur.
  • the present invention relates to a novel sulphiding agent which has the advantage not only of decomposing at a lower temperature than dimethyl disulphide, regarded as the reference sulphiding agent of the industry, making possible more rapid sulphidation of the catalyst, but also of very significantly limiting solid deposits, in particular of sulphur, in comparison with polysulphides.
  • the sulphiding agent according to the invention consists essentially of diethyl disulphide (DEDS) or of dipropyl disulphide(s) (DPDS) or dibutyl disulphide(s) (DBDS); it exhibits the advantage of decomposing at a lower temperature than dimethyl disulphide but also of not forming a solid deposit, in particular related to sulphur, unlike polysulphides.
  • DEDS diethyl disulphide
  • DPDS dipropyl disulphide(s)
  • DBDS dibutyl disulphide(s)
  • the sulphiding agent consists essentially of DEDS.
  • the sulphiding agent consists essentially of DPDS.
  • the sulphiding agent consists essentially of DBDS.
  • the expression “consists essentially of” means comprises less than 20 000 ppm of impurities, preferably less than 10 000 ppm of impurities and advantageously less than 5000 ppm of impurities.
  • impurities is understood to mean traces of one or more sulphides which can be represented by the formula RS n R′ with n representing the mean sulphur value ranging from 1 to 10 and R and R′ representing H or a C 1 -C 24 linear or branched, aryl, cycloalkyl or alkyl chain, such as, for example, DMDS, dimethyl sulphide, methyl mercaptan, ethyl mercaptan, DPDS and/or DBDS when the sulphiding agent consists essentially of DEDS.
  • DPDS dipropyl disulphide(s)
  • DPDS dipropyl disulphide
  • dibutyl disulphide(s) are understood to mean the isomer or isomers of dipropyl disulphide and dibutyl disulphide respectively, for example n-propyl and/or isopropyl disulphide, n-, iso- and/or tert-butyl disulphide.
  • the sulphiding agent according to the invention additionally comprises at least one scenting base and/or one odour-masking agent chosen, for example, from the odour maskers, alone or as a mixture, described in EP 0 976 726, such as, in particular, vanillin, ethyl vanillin or esters of formula R 1 CO 2 R 2 in which R 1 represents a linear or branched hydrocarbon radical comprising from 1 to 4 carbon atoms which is optionally unsaturated and R 2 represents a linear, branched or cyclic hydrocarbon radical comprising from 2 to 8 carbon atoms which is optionally unsaturated.
  • one scenting base and/or one odour-masking agent chosen, for example, from the odour maskers, alone or as a mixture, described in EP 0 976 726, such as, in particular, vanillin, ethyl vanillin or esters of formula R 1 CO 2 R 2 in which R 1 represents a linear or branched hydrocarbon radical comprising from
  • the content of masking agent(s) and/or scenting base is less than or equal to 1% by weight of the total weight of the sulphiding agent, typically from 0.1 to 0.5% by weight.
  • the activity of the hydrotreating catalysts sulphided with a sulphiding agent according to the invention is significantly improved in comparison with the activity of the hydrotreating catalysts sulphided with DMDS.
  • the sulphiding agent according to the invention can in particular be used for the “in situ” presulphidation of the hydrotreating catalysts including a support based on at least one oxide of a metal or of a semimetal and at least one active metal; in this case, it can, for example, be introduced as a mixture with a gas oil, under a hydrogen pressure which can range from atmospheric pressure up to 20 MPa but is preferably between 1 and 5 MPa, the pressure range commonly used industrially.
  • This stage is carried out at a temperature which can range up to 350° C. (a higher temperature makes it possible to reduce the sulphiding time but very significantly increases the risk of coking).
  • a primary sulphidation carried out at a temperature ranging from 150 to 250° C., preferably from 210 to 230° C., so as to minimize the time necessary for the H 2 S breakthrough to be obtained in the outlet gases without risking a premature reduction, followed by
  • a secondary sulphidation carried out at a temperature ranging from 250 to 350° C., preferably from 290 to 330° C., and with a duration sufficient to have a constant concentration of H 2 S in the outlet gases.
  • the hydrogen blanket expressed by the ratio of the flow rate by volume of hydrogen in standard litres to the flow rate by volume of the gas oil in litres, is generally between 50 and 500 Sl/l, preferably between 100 and 300 Sl/l.
  • the hourly space velocity (HSV), defined as the ratio of the hourly flow by volume of gas oil to the volume of catalyst, can range from 0.1 to 5 h ⁇ 1 and is preferably between 1 and 3 h ⁇ 1 , a range commonly used industrially.
  • the total amount of sulphur introduced by the novel sulphiding agent of the invention can generally range from 100 to 250% of the weight of sulphur stoichiometrically required for the complete conversion to sulphides of the oxides of the catalyst.
  • the sulphiding agent according to the invention can also be used for an “ex situ” presulphidation.
  • the incorporation of the sulphur in the catalyst is carried out by bringing the catalyst into contact in the absence of hydrogen and makes it possible to obtain the expected degree of sulphidation with great accuracy.
  • This incorporation is generally carried out at a temperature of between 0 and 50° C., preferably between 0 and 30° C. and advantageously at ambient temperature.
  • the sulphiding agent is generally employed diluted in an appropriate solvent which depends in particular on the nature of the sulphiding agent.
  • the solvent can be chosen from the following solvents, alone or as a mixture:
  • Example 3 shows the improvement in the activity of the hydrotreating catalysts by sulphidation with DEDS to which a scenting base has been added in comparison with sulphidation with DMDS to which the same scenting base has been added.
  • a non-desulphurized gas oil of SRGO (Straight Run Gas Oil) type has added to it 0.8% of sulphur contributed by a sulphiding agent, either DMDS or DEDS.
  • the additivated gas oil is subsequently introduced at ambient temperature with a flow rate of 80 cm 3 /h under a hydrogen flow rate of 20 l/h. Subsequently, the temperature of the oven is adjusted in order to reach 150° C. in the catalyst bed.
  • the gas oil flow rate and the hydrogen flow rate remain fixed respectively at 80 cm 3 /h and 20 l/h.
  • the gaseous effluents at the reactor outlet are analysed by chromatography in order to monitor the change in the H 2 S concentration representative of the decomposition of the sulphiding agent.
  • a pipe made of Incolloy 800HT with a length of 30 cm and a diameter of 7.7 cm is placed in an oven in order to vary the temperature inside the pipe between 200 and 400° C.
  • a sulphiding agent is introduced into the pipe as a mixture with nitrogen in order to have a sulphur injection flow rate of 0.8 g of sulphur/h and a nitrogen flow rate of 4 l/h. The sulphiding agent is thus introduced for 3 hours.
  • the effluents at the outlet of the pipe are condensed and recovered. After injecting for 3 hours, the condensates recovered are filtered and, if appropriate, the solid recovered is weighed.
  • the various sulphiding agents tested are DMDS, DEDS, DPDS, DBDS and a di(tert-butyl)polysulphide sold by Arkema under the name TPS54.
  • An activity test was carried out on a pilot-scale hydrotreating plant in order to compare the activity of DMDS to which 3000 ppm of an odour-masking agent have been added with that of DEDS to which 3000 ppm of the same masking agent have been added.
  • This pilot-scale plant represents an industrial hydrotreating unit.
  • the reactor is charged with a commercial catalyst of Nickel Molybdenum (NiMo) type supported on alumina.
  • the reactor has a volume of 300 ml, a diameter of 17.4 mm and a height of 1300 mm.
  • the catalyst is charged between two layers of carborundum, an inert silicon carbide material, ensuring better distribution of the fluids.
  • the volume of catalyst charged is 20 ml.
  • the sulphidation feedstock used is a gas oil resulting from the atmospheric distillation of crude oil (Straight Run Gas Oil: SRGO) to which 1% of sulphur coming from the sulphiding agent has been added.
  • SRGO Heavy Run Gas Oil
  • DMDS and DEDS do not have the same sulphur content, this procedure makes it possible to compare comparable aspects.
  • the sulphidation was carried out under a pressure of 4.5 MPa, an hourly space velocity (HSV) of 1 h ⁇ 1 and an H 2 /hydrocarbon (HC) ratio of 200 Sl/l in the following way:
  • test feedstock used is a mixture of Straight Run Gas Oil (SRGO) and of Light Crude Oil (LCO) in a 70/30 ratio having a total sulphur content of 10 400 ppm.
  • SRGO Straight Run Gas Oil
  • LCO Light Crude Oil
  • the desulphurization test is subsequently carried out at different temperatures (340° C., 350° C. and 360° C.) with periods of stabilization in order to determine the effectiveness of the sulphided catalyst.
  • the total sulphur content in the feedstock after passing through the hydrotreating reactor is determined continuously during the desulphurization test.
  • the odour-masking agent has the following composition by weight: isoamyl acetate (25%). diethyl orthophthalate (50%), 2-methylbutyl butyrate (15%) and benzyl acetate (10%).
  • the additivated DEDS makes it possible to obtain the same level of desulphurization (10 ppm) as the additivated DMDS but with 5° C. less (353° C. instead of 358° C.). which is highly significant for a hydrotreating unit.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US11/961,164 2006-12-22 2007-12-20 Hydrotreating catalyst sulphiding agent and its use for in situ and ex situ presulphidation Abandoned US20080312074A1 (en)

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Application Number Priority Date Filing Date Title
US11/961,164 US20080312074A1 (en) 2006-12-22 2007-12-20 Hydrotreating catalyst sulphiding agent and its use for in situ and ex situ presulphidation
US12/858,647 US9353054B2 (en) 2006-12-22 2010-08-18 Hydrotreating catalyst sulphiding agent and its use for in situ and ex situ presulphidation

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
FR0655884A FR2910349A1 (fr) 2006-12-22 2006-12-22 Agent de sulfuration de catalyseur d'hydrotraitement et son utilisation pour la sulfuration in-situ et ex-situ
FR06.55884 2006-12-22
US93915207P 2007-05-21 2007-05-21
FR0757330A FR2910348B1 (fr) 2006-12-22 2007-09-03 Agent de sulfuration de catalyseur d'hydrotraitement et son utilisation pour la presulfuration in-situ et ex-situ
FR07.57330 2007-09-03
US11/961,164 US20080312074A1 (en) 2006-12-22 2007-12-20 Hydrotreating catalyst sulphiding agent and its use for in situ and ex situ presulphidation

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US (2) US20080312074A1 (fr)
EP (1) EP2094386B1 (fr)
JP (1) JP5218422B2 (fr)
CA (1) CA2672615C (fr)
ES (1) ES2715047T3 (fr)
FR (1) FR2910348B1 (fr)
PL (1) PL2094386T3 (fr)
TR (1) TR201903476T4 (fr)
WO (1) WO2008087330A2 (fr)

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EP3371145B1 (fr) 2015-11-06 2023-07-19 Uop Llc Utilisation d'un absorbeur de c4 pour la réextraction d'aldéhydes

Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993938A (en) * 1958-06-18 1961-07-25 Universal Oil Prod Co Hydroisomerization process
US3016347A (en) * 1959-09-21 1962-01-09 Universal Oil Prod Co Hydrocarbon purification process and catalyst
US3140994A (en) * 1961-07-12 1964-07-14 Socony Mobil Oil Co Inc Method of reducing nitrogen to not more than 1 p. p. m. in reformer feed
US3527839A (en) * 1969-01-13 1970-09-08 Shell Oil Co Ethylene oligomerization
US3530200A (en) * 1969-01-13 1970-09-22 Shell Oil Co Ethylene oligomerization
US3732155A (en) * 1971-03-31 1973-05-08 Exxon Research Engineering Co Two-stage hydrodesulfurization process with hydrogen addition in the first stage
US4098682A (en) * 1976-06-18 1978-07-04 Uop Inc. Hydrodesulfurization catalyst and method of preparation
US4132632A (en) * 1978-03-31 1979-01-02 Standard Oil Company (Indiana) Selective hydrodesulfurization of cracked naphtha
US4172027A (en) * 1977-01-31 1979-10-23 Institut Francais Du Petrole Catalytic process for reforming or production of aromatic hydrocarbons
US4176087A (en) * 1977-06-20 1979-11-27 Conoco Methanation Company Method for activating a hydrodesulfurization catalyst
US4334982A (en) * 1979-05-21 1982-06-15 Institut Francais Du Petrole Process for the selective desulfurization of olefinic cuts
US4397739A (en) * 1980-02-19 1983-08-09 Institut Francais Du Petrole Process for desulfurizing a catalytic cracking or steam cracking effluent
US4725569A (en) * 1984-11-27 1988-02-16 Tuszynski William J Organopolysulfide-impregnated catalyst and methods of preparation and use
US4725571A (en) * 1987-01-23 1988-02-16 Tuszynski William J Presulfiding composition for preparing hydrotreating catalyst activity and process for presulfiding a hydrotreating catalyst
US4983558A (en) * 1988-02-16 1991-01-08 Institut Francais Du Petrole Process for presulfurizing a hydrocarbon treatment catalyst
US5820749A (en) * 1996-11-22 1998-10-13 Exxon Chemical Patents, Inc. Hydrogenation process for unsaturated hydrocarbons
US6639110B2 (en) * 1998-07-31 2003-10-28 Elf Atochem, S.A. Method for making dimethyl disulphide compositions having a masked smell

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1049396A (fr) 1953-06-24 1953-12-29 Cfcmug Compteur de gaz de type sec à coquilles
GB1309457A (en) 1970-06-16 1973-03-14 Universal Oil Prod Co Method of activating hydrocracking catalysts
FR2503733B1 (fr) 1981-04-09 1985-09-06 Inst Francais Du Petrole Procede d'hydrotraitement d'une charge hydrocarbonee en presence d'un catalyseur soumis a une presulfuration
FR2548205B1 (fr) * 1983-06-30 1985-11-29 Eurecat Europ Retrait Catalys Procede de presulfuration de catalyseur de traitement d'hydrocarbures
FR2609650B1 (fr) * 1987-01-20 1993-05-07 Elf Aquitaine Sulfuration de catalyseurs d'hydroraffinage
FR2627104B1 (fr) 1988-02-16 1990-07-20 Inst Francais Du Petrole Procede de presulfuration de catalyseur de traitement d'hydrocarbures
US4937385A (en) * 1988-05-18 1990-06-26 Pennwalt Corporation Process for the manufacture of dialkyl disulfides and polysulfides
JPH03138059A (ja) 1989-10-24 1991-06-12 Nippon Steel Corp 連続鋳造の拘束性ブレークアウト予知方法
JPH04150945A (ja) * 1990-10-15 1992-05-25 Mitsui Toatsu Chem Inc 脱臭用酸化物固体触媒
JP3138059B2 (ja) * 1992-05-27 2001-02-26 花王株式会社 水性組成物
JP4338254B2 (ja) * 1999-03-17 2009-10-07 新日本石油株式会社 重質油の水素化処理方法
US6362374B1 (en) * 2000-05-01 2002-03-26 The Lubrizol Corporation Composition of and method for polysulfides having a reduced odor level
WO2001096499A1 (fr) 2000-06-10 2001-12-20 Sk Corporation Procede d'utilisation d'un melange de disulfure en tant qu'agent de sulfuration
FR2820991B1 (fr) * 2001-02-22 2003-10-03 Atofina Procede de sulfuration des catalyseurs d'hydrotraitement

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993938A (en) * 1958-06-18 1961-07-25 Universal Oil Prod Co Hydroisomerization process
US3016347A (en) * 1959-09-21 1962-01-09 Universal Oil Prod Co Hydrocarbon purification process and catalyst
US3140994A (en) * 1961-07-12 1964-07-14 Socony Mobil Oil Co Inc Method of reducing nitrogen to not more than 1 p. p. m. in reformer feed
US3527839A (en) * 1969-01-13 1970-09-08 Shell Oil Co Ethylene oligomerization
US3530200A (en) * 1969-01-13 1970-09-22 Shell Oil Co Ethylene oligomerization
US3732155A (en) * 1971-03-31 1973-05-08 Exxon Research Engineering Co Two-stage hydrodesulfurization process with hydrogen addition in the first stage
US4098682A (en) * 1976-06-18 1978-07-04 Uop Inc. Hydrodesulfurization catalyst and method of preparation
US4172027A (en) * 1977-01-31 1979-10-23 Institut Francais Du Petrole Catalytic process for reforming or production of aromatic hydrocarbons
US4176087A (en) * 1977-06-20 1979-11-27 Conoco Methanation Company Method for activating a hydrodesulfurization catalyst
US4132632A (en) * 1978-03-31 1979-01-02 Standard Oil Company (Indiana) Selective hydrodesulfurization of cracked naphtha
US4334982A (en) * 1979-05-21 1982-06-15 Institut Francais Du Petrole Process for the selective desulfurization of olefinic cuts
US4397739A (en) * 1980-02-19 1983-08-09 Institut Francais Du Petrole Process for desulfurizing a catalytic cracking or steam cracking effluent
US4725569A (en) * 1984-11-27 1988-02-16 Tuszynski William J Organopolysulfide-impregnated catalyst and methods of preparation and use
US4725571A (en) * 1987-01-23 1988-02-16 Tuszynski William J Presulfiding composition for preparing hydrotreating catalyst activity and process for presulfiding a hydrotreating catalyst
US4983558A (en) * 1988-02-16 1991-01-08 Institut Francais Du Petrole Process for presulfurizing a hydrocarbon treatment catalyst
US5820749A (en) * 1996-11-22 1998-10-13 Exxon Chemical Patents, Inc. Hydrogenation process for unsaturated hydrocarbons
US6639110B2 (en) * 1998-07-31 2003-10-28 Elf Atochem, S.A. Method for making dimethyl disulphide compositions having a masked smell
US6743951B2 (en) * 1998-07-31 2004-06-01 Elf Atochem S.A. Compositions based on dimethyl disulphide with a masked smell

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WO2008087330A2 (fr) 2008-07-24
TR201903476T4 (tr) 2019-04-22
WO2008087330A3 (fr) 2008-09-12
EP2094386A2 (fr) 2009-09-02
US9353054B2 (en) 2016-05-31
PL2094386T3 (pl) 2019-07-31
EP2094386B1 (fr) 2019-01-30
ES2715047T3 (es) 2019-05-31
FR2910348A1 (fr) 2008-06-27
US20110005974A1 (en) 2011-01-13
JP5218422B2 (ja) 2013-06-26
FR2910348B1 (fr) 2012-05-18
CA2672615A1 (fr) 2008-07-24
JP2010513011A (ja) 2010-04-30

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