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WO1994000409A1 - Procedes non extractifs de production d'aromatiques de grande purete - Google Patents

Procedes non extractifs de production d'aromatiques de grande purete Download PDF

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Publication number
WO1994000409A1
WO1994000409A1 PCT/US1993/005814 US9305814W WO9400409A1 WO 1994000409 A1 WO1994000409 A1 WO 1994000409A1 US 9305814 W US9305814 W US 9305814W WO 9400409 A1 WO9400409 A1 WO 9400409A1
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WO
WIPO (PCT)
Prior art keywords
process according
aromatics
aromatic
feedstock
zeolite
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1993/005814
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English (en)
Inventor
Robert A. Innes
Bernard F. Mulaskey
Robert G. Wall
Peter M. Shebek
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
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 Chevron Research and Technology Co filed Critical Chevron Research and Technology Co
Priority to AU45390/93A priority Critical patent/AU4539093A/en
Priority to GB9416348A priority patent/GB2279661B/en
Priority to DE4393010A priority patent/DE4393010C1/de
Publication of WO1994000409A1 publication Critical patent/WO1994000409A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/16—Metal oxides
    • 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
    • C10G35/00—Reforming naphtha
    • C10G35/04—Catalytic reforming
    • C10G35/06—Catalytic reforming characterised by the catalyst used
    • C10G35/095—Catalytic reforming characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves

Definitions

  • the present invention relates to new methods for producing aromatics. Specifically, the invention relates to catalytic . processes by which aromatic streams, containing nonaromatic impurities having boiling points in the same temperature range as the aromatics, are purified. Most particularly, the invention describes nonextractive catalytic processes for producing high purity aromatics.
  • Suitable aromatic feeds for petrochemical production include benzene, toluene, and C ⁇ aromatics.
  • these aromatics are produced in admixtures with other components during catalytic naphtha reforming or as by-products of ethylene manufacture.
  • the liquid product produced from naphtha reforming referred to as reformate, contains a mixture of hydrocarbon species including aromatics such as benzene, toluene and xylene, commonly referred to together as BTX.
  • separation may be achieved by resort to extractive methods using solvents that have a high relative affinity for aromatics compared to nonaromatics.
  • extractive processes commonly used in industry are liquid-liquid extraction or extractive distillation, such as UOP's UDEXTM and SULFOLANETM processes.
  • Catalysts may be used to selectively remove nonaromatics from the reformate.
  • U.S. Patent No. 3,849,290 describes a multi-step process to upgrade the octane rating of a naphtha gasoline blending stock.
  • the stock is reformed over a nonacidic platinum-type catalyst, producing a reformate containing aromatics and paraffins.
  • the reformate is then contacted under mild hydrocracking conditions with an intermediate pore zeolite to selectively crack high boiling, low octane paraffins, e.g., C 7 +.
  • the effluent from this hydrocracking step is contacted with a small pore catalyst to selectively hydrocrack low boiling, low octane C 6 - paraffins.
  • This three step, three catalyst processing sequence yields a high octane product after the preferential removal of low octane species, but the product purity is insufficiently high for petrochemical applications.
  • U.S. Patent No. 4,795,550 describes a low temperature catalytic process for removing olefinic impurities, but not paraffins or naphthenes, from an aromatic stream having a bromine index between 50 and 2000.
  • U.S. Patent No. 4,150,061 describes a process whereby a fractionated pyrolysis gasoline comprising toluene, xylenes, ethylbenzenes, C 7 - C 10 paraffins, olefins and naphthenes are selectively hydrodealkylated and transalkylated to give ethylbenzene-lean xylenes and benzene in the presence of a catalyst comprising a tungsten/molybdenum component ( 0 3 -Mo0 3 ) and an acidic component of 60 wt% mordenite and 40 wt% catalytically active alumina.
  • a catalyst comprising a tungsten/molybdenum component ( 0 3 -Mo0 3 ) and an acidic component of 60 wt% mordenite and 40 wt% catalytically active alumina.
  • U.S. Patent No. 4,861,932 describes a process for producing gasoline blending stocks in which nonaromatic C 2 -C 12 paraffins are converted to a mixture of higher octane aromatics and alkylaromatics by first contacting the paraffins with a noble metal/low acidity catalyst. The effluent is then contacted with an acidic catalyst based on a zeolite such as ZSM-5 with a metal such as gallium (Ga) . Although the Ga/ZSM-5 catalyst is known to have a high aromatic selectivity, the product purity is insufficiently high for petrochemical applications.
  • An additional aspect of the present invention is to provide a catalytic process by which nonaromatic components of an aromatic stream, boiling in the aromatic range, are converted in a single catalytic step to species that can be easily separated from the aromatics without resort to extractive techniques.
  • an aromatic feedstock containing close-boiling nonaromatics may be purified in a single catalytic step to yield high purity aromatic chemicals.
  • the aromatic feedstock is contacted with an acidic catalyst to yield a liquid product having nonaromatic impurities with boiling points substantially outside the boiling point range for the aromatics.
  • High purity or chemical grade aromatics may then be recovered from the product by separation, e.g. , simple distillation, at considerably less expense than in current commercial practices that use extractive methods.
  • high purity benzene may be produced using a process in which nonaromatic impurities boiling in the same temperature range as benzene may be selectively eliminated by use of an acidic zeolite catalyst under elevated temperature conditions followed by distillation.
  • high purity benzene, toluene or C 8 aromatics are produced in a nonextractive process comprising reforming a naphtha stream over a nonacidic catalyst, reacting all or a portion of the reformate over an acidic catalyst and recovering .a high purity aromatic product by distillation.
  • the reformate is distilled to obtain a benzene-, toluene-, or xylene-rich fraction prior to reaction over the acidic catalyst.
  • the principal aim of the present invention is to produce high purity aromatic streams by selectively removing nonaromatic impurities having boiling points in the benzene, toluene and xylene (BTX) boiling range from aromatic streams by nonextractive techniques.
  • This boiling range generally covers temperatures between about 140'F and 350 * F (about 60 * C and 180 * C).
  • These nonaromatics may be referred to herein as close-boiling nonaromatics.
  • the process in general involves cracking the nonaromatic impurities boiling in the aromatics range by their selective reaction over an acidic catalyst.
  • the close-boiling nonaromatics are converted to light paraffins and olefins boiling substantially outside the BTX range.
  • the light paraffins and olefins may form additional aromatics by alkylation or aromatization.
  • nonextractive it is meant that separation of hydrocarbon species is achieved on the basis of differences in boiling point as opposed to reliance on a solvent.
  • the purity of the aromatics produced is preferably at least about 95 wt%, more preferably at least about 99.0 wt%, even more preferably at 99.5 wt% and most preferably at least about 99.8 wt%.
  • These aromatic products may be referred to herein as substantially free of nonaromatic impurities.
  • Catalyst acidity is essential to the nonextractive conversion step.
  • one measure of catalyst acidity is n-hexane cracking activity.
  • ⁇ represents the relative n-hexane cracking activity of a catalyst compared with a standard catalyst. The test is described more fully in U.S. Patent No. 3,354,078, the Journal of Catalysis/ vol. 6, p. 522-529, (Aug. 1965) and the Journal of Catalysis. Vol. 61, p. 395 (1980) .
  • a catalyst is "acidic" if a is greater than about 10, or more preferably, is greater than about 50.
  • Highly acidic catalysts have ⁇ values greater than about 100.
  • Acidic catalysts that are useful in the present invention are characterized by this definition of acidity.
  • useful acidic catalysts may be based on molecular sieves such as ZSM-5, beta-zeolite, X-zeolite, Y-zeolite, mordenite, ZSM-11, SSZ-23 (described in U.S. Patent No. 4,902,844), SSZ-25 (described in U.S. Patent No. 4,826,667) and SSZ-26 (described in U.S. Patent No. 4,910,006).
  • the sieves are preferably bound with any of a variety of well-known inorganic oxide binders.
  • Appropriate binders include inorganic compositions with which the molecular sieve can be combined, dispersed or otherwise intimately admixed.
  • Preferred oxide binders include alumina, silica, naturally occurring and conventionally processed clays, for example, bentonite, kaolin, sepiolite, attapulgite and halloysite.
  • the selective conversion of nonaromatics in an aromatics-rich stream may be performed in either a liquid or gaseous state. Also, under appropriate conditions, a suitable feed may be provided where liquid and gas phases are in equilibrium.
  • reaction conditions should be such as to promote the preferential catalytic conversion of the nonaromatics.
  • the process conditions such as pressure
  • the pressure should be between about 150-1000 psig.
  • the preferred temperature is between about 500 * F to about 700 * F (260 * .C - 371"C).
  • the feed weight hourly space velocity may vary from 0.1 to 100, but is typically between 0.5 and 10.
  • the presence of a liquid phase serves to wash the catalyst and keep it active.
  • the process conditions should be such that the feed remains gaseous.
  • the temperature may be relatively higher and the pressure may be relatively lower than for a liquid phase feed. Suitable reaction temperatures are between about 600 * F and 1200 * F (204 * C -
  • the processes of the present invention may be used to make high purity aromatics streams from a variety of feeds.
  • Typical feeds include reformates, pyrolysis gasolines, and fractions and mixtures thereof. These feeds should contain at least about 70 wt% aromatics, preferably at least about 80 wt% and more preferably at least about 90 wt%, in order to minimize production of light gases and enhance both the cost- effectiveness of the processes of the present invention and their suitability for use with the nonextractive processes described herein.
  • a reformate obtained by reforming a naphtha feed is purified by reaction over an acidic catalyst.
  • a feed could be a light naphtha feed, for example, one rich in C 6 and/or C 7 components, reformed over any of a variety of conventional reforming catalysts to produce a product stream containing aromatics and close-boiling nonaromatics.
  • Exemplary reforming process conditions include: feed rate of 0.1-10 WHSV, pressures between about 40 psig and 100 psig, temperatures between about 800'F and 1100'F, and a hydrogen:feed molar ratio of between about 0.1-10.
  • a nonacidic catalyst may be used to reform the naphtha feed and increase its aromatics content. Accordingly, ⁇ values should be less than 10 and preferably less than 0.1. In fact, strong catalyst acidity in aromatics generation is undesirable because it promotes cracking that in turn results in lower aromatic selectivity.
  • the catalyst may contain an alkali metal and/or an alkaline earth metal. The alkali or alkaline earth metals are preferably incorporated into the catalysts during or after synthesis according to conventional methods. In addition, at least 90% of the acid sites are desirably neutralized by introduction of the metals, more preferably at least 95%, most preferably 100%.
  • the catalyst for aromatics generation may be based on alumina or molecular sieves, such as L-zeolite or silicalite, with an inorganic binder.
  • Preferred catalysts for reforming include catalysts comprising platinum on nonacidic forms of beta-zeolite, ZSM-5, silicalite and L-zeolite.
  • Other well-known reforming catalysts typically contain a catalytic metal such as platinum disposed on any of a plethora of natural and man-made crystalline aluminosilicates.
  • Metallic promoters such as Group VIII metals rhenium and indium also may be included, as can other promoter metals such as tin and germanium.
  • Examples of methods of manufacture of ZSM-5 and particularly the ZSM-5 having high silica-alumina (Si0 2 :Al 2 0 3 ) molar ratio, sometimes referred to as silicalite are shown in: Dwyer, et al., U.S. Patent No. 3,941,871, issued March 2, 1976 and U.S. Patent No. 4,441,991, issued April 10, 1984; and Derouane, et al., EPO Application No. 186,479, published February 7, 1986, all of which are incorporated by reference in their entireties.
  • Examples of the preparation of nonacidic platinum on silicalite or L-zeolite catalysts may be found in U.S. Patent Nos. 4,830,732 and 5,073,250.
  • Low sulfur feeds to the aromatics generation step may be particularly attractive in order to avoid poisoning the reforming catalyst.
  • the feed to the reformer has sulfur content less than 50 ppbw, and more preferably less than 5 ppbw.
  • valuable C 6 -C 8 aromatics may be produced from relatively inexpensive hydrocarbon feeds such as pyrolysis gasolines and paraffinic naphthas.
  • the products are streams containing ethylbenzene, benzene, toluene, and the three xylene isomers.
  • the aromatics generation procedure converts such hydrocarbon feedstocks into very clean aromatic mixtures that, however, include close-boiling nonaromatic impurities.
  • the process according to the present invention then converts the close-boiling nonaromatic impurities to yield a product that in turn may be distilled to yield high purity aromatic streams.
  • the process uses two separate catalysts: a nonacidic catalyst.to generate aromatics and an acidic catalyst to purify the aromatics generated.
  • Such a process could involve passing an inexpensive hydrocarbon feed over a nonacidic catalyst such as platinum on silicalite (alumina content between about 200-2000 ppm) .
  • a nonacidic catalyst such as platinum on silicalite (alumina content between about 200-2000 ppm) .
  • Such a catalyst is especially effective at aromatizing the feed, but, as described above, produces a complex mixture containing nonaromatics that are difficult to separate from the desired aromatics. This selectivity is valuable in the production of petrochemicals because of the high benzene content (about 70-75 wt%) product.
  • an acidic catalyst cleans up the mixture by converting the close-boiling nonaromatic components into both lighter and heavier components that can be easily separated from the aromatics, for example, by distillation.
  • the impure distillate contains C 3 -C 4 and C ⁇ + hydrocarbons, the latter of which can be recycled for further aromatics generation.
  • This beneficial combination of two different catalysts serves to facilitate the production of high purity aromatics such as BTX.
  • the following example illustrates a process according to this embodiment.
  • EXAMPLE 1 A light reformate stream was aromatized over a nonacidic platinum on silicalite (alumina content less than 2000 ppm) catalyst to yield a product containing about 73 wt% total BTX and about 22 wt% of other C 6 + hydrocarbons.
  • the aromatics-enriched product stream (the liquid feed referred to in Table A) was contacted with an acidic Ga/HZSM-5 catalyst at 707'F (375 * C) in the presence of added hydrogen.
  • the liquid feed was contacted with the same acidic catalyst at 842'F (450 * C) without hydrogen.
  • Other process conditions are provided in Table A. As illustrated in Table A, the percentage of
  • BTX relative to the total C 6 -C ⁇ content of the liquid feeds and products increased from 76.6 wt% in the feed to about 94 wt% and about 98.9 wt% in the respective aromatics-enriched liquid product streams after treatment according to the method of the present invention.
  • High purity aromatics can be easily separated from the product streams by distillation.
  • nonaromatic impurities boiling in the same temperature range as benzene may be eliminated from a benzene stream by their selective reaction in the gas phase over an acidic zeolite catalyst under elevated temperature conditions. For example, at between 600 * F -
  • High purity benzene may be manufactured by such a process that includes: reforming a predominantly C 6 naphtha feed to yield greater than 70 wt% aromatics, separating a light fraction from a benzene and heavier fraction by distillation, passing the benzene and heavier fraction over an acidic HZSM-5 at 800 * F - 1100'F (427"C - 593'C) and recovering a highly pure benzene fraction by distillation.
  • This process eliminates the need for expensive liquid extraction or extractive distillation processes.
  • Tables B and C show that substantially all nonaromatic impurities in the feeds to the acidic conversion step were converted to C 1 -C 4 paraffins and C 7 + aromatics.
  • the aromatic products were recovered by condensation, while the light paraffins were carried off in the hydrogen stream product. Further distillation of the aromatics fraction would be expected to yield better than a 99.9 wt% purity benzene and a C 7 + aromatics stream suitable for gasoline blending.
  • high purity benzene and xylenes can be made from impure toluene streams by using acidic catalysts with high cracking activity, such as beta-zeolite or HZSM-5.
  • acidic catalysts with high cracking activity such as beta-zeolite or HZSM-5.
  • toluene disproportionation conditions up to about 10 wt% of nonaromatic impurities in the toluene feedstream are converted to light ends, enabling the recovery, for example, by distillation, of benzene, toluene and C 8 aromatic fractions that are between 99.5 -
  • a toluene portion of a reformate or pyrolysis gasoline stream can be directed to a reactor where a process according to the present invention is carried out, bypassing an extraction, e.g., UDEXTM, plant, and freeing up capacity for benzene production.
  • the impure toluene stream in either liquid or gaseous phase, can be reacted over the acidic catalyst to ultimately yield high purity aromatic streams.
  • the present invention according to this embodiment is illustrated in Examples 4 and 5.
  • Debutanized reformate was distilled to obtain light and heavy fractions.
  • the heavy reformate was further distilled to a 30% cut point.
  • the overhead product of the second distillation comprising about 92 wt% toluene was vaporized, blended with hydrogen, and passed through a tubular fixed-bed reactor charged with an acidic ZSM-5 catalyst.
  • the reaction was carried out at 1000'F (538 * C), 150 psig, and 5.7 liquid toluene feed weight hourly space velocity (WHSV) .
  • the hydrogen: toluene molar ratio was about three-to-one.
  • Feed and product analyses were obtained by capillary gas-liquid chromatography after nine hours on stream, as shown in Table D below.
  • the gas chromatograph was equipped with a flame ionization detector and a polar column that eluted nonaromatics before aromatics.
  • the analyses show that the toluene disproportionated to make benzene and xylenes, while nonaromatic impurities in the same boiling range were substantially eliminated by cracking to form light ends.
  • the product can be distilled to obtain high purity aromatics.
  • toluene was disproportionated to make benzene and xylenes, while close-boiling nonaromatics were simultaneously removed by cracking.
  • the high purity benzene and xylenes may be separated by simple distillation.
  • the invention described herein utilizes catalytic processes to produce high purity aromatics.
  • the processes described herein provide effective and direct means to obtaining high purity aromatics such as benzene and C 8 aromatics. Close-boiling nonaromatics are eliminated without resort to extractive techniques because of their preferential conversion by an acidic catalyst to nonaromatics that are easily separable from the aromatics on the basis of boiling point differences.
  • the versatility of the process is demonstrated in its combination with other processes such as reforming to produce high purity aromatic streams. Further, in view of these combinations, a wide variety of hydrocarbon feeds can be used, from impure aromatic streams to paraffinic feedstocks and the feeds may be in either liquid or gas form. Further, the process of the present invention contemplates the treatment of nonaromatic stocks that can be aromatized before the acidic purification step as described herein. Process conditions may be selected from wide temperature (500 * F - 1200'F) and pressure ranges (0 - 1000 psig) based on the nature of the feed, catalyst and economic considerations. Industrial Applicability
  • the present invention is useful for its ability to produce high purity aromatics, such as benzene and xylenes, from aromatic streams containing nonaromatic impurities boiling in the same temperature range as the aromatics.
  • the purified aromatics can be used as petrochemical feedstocks.

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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)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Catalysts (AREA)

Abstract

L'invention se rapporte à de nouveaux procédés non extractifs de production d'aromatiques de grande pureté et qualité chimique (par exemple, le benzène, le toluène, le xylène) à partir de courants d'hydrocarbures. Pour des charges de départ d'aromatiques contenant des composants non aromatiques à points d'ébullition proches, le courant est mis en contact avec un catalyseur acide. En conséquence, des impuretés non aromatiques possédant des points d'ébullition dans l'intervalle aromatique sont transformées par catalyse en d'autres espèces possédant des points d'ébullition pratiquement hors de l'intervalle d'ébullition aromatique. Les aromatiques désirés dans le produit peuvent être séparés par simple distillation. L'invention se rapporte également à des procédés non extractifs incorporant un double traitement du catalyseur. Des charges de naphta sont aromatisées, dans une première étape, au contact d'un catalyseur non acide, produisant un mélange d'aromatiques et d'impuretés non aromatiques à des points d'ébullition dans l'intervalle aromatique. Dans une seconde étape, le mélange est mis en contact avec un catalyseur acide dans des conditions qui produisent un effluent pratiquement libre d'impuretés non aromatiques possédant des points d'ébullition dans l'intervalle aromatique. On peut obtenir des aromatiques de grande pureté en effectuant une simple distillation du produit.
PCT/US1993/005814 1992-06-18 1993-06-16 Procedes non extractifs de production d'aromatiques de grande purete Ceased WO1994000409A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU45390/93A AU4539093A (en) 1992-06-18 1993-06-16 Nonextractive processes for producing high purity aromatics
GB9416348A GB2279661B (en) 1992-06-18 1993-06-16 Nonextractive processes for producing high purity aromatics
DE4393010A DE4393010C1 (de) 1992-06-18 1993-06-16 Nicht-extrahierendes Verfahren zur Herstellung hochreiner Aromaten

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US90085792A 1992-06-18 1992-06-18
US07/900,857 1992-06-18
CN93107986A CN1098084A (zh) 1992-06-18 1993-07-24 生产高纯芳烃的非抽提法

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WO1994000409A1 true WO1994000409A1 (fr) 1994-01-06

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PCT/US1993/005814 Ceased WO1994000409A1 (fr) 1992-06-18 1993-06-16 Procedes non extractifs de production d'aromatiques de grande purete

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CN (1) CN1098084A (fr)
AU (1) AU4539093A (fr)
CA (1) CA2139785A1 (fr)
DE (1) DE4393010C1 (fr)
GB (1) GB2279661B (fr)
WO (1) WO1994000409A1 (fr)
ZA (1) ZA934391B (fr)

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RU2204584C2 (ru) * 1998-02-03 2003-05-20 Мобил Ойл Корпорейшн Способ снижения содержания бром-реакционноспособных загрязняющих примесей в ароматических материалах
US7731839B2 (en) 2005-05-27 2010-06-08 Exxonmobil Chemical Patents Inc. Process for reducing bromine index of hydrocarbon feedstocks
US8216450B2 (en) 2009-04-22 2012-07-10 Exxonmobil Chemical Patents Inc. Removal of bromine index contaminants from aromatic streams
US20170144948A1 (en) * 2014-06-26 2017-05-25 Sabic Global Technologies B.V. Process for producing purified aromatic hydrocarbons from a mixed hydrocarbon feedstream
US20170144946A1 (en) * 2014-06-26 2017-05-25 Sabic Global Technologies B.V. Process for producing alkylated aromatic hydrocarbons from a mixed hydrocarbon feedstream
WO2018047093A1 (fr) * 2016-09-12 2018-03-15 Sabic Global Technologies B.V. Procédé d'hydrocraquage
US10793491B2 (en) * 2014-06-13 2020-10-06 Sabic Global Technologies B.V. Process for producing benzene from C5-C12 hydrocarbon mixture

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US8057664B2 (en) 2005-11-17 2011-11-15 Exxonmobil Chemical Patents, Inc. Process for reducing bromine index of hydrocarbon feedstocks
US7744750B2 (en) 2005-11-17 2010-06-29 Exxonmobil Chemical Patents Inc. Process for reducing Bromine Index of hydrocarbon feedstocks
US7517824B2 (en) 2005-12-06 2009-04-14 Exxonmobil Chemical Company Process for steam stripping hydrocarbons from a bromine index reduction catalyst
US7553998B2 (en) * 2006-06-21 2009-06-30 Uop Llc Energy-efficient process for para-xylene production
CN107955644B (zh) * 2016-10-18 2020-07-14 中国石油化工股份有限公司 一种非芳轻烃的高效芳构化方法

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US4150061A (en) * 1977-11-08 1979-04-17 Standard Oil Company (Indiana) Process for converting pyrolysis gasoline to benzene and ethylbenzene-lean xylenes
US4441991A (en) * 1981-04-21 1984-04-10 Mobil Oil Corporation Catalytic dewaxing of oils containing ammonia over highly siliceous porous crystalline materials of the zeolite ZSM-5 type
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2204584C2 (ru) * 1998-02-03 2003-05-20 Мобил Ойл Корпорейшн Способ снижения содержания бром-реакционноспособных загрязняющих примесей в ароматических материалах
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AU4539093A (en) 1994-01-24
ZA934391B (en) 1994-01-17
GB2279661B (en) 1996-05-01
DE4393010C1 (de) 1997-05-07
CA2139785A1 (fr) 1994-01-06
GB9416348D0 (en) 1994-10-05
CN1098084A (zh) 1995-02-01
GB2279661A (en) 1995-01-11

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