EP1336648A1 - Verfahren zur Aufwertung von Aromaten und Naften-Aromaten enthaltenden Gasölschnitten. - Google Patents

Verfahren zur Aufwertung von Aromaten und Naften-Aromaten enthaltenden Gasölschnitten. Download PDF

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Publication number
EP1336648A1
EP1336648A1 EP03290339A EP03290339A EP1336648A1 EP 1336648 A1 EP1336648 A1 EP 1336648A1 EP 03290339 A EP03290339 A EP 03290339A EP 03290339 A EP03290339 A EP 03290339A EP 1336648 A1 EP1336648 A1 EP 1336648A1
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EP
European Patent Office
Prior art keywords
group
hydrorefining
catalyst
metal
temperature
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.)
Ceased
Application number
EP03290339A
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English (en)
French (fr)
Inventor
Eric Benazzi
Patrick Bourges
Christophe Gueret
Pierre Marion
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Publication of EP1336648A1 publication Critical patent/EP1336648A1/de
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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
    • C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
    • C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
    • C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps

Definitions

  • the present invention relates to the field of fuels for combustion engines internal. It relates more particularly to the conversion of a diesel cut and in particular the manufacture of a fuel for a compression ignition engine. She also relates to the fuel thus obtained.
  • diesel fractions whether they come from the direct distillation of a crude oil or whether they come from a conversion process such as cracking catalytic, still contain significant amounts of compounds aromatic, nitrogen and sulfur.
  • a fuel must have a cetane number greater than 51, a sulfur content less than 350 ppm (parts per million by mass), a density, d15 / 4, at 15 ° C less than 0.845 g / cm 3 , a content of polyaromatic compounds of less than 11% by weight and a boiling point of 95% of its components, T95, of less than 360 ° C.
  • the diesel cuts generally come either from direct distillation of crude or from catalytic cracking: i.e. cuts of light distillates (Anglo-Saxon initials LCO for Light Cycle Oil), heavy fraction cuts (HCO initials) for Heavy Cycle Oil), or another conversion process (coking, visbreaking, hydroconversion of residue etc.) or even diesel fuels from the distillation of crude oil aromatic or naphthenoaromatic of the Cerro-Negro, Zuata, El Pao type. It is particularly important to produce an effluent that can be directly and fully valued as a very high quality fuel cutter.
  • Patent FR 2 777 290 proposes a process combining hydrocracking with a hydrogenation in order to decrease the sulfur content and increase the cetane of the fuels thus produced. This process, which already has good performance, must however be improved in order to meet the increasingly stringent requirements that will be required in most countries industrialized.
  • An improved process has been found combining hydrocracking with hydrogenation making it possible to produce fuels meeting even more stringent specifications, not only with a maximum sulfur content of 350 ppm, preferably 50 ppm, and a minimum cetane number.
  • 51 preferably 53, in particular 58, but also a maximum temperature T95 of 360 ° C, preferably 340 ° C, a maximum content of polyaromatic compounds of 11% by weight, preferably 6% by weight , in particular 1% by weight and a maximum density d15 / 4 of 0.845 g / cm 3 , preferably 0.825 g / cm 3 .
  • the fuels obtained by this improved process thus have a high cetane number, a reduced sulfur content meeting current and future specifications. They also have a boiling temperature T95, a density d15 / 4 and contents of polyaromatic compounds sufficiently reduced to make it possible to meet not only the current specifications, and preferably the forecasts of the future European specifications of 2005.
  • the main object of the present invention is therefore to provide a conversion process a diesel cut, in particular a diesel cut with a high content of compounds aromatic or naphthenoaromatic, allowing to improve its cetane index and decrease its sulfur, aromatic and polyaromatic content while decreasing its temperature T95 (ASTM D86) and its density d15 / 4, and this so as to meet the most stringent future specifications that will be applied to cuts gas oils.
  • the operating conditions of the process of the invention have surprisingly led fuels with not only a reduced sulfur content and an index of higher cetane, but also at a temperature, T95, of 95% boiling components, with aromatic content and density, d15 / 4, at 15 ° C having lower values.
  • the diesel fillers to be treated are generally light diesel, for example direct distillation gas oils, fluid catalytic cracking gas oils (initials Anglo-Saxon FCC for Fluid Catalytic Cracking) or (LCO). They present generally an initial boiling point of at least 180 ° C and a final boiling point of at most 370 ° C.
  • the weight composition of these charges by family of hydrocarbons is variable depending on the intervals. According to the compositions usually encountered, the paraffin contents are between 5.0 and 30.0% by weight and naphthenes between 5.0 and 60% by weight.
  • the diesel fillers preferably have a content of aromatic compounds (including polyaromatic and naphthenoaromatic compounds) between 20% and 90%, in especially between 40 and 80% by weight.
  • the process according to the invention makes it possible, during the first hydrorefining step, to reduce sulfur content, nitrogen content, aromatic content and polyaromatics, as well as increasing the cetane number.
  • the conversion to products having a boiling point below 150 ° C is limited to the hydrorefining stage. So converting into products having a boiling point below 150 ° C is, for the hydrorefining step, included between 1 and 15%, preferably 5 and 15% by weight.
  • the operating conditions to apply to respect these conversion rates favor the reduction of the content of compounds aromatics by hydrogenating them and increases the cetane number.
  • the subsequent step of the process is carried out at a temperature lower than that of the hydrorefining stage. He was found with surprise that this made it possible to complete the hydrogenation of aromatic compounds and polyaromatics while still allowing moderate cracking of the load, since said cracking is carried out at relatively low temperatures. So, the difference between the temperature TR1 of the hydrorefining stage and the temperature TR2 of the subsequent step is between 0 and 80 ° C. This difference is preferably between 5 ° C and 70 ° C, especially between 10 ° C and 60 ° C, in particular between 15 ° C and 50 ° C. Alternatively, this difference can be between 11 ° C and 70 ° C, preferably between 13 ° C and 60 ° C, in particular between 15 ° C and 50 ° C.
  • the method of the invention thus makes it possible to increase, during the subsequent step, the number of cetane while decreasing the density, d15 / 4, and the temperature, T95, of the diesel cut.
  • the fuel produced thus meets the most stringent future specifications.
  • the conversion into products having a boiling point below 150 ° C is, across all two process steps, kept below a certain limit, beyond which it was found that the index cetane could be reduced due to the presence of aromatics. So the conversion into products with a boiling point below 150 ° C is, across all two process steps, less than 35%, preferably less than 30%, in particular less than 25% by weight.
  • the catalyst used during the hydrorefining step of the process of present invention also called hydrorefining catalyst, comprises on a amorphous mineral support, at least one metal from group VIB of the periodic table elements, at least one non-noble metal from group VIII of this same classification and at least one promoter element.
  • the metals of groups VIB and VIII constitute the element hydro-dehydrogenating hydrorefining catalyst.
  • the charge is brought into contact with a hydrorefining catalyst comprising at least one support, at least one element of group VIB of the periodic table, at least one element of group VIII of this same classification, at least one promoter element, the latter being deposited on said catalyst, possibly at least one element of group VIIB such as manganese, and possibly at least one element of the VB group such as niobium.
  • a hydrorefining catalyst comprising at least one support, at least one element of group VIB of the periodic table, at least one element of group VIII of this same classification, at least one promoter element, the latter being deposited on said catalyst, possibly at least one element of group VIIB such as manganese, and possibly at least one element of the VB group such as niobium.
  • the promoter element is chosen from the group consisting of phosphorus, boron, silicon and fluorine.
  • the hydrorefining catalyst comprises, as promoter elements, boron and / or silicon, as well as optionally and, preferably, phosphorus.
  • the contents of boron, silicon, phosphorus are then generally understood, for each of these elements, between 0.1 and 20% by weight, preferably between 0.1 and 15% by weight, in particular between 0.1 and 10% in weight.
  • the presence of phosphorus brings at least two advantages to the hydrorefining catalyst. Phosphorus facilitates the impregnation of nickel and molybdenum solutions, and it also improves the hydrogenation activity.
  • the amorphous mineral supports of the hydrorefining catalyst can be used alone or as a mixture.
  • These hydrorefining catalyst supports can be chosen among alumina, halogenated alumina, silica, silica-alumina, clays, magnesia, titanium oxide, boron oxide, zirconia, aluminum phosphates, phosphates titanium, zirconium phosphates, coal, aluminates.
  • the clays one can choose natural clays, such as kaolin or bentonite.
  • supports used contain alumina, in all these forms known to man of the trade, and even more preferably are aluminas, for example alumina gamma.
  • the hydro-dehydrogenating function of the hydrorefining catalyst is generally filled with at least one metal from group VIB of the periodic table and at least one non-noble metal from group VIII of this same classification, these metals preferably being chosen from molybdenum, tungsten, nickel and cobalt.
  • this function can be ensured by the combination of at least one element of the group VIII (Ni, Co) with at least one element from group VIB (Mo, W).
  • the hydrorefining catalyst comprising phosphorus is such that the total concentration of metal oxides of groups VIB and VIII is between 5 and 40% by weight, preferably between 7 and 30% by weight. weight.
  • the weight ratio expressed as metal oxide between metal (or metals) of group VIB over metal (or metals) of group VIII is, for its part, preferably between 20 and 1.25, even more preferably between 10 and 2
  • the concentration of phosphorus oxide P 2 O 5 in this catalyst is preferably less than 15% by weight, in particular less than 10% by weight.
  • Such a hydrorefining catalyst exhibits activity in hydrogenation of aromatic hydrocarbons, hydrodenitrogenation and greater hydrodesulfurization than catalytic formulas without boron and / or silicon.
  • This type of catalyst has also a higher hydrocracking activity and selectivity than the catalytic formulas known in the prior art.
  • a catalyst comprising boron and silicon is particularly active, which induces, on the one hand, an improvement in hydrogenating, hydrodesulfurizing, hydrodenitrogenating properties and, on the other hand, a improvement in hydrocracking activity compared to the catalysts used usually in hydroconversion hydrorefining reactions.
  • the preferred hydrorefining catalysts are NiMo and / or NiW catalysts on alumina, also NiMo and / or NiW catalysts on alumina doped with at least one element included in the group of atoms consisting of phosphorus, boron, silicon and fluorine.
  • Other preferred catalysts are the NiMo and / or NiW catalysts on silica-alumina or on silica-alumina-oxide of titanium, doped or not, with at least one element included in the group of atoms consisting of phosphorus, boron, fluorine and silicon.
  • the hydrorefining stage is advantageously carried out at a pressure ranging from 5 to 15 MPa, preferably from 6 to 13 MPa, even more preferably from 7 to 11 MPa and at a temperature ranging from 310 ° C to 420 ° C , preferably from 320 to 400 ° C, even more preferably from 340 to 400 ° C.
  • the recycling of pure hydrogen per volume of charge may advantageously be between 200 and 2,500 Nm 3 / m 3 of charge, preferably between 300 and 2,000 Nm 3 / m 3 .
  • the space velocity can be, for its part, between 0.1 and 5, preferably between 0.1 and 3 expressed in volume of liquid charge per volume of catalyst and per hour.
  • the target organic nitrogen content is generally less than 50 ppm by mass, of preferably less than 20 ppm, in particular less than 10 ppm by mass.
  • all of the products from the hydrorefining stage are used in the subsequent stage of the process of the invention.
  • the hydrorefining stage and the subsequent stage generally take place in at least two separate reaction zones. These areas reaction vessels can be contained in one or more reactors.
  • the characteristics of the catalyst of the subsequent stage can match those of the catalysts that can be used during the step hydrorefining, said characteristics having been presented above.
  • the catalyst of the subsequent stage of the process of the invention can have the characteristics described below.
  • the hydro-dehydrogenating function of the catalyst is generally ensured by at least an element of group VIB (for example molybdenum and / or tungsten) and at least one non-noble group VIII element (for example cobalt and / or nickel) of the classification of the elements.
  • group VIB for example molybdenum and / or tungsten
  • non-noble group VIII element for example cobalt and / or nickel
  • a preferred subsequent step catalyst essentially comprises at least one oxide mixed chosen from the group consisting of amorphous silica-aluminas, silica-alumina-titanium, silica-alumina-zirconia, as well as nickel, molybdenum.
  • the catalyst of the subsequent stage of the process of the invention comprises, in in addition, at least one promoter element chosen from boron, phosphorus and silicon.
  • the catalyst can also comprise at least one element of group VIIA (chlorine or fluorine for example), at least one element of group VIIB (manganese for example), at least one element of the VB group (niobium by example).
  • the catalyst of the subsequent stage of the process includes, as a promoter element, boron and / or silicon, as well as phosphorus.
  • concentrations introduced for each of these elements are generally between 0.1 and 20% by weight relative to the weight of the catalyst (calculated in oxide).
  • the elements introduced, in particular silicon, can be mainly located on the support matrix, and this also applies to the catalyst of the refining step.
  • These elements can be characterized by techniques, such as a microprobe. Casting giving a distribution profile of these various elements, a microscopy electronic transmission coupled with an X-analysis of the catalyst components, or again by establishing a distribution map of the elements present in the catalyst by electron microprobe.
  • this catalyst may further comprise an inorganic binder.
  • the preferred binders are silica and alumina, and even more preferably alumina in all known forms to a person skilled in the art, for example gamma alumina.
  • the content by weight of binder in the catalyst support can be between 0 and 40%, preferably between 1 and 40%, in particular between 5% and 20%. As a result, the weight content of mixed oxide varies from 60 to 100%.
  • a catalyst whose support consists only of mixed oxides does not include no binder.
  • the support can be prepared by shaping the mixed oxide chosen from the group consisting of silica-alumina, silica-alumina-zirconia, and silica-alumina-titanium, presence or absence of binder, by any technique known to those skilled in the art.
  • the shaping can be carried out for example by extrusion, by tableting, by the method coagulation in drop (oil-drop), by granulation on the turntable or by any another method well known to those skilled in the art.
  • At least one calcination step can be performed after any of the preparation steps. This calcination is usually carried out in air at a temperature of at least 150 ° C, preferably at least 300 ° C.
  • the metals of group VIB and group VIII of the catalyst of the present invention may be present in whole or in part in the metallic and / or oxide form and / or sulfide.
  • the catalysts of the two stages of the process according to the invention can be prepared according to all methods well known to those skilled in the art.
  • the subsequent step is advantageously carried out at a pressure ranging from 5 to 15 MPa, preferably from 6 to 13 MPa, even more preferably from 7 to 11 MPa and at a temperature ranging from 310 to 420 ° C, preferably from 320 ° C to 400 ° C, more preferably 340 to 390 ° C.
  • the recycling of pure hydrogen can be between 200 and 2500 Nm 3 / m 3 , preferably between 300 and 2000 Nm 3 / m3.
  • each of the catalysts Prior to the hydrorefining stage and / or the subsequent stage of the process of the present invention, each of the catalysts can be subjected to a sulfurization treatment making it possible to transform, at least in part, the metallic species into sulphide before bringing them into contact with the load to be treated.
  • This sulfurization activation treatment is well known to the skilled person and can be carried out by any method already described in the literature either in situ, that is to say in the reactor, or ex-situ.
  • a conventional sulfurization method well known to those skilled in the art consists in heating in the presence of hydrogen sulfide (pure or for example under a mixture flow hydrogen / hydrogen sulfide) at a temperature between 150 and 800 ° C, preferably between 250 and 600 ° C, generally in a crossed bed reaction zone.
  • hydrogen sulfide pure or for example under a mixture flow hydrogen / hydrogen sulfide
  • the effluent leaving the second reaction zone corresponding to the subsequent stage of the process according to the invention may be subjected to a so-called final separation (for example atmospheric distillation) so as to separate the gases (such as ammonia NH 3 and hydrogen sulfide (H 2 S), as well as the other light gases present, hydrogen and conversion products (petrol cut).
  • a so-called final separation for example atmospheric distillation
  • the feedstock treated in this example is a naphtheno-aromatic diesel fuel obtained from a distillation and the characteristics of which are as follows: Physico-chemical characteristics of the charge d-15/4 0.9045 S content (% by weight) 2.2 Cetane engine 34 Aromatics content (including polyaromatics) 47.2 Polyaromatic content 20.4 T95 (° C) 351
  • This charge is introduced into a catalytic test unit comprising 2 reactors.
  • a hydrorefining catalyst comprising alumina, 3.6% by weight of nickel (oxide), 17.2% by weight of molybdenum (oxide) and 4% by weight of phosphorus (oxide).
  • This same catalyst is used in the downstream reactor corresponding to the second step of the process of the invention.
  • the yield of the diesel fraction at 150 ° C + is 93.5% by weight.
  • the table above shows that all the characteristics of the 150 ° C + diesel cut obtained by the process according to the invention are improved and make it possible to meet the most severe future specifications.

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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)
EP03290339A 2002-02-15 2003-02-11 Verfahren zur Aufwertung von Aromaten und Naften-Aromaten enthaltenden Gasölschnitten. Ceased EP1336648A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0201970 2002-02-15
FR0201970A FR2836149B1 (fr) 2002-02-15 2002-02-15 Procede d'amelioration de coupes gazoles aromatiques et naphteno-aromatiques

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EP1336648A1 true EP1336648A1 (de) 2003-08-20

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EP03290339A Ceased EP1336648A1 (de) 2002-02-15 2003-02-11 Verfahren zur Aufwertung von Aromaten und Naften-Aromaten enthaltenden Gasölschnitten.

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US (1) US7332071B2 (de)
EP (1) EP1336648A1 (de)
BR (1) BR0300308B1 (de)
FR (1) FR2836149B1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1323141C (zh) * 2004-08-31 2007-06-27 中国石油化工股份有限公司 一种提高柴油产品收率和质量的降凝方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11318453B2 (en) 2009-04-21 2022-05-03 Albemarle Catalysts Company B.V. Hydrotreating catalyst containing phosphorus and boron
WO2011022888A1 (zh) 2009-08-28 2011-03-03 南京工业大学 一种介孔复合氧化钛及其制备方法
US20140174988A1 (en) * 2012-12-21 2014-06-26 Exxonmobil Research And Engineering Company Hydroprocessing configuration for low sulfur diesel

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0277718A2 (de) * 1987-02-02 1988-08-10 Union Oil Company Of California Katalytische Hydrogenierung von Aromaten in Kohlenwasserstoffen
US5118406A (en) * 1991-04-30 1992-06-02 Union Oil Company Of California Hydrotreating with silicon removal
EP0848992A1 (de) * 1996-12-17 1998-06-24 Institut Francais Du Petrole Bor und Silicium enthaltender Katalysator und Anwendung dieses in der Hydrobehandlung von Kohlenwasserstoffeinsätzen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3637484A (en) * 1970-06-18 1972-01-25 Union Oil Co Platinum group metal on silica-alumina hydrogenation catalyst and process
US3703461A (en) * 1971-07-16 1972-11-21 Union Oil Co Hydrogenation process and catalyst
US6387246B1 (en) * 1999-05-19 2002-05-14 Institut Francais Du Petrole Catalyst that comprises a partially amorphous Y zeolite and its use in hydroconversion of hydrocarbon petroleum feedstocks
NZ534414A (en) * 2004-07-29 2005-10-28 Data Acquisitions Ltd Data logging and transmitting device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0277718A2 (de) * 1987-02-02 1988-08-10 Union Oil Company Of California Katalytische Hydrogenierung von Aromaten in Kohlenwasserstoffen
US5118406A (en) * 1991-04-30 1992-06-02 Union Oil Company Of California Hydrotreating with silicon removal
EP0848992A1 (de) * 1996-12-17 1998-06-24 Institut Francais Du Petrole Bor und Silicium enthaltender Katalysator und Anwendung dieses in der Hydrobehandlung von Kohlenwasserstoffeinsätzen

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1323141C (zh) * 2004-08-31 2007-06-27 中国石油化工股份有限公司 一种提高柴油产品收率和质量的降凝方法

Also Published As

Publication number Publication date
BR0300308A (pt) 2004-08-03
FR2836149B1 (fr) 2004-04-09
FR2836149A1 (fr) 2003-08-22
BR0300308B1 (pt) 2013-11-26
US7332071B2 (en) 2008-02-19
US20040020825A1 (en) 2004-02-05

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