EP0685552B2 - Procédé et utilisation d'une installation pour le traitement par hydrogénation sélective d'une essence de craquage catalique - Google Patents

Procédé et utilisation d'une installation pour le traitement par hydrogénation sélective d'une essence de craquage catalique Download PDF

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Publication number
EP0685552B2
EP0685552B2 EP95401244A EP95401244A EP0685552B2 EP 0685552 B2 EP0685552 B2 EP 0685552B2 EP 95401244 A EP95401244 A EP 95401244A EP 95401244 A EP95401244 A EP 95401244A EP 0685552 B2 EP0685552 B2 EP 0685552B2
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EP
European Patent Office
Prior art keywords
process according
cut
selective hydrogenation
catalytic cracking
gasoline
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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.)
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EP95401244A
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German (de)
English (en)
French (fr)
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EP0685552B1 (fr
EP0685552A1 (fr
Inventor
Jean Cosyns
Charles Cameron
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Application filed by IFP Energies Nouvelles IFPEN filed Critical IFP Energies Nouvelles IFPEN
Priority to DE1995614957 priority Critical patent/DE69514957T3/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
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
    • C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
    • C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
    • 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
    • C10G69/04—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 catalytic cracking in the absence of hydrogen

Definitions

  • the decrease in the concentration of olefins is often obtained by etherification of 2-methyl butenes to tertioamylmethylether or sometimes 2-methylpentenes and 3-methylpentene-2 in tertiohexylmethylether.
  • Etherification is thus an elegant way of reducing the content of olefins while transforming them into High octane research and engine ethers.
  • the subject of the invention is a method as described in claim 1.
  • the catalyst must contain palladium (0.1 to 1% by weight, and preferably 0.2-0.5% by weight) deposited on a support containing at least 50% of alumina, and preferably at least 90%, and advantageously this support is pure alumina.
  • Another metal can be combined to form a bimetallic catalyst, such as gold (Au / Pd expressed by weight greater than or equal to 0.1 and less than 1, and preferably between 0.2 and 0.8).
  • a bimetallic catalyst such as gold (Au / Pd expressed by weight greater than or equal to 0.1 and less than 1, and preferably between 0.2 and 0.8).
  • the catalyst thus essentially comprises palladium or palladium and gold.
  • the choice of operating conditions is particularly important. We will generally operate under pressure in the presence of a quantity of hydrogen in small excess relative to the stoichiometric value required to hydrogenate diolefins.
  • the hydrogen and the charge to be treated are injected in ascending or descending currents in a reactor preferably with a fixed bed of catalyst.
  • the temperature is generally between 80 and 200 ° C, in particular between 130 and 200 ° C and preferably between 150 and 170 ° C.
  • the pressure is sufficient to keep most of the gasoline to be treated in the liquid phase in the reactor, more generally between 4 and 25 bar and preferably above 10 bar.
  • Advantageous pressure is between 10-20 bar, and preferably between 12-16 bar.
  • the space speed is in these conditions established between 1-10 h -1 , preferably less than 10 h -1 and better between 4 and less than -10 h -1 .
  • the invention relates exclusively to catalytic cracking gasolines.
  • the essence cut of catalytic cracking generally contains from 15 to 40% of olefins (olefins, diolefins and cycloolefins) with a content of conjugated diolefins less than 5% and generally not more than 4%.
  • the content of dienes is reduced to less than 1000 ppm.
  • the diene content in cuts C5 and C6 after selective hydrogenation is generally reduced to less than 250 ppm.
  • the content of cyclopentadiene in a catalytic cracked gasoline is less than 1% by weight, and generally less than 0.5% by weight, whereas it can be 20% by weight in a steam cracking gasoline.
  • the mercaptan content is between 1 and 300 ppm, and generally less than 200 ppm.
  • the invention also relates to the use of an installation for a process for the treatment by selective hydrogenation of a catalytic cracking gasoline as described in claim 13 comprising a catalytic cracking unit followed by a fractionation unit for separating fraction C 3 -210 ° C, a debutanizer, then a separation unit chosen from a depentanizer and a dehexanizer, said installation comprising a selective hydrogenation unit placed between the debutanizer and the separation unit.
  • FIG 1 shows schematically the process and the installation used according to the invention.
  • an effluent leaves which is fractionated in a unit 2 for fractionation into a diesel cut (LCO), a heavy cut (HCO) and a cut containing the hydrocarbons.
  • LCO diesel cut
  • HCO heavy cut
  • the C 5 -180 ° C cut obtained (or the C 5 -160 ° C or C 5 -210 ° C cut depending on the fractionation carried out), called the C 5+ catalytic cracking gasoline cut, is introduced into a zone (or l 'unit) 4 of selective hydrogenation according to the invention, hydrogen is also introduced for example by line 5.
  • the hydrogenated cut obtained enters the separation unit 6 which is a depentanizer (separation C 5 ) or a dehexanizer (separation C 5 -C 6 ).
  • a C 5 fraction or a C 5 -C 6 fraction is therefore obtained which is advantageously sent to the etherification unit, and a C 7+ fraction sent to petrol storage.
  • the catalytic hydrogenation reactor 10 comprises a reaction zone catalyst through which the entire charge and the quantity of hydrogen required to carry out the reactions desired.
  • the catalytic hydrogenation reactor 10 is arranged so particular as shown in Figure 2, namely two catalytic zones 11 and 12, the first 11 being crossed by the liquid charge (and a quantity of hydrogen, supplied by a tube 5, less than the necessary stoichiometry to convert all the diolefins into mono olefins) entering via the pipe 15; in this first zone, the softening also takes place; the second 12 receiving the liquid charge coming from the first zone (as well as the rest hydrogen i.e.
  • the proportion of the first zone (by volume) is at most equal to 50% of the sum of the 2 zones and preferably 15 to 30%.
  • the hydrogenation unit can operate at pressures lower than those required by the debutanizer and since the depentaniser (or dehexanizer) does not require a pressure of 13 to 15 bar, the circulation charge through the installation is obtained by slight depressurization at the outlet of the hydrogenation unit. This allows operation without additional pumps.
  • the high temperature of the debutanizer base and the high activity of the catalysts used in the invention allow the selective hydrogenation unit of C 5+ cut of catalytic cracking to operate without a charge preheating oven and to be very compact. . This leads to a unit with low investment and great flexibility which gives it unique advantages.
  • the new process according to the invention of selective hydrogenation catalytic cracked gasoline does not require charge or recycling pumps or a preheating oven.
  • the new process offers flexibility much larger by isolating the catalyst from the distillation column, allowing the catalyst to be replaced without stop downstream units. It also allows the catalyst to provide more activity, thanks to higher temperatures and pressures than those obtained in the depentaniser.
  • the new process makes it possible to simultaneously treat cuts C 5 , C 6 and C 7 -210 ° C. This therefore allows the pretreatment before etherification of cuts C 5 and C 6 by means of flexible and inexpensive selective hydrogenation. This process makes it possible to obtain the maximum of precursors of C 5 and C 6 ethers and moreover decreases the quantity of antioxidants to be used in the treated gasoline.
  • ethers such as tertioamyl ether for example. It also improves the quality of the gasoline produced, which has a better oxidation stability as well as an improved octane number.
  • catalyst LD265 from the company Procatalyse containing 0.3% by weight of palladium supported on alumina in a stainless steel tube 1.9 cm in diameter. This catalyst is commonly used for the hydrogenation of cuts C 3 and C 4 of FCC and steam cracking.
  • the catalyst is activated by reduction under hydrogen at a flow rate of 30 l / h for 5 hours at 200 ° C.
  • the installation is cooled under nitrogen to 150 ° C. before injecting the FCC gasoline having the properties indicated in table 1.
  • the reactor is then pressurized to 14 bar and the gasoline is injected into the bottom of the reactor (100 cm 3 / hour therefore a VVH of 1 h -1 ).
  • the effect of the space velocity is determined by increasing the WH at 5 h -1 (example 2) then at 10 h -1 (example 3) while keeping the H 2 / diolefin molar ratio at 1.6.
  • Example 4 The effect of reducing the H 2 / diolefin molar ratio is shown in Example 4 where this ratio is 1.4 and the liquid VVH is 10 h -1 .
  • the catalytic zone is cut into two separate beds, therefore 25 cm 3 in the first zone and 75 cm 3 of LD265 in the second.
  • the procedure is as previously described in Example 4 except the quantity of hydrogen injected into the reactor with the feed represents a molar ratio of 0.9.
  • An injection device between the two beds makes it possible to add an additional quantity of hydrogen corresponding to a molar ratio of 0.5 relative to the quantity of diolefins initially present in the raw gasoline of FCC, example 5.
  • staged addition of hydrogen under the conditions recommended in the present invention makes it possible not only to improve the conversion of the diolefins (show by increasing the induction period) but also to increase the amount of precursors of TAME (ie 2-methylbutene-1 and 2-methylbutene-2) and to soften, at least partially, the essence of FCC.

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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)
EP95401244A 1994-06-01 1995-05-29 Procédé et utilisation d'une installation pour le traitement par hydrogénation sélective d'une essence de craquage catalique Expired - Lifetime EP0685552B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1995614957 DE69514957T3 (de) 1994-06-01 1995-05-29 Verfahren und Verwendung einer Anlage für die selektive Hydrierung von katalytischen Crackbenzinen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9406708 1994-06-01
FR9406708A FR2720754B1 (fr) 1994-06-01 1994-06-01 Procédé et installation pour le traitement par hydrogénation sélective d'une essence de craquage catalytique.

Publications (3)

Publication Number Publication Date
EP0685552A1 EP0685552A1 (fr) 1995-12-06
EP0685552B1 EP0685552B1 (fr) 2000-02-09
EP0685552B2 true EP0685552B2 (fr) 2002-11-27

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ID=9463769

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EP95401244A Expired - Lifetime EP0685552B2 (fr) 1994-06-01 1995-05-29 Procédé et utilisation d'une installation pour le traitement par hydrogénation sélective d'une essence de craquage catalique

Country Status (4)

Country Link
EP (1) EP0685552B2 (es)
DE (1) DE69514957T3 (es)
ES (1) ES2144587T5 (es)
FR (1) FR2720754B1 (es)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19608241A1 (de) * 1996-03-04 1997-09-18 Basf Ag Verfahren zur selektiven Hydrierung von Dienen
US6709639B1 (en) 1996-09-24 2004-03-23 Institut Francais Du Petrole Apparatus for purification of raw gasoline from catalytic cracking
FR2753718B1 (fr) * 1996-09-24 1999-05-14 Procede et installation de purification d'essences brutes de craquage catalytique
FR2753717B1 (fr) 1996-09-24 1998-10-30 Procede et installation pour la production d'essences de craquage catalytique a faible teneur en soufre
DE69812225T2 (de) * 1997-06-09 2003-12-04 Institut Francais Du Petrole, Rueil Malmaison Verfahren zur Behandlung von Diolefinen, Styrolverbindungen und gegebenenfalls Mercaptanen enthaltenden Benzinschnitten
FR2764210B1 (fr) * 1997-06-09 1999-07-16 Inst Francais Du Petrole Catalyseur d'hydrogenation selective utilisable pour le traitement des coupes essences contenant des diolefines et des composes styreniques
FR2764299B1 (fr) * 1997-06-09 1999-07-16 Inst Francais Du Petrole Procede de traitement de coupes essences contenant des diolefines, des composes styreniques et des mercaptans
FR2797639B1 (fr) 1999-08-19 2001-09-21 Inst Francais Du Petrole Procede de production d'essences a faible teneur en soufre
FR2807061B1 (fr) * 2000-03-29 2002-05-31 Inst Francais Du Petrole Procede de desulfuration d'essence comprenant une desulfuration des fractions lourde et intermediaire issues d'un fractionnement en au moins trois coupes
FR2935389B1 (fr) 2008-09-04 2012-05-11 Inst Francais Du Petrole Procede d'hydrogenation selective mettant en oeuvre un catalyseur sulfure de composition specifique
FR2963359B1 (fr) 2010-07-29 2012-07-27 IFP Energies Nouvelles Procede d'hydrogenation selective d'une coupe essence en presence d'un catalyseur sulfure supporte prepare au moyen d'au moins un oligosaccharide cyclique
CN104560135B (zh) * 2013-10-24 2016-08-17 中国石油化工股份有限公司 一种重整生成油的加氢方法
WO2017003788A1 (en) * 2015-06-30 2017-01-05 Uop Llc Process and apparatus for selectively hydrogenating diolefins
CN114763493B (zh) * 2021-01-13 2024-01-12 中国石油化工股份有限公司 利用碳五抽余油生产汽油调和油方法和系统

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470085A (en) † 1967-11-20 1969-09-30 Universal Oil Prod Co Method for stabilizing pyrolysis gasoline
US5254789A (en) † 1990-02-08 1993-10-19 Uop Process for isomerizing olefins in gasoline streams
US5266188A (en) † 1991-04-22 1993-11-30 Amoco Corporation Selective hydrotreating

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1346778A (en) * 1971-02-11 1974-02-13 British Petroleum Co Selective hydrogenation of gasolines
GB1565754A (en) * 1978-03-08 1980-04-23 British Petroleum Co Selective hydrogenation
FR2460989A1 (fr) * 1979-07-06 1981-01-30 Inst Francais Du Petrole Procede de purification d'une coupe d'hydrocarbures aromatiques contenant des hydrocarbures insatures olefiniques et acetyleniques
FR2482953A1 (fr) * 1980-05-22 1981-11-27 Inst Francais Du Petrole Procede d'hydrogenation selective d'une di-olefine dans un melange d'hydrocarbures renfermant au moins 4 atomes de carbone et contenant une olefine -a
FR2686617B1 (fr) * 1992-01-28 1994-03-18 Institut Francais Petrole Procede d'hydrogenation selective de charge hydrocarbonee avec des lets catalytiques mis en óoeuvre successivement.
FR2689419B1 (fr) * 1992-04-02 1994-09-30 Inst Francais Du Petrole Catalyseur contenant un métal du groupe VIII et un métal de groupe III a déposés sur un support, applicable à l'hydrogénation sélective des hydrocarbures.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470085A (en) † 1967-11-20 1969-09-30 Universal Oil Prod Co Method for stabilizing pyrolysis gasoline
US5254789A (en) † 1990-02-08 1993-10-19 Uop Process for isomerizing olefins in gasoline streams
US5266188A (en) † 1991-04-22 1993-11-30 Amoco Corporation Selective hydrotreating

Also Published As

Publication number Publication date
EP0685552B1 (fr) 2000-02-09
ES2144587T3 (es) 2000-06-16
FR2720754A1 (fr) 1995-12-08
EP0685552A1 (fr) 1995-12-06
ES2144587T5 (es) 2003-06-16
DE69514957T2 (de) 2000-10-12
DE69514957D1 (de) 2000-03-16
DE69514957T3 (de) 2011-08-18
FR2720754B1 (fr) 1996-07-26

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