EP0099951A1 - Verfahren zum Dehalogenieren von organischen halogenierten Verbindungen - Google Patents

Verfahren zum Dehalogenieren von organischen halogenierten Verbindungen Download PDF

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Publication number
EP0099951A1
EP0099951A1 EP82306974A EP82306974A EP0099951A1 EP 0099951 A1 EP0099951 A1 EP 0099951A1 EP 82306974 A EP82306974 A EP 82306974A EP 82306974 A EP82306974 A EP 82306974A EP 0099951 A1 EP0099951 A1 EP 0099951A1
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EP
European Patent Office
Prior art keywords
oil
sodium
organic halide
dispersion
particles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP82306974A
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English (en)
French (fr)
Inventor
James S. Ferrie
Jean-Marie Braun
John W. Hanis
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Ontario Hydro
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Ontario Hydro
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Filing date
Publication date
Application filed by Ontario Hydro filed Critical Ontario Hydro
Publication of EP0099951A1 publication Critical patent/EP0099951A1/de
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/34—Dehalogenation using reactive chemical agents able to degrade
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/32—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by treatment in molten chemical reagent, e.g. salts or metals
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/22—Organic substances containing halogen

Definitions

  • PCB Polychlorinated biphenyls
  • This invention relates to a process for the dehalogenation (destruction) of polychlorinated biphenyls and polychlorinated benzenes such as are found in electrical insulating oils contaminated with compounds generically classified as askarels.
  • the process of the invention can also be used to decontaminate PCB contaminated solid wastes using oil as a solvent and/or for the destruction of concentrated PCB waste liquids by dilution in oil.
  • the process disclosed hereinafter may more generally be applied to the dehalogenation and destruction of organic halides including hazardous halogenated wastes such as organic halide-containing wood preservatives and pesticides.
  • chlorobiphenyl may be reacted with metallic sodium, in the form of sodium wire or ribbon, under ice cold conditions or with gentle warming, in the presence of ethyl carbonate or ethyl benzoate, with or without additions of benzene, to obtain low or medium yields of biphenylcarbinols.
  • organic halides dissolved in hydrocarbon-based oils may be effectively dehalogenated at temperatures ranging from about 100°C up to about 160°C by maintaining the solution under agitation in a mixture with a fine dispersion of molten sodium particles of which at least 80% are below 10 microns particle size, whereby the organic halide groups are reduced to sodium halide.
  • the fine dispersion of molten sodium particles is formed by pre-dispersing metallic sodium under vigorous agitation in a relatively smaller quantity of a hydrocarbon-based oil the same as or compatible with the oil to be treated, at a temperature above the melting point of sodium and preferably in the range 105°C to 160°C, and the pre-dispersion is added to the bulk of the oil containing the organic halide to be dehalogenated.
  • the process is also applicable to other hydrocarbon-based oils such as turbine oils and crankcase oils.
  • other hydrocarbon-based oils such as turbine oils and crankcase oils.
  • the treatment is accompanied by a significant increase in viscosity which renders the application of the process more difficult.
  • the organic halides In order to obtain a satisfactory degree of dehalogenation of the organic halides, it has been found necessary to react the organic halides with a very fine dispersion of molten sodium particles.
  • this very fine dispersion at least 80% of the sodium particles should be below 10 microns particle size. More preferably, at least 90% of the particles should be below about 10 microns and at least about 65% should be less than 5 microns particle size.
  • These very fine dispersions are best prepared by pre-dispersing sodium at temperatures above its melting point in a relatively smaller volume of the oil to be treated, or an oil compatible therewith and which will not render the eventual product unusable for its intended purpose.
  • the resulting very fine dispersion is then blended with a larger volume of contaminated oil, in order to provide a reaction mixture containing a desired ratio of sodium to reducible organic halide.
  • lump metallic sodium or liquid metallic sodium is added to dried oil in a quantity sufficient to yield a dispersion containing about 5 to 50% by weight sodium.
  • the use of less than about 5% by weight sodium is usually inefficient, as then greater quantities of the pre-dispersion are required to achieve the desired molar ratios of sodium to reducible halogen, while with quantities of sodium much greater than about 50%, it is difficult to achieve a satisfactory dispersion.
  • a weight of sodium sufficient to achieve an about 30% concentration is employed.
  • the oil in which the pre-dispersion is to be formed may be a fresh, uncontaminated oil, or may be oil which is contaminated with organic halide material. Desirably, in order to avoid excessive wastage of sodium, the oil is substantially dry and, if necessary, it is pre-dried either by heating or by vacuum degassification so that its moisture content is less than about 100 mg/kg. During the formation of the pre-dispersion, the oil is maintained at a temperature above the melting point of liquid sodium, preferably in the range 105°C to 160°C.
  • the dispersion is formed at a temperature of about 120°C.
  • the vessel in which the dispersion is formed, and all other vessels and processing equipment subsequently employed in the process with which the metallic-sodium- containing mixtures come into contact, are desirably formed or are lined with materials inert with respect to liquid sodium e.g. mild steel, stainless steel, or glass.
  • the mixture of sodium and oil is subjected to vigorous agitation for a period sufficient to produce a fine sodium dispersion of the required particle size distribution.
  • the particle size distribution of the resulting dispersion can be readily determined using conventional optical particle counter apparatus, for example a HI-AC (Trade Mark) machine and the conditions of agitation and period of time required to produce the desired particle size distribution can be readily determined in any given case by trial and experiment.
  • HI-AC Trade Mark
  • a top drive impeller equipped with either a Cowles Dissolver (Trade Mark) head or a Premier Mill Dispersator (Trade Mark) head may be used.
  • oils to be treated by the present process are contaminated electrical insulating oils.
  • electrical insulating oils are well understood by those skilled in the art, and one skilled in the art can readily determine whether or not a given oil is an electrical insulating oil.
  • electrical insulating oil refers to mineral electrical insulating oils of petroleum origin for use as insulating and cooling media in electrical power and distribution apparatus such as transformers, regulators, reactors, circuit breakers, switch gear, and attendant equipment.
  • electrical insulating oil should conform to the specifications set out in Table 1, as determined by the relevant ASTM test procedures.
  • the oils employed in the present process conform to these specifications.
  • a further example of a class of oils which may be treated by the present process is turbine oil.
  • These are usually sulfur-free mineral oils of petroleum origin employed as a lubricant medium in steam turbines, electrical generators and other rotating equipment systems.
  • the turbine oils conform to the specifications set out in Table 2.
  • crankcase oil i.e. oil used as internal combustion engine lubricant.
  • these conform to the specifications set out in Table 3.
  • PCB-contaminated electrical insulating oil or other hydrocarbon-based oil to be treated is stored in a storage vessel 10 from which it is transferred by a pump P 1 along a line 11 to an enclosed reactor vessel 12 preferably of steel.
  • the vessel 12 is equipped with a low speed impeller 13, heaters 14, and an exhaust condenser 16.
  • a line 17 is provided connected to a cylinder 18 of nitrogen or other inert gas which is slowly bubbled into the mixture to exclude air and form a blanket of inert gas to reduce losses of the subsequently-introduced sodium through oxidation.
  • the condenser 16 removes organic vapours from the exhaust nitrogen or other inert gas.
  • the oil in the storage vessel 10 is desirably pre-dried, if necessary, to less than 100 mg/kg water either by heating or by vacuum degassification.
  • the pre-dispersion, prepared as described above is introduced into the reactor through a line 19.
  • the oil contained within the reactor vessel 12 is heated to a temperature in the range of 100 - 160°C.
  • the reaction times needed for substantially complete reduction of the organic halide groups to sodium halide tend to be excessively long, and there is a risk of the liquid sodium particles tending to agglomerate together to form agglomerated masses.
  • the dispersion of sodium particles should remain in the form of dispersed particles of fine particle size, as with particles of greater size, the reaction is much less effective. Without wishing to be bound by any theory, it is believed that the reduction in the rate and efficiency of the dehalogenation process with particles of increased size is due to the coating of such large particles by reaction products thus hindering or preventing further reaction.
  • the dehalogenation process is much less effective.
  • the use of a dispersion such that at least 80% of the particles are below 10 microns particle size, more preferably with at least about 50% of the particles below about 5 microns particle size, is a highly important factor in obtaining a satisfactory dehalogenation reaction.
  • the oil the reactor vessel should not be heated to temperatures much in excess of about 160°C, as at higher temperatures there is increased risk of degradation of the oil through thermal cracking and oxidation.
  • the reaction mixture is maintained at a temperature of about 110°C to about 130°C.
  • the dispersion Sufficient of the dispersion is added through the line 19 to the volume of oil contained in the reactor 12 to provide in the reaction mixture a molar ratio of sodium to reducible chlorine in the range about 2:1 to 30:1. Below this range of sodium contents, satisfactory dehalogenation is not likely to be achieved, while contents of sodium higher than the above mentioned range do not appear to add to the effectiveness of the reaction and merely result in excessive consumption of sodium.
  • the molar ratio of sodium to reducible halogen is in the range about 4:1 to about 8:1.
  • oil solution containing greater than 10% by weight of dissolved halogenated species can be treated by the present process, greater quantities of the sodium dispersion need to be added to the oil and this may render it more difficult to maintain intimate mixing of the stirred reaction mixture. It is therefore normally preferred to employ oils containing no more than about 10% by weight dissolved halogenated species.
  • the oil can be substantially wholly dehalogenated to achieve final concentrations of organic halide species of less than about 5 mg/kg, more usually less than about 2 mg/kg within about 15 to 240 minutes. In the preferred form, the dehalogenation is complete in less than about 30 minutes.
  • the reaction mixture is pumped by a pump P 2 along a line 21 to a solids-liquids separator device, for example a centrifuge C 1 .
  • a centrifuge capable of maintaining a minimum relative centrifugal force of 210 G at the periphery of the centrifugal plates is employed.
  • the solids i.e. unreacted sodium, suspended reaction products and sludges are removed from the oil.
  • the removed solids are passed along a line 22 and are collected in a collection vessel 23. If desired, the solids collected in the vessel 23 may be subjected to a conventional treatment for recovery of metallic sodium therefrom before being disposed of as waste.
  • the liquids separated at the centrifuge C 1 may be passed along line 25 to a quenching vessel 24 where any remaining traces of sodium are quenched with water introduced through a line 26. If the oil has not cooled sufficiently through its passage through the centrifuge C 1 , it is permitted to cool below about 95°C before contact with the water, to avoid excessively vigorous reaction.
  • the mixture of oil and water is maintained under agitation by a stirrer 27, and the oil is washed free of any remaining traces of sodium and of soluble reaction products such as sodium halide and sodium soaps of acidic oil components.
  • the oil and water mixture is pumped by a pump P 3 along a line 28 to a further centrifuge C 2 where the heavier water phase is separated from the oil and collected in a waste water collection vessel 29.
  • the oil phase may be subjected to further washing stages and in such case is passed successively through a series of washing tanks, similar to the quenching tank 24, where the oil phase is mixed with water, and the oil-water mixture from each tank is passed through a centrifuge similar to the centrifuge C 2 before passing to the subsequent washing tank.
  • a single tank 24 for quenching and washing, and centrifuge C 2 are sufficient for all washing stages if the oil phase is returned to the washing tank 24 through a return line after passing through centrifuge C 2 .
  • the oil may be washed with a total volume of water approximately equal to that of the volume of the oil, and the washing may be conducted in 3 to 5 separate stages.
  • the first washing stage in the tank 24 is desirably performed under a blanket of inert gas supplied along line 31 from the inner gas container 18, or may be conducted under copious air flow, to ensure that any hydrogen evolved in the reaction of sodium with water in the tank 24 is diluted to less than the lower explosive limit for hydrogen, more preferably to less than about one-fifth the lower explosive limit.
  • the mixture may instead be allowed to settle into distinct oil and water phases and the oil phase pumped off.
  • the gases evolved from the reactor vessel 12 and the quenching vessel 24 (mainly inert gas containing some hydrogen) are collected beneath exhaust hoods 32 and may be vented to the atmosphere.
  • the washed oil is substantially free of halogen and halogenated compounds, but contains some dissolved water.
  • the oil can be dried by pumping it by a pump P 4 along a line 36 and filtering it through blotter type paper in a filter press 37 or by vacuum drying.
  • the dried oil is collected in a vessel 38. If necessary or desirable, the quality of the oil product may be further improved by filtering it through a column of activated clay to remove trace impurities.
  • the process described above may be modified by eliminating the quenching, water-washing and drying steps, without affecting the quality of the product if the solids separation step is carried out efficiently. In such case, any remaining sodium or suspended solids present in the product can be removed by activated clay treatment.
  • 25 g of lump sodium metal at 23°C is added to the stainless steel mixing bowl of a 1 L capacity Waring Blender containing 300 g of an electrical insulating oil meeting standard specifications for new electrical insulating oil.
  • the oil is at a temperature of 120°C.
  • a nitrogen gas flow of approximately 60 ml/min is established over the oil to provide an inert atmosphere, preventing oxidation of highly reactive sodium and the mixture is blended for 15 minutes at a controlled temperature of 122.5 ⁇ 2.5°C and impeller speed of 20,000 RPM.
  • the resulting mixture is a uniformly grey dispersion of spherical particles with particle size distributed as shown in Table 4.
  • the concentration of sodium in oil may be varied from about 5% to about 50% by weight.
  • Freshly prepared sodium dispersion prepared as described in Example 1 is used to dechlorinate several chlorinated compounds, intimately mixed with insulating oil, in a 1 L glass reactor consisting of a standard 3-necked flask equipped with a sealed stirrer, nitrogen gas input/output connections, four equally spaced 1/2" glass baffles and an electric heating mantle. Reaction conditions and results for a variety of dechlorinations are given in Table 5.
  • the dechlorination was conducted on an oil sample containing an oxidation inhibitor, showing that the presence of oxidation inhibitor does not interfere with the dechlorination process.
EP82306974A 1982-07-27 1982-12-24 Verfahren zum Dehalogenieren von organischen halogenierten Verbindungen Withdrawn EP0099951A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA000408116A CA1181771A (en) 1982-07-27 1982-07-27 Process for dehalogenation of organic halides
CA408116 1982-07-27

Publications (1)

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EP0099951A1 true EP0099951A1 (de) 1984-02-08

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JP (1) JPS5920179A (de)
CA (1) CA1181771A (de)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0225849A1 (de) * 1985-12-06 1987-06-16 Ciba-Geigy Ag Verfahren zur Enthalogenierung von halogenierten aliphatischen und aromatischen Verbindungen
US5141629A (en) * 1990-05-15 1992-08-25 State Of Israel, Atomic Energy Commission Process for the dehalogenation of organic compounds
EP0503831A1 (de) * 1991-03-15 1992-09-16 Ontario Hydro Vernichtung polychlorierter Biphenyle
WO1994003237A1 (en) * 1992-08-06 1994-02-17 Ea Technology Limited A process for the destruction of halocarbons
EP0595079A1 (de) * 1992-10-28 1994-05-04 Degussa Aktiengesellschaft Verfahren zur Umsetzung von FCKW's mit Dispersionen von Alkalimetallen
WO1994014731A1 (en) * 1992-12-23 1994-07-07 Commonwealth Scientific And Industrial Research Organisation Destruction of halide containing organics and solvent purification
GB2281305A (en) * 1993-08-27 1995-03-01 John Robson Metals Limited Removing chlorinated organic compounds from oil
WO1995018652A1 (en) * 1994-01-04 1995-07-13 Neos Technology Inc. Sodium dispersion and organohalide reaction processes
US5490919A (en) * 1990-08-14 1996-02-13 State Of Isreal, Atomic Energy Commission Process for the dehalogenation of organic compounds
WO1997000928A1 (fr) * 1995-06-22 1997-01-09 Bernard Chavet Procede de raffinage d'huiles usagees par traitement alcalin
AU676881B2 (en) * 1992-12-23 1997-03-27 Hydrodec Development Corporation Pty Ltd Destruction of halide containing organics and solvent purification
US5951852A (en) * 1993-12-23 1999-09-14 Commonwealth Scientific And Industrial Research Organisation Et Al. Destruction of halide containing organics and solvent purification
ES2183701A1 (es) * 2001-01-08 2003-03-16 Ecolsir Srl Procedimiento para la deshalogenacion y regeneracion de aceites minerales dielectricos y diatermicos contaminados por compuestos organicos clorados y/o sulfurados, por compuestos organicos metalicos y por compuestos acidos de oxidacion.
DE102019121656A1 (de) * 2019-08-12 2021-02-18 Ors Oil Recycling Solutions Gmbh Verfahren und Vorrichtung zum Aufarbeiten von PCB- und/oder PAK-haltigem Öl

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1296744C (en) * 1988-03-18 1992-03-03 Derek J. Mcphee Dehalogenation of halogenated aromatic compounds
JP2611900B2 (ja) * 1992-06-05 1997-05-21 財団法人生産開発科学研究所 炭化水素油よりハロゲン化芳香族化合物を除去する方法
JP3247505B2 (ja) * 1993-06-24 2002-01-15 財団法人生産開発科学研究所 ハロゲン化芳香族化合物を分解する方法
JP3247543B2 (ja) 1994-04-22 2002-01-15 財団法人生産開発科学研究所 ハロゲン化芳香族化合物のアルカリ分解方法
JP5254512B2 (ja) * 2001-09-26 2013-08-07 日本曹達株式会社 有機塩素化合物の脱塩素化処理装置及びそれを用いた処理法
JP4746886B2 (ja) * 2005-02-10 2011-08-10 日本曹達株式会社 アルカリ金属分散体の製造方法
JP5717294B2 (ja) * 2011-09-08 2015-05-13 中国電力株式会社 ハロゲン化合物含有油の無害化処理装置
JP2013056066A (ja) * 2011-09-08 2013-03-28 Chugoku Electric Power Co Inc:The ハロゲン化合物含有油の無害化処理方法及び無害化処理装置
JP5717293B2 (ja) * 2011-09-08 2015-05-13 中国電力株式会社 ハロゲン化合物含有油の無害化処理装置
JP5615781B2 (ja) * 2011-09-08 2014-10-29 中国電力株式会社 ハロゲン化合物含有油の無害化処理方法及び無害化処理装置
CN104845663A (zh) * 2015-03-27 2015-08-19 北京燕联化工技术有限公司 一种油品高效脱氯剂及油品脱氯方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2302335A1 (fr) * 1975-02-28 1976-09-24 Schmids Erben Ag Adolf Procede de traitement d'huiles minerales usagees
GB2017143A (en) * 1978-03-25 1979-10-03 Degussa Process for regenerating spent lubricating oils
DE2940630A1 (de) * 1979-10-06 1981-04-09 Degussa Ag, 6000 Frankfurt Verfahren zur wiederaufbereitung von gebrauchten schmieroelen
GB2063908A (en) * 1979-11-30 1981-06-10 Sunohio Method of destruction of polyhalogenated biphenyls
GB2082625A (en) * 1980-08-25 1982-03-10 Sunohio A method for the destruction of polyhalogenated biphenyl compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2302335A1 (fr) * 1975-02-28 1976-09-24 Schmids Erben Ag Adolf Procede de traitement d'huiles minerales usagees
GB2017143A (en) * 1978-03-25 1979-10-03 Degussa Process for regenerating spent lubricating oils
DE2940630A1 (de) * 1979-10-06 1981-04-09 Degussa Ag, 6000 Frankfurt Verfahren zur wiederaufbereitung von gebrauchten schmieroelen
GB2063908A (en) * 1979-11-30 1981-06-10 Sunohio Method of destruction of polyhalogenated biphenyls
GB2082625A (en) * 1980-08-25 1982-03-10 Sunohio A method for the destruction of polyhalogenated biphenyl compounds

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0225849A1 (de) * 1985-12-06 1987-06-16 Ciba-Geigy Ag Verfahren zur Enthalogenierung von halogenierten aliphatischen und aromatischen Verbindungen
US5141629A (en) * 1990-05-15 1992-08-25 State Of Israel, Atomic Energy Commission Process for the dehalogenation of organic compounds
US5490919A (en) * 1990-08-14 1996-02-13 State Of Isreal, Atomic Energy Commission Process for the dehalogenation of organic compounds
EP0503831A1 (de) * 1991-03-15 1992-09-16 Ontario Hydro Vernichtung polychlorierter Biphenyle
WO1994003237A1 (en) * 1992-08-06 1994-02-17 Ea Technology Limited A process for the destruction of halocarbons
EP0595079A1 (de) * 1992-10-28 1994-05-04 Degussa Aktiengesellschaft Verfahren zur Umsetzung von FCKW's mit Dispersionen von Alkalimetallen
WO1994014731A1 (en) * 1992-12-23 1994-07-07 Commonwealth Scientific And Industrial Research Organisation Destruction of halide containing organics and solvent purification
AU676881B2 (en) * 1992-12-23 1997-03-27 Hydrodec Development Corporation Pty Ltd Destruction of halide containing organics and solvent purification
GB2281305A (en) * 1993-08-27 1995-03-01 John Robson Metals Limited Removing chlorinated organic compounds from oil
US5951852A (en) * 1993-12-23 1999-09-14 Commonwealth Scientific And Industrial Research Organisation Et Al. Destruction of halide containing organics and solvent purification
WO1995018652A1 (en) * 1994-01-04 1995-07-13 Neos Technology Inc. Sodium dispersion and organohalide reaction processes
WO1997000928A1 (fr) * 1995-06-22 1997-01-09 Bernard Chavet Procede de raffinage d'huiles usagees par traitement alcalin
US6072065A (en) * 1995-06-22 2000-06-06 Chavet; Bernard Alkaline treatment method for refining used oils
ES2183701A1 (es) * 2001-01-08 2003-03-16 Ecolsir Srl Procedimiento para la deshalogenacion y regeneracion de aceites minerales dielectricos y diatermicos contaminados por compuestos organicos clorados y/o sulfurados, por compuestos organicos metalicos y por compuestos acidos de oxidacion.
DE102019121656A1 (de) * 2019-08-12 2021-02-18 Ors Oil Recycling Solutions Gmbh Verfahren und Vorrichtung zum Aufarbeiten von PCB- und/oder PAK-haltigem Öl

Also Published As

Publication number Publication date
CA1181771A (en) 1985-01-29
JPS5920179A (ja) 1984-02-01

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