US3316318A - Process for recovery of aromatics from cracked gasoline fractions - Google Patents

Process for recovery of aromatics from cracked gasoline fractions Download PDF

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US3316318A
US3316318A US178615A US17861562A US3316318A US 3316318 A US3316318 A US 3316318A US 178615 A US178615 A US 178615A US 17861562 A US17861562 A US 17861562A US 3316318 A US3316318 A US 3316318A
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column
extraction
benzene
solvent
gasoline
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Voetter Heinz
Ridderikhoff Werner
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Shell USA Inc
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Shell Oil Co
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    • 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
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
    • C10G67/0409—Extraction of unsaturated hydrocarbons
    • C10G67/0427—The hydrotreatment being a selective hydrogenation of diolefins or acetylenes
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/30—Aromatics

Definitions

  • the invention relates to a process for recovering aromatic hydrocarbons in a pure, or almost pure, state from a hydrocarbon mixture containing alkenes and more highly unsaturated compounds in addition to aromatic compounds.
  • the invention therefore relates to aA process for the .recovery of aromatic hydrocarbons in a pure, or almost pure, state by hydrogenating and subsequently extracting a hydrocarbon mixture containing alkenes and more highly unsaturated compounds in addition to aromatic compounds.
  • the process is characterized in that the hydrocarbon mixture is subjected to a selective hydrogenation, wherein the more highly unsaturated compounds are hydrogenated, and the selectively hydrogenated product is then subjected to extraction.
  • lBy selective hydrogenation it is meant a hyd-rogenation by which preferably 95% or more of the more highly unsaturated compounds are hydrogenated, while less than 25% and preferably less than :15% of the alkenes originally present or formed from the more highly unsaturated compounds Iare converted into saturated compounds.
  • the present invention is advantageous in that not only is considerable hydrogen saved, but also in that by extraction of the selectively hydrogenated product, a rainate phase is obtained .that contains most of the Ialkenes present in the base material as well as: any alkenes formed from the more highly unsaturated compounds during the selective hydrogenation. These alkenes in the raffinate phase constitute valuable gasoline components owing to their relatively high octane number. Moreover, the rallinate is more stable since little or no alkadienes are contained therein.
  • Starting materials suitable for the present process are hydrocarbon mixtures con-taining, in addition to aromatic compounds, alkenes and more highly unsaturated cornpounds, such as alkynes and alkadienes, either in a cyclic structure or not.
  • particularly suitable starting materials lare the hydrocarbon mixtures having a tinal boiling point of not more than 375 C. (ASTM) which are produced by thermal and/ or catalytic cracking.
  • gasolines or fractions thereof obtained by thermal cracking hydrocarbons in the presence of steam and/or oxygen are particularly suitable starting materials.
  • These gasolines are of a special nature in that they have a relatively very high content of highly unsaturated hydrocarbons and a high percentage of valuable aromatic compounds iand alkenes.
  • Thermal cracking in the presence of steam is preferably conducted with aliphatic hydrocarbon oils having a final boiling point of not more than 230 C.
  • Steam cracking is generally carried out at temperatures between about 550 C. and about 900 C., preferably between 750 C. and 800 C. and preferably under a pressure below about 5 atm. abs.
  • the amount of steam applied is generally 0.110 parts by weight, preferably about one part by weight to one part by weight of starting material.
  • This steam cracking is applied mainly for preparing lower alkenes, in particular ethene and propene, which are used as base materials in the chemical industry. During the cracking treatment usually more than 50% W. of the hydrocarbon oil used as starting material is converted into compounds with four or fewer carbon atoms in the molecule.
  • Gasoline produced as la byproduct of the steam cracking process as a rule contains more than 30% w. and often more than ⁇ 60% W. of aromatic compounds.
  • the gasoline contains a considerable amount of alkenes as well as more highly unsaturated compounds, mainly dienes, such as the cyclopentadiene type.
  • dienes such as the cyclopentadiene type.
  • a fur-ther ⁇ advantage is that these gasolines are generally practically free of sulfur.
  • tha-t is to say, less than 0.1% w. (calculated as elemental sulfur).
  • the selective hydrogenation is carried out in the presence of free hydrogen and .in the presence of one or more catalysts known for this purpose.
  • catalysts contain, for ins-tance, one or more metals of Group VIII of lthe periodic system of elements.
  • Particularly selective catalysts are nickel and/ or cobalt, supported on a carrier containing one or more water-insoluble salts of alkalineearth metals, such as waterinsoluble alkaline-earth metal sulfates, eg., barium sulfate.
  • Other selective catalysts for .this purpose are suliided nickel and sulded platinum, either as such or supported on a carrier.
  • the selective hydrogenation ⁇ is preferably carried out in such a manner that the hydrocarbon mixture is, at least partially, present in the liquid Iphase, and is generally effected at average catalyst temperatures of not more than C.
  • the treatment is carried out at average catalyst temperatures between 70 C. and 130 C.
  • the amount of iydrogen employed is at least equal to the theoretical imount required for the complete conversion into alkenes 3f the dienes and other highly unsaturated compounds )resent in the starting mixture.
  • the theoretical amount of hydrogen is used. Owing to this excess of hydrogen, the catalyst activity is generally maintained for a longer period, without, however, leading to further hydrogenation of the alkenes.
  • Hydrogen can tbe used as such or in the form of a gas mixture containing hydrogen, for instance, a mixture of hydrogen and light hydrocarbons. When usin-g an excess of hydrogen it is advantageous to recirculate the remaining hydrogen, if desired after previously removing undesirable constituents.
  • the gases applied should preferably contain more than 60% v. of hydrogen. Very suitable are, for example, the hydrogen-containing gases obtained in the catalytic reforming of gasoline fractions.
  • the selective hydrogenation catalysts can ⁇ be used ⁇ in the uidized or suspended state, they are preferably used in the form of a xed bed. Since, as a result of the low hydrogenation temperatures, it is possible for the hydrocarbon mixture to be present at least partially, i.e., to an extent of more than 50% w. and preferably more than 75% w., in the liquid phase during the selective hydrogenation, without it being necessary to apply excessively high pressures. The so-called trickle technique is particularly suitable for this purpose.
  • the starting material which is present partly in the liquid phase and partly in the vapor phase, is allowed to flow downwards in the presence of hydrogen or of a hydrogen-containing gas over a xed bed of catalyst, the unvaporized part of the starting material owing over the catalyst particles in the form of a thin lm.
  • Hydrogenation in the liquid phase at a temperature of not more than 160 C. is usually conducted at pressures between and 60 atm. abs. and preferably between 20 and atm. aibs. ⁇ Owing to the exothermic nature of the hydrogenation reactions, a certain increase in temperature may occur in the catalyst bed. For this reason, too, it is advantageous to operate in the liquid phase, as, owing to the higher specific heat of the liquid, smaller rises in temperature will generally occur than when operating in the gaseous phase.
  • the space velocity is generally 0.5 to 5 kg. and preferably 1-3 kg. of hydrocarbon mixture per hour per liter of catalyst.
  • the gas-hydrocarbon ratio is generally between and 300 liters (measured at standard conditions) of gas per kilogram of hydrocarbon mixture.
  • the present invention is particularly suitable for the recovery of aromatics, e.g., benzene, toluene, xylene and/ or ethyl benzene, for use in the chemical industry.
  • aromatics e.g., benzene, toluene, xylene and/ or ethyl benzene
  • Especially desirable starting materials are hydrocarbon mixtures of which at least v. has a boiling point lower than 200 C. (ASTM).
  • Particularly suitable are the light boiling fractions of the thermally cracked gasolines referred to above, which generally have a relatively high content of highly unsaturated compounds, including cyclic dienes, such as cyclopentadiene, methyl cyclopentadiene and cyclohexadiene, as well as dimers.
  • this trouble can be obviated by simple means by subjecting the starting material containing the dimer, before extraction, to fractional distillation in such a manner that the fraction to be extracted has a nal boiling point of not more than 160 C. (atmospheric pressure).
  • this distillation is preferably carried out under reduced pressure, in such a way that the bottom temperature does not rise above 100 C.
  • the selective hydrogenation and/ or extraction is preferably applied to a hydrocarbon mixture from which the components having a boiling point lower than that of benzene are partially or completely removed.
  • the starting material is a hydrocarbon mixture from which the components having a final boiling point of 60 C. or less are removed, for example, by distillation.
  • the extraction of the aromatic Ihydrocarbons from the selectively hydrogenated product is effected in a multistage counter-current extraction system, for which a column, for example, filled with packing material or fitted with perforated trays, is suitable.
  • a column is used -in which a shaft with discs is rotatably mounted as described, for example, in U.S. Patent 2,601,- 674 to G. H. Reman.
  • suitable extraction agents are the polar solvents known to be selective for aromatics.
  • a solvent, or mixture of solvents is chosen with a boiling point higher than that of the starting material to be extracted. These solvents are used as such or in the presence of water in a quantity preferably less than 10% v.
  • Particularly suitable selective solvents are diethylene glycol, dipropylene glycol and/ or other alkylene glycols, as well as sulfolane and/ or substituted sulfolanes, such as methyl and/or dimethyl sulfolane, or mixtures thereof.
  • the ratio by weight of solvent to the product to be extracted is generally between 3:1 and 101:1, and preferably between 411 and 6:1.
  • these ratios are generally between 1:1 and 4:1, and preferably lbetween 1.5:1 and 2.511.
  • the extract phase withdrawn from the extraction zone is passed into a stripper column to remove non-aromatic compounds.
  • a 'bottom temperature of not more than 170 C. and a pressure lower than that in the extraction system are preferably maintained.
  • the vaporous material from the top of the stripper consisting of non-aromatic hydrocarbons and part of the aromatic hydrocarbons, is condensed and recycled to the extraction system, where it is introduced near the end at which the extract phase is withdrawn.
  • the amount of material is to be recycled from4 the stripper to the extraction zone is chosen so as to ensure that the extract phase withdrawn from the bottom of the stripper has the required degree of purity, that is to say that is preferably contains less of 0.1% W. of non-aromatic components.
  • the ratio by weight of the material to be recycled from the stripper to the feed to be extracted is generally between 0.6:1 and 2:1, and preferably 'between 0.9:1 and 1.5 :1.
  • sulfolane or substituted sulfolanes are used as the selective solvents, this ratio by weight is generally between 0.311 and 1.5:1, and preferably *between 0.5 :1 and 1:1.
  • the extraction and recovery of light aromatic hydrocarbons with diethylene glycol and/ or dipropylene glycol as solvent is preferably carried out as follows.
  • a selectively hydrogenated hydrocarbon mixture containing benzene, toluene, xylene and/ or ethyl benzene is introduced into a multistage counter-current extraction system held at a temperature of not more than 150 C., and preferably :between 100 and 120 C., and at a pressure sufficient to keep the various streams in the liquid state.
  • diethylene glycol and/ or dipropylene glycol is introduced in a quantity of 4 to 6 parts by weight of product to be extracted and at the same end of the system the raffinate with only a slight content of aromatic hydrocarbons is withdrawn.
  • an extract phase with a high content of aromatics is discharged, which is passed, preferably without cooling, into a stripper column with at least four theoretical stages, where a bottom temperature between 40 and 160 C. and a pressure lower than that in the extraction system and preferably between 1 and 2 atm. abs. are maintained. Vapors from the stripper are condensed and, if necessary, any water phase formed can be separated and withdrawn. The Condensed vapors are recycled to the extraction zone where they are introduced at a point near the end at which the extract phase is withdrawn, preferably between the first and second theoretical stages.
  • the extract phase withdrawn from the bottom of the stripper is passed into a distillation column where a pressure lower than that in the stripper and preferably between 0.3 and 0.5 atm. abs. and a bottom temperature of less than 200 C. and preferably :between 150 C. and 180 C. are maintained.
  • the :diethylene glycol and/or dipropylene glycol withdrawn from the bottom of this column is returned, after cooling, to the extraction system.
  • the aromatic compoundfs) passing over the top of the distillation column is (are) i-f so desired further processed in one or more fractionating columns.
  • the extraction and recovery of light aromatic hydrocarbons with the aid of sulfolane as the solvent is preferably carried out in the same way as described above for diethylene glycol and/ or dipropylene glycol, except that in the extraction system temperatures between 90 C. and 110 C. are preferably applied, while 1.5-2.5 parts by weight of sulfolane per part 'by weight of material to be extracted is introduced. Moreover, a stripper column with at least 3 theoretical stages is generally applied.
  • the extraction process can be improved further by using a wash liquor (a counter solvent) at the same time.
  • This counter solvent can be introduced into the extraction system either together with the top product from the stripper column, or separately at a point near the end at which the extract phase is withdrawn.
  • ⁇ suitable counter solvents are paratiinic hydrocarbons or hydrocarbon mixtures containing at least 30% v. of paraflinic hydrocarbons.
  • a counter solvent of this kind is used, a smaller amount recycle from the stripper column to the extraction system is sufficient. This amount depends on, among other things, the composition of the counter solvent, and in particular on its aromatic content.
  • a counter solvent as referred to above has in general the drawback that it has to be separated again from the raffinate, for instance by distillation. It has now been found that this distillation can be omitted if the appropriate counter solvent is used.
  • a gasoline fraction is used as counter solvent the ratlinate mixture withdrawn from the extraction system can be used, for example, as motor fuel.
  • suitable counter solvents are gasoline fractions with a boiling range between C. and 180 C., such as a platformate fraction, or a naphtha obtained .by direct distillation with a content of at least 30% v. of paratlinic hydrocarbons. In the event of a counter solvent containing aromatic hydrocarbons, these are recovered, as an additional advantage, together with the aromatics from the starting material.
  • the load on the extraction system and the subsequent stripper and distillaton columns can be reduced by removing from the selectively hydrogenated product all or part of the components that have a higher and/or lower boiling point than the aromatic hydrocarbon (s) to be recovered.
  • the narrow fraction thus obtained can be subjected to a complete hydrogenation before extraction, in order to convert the relatively -small amount of alkenes present in this fraction into alkanes.
  • This hydrogenation can be carried out in a known way, for example with a cobalt-molybdenum catalyst under a pressure of 20 atm. abs., a temperature of 300 C., a space velocity of 1 kg. per liter per hour and a molar ratio of hydrogen to hydrocarbon of 4.
  • a lsmall amount e.g. ybetween 0.05 and 1% w. of phenothiazine or a substituted phenothiazine, can be added to the solvent.
  • the invention is further illustrated yby reference to the drawing which is ⁇ a schematic diagram of the process of the invention and by four examples wherein the same selectively hydrogenated product is used as the base material in order to facilitate a comparison of results.
  • Examples I and Il refer to the pdeparation of pure benzene and of pure benzene, toluene, xylene and ethyl benzene, respectively, using diethylene glycol as the selective solvent.4
  • Example lll illustrates the recovery of pure benzene with diethylene glycol as the selective solvent, applying a counter solvent.
  • Example IV describes the recovery of pure benzene, extraction being elfected with sulfolane as the selective solvent.
  • Compositions of the various streams, as occurring in Examples I-IV are summarized in Tables I-IV, the columns of the tables being numbered in the same Way as the corresponding lines in the figure; the compositions of the various streams being based on 100 parts by weight of the starting material.
  • the laromatic compounds produced according to the present invention are substantially pure, i.e. above 99% purity.
  • a benzene with a purity of 99.9% or higher anda melting point higher than 5.4 C. can be obtained.
  • the product does not yet completely fulfill the socalled acid wash color test (ASTM D 848-47).
  • ASTM D 848-47 acid wash color test
  • the product J mplies with all the requirements for ASTM test D 83 5- for nitration grade products.
  • Example l This example illustrates the recovery of pure benzene fom a gasoline obtained as a byproduct in the preparation f ethylene and propylene by steam cracking a straightun hydrocarbon oil having a linal boiling point of 230 I.
  • the composition of this gasoline is listed in column 1 f Table I.
  • Other properties of the gasoline were: boilig range 26 C.-160 C. (ASTM), sulfur content 15 upm., bromine value 50 g./100 (Mcllhiney method), maaic anhydride number 130 mg./g. (Ellis and Jones methd), and hydrogen consumption upon complete hydrogenaion of all unsaturates 90 liters (STN/kilogram.
  • this gasoline was fed, prin- :ipally in the liquid state and in the presence of 175 liters STP) of hydrogen per kg. of this gasoline, through line l int-o reaction Zone A.
  • the reactor contained a nickel :atalyst supported on alumina as carrier, in the form of l x 3 mm. pellets, which had ⁇ been sulfided at a temperaure of 100 C. 'with hydrogen sulfide.
  • Other conditions or the selective hydrogenation were: average catalyst ternvJerature 100 C., pressure 40 atm. abs. and a space velocity 3f 2 kg. of gasoline per hour per liter of catalyst.
  • the selectivity hydrogenated liquid product withdrawn via line 2 had the composition listed in column 2 of Table l.
  • This product was fed into fractionating column B wherein most of the components with a boiling point lower than that of benzene were ⁇ removed under a pressure of 1 atm. abs. Composition of the light tops is given in extraction column D via line 10. A pressure of 2 atm. abs. and a bottom temperature of 140 C. were maintained in stripping column E. Extract phase was withdrawn, via line 12 from the bottom of stripping column E, and then passed, without coo-ling, into distillation column F at a point halfway between the top ⁇ and the bottom trays of the column. Column F, having a total of eight theoretical stages, was operated at a pressure of 0.6 atm.
  • compositions of the various streams are listed in Table I.
  • the numerical headings in the table refer to the corresponding stream shown in the drawing.
  • the compositions are expressed as parts by weight based on 100 parts by weight of original steam cracked gasoline feed.
  • extraction column D having 13 theoretical stages.
  • the benzene-containing feed was introduced continuously .at a place corresponding to 3 theoretical stages from the bottom of the column.
  • Diethylene glycol was introduced as selective solvent via ⁇ line 9, in a quantity of 4 parts by weight per part by weight of feed.
  • a raffinate phase containing no more than 0.5 part by weight of benzene was withdrawn from the top of the extraction column through line 8.
  • ⁇ an extract phase was withdrawn and introduced, without cooling, into the top of stripper column E, having eight theoretical stages, to remove light non-aromatic hydrocarbons present in the extract phase.
  • Extraction was effected in extraction column D, with 13 theoretical stages, the benzene-containing feed being introduced at a point corresponding to three theoretical stages from the bottom of column D.
  • the extraction was carried out with diethylene glycol as the selective solvent with a ratio of six parts by weight of solvent per part by weight of feed, a pressure of 10 atom. abs. and at a temperature of 100 C.
  • the extract phase removed through line 10 was separated from light non-aromatic hydrocarbons in stripper column E at a pressure at 1.2 atm. abs. and a Ibottom temperature of 145 C.
  • Stripper column E was operated under a pressure of 1 atm. abs. with a bottom temperature of 135 C. and a top temperature of 100 C.
  • the top product was discharged and recycled to the extraction column.
  • the extract phase withdrawn through line 12 at the bottom of column E was fractionated in column F under a pressure of 0.5 atm. abs. with a bottom temperature of 160 C. and a top temperature of 70 C.
  • the distillate discharged through line 14 was passed to column G where pure benzene was obtained over the top.
  • a bottom product was removed that contained, among other compound, C7 and C8 hydrocarbons from the counter solvent.
  • Example III For the recovery of pure benzene, the same selectively hydrogenated product described as the starting material. of the components with a boiling point lower or higher than that of benzene was effected in distillation columns B and C in the same way as described in Example I. Extraction of the benzene-containing mixture discharged in Example I was used TABLE IIL-COMPOSITIONS ARE BASED The removal of the major part motor gasoline component. It is observed that in consequence of the application of the counter solvent a saving of heat is effected, because smaller quantities of material from the top of stripper column E are returned to extraction column D than in the process according to Example I, the amounts being 32 parts by weight as against 51.6 parts by weight. Compositions of the various streams are given in Table III.
  • a plattormate fraction with a boiling range of from 95-130 C. was used as counter solvent, which was introduced through line 7 near the bottom of extraction column D in a Example l V las passed to extraction column D, with eight theoetical stages, at a point corresponding to two theoretical tages, from the bottom of the column. Extraction was ffected at a temperature of 90 C. and a pressure of 1 atm. abs.
  • Stripper column E was operated at a pres- ;ure of 2.6 atm. abs. and at a bottom temperature of 50 C. and a top temperature of 100 C., while in :olumn F a pressure of 0.35 atm. abs., a bottom tem- Jerature of 160 C. and a top temperature of 50 C. were naintained.
  • the benzene recovered through line 14 was Eractionated further in column G.
  • a process for the recovery of an aromatic hydrocarbon having from 6 through 8 carbon atoms per molecule from a cracked gasoline containing said aromatic hydrocarbon, alkenes and alkadienes which comprises passing said gasoline together with hydrogen over a selective hydrogenation catalyst under selective hydrogenation conditions to hydrogenate at least 95% of the alkadienes while converting less than 25% of the alkenes to alkanes, fractionating the hydrogenated gasoline to obtain a light fraction having a nal boiling point not more than 160 C., said fractionation being carried out under reduced pressure and with a bottom temperature below C., and extracting said aromatic hydrocarbon from 55 than C., said fractionation being carried out under reduced pressure and with a bottom temperature below 100 C., and extracting said aromatic hydrocarbon from the light fraction by means of a solvent selective for aromatics.

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
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Cited By (4)

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Publication number Priority date Publication date Assignee Title
US4117303A (en) * 1976-04-28 1978-09-26 Ab Svetsia Arrangement in electrical welding apparatus
US4587369A (en) * 1983-10-25 1986-05-06 Institut Francais Du Petrole Selectively hydrogenating acetylenic compounds in a high butadiene content C4 cut
EP0792928A2 (de) * 1996-02-03 1997-09-03 Krupp Uhde GmbH Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens
US20220306950A1 (en) * 2020-06-16 2022-09-29 Lg Chem, Ltd. Method of producing aromatic hydrocarbons

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US2694671A (en) * 1950-09-01 1954-11-16 Standard Oil Dev Co Selective hydrogenation process
US2717861A (en) * 1954-08-11 1955-09-13 Exxon Research Engineering Co Selective hydrogenation process
US2799627A (en) * 1953-08-17 1957-07-16 Universal Oil Prod Co Process for obtaining concentrated aromatic hydrocarbons
US2870226A (en) * 1956-03-19 1959-01-20 Universal Oil Prod Co Production and recovery of aromatic hydrocarbons
US2952717A (en) * 1957-04-18 1960-09-13 Union Oil Co Separation of hydrocarbons by dual solvent extraction
US3030299A (en) * 1959-03-18 1962-04-17 Shell Oil Co Production of jet fuels

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2694671A (en) * 1950-09-01 1954-11-16 Standard Oil Dev Co Selective hydrogenation process
US2799627A (en) * 1953-08-17 1957-07-16 Universal Oil Prod Co Process for obtaining concentrated aromatic hydrocarbons
US2717861A (en) * 1954-08-11 1955-09-13 Exxon Research Engineering Co Selective hydrogenation process
US2870226A (en) * 1956-03-19 1959-01-20 Universal Oil Prod Co Production and recovery of aromatic hydrocarbons
US2952717A (en) * 1957-04-18 1960-09-13 Union Oil Co Separation of hydrocarbons by dual solvent extraction
US3030299A (en) * 1959-03-18 1962-04-17 Shell Oil Co Production of jet fuels

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4117303A (en) * 1976-04-28 1978-09-26 Ab Svetsia Arrangement in electrical welding apparatus
US4587369A (en) * 1983-10-25 1986-05-06 Institut Francais Du Petrole Selectively hydrogenating acetylenic compounds in a high butadiene content C4 cut
EP0792928A2 (de) * 1996-02-03 1997-09-03 Krupp Uhde GmbH Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens
JPH09309846A (ja) * 1996-02-03 1997-12-02 Krupp Uhde Gmbh 改質ガソリンから純粋な芳香族化合物を製出する方法およびこの方法を実施するための装置
EP0792928A3 (de) * 1996-02-03 1998-04-01 Krupp Uhde GmbH Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens
US6124514A (en) * 1996-02-03 2000-09-26 Krupp Uhde Gmbh Process for generating pure benzene from reformed gasoline
JP4514839B2 (ja) * 1996-02-03 2010-07-28 バスフ・アクチエンゲゼルシヤフト 改質ガソリンから純粋な芳香族化合物を製出する方法およびこの方法を実施するための装置
US20220306950A1 (en) * 2020-06-16 2022-09-29 Lg Chem, Ltd. Method of producing aromatic hydrocarbons
US11667855B2 (en) * 2020-06-16 2023-06-06 Lg Chem, Ltd Method of producing aromatic hydrocarbons

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GB954439A (en) 1964-04-08
NL113747C (US06168776-20010102-C00041.png)
BE615315A (US06168776-20010102-C00041.png)
DE1468566C3 (de) 1979-11-29
DK105331C (da) 1966-09-19
DE1468566A1 (de) 1968-12-05
NL262671A (US06168776-20010102-C00041.png)

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