EP0334742B1 - Verfahren zur selektiven Hydrierung eines normal gasförmigen Einsatzes, der Ethylen, Acetylen und Benzin enthält - Google Patents

Verfahren zur selektiven Hydrierung eines normal gasförmigen Einsatzes, der Ethylen, Acetylen und Benzin enthält Download PDF

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Publication number
EP0334742B1
EP0334742B1 EP89400781A EP89400781A EP0334742B1 EP 0334742 B1 EP0334742 B1 EP 0334742B1 EP 89400781 A EP89400781 A EP 89400781A EP 89400781 A EP89400781 A EP 89400781A EP 0334742 B1 EP0334742 B1 EP 0334742B1
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Prior art keywords
weight
hydrocarbons
process according
cut
hydrogenated
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French (fr)
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EP0334742A1 (de
Inventor
Jean Cosyns
Jean-Paul Boitiaux
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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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

Definitions

  • Thermal conversion processes such as steam cracking, for example, produce olefinic compounds of interest for petrochemicals, but their recovery requires a selective hydrogenation of the acetylene and diolefinic impurities co-produced by these processes.
  • the catalysts used in this hydrogenation are quickly fouled by these polymerization products and the cycle times are therefore disadvantageously very short.
  • Patent application EP-A-135,442 describes a process for the selective hydrogenation of acetylene contained in a mixture of acetylene and ethylene in which said mixture is circulated through a fixed bed of supported palladium catalyst, characterized in that one operates in the presence of a liquid phase containing at least one aromatic hydrocarbon and at least one amino compound dissolved in said liquid phase.
  • US Pat. No. 3,537,981 describes a process for stabilizing pyrolysis gasolines, a two-step process in which the hydrogenation of diolefins and styrenes is carried out and part of the effluents from the first reaction zone are recycled .
  • the object of the present invention is the development of a new process for selective catalytic hydrogenation in the liquid phase of a normally gaseous hydrocarbon charge (that is to say in vapor form at normal temperature and pressure ) containing in particular acetylene, ethylene, gasoline (hydrocarbons C 5 to C 9 ), the liquid phase (or liquid diluent), in the presence of which (which) one operates, comprising at least a portion of the condensable fraction of said charge, that is to say at least part of the gasoline cut (C 5 - C 9 ) hydrogenated, condensed and recycled of said charge.
  • This process allows both the production of a hydrogenated petrol cut and the production of practically pure ethylene (i.e. practically free of acetylene).
  • This hydrogenated cut can also contain a small amount of carbon monoxide, for example between 0.01 and 1% by weight, preferably between 0.02 and 0.2% by weight.
  • the charge to be hydrogenated can, for example, consist of the effluent from an ethane steam cracker.
  • the presence of hydrogen in the feed to be hydrogenated can advantageously avoid working with an external source of hydrogen.
  • the method according to the invention allows more satisfactory operation of the installation, the cycle times being increased in significant proportions and, surprisingly, the quality of the liquid which is recycled to the hydrogenation reactor is improved.
  • the hydrogenated cuts produced in the process meet the most stringent specifications: indeed, the C 2 cut (after hydrogenation and separation) can easily contain less than 5 ppm by weight of acetylene, and the gasoline cut (after hydrogenation and separation) has a "Maleic Anhydride Value" (MAV), which is a measure of the content of conjugated diolefins, determined according to UOP standard No. 356, preferably less than 3.
  • MAV Meleic Anhydride Value
  • the hydrogenation catalyst consists of at least supported palladium.
  • Palladium is generally deposited in an amount of 0.01 to 1% by weight on a suitable support such as, for example, alumina or silica or a mixture of these two constituents.
  • Palladium can be associated with at least one additional metal chosen, for example, from the group formed by silver and gold, with contents which may generally be between 0.01 and 1% of the weight of catalyst.
  • the Au / Pd or Ag / Pd or (Au + Ag) / Pd weight ratio is less than 1.
  • the hydrogenation can be carried out in at least one reactor in which the catalyst is preferably placed in a fixed bed.
  • Figure 1 shows a non-limiting example of application of the invention.
  • the (normally gaseous) cup to be hydrogenated (1) for example the effluent from an ethane steam cracker
  • the liquid diluent (8) and possibly hydrogen (13) in the case where the cup to be hydrogenated does not contain or contains only a very small amount
  • the effluent from said reactor (4) is sent, via line (11), to a distillation column (5) making it possible to separate a gas cut at the top (7) (which contains excess hydrogen and hydrocarbons with less than five carbon atoms, for example methane, the incondensable gas containing excess hydrogen, hydrogenated C 2 , C 3 and C 4 cuts (i.e.
  • This hydrogenated and sampled petrol cut can be used directly as fuel, therefore without transformation, because it contains an extremely small amount of diolefins and therefore of undesirable gums, diolefins which are in fact mainly hydrogenated during the process according to the invention. .
  • the entire catalyst is permanently sprayed with the liquid phase (or liquid diluent) constituting the flow (8) and entering the reactor (4) towards its top.
  • the fresh charge to be hydrogenated can be injected towards the top of the reactor (4), via the pipe (2) and / or halfway up the catalyst by a pipe (3).
  • the recycled liquid (or liquid diluent) phase generally contains at least 25%, preferably 50 to 85% and, even more preferably, 60 to 75% by weight of aromatic hydrocarbons (styrene is not included in the aromatic hydrocarbons).
  • the ratio, at the inlet of the reactor (4), between the weight flow rate of recycled liquid and the weight flow rate of gaseous feed to be hydrogenated is usually between 0.5 and 20, preferably between 1.0 and 10 and, even more preferably, between 1.5 and 5.
  • the catalyst contains 500 ppm by weight of palladium deposited on an alumina support with a specific surface area equal to 9 m 2 / g and a pore volume equal to 0.5 cm 3 / g.
  • the catalyst is placed in a fixed bed in a tubular reactor.
  • the catalyst is rapidly deactivated by fouling and that the hydrogenation reaction is insufficient: in fact, on the one hand, the conversion of acetylene is only 80% after 15 days of operation (acetylene content in cut C 2 : 1.0% by weight at the inlet, 0.2% by weight at the outlet) and, on the other hand, the conversion of the diolefins (and of styrene ) has clearly decreased after 15 days of operation (content of diolefins (and styrene) in the petrol cut: 0.3% by weight after 2 days of operation, 6.0% by weight after 15 days of operation).
  • This catalyst is placed in a fixed bed in a tubular reactor; the unit also includes a distillation column containing 10 trays, the operation of this column is such that the gasoline cut (C 5 - C 9 ) and therefore all the benzene from the feed is found in the bottom racking and at least most of the C 4 - (hydrocarbons with four carbon atoms at most) is found at the top.
  • the bottom liquid is taken up by a pump and constitutes the liquid inlet of the reactor, the cut to be hydrogenated being mixed with this liquid at the inlet of the reactor.
  • the loop is filled with toluene and a small continuous purge on the liquid drawn off at the bottom of the column is carried out during operation, in order to have a constant liquid level in the column.
  • the weight flow rate of recycled liquid is equal to approximately 2.8 times the weight flow rate of gaseous feed to be hydrogenated.
  • Samples to analyze the purged liquid were taken and give the results presented in FIG. 2 (content (% weight) of toluene (continuous curve) and benzene (discontinuous curve) in the withdrawal liquid as a function of time (hour) ). It is noted that after 200 hours the liquid phase has a constant composition which corresponds to the condensable part of the cup to be hydrogenated.
  • the weight composition of the gaseous and liquid effluents respectively at the head and at the bottom of the column after 10 days and after 2 months of operation is indicated respectively in Tables 8 and 9.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (10)

  1. Verfahren zur Herstellung eines hydrierten Benzinschnitts sowie von reinem Äthylen aus einer normalerweise gasförmigen Charge, die zumindest Äthylen, Azetylen und 1 bis 20 Gew.-% eines Benzinschnitts (C5 - C9-Kohlenwasserstoffe) enthält und ferner aromatische Kohlenwasserstoffe sowie Diolefine und/oder Styrol enthält, gekennzeichnet durch folgende Verfahrensstufen:
    a) Selktive Hydrierung dieser Charge in Dampfform durch in Kontakt bringen mit einem Katalysator, der zumindest Palladium auf einem Träger aufweist, wobei in Anwesenheit eines flüssigen Verdünnungsmittels gearbeitet wird, das zumindest zum Teil aus dem zu hydrierenden Benzinschnitt besteht, anschließendes Kondensieren und Rezyklisieren der Charge, wobei die Hydrierung bei einem Gesamtdruck zwischen 10 und 50 bar, sowie einer Temperatur von 10 bis 150°C durchgeführt wird und eine Raumgeschwindigkeit, ausgedrückt durch den Volumendurchsatz der zu hydrierenden Charge pro Volumen Katalysator und pro Stunde, zwischen 500 und 20 000 und ferner der Volumendurchsatz der zu rezyklisierenden Flüssigkeit pro Volumenkatalysator und pro Stunde 1 bis 15 beträgt, sowie das Verhältnis zwischen dem gewichtsmäßigem Durchsatz der genannten Flüssigkeit und dem gewichtsmäßigen Durchsatz der zu hydrierenden Charge 0,5 bis 20 beträgt,
    b)Fraktionierung des ausströmenden Effluents der Hydrierungsstufe in einen gasförmigen Schnitt, der die C1- C4- Kohlenwasserstoffe enthält und einen Benzinschnitt, der die C5-C9-Kohlenwasserstoffe enthält,
    c) Rezyklisierung eines Teils des Benzinschnitts in den Hydrierungsreaktor.
  2. Verfahren nach Anspruch 1,
    dadurch gekennzeichnet,
    daß die genannte Charge 0 bis 60 Gew.-% Wasserstoff, 0 bis 40 Gew.-% Methan, 25 bis 80 Gew.-% C2- Kohlenwasserstoffe und vorzugsweise 0,1 bis 5 Gew.-% Azetylen sowie 15 bis 75 Gew.-% Äthylen, 0 bis 40 Gew.-% C3- Kohlenwasserstoffe und 0 bis 10 Gew.-% C4- Kohlenwasserstoffe, enthält.
  3. Verfahren nach Anspruch 1,
    dadurch gekennzeichnet,
    daß die genannte Charge 1 bis 2, 5 Gew.-% Kohlenwasserstoffe, 15 bis 30 Gew.-% Methan, 30 bis 45 Gew.-% C2-Kohlenwasserstoffe und insbesondere 0,2 bis 2 Gew.-% Azetylen und 20 bis 35 Gew.-% Äthylen, 15 bis 35 Gew.-% C3-Kohlenwasserstoffe, 1 bis 6 Gew.-% C4- Kohlenwasserstoffe und 1 bis 7 Gew.-% Benzin,enthält.
  4. Verfahren nach mindestens einem der Ansprüche 1 bis 3,
    dadurch gekennzeichnet,
    daß die genannte Charge ein Effluent einer Ethan-Dampfkrackung ist.
  5. Verfahren nach mindestens einem der Ansprüche 1 bis 4,
    dadurch gekennzeichnet,
    daß das genannte Verdünnungsmittel zumindest 25 Gew.-% an aromatischen Kohlenwasserstoffen enthält.
  6. Verfahren nach Anspruch 5,
    dadurch gekennzeichnet,
    daß das genannte flüssige Verdünnungsmittel 50 bis 85 Gew.-% an aromatischen Kohlenwasserstoffen enthält.
  7. Verfahren nach mindestens einem der Ansprüche 1 bis 6,
    dadurch gekennzeichnet,
    daß der genannte Katalysator aus Palladium und zumindest einem weiteren Metall der Gruppe, die aus Gold und Silber besteht, enthält, wobei das Gemisch aus Palladium und zumindest einem weiteren zusätzlichen Metall auf zumindest einem Träger angeordnet ist, der der Gruppe angehört, die aus Aluminiumoxid und Siliciumdioxid besteht.
  8. Verfahren nach mindestens einem der Ansprüche 1 bis 7,
    dadurch gekennzeichnet,
    daß das Verhältnis zwischen dem Gewichtsdurchsatz des genannten flüssigen Verdünnungsmittels und dem gewichtsmäßigem Durchsatz der zu hydrierenden Charge) 0,5 bis 20 beträgt.
  9. Verfahren nach Anspruch 8,
    dadurch gekennzeichnet,
    daß das genannte Verhältnis 1 bis 10 beträgt.
  10. Verwendung des Verfahrens nach zumindest einem der Ansprüche 1 bis 9, zur Herstellung von Äthylen sowie zur Herstellung von Benzin.
EP89400781A 1988-03-23 1989-03-20 Verfahren zur selektiven Hydrierung eines normal gasförmigen Einsatzes, der Ethylen, Acetylen und Benzin enthält Expired - Lifetime EP0334742B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT89400781T ATE81666T1 (de) 1988-03-23 1989-03-20 Verfahren zur selektiven hydrierung eines normal gasfoermigen einsatzes, der ethylen, acetylen und benzin enthaelt.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8803909A FR2629094B1 (fr) 1988-03-23 1988-03-23 Procede d'hydrogenation catalytique selective en phase liquide d'une charge normalement gazeuse contenant de l'ethylene, de l'acetylene et de l'essence
FR8803909 1988-03-23

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EP0334742A1 EP0334742A1 (de) 1989-09-27
EP0334742B1 true EP0334742B1 (de) 1992-10-21

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EP89400781A Expired - Lifetime EP0334742B1 (de) 1988-03-23 1989-03-20 Verfahren zur selektiven Hydrierung eines normal gasförmigen Einsatzes, der Ethylen, Acetylen und Benzin enthält

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US (1) US5059732A (de)
EP (1) EP0334742B1 (de)
JP (1) JP2736799B2 (de)
AT (1) ATE81666T1 (de)
CA (1) CA1316947C (de)
DE (1) DE68903239T2 (de)
FR (1) FR2629094B1 (de)

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EP3013778A1 (de) 2013-06-25 2016-05-04 Dow Technology Investments LLC Selektives hydrierungsverfahren
CN103819298B (zh) * 2014-03-07 2015-09-02 中石化上海工程有限公司 碳二馏分选择性加氢反应方法
CN105585665B (zh) * 2014-10-22 2019-06-11 中国石油化工股份有限公司 石油树脂连续加氢制备氢化石油树脂的方法
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Also Published As

Publication number Publication date
CA1316947C (fr) 1993-04-27
FR2629094A1 (fr) 1989-09-29
US5059732A (en) 1991-10-22
DE68903239D1 (de) 1992-11-26
JPH01284586A (ja) 1989-11-15
ATE81666T1 (de) 1992-11-15
FR2629094B1 (fr) 1991-01-04
DE68903239T2 (de) 1993-04-15
EP0334742A1 (de) 1989-09-27
JP2736799B2 (ja) 1998-04-02

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