EP0354826B1 - Kohlenwasserstoff-Fraktionierungs- und Extraktionsverfahren zur Erlangung von Benzin mit verbesserter Oktanzahl und von Kerosin mit verbessertem Rauchpunkt - Google Patents

Kohlenwasserstoff-Fraktionierungs- und Extraktionsverfahren zur Erlangung von Benzin mit verbesserter Oktanzahl und von Kerosin mit verbessertem Rauchpunkt Download PDF

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EP0354826B1
EP0354826B1 EP89402119A EP89402119A EP0354826B1 EP 0354826 B1 EP0354826 B1 EP 0354826B1 EP 89402119 A EP89402119 A EP 89402119A EP 89402119 A EP89402119 A EP 89402119A EP 0354826 B1 EP0354826 B1 EP 0354826B1
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solvent
petrol
stage
extraction
process according
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French (fr)
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EP0354826A1 (de
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Sigismond Franckowiak
Paul Mikitenko
Pierre Baumgartner
Georges Cohen
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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
    • C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/06—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for spark ignition
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Definitions

  • the invention relates to a process for the fractionation and extraction of hydrocarbons, in particular a process for the production of gasolines with an improved octane number and kerosene with an improved smoke point and optionally a process for the production of gas oil with a cetane number. improved by selective extraction of suitable hydrocarbon cuts.
  • Liquid effluents distilling between about 50 ° C and 130 ° C constitute a gasoline cut with a low octane number due to a majority of saturated hydrocarbons and to this cut can be added at least partially a cut of heavy gasoline 130 -220 ° C richer in aromatic hydrocarbons and interesting by its high octane number.
  • This solution is even fully adopted in summer, some of the heavy petrol being used for aviation petrol. However, during the winter, the majority of heavy gasoline is mixed with the diesel cut to meet heating needs.
  • patent FR 1424225 teaches the extraction of aromatic and non-aromatic constituents of recycling oil ((LCO) or light cycle oil) constituted by a distillation fraction of 204 to 316 ° C produced approximately by the catalytic cracking of oil in two successive zones.
  • LCO recycling oil
  • a mixture of dimethylformamide and approximately for example 10% of water is used as solvent for the aromatics while in the second one uses a mixture of naphtha rich in saturated hydrocarbons and xylene to extract a mixture containing the hydrocarbons aromatics and recycle the solvent to the first extraction zone.
  • the mixture thus extracted is then passed through a distillation column. At the bottom, a concentrate of aromatic hydrocarbons is collected and at the top, at least part of the naphtha is recovered, which is recycled in the second extraction zone. This operation is costly in energy.
  • One of the objects of the invention is therefore to remedy the above drawbacks.
  • the process according to the invention has the advantage, by using a light gasoline cut 25-80 ° C as an auxiliary solvent for re-extracting the first solvent from aromatic hydrocarbons, of avoiding distillation, which is energy efficient. .
  • the production of this light cut is accompanied by an increase in the quality of the gasoline obtained and simultaneously by the improvement in the quality of kerosene.
  • the initial charge of hydrocarbons used is a charge of hydrocarbons the final boiling point of which is at least 220 ° C., charge for example comprised between its initial boiling point and a final point of 600 ° C., for example example 25 ° C to 350 ° C.
  • This charge can come from a catalytic cracking, thermal cracking or hydrocracking process. It can also be a crude oil charge or a distillate containing at least petrol and kerosene fractions, and which has not undergone the above treatments.
  • an effluent from a catalytic cracking unit in a fluid bed in English "Fluid Catalytic Cracking" (FCC) and whose starting charge has been cracked in the presence of a catalyst under known cracking conditions, will be used. of the Tradesman. This effluent, thus enriched in olefinic hydrocarbons, will help to improve the octane number of the gasoline cut (light).
  • feedstock is fractionated by distillation according to known conventional means.
  • the cuts obtained may, depending on the number of trays in the distillation column, have boiling point ranges which may interfere in part.
  • the lighter gases can be collected separately as well as water and hydrogen sulfide.
  • the light petrol cut generally contains less than 10% by weight of aromatic hydrocarbons and preferably from 0.1 to 5% by weight.
  • the cut of heavy petrol generally contains from 25 to 75% by weight of aromatic hydrocarbons and in general approximately less than 15% by weight, preferably from 1 to 10% by weight approximately of dicyclic hydrocarbons having at least an aromatic cycle.
  • the average gasoline cut can be reformed after hydrotreatment which usually makes it possible to reduce the nitrogen content to less than 1 ppm, before mixing it with the extract and the auxiliary solvent of step c), which will make it possible to further improve the octane number of the resulting mixture.
  • the fractionation of the charge can reveal a boiling point cut above 220 ° C. intended to supply the engine diesel fuel tank (pool).
  • This cut can be a Light Cycle Oil (L.C.O.) cut, if the charge comes from catalytic cracking.
  • At least part of the raffinate from step b) according to the method of the invention can be mixed with at least part of the above cut to supply the engine diesel tank.
  • the average gasoline cut of step a) usually containing from 5 to 50 ppm of nitrogen is hydrotreated in the presence of hydrogen in a hydrotreatment zone.
  • the collected hydrotreatment effluent is subjected to catalytic reforming in the presence of hydrogen in a reforming zone under reforming conditions so to obtain a medium petrol cut with improved octane number.
  • This medium essence can be mixed, at least in part and preferably in whole, with the aromatic extract which is itself in mixture with the 25-80 ° C cut according to step c) of the process and this is thus obtained a gasoline with a better octane number than that according to step c) of the process.
  • the said mixture is then subjected to a hydrotreatment under hydrotreatment conditions such that the amount of nitrogen preferably does not exceed 1 ppm, then the hydrotreatment effluent is subjected to a catalytic reforming in the presence of hydrogen in a zone reforming, according to operating conditions such that a reforming gasoline with improved octane number is obtained.
  • This reforming essence thus obtained can then be mixed at least in part and preferably in whole with at least a part and preferably all of the extract comprising the light gasoline cut 25-80 ° C. produced according to step c) of the process.
  • hydrotreatment operation hydrodesulfurization and hydrodenitrogenation
  • the hydrotreatment operation will be carried out under conditions such that there will generally remain only an amount of sulfur and nitrogen of less than 10 ppm and preferably less than 1 ppm. This operation will depend on the type of load. These conditions are known to those skilled in the art and are described, for example, in US patents 3,044,950.
  • the solvents for extracting aromatic hydrocarbons from the heavy petrol fraction can be those described in US Pat. No. 3,627,671 and preferably dimethylsulfoxide, polyethylene glycol and dimethylformamide. These solvents can advantageously contain water, for example from 0.1 to 20% and preferably from 1 to 10% by weight to best adjust the selectivity of the separation.
  • the auxiliary solvent, in this case the cut 25 ° C-80 ° C, used to separate the first extraction solvent in the second extraction zone may contain in particular when the original charge has been catalytically cracked, a quantity of olefins between 20 and 60% which will contribute to improving the octane number of the gasoline intended for the gasoline tank (pool).
  • all the liquid-liquid extraction devices can be used for example columns with filling, plates or with mechanical agitation (RDC: rotating disc contactor) having in general from 3 to 20 stages and preferably from 5 to 10 stages at a temperature generally between 20 and 120 ° C, advantageously between 60 and 80 ° C and under a pressure allowing to operate in the liquid phase and therefore between 1 and 10 bars, preferably 1 and 3 bars.
  • RDC rotating disc contactor
  • the solvent volume ratio on heavy petrol cut is generally between 1 and 3 and preferably between 1.5 and 2, in the first extraction unit.
  • the ratio between the volume of the light gasoline cut and the volume of the charge introduced, that is to say of the mixture comprising said solvent of first extraction and the extract enriched in hydrocarbons aromatics is generally between 0.5 and 2, preferably between 1 and 1.5.
  • the determination of the engine and research octane numbers is carried out according to the standards ASTM D2699-D2700 while the determination of the smoke point and the cetane number is carried out according to the standards ASTM D1322 and ASTM D 613.
  • a vacuum distillate for example, with boiling points of between about 350 and 550 ° C. is introduced by a line 1 into a catalytic cracking unit 2 where it is cracked under cracking conditions in the presence of a catalyst.
  • the liquid catalytic cracking effluent or feed according to the invention for example 25-550 ° C, after separation of the catalyst is introduced by a line 3 at the base of a distillation unit 4 where it is fractionated.
  • a light petrol fraction 25-80 ° C is collected at the head by a line 5, which will be sent, as will be seen below, to the base of a second extraction unit 19, an average petrol fraction of points d boiling between 80 and 150 ° C and which is sent by a line 6 to a gasoline storage tank (pool) 15.
  • This medium gasoline can be reformed in a reforming unit 12 in the presence of hydrogen supplied by a line 13 and a reforming catalyst.
  • this pretreatment is carried out in a hydrotreatment unit 9, upstream of the reforming unit 12, in the presence of hydrogen supplied by a line 10 and of a hydrotreatment catalyst, and under conditions which make it possible to reach these amounts of nitrogen and sulfur.
  • the hydrotreatment effluent is then sent via a line 11 to the reforming unit.
  • a heavy petrol fraction is also collected, with a boiling point of between approximately 150 ° C. and 220 ° C., which is sent by a line 7 to a first extraction unit 16 supplied with solvent. for the extraction of aromatic hydrocarbons, for example, dimethyl sulfoxide.
  • the refined fraction enriched in non-aromatic hydrocarbons or raffinate is collected at least partly in the upper part of the unit, washed to remove traces of extraction solvent (device not shown diagrammatically in the figure) and it is supplied via a line 18 the kerosene storage tank 23. This fraction has a smoke point improved.
  • a part of this same refined fraction can feed via a line 22 the line 6 for supplying the medium petrol cut upstream of the hydrotreatment 9 and reforming units 12.
  • the amount of raffinate thus mixed with the medium petrol cut is such that the mixture thus obtained has an amount of nitrogen of less than 50 ppm and that it can therefore be hydrotreated in a conventional manner and then subjected to a reforming process, as indicated above to increase its octane number.
  • the hydrotreatment carried out on this mixture makes it possible, as explained above, in particular to lower the sulfur and nitrogen contents to approximately at most 1 ppm and moreover hydrogenate at least part of the olefins of this mixture which can be a poison for the reforming catalyst.
  • the extracted fraction enriched in aromatic hydrocarbons and mixed with the first extraction solvent is drawn off via line 17 and then sent via this line 17 to the top of a second extraction unit 19. It is introduced against the current at the base from this unit a light gasoline cut 25-80 ° C (second auxiliary solvent).
  • This light gasoline is capable of dissolving aromatic hydrocarbons but unable to dissolve a substantial amount of the first extraction solvent, that is to say incapable of dissolving more than 5% and preferably more than 1% of its weight of said solvent .
  • the first extraction solvent is collected at the base of the unit 19 and recycled by a line 21 at the top of the first extraction unit 16.
  • the second extraction effluent of improved octane number, mixed with the light petrol cup is in turn sent to the petrol storage tank 15 by a line 20 after having been freed from the traces of the first extraction solvent by conventional means not shown in the figure.
  • the distillation charge for example from the catalytic cracking unit 2 contains a fraction of boiling point above 220 ° C capable of constituting a light cycle oil fraction (LCO) to supply a line 8 to a motor fuel storage tank (pool 8), it is possible to improve its cetane number by mixing with said LCO cut at least part (for example 80%) of the raffinate of the heavy petrol cut coming from the first extraction unit 16, thanks to a line 24.
  • LCO light cycle oil fraction
  • distillation residue (350 ° C +) is collected at the base of the distillation unit 4 via line 26.
  • the liquid catalytic cracking effluent is subjected to a distillation delivering at least four cuts (Tab. I) E l , E m , E L , and LCO
  • the extraction of the heavy petrol cut is carried out in an extraction unit of the R.D.C. type. at 6 stages, against the current in the presence of dimethyl sulfoxide containing 2% of water, at a temperature of approximately 70 ° C. and at a pressure substantially equal to 2 bars so as to maintain the mixture in the liquid phase.
  • the solvent to charge ratio is approximately 1.6 by volume.
  • the so-called raffinate part is washed with water so that the amount of solvent does not exceed 5 ppm and feeds the kerosene tank or the gas oil.
  • the extract mixed with dimethyl sulfoxide is extracted against the current by the light petrol cut in a second extraction unit of the same type as the first at a pressure substantially equal to 2 bars and at a temperature of around 70 ° C.
  • the solvent (light petrol cut) to charge ratio in the second unit is approximately 1.2 by volume.
  • the undissolved dimethyl sulfoxide is recycled in the first unit while the mixture of aromatic extract and light essence with improved octane number (95) is collected, washed so that there is substantially no more dimethyl sulfoxide and introduced into the tank. petrol storage.
  • the operation is carried out at constant production in gasoline, in kerosene and in diesel.
  • case A where we operate according to the prior art, that is to say the case where a gasoline is conventionally constituted from all of the light and medium gasoline cuts and a part of the heavy gasoline, the other part of the heavy gasoline being intended to supply the engine diesel or kerosene storage tank and case B according to the present invention, without hydrotreating or reforming.
  • a fuel storage tank is supplied by the light petrol cutter and the so-called extract part (EL1) of the heavy petrol cutter which leaves the second extraction unit (46% of the heavy fuel cut, i.e. 7% of the load) as well as the medium fuel cut.
  • an amount of gasoline (37%) of octane number 93 is obtained which can be compared to the same amount of gasoline obtained according to the prior art (the number 7 representing the same amount of heavy gasoline added), or 37%, of octane number 90.
  • Example 2 is carried out according to the conditions of Example 1 according to the method of the invention (case D). However, two modes of implementation are determined, one for winter and the other for summer.
  • the diesel tank is supplied by the L.C.O. while the petrol tank is supplied by the light petrol fraction serving as a solvent for the second extraction, the extract enriched with aromatic hydrocarbons (EL1) according to the process of the invention and the medium petrol as well as the raffinate (ELR) of l heavy gasoline.
  • the raffinate instead of supplying the kerosene or diesel tank, is mixed with the medium petrol cut. This raffinate contains approximately 30 ppm nitrogen. The mixture formed is subjected, after washing intended to rid it of traces of dimethylsulfoxide, to a hydrotreatment and then to reforming under the following conditions described in Table III.
  • the petrol tank is supplied by the light petrol cut, the extract according to the invention and the medium petrol cut subjected to the above hydrotreatment and reforming while the diesel tank is supplied by the LCO cut and the raffinate obtained according to the invention.
  • the diesel fuel tank is conventionally supplied (case C), for the winter, by the LCO cut and part of the heavy petrol (the same quantity as that according to the invention), and supplies the petrol tank with the light petrol cutter, the medium petrol cutter, which has been subjected to the hydrotreatment and reforming processes under substantially the same conditions as those described above, and the additional part of the heavy petrol .
  • the fuel tank is supplied with the light fuel cut, the medium fuel cut which has been subjected to the hydrotreatment and reforming processes as above, and the fuel cut. heavy petrol.
  • Table IV show that the quality of the products obtained is improved when operating according to the process of the invention.

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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)

Claims (10)

1. Verfahren zur Fraktionierung und Extraktion von Kohlenwasserstoffen zur Herstellung von Benzin mit verbesserter Oktanzahl und von Kerosin mit verbessertem Rauchpunkt, bei dem man von einer Kohlenwasserstoff-Beschickung ausgeht, deren Endsiedepunkt mindestens 220°C beträgt und deren Siedepunkte vorzugsweise zwischen 25 und 350°C liegen, das die folgenden Stufen umfaßt:
(a) eine Stufe der Fraktionierung der Beschickung unter Fraktionierungsbedingungen, wobei man mindestens drei Fraktionen erhält:
1. eine leichte Benzinfraktion mit einem Siedepunkt zwischen 25 und 80°C und einem Gehalt an aromatischen Kohlenwasserstoffen von weniger als etwa 10 Gew.-%,
2. eine mittlere Benzinfraktion mit einem Siedepunkt zwischen 80 und höchstens 150°C und einem Stickstoffgehalt von weniger als etwa 50 ppm,
3. eine schwere Benzinfraktion mit einem Siedepunkt von höchstens etwa 220°C und einem Gehalt an aromatischen Kohlenwasserstoffen zwischen 25 und 75 Gew.-%;
(b) eine Stufe der Extraktion des Hauptteils der aromatischen Kohlenwasserstoffe der schweren Benzinfraktion unter Extraktionsbedingungen mit einem ersten Lösungsmittel für aromatische Kohlenwasserstoffe in einer ersten Extraktionszone, die ein entaromatisiertes Raffinat und ein das Lösungsmittel und einen an den aromatischen Kohlenwasserstoffen angereicherten Extrakt enthaltendes Gemisch liefert, wobei das Volumenverhältnis zwischen dem ersten Lösungsmittel und der schweren Benzinfraktion zwischen 1 und 3 liegt;
(c) eine Stufe der Extraktion des Gemisches mit einem zweiten Hilfslösungsmittel unter Extraktionsbedingungen in einer zweiten Extraktionszone, die einerseits den das zweite Hilfslösungsmittel enthaltenden Extrakt und andererseits das erste Lösungsmittel, das in die Stufe (b) zurückgeführt wird, liefert, wobei das Volumenverhältnis zwischen dem Hilfslösungsmittel und dem Gemisch zwischen 0,5 und 2 liegt;
wobei das Verfahren dadurch charakterisiert ist, daß das genannte Hilfslösungsmittel die genannte leichte Benzinfraktion (25-80°C) ist und daß man
(d) mindestens einen Teil des entaromatisierten Raffinats der Stufe (b) in der Weise gewinnt (sammelt), daß man ein Kerosin mit einem verbesserten Rauchpunkt erhält.
2. Verfahren nach Anspruch 1, in dem es sich bei der Kohlenwasserstoff-Beschickung handelt um mindestens einen Abstrom, der stammt aus einer Behandlung, ausgewählt aus der Gruppe der katalytischen Crackung, der thermischen Crackung und der katalytischen Hydrocrackung, oder um mindestens eine Rohöl-Beschickung oder ein Destillat, das keiner der genannten Behandlungen unterworfen worden ist.
3. Verfahren nach Anspruch 1, in dem die KohlenwasserstoffBeschickung das Ergebnis einer Crackung in Gegenwart eines Crackungskatalysators unter Crackungsbedingungen vor dieser Fraktionierung ist.
4. Verfahren nach einem der Ansprüche 1 bis 3, in dem die mittlere Benzinfraktion der Stufe (a) üblicherweise 5 bis 50 ppm Stickstoff enthält und in einer Hydrierungszone unter solchen Hydrierungsbedingungen hydriert wird, daß die Stickstoffmenge nach der Hydrierung unter 1 ppm liegt, und dann der: gesammelte Abstrom der Hydrierungsbehandlung in einer Reformierungszone in Gegenwart von Wasserstoff einer katalytischen Reformierung unter solchen Reformierungsbedingungen unterworfen wird, daß eine mittlere Benzinfraktion mit verbesserter Octanzahl erhalten wird.
5. Verfahren nach einem der Ansprüche 1 bis 4, in dem mindestens ein Teil des Raffinats der Stufe (b) in den Tank eines Dieselmotors in der Weise eingeführt wird, daß man einen Dieselmotor mit verbesserter Cetanzahl erhält.
6. Verfahren nach einem der Ansprüche 1 bis 3, in dem mindestens ein Teil des Raffinats der Stufe (b) mit der mittleren Benzinfraktion der Stufe (a) in einem solchen Mengenverhältnis gemischt wird, daß die Stickstoffmenge des so erhaltenen Gemisches unter 50 ppm bleibt und das Gemisch der in Anspruch 4 genannten Hydrierungsbehandlung und Reformierungsbehandlung unterworfen wird und daß man anschließend ein Reformierungsbenzin gewinnt, das man mit dem Extrakt der Stufe (c) des Anspruchs 1 mischt.
7. Verfahren nach einem der Ansprüche 1 bis 6, in dem die leichte Benzinfraktion (25-80°C) 0,1 bis 5 Gew.-% aromatische Kohlenwasserstoffe enthält.
8. Verfahren nach einem der Ansprüche 1 bis 7, in dem die schwere Benzinfraktion weniger als 15 Gew.-%, vorzugsweise 1 bis 10 Gew.-% dicyclische Kohlenwasserstoffe mit mindestens einem aromatischen Ring enthält.
9. Verfahren nach einem der Ansprüche 1 bis 8, in dem das erste Lösungsmittel Dimethylsulfoxid, Polyethylenglycol oder Dimethylformamid ist.
10. Verfahren nach Anspruch 9, in dem das erste Lösungsmittel 1 bis 10% Wasser enthält.
EP89402119A 1988-08-02 1989-07-26 Kohlenwasserstoff-Fraktionierungs- und Extraktionsverfahren zur Erlangung von Benzin mit verbesserter Oktanzahl und von Kerosin mit verbessertem Rauchpunkt Expired - Lifetime EP0354826B1 (de)

Applications Claiming Priority (2)

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FR8810545A FR2635112B1 (fr) 1988-08-02 1988-08-02 Procede de fractionnement et d'extraction d'hydrocarbures permettant l'obtention d'une essence a indice d'octane ameliore et d'un kerosene a point de fumee ameliore
FR8810545 1988-08-02

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EP0354826A1 EP0354826A1 (de) 1990-02-14
EP0354826B1 true EP0354826B1 (de) 1991-12-04

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US (1) US5021143A (de)
EP (1) EP0354826B1 (de)
JP (1) JPH0275698A (de)
DE (1) DE68900503D1 (de)
ES (1) ES2038427T3 (de)
FR (1) FR2635112B1 (de)

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ES2038427T3 (es) 1993-07-16
EP0354826A1 (de) 1990-02-14
JPH0275698A (ja) 1990-03-15
DE68900503D1 (de) 1992-01-16
FR2635112A1 (fr) 1990-02-09
FR2635112B1 (fr) 1990-09-28
US5021143A (en) 1991-06-04

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