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EP0621334A1 - Verfahren zur Herstellung von Brennstoff-durch Extraktion und Wasserstoffbehandlung von Kohlenwasserstoff Einsätz und so hergestellte Gasöl - Google Patents

Verfahren zur Herstellung von Brennstoff-durch Extraktion und Wasserstoffbehandlung von Kohlenwasserstoff Einsätz und so hergestellte Gasöl Download PDF

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Publication number
EP0621334A1
EP0621334A1 EP94400861A EP94400861A EP0621334A1 EP 0621334 A1 EP0621334 A1 EP 0621334A1 EP 94400861 A EP94400861 A EP 94400861A EP 94400861 A EP94400861 A EP 94400861A EP 0621334 A1 EP0621334 A1 EP 0621334A1
Authority
EP
European Patent Office
Prior art keywords
product
weight
solvent
less
hydrotreatment
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
EP94400861A
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English (en)
French (fr)
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EP0621334B1 (de
Inventor
Frédéric Morel
Marc Boulet
Massimo Zuliani
Jean Claude Company
Paul Mikitenko
Roben Loutaty
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
TotalEnergies Marketing Services SA
Original Assignee
IFP Energies Nouvelles IFPEN
Total Raffinage Distribution SA
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Publication of EP0621334A1 publication Critical patent/EP0621334A1/de
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Publication of EP0621334B1 publication Critical patent/EP0621334B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/08—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for compression ignition
    • 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
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • 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
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen

Definitions

  • the invention relates to a petroleum product and a process for obtaining said petroleum product which can optionally be used for the formulation of a fuel for an internal combustion engine and the product obtained by the process.
  • the gas oils that are currently found on the market either in the form of fuels for internal combustion compression-ignition engines (diesel type), or in the form of fuel, are most often refined products which contain sulfur. in an amount (expressed by weight of sulfur) of about 0.3%.
  • hydrodesulfurization treatment from a feed which can come from the direct distillation of a crude oil or from a specific treatment of a crude oil (for example a pyrolysis or a distillation followed by pyrolysis of the fraction recovered during distillation, or thermal or catalytic cracking) generally containing at least 0.8% by weight of sulfur.
  • sulfur content standards are in place or will be implemented in the very near future. These standards are becoming more and more stringent, particularly for diesel oils intended to be used as fuel for engines. Thus in France, in particular from 1995, the sulfur content of these gas oils must be at most equal to 0.05% by weight (500 ppm) while the gas oils conforming to the standards in force have a content of sulfur up to 0.3%.
  • the gas oils used in France as fuel for internal combustion engines must currently have a cetane number at least equal to 48 and the gas oils used as fuel, a cetane number at least equal to 40. We can expect in the near future to more stringent standards and in particular that concerning diesel fuel used as fuel in engines.
  • the present invention therefore relates to a simple implementation process, consuming little hydrogen and being able to use installations already present in the refinery, in particular the existing industrial hydrodesulfurization units, which limits the investment necessary for its implementation. . It makes it possible to improve the qualities of the diesel fuel produced and to comply with future standards and in particular that concerning the sulfur content.
  • the process of the invention also makes it possible, as will be shown in the embodiment described below, to improve the cetane engine index of diesel, to reduce its content of aromatic compounds not containing a heteroatom of sulfur in their molecule, to reduce its content of nitrogenous compounds to improve its color and its odor and finally to decrease the formation of solid particles during its use in an internal combustion engine.
  • hydrodesulfurization (HDS) will be used in the following description instead of hydrotreatment.
  • polyaromatic compounds compounds having at least two aromatic rings, sulfur or not.
  • the initial and final boiling point temperatures are TBP cut points.
  • At least 50% by volume of the product (Q2) is introduced and preferably at least 90%, or even all of this product, into the hydrodesulfurization reactor.
  • it is introduced into said reactor , the entire top product T1 from the distillation.
  • the hydrocarbon feedstock which is treated according to the process of the invention is most often called a diesel cutter and it preferably has an initial boiling point of approximately 150 ° C. and a final boiling point of approximately 400 ° C, its sulfur content is usually more than 0.1% and most often more than 0.5% by weight, its aromatic content at least partly in the form of polyaromatic compounds is usually about 15% to about 70% by weight and its content of n- and iso-alkanes is from 30 to 45% by weight.
  • This charge is most often a direct distillation diesel or a pyrolysis diesel.
  • the color of this filler measured according to the ASTM D 1500 method is usually greater than or equal to 2.
  • the cetane number according to ISO 5165, this filler is most often less than around 60 and it is for example around 50 to about 55.
  • the nitrogen content of this feed is usually about 20 to about 3000 ppm expressed by weight of nitrogen relative to the weight of the feed.
  • the product (P) obtained by the process of the present invention usually has a nitrogen content expressed by weight of nitrogen, usually 2 times less than that of the initial charge and often 4 to 5 times less.
  • This product (P) most often has a color measured according to the Saybolt standard of approximately 10 to 30, most often 15 to 25 and the cetane number of this product is generally at least 2 points higher and often at least 5 points above the index of cetane from the initial charge (for example from 2 to 10 points).
  • the content of aromatic compounds containing no sulfur atom in their molecule in this product (P) is usually reduced by at least 10% by weight relative to that of the initial charge and often by at least 30% by weight. weight.
  • the sulfur content relative to that of the initial charge is less than or equal to 5% by weight.
  • the content of n-and iso-alkanes generally increases from 4 to 15 points and most often from 6 to 11 points compared to that of the initial charge.
  • the invention advantageously relates to a petroleum product, usable in particular as a base used in the composition of a fuel, characterized in that the distillation cut corresponds to 95% by weight distilled between 320 ° C and 460 ° C, its cetane number is greater than 60, its content of n- and iso-alkanes is at least equal to 48% by weight, and its sulfur content less than or equal to 500 ppm (weight).
  • It also has a solvent content generally less than 10 ppm by weight, advantageously less than 5 ppm and most often less than 1 ppm.
  • the distillation is carried out under conditions making it possible to obtain a top product (T1) containing only a small proportion of compounds with at least one sulfur atom in their molecule very easily hydrotreated.
  • the top product is usually a fraction whose final boiling point is less than 360 ° C, preferably less than 330 ° C and for example about 310 ° C.
  • the bottoms product (Q1) is usually a fraction with an initial boiling point higher than around 300 ° C, often higher than 330 ° C and sometimes higher than 360 ° C, which eliminates the refractory sulfur compounds raffinate which would require subsequent hydrotreatment at higher pressure and therefore at much higher cost.
  • an amount of residue representing, for example, at most 30% of the initial charge is sent to the extraction unit, which makes it possible to use the existing extraction units which are generally of low capacity and optimize the capacity of these units.
  • the liquid / liquid extraction step is a step carried out under conventional conditions.
  • This extraction can for example be carried out against the current in a conventional device for example a filling column, trays or mechanically agitated (RDC: rotating disc contactor) generally having from 1 to 20 theoretical stages and preferably from 5 to 10 stages at a temperature generally between 0 ° C and 140 ° C, advantageously between 30 ° C and 80 ° C and under a pressure allowing to operate in the liquid phase and therefore between 0.1 and 1 MPa, preferably between 0.1 and 0.3 MPa.
  • the volume ratio of the solvent (S1) to the volume of the bottoms product (Q1) is generally from 0.2: 1 to 5: 1, preferably from approximately 0.5: 1 to approximately 2: 1 and more often about 1: 1.
  • the solvent is preferably chosen from the group of solvents making it possible to extract at least part of the aromatic compounds, not containing a sulfur atom in their molecule, present in the product (Q1) obtained in step a).
  • the extraction conditions are preferably chosen so as to obtain a raffinate (R1) containing by weight at most 90% and preferably at most 70% by weight of the total weight of the aromatic compounds, not containing a sulfur atom in their molecule, present in the product (Q1) obtained in step a).
  • the extract (E1) under these conditions will contain at least 10% and often at least 30% by weight of the total weight of the aromatic compounds, not containing a sulfur atom in their molecule, present in the product (Q1) obtained at step a).
  • the extraction solvent is most often a single solvent, but mixtures of solvent can also be used.
  • This solvent generally contains less than 20% and often less than 10% by weight of water.
  • This solvent can be an anhydrous solvent. It is most often chosen from the group formed by methanol, acetonitrile, monomethylformamide, dimethylformamide, dimethylacetamide, furfural, N-methylpyrolidone and dimethylsulfoxide. Dimethylformamide, N-methylpyrolidone or furfural are very often used.
  • At least one cosolvent which may be, an alcohol of 1 to 6 carbon atoms, for example a linear or branched alcohol, or furfuryl alcohol.
  • the feed to be treated has a high final boiling point and is particularly rich in nitrogen compounds, especially basic, it may be advantageous to introduce with the extraction solvent alone or in mixture, a minor amount of acids, in particular carboxylic (less than 1% by weight relative to the solvent for example).
  • carboxylic acids of 1 to 6 carbon atoms and more particularly, acids having a boiling point below 250 ° C., in particular formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, maleic acid, crotonic acid, isobutyric acid, valeric acid, trimethylacetic acid, benzoic acid, and 2-furoic acid .
  • the raffinate (R1) obtained in step b) is then sent to a distillation zone for example, in which it is distilled under conditions making it possible to recover an overhead fraction enriched, and preferably highly enriched, in solvent (S1 ) and a product (Q2) preferably highly depleted in solvent (S1).
  • a distillation zone for example, in which it is distilled under conditions making it possible to recover an overhead fraction enriched, and preferably highly enriched, in solvent (S1 ) and a product (Q2) preferably highly depleted in solvent (S1).
  • the conditions of this distillation are chosen so as to obtain a top fraction containing almost all of the solvent, that is to say for example more than 95% by weight of the amount of solvent contained in the raffinate (R1 ) and introduced into this distillation zone. At least about 99% by weight of the amount of solvent contained in the raffinate (R1) is thus preferably recovered.
  • the raffinate can be sent to at least one separation flask where a liquid-vapor equilibrium (flash) is achieved and a product (S1) enriched in solvent and a product (Q2) depleted in solvent.
  • This or these flasks can be followed by stripping, for example with steam or nitrogen to recover the last traces of solvent.
  • the parameters of the hydrodesulfurization step generally chosen most often correspond to those of a hydrodesulfurization carried out under mild conditions.
  • the space speed can be high, for example greater than 2h ⁇ 1.
  • the catalyst is one of those, for example, sold by the company PROCATALYSE.
  • the extract (E1) obtained in step b) is then sent to a separation zone, for example a distillation in which it is distilled under conditions making it possible to recover an enriched fraction. , and preferably highly enriched, in solvent (S1) and a product (Q3) depleted in solvent (S1).
  • a separation zone for example a distillation in which it is distilled under conditions making it possible to recover an enriched fraction. , and preferably highly enriched, in solvent (S1) and a product (Q3) depleted in solvent (S1).
  • the conditions of this separation are chosen so as to obtain a product containing almost all of the solvent, that is to say for example more than 95% by weight of the amount of solvent contained in the extract (E1) and introduced into this separation zone. At least about 99% by weight of the amount of solvent contained in the extract (E1) is thus preferably recovered.
  • the product (Q3) is sent to a hydrodesulfurization zone in which it is subjected to hydrodesulfurization, for example in the presence of a catalyst marketed by the company PROCATALYSE under conditions generally more severe, making it possible to obtain a product (P ′) having a sulfur content less than or equal to 0.3% by weight and preferably less than or equal to 0.2% by weight, or even less than or equal to 0.1% by weight.
  • This product (P ') will of course not be usable as fuel for the engines, since most often containing a quantity of sulfur greater than the future standard, on the other hand it will probably be able to be used as fuel.
  • At least part of the product (Q2) can be recovered at the end of step c) by lines (7) and (13) and be used as such as fuel or be mixed with the product (P ') resulting from the hydrodesulfurization of the product (Q3) or even be sent as a mixture with at least part of the product (Q3) to a hydrodesulfurization zone. There is then obtained, according to this embodiment, an amount of product at least partially desulphurized, usable as fuel.
  • the product or products, obtained by separation of the raffinate (R1) and optionally of the extract (E1), enriched (s) with solvent, are recycled in step b) liquid / liquid extraction.
  • the method of the present invention has increased flexibility over the methods described in the prior art. It also has the following main advantages: a higher content of n- and iso-alkanes is obtained in the raffinate (table) than according to the hydrocracking or hydrodesaromatization processes, a higher cetane number, in despite an aromatic hydrocarbon content greater than 10%.
  • the consumption of hydrogen in hydrotreatment is lower. It can be reduced for example to 0.15% by weight with respect to the charge, when the hydrogenation is limited to the maximum.
  • the feed used in this example is a direct-distillation gas oil having a cetane number of 55, a total content of aromatic compounds, sulfur and non-sulfur, of 34% by weight, a content of n- and iso alkanes of 18% by weight and 22% by weight, a sulfur content of 1.22% by weight, a nitrogen content expressed by weight of nitrogen of 255 ppm and a color measured according to standard ASTM D 1500 equal to 2.
  • This diesel has an initial distillation point of 150 ° C and a final distillation point of 400 ° C.
  • This charge is introduced via line 1 into a distillation zone from which a head fraction (T1) with a final boiling point below 320 ° C. is recovered via line 2 which contains 0.88% by weight of sulfur, and via line 3 a bottom fraction (Q1) with a final boiling point greater than 320 ° C. containing 1.7% by weight of sulfur.
  • the top product (T1) is sent via line 2 and line 8 to a hydrodesulfurization (HDS) zone.
  • HDS hydrodesulfurization
  • the bottoms product (Q1) leaving the distillation zone D1 is sent via line 3 to the extraction zone (LE) into which is introduced via line 4 an amount of dimethylformamide equal in volume to the amount of product of tail (Q1) introduced into this area.
  • This zone is an extraction column comprising a packing formed by Pall rings corresponding to three theoretical stages. The extraction is carried out against the current, at atmospheric pressure and at a temperature of 70 ° C.
  • a raffinate is obtained (R1) which is sent via line 5 to the distillation zone D2 in which the dimethylformamide is separated at the head which is recovered by line 10 a for possible recycling to the extraction zone and at the tail a raffinate (Q2) containing practically no more dimethylformamide, having a sulfur content of 0.51% which is sent via line 7 and line 8 to the hydrodesulfurization zone (HDS).
  • R1 which is sent via line 5 to the distillation zone D2 in which the dimethylformamide is separated at the head which is recovered by line 10 a for possible recycling to the extraction zone and at the tail a raffinate (Q2) containing practically no more dimethylformamide, having a sulfur content of 0.51% which is sent via line 7 and line 8 to the hydrodesulfurization zone (HDS).
  • the products (T1) and (Q2) introduced into the hydrodesulfurization zone are subjected to a hydrodesulfurization treatment under a partial hydrogen pressure of 2.5 MPa in the presence of an industrial catalyst containing cobalt and molybdenum on an alumina support sold by the company PROCATALYSE under the reference HR 306C, the temperature is maintained at 330 ° C, the hydrogen recycling is equal to 200 liters per liter of charge and the hourly space speed is 2.5 h ⁇ 1.
  • such a high-performance hydrodesulfurization carried out directly on the same diesel fuel must be carried out at an hourly space speed of 1.5 h ⁇ 1, all the other conditions remaining substantially equal elsewhere.
  • This product has a color measured according to the Saybolt method equal to 20 and a nitrogen content of 50 ppm by weight.
  • the cetane number of the product (P) is 62.
  • This product is incorporated into the Diesel pool.
  • the content of n- and iso-alkanes is 21% by weight and 31% by weight.
  • An extract (E1) is also recovered via line 6 which is sent to a distillation zone D3 in which the dimethylformamide is separated at the head which is recovered by line 10 b for possible recycling to the zone of extraction and at the tail an extract (Q3) containing practically no more dimethylformamide, having a sulfur content of 5.1% which is sent via line 11 to a hydrodesulfurization zone (HDS) distinct from that into which one has introduced the raffinate (Q2) and the top product (T1).
  • This hydrodesulfurization is carried out in the presence of the HR 306C catalyst, under a partial hydrogen pressure of 4 MPa, at a temperature of 350 ° C. with a hydrogen recycling of 300 liters per liter of charge and an hourly space velocity of 1, 2 hrs.
  • a product (P ') containing 0.2% by weight of sulfur, 75% by weight of aromatic compounds is recovered via line 12.
  • This product has a color measured according to the ASTM D-1500 method equal to 1 and a nitrogen content of 200 ppm by weight. It can be sent to the domestic fuel pool.

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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)
  • Catalysts (AREA)
EP94400861A 1993-04-23 1994-04-20 Verfahren zur Herstellung von Brennstoff-durch Extraktion und Wasserstoffbehandlung von Kohlenwasserstoffeinsatz und so hergestellte Gasöl Expired - Lifetime EP0621334B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9304924A FR2704232B1 (fr) 1993-04-23 1993-04-23 Procede d'amelioration des qualites d'une charge hydrocarbonee par extraction et hydrodesulfuration et le gazole obtenu.
FR9304924 1993-04-23

Publications (2)

Publication Number Publication Date
EP0621334A1 true EP0621334A1 (de) 1994-10-26
EP0621334B1 EP0621334B1 (de) 1998-11-11

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EP94400861A Expired - Lifetime EP0621334B1 (de) 1993-04-23 1994-04-20 Verfahren zur Herstellung von Brennstoff-durch Extraktion und Wasserstoffbehandlung von Kohlenwasserstoffeinsatz und so hergestellte Gasöl

Country Status (9)

Country Link
US (2) US5527448A (de)
EP (1) EP0621334B1 (de)
JP (1) JP3564578B2 (de)
KR (1) KR100313265B1 (de)
AT (1) ATE173292T1 (de)
DE (1) DE69414448T2 (de)
DK (1) DK0621334T3 (de)
ES (1) ES2126721T3 (de)
FR (1) FR2704232B1 (de)

Cited By (4)

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EP0661371B1 (de) * 1993-12-28 2003-08-20 Institut Francais Du Petrole Verfahren zur Erzeugung eines Brennstoffes für innere Verbrennungsmotoren durch Wasserstoffbehandlung und Extraktion
WO2005003261A1 (fr) * 2003-07-04 2005-01-13 Beijing Grand Golden-Bright Engineering & Technologies Co., Ltd. Procede de recombinaison d'hydrocarbures catalytiques
WO2013019527A1 (en) * 2011-07-29 2013-02-07 Saudi Arabian Oil Company Selective middle distillate hydrotreating process
EP2725086A1 (de) * 2011-06-22 2014-04-30 Obshchestvo S Ogranichennoy Otvestvennostyu "Lukoyl-Nizhegorodskiy Nauchno-Issledovatelskiy I Proyektnyy Institut po Pererabotke Nefti Verfahren zur herstellung eines dieselkraftstoffs

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FR2704232B1 (fr) * 1993-04-23 1995-06-16 Inst Francais Du Petrole Procede d'amelioration des qualites d'une charge hydrocarbonee par extraction et hydrodesulfuration et le gazole obtenu.
US6039771A (en) * 1998-04-23 2000-03-21 Krc-Gp, Inc. Formulation and method of preparation of energy fortified diesel fuel
US5917101A (en) * 1998-10-07 1999-06-29 Western Petroleum Enterprises, Inc. Heating oil composition
JP2000144150A (ja) * 1998-11-11 2000-05-26 Nippon Mitsubishi Oil Corp 低硫黄軽油
US6475376B2 (en) * 1999-06-11 2002-11-05 Chevron U.S.A. Inc. Mild hydrotreating/extraction process for low sulfur fuel for use in fuel cells
FR2843403B1 (fr) * 2002-08-08 2007-08-24 Totalfinaelf France Procede et dispositif de purification d'une coupe petroliere
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ES2126721T3 (es) 1999-04-01
JP3564578B2 (ja) 2004-09-15
US5527448A (en) 1996-06-18
US5718820A (en) 1998-02-17
FR2704232A1 (fr) 1994-10-28
DK0621334T3 (da) 1999-07-26
FR2704232B1 (fr) 1995-06-16
ATE173292T1 (de) 1998-11-15
DE69414448T2 (de) 1999-06-02
DE69414448D1 (de) 1998-12-17
EP0621334B1 (de) 1998-11-11
KR100313265B1 (ko) 2001-12-28

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