EP0552070A1 - Erniedrigung des Benzolgehaltes von Benzinen - Google Patents

Erniedrigung des Benzolgehaltes von Benzinen Download PDF

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Publication number
EP0552070A1
EP0552070A1 EP93400021A EP93400021A EP0552070A1 EP 0552070 A1 EP0552070 A1 EP 0552070A1 EP 93400021 A EP93400021 A EP 93400021A EP 93400021 A EP93400021 A EP 93400021A EP 0552070 A1 EP0552070 A1 EP 0552070A1
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EP
European Patent Office
Prior art keywords
hydrogenation
isomerization
catalyst
charge
cut
Prior art date
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Application number
EP93400021A
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English (en)
French (fr)
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EP0552070B1 (de
Inventor
Christine Travers
Patrick Sarrazin
Jean-Marie Deves
Jean-Paul Boitiaux
Pierre Auboir
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Priority claimed from FR9200435A external-priority patent/FR2686094B1/fr
Priority claimed from FR929209758A external-priority patent/FR2694565B1/fr
Application filed by IFP Energies Nouvelles IFPEN filed Critical IFP Energies Nouvelles IFPEN
Publication of EP0552070A1 publication Critical patent/EP0552070A1/de
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Publication of EP0552070B1 publication Critical patent/EP0552070B1/de
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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
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/08—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one step of reforming naphtha
    • 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
    • C10G2400/02—Gasoline

Definitions

  • the invention relates to a process allowing the reduction of the benzene content in gasoline fractions by a process combining the hydrogenation of the benzene contained in the light reformate and optionally the hydrogenation of a C5-C6 cut and the isomerization of the effluent from hydrogenation and possibly from said cut.
  • Catalytic reforming used under severe conditions, and isomerization of normal C5-C6 paraffins of low octane number are the most commonly used processes currently for obtaining high octane numbers without the addition of lead.
  • the catalytic reforming process produces significant amounts of high octane benzene. This is why it is necessary to develop new processes which make it possible to reduce the benzene content of gasolines while meeting the specifications for the octane number.
  • the reduction of the benzene content of the reformate can also be carried out in various ways, such as for example the modification of the naphtha cutting point between reforming and isomerization or the separation of the reformate into two fractions: a heavy reformate and a light reformate in which all the benzene is concentrated.
  • This light fraction is then sent to a hydrogenation unit which transforms the benzene into naphthenes, which are then decyclized in an isomerization unit working under severe conditions.
  • the normal paraffins thus formed are isomerized by a conventional isomerization process (US-A 5,003,118).
  • a conventional isomerization process US-A 5,003,118.
  • the naphthenes adsorb on the catalyst and thus contribute to deteriorating its activity.
  • US-A-3,611,117 also describes a process for the hydroisomerization of cyclic hydrocarbons which uses a group VIII metal supported on zeolite as a catalyst for opening rings under severe operating conditions and as an isomerization catalyst in mild operating conditions.
  • the object of the present invention is to carry out jointly the reduction of the benzene content contained in the light reformate and the isomerization of the paraffins contained on the one hand in this light reformate and on the other hand in a C5-C6 cut generally paraffinic and from direct distillation.
  • the process of the present invention therefore comprises the hydrogenation of the benzene contained in the feed defined below in a hydrogenation zone and then the isomerization of the effluent resulting from the hydrogenation in an isomerization zone, the process being characterized in that a C5-C6 cut is mixed with said charge and / or said effluent.
  • the hydrogenation zone and the isomerization zone according to the invention can be included in the same reactor, or else in separate reactors such that each of said zones is included in at least one reactor.
  • the conditions under which the hydrogenation and isomerization are carried out are the conditions known to those skilled in the art. They are nevertheless specified below.
  • Benzene is generally essentially the only aromatic compound included in said fraction.
  • said fraction can comprise between 1 and 3% of olefinic hydrocarbons.
  • the weight composition of the C5-C6 cut generally resulting from direct distillation is variable. It depends on the nature of the crude to be treated in the case where the C5-C6 cut is obtained from direct distillation.
  • the paraffin content of said cut is generally greater than 90% by weight, its naphthene content generally less than 10% by weight and the benzene content generally less than 1.5% by weight. Its research octane number is generally between 60 and 75.
  • the light reformate content of the charge entering the hydrogenation zone being between 10 and 90% and preferably between 20 and 80%.
  • the C5-C6 cut is mixed with the effluent from the hydrogenation, that is to say with the saturated light reformate leaving the hydrogenation zone, the effluent content from the hydrogenation of the charge entering the isomerization zone being between 10 and 90% and preferably between 20 and 80%.
  • the pressure required for this hydrogenation stage is generally between 1 and 60 bar absolute, particularly between 2 and 50 bar and more advantageously between 5 and 45 bar.
  • the operating temperature is generally between 100 and 400 ° C, more advantageously between 150 and 350 ° C and preferably between 160 and 320 ° C.
  • the space velocities calculated with respect to the catalyst are generally between 1 and 50 h ⁇ 1 and more particularly between 1 and 30 h ⁇ 1 (volume of charge per volume of catalyst and per hour).
  • the flow of hydrogen, relative to the catalyst is generally between 1 and 2000 volumes (gas under normal conditions) per volume of catalyst and per hour.
  • the heat released at this stage is used to preheat the charge of the isomerization.
  • the catalyst used in the hydrogenation zone according to the process of the present invention comprises at least one metal M chosen from the group formed by nickel, platinum and palladium, used as it is or preferably deposited on a support.
  • the metal M must be in reduced form for at least 50% of its totality.
  • nickel or platinum is used, and even more preferably platinum.
  • the catalyst can advantageously contain at least one halogen in a proportion by weight relative to the catalyst of between 0.5 and 2%.
  • halogen in a proportion by weight relative to the catalyst of between 0.5 and 2%.
  • chlorine or fluorine or a combination of the two is used in a proportion relative to the total weight of catalyst of between 0.5 and 1.5%.
  • the proportion of metal M relative to the total weight of catalyst is between 0.1 and 60%, more particularly between 5 and 60% and preferably between 5 and 30%.
  • the total proportion of the metal M by relative to the total weight of catalyst is between 0.1 and 10% and preferably between 0.05 and 5%.
  • the support can be chosen from the group formed by alumina, silica-aluminas, silica, zeolites, activated carbon, clays and aluminous cements.
  • An alumina is preferably used, with a specific surface at least equal to 50 m2 / g and with a pore volume at least equal to 0.4 cm3 / g, for example with a specific surface of between 50 and 350 m2 / g and with a pore volume included between 0.4 and 1.2 cm3 / g.
  • the effluent from the hydrogenation zone generally contains less than 0.1% of aromatics and generally has between 4 and 6 points of octane index less than the feed entering this zone.
  • the isomerization zone is supplied by the effluent from the hydrogenation zone alone, comprising the light reformate mixture plus the hydrogenated C5-C6 cut, or by a light reformate mixture plus non-hydrogenated C5-C6 cut.
  • the isomerization is generally carried out in said isomerization zone under the following usual conditions: the temperature is between 150 ° C and 300 ° C and preferably between 230 and 280 ° C, and the partial pressure of hydrogen is between atmospheric pressure and 70 bar and preferably between 5 and 50 bar.
  • the space velocity is between 0.2 and 10 liters and preferably between 0.5 and 5 liters of liquid hydrocarbons per liter of catalyst per hour.
  • the hydrogen / charge molar ratio is normally between 0.5 and 10 and preferably between 1 and 3.
  • the catalyst used in the isomerization zone according to the process of the present invention can be a catalyst based on platinum on chlorinated alumina, said alumina containing from 1 to 10% of chlorine and preferably from 2 to 9% of chlorine, but preferably using a catalyst comprising at least one group VIII metal and a zeolite.
  • zeolites can be used for said catalyst such as for example mordenite or ⁇ zeolite.
  • the mordenite thus prepared is then mixed with a generally amorphous matrix (alumina, silica alumina, kaolin, ...) and shaped by any method known to those skilled in the art (extrusion, pelletizing, coating).
  • the mordenite content of the support thus obtained must be greater than 40% and preferably greater than 60% by weight.
  • At least one hydrogenating metal from group VIII preferably chosen from the group formed by platinum, palladium, and nickel, is then deposited on this support, either in the form of a tetramine complex by cation exchange, or in the form of acid.
  • hexachloroplatinic in the case of platinum or either in the form of palladium chloride by anion exchange.
  • the content by weight is between 0.05 and 1% and preferably between 0.1 and 0.6%.
  • the weight content is between 0.1 and 10% and preferably between 0.2 and 5%.
  • the effluent obtained at the exit from the isomerization zone has an octane number sufficiently high to be incorporated into the gasoline fractions after stabilization and comprises a maximum benzene content generally equal to 0.1% by weight. Preferably, it is completely free of benzene.
  • the single figure shows an arrangement of the process according to the invention, in which the hydrogenation and the isomerization are carried out in two separate reactors (or units).
  • the stabilized reformate (1) is sent to a distillation column (6), from which a heavy reformate (3) is extracted at the bottom which can be used directly in the gasoline fractions and at the head a light reformate (2).
  • the latter is sent to a hydrogenation unit (7), alone or after mixing with at least one part (9) of a C5-C6 cut from direct distillation.
  • the cut obtained (4) is treated in an isomerization unit (8) giving the final product (5) which, after stabilization, can be incorporated into the gasoline fractions.
  • at least part (10) of the C5-C6 direct distillation section is mixed with the saturated light reformate (4) just before the isomerization unit (10).
  • the light reformate obtained after distillation at 85 ° C, containing 21.5% of benzene and having an octane number of 80.3 is mixed in an amount of 50% by weight with a C5-C6 cut of direct distillation containing 0.7 % of benzene and having an octane number of 65.
  • the compositions of these 2 products are listed in Table I.
  • the charge from the mixture, the composition of which also appears in Table I, is sent to a hydrogenation unit at a temperature of 110 ° C, and a pressure of 40 bar.
  • the hydrogen to hydrocarbons molar ratio contained in the charge is equal to 0.85, and the liquid space velocity is equal to 4 h ⁇ 1.
  • the catalyst used in the hydrogenation section consists of 15% of Ni deposited on alumina.
  • the effluent from the hydrogenation unit no longer contains benzene but has an octane number of 70.9. It is then sent to an isomerization unit operating at a temperature of 260 ° C, a pressure of 30 bar with an LHSV equal to 2 h ⁇ 1 and a hydrogen to hydrocarbon molar ratio of the charge of the isomerization unit equal to 4.
  • the effluent leaving the isomerization unit has the composition given in Table I; he ...
  • the hydrogen to hydrocarbons molar ratio contained in the charge is equal to 0.85, and the liquid space velocity is equal to 4 h ⁇ 1.
  • the catalyst used in the hydrogenation section consists of 15% of Ni deposited on alumina.
  • the effluent from the hydrogenation unit no longer contains benzene but has an octane number of 76.5. It is then mixed in an amount of 50% by weight with a C5-C6 cut of direct distillation containing 0.7% of benzene and having an octane number of 65.
  • the composition of this cut as well as the composition of the mixture which constitutes the load of the isomerization unit are given in table II.
  • the isomerization unit operates at a temperature of 260 ° C., a pressure of 30 bar with an LHSV equal to 2 and a hydrogen to hydrocarbon molar ratio of the charge equal to 4.
  • the effluent leaving the isomerization unit has the composition given in Table II; it no longer contains benzene and has an octane number of 78.1. This effluent can be directly incorporated into the gasoline fractions after stabilization.

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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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP93400021A 1992-01-15 1993-01-07 Erniedrigung des Benzolgehaltes von Benzinen Expired - Lifetime EP0552070B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR9200435 1992-01-15
FR9200435A FR2686094B1 (fr) 1992-01-15 1992-01-15 Production de base pour carburant exempt de benzene, presentant un indice d'octane eleve.
FR9209758 1992-08-04
FR929209758A FR2694565B1 (fr) 1992-08-04 1992-08-04 Réduction de la teneur en benzène dans les essences.

Publications (2)

Publication Number Publication Date
EP0552070A1 true EP0552070A1 (de) 1993-07-21
EP0552070B1 EP0552070B1 (de) 1999-08-18

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EP93400021A Expired - Lifetime EP0552070B1 (de) 1992-01-15 1993-01-07 Erniedrigung des Benzolgehaltes von Benzinen

Country Status (6)

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EP (1) EP0552070B1 (de)
CA (1) CA2087385A1 (de)
DE (1) DE69326030T2 (de)
ES (1) ES2137974T3 (de)
MY (1) MY109122A (de)
TW (1) TW218377B (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2714388A1 (fr) * 1993-12-29 1995-06-30 Inst Francais Du Petrole Procédé de réduction de la teneur en benzène dans les essences.
US5599997A (en) * 1995-03-14 1997-02-04 Chemical Research & Licensing Company Process for the production of cyclohexyl amine
EP0781830A1 (de) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Verfahren zur Erniedrigung des Gehaltes von Benzol und von leichten ungesättigten Verbindungen in Kohlenwasserstofffraktionen
EP0781829A1 (de) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Verfahren und Vorrichtung zur selektiven Hydrierung durch katalytische Distillation
EP0781831A1 (de) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Verfahren zur Erniedrigung des Gehaltes von Benzol und von leichten ungesättigten Verbindungen in Kohlenwasserstofffraktionen
US5773670A (en) * 1995-03-06 1998-06-30 Gildert; Gary R. Hydrogenation of unsaturated cyclic compounds
FR2776667A1 (fr) * 1998-03-31 1999-10-01 Total Raffinage Distribution Procede et dispositif d'isomerisation d'essences a teneur elevee en benzene
EP0953626A1 (de) * 1998-04-27 1999-11-03 FE Forschungs & Entwicklung GmbH Verfahren zur Herstellung eines benzolarmen, hochoktanigen Kohlenwasserstoffgemischs
US6855853B2 (en) 2002-09-18 2005-02-15 Catalytic Distillation Technologies Process for the production of low benzene gasoline
US11697777B2 (en) 2019-08-02 2023-07-11 Abu Dhabi Oil Refining Company—Takreer Single reactor process for benzene-saturation/isomertzation of light reformates

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009002A (en) * 1960-06-20 1961-11-14 Phillips Petroleum Co High purity cyclohexane from natural cyclohexane-containing fraction
FR2133611A1 (de) * 1971-04-19 1972-12-01 British Petroleum Co
US5003118A (en) * 1989-12-29 1991-03-26 Uop Isomerization of benzene-containing feedstocks

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009002A (en) * 1960-06-20 1961-11-14 Phillips Petroleum Co High purity cyclohexane from natural cyclohexane-containing fraction
FR2133611A1 (de) * 1971-04-19 1972-12-01 British Petroleum Co
US5003118A (en) * 1989-12-29 1991-03-26 Uop Isomerization of benzene-containing feedstocks

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2714388A1 (fr) * 1993-12-29 1995-06-30 Inst Francais Du Petrole Procédé de réduction de la teneur en benzène dans les essences.
EP0661370A1 (de) * 1993-12-29 1995-07-05 Institut Français du Pétrole Katalysator zur Erniedrigung des Benzolgehaltes von Benzinen
US5578196A (en) * 1993-12-29 1996-11-26 Institut Francais Du Petrole Process for reducing the benzene content of petrols
US5773670A (en) * 1995-03-06 1998-06-30 Gildert; Gary R. Hydrogenation of unsaturated cyclic compounds
US5599997A (en) * 1995-03-14 1997-02-04 Chemical Research & Licensing Company Process for the production of cyclohexyl amine
EP0781829A1 (de) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Verfahren und Vorrichtung zur selektiven Hydrierung durch katalytische Distillation
US6048450A (en) * 1995-12-27 2000-04-11 Institut Francais Du Petrole Process for the selective reduction to the content of benzene and light unsaturated compounds in a hydrocarbon cut
FR2743079A1 (fr) * 1995-12-27 1997-07-04 Inst Francais Du Petrole Procede et dispositif d'hydrogenation selective par distillation catalytique comportant une zone reactionnelle a co-courant ascendant liquide-gaz
FR2743081A1 (fr) * 1995-12-27 1997-07-04 Inst Francais Du Petrole Procede de reduction selective de la teneur en benzene et en composes insatures legers d'une coupe d'hydrocarbures
FR2743080A1 (fr) * 1995-12-27 1997-07-04 Inst Francais Du Petrole Procede de reduction selective de la teneur en benzene et en composes insatures legers d'une coupe d'hydrocarbures
EP0781830A1 (de) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Verfahren zur Erniedrigung des Gehaltes von Benzol und von leichten ungesättigten Verbindungen in Kohlenwasserstofffraktionen
US5817227A (en) * 1995-12-27 1998-10-06 Institut Francais Du Petrole Process for the selective reduction to the content of benzene and light unsaturated compounds in a hydrocarbon cut
US5888355A (en) * 1995-12-27 1999-03-30 Institut Francais Du Petrole Apparatus comprising a catalytic distillation zone comprising a reaction zone with distribution of hydrogen
US6084141A (en) * 1995-12-27 2000-07-04 Institut Français Du Petrole Hydrogenation process comprising a catalytic distillation zone comprising a reaction zone with distribution of hydrogen
EP0781831A1 (de) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Verfahren zur Erniedrigung des Gehaltes von Benzol und von leichten ungesättigten Verbindungen in Kohlenwasserstofffraktionen
EP0949317A1 (de) * 1998-03-31 1999-10-13 Total Raffinage Distribution S.A. Verfahren und Vorrichtung zur Isomerizierung von Benzinen mit hohem Benzolgehalt
FR2776667A1 (fr) * 1998-03-31 1999-10-01 Total Raffinage Distribution Procede et dispositif d'isomerisation d'essences a teneur elevee en benzene
US6416657B1 (en) 1998-03-31 2002-07-09 Total Raffinage Distribution S.A. Method for the isomerization of gasoline with a high benzene content
US6881385B2 (en) 1998-03-31 2005-04-19 Total Raffinage Distribution S.A. Device for the isomerization of gasoline with a high benzene content
EP0953626A1 (de) * 1998-04-27 1999-11-03 FE Forschungs & Entwicklung GmbH Verfahren zur Herstellung eines benzolarmen, hochoktanigen Kohlenwasserstoffgemischs
US6855853B2 (en) 2002-09-18 2005-02-15 Catalytic Distillation Technologies Process for the production of low benzene gasoline
US7175754B2 (en) 2002-09-18 2007-02-13 Catalytic Distillation Technologies Process for the production of low benzene gasoline
US11697777B2 (en) 2019-08-02 2023-07-11 Abu Dhabi Oil Refining Company—Takreer Single reactor process for benzene-saturation/isomertzation of light reformates

Also Published As

Publication number Publication date
DE69326030D1 (de) 1999-09-23
ES2137974T3 (es) 2000-01-01
MY109122A (en) 1996-12-31
EP0552070B1 (de) 1999-08-18
CA2087385A1 (fr) 1993-07-16
DE69326030T2 (de) 2000-01-05
TW218377B (de) 1994-01-01

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