EP1445299B1 - Verfahren zur Gewinnung einer Beschickung zu einem Veretherungsverfahren - Google Patents

Verfahren zur Gewinnung einer Beschickung zu einem Veretherungsverfahren Download PDF

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Publication number
EP1445299B1
EP1445299B1 EP04290069A EP04290069A EP1445299B1 EP 1445299 B1 EP1445299 B1 EP 1445299B1 EP 04290069 A EP04290069 A EP 04290069A EP 04290069 A EP04290069 A EP 04290069A EP 1445299 B1 EP1445299 B1 EP 1445299B1
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EP
European Patent Office
Prior art keywords
process according
nitrogen
compounds
metal
containing compounds
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.)
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Application number
EP04290069A
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English (en)
French (fr)
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EP1445299A1 (de
Inventor
Florent Picard
Alain Forestiere
Julia Magne-Drisch
Nathalie Marchal-George
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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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
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/301—Boiling range
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4018—Spatial velocity, e.g. LHSV, WHSV
    • 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 present invention relates to a process for obtaining a hydrocarbon fraction that can be used as a feedstock of an etherification unit and that contains a reduced quantity of diene, nitrogen and sulfur compounds, from an initial charge of hydrocarbons.
  • the present invention finds application in the treatment of gasolines with a view to obtaining a fraction comprising olefins containing from 4 to 6 carbon atoms, and having a reduced content of diene, nitrile, nitrogen and sulfur compounds.
  • this fraction can then be used to supply etherification units, for example in order to produce methyl tertiary butyl ethers (MTBE), ethyl tertiary butyl ethers (ETBE), tertiary amyl methyl ether (TAME) or tertiary amyl ethyl ether ( TAEE)
  • the request for WO 96/00714 proposes a method for reducing the content of pollutants present in the charges for etherification units, by selective hydrogenation.
  • the pollutants eliminated by this process are nitriles and diolefins.
  • the diolefins are initially hydrogenated to olefins, and then the nitriles are hydrogenated to amines.
  • the catalyst used in this step is a catalyst comprising cobalt. Since amines are basic compounds, they are then easily extracted by washing with water. This method therefore also requires the implementation of a washing step to remove the nitrogen compounds in the form of amines and thus has the aforementioned drawback of the reprocessing of the washing solutions.
  • the US Patent 6,469,223 describes a process for the selective hydrogenation of dienes in a hydrocarbon feedstock.
  • the present invention provides a cost-effective and simple way of eliminating, at least partially, the dienes, the nitrile-type nitrogen compounds and the light sulfur compounds present in the initial gasoline.
  • the method used according to the invention comprises at least two stages: a first stage of selective hydrogenation of the whole of the initial hydrocarbon feedstock and a second stage of fractionation of said hydrogenated feedstock.
  • This step is intended to at least partially remove the diolefins present in the initial hydrocarbon feed, such as preferably a gasoline cut.
  • Diolefins are precursors of gums which polymerize in the etherification reactors and limit their life as well as nitrile-type nitrogen compounds (whose formula is given below). It has indeed been found by the applicant that under the experimental conditions mentioned in the rest of the description, said nitriles are converted into heavy nitrogen compounds which respond positively to the measurement of basic nitrogen.
  • Nitrite compounds R - C ⁇ N, where R comprises from 1 to 6 carbon atoms.
  • This step also makes it possible to convert light sulfur compounds such as mercaptans, sulphides and CS2, whose boiling point is generally lower than that of thiophene, into heavier sulfur compounds whose boiling point is higher than that of thiophene.
  • Said selective hydrogenation step generally takes place in the presence of a catalyst comprising at least one metal of group VIII of the periodic table, preferably chosen from the group formed by platinum, palladium and nickel, and a support.
  • the cobalt may also be chosen from said group.
  • a catalyst containing 1 to 20% by weight of nickel deposited on an inert support such as, for example, alumina, silica, silica-alumina, a nickel aluminate or a support containing at least 50% alumina.
  • Another Group VIB metal of the Periodic Table can be combined with this group VIII metal to form a bimetallic catalyst, such as, for example, molybdenum or tungsten. This group VIB metal is preferably deposited at a level of 1% by weight at 20% by weight on the support.
  • the choice of operating conditions is particularly important according to the invention.
  • the operation will generally be carried out under pressure in the presence of a quantity of hydrogen in small excess relative to the stoichiometric value necessary for hydrogenating the diolefins.
  • hydrogen and the feedstock to be treated are injected in ascending or descending streams into a preferably fixed catalyst bed reactor.
  • the temperature is most generally between 50 and 300 ° C, and preferably between 80 and 250 ° C, and very preferably between 120 and 210 ° C.
  • the pressure is chosen to be sufficient to maintain more than 80%, and preferably more than 95% by weight of the gasoline to be treated in liquid form in the reactor; it is most generally between 0.4 and 5 MPa inclusive, and preferably greater than 1 MPa.
  • An advantageous pressure is between 1 to 4 MPa inclusive.
  • the space velocity is, in these conditions of the order of 1 to 12 h -1 , preferably of the order of 2 to 10 h -1 .
  • the initial hydrocarbon feedstock such as a petrol cut may contain up to a few% by weight of diolefins. After hydrogenation, the diolefin content is most often reduced to less than 5000 ppm, preferably less than 2500 ppm, or even less than 1500 ppm.
  • step a) takes place in a catalytic hydrogenation reactor which comprises a catalytic reaction zone traversed by the entire charge and the amount of hydrogen necessary to effect the desired reactions.
  • the nitrogen compounds derived from step a) are compounds with a boiling point greater than those of hydrocarbons comprising 5 carbon atoms.
  • these compounds react with the measurement of basic nitrogen according to the ASTM4739 method.
  • Step b) consists of a separation of the nitrogen compounds by distillation.
  • the effluents resulting from stage a) are fractionated in order to produce at least two sections, a light fraction comprising the majority of the hydrocarbons, and mainly olefins containing 4 or 5 carbon atoms and free of nitrogen compounds, and a heavy fraction concentrating heavy hydrocarbons and nitrogen compounds weighed up during step a).
  • this preferred embodiment also makes it possible to at least partially eliminate the sulfur compounds of said light fraction.
  • the nitrogen compound content of the light fraction of the gasoline from step b) generally contains less than 20 ppm nitrogen, preferably less than 10 ppm nitrogen, and very preferably less than 5 ppm nitrogen.
  • the content of light sulfur compounds in the light fraction of gasoline is generally less than 200 ppm, preferably less than 100 ppm, and very preferably less than 50 ppm sulfur.
  • Table 1 summarizes the characteristics of gasoline A as well as the 3 fractions obtained by distillation. ⁇ u> Table 1 ⁇ / u> Essence A PI-55 55-140 140+ Density 0.716 .6504 .7382 0.842 Basic nitrogen (ppm) 9 1 1 71 Total nitrogen (ppm) 21 15 13 110 MAV (mg / g) 14 6.5 15.5 30 HBr 101 130 79 48 S (ppm) 780 92 926 2563 Yield (% wt) 100 29.59 64.27 6.14
  • the light gasoline corresponding to the PI-55 cut concentrates the majority of the light olefins (C4 and C5). It therefore constitutes the etherification charge. This fraction comprises 15 ppm of nitrogen, 92 ppm of sulfur and a MAV (maleic acid value) of 6.5, which corresponds to almost 0.8% by weight of diolefins. This gasoline treated on an acidic etherification catalyst would cause a premature deactivation thereof.
  • Example below is in accordance with the present invention.
  • the initial charge used is similar to that of Example 1.
  • gasoline produced (gasoline B) is distilled in three sections (step b)).
  • Step a) is carried out as follows: gasoline A is treated on a fixed bed reactor charged with HR845® catalyst based on nickel and molybdenum marketed by Axens, in the presence of hydrogen. The reaction is carried out at 165 ° C. under a pressure of 20 bar (2 MPa) and a space velocity of 4 h -1 . The H 2 / charge ratio expressed in liter of hydrogen per liter of feedstock is 6. The gasoline thus produced during step a) is gasoline B, the characteristics of which are given in Table 2.
  • Gasoline B is then fractionated by distillation into 3 fractions whose cutting points are identical to the fractions of Example 1.

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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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (8)

  1. Verfahren zur Gewinnung einer Kohlenwasserstofffraktion, die als Charge einer Veretherungsanlage verwendet werden kann und eine verringerte Menge an dienischen, stickstoffhaltigen und schwefelhaltigen Verbindungen enthält, ausgehend von einer Ursprungscharge an Kohlenwasserstoffen, die eine Mischung aus Olefinen, Dienen, Nitrilen sowie schwefelhaltigen Verbindungen umfasst, wobei das Verfahren mindestens die folgenden, nacheinander durchgeführten Schritte umfasst:
    a) eine selektive Hydrierung der Ursprungscharge an Kohlenwasserstoffen, in Gegenwart eines Katalysators, der mindestens ein Metall der Gruppe VIII und ein weiteres Metall der Gruppe VIB des Periodensystems umfasst,
    b) eine Fraktionierung durch Destillation der Stoffströme, die in Schritt a) entstehen, unter Bedingungen, die es ermöglichen, mindestens zwei Fraktionen zu erhalten, darunter
    - die Kohlenwasserstofffraktion, welche einen Siedepunkt von weniger als 60 °C aufweist und eine verringerte Menge an dienischen, stickstoffhaltigen und schwefelhaltigen Verbindungen umfasst, und
    - eine Schwerfraktion, welche die schwerflüchtigen Kohlenwasserstoffe und den überwiegenden Anteil der stickstoffhaltigen und schwefelhaltigen Verbindungen, die in Schritt a) entstehen, enthält.
  2. Verfahren nach Anspruch 1, wobei das Metall der Gruppe VIII aus der Gruppe ausgewählt ist, die aus Platin, Palladium, Nickel besteht.
  3. Verfahren nach Anspruch 2, wobei der Katalysator 1 Gew.-% bis 20 Gew.-% an Nickel enthält, welches auf einen inerten Träger aufgebracht ist.
  4. Verfahren nach Anspruch 1, wobei es sich bei dem Metall der Gruppe VIII um Kobalt handelt.
  5. Verfahren nach einem der vorhergehenden Ansprüche, wobei der Katalysator 1 Gew.-% bis 20 Gew.-% an Metall der Gruppe VIB umfasst.
  6. Verfahren nach einem der vorhergehenden Ansprüche, wobei es sich bei dem Metall der VIB um Molybdän oder Wolfram handelt.
  7. Verfahren nach einem der vorhergehenden Ansprüche, wobei der Katalysator unter einem Druck von 0,4 bis 5 MPa, bei einer Temperatur von 50 bis 300 °C eingesetzt wird, mit einer stundenbezogenen Raumgeschwindigkeit der Charge von 1 h-1 bis 12 h-1.
  8. Verfahren nach einem der vorhergehenden Ansprüche, wobei die Hydrierung in Gegenwart einer Wasserstoffmenge durchgeführt wird, die einen geringfügigen Überschuss darstellt, unter Bezugnahme auf den stöchiometrischen Wert, welcher erforderlich ist, um die Gesamtheit der Diene, die in der Ursprungscharge an Kohlenwasserstoffen enthalten sind, zu hydrieren.
EP04290069A 2003-01-22 2004-01-09 Verfahren zur Gewinnung einer Beschickung zu einem Veretherungsverfahren Expired - Lifetime EP1445299B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0300693A FR2850113B1 (fr) 2003-01-22 2003-01-22 Procede d'obtention d'une charge utilisable dans une unite d'etherification
FR0300693 2003-01-22

Publications (2)

Publication Number Publication Date
EP1445299A1 EP1445299A1 (de) 2004-08-11
EP1445299B1 true EP1445299B1 (de) 2012-03-14

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EP04290069A Expired - Lifetime EP1445299B1 (de) 2003-01-22 2004-01-09 Verfahren zur Gewinnung einer Beschickung zu einem Veretherungsverfahren

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US (1) US7025872B2 (de)
EP (1) EP1445299B1 (de)
ES (1) ES2381785T3 (de)
FR (1) FR2850113B1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100389874C (zh) * 2006-07-14 2008-05-28 谷育英 一种用于c5石油树脂中烯烃加氢反应催化剂及其制备方法和应用
US7553995B2 (en) * 2007-09-11 2009-06-30 Catalytic Distillation Technologies Method of producing tertiary amyl ethyl ether
EP2816094B1 (de) 2013-06-19 2020-04-29 IFP Energies nouvelles Herstellungsverfahren einer essenz mit niedrigem schwefel- und mercaptangehalt

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4175033A (en) * 1976-05-06 1979-11-20 Uop Inc. Hydroprocessing of hydrocarbons over nickel, moly, platinum catalyst
US5321163A (en) * 1993-09-09 1994-06-14 Chemical Research & Licensing Company Multi-purpose catalytic distillation column and eterification process using same
WO1996017903A1 (en) * 1994-11-25 1996-06-13 Kvaerner Process Technology Ltd Multi-step hydrodesulfurization process
US5712415A (en) * 1994-12-13 1998-01-27 Intevep, S.A. Process for the simultaneous selective hydrogenation of diolefins and nitriles
US5948942A (en) * 1994-12-13 1999-09-07 Intevep, S.A. Bimetallic catalyst for the simultaneous selective hydrogenation of diolefins and nitriles and method of making same
US6210561B1 (en) * 1996-08-15 2001-04-03 Exxon Chemical Patents Inc. Steam cracking of hydrotreated and hydrogenated hydrocarbon feeds
US6042719A (en) * 1998-11-16 2000-03-28 Mobil Oil Corporation Deep desulfurization of FCC gasoline at low temperatures to maximize octane-barrel value
US6123830A (en) * 1998-12-30 2000-09-26 Exxon Research And Engineering Co. Integrated staged catalytic cracking and staged hydroprocessing process
US6469223B2 (en) * 2000-01-04 2002-10-22 Fina Technology, Inc. Selective hydrogenation of dienes
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
US20040178123A1 (en) * 2003-03-13 2004-09-16 Catalytic Distillation Technologies Process for the hydrodesulfurization of naphtha

Also Published As

Publication number Publication date
EP1445299A1 (de) 2004-08-11
ES2381785T3 (es) 2012-05-31
FR2850113A1 (fr) 2004-07-23
US20040167363A1 (en) 2004-08-26
FR2850113B1 (fr) 2007-03-02
US7025872B2 (en) 2006-04-11

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