EP1417283B1 - Verfahren zur isomerisierung von c5-c8 kohlenwasserstofffreaktionen mit zwei parallelreaktoren - Google Patents

Verfahren zur isomerisierung von c5-c8 kohlenwasserstofffreaktionen mit zwei parallelreaktoren Download PDF

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Publication number
EP1417283B1
EP1417283B1 EP02767555A EP02767555A EP1417283B1 EP 1417283 B1 EP1417283 B1 EP 1417283B1 EP 02767555 A EP02767555 A EP 02767555A EP 02767555 A EP02767555 A EP 02767555A EP 1417283 B1 EP1417283 B1 EP 1417283B1
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EP
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Prior art keywords
isomerization
fraction
effluents
carbon atoms
catalysts
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English (en)
French (fr)
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EP1417283A1 (de
Inventor
Christophe Bouchy
Olivier Ducreux
Elsa Jolimaitre
Paul Broutin
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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    • 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
    • C10G65/14—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural parallel stages only

Definitions

  • the present invention relates to an isomerization process in the presence of hydrogen (also sometimes called hydro-isomerization process), a feedstock comprising in majority hydrocarbons containing from 5 to 8 carbon atoms per molecule.
  • hydrogen also sometimes called hydro-isomerization process
  • C5-C8 cut will be used to designate a feedstock comprising, for the most part, normal paraffins containing from 5 to 8 carbon atoms per molecule.
  • the product of the isomerization (or isomerate) is aromatic-free in contrast to the reformate which usually contains a significant amount (80 mol% and more).
  • Isomerate and reformate are usually sent to the gasoline pool in which other bases or additives may also be involved: gasoline resulting from fluidized catalytic cracking (FCC), alkylation products, methyl-tertiobutyl-ether (MTBE), etc.
  • FCC fluidized catalytic cracking
  • MTBE methyl-tertiobutyl-ether
  • the patent application EP-A1-922747 proposes, for limiting the cracking rate of paraffins containing at least 7 carbon atoms per molecule during the isomerization of a C5-C8 cut, the use of an acid catalyst associated with relatively mild operating conditions.
  • This catalyst contains at least one halogen and at least one Group VIII metal, the reaction being carried out at a temperature between 30 and 150 ° C.
  • the patent application EP-A2-0256604 describes a process for the isomerization of paraffins of a feedstock comprising hydrocarbons containing from 5 to 7 carbon atoms per molecule without, in particular, the ratios R of the number of moles of hydrogen relative to the number of moles of hydrocarbons leaving from at least one reaction zone corresponds to the present invention.
  • the patent US3619408 describes a process for the isomerization of olefins, diolefins and aromatics of a feedstock comprising hydrocarbons containing from 5 to 8 carbon atoms per molecule without, in particular, the ratios R of the number of moles of hydrogen over the number of moles of hydrocarbons leaving at least one reaction zone corresponding to the present invention.
  • the patent US5994607 describes a process for the isomerization of paraffins of a feedstock comprising hydrocarbons containing from 5 to 8 carbon atoms per molecule without, in particular, the ratios R of the number of moles of hydrogen relative to the number of moles of hydrocarbons exiting from to at least one reaction zone corresponds to the present invention.
  • the present invention makes it possible to substantially improve the octane numbers of the products obtained by isomerization of a feed comprising mainly hydrocarbons containing from 5 to 8 carbon atoms, and possibly a significant amount of hydrocarbons containing from 2 to 4 carbon atoms (at least 0.1% by weight).
  • said feedstock is itself a naphtha (C5-C10 + cut), said fractionation then resulting in a fraction A (C5-C6) optionally also comprising C2-C4 hydrocarbons, a B fraction (C7-C8) and a heavy fraction C containing predominantly the heavier hydrocarbons of the initial naphtha fraction, ie containing at least 8 carbon atoms.
  • said reaction zones contain chemically different isomerization catalysts.
  • the isomerizing activity of the catalyst treating fraction A is greater than the isomerizing activity of the catalyst treating fraction B.
  • the isomerization catalysts of the process according to the invention are typically included in the group consisting of: the catalysts most often supported by a mineral support, typically an oxide and containing at least one halogen and at least one group VIII metal, the zeolitic catalysts, containing at least one Group VIII metal, Friedel and Crafts catalysts, acid or super acid catalysts of the type HPA (heteropolyanions) on zirconia, WOx (tungsten oxides) on zirconia, sulphated zirconias.
  • Said catalysts WOx (tungsten oxides) on zirconia are for example described in "Oxide Catalysts and Catalyst Development, PHILLIPS MJ and TERNAN M.
  • HPA type catalysts are for example described in "Heteropoly and Isopoly Oxometalates, Springer-Verlag, Thor Pope, Berlin Heidelberg New York Tokyo 1983” or in the French patent FR2795340 .
  • Other catalysts having an acidity comparable to that of catalysts mentioned above can also be used, for example catalysts comprising at least one mica and / or trioctaedric vermiculites with pillars.
  • the total pressure in the isomerization zones is typically about 0.1 to 10 MPa relative, the hourly space velocity being about 0.2 to 10 h -1 .
  • At least one of the isomerization reactions can be carried out in the presence of an excess of hydrogen such that the ratio R of the number of moles of hydrogen to the number of moles of hydrocarbons leaving the at least one reaction zone is between 0.06 and 0.3.
  • At least one of the isomerization reactions is carried out in the presence of an excess of hydrogen such that the ratio R of the number of moles of hydrogen to the number of moles of hydrocarbons leaving at least one zone reaction is between 0.3 and 30 and greater than 0.3.
  • the excess hydrogen is recycled to the inlet of the reactor, for example by means of a recycle compressor after separation of the cracking gases.
  • the isomerate resulting from the isomerization of the fractions A and B it is possible to mix the isomerate resulting from the isomerization of the fractions A and B. It is also possible to separate said mixture into two effluents, the first of said effluents comprising most of the isopentane and paraffins having at least two branches, the second of said effluents comprising most of the normal paraffins and paraffins containing at least six carbon atoms and a single branch, said second effluent being recycled and mixed with the feed or with the fraction B.
  • isomerization B is separated from the isomerization of fraction B into two effluents, the first of said effluents comprising most of the isopentane and paraffins having at least two branches, the second of said effluents comprising most of the normal paraffins and paraffins containing at least six carbon atoms and a single branch.
  • Said second effluent is optionally recycled, ie for example mixed with the feedstock or with fraction B.
  • the first effluent will advantageously be mixed with the isomerization resulting from the isomerization of the fraction A.
  • the isopentane fraction and paraffins having at least two branches and / or the fraction of normal paraffins and paraffins containing at least six carbon atoms and a single branch contained in each of the effluents in each of the embodiments of the invention. will obviously depend on the nature of the separation means used.
  • Said separation of said one or more isomerate in two effluents will be carried out according to any known technique or process of the prior art, preferably by gas phase adsorption, on molecular sieves by PSA methods, ie known to those skilled in the art. under the Anglo-Saxon term “pressure swing adsorption” or counter-current simulated.
  • Said separation will advantageously employ at least one zeolitic adsorbent whose structural type is included in the group constituted, according to the reference " Atlas of Zeolite Structure Types, M.
  • the isomerization A resulting from the isomerization of the fraction A into two effluents, the first of the said effluents comprising most of the isopentane and paraffins having at least one branch, the second said effluents comprising most of the normal paraffins, said second effluent being recycled and mixed with the feed or with the fraction A.
  • said first effluent resulting from isomerate A and said first effluent from isomerate B will be advantageously mixed.
  • Said separation of said one or more isomers resulting from the isomerization of the fraction A into two effluents will be carried out according to any known technique, in particular by a distillation column of the deisohexanizer type, by gas phase adsorption on a molecular sieve, for example according to the processes described. in patents US 5,233,120 or US 5,602,291 . Said separation will advantageously employ an adsorbent as described in the patent US 2,882,243 .
  • the operating conditions are as follows:
  • the isomerization reactor is fed with a feed comprising hydrocarbons containing from 5 to 7 carbon atoms (C5-C7) with a flow rate of 87 g / h, said feed containing 800 ppm of perchlorethylene.
  • the mass of catalyst present in the reactor is 86 g, the PPH of 1.01 h -1 .
  • the hydrogen flow rate is 4.5 l / h.
  • the total pressure is 3 MPa relative.
  • the isomerization is carried out at a temperature of 115 ° C. and the ratio R of the number of moles of hydrogen to the number of moles of hydrocarbons at the outlet of the reactor is equal to 0.11. The results obtained are shown in Table 1.
  • Example 1 The same IS 612 A catalyst is used as in Example 1 in two different isomerization reactors: reactor A for a synthetic feed containing predominantly hydrocarbons containing 5 or 6 carbon atoms (C5-C6 feedstock) and reactor B for a reactor. synthetic filler mainly containing hydrocarbons containing 7 carbon atoms C7). By mixing the charges A and B, an initial charge C5-C7 identical to that of Example 1 is obtained.
  • the isomerization reactor A is fed with the feed C5-C6 with a flow rate of 20.21 g / h (gram per hour), said feed containing 800 ppm by weight of perchlorethylene (C 2 Cl 4 ).
  • the mass of catalyst present in reactor A is 20.01 g, the PPH (hourly space velocity) of 1.01 h -1 .
  • the hydrogen flow rate is 1.41 / hr (liter per hour).
  • the total pressure is 3 MPa relative.
  • the isomerization reactor A operates at 140 ° C. This temperature makes it possible to optimize the conversion to C5 and C6 by approaching the thermodynamic equilibrium of the reaction.
  • the ratio R A of the number of moles of hydrogen over the number of moles of hydrocarbon at the outlet of reactor A is equal to 0.19.
  • Isomerization reactor B is fed with charge C7 with a flow rate of 66.79 g / h, said feed containing 800 ppm of perchlorethylene.
  • the mass of catalyst present in reactor B is 66.13 g and the PPH is 1.01 h -1 .
  • the hydrogen flow rate is 3.2 l / h.
  • the total pressure is 3 MPa relative.
  • the temperature of the isomerization reaction in reactor B is set at 115 ° C.
  • the ratio R B of the number of moles of hydrogen relative to the number of moles of hydrocarbon at the outlet of reactor B is equal to 0.19.
  • the compositions of the isomerate A and B respectively from reactors A and B and that of the mixture of these two isomerate are shown in Table 3 below.
  • n-paraffins present in the feed For each of the n-paraffins present in the feed is calculated a conversion rate from the composition of the mixture of the two isomerate.
  • Example 2 two different reactors, but catalysts of a different chemical nature, are used as in Example 2: an acidic catalyst (IS 612 A) having a high activity for reactor A and a zeolitic catalyst type Pt / H-beta minus acid but more selective for the isomerization of nC7.
  • Said zeolite is marketed by the company Zeolyst and corresponds to zeolite beta in its protonic form.
  • the isomerization reactor A is fed with the feed C5-C6 at the rate of 20.21 g / h, said feed containing 800 ppm by weight of perchlorethylene (C 2 Cl 4 ).
  • the mass of catalyst present in reactor A is 20.01 g, the PPH is 1.01 h 1 .
  • the hydrogen flow rate is 1.4 l / h.
  • the total pressure is 3 MPa relative.
  • the isomerization reactor A operates at 140 ° C.
  • the ratio R A of the number of moles of hydrogen relative to the number of moles of hydrocarbon at the outlet of reactor A is equal to 0.19.
  • the isomerization reactor B is fed with charge C7 at the rate of 66.79 g / h.
  • the mass of catalyst present in reactor B is 22.26 g, the PPH is 3 h -1 .
  • the hydrogen flow rate is 33.45 l / h.
  • the total pressure is 3 MPa relative.
  • the isomerization reactor B operates at 240 ° C so as to optimize the yield of iso-paraffins.
  • This embodiment of the invention also appears more favorable than the example according to the prior art. Indeed, for a comparable nC7 hydrocarbon conversion, the conversion nC5 and nC6 hydrocarbons are significantly increased as well as the C5 + yield.
  • the present process thus makes it possible to improve the octane numbers of the isomerate compounds, on the one hand by increasing the conversion rates of hydrocarbons containing 5 to 6 carbon atoms, while minimizing the cracking rate of hydrocarbons containing 7 carbon atoms. .

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (6)

  1. Verfahren zur Isomerisierung einer Charge, die Kohlenwasserstoffe umfasst, welche 5 bis 8 Kohlenstoffatome pro Molekül enthalten, wobei :
    - die Charge in mindestens zwei Fraktionen aufgetrennt wird, wobei eine Fraktion A mindestens 80 % an Kohlenwasserstoffen umfasst, die 5 oder 6 Kohlenstoffatome enthalten, und eine Fraktion B mindestens 80 % an Kohlenwasserstoffen umfasst, die 7 oder 8 Kohlenstoffatome umfassen, und die Fraktionen A und B anschließend getrennt voneinander in gesonderten Reaktionsbereichen zur Isomerisierung behandelt werden.
    - wobei die Reaktionsbereiche chemisch verschiedene Isomerisierungskatalysatoren enthalten, wobei die isomerisierende Wirkung des Katalysators, welcher die Fraktion A behandelt, stärker als die isomerisierende Wirkung des Katalysators ist, welcher die Fraktion B behandelt.
    - wobei entweder das Isomerisat, das aus der Isomerisierung der Fraktion B stammt, oder die Mischung der Isomerisate, die aus der Isomerisierung der Fraktionen A und B stammen, in zwei Stoffströme aufgetrennt wird, wobei der erste der Stoffströme den größten Teil des Isopentans und der Paraffine mit mindestens zwei Verzweigungen umfasst und der zweite der Stoffströme den größten Teil der normalen Paraffine und der Paraffine, welche mindestens sechs Kohlenstoffatome und eine einzige Verzweigung enthalten, umfasst.
    - wobei der zweite Stoffstrom zurückgeführt und mit der Charge oder mit der Fraktion B gemischt wird, und
    - wobei mindestens eine der Isomerisierungsreaktionen in Gegenwart eines Überschusses an Wasserstoff durchgeführt wird, sodass das Verhältnis R der Molanzahl an Wasserstoff zur Molanzahl an Kohlenwasserstoffen, die mindestens einem Reaktionsbereich entströmen, im Bereich von 0,06 bis 0,3 liegt, und
    - mindestens eine der Isomerisierungsreaktionen in Gegenwart eines Überschusses an Wasserstoff durchgeführt wird, sodass das Verhältnis R im Bereich von 0,3 bis 30 liegt und größer als 0,3 ist.
  2. Verfahren nach Anspruch 1, wobei das Isomerisat B, das aus der Isomerisierung der Fraktion B stammt, in zwei Stoffströme aufgetrennt wird und der erste Stoffstrom mit dem Isomerisat gemischt wird, welches aus der Isomerisierung der Fraktion A stammt.
  3. Verfahren nach Anspruch 2, wobei darüber hinaus das Isomerisat A, welches aus der Isomerisierung der Fraktion stammt, in zwei Stoffströme aufgetrennt wird, wobei der erste der Stoffströme den größten Teil des Isopentans und der Paraffine mit mindestens einer Verzweigung umfasst, wobei der zweite der Stoffströme den größten Teil der normalen Paraffine umfasst, wobei der zweite Stoffstrom zurückgeführt und mit der Charge oder mit der Fraktion A gemischt wird.
  4. Verfahren nach Anspruch 3, wobei der erste Stoffstrom, der aus dem Isomerisat B stammt, und der erste Stoffstrom, der aus dem Isomerisat A stammt, gemischt werden.
  5. Verfahren nach einem der Ansprüche 1 bis 7, wobei der oder die Isomerisierungskatalysatoren der Gruppe angehören, die geträgerte Katalysatoren, welche mindestens ein Halogen und mindestens ein Metall der Gruppe VIII enthalten, Zeolithkatalysatoren, welche mindestens ein Metall der Gruppe VIII enthalten, Friedel-Crafts-Katalysatoren, Supersäure-Katalysatoren der Typen HPA auf Zirkoniumdioxid, WOx auf Zirkoniumdioxid, sowie sulfatierte Zirkoniumdioxide umfasst.
  6. Verfahren nach einem der Ansprüche 1 bis 8, wobei der Gesamtdruck in den Reaktionsbereichen zur Isomerisierung Relativwerte von ungefähr 0,1 bis 10 MPa annimmt, wobei der Volumengeschwindigkeit pro Stunde ungefähr 0,2 bis 10 h-1 beträgt.
EP02767555A 2001-08-06 2002-07-08 Verfahren zur isomerisierung von c5-c8 kohlenwasserstofffreaktionen mit zwei parallelreaktoren Expired - Lifetime EP1417283B1 (de)

Applications Claiming Priority (3)

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FR0110566 2001-08-06
FR0110566A FR2828205B1 (fr) 2001-08-06 2001-08-06 Procede d'isomerisation d'une coupe c5-c8 mettant en oeuvre deux reacteurs en parallele
PCT/FR2002/002385 WO2003014265A1 (fr) 2001-08-06 2002-07-08 Procede d'isomerisation d'une coupe c5-c8 mettant en oeuvre deux reacteurs en parallele

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EP1417283B1 true EP1417283B1 (de) 2011-04-20

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US (1) US7429685B2 (de)
EP (1) EP1417283B1 (de)
DE (1) DE60239808D1 (de)
FR (1) FR2828205B1 (de)
WO (1) WO2003014265A1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2857371B1 (fr) * 2003-07-11 2007-08-24 Inst Francais Du Petrole Procede ameliore d'isomerisation d'une coupe c7 avec ouverture des cycles naphteniques
MY150403A (en) * 2007-01-15 2014-01-15 Nippon Oil Corp Processes for production of liquid fuel
JP4861838B2 (ja) * 2007-01-15 2012-01-25 Ｊｘ日鉱日石エネルギー株式会社 液体燃料の製造方法
KR100964227B1 (ko) * 2008-05-06 2010-06-17 삼성모바일디스플레이주식회사 평판 표시 장치용 박막 트랜지스터 어레이 기판, 이를포함하는 유기 발광 표시 장치, 및 이들의 제조 방법
US8808534B2 (en) * 2011-07-27 2014-08-19 Saudi Arabian Oil Company Process development by parallel operation of paraffin isomerization unit with reformer
FR3020374B1 (fr) * 2014-04-29 2017-10-27 Axens Procede de production d'essence comprenant une etape d'isomerisation suivie d'au moins deux etapes de separation.
US20160311732A1 (en) * 2015-04-27 2016-10-27 Uop Llc Processes and apparatuses for isomerizing hydrocarbons
US10106476B1 (en) * 2017-03-31 2018-10-23 David Norbert Kockler Energy efficient methods for isomerization of a C5-C7 fraction with dividing wall fractional distillation
FR3068966B1 (fr) * 2017-07-12 2019-06-28 IFP Energies Nouvelles Nouveau schema de production de benzene a partir de reformat sans colonne de toluene
US10118875B1 (en) * 2017-09-13 2018-11-06 David Norbert Kockler Energy efficient methods for isomerization of a C5-C6 fraction with dividing wall fractional distillation

Family Cites Families (6)

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US2399765A (en) * 1943-09-18 1946-05-07 Standard Oil Co Isomerization of light naphtha paraffinic hydrocarbons
US2434437A (en) * 1944-03-15 1948-01-13 Shell Dev Process for isomerization of paraffin hydrocarbons with fluid friedel-crafts catalyst and added dicyclic naphthenic hydrocarbons
US2944959A (en) * 1958-02-26 1960-07-12 Gulf Research Development Co Process for upgrading a wide range gasoline
US3619408A (en) * 1969-09-19 1971-11-09 Phillips Petroleum Co Hydroisomerization of motor fuel stocks
GB8619784D0 (en) * 1986-08-14 1986-09-24 Shell Int Research Isomerization of unbranched hydrocarbons
US5994607A (en) * 1996-02-05 1999-11-30 Institut Francais Du Petrole Paraffin isomerization process comprising fractionation having at least two draw-off levels associated with at least two isomerization zones

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Publication number Publication date
WO2003014265A1 (fr) 2003-02-20
US20040254415A1 (en) 2004-12-16
FR2828205B1 (fr) 2004-07-30
FR2828205A1 (fr) 2003-02-07
US7429685B2 (en) 2008-09-30
DE60239808D1 (de) 2011-06-01
EP1417283A1 (de) 2004-05-12

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