EP0524047B1 - Procédé d'isomérisation de paraffines normales en c5/c6 avec recyclage de paraffines normales - Google Patents

Procédé d'isomérisation de paraffines normales en c5/c6 avec recyclage de paraffines normales Download PDF

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Publication number
EP0524047B1
EP0524047B1 EP92401894A EP92401894A EP0524047B1 EP 0524047 B1 EP0524047 B1 EP 0524047B1 EP 92401894 A EP92401894 A EP 92401894A EP 92401894 A EP92401894 A EP 92401894A EP 0524047 B1 EP0524047 B1 EP 0524047B1
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EP
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Prior art keywords
stage
isomerization
deisopentanization
paraffins
distillate
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EP92401894A
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German (de)
English (en)
French (fr)
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EP0524047A1 (fr
Inventor
Ari Minkkinen
Larry Mank
Sopie Jullian
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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
    • C10G61/00—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen
    • C10G61/02—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen plural serial stages only
    • C10G61/06—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen plural serial stages only the refining step being a sorption process
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline

Definitions

  • the invention relates to a process for the isomerization of n-paraffins into isoparaffins, the aim of which is in particular to improve the octane number of certain petroleum fractions, more particularly those which contain pentanes and normal hexanes as well as pentanes and branched hexanes (cuts C5 / C6).
  • a well-known isomerization process using molecular sieves for the vapor phase separation of unconverted n-paraffins, incorporates the adsorption step by molecular sieve into the reaction step.
  • This is the so-called “Total Isomerization Process” (or “TIP”) described for example in patent US-A-4210771. It combines the implementation of an isomerization reactor fed by the mixture of the feedstock, a desorption effluent and hydrogen, and the implementation of a separation section by adsorption of n-paraffins on molecular sieve, desorption being effected by hydrogen stripping.
  • the reaction system cannot consist of a step with high activity chlorinated alumina, because of the risks of contamination by hydrochloric acid of the integrated molecular sieves.
  • a less efficient catalytic system is then used, based on a zeolite that does not use chlorine. The result is a product with an octane number 1 to 2 points lower than that which would have been obtained with a catalyst based on chlorinated alumina.
  • the catalyst based on chlorinated alumina impregnated with platinum makes it possible to carry out the isomerization reaction at a lower temperature than the catalysts of non-chlorinated zeolite type, which are more stable.
  • the feedstocks are dried in pretreatment operations using molecular sieves.
  • the object of the invention is to propose a new process making it possible to increase as much as possible the octane number of an oil cut containing normal paraffins while limiting the energy expenditure.
  • the present invention makes it possible in particular to overcome the drawbacks of known processes, by combining the high activity system using for example a catalyst consisting of a chlorinated alumina impregnated with platinum with an original adsorption-desorption system on molecular sieve in the vapor phase (system not integrated).
  • a catalyst consisting of a chlorinated alumina impregnated with platinum
  • an original adsorption-desorption system on molecular sieve in the vapor phase system not integrated
  • the desorption of n-paraffins is carried out under advantageous conditions from the energy point of view by combining a pressure reduction and a stripping operation using a vapor rich in isopentane.
  • the judicious use of the isopentane provided by the desisopentanization in the desorption step makes it possible to omit a purging step at the end of it.
  • the adsorbent column then filled with isopentane can be immediately reused for adsorption, the adsorption effluent then not containing n-paraffins, even at the start of the latter. This leads to a significant simplification of the unit, in particular allowing the use of a system containing only two adsorbent beds, each operating alternately in adsorption and in desorption.
  • a system for recompressing the top vapors of the deisopentanizer heat pump
  • the compressor of the heat pump can also serve as a motive power to recirculate the fraction of the overhead stream rich in isopentane necessary for the desorption of the molecular sieve.
  • isomerization of a charge of light naphtha containing a predominant proportion of C5 and C6 hydrocarbons is described as an isomerate with a high octane number.
  • the method of the invention mainly comprises a step (1) of desisopentanization, a step (2) of isomerization, a step (3) of adsorption and a step (4) of desorption.
  • step (1) a column of desisopentanization is fed by means of a wet charge of light naphtha C5 / C6 by line 1 and, by line 11, by means of the effluent from step ( 4) desorption which will be described later, for example, at a pressure of 1 to 2 bars (absolute pressure).
  • the deisopentanization column generally consists of a distillation column comprising fractionation internals (structured packing or trays).
  • the deisopentanization operation separates the charge into a distillate rich in isopentane, containing for example 5 to 20% by moles of n-pentane and in a residue poor in isopentane, containing for example 5 to 15% by moles of isopentane .
  • the charge Before being introduced into the deisopentanization column, the charge can be preheated, for example to a temperature of 30 to 60 ° C., optionally by heat exchange with the isomerate resulting from the adsorption step (3), in the E1 exchanger.
  • the deisopentanization column generally operates between a bottom temperature of 40 to 90 ° C and a head temperature of 20 to 60 ° C.
  • the hot residue from the desisopentanization leaving via line 3 is then sent to the isomerization reactor.
  • the overhead vapors (distillate) leaving via line 2 are generally compressed in a compressor (heat pump) at a sufficient pressure (5 to 6 bars) so that they condense at a temperature higher than 10 to 25 ° C at the temperature required for bottom reboiling column.
  • the condensation of these vapors can then be used to supply the energy necessary for the reboiler through the exchanger E2, avoiding an external energy supply. Much of the condensation takes place in this way, which saves on the cooling means necessary for total condensation of the reflux and distillate.
  • the condensate is partially recycled at the top of the desisopentanizer (reflux) and partly sent by pumping and after vaporization to the adsorption step (3), via line 7.
  • step (2) the residue from line 3 of the desisopentanization step (1) is sent to an isomerization zone I, by pumping the isomerization reaction, for example from 5 at 30 bars.
  • the isomerization reaction is carried out at a temperature of 140 to 300 ° C in the presence of hydrogen.
  • the residue to be treated is mixed with an addition of hydrogen and optionally with a recycling of hydrogen arriving via line 5, then is heated for example to a temperature of 140 to 300 ° C. by means of a charge / heat exchange. effluent, in the exchanger E3 and a final heating in an oven H.
  • the isomerization reaction is preferably carried out on a high activity catalyst, such as for example a catalyst based on chlorinated alumina and platinum, operating at low temperature, for example between 130 and 220 ° C, at high pressure, by example from 20 to 35 bars, and with a low hydrogen / hydrocarbon molar ratio, for example between 0.1 / 1 and 1/1.
  • a high activity catalyst such as for example a catalyst based on chlorinated alumina and platinum, operating at low temperature, for example between 130 and 220 ° C, at high pressure, by example from 20 to 35 bars, and with a low hydrogen / hydrocarbon molar ratio, for example between 0.1 / 1 and 1/1.
  • Known catalysts which can be used consist for example of a support of ⁇ and / or ⁇ alumina of high purity containing from 2 to 10% by weight of chlorine, from 0.1 to 0.35% by weight of platinum and optionally other metals. They can be implemented with a space speed of 0.5 to 10 h -1,
  • a well known catalyst consists of a mordenite with an SiO2 / Al2O3 ratio of between 10 and 40, preferably between 15 and 25 and containing from 0.2 to 0.4% by weight of platinum.
  • the catalysts belonging to this family are less advantageous than those based on chlorinated alumina because they operate at higher temperature (240 to 300 ° C.) and lead to less extensive conversion of normal paraffins to high octane isoparaffins.
  • n-paraffins are transformed into isoparaffins; however, there remains in the effluent leaving the isomerization reactor via line 4 a large proportion of n-paraffins, which can range up to around 30 mol% and which is preferably between 15 and 25 mol% .
  • the effluent from the isomerization step (2) after cooling, can pass through a separator S1, the vapor of which is recycled by line 5 at the inlet of the isomerization reactor I and the liquid effluent (isomerate) leaving via line 6 is vaporized in the exchanger E4 before being sent to the adsorption step (3).
  • this isomerate is mixed with a flow consisting of the part of the condensate resulting from the condensation of the distillate from step (1) of desisopentanization which has not been recycled into head of the desisopentanizer, this stream being vaporized for example by heat exchange in the exchanger E5 with the vapor effluent from the adsorber A, which for its part is at least partially condensed; this flow arrives via line 7.
  • the vapor mixture thus formed is passed through in ascending current through the adsorber A, in which the n-paraffins are retained.
  • the isomerate freed from the n-paraffins leaves via line 9 can be at least partially condensed in the exchanger E5 then in the exchanger E1. It can still be cooled in the exchanger E6.
  • the adsorbent bed generally consists of a molecular sieve based on a zeolite capable of selectively adsorbing n-paraffins, and having an apparent pore diameter close to 5 ⁇ ; 5 A zeolite is perfectly suited for this use: its pore diameter is close to 5 ⁇ and its adsorption capacity for n-paraffins is high.
  • adsorbents such as chabazite or erionite can be used.
  • the preferred operating conditions are a temperature of 200 to 400 ° C and a pressure of 10 to 40 bar.
  • the adsorption cycle generally lasts from 2 to 10 minutes.
  • the effluent collected at the outlet of the adsorber A by line 9 contains practically only isoparaffins (isopentane and isohexane). It is condensed, for example by heat exchange, as already mentioned above. Still cooled, for example by heat exchange with the load supplying the step (1) of deisopentanization, it constitutes the final product (isomerate) of the process of the invention.
  • n-paraffins adsorbed during step (3) are then desorbed in the desorption step (4) represented in FIG. 2 by the adsorber D, which is none other than the absorber A saturated with n -paraffins and working in desorption.
  • the operation is carried out by lowering the pressure to a value less than 5 bars, preferably less than 3 bars, and by stripping by means of a gas flow rich in isopentane, for example withdrawn at a level of suitable pressure of the compressor of the heat pump P1 brought by line 10 to pass through the adsorber D in downdraft.
  • This gas flow is generally brought to a temperature of 250 to 350 ° C in the exchanger E7.
  • the proportion of isopentane-rich flux necessary for desorption advantageously corresponds to 1 to 2 moles of isopentane per mole of n-paraffins to be desorbed.
  • the operation generally lasts from 2 to 10 minutes.
  • the effluent from the desorption step (4) is recycled to the desisopentanization step via line 11; it is introduced into the deisopentanization column at a level lower than that of the supply of fresh feed or in admixture with the latter.
  • the adsorber D after desorption, is again used in adsorption.
  • a isomerization effluent stabilization step intended essentially to remove hydrochloric acid from the catalyst at the same time as hydrogen and light hydrocarbons from C1 to C4.
  • the isomerization reactor effluent consisting of a two-phase mixture is sent by line 4 directly to a stabilization column S2 generally operating at a pressure of 10 to 20 bars, advantageously around 15 bars.
  • the stabilizer S2 is shown schematically in Figure 3.
  • the stabilizer at the top eliminates the lightest products as well as any excess hydrogen which leaves via line 12.
  • the distillate is partially condensed by cooling with water in the exchanger E8, the condensate obtained being able to be at least partially recycled to the stabilizer head via line 13, pump P4 and line 14. If desired, an LPG can also be collected as a net distillate, via line 15.
  • the hydrochloric acid possibly present (when the isomerization catalyst is based on chlorinated alumina impregnated with platinum) is sufficiently volatile to pass entirely at the head of the stabilizer and is evacuated with the gaseous products via line 12.
  • the product of bottom of the stabilizer, free of hydrochloric acid, is drawn off through line 6 in the form of a vapor flow at the pressure of the stabilizer and is sent to the adsorber after additional heating in the exchanger E4.
  • the stabilizer reboiler thus serves to vaporize the charge of the adsorber A, at a temperature of about 150 to 200 ° C., allowing the latter to be supplied in the vapor phase.
  • the stabilizer S2 shown in FIG. 3 is supplied with the bottom liquid from the separator S1 via line 6.
  • the process of the invention makes it possible to obtain, from fillers of light naphthas rich in C5 / C6 having a Research Octane Index (IOR) of 65 to 75, an isomerate having an IOR of 87 to 91.
  • IOR Research Octane Index
  • the load F is constituted by a light naphtha previously desulphurized, having the following molar composition: Component % Molar Isobutane (iC4) 0.4 Normalbutane (nC4) 2.4 Isopentane (iC5) 21 Normalpentane (nC5) 29 Cyclopentane (CP) 2.2 2-2 dimethylbutane (22 DMB) 0.5 2-3 dimethylbutane (23 DMB) 0.9 2 methylpentane (2 MP) 12.7 3 methylpentane (3 MP) 10 Normal hexane (nC6) 14 Methylcyclopentane (MCP) 5 Cyclohexane (CH) 0.5 Benzene 1.3 C7 + 0.1
  • the liquid charge is introduced via line 1 into the distillation column DI with a flow rate of 77.6 kg / h. Simultaneously, there is injected into this column, at an average flow rate of 46.8 kg / h, a recycling stream originating from the desorption zone D via line 11.
  • the column filled with a structured packing having an efficiency of approximately 40 theoretical stages, operates under a top pressure of 2 bars with a reflux rate of 6 relative to the net distillate.
  • the reflux flask is equipped with a decanter making it possible to evacuate an aqueous phase at the lowest point.
  • the bottom liquid taken up by a pump is sent via line 3 to the isomerization reactor I after adding hydrogen and preheating to a temperature of 140 ° C. under a pressure of 30 bars.
  • the reactor contains 52 liters of an isomerization catalyst based on alumina ⁇ containing 7% by weight of chlorine and 0.23% by weight of platinum. To maintain the activity of the catalyst, a continuous addition of 42 g / hour of carbon tetrachloride is carried out in the feed, which corresponds to a content of 500 ppm by weight.
  • the isomerization reaction is carried out under an average pressure of 30 bars and at a temperature of 140 ° C. (inlet) to 160 ° C. (outlet). Under these conditions, the hydrocarbon effluent from the isomerization reactor contains approximately 13.9% by mole of nC5 and 4.6% by mole of nC6.
  • the complete effluent from the isomerization reactor is sent directly by line 4 to the stabilization column S2 ( Figure 3) operating under a pressure of 15.5 bars, with a temperature of around 200 ° C at the reboiler and a temperature from 30 ° C to the reflux flask.
  • a gas mixture essentially containing hydrogen is purged at the top via line 12.
  • the bottom fraction containing less than 0.5 ppm by weight of HCl is drawn off in the vapor phase at the reboiler via line 6.
  • line 9 is recovered, with an average flow rate of approximately 77 Kg / h, an isomer containing less than 1% by moles of normal paraffins in C5 and C6 and having an IOR of 88 to 88 , 5 which constitutes the final product.
  • the adsorbent bed contained in the adsorber D is in the desorption phase. This is carried out by lowering the pressure from 15 bars to 2 bars and injection from the top of the reactor, at a temperature of 300 ° C. and with an average flow rate of 31.8 kg / h, of the rest of the effluent from head of the DI column rich in iC5 (line 10).
  • the temperature of the adsorbent bed is close to 300 ° C. during the whole desorption phase which lasts 6 minutes.
  • the desorption effluent withdrawn at the bottom of the adsorber D contains approximately 27% by moles of nC5 and 7.5% by moles of nC6. It is recycled via line 11 to the distillation column DI.
  • the adsorbers A and D are swapped by means of a set of valves, so as to operate alternately in the adsorption and desorption phase.

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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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP92401894A 1991-07-18 1992-07-02 Procédé d'isomérisation de paraffines normales en c5/c6 avec recyclage de paraffines normales Expired - Lifetime EP0524047B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9109215 1991-07-18
FR9109215A FR2679245B1 (fr) 1991-07-18 1991-07-18 Procede d'isomerisation de paraffines normales en c5/c6 avec recyclage de paraffines normales.

Publications (2)

Publication Number Publication Date
EP0524047A1 EP0524047A1 (fr) 1993-01-20
EP0524047B1 true EP0524047B1 (fr) 1995-10-04

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EP92401894A Expired - Lifetime EP0524047B1 (fr) 1991-07-18 1992-07-02 Procédé d'isomérisation de paraffines normales en c5/c6 avec recyclage de paraffines normales

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US (1) US5233120A (ja)
EP (1) EP0524047B1 (ja)
JP (1) JP3358028B2 (ja)
CA (1) CA2074140C (ja)
DE (1) DE69205231T2 (ja)
ES (1) ES2080464T3 (ja)
FR (1) FR2679245B1 (ja)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5530172A (en) * 1994-11-03 1996-06-25 Uop Process for alkane isomerization using reactive chromatography
US5530173A (en) * 1994-11-03 1996-06-25 Funk; Gregory A. Process for alkane isomerization using reactive chromatography and reactive desorbent
FR2771419B1 (fr) * 1997-11-25 1999-12-31 Inst Francais Du Petrole Essences a haut indice d'octane et leur production par un procede associant hydro-isomerisation et separation
JP4556928B2 (ja) * 1999-06-01 2010-10-06 日産自動車株式会社 内燃機関
JP4490533B2 (ja) * 1999-12-17 2010-06-30 出光興産株式会社 燃料電池用燃料油
US8692046B2 (en) 2011-01-13 2014-04-08 Uop Llc Process for isomerizing a feed stream including one or more C4-C6 hydrocarbons
US8716544B2 (en) * 2011-01-13 2014-05-06 Uop Llc Process for isomerizing a feed stream including one or more C4-C6 hydrocarbons
US9663721B2 (en) 2014-09-04 2017-05-30 Uop Llc Heat recovery from a naphtha fractionation column
CN104945212B (zh) * 2015-06-03 2017-01-11 上海河图工程股份有限公司 一种c5/c6烷烃低温异构化方法
US20180215683A1 (en) * 2017-01-27 2018-08-02 Saudi Arabian Oil Company Isomerization process using feedstock containing dissolved hydrogen

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2834823A (en) * 1955-03-07 1958-05-13 Kellogg M W Co Isomerization of hydrocarbons
US2966528A (en) * 1957-11-08 1960-12-27 Universal Oil Prod Co Combination process of isomerization and a sorption process followed by selective frationation
US2918511A (en) * 1958-05-09 1959-12-22 Texaco Inc Isomerizing a c6 hydrocarbon fraction
GB876730A (en) * 1958-08-04 1961-09-06 Universal Oil Prod Co Production of branched-chain aliphatic hydrocarbons
US3150205A (en) * 1960-09-07 1964-09-22 Standard Oil Co Paraffin isomerization process
US4210771A (en) * 1978-11-02 1980-07-01 Union Carbide Corporation Total isomerization process
US5043525A (en) * 1990-07-30 1991-08-27 Uop Paraffin isomerization and liquid phase adsorptive product separation

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Publication number Publication date
CA2074140A1 (fr) 1993-01-19
EP0524047A1 (fr) 1993-01-20
JPH05202368A (ja) 1993-08-10
CA2074140C (fr) 2005-09-13
ES2080464T3 (es) 1996-02-01
FR2679245B1 (fr) 1993-11-05
US5233120A (en) 1993-08-03
DE69205231T2 (de) 1996-03-14
JP3358028B2 (ja) 2002-12-16
DE69205231D1 (de) 1995-11-09
FR2679245A1 (fr) 1993-01-22

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