WO2019093890A1 - Procédé pour la préparation d'une composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes, composition de piégeur destinée à être utilisée dans ledit procédé et composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes ainsi préparée - Google Patents

Procédé pour la préparation d'une composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes, composition de piégeur destinée à être utilisée dans ledit procédé et composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes ainsi préparée Download PDF

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WO2019093890A1
WO2019093890A1 PCT/NL2018/050746 NL2018050746W WO2019093890A1 WO 2019093890 A1 WO2019093890 A1 WO 2019093890A1 NL 2018050746 W NL2018050746 W NL 2018050746W WO 2019093890 A1 WO2019093890 A1 WO 2019093890A1
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hydrocarbon liquid
liquid composition
composition
vol
ppm
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Gijsbertus Cornelis Spruijt
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Wrt BV
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Wrt BV
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Priority claimed from NL2019890A external-priority patent/NL2019890B1/en
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Priority to EP18845451.6A priority Critical patent/EP3707222A1/fr
Publication of WO2019093890A1 publication Critical patent/WO2019093890A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/06—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of alkaline solutions
    • 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
    • C10G19/00—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment
    • C10G19/02—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment with aqueous alkaline solutions
    • 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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/10—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of metal-containing organic complexes, e.g. chelates, or cationic ion-exchange resins
    • 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
    • C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
    • C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
    • C10G53/12—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one alkaline treatment step
    • 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
    • C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
    • C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
    • C10G53/14—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one oxidation step

Definitions

  • the present invention relates to a process for preparing sweetened hydrocarbon liquid compositions with an olefin content of 5 vol.% or more with reduced gum formation, to the product so obtained and to the scavenger composition which may be used in the process.
  • shale oil which is a synthetic crude oil produced by retorting oil shale.
  • Oil shale is an organic-rich fine-grained sedimentary rock containing kerogen (a solid mixture of organic chemical compounds).
  • shale oils are: (1 ) high levels of olefins and diolefins -which are not present in petroleum crudes- requiring special care during processing due to their tendency to polymerize and form gums; (2) high levels of aromatic compounds, deleterious to kerosene and diesel cuts; (3) high carbon/hydrogen ratio; (4) low sulfur levels, compared with most crudes available in the world (though for some shale oils from the retorting of marine oil shale, high sulfur compounds are present); (5) suspended solids (finely divided rock) which cause process problems chiefly if a first step of processing is hydrotreating; (6) moderate levels of metals.
  • the hydrocarbons making up shale oil can be classified as being about 20 vol.% alkanes, 20 vol.% aromatics, 25 vol.% aromatic resins, and 35 vol.% olefins and naphthenes.
  • a typical crude would contain about 15 vol.% alkanes, 50 vol.% aromatics, and 35 vol.% naphthenes with hardly any olefins or resins.
  • shale oil may be distinguished from typical petroleum crudes by their content of olefins constituting (significantly) more than 5 vol.% of the make-up. Estonian shale oil tends to have an olefin content of more than 50 vol.%.
  • a process that may be used to upgrade shale oil is the removal of mercaptans by catalytic oxidation (so-called MEROX process, also known as “sweetening”) as discussed hereafter.
  • MEROX process catalytic oxidation
  • sweetening results in an increased tendency of gum formation of the so produced sweetened shale oil.
  • Mr. Gue a particular problem with shale oil concerns gum formation. This problem has been described also by Fathoni, A. Z.; Batts, B. D. A literature review of fuel stability studies with a particular emphasis on shale oil. Energy Fuels 1992, 6, 681 -693, and G. U. Dinneen, W. D. Bickel,. Ind. Eng. Chem. , 1951 , 43 (7), pp 1604-1607.
  • Gum formation is part of a larger problem concerning storage and thermal stability.
  • Storage stability concerns the ability of a hydrocarbon liquid composition, stored over extended periods of time, to remain unchanged or without appreciable deterioration under ambient conditions.
  • Thermal stability concerns the ability of the hydrocarbon liquid composition to suffer relatively high-temperature stress for short periods of time, without appreciable deterioration. Such changes or degradations include color change, development of soluble and/or insoluble gum, development of particulate matter followed by sediment/deposit, development of coke and fouling materials, change in global physicochemical properties, and other undesired effects.
  • Gums in case the hydrocarbon liquid composition is used as fuel, may stick to metal surfaces along a vehicle-fuel system, from the tank to the
  • Shale oil in particular the Estonian shale oil, suffers from rapid formation of gums which problem is actually amplified upon catalytic oxidative removal of mercaptans, such as in the MEROX reaction.
  • Mercaptan is the generic name for a family of organic compounds where sulfur and a hydrogen atom (SH) are bonded to one of the carbon atoms in the molecule.
  • the hydrogen atom in the SH radical can ionize and produce a mildly acidic environment, which may lead to corrosion.
  • the most noticeable characteristic of mercaptan is their strong, unpleasant odor even when their concentration is only a few parts per million.
  • Processes within oil refineries or natural gas processing plants that remove mercaptans and/or hydrogen sulfide (H2S) are commonly referred to as sweetening processes because they results in products which no longer have the sour, foul odors of mercaptans and hydrogen sulfide.
  • the liquid hydrocarbon disulfides may remain in the sweetened products, they may be used as part of the refinery or natural gas processing plant fuel, or they may be processed further.
  • Merox is an acronym for mercaptan oxidation. It is a catalytic chemical process developed by UOP and used in oil refineries and natural gas processing plants to remove mercaptans from LPG, propane, butanes, light naphthas, kerosene and jet fuel by converting them to liquid hydrocarbon disulfides.
  • the Merox process requires an alkaline environment which, in some process versions, is provided by an aqueous solution of sodium hydroxide (NaOH), a strong base, commonly referred to as caustic.
  • NaOH sodium hydroxide
  • the alkalinity is provided by ammonia, which is a weak base.
  • ammonia which is a weak base.
  • the Merox process is for instance disclosed in GB1240727. This specific document concerns the loss of catalyst.
  • this specific document concerns the loss of catalyst.
  • it describes the sweetening of a sour organic stream, whereby the latter is contacted in an oxidation zone with an oxidizing agent and with an alkaline solution of a phthalocyanine catalyst to convert at least a portion of any mercaptan component present in it to disulphide.
  • the effluent from the oxidation (sweetening) zone is then passed to a separation zone from which separated, sweetened organic phase and separated alkaline phase containing pthalocyanine catalyst are withdrawn, while liquid phthalocyanine catalyst complex is withdrawn from the interfacial zone between said phases and admixed with withdrawn alkaline phase thereby increasing the concentration of catalyst therein before recycling the same to the oxidation zone.
  • commercial light naphtha having a mercaptan sulfur content of 150 to 200 ppm by weight is contacted in a sweetening zone with air and a caustic alkali solution containing 125 ppm by weight of cobalt phthalocyanine sulfonate.
  • the effluent from the sweetening zone was passed to a separate zone from which an organic phase was withdrawn and found to be sweet to the doctor test.
  • the invention provides a process for preparing a sweetened hydrocarbon liquid composition with reduced tendency to form gums from a sour hydrocarbon liquid
  • composition containing mercaptans and with an olefin content of 5 vol.% or more by reacting the mercaptans in the sour hydrocarbon liquid composition into disulfides with an oxidizing agent in the presence of a scavenger composition comprising a cobalt complex as catalyst and a strong base, wherein the strong base consists of KOH.
  • a scavenger composition comprising the catalyst and the base that may be used in the process of the invention, and a sweetened hydrocarbon liquid composition with reduced tendency to form gums. The latter is of particular importance as it allows the use of said sweetened hydrocarbon liquid compositions as fuel or as part of a blend that is used as fuel.
  • the expression "reduced tendency to form gums”, is relative to the same process using NaOH as base in the same reaction. It is preferred to keep unwashed gum, pursuant to ASTM D381 at less than 120, preferably less than 100 mg/100ml. More preferably, the unwashed gum is not increased vis-a-vis the sour hydrocarbon liquid composition by more than 50%, more preferably still, not increased at all. Ideally, the tendency to form gums , pursant to ASTM D381 , is less than 30 mg/ml, which may require blending the sour or sweetened hydrocarbon liquid composition with another hydrocarbon liquid composition that is already low in the tendency to form gums.
  • the Merox process is known from many art references. For instance, in both US2921021 and GB1240727 said process is described for petroleum distillates. It involves treating a sour hydrocarbon liquid composition with an oxidizing agent, generally air, in the presence of a catalyst and a strong base.
  • an oxidizing agent generally air
  • the sour hydrocarbon liquid composition may be treated at ambient to elevated temperatures, e.g., from 5 to 200°C, typically from 10 to 50°C. Atmospheric pressure can be employed, although super-atmospheric pressure up to 70 MPa, e.g., up to 5 MPa may be used, if desired.
  • the time of contact of the sour hydrocarbon liquid composition with the oxidizing agent and the scavenger composition containing the catalyst and strong base is generally set to achieve the desired reduction in mercaptan level and may range from 1 minute to 5 days or more. This also depends on the amount of catalyst used.
  • the catalyst may be used in a range of 1 to 15, preferably 5 to 10 ppm of catalyst by weight to 1 ppm of mercaptan and hbS (as S) by weight.
  • the duration of the treatment at ambient temperature and atmospheric pressure may last from 6 hours to 3 days.
  • the ratio for shale oil tends to be higher than the common ratio used for petroleum cuts, as shale oil tends to comprise more "heavy" mercaptans than found in petroleum cuts.
  • hydrocarbon liquid composition with a reduced tendency to form gums, despite the high initial olefin content.
  • the present invention results in a new shale oil-based fuel composition with reduced tendency to form gums.
  • Scavenger compositions for use in Merox processes are known.
  • the present composition comprising cobalt(phthalocyanine) and KOH dissolved in ethanol, preferably at a
  • Lower amounts of KOH may be used, but this affects the efficiency of the scavenger composition during the conversion of the mercaptans to disulfides.
  • Higher amounts of KOH may be used, but may run into solubility issues.
  • the scavenger composition of the present invention is believed to be novel. Also the use of the scavenger composition for sweetening sour hydrocarbon compositions with the specific aim to reduce the tendency of gum formation is believed to be novel, and therefore claimed.
  • the process is particularly suitable for shale oil, with an olefin content that is 40 vol.% or higher, even 50 vol.% or higher.
  • a sour hydrocarbon liquid composition with a high olefin content is the preferred embodiment of the present invention.
  • the present process may also be used for sour hydrocarbon liquid compositions with a lower content of olefins, or blends with a lower content of olefins.
  • a caustic solution such as sodium hydroxide or potassium hydroxide
  • the caustic solution is also helpful in that it removes naphthenic acids and other organic acids in general such as phenolic acids, and other sulfur compounds from refined petroleum products and petroleum distillate.
  • Various processes for regenerating the caustic solutions and apparatus for same are disclosed in the prior art. For example, U.S. Pat. Nos. 8,597,501 and 7,326,333 disclose such exemplary processes and apparatus. In various documents processes and equipment are described that allow the regeneration of the caustic streams.
  • the sour hydrocarbon liquid composition containing mercaptans and with an olefin content of 5 vol.% or more prior to the MEROX reaction is first subjected to a caustic wash. Moreover, it has been found that if said caustic wash is performed using KOH, rather than NaOH or ammonia and the like, the tendency of gum formation is even further reduced.
  • a synergy has been found, when subjecting a sour hydrocarbon liquid composition containing mercaptans and with an olefin content of 5 vol.% or more first to a caustic wash using KOH, and then reacting the mercaptans in said sour hydrocarbon liquid composition into disulfides with an oxidizing agent in the presence of a scavenger composition comprising a cobalt complex as catalyst and a strong base, wherein the strong base consists of KOH.
  • the washing may be carried out by mixing the sour hydrocarbon liquid composition with a 50% (w/w) potassium hydroxide solution, allowing the mixture to settle, and removing the caustic solution.
  • the 50% solution is used in an amount of 5% by weight vis-a-vis the sour hydrocarbon liquid composition.
  • greater and smaller amounts may be used, as well as caustic solutions that are greater or lower in concentration.
  • a simple wash step typically will reduce the content of hydrogen sulfide and mercaptans by 90% or more.
  • reaction is monitored and analysed at 6 or 12 hour intervals. (Analysis is stopped if the desired reduction of the mercaptan level has been achieved.)
  • shale oil-based gasoline from Eesti Energia, the Estonian state-owned company, internationally known as Enefit. Products from different units were used, Enefit-140 and Enefit-280.
  • shale-oil is a product from nature, the composition varies. Generally, it has an olefin content of at least 50 vol.%.
  • the shale oil- based gasoline used in Examples 1-3 were first washed with an NaOH solution.
  • Comparative experiments 1-4 and experiment 5 were carried out with a batch of Enefit-280 with an H2S value (as S) of 184 ppm, a mercaptan content (as S) of 1331 ppm, and a washed gum content of 46,6 mg/100ml. It was treated for 48 hrs with 4 commercial scavenger compositions (I to IV) and the scavenger composition according to the present invention (A). Only the scavenger composition according to the present invention contained KOH as base. The dosage was 1 :5 (5 ppm of catalyst to 1 ppm mercaptans). The result of the tests are illustrated in Table 1. Table 1
  • inventive scavenger composition clearly outperforms commercial scavenger compositions when used to sweeten a sour hydrocarbon liquid composition based on shale oil (and thus containing more than 5 vol.% olefins).
  • inventive scavenger composition clearly outperforms a comparable scavenger composition that employs NaOH as base when used to sweeten a sour hydrocarbon liquid composition based on shale oil (and thus containing more than 5 vol.% olefins).
  • NaOH increases the tendency of gum formation, as is seen when the ratio is increased
  • KOH actually and surprisingly reduces the tendency of gum formation (at least vis-a-vis scavenger compositions based on NaOH).
  • inventive scavenger composition clearly outperforms a comparable scavenger composition that employs NaOH as base when used to sweeten a sour hydrocarbon liquid composition based on shale oil (and thus containing more than 5 vol.% olefins).
  • the tendency of gum formation of the sweetened hydrocarbon composition using scavenger composition A, using KOH as base is significantly less. This reduction in gum formation, when substituting NaOH by KOH, is entirely unexpected. This effect is not seen with any other (organic or inorganic) base either.
  • Example 4 Experiments similar to those in Examples 1-3 were performed, now using shale oil-based gasoline first washed with a a 50% KOH solution. This led to a further reduction in gum formation.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention concerne un procédé pour la préparation d'une composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes à partir d'une composition liquide d'hydrocarbures acide contenant des mercaptans et ayant une teneur en oléfines supérieure ou égale à 5 % en volume, par réaction des mercaptans présents dans la composition liquide d'hydrocarbures acide en disulfures avec un agent oxydant en présence d'une composition de piégeur comprenant un complexe de cobalt en tant que catalyseur et une base forte, la base forte étant constituée de KOH. L'invention concerne également une composition de piégeur comprenant le catalyseur et la base qui peut être utilisée dans le procédé selon l'invention et une composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes.
PCT/NL2018/050746 2017-11-10 2018-11-09 Procédé pour la préparation d'une composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes, composition de piégeur destinée à être utilisée dans ledit procédé et composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes ainsi préparée Ceased WO2019093890A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP18845451.6A EP3707222A1 (fr) 2017-11-10 2018-11-09 Procédé pour la préparation d'une composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes, composition de piégeur destinée à être utilisée dans ledit procédé et composition liquide d'hydrocarbures adoucie présentant une tendance réduite à former des gommes ainsi préparée

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
NL2019890 2017-11-10
NL2019890A NL2019890B1 (en) 2017-11-10 2017-11-10 Process for preparing a sweetened hydrocarbon liquid composition with reduced tendency to form gums, a scavenger composition for use in said process, and the sweetened hydrocarbon liquid composition with reduced tendency to form gums so prepared.
NL2020504 2018-02-28
NL2020504A NL2020504B1 (en) 2017-11-10 2018-02-28 Process for preparing a sweetened hydrocarbon liquid composition with reduced tendency to form gums, a scavenger composition for use in said process, and the sweetened hydrocarbon liquid composition with reduced tendency to form gums so prepared.

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WO2019093890A1 true WO2019093890A1 (fr) 2019-05-16

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2616833A (en) * 1951-03-01 1952-11-04 Universal Oil Prod Co Treatment of hydrocarbon distillates
US2640012A (en) * 1951-10-10 1953-05-26 Universal Oil Prod Co Treatment of cracked hydrocarbon distillates
US2921021A (en) 1957-12-18 1960-01-12 Universal Oil Prod Co Treatment of sour hydrocarbon distillate
GB1184166A (en) * 1967-04-20 1970-03-11 Universal Oil Prod Co Treatment of Color-Degradable Sour Hydrocarbon Distillates
GB1240727A (en) 1968-12-02 1971-07-28 Universal Oil Prod Co Process for oxidising mercapto compounds
US4260479A (en) * 1979-09-27 1981-04-07 Uop Inc. Catalytic oxidation of mercaptan in sour petroleum distillate
US4392947A (en) * 1981-09-30 1983-07-12 Mobil Oil Corporation Integrated refining process
US4753722A (en) * 1986-06-17 1988-06-28 Merichem Company Treatment of mercaptan-containing streams utilizing nitrogen based promoters
US7326333B2 (en) 2001-12-20 2008-02-05 Uop Llc Apparatus and process for extracting sulfur compounds from a hydrocarbon stream
US20110127194A1 (en) * 2009-11-30 2011-06-02 Merichem Company Hydrocarbon Treatment Process
US8597501B2 (en) 2010-06-30 2013-12-03 Uop Llc Process for removing one or more sulfur compounds from a stream

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2616833A (en) * 1951-03-01 1952-11-04 Universal Oil Prod Co Treatment of hydrocarbon distillates
US2640012A (en) * 1951-10-10 1953-05-26 Universal Oil Prod Co Treatment of cracked hydrocarbon distillates
US2921021A (en) 1957-12-18 1960-01-12 Universal Oil Prod Co Treatment of sour hydrocarbon distillate
GB1184166A (en) * 1967-04-20 1970-03-11 Universal Oil Prod Co Treatment of Color-Degradable Sour Hydrocarbon Distillates
GB1240727A (en) 1968-12-02 1971-07-28 Universal Oil Prod Co Process for oxidising mercapto compounds
US4260479A (en) * 1979-09-27 1981-04-07 Uop Inc. Catalytic oxidation of mercaptan in sour petroleum distillate
US4392947A (en) * 1981-09-30 1983-07-12 Mobil Oil Corporation Integrated refining process
US4753722A (en) * 1986-06-17 1988-06-28 Merichem Company Treatment of mercaptan-containing streams utilizing nitrogen based promoters
US7326333B2 (en) 2001-12-20 2008-02-05 Uop Llc Apparatus and process for extracting sulfur compounds from a hydrocarbon stream
US20110127194A1 (en) * 2009-11-30 2011-06-02 Merichem Company Hydrocarbon Treatment Process
US8597501B2 (en) 2010-06-30 2013-12-03 Uop Llc Process for removing one or more sulfur compounds from a stream

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
FATHONI, A. Z.; BATTS, B. D.: "A literature review of fuel stability studies with a particular emphasis on shale oil", ENERGY FUELS, vol. 6, 1992, pages 681 - 693
G. U. DINNEEN; W. D. BICKEL, IND. ENG. CHEM., vol. 43, no. 7, 1951, pages 1604 - 1607

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