US3451922A - Method for hydrogenation - Google Patents

Method for hydrogenation Download PDF

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US3451922A
US3451922A US634554A US3451922DA US3451922A US 3451922 A US3451922 A US 3451922A US 634554 A US634554 A US 634554A US 3451922D A US3451922D A US 3451922DA US 3451922 A US3451922 A US 3451922A
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fraction
reaction zone
hydrocarbons
gasoline
reactor
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Robin J Parker
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Universal Oil Products Co
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Universal Oil Products Co
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
    • C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
    • C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
    • C10G65/06—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps at least one step being a selective hydrogenation of the diolefins
    • 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 the hydrogenation of hydrocarbons. It particularly relates to the stabilization of pyrolysis gasoline. It specifically relates to a method for selectively removing diolefins and olefins from the product gasoline obtained in light olefin manufacture.
  • the effluent from the cracking zone may comprise light olefinic hydrocarbons such as ethylene, propylene, butylene, etc. or mixtures thereof, all of which may constitute the principal product or products.
  • light olefinic hydrocarbons such as ethylene, propylene, butylene, etc. or mixtures thereof, all of which may constitute the principal product or products.
  • pyrolysis gasoline which contains undesirable quantities of diolefin hydrocarbons and/ or sulfur compounds.
  • the pyrolysis gasoline frequently is rich in aromatic hydrocarbons, but it has been found that usually the aromatic portion of the pyrolysis gasoline is also heavily contaminated with olefin hydrocarbons which renders recovery of the aromatics in high purity extremely diflicult.
  • a pyrolysis unit may charge ethane, propane, or a straight-run naphtha fraction containing about 5% aromatic hydrocarbons, to a pyrolysis unit.
  • the pyrolysis efiluent is separated into desired fractions, one fraction of which usually comprises a C 400 F.
  • pyrolysis gasoline which represents, for example, approximately 1% to 40% by weight of the original naphtha feed depending upon the charge stock and severity of cracking. Since the pyrolysis gasoline is heavily contaminated, as previously mentioned, it is hydrotreated for saturation of olefin and/or diolefin compounds and for removal of sulfur compounds.
  • the prior art schemes also charge the hydrotreated pyrolysis gasoline fraction to an aromatic extraction unit for recovery of the aromatic hydrocarbons such as benzene, toluene, and xylene therefrom.
  • aromatic hydrocarbons such as benzene, toluene, and xylene therefrom.
  • Typical extraction procedures utilizing a solvent such as sulfolane or the glycols are well known to those skilled in the art for aromatic extraction purposes.
  • the diene content of such pyrolysis gasoline is usually within the range Patented June 24, 1969 from 20 to 70 for C -400" F. gasolines.
  • the diolefin compounds pose particular difiiculty in the operation of the hydro-treating facilities since these compounds cause extensive equipment fouling and catalyst bed fouling. So far as is known, the prior art, hydrotreating process will experience this fouling from polymer formation to some extent.
  • the prior art will attempt to improve the on-stream efiiciency of the hydrotreating unit by either promoting the polymerization reaction prior to the hydrotreating step thereby preventing the polymer from reaching downstream equipment and/ or utilizing operating techniques and schemes which tend to minimize polymer formation. None of the prior art approaches are completely successful in overcoming the fouling difiiculty resulting from the diolefin compounds present in the pyrolysis gasoline.
  • the prior art schemes do not povide selectivity in the hydrotreating unit.
  • the hydrogenation reaction may not stop with the conversion of diolefins to olefins but will frequently saturate the amount of olefins completely and even hydrogenate substantial portions of aromatic hydrocarbons.
  • Such nonselectivity results in a decreased yield of desirable products in the pyrolysis gasoline.
  • aromatic hydrocarbons may not be hydrogenated, more frequently, olefin hydrocarbons are completely saturated, thereby significantly decreasing the octane blending value of that portion of the pyrolysis gasoline which is normally utilized in motor fuel.
  • the practice of the present invention provides a method for hydrogenating hydrocarbons which comprises introducing a relatively heavy hydrocarbon feedstock containing diolefin and olefin compounds into a first reaction zone maintained under hydrogenation conditions including a relatively low temperature and the presence of a palladium-containing catalyst suflicient to convert diolefin compounds to olefin compounds; passing the total eflluent from the first reaction zone into a second reaction zone maintained under hydrogenation conditions including a relatively high temperature and the presence of a desulfurization catalyst sufiicient to substantially saturate olefin compounds and convert sulfur compounds to hydrogen sulfide; admixing the total efliuent from the second reaction zone with a relatively light hydrocarbon feedstock containing diolefin and olefin compounds; passing said admixture into a third reaction zone maintained under hydrogenation conditions including a relatively low temperature and the presence of a palladium-containing catalyst sufficient to convert diolefin compounds; to ole
  • Another embodiment of the invention includes the method hereinabove wherein said relatively heavy hydrocarbon feedstock comprises the C -40O" F. fraction of pyrolysis gasoline and said relatively light hydrocarbon feedstock comprises the C fraction of said pyrolysis gasoline.
  • a particular embodiment of this invention includes the methods hereinabove wherein said desulfurization catalyst comprises a nickel-containing catalyst.
  • the selectivity of the present invention is based on the discovery that the unique three-stage system for hydrogenation accomplishes the desired results of removing diolefins, selectively removing olefins, and removing sulfur compounds simultaneously from various fractions of pyrolysis gasoline so that maximum recovery of desired products may be obtained from the pyrolysis of ethane, propane and naphthas to produce, for example, ethylene.
  • This invention achieves these results in an economical and facile manner.
  • the use of the palladium catalyst in the first reaction zone achieves selectively the conversion of diolefins to olefins without substantial desulfurization. This is accomplished by maintaining the temperature in the first stage below desulfurization temperatures.
  • Satisfactory operation may be achieved in the first reaction zone at a temperature from 200 F. to 400 F., a pressure from 200 p.s.i.g. to 1200 p.s.i.g., a liquid hourly space velocity from 1 to based on combined feed, and a molar excess of hydrogen.
  • hydrogen in an amount from 500 to 5,000 standard cubic feet per barrel (s.c.f./b.) based on combined or total feed to the reactor will be satisfactory.
  • the operation performed in the second reaction zone of the present invention is primarily one of desulfurization utilizing any of the well known desulfurization catalysts. It was found that the conventional nickel-containing desulfurization catalyst was particularly satisfactory in removing sulfur from the relatively heavy fraction of pyrolysis gasoline while simultaneously saturating the olefin compounds. By proper selection of operating conditions it was found that no substantial aromatic saturation was achieved. Particularly satisfactory operating conditions for the second reaction zone include a temperature from 600 F. to 800 F., a pressure substantially the same as the pressure in the first reaction zone and a catalyst particularly useful for desulfurization such as, for example, nickel-molybdate supported on alumina.
  • the operating conditions for the third reaction zone are particularly important. It is noted that in the practice of the invention the entire hydrocarbon efiluent from the second reaction stage is admixed with the relatively light fraction obtained from the pyrolysis gasoline. The purpose of this admixing is to reduce the Diene Value of the total feed to the third reaction zone to a relatively low figure. It has been found that the C fraction of pyrolysis gasoline contains, for example, from 50% to 80% by weight conjugated diolefin hydrocarbons. These diolefins would contribute significantly to polymer formation in the third reaction zone. Accordingly, it was found that the use of the substantially saturated hydrocarbon efiluent from the second reaction zone as diluent was particularly advantageous.
  • the third reaction zone utilizes the particularly satisfactory palladium catalyst.
  • the diolefins are selectively converted to olefins at a temperature from 290 F. to 550 F., preferably, 360 F. to 500 F. It was found that operating outside of these temperature limits did not produce a particularly desirable result. Therefore, it is important that the temperature of the third reaction zone be maintained within these temperature limits for otherwise the olefin hydrocarbons would be unduly saturated and/ or the dienes would be converted to undesirable dicyclopentadiene which is extremely difficult to remove from the gasoline fraction. Frequently increased liquid hourly space velocity (LHSV) over those of the first reaction zone may be utilized herein. An LHSV of from 5 to based on combined feed is satisfactory. Again, the pressure on the third reaction zone is substantially the same as that on the other two reaction zones allowing for normal pressure drop through the system.
  • LHSV liquid hourly space velocity
  • addition of fresh hydrogen to the other two reaction zones may be desirable from time to time.
  • the present invention is based on the discovery that the palladiumcontaining catalyst is particularly useful in selectively converting dienes to olefins. Contrary to teachings found in the prior art a platinum-containing catalyst was not satisfactory in the practice of the present invention. It was also distinctly discovered that palladium deposited on lithiated alumina support produced excellent results. The amount of lithium on the support achieved remarkable results in reducing gum formation caused by polymerization of the dienes on the acid sites of the catalyst.
  • the palladium-containing catalyst employed in the present invention is prepared utilizing spherical alumina particles formed in accordance with the well known oil drop method as described in US. Patent No. 2,620,314 issued to James Hoekstra. These preferred catalysts contain either 0.75% or 0.375% by weight of palladium incorporated by way of an impregnation technique using the proper quantities of dinitro-dianisole palladium. Following evaporation to visual dryness and drying in air for about an hour at F., the palladium impregnated alumina is calcined at about 1100 F. for about two hours.
  • a distinctly preferred diene hydrogenation catalyst includes 0.4 weight percent palladium, 0.5 weight percent lithium on a inch spherical base.
  • the particularly preferred catalyst for the first and third reaction zones of the present invention comprises lithiated alumina containing from about 0.05% to about 5.0% by weight of palladium.
  • the practice of the present invention as previously noted is particularly applicable to a feedstock obtained from the pyrolysis of naphthas for the production of light olefinic gases such as ethylene.
  • the pyrolysis reaction for the conversion of hydrocarbons into normally gaseous olefinic hydrocarbons is obtained at operating conditions including a temperature from 1000" F. to 1700 R, preferably, 1350" F. to 1550 F., a pressure from 0 to 20 p.s.i.g., preferably 5 to 10 p.s.i.g., and a residence time in the reaction zone of from 0.5 to 25 seconds, preferably, from 3 to 10 seconds.
  • an inlet diluent such as steam, light gases, and the like
  • superheated steam as the diluent which is added to the reaction zone in an amount from 0.2 to 1.0 pound of steam per pound of hydrocarbon, preferably, from 0.3 to 0.7 pound per pound, and typically, about 0.5 pound per pound.
  • a typical pyrolysis gasoline comprising C material separated from the effluent of a steam pyrolysis reaction zone is passed via line 10 into depentanizer tower 11. Suitable conditions are maintained in depentanizer tower 11 to separate the feed to a C fraction and a (3 fraction.
  • the C fraction contains primarily hydrocarbons comprising C paraffius and naphthenes, C olefins and C diolefin hydrocarbons. There may in some cases be small amounts of light hydrocarbons such as the 0., present, but usually this light hydrocarbon contaminant is not significant.
  • the C fraction is removed from depentanizer tower 11 for further use in the third reaction zone more fully discussed hereinbelow.
  • the heavy portion of the feed is removed via line 12 and, preferably, is introduced into rerun column 13.
  • the purpose of column 13 is to produce a distinctly desired fraction, namely, a C -370 CF. fraction of the pyrolysis gasoline which contains the greatest concentration of desirable aromatic hydrocarbons such as benzene, toluene, and xylene.
  • columns via line 32 and a normally liquid hydrocarbon fraction containing the desired hydrogenated products is removed via line 35.
  • the hydrogenated product containing stream i line .35 is then passed into post-fractionation facilities 36 for separation into desired fractions.
  • a C gasoline 11 and 13 may be merged into a single column, but genfraction 1s removed via line 37 and 1s suitable for gasoerally, it is preferable to maintain them as separate colline blending since it still contains a substantial quantity umns.
  • the undesirable 370 F.+ material is removed of olefin hydrocarbons.
  • An aromatics fraction rich in from rerun column 13 via line 14 and disposed of by benzene, xylene, and toluene (BTX) is withdrawn via means known to those skilled in the art. line 38 and is suitable for feed to a, for example, sulfo- The desired C -370 P.
  • the T f d to reactor 18 was a C -370 F. fraction sep effl ent from reactor 27 1S e y Vla line 23, rated from pyrolysis gasoline and the fresh feed to reactor 1 cooler and Passed Vla 11116 Into separatlon 27 was a C fraction separated from the same pyrolysis zone 31. gasoline. The following material balances were obtained COnditiOnS are maintained in Separation Zone 31 Wherewhile operating under the conditions above and with the by a gaseous fraction comprising hydrogen is removed distinctly preferred catalyst previously mentioned:
  • a preferred embodiment of the present invention provides a method for stabilizing pyrolysis gasoline which comprises the steps of: (a) separating pyrolysis gasoline into a relatively light fraction and a relatively heavy fraction; (b) introducing said heavy fraction into a first hydrogenation reaction zone under conditions including the presence of a palladium-containing catalyst sufiicient to convert diolefins to olefins; (c) passing the total effluent from the first reaction zone into a second hydrogenation reaction zone under conditions including the presence of a desulfurization catalyst sufficient to substantially saturate olefins and convert sulfur compounds to hydrogen sulfide; (d) admixing the total efiluent from said second zone with said relatively light fraction; (e) passing said admixture into a third hydrogenation reaction zone under conditions including the presence of a palladium-containing catalyst sufficient to convert diolefins to olefins; and, (f) recovering stabilized pyrolysis
  • Another preferred embodiment of the invention includes the preferred embodiment hereinabove wherein a portion of said stabilized gasoline from Step (f) is returned to Step (b) as diluent in said heavy fraction in an amount sufficient to maintain the combined feed to said first reaction zone at a Diene Value of less than 12.
  • a distinctly preferred embodiment of this invention provides a method for hydrogenating a sulfur-containing pyrolysis gasoline which comprises the steps of: (a) separating said gasoline into a relatively light fraction comprising C hydrocarbons and a relatively heavy fraction comprising C to 400 F. hydrocarbons; (b) admixing said heavy fraction with hydrogen and 'a hereinafter specified recycle stream and introducing said admixture into a first reaction zone containing hydrogenation catalyst comprising palladium on lithiated alumina under conditions including a temperature from 300 F. to 400 F., a pressure from 200 p.s.i.g.
  • suflicient to substantially convert olefins to saturates and sulfur compounds to hydrogen sulfide (d) passing the total effiuent from the second reaction zone together with said relatively light fraction into a third reaction zone containing hydrogenation catalyst comprising palladium on lithiated alumina under conditions including the presence of hydrogen at a temperature from 290 F. to 550 F.
  • Method for hydrogenating sulfur-containing pyrolysis gasoline which comprises the steps of:
  • Step (b) Method according to claim 1 wherein the hydrogen admixed with the heavy fraction in Step (b) is in an amount from 500 to 5,000 s.c. f./b. based on combined feed.

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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)
US634554A 1967-04-28 1967-04-28 Method for hydrogenation Expired - Lifetime US3451922A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US63455467A 1967-04-28 1967-04-28
GB31060/69A GB1236341A (en) 1967-04-28 1969-06-19 Hydrogenation process
FR6920936A FR2104631B1 (enrdf_load_stackoverflow) 1967-04-28 1969-06-23
CA055112A CA923062A (en) 1967-04-28 1969-06-23 Hydrogenation process
DE19691931952 DE1931952B2 (de) 1967-04-28 1969-06-24 Verfahren zum hydrieren von schwefelhaltigem pyrolyseprodukt

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US3451922A true US3451922A (en) 1969-06-24

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US634554A Expired - Lifetime US3451922A (en) 1967-04-28 1967-04-28 Method for hydrogenation

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US (1) US3451922A (enrdf_load_stackoverflow)
CA (1) CA923062A (enrdf_load_stackoverflow)
DE (1) DE1931952B2 (enrdf_load_stackoverflow)
FR (1) FR2104631B1 (enrdf_load_stackoverflow)
GB (1) GB1236341A (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3764521A (en) * 1971-10-18 1973-10-09 Dow Chemical Co Process for the upgrading of heavy cracking residues by hydrogenation
US3873440A (en) * 1973-11-14 1975-03-25 Universal Oil Prod Co Startup method for exothermic catalytic reaction zones
US3969222A (en) * 1974-02-15 1976-07-13 Universal Oil Products Company Hydrogenation and hydrodesulfurization of hydrocarbon distillate with a catalytic composite
US5059732A (en) * 1988-03-23 1991-10-22 Institut Francais Du Petrol Process for selective catalytic hydrogenation in liquid phase of a normally gaseous feed containing ethylene, acetylene and gasoline
US6090270A (en) * 1999-01-22 2000-07-18 Catalytic Distillation Technologies Integrated pyrolysis gasoline treatment process
US20160102258A1 (en) * 2014-10-10 2016-04-14 Uop Llc Process and apparatus for selectively hydrogenating naphtha
EP3060627A4 (en) * 2013-10-25 2017-05-31 Uop Llc Pyrolysis gasoline treatment process
EP3060628A4 (en) * 2013-10-25 2017-06-07 Uop Llc Pyrolysis gasoline treatment process
US10822555B2 (en) 2015-04-15 2020-11-03 IFP Energies Nouvelles Method for sweetening an olefinic petrol of sulphide-type compounds

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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DE2512714C2 (de) * 1975-03-22 1984-05-24 Ainslie Old Trafford Manchester Walthew Zündspule für eine Brennkraftmaschine
US4097370A (en) * 1977-04-14 1978-06-27 The Lummus Company Hydrotreating of pyrolysis gasoline
US4110202A (en) * 1977-11-18 1978-08-29 Uop Inc. Hydrogenation process for pyrolysis liquids
US4295499A (en) * 1978-12-12 1981-10-20 Kabushiki Kaisha Toyoda Jidoshokki Seisakusho Detection of weft in shuttleless loom
FR2473542B1 (fr) * 1980-01-12 1986-04-11 Jgc Corp Procede pour desulfurer et raffiner des fractions d'hydrocarbures contenant des quantites importantes de constituants aromatiques
US4342070A (en) * 1980-03-18 1982-07-27 Emhart Industries, Inc. Anchoring apparatus for an electrical device
EP0582723A1 (de) * 1992-08-04 1994-02-16 NEUMANN + STALLHERM GmbH Verfahren zur Aufbereitung von Rohbenzol
FR2753717B1 (fr) * 1996-09-24 1998-10-30 Procede et installation pour la production d'essences de craquage catalytique a faible teneur en soufre
DK29598A (da) * 1998-03-04 1999-09-05 Haldor Topsoe As Fremgangsmåde til afsvovlning af FCC-tung benzin

Citations (5)

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Publication number Priority date Publication date Assignee Title
US3133013A (en) * 1961-01-23 1964-05-12 Universal Oil Prod Co Hydrorefining of coke-forming hydrocarbon distillates
US3161586A (en) * 1962-12-21 1964-12-15 Universal Oil Prod Co Hydrorefining of coke-forming hydrocarbon distillates
US3221078A (en) * 1961-07-06 1965-11-30 Engelhard Ind Inc Selective hydrogenation of olefins in dripolene
US3239454A (en) * 1963-01-14 1966-03-08 Socony Mobil Oil Co Selective multistage hydrogenation of hydrocarbons
US3388055A (en) * 1966-04-15 1968-06-11 Air Prod & Chem Catalytic hydrogenation of unsaturated hydrocarbons

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3494859A (en) * 1967-06-07 1970-02-10 Universal Oil Prod Co Two-stage hydrogenation of an aromatic hydrocarbon feedstock containing diolefins,monoolefins and sulfur compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3133013A (en) * 1961-01-23 1964-05-12 Universal Oil Prod Co Hydrorefining of coke-forming hydrocarbon distillates
US3221078A (en) * 1961-07-06 1965-11-30 Engelhard Ind Inc Selective hydrogenation of olefins in dripolene
US3161586A (en) * 1962-12-21 1964-12-15 Universal Oil Prod Co Hydrorefining of coke-forming hydrocarbon distillates
US3239454A (en) * 1963-01-14 1966-03-08 Socony Mobil Oil Co Selective multistage hydrogenation of hydrocarbons
US3388055A (en) * 1966-04-15 1968-06-11 Air Prod & Chem Catalytic hydrogenation of unsaturated hydrocarbons

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3764521A (en) * 1971-10-18 1973-10-09 Dow Chemical Co Process for the upgrading of heavy cracking residues by hydrogenation
US3873440A (en) * 1973-11-14 1975-03-25 Universal Oil Prod Co Startup method for exothermic catalytic reaction zones
US3969222A (en) * 1974-02-15 1976-07-13 Universal Oil Products Company Hydrogenation and hydrodesulfurization of hydrocarbon distillate with a catalytic composite
US5059732A (en) * 1988-03-23 1991-10-22 Institut Francais Du Petrol Process for selective catalytic hydrogenation in liquid phase of a normally gaseous feed containing ethylene, acetylene and gasoline
US6090270A (en) * 1999-01-22 2000-07-18 Catalytic Distillation Technologies Integrated pyrolysis gasoline treatment process
WO2000043467A1 (en) * 1999-01-22 2000-07-27 Catalytic Distillation Technologies Integrated pyrolysis gasoline treatment process
EP3060627A4 (en) * 2013-10-25 2017-05-31 Uop Llc Pyrolysis gasoline treatment process
EP3060628A4 (en) * 2013-10-25 2017-06-07 Uop Llc Pyrolysis gasoline treatment process
US20160102258A1 (en) * 2014-10-10 2016-04-14 Uop Llc Process and apparatus for selectively hydrogenating naphtha
US9822317B2 (en) * 2014-10-10 2017-11-21 Uop Llc Process and apparatus for selectively hydrogenating naphtha
US10822555B2 (en) 2015-04-15 2020-11-03 IFP Energies Nouvelles Method for sweetening an olefinic petrol of sulphide-type compounds

Also Published As

Publication number Publication date
FR2104631A1 (enrdf_load_stackoverflow) 1972-04-21
GB1236341A (en) 1971-06-23
CA923062A (en) 1973-03-20
DE1931952A1 (de) 1971-01-07
FR2104631B1 (enrdf_load_stackoverflow) 1973-12-07
DE1931952B2 (de) 1973-02-15

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