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WO1999049002A1 - Procede d'hydrogenation - Google Patents

Procede d'hydrogenation Download PDF

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Publication number
WO1999049002A1
WO1999049002A1 PCT/FI1999/000221 FI9900221W WO9949002A1 WO 1999049002 A1 WO1999049002 A1 WO 1999049002A1 FI 9900221 W FI9900221 W FI 9900221W WO 9949002 A1 WO9949002 A1 WO 9949002A1
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WO
WIPO (PCT)
Prior art keywords
process according
zone
reactor
reaction zone
feed
Prior art date
Application number
PCT/FI1999/000221
Other languages
English (en)
Inventor
Juhani Aittamaa
Varpu Markkanen
Esa Lindgren
Sirpa Lonka
Original Assignee
Fortum Oil And Gas Oy
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fortum Oil And Gas Oy filed Critical Fortum Oil And Gas Oy
Priority to AU30367/99A priority Critical patent/AU3036799A/en
Publication of WO1999049002A1 publication Critical patent/WO1999049002A1/fr

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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
    • C10G45/44—Hydrogenation of the aromatic hydrocarbons

Definitions

  • the present invention relates to dearomatization of petroleum distillates containing aromatic compounds.
  • the invention concerns a process for removal of aromatic compounds from middle distillates containing sulphur compounds.
  • Such a process comprises the steps of feeding a middle distillate fraction into a hydrotreating process unit which includes a fractionation zone and a hydrogenation zone, contacting the feed with hydrogen in the presence of a catalyst in order to hydrogenate the distillate and the aromatic compounds contained therein to produce a dearomatized product, and recovering the dearomatized product from the hydrotreating process unit.
  • Hydrogenation is utilized in many refining, petrochemical and chemical applications. In petroleum refining aromatics removal is important because there are specified limits for benzene content in gasoline and for aromatics content in diesel fuels. And due to environmental and healthy concerns those limits will be reduced even more in the future.
  • the dearomatization process ofEP 0 781 830 A1 comprises two alternatives; viz. one in which all of the catalyst is placed in a side reactor and another one in which a part of the catalyst is placed within the column.
  • the sidedraw from the distillation column is conducted to the reactor.
  • Hydrogen is fed into the sidedraw and the dearomatized effluent of the hydrogenation reactor is recirculated to the distillation column.
  • the hydrogenation can be optimized and, if desired, carried out at conditions different from the operation pressure and temperature of the distillation column.
  • the present invention is based on hydrogenation of middle distillate fractions in a system comprising a distillation column and one or more side-reactors.
  • the sulphurous aromatic compounds contained in middle distillates are mainly high-boiling and they primarily gather in the bottom of a column during distillation of middle destillates.
  • a side-cut taken from a point intermediate to the top and bottom of the distillation column, in particular intermediate to the top and the feedpoint of the hydrocarbon feedstock, will contain less sulfur than the feed.
  • hydrocarbons are fed into a distillation column or a similar fractionation zone providing fractionation of the hydrocarbon feedstock to produce a different hydrocarbon composition on each stage of the fractionation zone.
  • a low-sulfur side-cut stream is withdrawn from the fractionation zone at a suitable stage and conducted to a reaction zone.
  • the dearomatized reactor effluent is recycled to the distillation column.
  • a dearomatized hydrocarbon product with sulfur compounds is recovered from the fractionation zone.
  • the invention is characterized by what is stated in the characterizing part of claim 1.
  • the operating conditions of the column and the reactor are independent of each other.
  • the operating temperatures and the pressures of the column and the reactor can be selected freely and optimised for each application. Further, no need for special tower packing character is required, hence commercial trickle bed -type catalysts are adequate. No need to shut-down the unit for change of the catalyst (in the case of two or more side-reactors). No additional product stripper is needed.
  • the present invention also provides important advantages compared to the prior art of EP 0 781 830 Al and US 5,177,283. Hydrogenation reactions are exothermic and temperature rise in reaction zone can be controlled by a liquid recycle.
  • reactor effluent is cooled and sent to a gas-liquid separator. Temperature rise in the reactor is then controlled by liquid recycle from that gas-liquid separator.
  • the gas mixture contains hydrogen and light C r C 4 hydrocarbons which can be recycled to the reactor and/or fed to fuel gas/hydrogen network. Liquid recycle is separated from the saturated hydrocarbons which are returned to the fractionation zone above or below the feed point of fractionation.
  • reaction zone effluent contains no unsaturated hydrocarbons because conversion in the reaction zone is 99 - 100 %.
  • the fractionation zone is used as a product stabilizer for the reaction zone effluent which contains hydrogen and small amount of light hydrocarbons.
  • the dearomatized product is recovered from the fractionation zone as bottoms, which provides for stabilization of the product. It can, however, also be recovered as a sidedraw.
  • Figure 1 depicts in a schematic fashion the process configuration of a preferred embodiment of the invention
  • aromatics designates any aromatic compounds present in a petroleum-based hydrocarbon feed.
  • alkyl- substitued aromatics such as butylbenzene, pentylbenzene and indene (C 9 H 8 ).
  • Haldrogenation and “dearomatization” are used interchangeably to denote a process, wherein unsaturated bonds of aromatic compounds are saturated by reacting the compounds with hydrogen (H 2 ).
  • Middle distillates is an aromatic feedstock commonly used, for instance, as a fuel for diesel engines, comprising mainly C 9 -C 20 hydrocarbons and having a boiling point area of about 150-400 °C, in particular 200 to 320 °C. It contains some 10 to 70 vol.-% aromatics before hydrogenation.
  • Typical middle distillates are represented by straight run or cracked gasoil, FCC gasoil and visbreaker gasoil.
  • the middle distillate feedstock of the present hydrogenation process is preferably subjected to a separate conventional desulfurization process, gasoil hydrotreater, before being fed into the present process.
  • the "sulfur compounds" of the middle distillates are mainly sulfides, disulfides, thiophenes, benzothiophenes, dibenzothiophenes and alkyl dibenzothiophenes.
  • the lighter sulphur compounds are most easily hydrogenated and the heavy compounds are the last to react. Therefore, a gasoil which has undergone desulfurization does not contain light sulfides, thiophenes or benzothiophenes.
  • the distribution of dibenzothiophenes in the gasoil depends on the effectiveness of the desulfurization process, i.e. on the total sulphur content of the gasoil.
  • Typical residual sulfur compounds are 4,6-dimethyldibenzothiophene (4,6-DMDBT), 4-methyldibenzo- thiophene and dibenzothiophene.
  • a petroleum distillate feed containing C 9 -C 20 hydrocarbons, like naftenes, parafmes and aromatics, and polyaromatic sulfur compounds, like benzothiophenes and alkyl dibenzothiophenes, is fed to a fractionation zone.
  • the fractionation zone includes a column, a reboiler, a condenser and an overhead drum.
  • the feed contains 20 - 30 vol-% aromatics and 1 - 100 ppm-wt sulfur. From fractionation an overhead stream and a bottoms stream can be obtained having different hydrocarbon compositions.
  • the fractionation zone is operated so as to provide a different hydrocarbon composition in each stage of the zone.
  • the typical operating pressure range of the fractionation zone is 200 - 700 kPa.
  • the temperature profile of the fractionation zone depends on the operating pressure and feed composition and should be optimized case by case.
  • the lighter fraction is taken from the fractionation zone as a side-cut stream and hydrogenated in a reaction zone.
  • the hydrogenated stream from the reactor(s) is then recycled to the fractionation zone.
  • Preferably the side-cut flow is taken from the fractionation zone above the fractionation feed point.
  • the dearomatized reactor effluent can be recycled to the fractionation zone to a stage below the feed point (stage).
  • the effluent from the reaction zone can be divided into two streams, the first of which is recycled to the reaction zone and the second of which is recycled to the fractionation zone (1).
  • the first stream can be combined with the side draw fed to the reaction zone.
  • the side draw fed into the reaction zone contains less sulfur than the middle distillate feed.
  • the decrease in the sulfur content is at leat 50 %, in particular at least 90 %, so that the side draw generally contains a maximum of 50 ppm-wt sulfur.
  • the reaction zone includes heat exchangers, a trickle-bed type reactor and gas-liquid separator.
  • the feed from the fractionation zone containing typically less than 50 ppm-wt, in particular 0 - 10 ppm-wt sulphur, and 10 - 30 vol-% aromatics, is cooled or heated to the 7 optimal reaction temperature before it is conducted into the reactor.
  • the temperature at the reactor inlet depends on feedstock properties, on the hydrogenated aromatics and on the catalyst used. Aromatics are saturated in the presence of hydrogen and an active hydrogenation catalyst.
  • the hydrogen used for hydrogenation can be comprised of hydrogen gas of any suitable purity (typically 10 - 100 wt-%).
  • the gas can contain 0 to about 90 wt-%, preferably only 10 to 70 wt-% of other volatile components, such as hydrocarbons, which remain inert during hydrogenation.
  • hydrogen gas containing up to about 50 to 60 wt-% of methane and other light paraffinic hydrocarbons can be employed.
  • hydrogenation can be carried out at the following conditions: - hydrogen-to-hydrocarbons -ratio: 100 to 500 Nm 3 hydrogen/m 3 hydrocarbons of the feedstock,
  • LHSV space velocity
  • the feed temperature typically lies in the range of 250 to 350 °C and the pressure is 35 to 60 bar.
  • the temperature rise is kept below 60 °C during the reaction.
  • the feed is diluted with the reaction zone effluent to lower the concentration of aromatics in the feed by cooling the effluent and partially recycling it to the reaction zone.
  • the ratio of effluent recycle to fresh feed rate is 0.1 to 5, preferably about 0.2 to 3, and in particular about 0.5 to 3.
  • the temperature rise in the reactor during hydrogenation can be restricted to less than 60 °C.
  • the temperature rise across the reactor is about 20 to 60 °C.
  • a maximum aromatics concentration of about 16 vol.-%.
  • the cooled effluent or liquid reaction product is recycled from a gas separator vessel.
  • reaction temperature rise can be restricted by hydrogen quenching.
  • hydrogen is recirculated from the reactor effluent and fed into the reactor between the reaction beds.
  • Hydrogen quenching can also be used to lower the temperature of the effluent feed between two serially arranged reactors, and it can be carried out by using make-up hydrogen.
  • Hydrogen-rich gas is separated from the liquid product in product separator and recycled to the reactor feed. To remove impurities in recycle gas some of the gas is bled to fuel gas or hydrogen net work.
  • the ratio of recycled hydrogen to make-up hydrogen is about 0.1 to 10.
  • the make-up hydrogen is somewhat richer in hydrogen: make-up contains, e.g., 89 to 92 mol-% H 2 and recycle, e.g., 85 to 90 mol-% H 2 .
  • the process according to the present invention is carried out in a hydrotreating unit comprising at least one reactor, preferably two reactors arranged in series (in a cascade). It is also possible to arrange the reactors in parallel. As far as the basic concept of the invention is concerned, satisfactory results are obtained already with one hydrogenation reactor. However, because of the possibility of poisoining of the catalyst, two or more reactors are preferred to ensure continuous operation. Thus, when the catalyst in the first hydrogenation reactor is deactivated, the second reactor can be used, and the production continued. The cost of a reaction vessel together with necessary instruments is minor to the cost of production losses. Furthermore, the use of two reactors will reduce the amount of catalyst needed, because only the operative reactor needs to be filled with catalyst.
  • the liquid reactor outlet from the first reactor can be cooled in a heat exchanger to the feed temperature of the first reactor, before it is fed into a second reactor or before a part thereof is recycled to the inlet of the reactor.
  • the reactors can be of any suitable type for contacting liquid with gas, trickle bed reactors being particularly preferred.
  • the saturated hydrocarbon stream contains some hydrogen and light (C,-C 4 ) hydrocarbons which are removed in the fractionation zone.
  • the distillate of the fractionation zone contains saturated hydrocarbons.
  • the bottom product of the fractionation zone contains hydrogenated hydrocarbons, polyaromatic sulphur compounds and small amounts of unsaturated heavier aromatics which were separated from the reaction zone feed. Depending on the operating conditions the overall aromatics conversion of 50 - 95 % can be achieved.
  • the aromatics of a hydrocarbon feedstock are hydrogenated in the presence of a catalyst which is active in the temperature range of 50 to 300 °C.
  • Suitable catalysts are heterogeneous catalyst comprising a metal of group VIII on a solid support.
  • Preferred metals are nickel, iron, platinum and palladium, and preferred supports are silica, alumina, magnesia, zirconia, titanium oxide, and natural and synthetic aluminium and magnesium silicates including natural and synthetic zeolites.
  • hydrogenation is carried out in the presence of a nickel catalyst, for instance a catalyst comprising elemental nickel on an inorganic metal oxide support.
  • Such a catalyst can comprise 0.1 to 70 wt-%, preferably 1 to 50 wt-% nickel on an alumina or silica support.
  • the selection of the catalyst depends on the amount of sulfur in the feed of the reactor.
  • the afore-mentioned nickel catalyst is suitable for low-sulfur feeds.
  • Pt and/or Pd catalysts give longer operation cycles.
  • the supports of these noble metal catalysts comprise alumina, silica or zeolite.
  • the process according to the present invention solves the problem of removing heavier 10 aromatics from sulfuric petroleum distillates.
  • the sulfur compound in the feed are heavier polyaromatic sulphur compounds, like benzothiophenes, dibenzothiophenes and alkyl dibenzothiophenes.
  • the hydrogenated heavier aromatics are alkyl benzenes, like butylbenzene, pentylbenzene etc.
  • the process for hydrogenation of hydrocarbon feed in the distillation column with a side-cut stream to a reaction zone is especially advantageous for removing aromatics from from sulfuric petroleum distillates. With this configuration an overall conversion of up to 95 % can be achieved.
  • the sulfur specification for gasoils and similar middle distillates used as fuel for diesel engines is 500 ppm in many countries (e.g. U.S.A., Europe and Japan).
  • the catalyst used for hydrogenation of aromates requires an essentially sulfur-free middle distillate feed (less than 50 ppm, preferably less than 10 ppm and in particular less than 5 ppm).
  • the present process makes it possible to treat sulfurous feeds containing 50 to 100 ppm sulfur without any impact on the effective service life of the dearomatization catalyst.
  • the costs of operation are reduced because a higher desulfurization degree would require higher temperature in the desulfurization reactor and higher operational temperature increase energy and catalyst consumption in the desulfurization section.
  • Figure 1 shows an embodiment particularly suited to the dearomatization of hydrocarbon fractions.
  • the hydrocarbon feed containing aromatics is fed to a fractionation zone 1 - 5 at a feed point 2.
  • the feed has preferably been subjected to desulfurization in a reactor not shown in the figure.
  • the fractionation zone includes a column 1, a reboiler 3, a condenser 4 and an overhead drum 5. In the fractionation zone heavier hydrocarbons and sulfur compounds are separated from the lighter components.
  • the lighter fraction is taken from the fractionation zone as a side-cut stream 6 and hydrogenated in a reaction zone (7 - 10) .
  • the typical operating pressure range of the fractionation zone is 200 - 700 (or even higher, up to 1100) kPa.
  • the temperature profile of the fractionation zone depends on the operating pressure and feed composition.
  • the reaction zone includes heat exchangers 8, 9, a trickle-bed type reactor 7 and gas-liquid separator 10.
  • the feed from the fractionation zone is cooled or heated in the heat exchanger 11
  • the temperature at reactor inlet depends on the feedstock properties and hydrogenated aromatics and the catalyst used. Aromatics are saturated in the presence of hydrogen and an active hydrogenation catalyst.
  • the H 2 gas feed to the reaction zone contains 90-95 mol-% hydrogen and small amount of light hydrocarbons.
  • the pressure in reaction zone is typically 3500 - 5500 kPa. Space velocity range is 0.5-10 1/h.
  • Reactor effluent is cooled and sent into the gas-liquid separator 10. Temperature rise in the reactor is controlled by a liquid recycle (line 11) from a gas-liquid separator 10.
  • the gas mixture obtained from the separator contains hydrogen and light C,-C 4 hydrocarbons which can be recycled to the reactor and/or fed to fuel gas/hydrogen network. Liquid recycle is separated from the saturated hydrocarbons which are returned to the fractionation zone above or below feed point 12.
  • a middle distillate feed containing 50 ppm-wt polyaromatic sulphur compounds including dibenzothiophene, 4-methyldibenzothiophene and 4,6-dimethyldibenzothiophene was fed to a fractionation zone.
  • the aromatic content of the feed was 23.5 wt-% C 10 -C 13 mono- and diaromatics.
  • the contents of the feed and the products are illustrated in Table 1.
  • the fractionation zone included a column, a reboiler, a condenser and an overhead drum. In the fractionation zone heavier hydrocarbons including polyaromatic sulphur compounds were separated from the lighter components.
  • the lighter fraction was taken from the fractionation zone as a side-cut stream and hydrogenated in a reaction zone.
  • the operating pressure of the fractionation zone was 250 kPa.
  • the temperature at the top of the column was 153 °C and 263 °C in the bottom of the column.
  • the reaction zone included heat exchangers, a trickle-bed type reactor and gas-liquid separator.
  • the feed from fractionation zone contained less than 1 ppm-wt sulfur, was cooled to the optimal reaction temperature before 12 it was subjected into the reactor.
  • Aromatics were saturated in the presence of hydrogen and an active hydrogenation catalyst.
  • the H 2 gas feed to the reaction zone contained 92 mol-% hydrogen and small amount of C C 4 - hydrocarbons.
  • the pressure in reaction zone was 4,000 kPa and the temperature at reactor inlet was 180 °C. Temperature rise in the reactor was controlled by a liquid recycle from a gas-liquid separator. The aromatics conversion of 99 - 100 % was achieved in the reactor zone.
  • Reactor effluent was cooled to a temperature of 40 °C and sent into the gas-liquid separator. Gas mixture containing hydrogen and light Cj-C 4 hydrocarbons was recycled to the reactor. Liquid recycle was separated from the saturated hydrocarbons which were returned to the fractionation zone below the feed point of the fractionation.
  • the saturated hydrocarbons from reaction zone contained some hydrogen and C r C 4 - hydrocarbons which were removed in the fractionation zone.
  • the liquid distillate of the fractionation zone contained light C,-C 9 hydrocarbons.
  • the bottom product of the fractionation zone contained saturated hydrocarbons, polyaromatic sulphur compounds and 4.8 wt-% unsaturated heavier aromatics. An overall aromatics conversion of 80 % was achieved.
  • a middle distillate feed (C 10 -C 20 hydrocarbons) containing heavier aromatics having up to 16 carbon atoms and 100 ppm-wt polyaromatic sulfur compounds was fed to the distillation equipment illustrated in Example 1.
  • the aromatic content of the feed was 26 wt-%.
  • the temperature at the top of the column was 157 °C and 277 °C in the bottom of the column.
  • a side-cut flow which was taken from the fractionation zone above the fractionation feed point contained sulfur compounds less than 1 ppm-wt.
  • the bottoms product of the fractionation zone contained saturated hydrocarbons, polyaromatic sulfur compounds and 11.6 wt-% unsaturated heavier aromatics. An overall aromatics conversion of 57 % was achieved.

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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)

Abstract

La présente invention concerne un procédé d'hydrogénation d'une charge de distillat moyen contenant des composés sulfurés et des composés aromatiques. L'invention consiste à introduire la charge de distillat moyen dans une zone de fractionnement (1) qui fonctionne dans des conditions suffisant à produire un flux de distillat de tête et un flux de résidus ayant une composition hydrocarburée différente. On retire un soutirage (6) contenant des composés aromatiques et moins de soufre que la charge de distillat moyen, et on le dirige vers une zone de réaction (7), dans laquelle on le met en contact avec un hydrogène en présence d'un catalyseur, afin d'hydrogéner les composés aromatiques qu'il renferme. On recycle l'effluent désaromatisé (12) de la zone de réaction (7) dans la zone de fractionnement (1), et on récupère de la zone de fractionnement un produit hydrocarboné désaromatisé. La présente invention présente des avantages significatifs. Du fait que l'hydrogénation se fait dans un réacteur secondaire, les composés sulfurés et d'autres poisons catalytiques sont séparés de la charge du réacteur et fractionnés au fond, ce qui augmente la durée du cycle catalytique.
PCT/FI1999/000221 1998-03-20 1999-03-22 Procede d'hydrogenation WO1999049002A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30367/99A AU3036799A (en) 1998-03-20 1999-03-22 Hydrogenation process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI980637A FI103803B (fi) 1998-03-20 1998-03-20 Hydrausprosessi
FI980637 1998-03-20

Publications (1)

Publication Number Publication Date
WO1999049002A1 true WO1999049002A1 (fr) 1999-09-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FI1999/000221 WO1999049002A1 (fr) 1998-03-20 1999-03-22 Procede d'hydrogenation

Country Status (3)

Country Link
AU (1) AU3036799A (fr)
FI (1) FI103803B (fr)
WO (1) WO1999049002A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5177283A (en) * 1992-02-03 1993-01-05 Uop Hydrocarbon conversion process
WO1996027580A1 (fr) * 1995-03-06 1996-09-12 Chemical Research & Licensing Company Hydrogenation de composes cycliques insatures
EP0781830A1 (fr) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Procédé de réduction sélective de la teneur en benzène et en composés insaturés légers d'une coupe d'hydrocarbures
EP0794241A2 (fr) * 1996-03-05 1997-09-10 Neste Oy Procédé pour la désaromatisation de distillats pétrolières

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5177283A (en) * 1992-02-03 1993-01-05 Uop Hydrocarbon conversion process
WO1996027580A1 (fr) * 1995-03-06 1996-09-12 Chemical Research & Licensing Company Hydrogenation de composes cycliques insatures
EP0781830A1 (fr) * 1995-12-27 1997-07-02 Institut Francais Du Petrole Procédé de réduction sélective de la teneur en benzène et en composés insaturés légers d'une coupe d'hydrocarbures
EP0794241A2 (fr) * 1996-03-05 1997-09-10 Neste Oy Procédé pour la désaromatisation de distillats pétrolières

Also Published As

Publication number Publication date
FI980637A7 (fi) 1999-09-21
FI103803B1 (fi) 1999-09-30
FI980637A0 (fi) 1998-03-20
AU3036799A (en) 1999-10-18
FI103803B (fi) 1999-09-30

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