EP1445299A1 - 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
EP1445299A1
EP1445299A1 EP04290069A EP04290069A EP1445299A1 EP 1445299 A1 EP1445299 A1 EP 1445299A1 EP 04290069 A EP04290069 A EP 04290069A EP 04290069 A EP04290069 A EP 04290069A EP 1445299 A1 EP1445299 A1 EP 1445299A1
Authority
EP
European Patent Office
Prior art keywords
nitrogen
compounds
fraction
hydrocarbons
metal
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.)
Granted
Application number
EP04290069A
Other languages
English (en)
French (fr)
Other versions
EP1445299B1 (de
Inventor
Florent Picard
Alain Forestiere
Julia Magne-Drisch
Nathalie Marchal-George
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.)
IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Publication of EP1445299A1 publication Critical patent/EP1445299A1/de
Application granted granted Critical
Publication of EP1445299B1 publication Critical patent/EP1445299B1/de
Anticipated expiration legal-status Critical
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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 usable hydrocarbon fraction as charge of an etherification unit and containing a reduced amount of compounds diene, nitrogen and sulfur, from an initial charge of hydrocarbons.
  • the present invention finds its application in the treatment of essences with a view to obtaining a fraction comprising olefins containing from 4 to 6 carbon atoms, and having a reduced content of diene compounds, nitriles, nitrogen and sulfur, this fraction can then be used to feed etherification units, by example to produce methyl tertio butyl ethers (MTBE), ethyl tertio butyl ethers (ETBE), tertio amyl methyl ether (TAME) or tertio amyl ethyl ether (TAEE)
  • MTBE methyl tertio butyl ethers
  • ETBE ethyl tertio butyl ethers
  • TAME tertio amyl methyl ether
  • TEE tertio amyl ethyl ether
  • the activity of the acid catalysts generally used in the units etherification can be greatly reduced due to the presence in the cut to be treated of unwanted compounds.
  • the diolefins (dienes) can be the source of deposition of polymer on the catalyst, and the nitriles cause a gradual deactivation of the catalyst.
  • certain compounds such as light sulfides and amines have a certain basicity and can also gradually degrade the activity of acid catalysts.
  • Patent application WO 96/00714 provides a method for reducing the content of pollutants present in the charges for etherification units, by selective hydrogenation.
  • the pollutants removed by this process are nitriles and diolefins.
  • the diolefins are in initially hydrogenated to olefins, then the nitriles are hydrogenated to amines.
  • the catalyst used in this step is a catalyst comprising cobalt. Amines being basic compounds, these are then easily extracted by washing with water. This process therefore also requires the implementation of a washing step in order to remove the compounds nitrogen in the form of amines and therefore has the aforementioned drawback of the reprocessing of washing solutions.
  • the present invention provides an economical and simple to implement means for remove, at least partially, dienes, nitrile nitrogen compounds and light sulfur compounds present in the original gasoline.
  • the process implemented according to the invention comprises at least two stages: a first stage of selective hydrogenation of the entire initial hydrocarbon charge and a second stage of fractionation of said hydrogenated charge.
  • said hydrocarbon fraction has a higher cutting or boiling point which is less than 100 ° C, preferably less than 80 ° C and very preferably less than 60 ° C.
  • This step is intended to at least partially eliminate the diolefins present in the initial hydrocarbon charge, such as preferably a petrol cut.
  • Diolefins are gum precursors which polymerize in etherification reactors and limit their lifespan as well as nitrogenous nitrile compounds (the formula of which is given below). It was indeed found by the applicant that under the conditions mentioned in the rest of the description, said nitriles are transformed into heavy nitrogen compounds which respond positively to the measurement of basic nitrogen.
  • This step also makes it possible to transform light sulfur compounds such as mercaptans, sulphides and CS2, whose boiling point is generally lower to that of thiophene, into heavier sulfur compounds whose boiling point is higher than that of thiophene.
  • Said selective hydrogenation stage generally takes place in the presence of a catalyst comprising at least one metal from group VIII of the periodic table, preferably chosen from the group formed by platinum, palladium and nickel, and a support. Without leaving the within the framework of the invention, cobalt may also be chosen from said group.
  • a catalyst comprising 1 to 20% by weight of nickel deposited on an inert support, such that for example alumina, silica, silica-alumina, a nickel aluminate or a support containing at least 50% alumina.
  • Another metal from group VIB of the classification periodic can be associated 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 to 20% by weight on the support.
  • the choice of operating conditions is particularly important according to the invention. We will operate most generally under pressure in the presence of a small amount of hydrogen compared to the stoichiometric value necessary to hydrogenate the diolefins.
  • hydrogen and the charge to be treated are injected in updrafts or downdrafts in a reactor preferably with a fixed catalyst bed.
  • 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 as sufficient to maintain more than 80%, and preferably more 95% by weight of the gasoline to be treated in liquid form in the reactor; she is the most generally between 0.4 to 5 MPa, limits included, and preferably greater than 1 MPa.
  • Advantageous pressure is between 1 to 4 MPa, limits included.
  • the space speed 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 charge such as a petrol cut can contain up to a few% weight of diolefins.
  • 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 reactor catalytic hydrogenation which includes a catalytic reaction zone crossed by the total charge and the quantity of hydrogen necessary to carry out the desired reactions.
  • the nitrogen compounds originating from stage a) are boiling point compounds higher than those of hydrocarbons comprising 5 carbon atoms. In addition these compounds react to the basic nitrogen measurement according to the ASTM4739 method.
  • Step b) consists of a separation of the nitrogen compounds by distillation.
  • the effluents from from step a) are split to produce at least two cuts, including a slight fraction comprising the majority of hydrocarbons, and mainly olefins with 4 or 5 atoms of carbon and free of nitrogen compounds, and a heavy fraction concentrating the hydrocarbons heavy and the nitrogen compounds weighed down during step a).
  • this preferred embodiment further allows at least partial removal of the compounds sulfur of said light fraction.
  • the content of nitrogen compounds in the light fraction of gasoline from step b) contains generally less than 20 ppm of nitrogen, preferably less than 10 ppm of nitrogen, and very preferably less than 5 ppm of nitrogen.
  • the content of light sulfur compounds in the light fraction of petrol is generally less than 200 ppm, preferably less than 100 ppm, and very preferably 50 ppm lower sulfur.
  • the light essence corresponding to the PI-55 cut concentrates most of the olefins light (C4 and C5). It therefore constitutes the etherification charge. This fraction includes 15 ppm nitrogen, 92 ppm sulfur and an AVM (maleic acid value) of 6.5, which corresponds to nearly 0.8% by weight of diolefins. This gasoline treated on an acid etherification catalyst would result in premature deactivation of it.
  • Example below is in accordance with the present invention.
  • the initial charge used is similar to that of Example 1.
  • step a After a first selective hydrogenation treatment in a first step a), the gasoline produced (essence B) is distilled in three sections (step b)).
  • Step a) is carried out as follows: the gasoline A is treated on a fixed bed reactor loaded with HR845® catalyst based on nickel and molybdenum sold by the company Axens, in the presence of hydrogen. The reaction is carried out at 165 ° C, under a pressure of 20 bar (2MPa) and a space speed of 4 h -1 . The H 2 / charge ratio expressed in liters of hydrogen per liter of charge is 6. The gasoline thus produced during step a) is gasoline B, the characteristics of which are given in table 2.
  • Essence B is then fractionated by distillation into 3 fractions, the cutting points of which 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)
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 true EP1445299A1 (de) 2004-08-11
EP1445299B1 EP1445299B1 (de) 2012-03-14

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP04290069A Expired - Lifetime EP1445299B1 (de) 2003-01-22 2004-01-09 Verfahren zur Gewinnung einer Beschickung zu einem Veretherungsverfahren

Country Status (4)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2816094A1 (de) 2013-06-19 2014-12-24 IFP Energies nouvelles Herstellungsverfahren einer Essenz mit niedrigem Schwefel- und Mercaptangehalt

Families Citing this family (2)

* 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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5321163A (en) * 1993-09-09 1994-06-14 Chemical Research & Licensing Company Multi-purpose catalytic distillation column and eterification process using same
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
US6469223B2 (en) * 2000-01-04 2002-10-22 Fina Technology, Inc. Selective hydrogenation of dienes

Family Cites Families (8)

* 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
US5968347A (en) * 1994-11-25 1999-10-19 Kvaerner Process Technology Limited 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
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
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5321163A (en) * 1993-09-09 1994-06-14 Chemical Research & Licensing Company Multi-purpose catalytic distillation column and eterification process using same
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
US6469223B2 (en) * 2000-01-04 2002-10-22 Fina Technology, Inc. Selective hydrogenation of dienes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2816094A1 (de) 2013-06-19 2014-12-24 IFP Energies nouvelles Herstellungsverfahren einer Essenz mit niedrigem Schwefel- und Mercaptangehalt

Also Published As

Publication number Publication date
EP1445299B1 (de) 2012-03-14
FR2850113B1 (fr) 2007-03-02
ES2381785T3 (es) 2012-05-31
US7025872B2 (en) 2006-04-11
US20040167363A1 (en) 2004-08-26
FR2850113A1 (fr) 2004-07-23

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