Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • 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
  • C10G67/04—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 solvent extraction 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
  • C10G35/00—Reforming naphtha
  • C10G35/04—Catalytic reforming
  • C10G35/06—Catalytic reforming characterised by the catalyst used
  • C10G35/095—Catalytic reforming characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves
• • 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
  • C10G63/00—Treatment of naphtha by at least one reforming process and at least one other conversion process
  • C10G63/02—Treatment of naphtha by at least one reforming process and at least one other conversion process plural serial stages only
  • C10G63/04—Treatment of naphtha by at least one reforming process and at least one other conversion process plural serial stages only including at least one cracking step
• • 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

• This invention relates to hydrocarbon conversion in a refinery. More specifically it relates to the production of iso-olefins from higher olefins contained in a refinery naptha.
• iso-butylene may be reacted with methanol over an acidic catalyst to provide methyl tertiary butyl ether (MTBE) and iso-amylenes may be reacted with methanol over an acidic catalyst to produce tertiary-amyl methyl ether (TAME).
• MTBE methyl tertiary butyl ether
• TAME tertiary-amyl methyl ether
• iso-olefins often do not exist in refinery streams in the quantities required for desired MTBE and TAME production levels.
• olefin content of motor gasoline is limited using an analytical indicator such as Bromine Number. Due to the relatively high olefin content of some refinery streams, such as FCC gasoline, their use as blending stock for motor gasoline is constrained. FCC octane improvement often is achieved or accompanied by increased production of olefins, particularly olefins in the C5 - C9 range. The refiner is therefore limited in FCC performance by the mandated olefin limitation.
• U.S. Patent No. 5,004,852 issued April 2, 1991 to Harandi, describes a catalytic technique for upgrading olefin streams to gasoline streams rich in aromatics.
• it provides a continuous process for oligomerizing and aromatizing a feedstock containing light C4-olefins to produce C5+ hydrocarbons rich in C6-C10 aromatics, such as benzene, toluene, xylenes, tri-methylbenzenes and tetramethylbenzenes together with hydrogen and fuel gas.
• U.S. Patent No. 5,026,936 issued June 25, 1991 to Leyshon, et al., teaches fluidized bed cracking and metathesis of butenes or higher olefins and/or paraffins for the production of ethylene and propylene with acidic ZSM-5 at: high space rate, between 5 to 2000, moderate pressures, -5 to 30 psig, and temperatures between 750 to 1472°F.
• the production of iso-butylene by the iso-olefin production process described in this invention is accomplished with just trace, if any, production of butadiene along with the transformation of pentadienes such that the cracked olefinic gasoline contains substantially less pentadienes and little if any butadienes, relative to the olefinic feed naptha.
• the production of essentially butadiene-free iso-butylene and essentially pentadiene-free iso-pentenes obviate the need for diolefin clean-up steps normally required before either MTBE and/or TAME production units.
• the present invention is a process which combines the use of a particular feedstream, in a reaction in the presence of a particular catalyst, to yield the advantageous result of increasing the production of particular components in a product stream.
• the product stream, then having more desirable levels of particular components, may then be further processed.
• the olefinic feed to our process is FCC gasoline from an FCC unit.
• FCC gasolines comprising olefins in the range of C5 to C9, are effectively processed by the present process, but our best iso-butene and iso-pentene production results were accomplished when the FCC gasoline had a boiling range of between about 65°F to about 340°F.
• Other olefinic naphthas like pyrolysis naphthas, naphthas from the production of ethylene and propylene, coker naphthas or naphthas from propylene oligomerization can be used.
• the stream comprising normal and iso-butylenes are fed to a MTBE unit.
• the stream comprising iso-pentenes are feed to a TAME unit.
• propylene from the reaction of the naptha olefins is recycled back to be blended with incoming olefinic naptha feed to the crystalline silicate-containing reactor.
• Propylene recycle ratios relative to total feed to the crystalline silicate-containing reactor in the range of about 2% to about 20% are preferred.
• unreacted butenes comprised chiefly of n-butylene, from the MTBE unit are returned to the crystalline silicate-containing reactor where at least a portion of the n-butylene is converted to iso-butylene.
• fractionating a C5 to c7 cut from the iso olefin enriched product stream exiting the crystalline silicate-containing reactor yields an iso-olefin rich stream which can be disproportionated with ethylene and/or propylene, which may be from any source including FCC produced ethylene and/or propylene, to yield additional iso-butylene and iso-pentene.
• the resulting normal butylene from the disproportionation unit can be either recycled or alkylated while iso-butylene can be used for MTBE production and iso-pentene for TAME.
• a process is carried out for increasing iso-butylene and enhanced iso-pentene to total pentene ratio from a refinery naphtha.
• the process comprises the steps of contacting a olefinic naptha stream comprising C5-C9 olefins with a crystalline silicate catalyst at a temperature of between about 500°F to about 900°F to produce an iso-butylene and iso-pentene rich product stream comprising iso-butylene and iso-pentene, saturated butanes and propylene.
• iso-butylene rich and iso-pentene rich we mean the total amount of iso-butylene in the product stream relative to the total amount of iso-butylene in the naphtha and iso-pentene/total pentene ratio in the product stream relative to iso-pentene/total pentene ratio in the naptha is increased.
• the reactor utilized in the practice of the present invention may be a moving bed or fluidized bed and is preferably a fixed-bed reactor.
• the catalyst used in the reactor is a crystalline silicate.
• the crystalline silicate component of the catalyst of the present invention is generally referred to herein as silicate or crystalline silicate, but also is commonly referred to as a zeolite.
• the silicate of the catalyst of the present invention preferably is low in acidity.
• the low acidity may be achieved by a combination of low aluminum content in the silicate and the use of low amounts of alkali and/or the use of alkaline earth metals.
• the silicate component of the catalyst preferably is included in a matrix or binder to form the finished catalyst, as described hereinbelow.
• the finished catalyst is of low acidity.
• the present invention uses an intermediate pore size crystalline silicate material having a high silica to alumina ratio.
• One preferred material is "silicalite” or high ratio silica to alumina form of ZSM-5.
• the values in Table 1 were determined by standard techniques.
• the radiation was the K-alpha doublet of copper, and a scintillation counter spectrometer with a strip chart pen recorder was used.
• ZSM-5 is regarded by many to embrace "silicalite" as disclosed in U.S. Patent No. 4,061,724 to Grose et al.
• silicalite is referred to as a ZSM-5-type material with a high silica to alumina ratio and is regarded as embraced within the ZSM-5 X-ray diffraction pattern.
• the silica to alumina ratio is on a molar basis of silica (SiO2) to alumina (Al2O3).
• ZSM-5 is more particularly described in U.S. Patent No. 3,702,886 and U.S. Patent Reissue No. 29,948, the entire contents of which are incorporated herein by reference.
• ZSM-11 is more particularly described in U.S. Patent No. 3,709,979 the entire contents of which are incorporated herein by reference.
• Bibby et al., Nature, 280, 664-665 (August 23, 1979) reports the preparation of a crystalline silicate called "silicalite-2".
• ZSM-12 is more particularly described in U.S. Patent No. 3,832,449, the entire contents of which are incorporated herein by reference.
• ZSM-22 is more particularly described in U.S. Patent Nos. 4,481,177, 4,556,477 and European Patent No. 102,716, the entire contents of each being expressly incorporated herein by reference.
• ZSM-23 is more particularly described in U.S. Patent No. 4,076,842, the entire contents of which are incorporated herein by reference.
• ZSM-35 is more particularly described in U.S. Patent No. 4,016,245, the entire contents of which are incorporated herein by reference.
• ZSM-38 is more particularly described in U.S. Patent No. 4,046,859, the entire contents of which are incorporated herein by reference.
• ZSM-48 is more particularly described in U.S. Patent No. 4,397,827 the entire contents of which are incorporated herein by reference.
• ZSM-5 ZSM-11, ZSM-22 and ZSM-23 are preferred.
• ZSM-5 is most preferred for use in the catalyst of the present invention.
• zeolites SSZ-20, SSZ-23 and SSZ-32 are preferred.
• SSZ-20 is disclosed in U.S. Patent No. 4,483,835, and SSZ-23 is disclosed in U.S. Patent No. 4,859,442, both of which are incorporated herein by reference.
• the crystalline silicate may be in the form of a borosilicate, where boron replaces at least a portion of the aluminum of the more typical aluminosilicate form of the silicate.
• Borosilicates are described in U.S. Patent Nos. 4,268,420; 4,269,813; and 4,327,236 to Klotz, the disclosures of which patents are incorporated herein, particularly that disclosure related to borosilicate preparation.
• the preferred crystalline structure is that of ZSM-5, in terms of X-ray diffraction pattern.
• Boron in the ZSM-5 type borosilicates takes the place of aluminum that is present in the more typical ZSM-5 crystalline aluminosilicate structures.
• Borosilicates contain boron in place of aluminum, but generally there is some trace amounts of aluminum present in crystalline borosilicates.
• Still further crystalline silicates which can be used in the present invention are ferrosilicates, as disclosed for example in U.S. Patent No. 4,238,318, gallosilicates, as disclosed for example in U.S. Patent No. 4,636,483, and chromosilicates, as disclosed for example in U.S. Patent No. 4,299,808.
• silica content silicates silicates having a high ratio of silica to other constituents
• crystalline silicate component of the catalyst of the present invention various high silica content silicates (silicates having a high ratio of silica to other constituents) can be used as the crystalline silicate component of the catalyst of the present invention.
• Borosilicates and aluminosilicates are preferred silicates for use in the present invention.
• Aluminosilicates are the most preferred.
• Silicalite is a particularly preferred aluminosilicate for use in the catalyst of the present invention.
• silicalite As synthesized, silicalite (according to U.S. Patent No. 4,061,724) has a specific gravity at 77°F of 1.99 ⁇ 0.05 g/cc as measured by water displacement. In the calcined form (1112°F in air for one hour), silicalite has a specific gravity of 1.70 ⁇ 0.05 g/cc. With respect to the mean refractive index of silicalite crystals, values obtained by measurement of the as synthesized form and the calcined form (1112°F in air for one hour) are 1.48 ⁇ 0.01 and 1.39 ⁇ 0.01, respectively.
• the X-ray powder diffraction pattern of silicalite (1112°F calcination in air for one hour) has six relatively strong lines (i.e., interplanar spacings). They are set forth in Table 2 ("S"-strong, and "VS"-very strong): TABLE 2 d-A Relative Intensity 11.1 ⁇ 0.2VS 10.0 ⁇ 0.2VS 3.85 ⁇ 0.07VS 3.82 ⁇ 0.07S 3.76 0.05S 3.72 ⁇ 0.05S
• Table 3 shows the X-ray powder diffraction pattern of a typical silicalite composition containing 51.9 mols of SiO2 per mol of tetrapropyl ammonium oxide [(TPA)2O), prepared according to the method of U.S. Patent No. 4,061,724, and calcined in air at 1112°F for one hour.
• the pore diameter of silicalite is about 6 ⁇ and its pore volume is 0.18 cc/gram as determined by adsorption.
• Silicalite adsorbs neopentane (6.2 ⁇ kinetic diameter) slowly at ambient room temperature.
• the uniform pore structure imparts size-selective molecular sieve properties to the composition, and the pore size permits separation of p-xylene from o-xylene, m-xylene and ethyl-benzene as well as separations of compounds having quaternary carbon atoms from those having carbon-to-carbon linkages of lower value (e.g., normal and slightly branched paraffins).
• the crystalline silicates of U.S. Patent Reissue No. 29,948 (Reissue of USP 3,702,886 to Argauer) are disclosed as having a composition, in the anhydrous state, as follows: 0.9 ⁇ 0.2 [xR2O + (1 - x)M 2/n O]: ⁇ .005 Al2O3:>1 SiO2 where M is a metal, other than a metal of Group IIIA, n is the valence of said metal, R is an alkyl ammonium radical, and x is a number greater than 0 but not exceeding 1.
• the crystalline silicate is characterized by the X-ray diffraction pattern of Table 1, above.
• the crystalline silicate polymorph of U.S. Patent No. 4,073,865 to Flanigen et al. is related to silicalite and, for purposes of the present invention, is regarded as being in the ZSM-5 class.
• the crystalline silicate exhibits the X-ray diffraction pattern of Table 4.
• a silicalite-2 precursor can be prepared using tetra-n-butylammonium hydroxide only, although adding ammonium hydroxide or hydrazine hydrate as a source of extra hydroxyl ions increases the reaction rate considerably. It is stable at extended reaction times in a hydrothermal system.
• 8.5 mol SiO2 as silicic acid (74% SiO2) is mixed with 1.0 mol tetra-n-butylammonium hydroxide, 3.0 mol NH4OH and 100 mol water in a steel bomb and heated at 338°F for three days.
• the precursor crystals formed are ovate in shape, approximately 2-3 microns long and 1-1.5 microns in diameter.
• silicalite-2 precursor will not form if Li, Na, K, Rb or Cs ions are present, in which case the precursor of the U.S. Patent No. 4,061,724 silicalite is formed. It is also reported that the size of the tetraalkylammonium ion is critical because replacement of the tetra-n-butylammonium hydroxide by other quaternary ammonium hydroxides (such as tetraethyl, tetrapropyl, triethylpropyl, and triethylbutyl hydroxides) results in amorphous products.
• quaternary ammonium hydroxides such as tetraethyl, tetrapropyl, triethylpropyl, and triethylbutyl hydroxides
• the amount of Al present in silicalite-2 depends on the purity of the starting materials and is reported as being less than 5 ppm.
• the precursor contains occluded tetraalkylammonium salts which, because of their size, are removed only by thermal decomposition. Thermal analysis and mass spectrometry show that the tetraalkylammonium ion decomposes at approximately 572°F and is lost as the tertiary amine, alkene and water. This is in contrast to the normal thermal decomposition at 392°F of the same tetraalkylammonium salt in air.
• the measured densities and refractive indices of silicalite-2 and its precursor are reported as 1.82 and 1.98 g/cc and 1.41 and 1.48 respectively.
• silicalite is regarded as being in the ZSM-5 class, alternatively put, as being a form of ZSM-5 having a high silica to alumina ratio; silicalite-2 is regarded as being in the ZSM-11 class.
• the preparation of crystalline silicates of the present invention generally involves the hydrothermal crystallization of a reaction mixture comprising water, a source of silica, and an organic templating compound at a pH of 10 to 14.
• Representative templating moieties include quaternary cations such as XR4 where X is phosphorous or nitrogen and R is an alkyl radical containing from 2 to 6 carbon atoms, e.g., tetrapropylammonium hydroxide (TPA-OH) or halide, as well as alkyl hydroxyalkyl compounds, organic amines and diamines, and heterocycles such as pyrrolidine.
• the reaction mixture may contain only water and a reactive form of silica as additional ingredients.
• ammonium hydroxide or alkali metal hydroxides can be suitably employed for that purpose, particularly the hydroxides of lithium, sodium and potassium.
• the ratio: R+ to the quantity R+ plus M+, where R+ is the concentration of organic templating cation and M+ is the concentration of alkali metal cation, is preferably between 0.7 and 0.98, more preferably between 0.8 and 0.98, most preferably between 0.85 and 0.98.
• the source of silica in the reaction mixture can be wholly, or in part, alkali metal silicate.
• Other silica sources include solid reactive amorphous silica, e.g., fumed silica, silica sols, silica gel, and organic orthosilicates.
• One commercial silica source is Ludox AS-30, available from DuPont.
• Aluminum usually in the form of alumina, is easily incorporated as an impurity into the crystalline silicate.
• Aluminum in the crystalline silicate contributes acidity to the catalyst, which is undesirable.
• Commercially available silica sols can typically contain between 500 and 700 ppm alumina, whereas fumed silicas can contain between 80 and 2000 ppm of alumina impurity.
• the silica to alumina molar ratio in the crystalline silicate of the catalyst used in the present invention is preferably greater than 200:1.
• the quantity of silica in the reaction system is preferably between about 1 and 10 mols SiO2 per mol-ion of the organic templating compound. Water should be generally present in an amount between 20 and 700 mol per mol-ion of the quaternary cation.
• the reaction preferably occurs in an aluminum-free reaction vessel which is resistant to alkali or base attack, e.g., Teflon.
• the crystalline silicate is preferably bound with a matrix.
• matrix includes inorganic compositions with which the silicate can be combined, dispersed, or otherwise intimately admixed.
• the matrix is not catalytically active in a hydrocarbon cracking sense, i.e., contains substantially no acid sites.
• Satisfactory matrices include inorganic oxides. Preferred inorganic oxides include alumina, silica, alumina-alumina-phosphates, naturally occurring and conventionally processed clays, for example bentonite, kaolin, sepiolite, attapulgite and halloysite.
• Preferred matrices are substantially non-acidic and have little or no cracking activity.
• Silica matrices and also alumina matrices are especially preferred.
• a low acidity matrix more preferably a substantially non-acidic matrix, is advantageous in the catalyst of the present invention.
• Compositing the crystalline silicate with an inorganic oxide matrix can be achieved by any suitable method wherein the silicate is intimately admixed with the oxide while the latter is in a hydrous state (for example, as a hydrous salt, hydrogel, wet gelatinous precipitate, or in a dried state, or combinations thereof).
• a convenient method is to prepare a hydrous mono or plural oxide gel or cogel using an aqueous solution of a salt or mixture of salts (for example, aluminum sulfate and sodium silicate).
• Ammonium hydroxide carbonate (or a similar base) is added to the solution in an amount sufficient to precipitate the oxides in hydrous form.
• the precipitate is washed to remove most of any water soluble salts and it is thoroughly admixed with the silicate which is in a finely divided state.
• Water or a lubricating agent can be added in an amount sufficient to facilitate shaping of the mix (as by extrusion).
• a preferred crystalline silicate for use in the catalyst of the present invention is ZSM-5 having a high silica to alumina ratio, which, for convenience, is frequently referred to herein as "silicalite".
• silicalite preferably has a percent crystallinity of at least 80%, more preferably at least 90%, most preferably at least 95%.
• XRD X-ray diffraction
• the preferred crystallite size of the crystalline silicate is less than 10 microns, more preferably less than 5 microns, still more preferably less than 2 microns, and most preferably less than 1 micron.
• a crystallite size is specified, preferably at least 70 wt. % of the crystallites are that size, more preferably at least 80 wt. %, most preferably 90 wt. %.
• Crystallite size can be controlled by adjusting synthesis conditions, as known to the art. These conditions include temperature, pH, and the mole ratios H2O/SiO2, R+/SiO2, and M+/SiO2, where R+ is the organic templating cation and M+ an alkali metal cation.
• the crystalline silicate component of the catalyst of the present invention has an intermediate pore size.
• intermediate pore size as used herein is meant an effective pore aperture in the range of about 5 to 6.5 ⁇ when the silicate is in the H-form. Crystalline silicates having pore apertures in this range tend to have unique molecular sieving characteristics. Unlike small pore crystalline silicates or zeolites such as erionite, they will allow hydrocarbons having some branching into the zeolitic void spaces.
• n-alkanes can differentiate between n-alkanes and slightly branched alkanes on the one hand and larger branched alkanes having, for example, quarternary carbon atoms.
• the effective pore size of the crystalline silicates or zeolites can be measured using standard adsorption techniques and hydrocarbonaceous compounds of known minimum kinetic diameters. See Breck, Zeolite Molecular Sieves , 1974 (especially Chapter 8) and Anderson et al., J.Catalysis 58, 114 (1979), both of which are incorporated by reference.
• Intermediate pore size crystalline silicates or zeolites in the H-form will typically admit molecules having kinetic diameters of 5 to 6 ⁇ with little hindrance.
• Examples of such compounds are: n-hexane (4.3), 3-methylpentane (5.5), benzene (5.85), and toluene (5.8).
• Compounds having kinetic diameters of about 6 to 6.5 ⁇ can be admitted into the pores, depending on the particular zeolite, but do not penetrate as quickly and in some cases, are effectively excluded (for example, 2,2-dimethylbutane is excluded from H-ZSM-5).
• Compounds having kinetic diameters in the range of 6 to 6.5 ⁇ include: cyclohexane (6.0), m-xylene (6.1) and 1,2,3,4-tetramethylbenzene (6.4). Generally, compounds having kinetic diameters of greater than about 6.5 ⁇ cannot penetrate the pore apertures and thus cannot be adsorbed in the interior of the zeolite. Examples of such larger compounds include: o-xylene (6.8), hexamethylbenzene (7.1), 1,3,5-trimethylbenzene (7.5), and tributylamine (8.1).
• the preferred effective pore size range is from about 5.3 to about 6.2 ⁇ .
• intermediate pore size zeolites include silicalite and members of the ZSM series such as ZSM-5, ZSM-11, ZSM-12, ZSM-21, ZSM-22, ZSM-23, ZSM-35, ZSM-38, SSZ-20, SSZ-23 and SSZ-32.
• FCC Unit A An FCC light gasoline feed recovered from an operating refinery FCC unit, "FCC Unit A,” and having the following properties was used to demonstrate the process of this invention:
• the feed having the properties shown in Table I was passed over a catalyst consisting of 100% Conteka silicalite with a 400 SiO2/Al2O3 ratio at temperatures between 750 and 850°F and at total pressures between 0 to 150 psig (14.7 to 164.7 psia).

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• 1992
  • 1992-08-21 EP EP92114377A patent/EP0534142A1/fr not_active Withdrawn
  • 1992-09-10 JP JP24217092A patent/JPH0656707A/ja active Pending

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