EP1640436B1 - Verfahren zur Isomerisierung von einer C7-Fraktion mit Koproduktion von einer cyclischen Methylcyclohexan-reichen Fraktion - Google Patents

Verfahren zur Isomerisierung von einer C7-Fraktion mit Koproduktion von einer cyclischen Methylcyclohexan-reichen Fraktion Download PDF

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EP1640436B1
EP1640436B1 EP05291856A EP05291856A EP1640436B1 EP 1640436 B1 EP1640436 B1 EP 1640436B1 EP 05291856 A EP05291856 A EP 05291856A EP 05291856 A EP05291856 A EP 05291856A EP 1640436 B1 EP1640436 B1 EP 1640436B1
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paraffins
unit
distillation column
isomerization
hand
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French (fr)
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EP1640436A1 (de
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Paul Broutin
Dominique Casanave
Jean-Francois Joly
Elsa Jolimaitre
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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
    • C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/06—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including a sorption process as the refining step in the absence of hydrogen
    • 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 product of the isomerization (or isomerate) is free of aromatic compounds in contrast to the reformate which usually contains a significant amount due to dehydrocyclization reactions of paraffins and dehydrogenation of naphthenes.
  • Isomerate and reformate are usually sent to the gasoline pool in which other bases such as gasoline resulting from fluidized catalytic cracking (FCC) or additives such as methyl tertiary butyl ether (MTBE) can also be used.
  • FCC fluidized catalytic cracking
  • MTBE methyl tertiary butyl ether
  • Aromatics have high octane ratings for use in spark ignition engines, but for environmental reasons, their total content in gasoline is becoming increasingly limited.
  • the present invention relates more particularly to the isomerization of the C 7 -rich fraction obtained from atmospheric distillation naphtha
  • Table 1 gives the research octane number (RON) and the boiling points of the main hydrocarbon compounds present in the C7 cut obtained from atmospheric distillation naphtha: Table 1 RON teb (° C) trimethyl 2-2-3 butane 112.1 80.8 dimethyl 2-2 pentane 92.8 79.2 dimethyl 2-4 pentane 83.1 80.5 dimethyl 3-3 pentane 80.8 86 dimethyl 2-3 pentane 91.1 89.7 2-methyl hexane 42.4 90 3-methyl hexane 52 91.9 ethyl-3 pentane 65 93.4 n-heptane 0 98.4 1,1-dimethylcyclopentane 92.3 87.8 cis-dimethyl-1,3 cyclopentane 79.2 90.8 1,3-trans-1,3-dimethylcyclopentane 80.6 91.7 1,2-trans-1,2-dimethylcyclopentane 80.6 91.8 methyl-cyclohexane 74.8 100.9 e
  • isomers with only one branch or mono-branched have insufficient octane numbers (42 for 2-methylhexane, 52 for 3-methylhexane) to be mixed with the gasoline pool.
  • nC7 in the isomerate Up to 1 wt.% Of nC7 in the isomerate and, if possible, less than 0.5 wt.% Can be tolerated.
  • the toluene present in the fresh feedstock can be totally hydrogenated to methylcyclohexane (MCH), either in a specific hydrogenation unit, or in the paraffin isomerization unit.
  • MCH methylcyclohexane
  • the C 7 isomerate obtained may contain up to 30% by weight of methyl-cyclohexane, a compound whose RON is less than 75, which significantly increases the RON of the C 7 isomerate. got.
  • MCH methylcyclohexane
  • the MCH can then be used either as a solvent or possibly reintroduced into the gasoline pool within the limits allowed by its relatively low RON.
  • the problem that the present invention seeks to solve is that of the production of gasoline bases from a C 7 fraction which have a search octane number (RON) of at least 80, with a content limited aromatic compounds, which makes it possible to anticipate the new regulations on the specifications of the gasoline pool.
  • RON search octane number
  • US Patent 6,338,791 discloses a separation process coupled to an isomerization reactor.
  • the separation process makes it possible to produce a fraction rich in multibranched paraffins and possibly in saturated or unsaturated cyclic compounds. This method therefore makes it possible to produce only one cut because the naphthenes and aromatics of the feedstock are not separated from the paraffins, and are therefore injected into the isomerization reactor.
  • the present invention must be placed in the more general context of the treatment of the naphtha fraction resulting from the atmospheric distillation of the crude.
  • FIG. 1 represents the process diagram according to the invention in its preferred variant comprising, upstream of the distillation column, a hydrogenation unit of toluene, and on the overhead flow coming from the distillation column, a paraffin separation unit. mono and di-connected.
  • the toluene hydrogenation unit and the mono and di paraffin separation unit connected to the overhead stream are optional and are shown in dotted line in FIG.
  • the fresh feedstock (1) is introduced into a distillation column (CD) from which a) a head stream (3) which gives the isomerized product is extracted, b) a side stream (4) which feeds one of the isomerisation units (IS) into a mixture and c) a bottom stream (5) which is introduced into a separation unit (SP1) of the normal paraffins on the one hand, and cyclic molecules of on the other hand, especially methylcyclohexane.
  • CD distillation column
  • SP1 separation unit
  • the flow (7) representing the effluent of the separation unit (SP1) consists of at least 90% mass of saturated or unsaturated cyclic molecules.
  • the stream (6) consisting of a majority of normal paraffins is reintroduced in admixture with the side stream (4) to constitute the stream (11) at the inlet of the isomerization unit (IS).
  • the effluent (8) of the isomerization unit (IS) is sent to a stabilization column (ST), from which a flow (9) is discharged which is sent back to the distillation column (CD) Ce flow (9) is reintroduced into the column (CD) on a tray located above the side draw plate so as to create a depletion of the normal paraffins whose content in the top flow (3) of the column (CD) will generally be less than 1% by weight and preferably less than 0.5% by weight.
  • the flow (10) leaving the top of the stabilization column constitutes a gaseous fraction which is sent to the fuel poool of the refinery.
  • the top stream (3) of the distillation column (CD) constitutes the isomerate.
  • the top stream (3) of the distillation column (CD) can be sent to a separation unit ( SP2) normal and mono-branched paraffins on the one hand, and branched di- and tri-paraffins on the other hand, the normal and mono-branched paraffins being reintroduced into the isomerization unit (IS).
  • SP2 a separation unit
  • the normal and mono-branched paraffins being reintroduced into the isomerization unit (IS).
  • the isomerate is constituted by the flow (12).
  • the fresh feedstock (1) may be introduced upstream of the distillation column (CD) in a toluene hydrogenation unit (HG) which makes it possible to convert the latter to methylcyclohexane.
  • the effluent of this hydrogenation unit constitutes the stream (2) and is sent as feed for the distillation column (CD).
  • the distillation column may be of the internal wall column type.
  • This type of column allows the fractionation by distillation of a feedstock in three distinct cuts, with a gain in energy required for the separation of about 20 - 30% relative to to a conventional distillation column.
  • the method which is the subject of the present invention thus comprises at least one distillation column (CD), at least one separation unit (SP1) of normal paraffins and cyclic molecules (methylcyclohexane and optionally toluene) making it possible to send to the isomerization unit (IS) that the paraffinic fraction of the C7 cut, and at least one isomerization unit (IS) fed by the lateral flow of the distillation column (CD) and by the normal paraffins from the unit separation (SP1).
  • CD distillation column
  • SP1 separation unit of normal paraffins and cyclic molecules (methylcyclohexane and optionally toluene)
  • the separation unit (SP1) between n-heptane and the cyclic molecules may use any technique known to those skilled in the art.
  • PSA pressure swing adsorption process
  • CCS simulated countercurrent separation
  • any adsorbent or adsorbent mixture having a selectivity in favor of the normal heptane or in favor of the cyclic molecules may be used, in particular an LTA-type zeolite. which selectively adsorbs normal paraffins and excludes molecules of larger molecular diameter, such as cyclic molecules saturated or not.
  • the adsorption separation (SP1) can be carried out in the gas phase by a PSA type process.
  • the operating temperature of the unit is between 150 and 400 ° C.
  • the desorbent used may be an inert gas, such as hydrogen or nitrogen or a hydrocarbon, such as C3-C6 paraffins.
  • Desorbents particularly well suited for this separation are normal paraffins.
  • One of the preferred desorbents is normal butane, whose boiling point is very far from that of nC7, and which can therefore be easily separated from this molecule.
  • Hydrogen is also a desorbent particularly well suited for this separation, since it can be directly recycled to the isomerization reactor with the desorbate (effluent from the desorption unit rich in nC7).
  • Such a separation unit makes it possible to produce MCH or an MCH + toluene mixture with a purity of between 95 and 99% by mass, and a yield of between 50 and 95%.
  • the adsorption separation (SP1) can be carried out in the liquid phase by a CCS type process.
  • the operating temperature of the unit is between 100 and 250 ° C.
  • the pressure of the column during the adsorption phase is between 2 and 20 bar.
  • the desorbent used is preferably a hydrocarbon, and may be in particular C3-C6 paraffins.
  • Desorbents particularly suitable for this separation are normal paraffins.
  • Such a CCS separation unit makes it possible to produce MCH or a MCH + toluene mixture with a purity of between 95 and 99.5% by mass, and a yield of between 50 and 98%.
  • the said separation (SP1) can also be carried out using one or more membrane modules.
  • Silicalite membranes such as those described in U.S. Patent 5,871,165 are known to possess a form selectivity in favor of normal paraffins.
  • the process also comprises at least one isomerization unit (IS) for converting normal and mono branched paraffins into multi-branched paraffins, such as the unit described in FIG. patent FR 01/10566 .
  • the isomerization catalyst used in said unit will be included in the group consisting of supported catalysts containing at least one halogen and at least one Group VIII metal, zeolitic catalysts containing at least one Group VIII metal, Friedel catalysts and Crafts, super acidic catalysts of type HPA on zirconia, WOx on zirconia, or sulphated zirconia.
  • the total pressure in the isomerization reaction zone is about 10 to 50 barg, the hourly space velocity being about 0.2 to 10 h -1.
  • the hydrogen / hydrocarbon molar ratio is between 0.06 and 30 mol / mol.
  • the temperature in the reaction zone is between 50 and 150 ° C, and preferably between 60 and 100 ° C.
  • the process optionally comprises a separating unit (SP2) fed by the column top flow (CD) and making it possible to separate the normal and mono branched paraffins on the one hand and the multi-branched paraffins on the other hand, so as to to recycle normal and mono-branched paraffins to the isomerization unit and maximize the production of multi-branched paraffins.
  • SP2 separating unit
  • CD column top flow
  • SP2 separation process
  • mono-branched paraffins and multi-branched paraffins can be based on any technique known to those skilled in the art.
  • a separation by distillation can be used, based on the difference in boiling temperatures of these different compounds (see Table 1).
  • the adsorbent used in said unit may be any adsorbent known to those skilled in the art to make this separation, for example the adsorbents described in the US Patents 6,353,144 , FR 02/09841 and the patent application US20020045793 Alcited above.
  • SP2 separation process of normal and mono-branched paraffins and multi-branched paraffins can also be based on a coupling of different techniques.
  • the separation is partially carried out by distillation to produce an intermediate feed enriched in di-branched paraffins and depleted in mono-branched paraffins.
  • This intermediate charge is then treated in an adsorption separation unit to obtain the desired final purity of di-branched paraffins.
  • the process which is the subject of the present invention may also comprise a unit for hydrogenation of toluene (HG) contained in the feed so as to convert this toluene to methylcyclohexane.
  • HG toluene
  • the hydrogenation catalyst used in said unit is a supported catalyst containing at least one Group VIII metal.
  • the total pressure in the reaction zone may be between 2 and 70 bar relative, and preferably between 5 and 50 bar relative.
  • the hydrogen / hydrocarbon molar ratio is between 1 and 15 mol / mol.
  • the temperature in the reaction zone is between 50 and 300 ° C, and preferably between 100 and 200 ° C.
  • the hourly volume velocity will be between 2 and 20 h-1.
  • This example illustrates one of the preferred variants of the invention in which the feed to be treated (1) is introduced into a hydrogenation reactor specific for toluene (HG) and then in a distillation column (CD) with 88 actual trays. The charge is introduced at the level of the tray 50.
  • HG toluene
  • CD distillation column
  • the lateral flow is extracted from the column at the plateau 44 and the recycling of the isomerization effluents (IS) after the stabilization (ST) is carried out at the plateau 15.
  • the fresh batch (1) has in the example considered the following composition (in% weight): dimethyl 2-3 butane 0.01 2-methyl pentane 0.13 methyl-3 pentane 0.16 n-hexane 1.41 methyl-cyclopentane 0.63 cyclohexane 1.71 benzene 0.37 trimethyl 2-2-3 butane 0.08 dimethyl 2-2 pentane 0.20 dimethyl 2-3 pentane 3.57 dimethyl 2-4 pentane 0.50 dimethyl 3-3 pentane 0.26 2-methyl hexane 8.97 3-methyl hexane 12.25 ethyl-3 pentane 1.14 n-heptane 31.39 1,1-dimethylcyclopentane 0.82 cis-dimethyl-1,3 cyclopentane 2.29 1,3-trans-1,3-dimethylcyclopentane 2.21 1,2-trans-1,2-dimethylcyclopentane 4.19 methyl-cyclohexane 12.96 ethyl-cyclopentane 0.
  • the separation unit between paraffins and naphthenes produces two effluents; an effluent (6) rich in n-heptane and an effluent (7) rich in methylcyclohexane.
  • the stream (6) is mixed with the stream (4) to give a stream (11) which constitutes the charge of the isomerization unit (IS) which uses a platinum catalyst on chlorinated alumina such as the described in the application US20020002319 A1 .
  • IS isomerization unit
  • the RON of this isomerate (stream 3) is 84.3 and its aromatic content is 0.00% wt.
  • composition of the stream (7) from the adsorption separation unit is as follows in weight percent: dimethyl 2-2 butane 0.01 dimethyl 2-3 butane 0.00 2-methyl pentane 0.0 methyl-3 pentane 0.0 n-hexane 0.0 methyl-cyclopentane 0.00 cyclohexane 0.0 benzene 0.0 trimethyl 2-2-3 butane 0.00 dimethyl 2-2 pentane 0.00 dimethyl 2-3 pentane 0.04 dimethyl 2-4 pentane 0.00 dimethyl 3-3 pentane 0.00 2-methyl hexane 0.15 3-methyl hexane 0.87 ethyl-3 pentane 0.22 n-heptane 1.02 1,1-dimethylcyclopentane 0.0 cis-dimethyl-1,3 cyclopentane 0.03 1,3-trans-1,3-dimethylcyclopentane 0.06 1,2-trans-1,2-dimethylcyclopentane 0.11 methyl-cyclohexane 94.
  • the summary table 3 below provides a comparison of the properties of the flows: ⁇ u> Table 3 ⁇ / u> stream (1) of example 1 flow (3) of Example 1 stream (7) of Example 1 % paraffins 60.56 94.11 2.31 % aromatics 13.09 0.00 0 % naphthenes 25.54 5.89 97.69 RON 50.7 84.3 73.9
  • Example 1 shows that the method of Example 1 according to the invention makes it possible to co-produce from the C7 cut (stream 1) resulting from atmospheric distillation, containing 13% aromatics and very low RON, an effluent (stream 3) very poor in aromatics and RON compatible with use in the gasoline pool and a naphthenic cut (stream 7) of high purity, recoverable as a solvent.
  • Example 1 the process as described in Example 1 (in particular the composition of the fresh feedstock is identical to that of stream (1)) is used, but the fresh feedstock is not treated in the hydrogenation reactor. toluene.
  • the flow composition (3) at the top of the distillation column CD is then the following in weight percentages: dimethyl 2-2 butane 0.09 dimethyl 2-3 butane 0.09 2-methyl pentane 0.51 methyl-3 pentane 0.42 n-hexane 2.40 methyl-cyclopentane 1.49 cyclohexane 3.93 benzene 0.0 trimethyl 2-2-3 butane 7.54 dimethyl 2-2 pentane 25.92 dimethyl 2-3 pentane 0.85 dimethyl 2-4 pentane 47.09 dimethyl 3-3 pentane 2.78 2-methyl hexane 4.19 3-methyl hexane 1.75 ethyl-3 pentane 0.07 n-heptane 0.5 1,1-dimethylcyclopentane 0.11 cis-dimethyl-1,3 cyclopentane 0.04 1,3-trans-1,3-dimethylcyclopentane 0.04 1,2-trans-1,2-dimethylcyclopentane 0.03 methyl-cyclohexane
  • composition of the stream (7) from the adsorption separation unit is as follows in percentages weight: dimethyl 2-2 butane 0.0 dimethyl 2-3 butane 0.02 2-methyl pentane 0.0 methyl-3 pentane 0.0 n-hexane 0.0 methyl-cyclopentane 0.00 cyclohexane 0.0 benzene 0.0 trimethyl 2-2-3 butane 0.00 dimethyl 2-2 pentane 0.00 dimethyl 2-3 pentane 0.01 dimethyl 2-4 pentane 0.00 dimethyl 3-3 pentane 0.00 2-methyl hexane 0.04 3-methyl hexane 0.35 ethyl-3 pentane 0.12 n-heptane 0.76 1,1-dimethylcyclopentane 0.0 cis-dimethyl-1,3 cyclopentane 0.03 1,3-trans-1,3-dimethylcyclopentane 0.05 1,2-trans-1,2-dimethylcyclopentane 0.11 methyl-cyclohexane 70.
  • Example 2 shows that the process of Example 2 according to the invention makes it possible to produce a paraffinic cut without aromatics (stream 3) and a cut rich in cyclic molecules (stream 7), both of RON compatible with a use in the gasoline pool. It is therefore possible to recombine the two streams (stream 3 + stream 7) to obtain a depleted cut in aromatics with respect to the feed (stream 1) and RON much higher than 80 which answers the problem of maintaining the specification. in RON with a limited content of aromatics.

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  • Engineering & Computer Science (AREA)
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  • General Chemical & Material Sciences (AREA)
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Claims (7)

  1. Verfahren zur Herstellung eines RON Isomerats, das mindestens gleich 80 ist und zur Koproduktion einer naphthenischen Fraktion, die sich hauptsächlich aus Methylcyclohexan und gegebenenfalls Toluol zusammensetzt, aus einer frischen C7 Kohlenwasserstoffcharge, die Paraffine, Naphthene und aromatische Verbindungen in beliebigen Anteilen enthält, wobei das Verfahren mindestens eine Destillationskolonne, mindestens eine Isomerisierungseinheit und mindestens eine Einheit zur Trennung normaler Paraffine von zyklischen Molekülen, insbesondere Methylcyclohexan, umfasst, dadurch gekennzeichnet, dass das hergestellte Isomerat weniger als 1 Gewichtsprozent aromatische Verbindungen und vorzugsweise weniger als 0,5 Gewichtsprozent aromatische Verbindungen enthält und dadurch, dass die frische Charge in eine Destillationskolonne eingeführt wird, aus der extrahiert wird a) ein oberer Fluss, der das hergestellte Isomerat liefert, b) ein seitlicher Fluss, der eine Isomerisierungseinheit mit Gemisch speist sowie c) ein unterer Fluss, der in eine Einheit zur Trennung normaler Paraffine einerseits und zyklischer Moleküle, insbesondere Methylcyclohexan, andererseits eingeführt wird, wobei die normalen Paraffine im Gemisch mit dem seitlichen Fluss in die Isomerisierungseinheit eingeführt werden und die naphthenische Fraktion mit einem Reinheitsgrad von mindestens 90 Massenprozent hergestellt wird.
  2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass eine der Isomerisierungseinheiten durch die seitliche Entnahme gespeist wird, die aus der Destillationskolonne stammt, wobei der Isomerisierungsausfluss nach Stabilisation auf einer Stufe in die Destillationskolonne zurückgeführt wird, die sich oberhalb der Stufe der seitlichen Entnahme befindet.
  3. Verfahren nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, dass der obere Fluss der Destillationskolonne in eine Einheit zur Trennung normaler und einfach verzweigter Paraffine einerseits sowie doppelt und dreifach verzweigter Paraffine andererseits überführt wird, wobei die normalen und einfach verzweigten Paraffine in die Isomerisierungseinheit zurück geführt werden und die doppelt und dreifach verzweigten Paraffine das Isomerat bilden.
  4. Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass die frische Charge stromaufwärts von der Destillationskolonne in eine Einheit zur Hydrogenierung von Toluol eingeführt wird, die es gestattet, letzteres in Methylcyclohexan umzuwandeln.
  5. Verfahren nach einem der Ansprüche 1 bis 4, wobei die Destillationskolonne vom Typ einer Kolonne mit Innenwand ist.
  6. Verfahren nach einem der Ansprüche 1 bis 5, wobei die Trennung der normalen Paraffine einerseits und der zyklischen Moleküle andererseits durch ein Adsorptionsverfahren erzielt wird.
  7. Verfahren nach einem der Ansprüche 1 bis 5, wobei die Trennung der normalen Paraffine einerseits und der zyklischen Moleküle andererseits durch ein Membranverfahren erzielt wird.
EP05291856A 2004-09-22 2005-09-07 Verfahren zur Isomerisierung von einer C7-Fraktion mit Koproduktion von einer cyclischen Methylcyclohexan-reichen Fraktion Not-in-force EP1640436B1 (de)

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FR0409998A FR2875507B1 (fr) 2004-09-22 2004-09-22 Procede ameliore d'isomerisation d'une coupe c7 avec coproduction d'une coupe riche en molecules cycliques

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DE602005002597T2 (de) 2008-01-31
DE602005002597D1 (de) 2007-11-08
EP1640436A1 (de) 2006-03-29
US7481916B2 (en) 2009-01-27
FR2875507B1 (fr) 2008-10-31
US20060065576A1 (en) 2006-03-30
FR2875507A1 (fr) 2006-03-24

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