NO174088B - PROCEDURE FOR DESTRUCTION OF CHLORED ORGANIC PRODUCTS AT LOW TEMPERATURE - Google Patents

PROCEDURE FOR DESTRUCTION OF CHLORED ORGANIC PRODUCTS AT LOW TEMPERATURE Download PDF

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NO174088B
NO174088B NO88880104A NO880104A NO174088B NO 174088 B NO174088 B NO 174088B NO 88880104 A NO88880104 A NO 88880104A NO 880104 A NO880104 A NO 880104A NO 174088 B NO174088 B NO 174088B
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bath
products
chloraluminate
chlorinated
organic products
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NO88880104A
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NO880104D0 (en
NO880104L (en
NO174088C (en
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Jacques Dugua
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Atochem
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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
    • A62D3/32—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

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
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Abstract

1. Process for destroying chlorinated organic products containing more than 2 carbon atoms, in which these products are brought into contact with a bath of at least one chloroaluminate, characterized in that the initial concentration of the chlorinated organic products in the bath is 4000 ppm or less and preferably 2000 ppm or less.

Description

Foreliggende oppfinnelse angår en fremgangsmåte for destruering av klorerte organiske produkter og mere spesielt aromatiske produkter og polyklorbifenyler. The present invention relates to a method for destroying chlorinated organic products and more particularly aromatic products and polychlorinated biphenyls.

Visse flytende dielektrika inneholder klorerte organiske produkter og etter en viss brukstid brytes de ned og må erstattes. Man kan enkelte ganger regenerere dem totalt eller delvis. Man er imidlertid tvunget til å ødelegge en del av disse væsker. Certain liquid dielectrics contain chlorinated organic products and after a certain period of use they break down and must be replaced. They can sometimes be completely or partially regenerated. However, one is forced to destroy a part of these liquids.

Klorerte organiske produkter samt visse pesticider, klorerte aromater som heksaklorbenzen eller polyklorbifenyler, PCB, kan gi giftige produkter når de brennes som et vanlig brenn-bart produkt. Chlorinated organic products as well as certain pesticides, chlorinated aromatics such as hexachlorobenzene or polychlorobiphenyls, PCBs, can produce toxic products when burned as a normal combustible product.

For å unngå å danne toksiske produkter ødelegges disse produkter ved høy temperatur og under spesifikke betingelser. To avoid forming toxic products, these products are destroyed at high temperature and under specific conditions.

En artikkel i "SCI. TOTAL ENVIRON" 1978, 10 (1) 51-9 beskriver destruering av polyklorbifenyler, PCB, ved forbrenning med en oppholdstid på over 2 sekunder. An article in "SCI. TOTAL ENVIRON" 1978, 10 (1) 51-9 describes the destruction of polychlorinated biphenyls, PCBs, by combustion with a residence time of over 2 seconds.

En annen artikkel "PROC. ANNU MEET - AIR POLLUT. CONTROL ASSOC." 1977 (Vol 2) nr. 33 beskriver en destruering av 99,9995$ PCB ved 1000°C med en oppholdstid på 2 sekunder. Another article "PROC. ANNU MEET - AIR POLLUT. CONTROL ASSOC." 1977 (Vol 2) No. 33 describes a destruction of 99.9995$ PCB at 1000°C with a residence time of 2 seconds.

EP-PS 170 714 beskriver destruering av PCB ved omsetning med smeltet aluminium eller et autektikum på basis av aluminium der reaksjonen skjer ved over 382°C. EP-PS 170 714 describes the destruction of PCBs by reaction with molten aluminum or an autectic based on aluminum where the reaction takes place at over 382°C.

Man har nu funnet en fremgangsmåte som er adskillig enklere for å destruere disse produkter og som kan arbeide under 300°C. A method has now been found which is much simpler to destroy these products and which can work below 300°C.

Foreliggende oppfinnelse angår i henhold til dette en fremgangsmåte for destruering av klorerte organiske produkter med mer enn 2 karbonatomer hvor man bringer produktene i kontakt med et bad av minst et kloraluminat, og fremgangsmåten karakteriseres ved at begynnelses-konsentrasjonen av klorerte organiske produkter i badet er under 5000 ppm og fortrinnsvis under 200 ppm, beregnet på kloraluminatet, og at temperaturen i badet er under 300°C. According to this, the present invention relates to a method for destroying chlorinated organic products with more than 2 carbon atoms, where the products are brought into contact with a bath of at least one chloraluminate, and the method is characterized by the initial concentration of chlorinated organic products in the bath being below 5000 ppm and preferably below 200 ppm, calculated on the chloraluminate, and that the temperature in the bath is below 300°C.

Man kan benytte forskjellige kloraluminater eller disse blandinger. For eksempel kan nevnes kloraluminatene av kalium, litium, natrium, kalsium, strontium eller ammonium. Different chloraluminates or mixtures of these can be used. For example, the chloroaluminates of potassium, lithium, sodium, calcium, strontium or ammonium can be mentioned.

I foreliggende beskrivelse kalles et kloraluminat en hvilken som helst blanding av vannfri aluminiumklorid og ett eller flere metallklorider. In the present description, a chloroaluminate is any mixture of anhydrous aluminum chloride and one or more metal chlorides.

Kloraluminatet av natrium, det mest foretrukne, angir en blanding av aluminiumklorid og natriumklorid i hvilke som helst andeler og ikke bare den ekvimolekylære blanding. Kloraluminatet av natrium kan også inneholde litiumklorid og/eller kaliumklorid. Man kan således ha en hvilken som helst blanding av aluminiumklorid, natriumklorid og litiumklorid som så kalles kloraluminatet av natrium og litium. The chloroaluminate of sodium, the most preferred, denotes a mixture of aluminum chloride and sodium chloride in any proportion and not just the equimolecular mixture. The chloraluminate of sodium may also contain lithium chloride and/or potassium chloride. You can thus have any mixture of aluminum chloride, sodium chloride and lithium chloride, which is then called the chloroaluminate of sodium and lithium.

Man foretrekker også at kloraluminatet av natrium inneholder minst 50 mol-% aluminiumklorid og oppviser et smeltepunkt på under 200°C. It is also preferred that the chloroaluminate of sodium contains at least 50 mol% aluminum chloride and exhibits a melting point of less than 200°C.

Oppfinnelsen finner spesiell anvendelse på klorerte organiske produkter med mer enn 2 karbonatomer men kan også brukes på alifatiske, cykliske, aromatiske mono- eller polycykliske eller heterocykliske produkter. Oppfinnelsen finner helt spesielt anvendelse på perklorerte alifatiske produkter og blant de aromatiske, polyklorbifenylene. The invention finds particular application to chlorinated organic products with more than 2 carbon atoms but can also be applied to aliphatic, cyclic, aromatic mono- or polycyclic or heterocyclic products. The invention is particularly applicable to perchlorinated aliphatic products and among the aromatic polychlorobiphenyls.

Mengden klorert organisk produkt som skal destrueres ligger fortrinnsvis under 5.000 ppm av kloraluminatet og fortrinnsvis under 2.000 ppm. The amount of chlorinated organic product to be destroyed is preferably below 5,000 ppm of the chloraluminate and preferably below 2,000 ppm.

Produktene kan foreligge i en hvilken som helst form. De kan spesielt befinne seg i fast fase, for eksempel absorbert på aktivkull. The products can be in any form. They can especially be in the solid phase, for example absorbed on activated carbon.

Fremgangsmåten ifølge oppfinnelsen består i å bringe det klorerte produkt i kontakt med kloraluminatbadet. The method according to the invention consists in bringing the chlorinated product into contact with the chloraluminate bath.

Når det klorerte produkt befinner seg i fast fase kan man bringe denne faste fase inn i et fortrinnsvis omrørt kloraluminatbad. Man passer på å holde badet smeltet, eventuelt ved oppvarming. Man arbeider på samme måte hvis de klorerte produkter befinner seg i flytende fase. Som oftest er de klorerte produkter som man søker å ødelegge i gassfase, alene eller i blanding med lettere klorerte produkter og/eller bærergasser. When the chlorinated product is in solid phase, this solid phase can be brought into a preferably stirred chloraluminate bath. Care is taken to keep the bath melted, possibly by heating. You work in the same way if the chlorinated products are in the liquid phase. Most often, the chlorinated products that are sought to be destroyed are in gas phase, alone or in a mixture with lighter chlorinated products and/or carrier gases.

For eksempel kan det være en gass som stammer fra en forbrenning, man har da kvikksølv inneholdende karbonholdig gass, karbonoksyd, klorerte produkter og eventuelt oksygen, men det kan imidlertid dreie seg om en hvilken som helst gassformig blanding, oppnådd fra en hvilken som helst f remgangsmåte. For example, it can be a gas originating from combustion, one then has mercury containing carbonaceous gas, carbon oxide, chlorinated products and possibly oxygen, but it can however be any gaseous mixture, obtained from any f method of walking.

Man foretrekker at de klorerte produkter befinner seg i vannfri fase. Gassen inneholdende de klorerte produkter kan tørkes ved kontakt med et absorbsjonsmiddel som for eksempel aluminium eller glykol. It is preferred that the chlorinated products are in the anhydrous phase. The gas containing the chlorinated products can be dried by contact with an absorbent such as aluminum or glycol.

Deretter bringer man denne gassformige fase inneholdende de klorerte produkter som skal destrueres i kontakt med kloraluminatet på en hvilken som helst kontaktmåte for en flytende fase med en gassformig fase. Dette kan skje ved hjelp av en kolonne med plater eller fylling. Man kan videre i et omrørt bad av kloraluminat innføre den gassformige fase ved hjelp av en innblåsningslanse eller via et rør som munner i bunnen av badet. This gaseous phase containing the chlorinated products to be destroyed is then brought into contact with the chloroaluminate in any contact manner for a liquid phase with a gaseous phase. This can be done using a column of plates or filling. You can further introduce the gaseous phase into a stirred bath of chloraluminate by means of a blow-in lance or via a pipe that opens at the bottom of the bath.

De forskjellige organiske klorerte produkter kan skille seg mellom flytende fase og damp i kloraluminatbadet. Det samme gjelder produktene som følger med de klorerte produkter. Man kan benytte en plate- eller fylt kolonne for å sikre en sirkulasjon og en kontinuerlig oppfanging av en flytende og gassfase og en god kontakt mellom de gassformige produkter og kloraluminatbadet. Man kan videre arbeide med en kaskade av omrørte reaktorer. Man opprettholder de organiske klorerte produkter i kontakt med kloraluminatbadet i det tidsrom som er nødvendig for destrueringen. Oppholdstiden kan variere innen vide grenser men ligger generelt mellom noen minutter og noen timer. The various organic chlorinated products can separate between liquid phase and vapor in the chloraluminate bath. The same applies to the products that come with the chlorinated products. A plate or packed column can be used to ensure circulation and continuous capture of a liquid and gas phase and a good contact between the gaseous products and the chloraluminate bath. You can also work with a cascade of stirred reactors. The organic chlorinated products are maintained in contact with the chloraluminate bath for the time required for destruction. The residence time can vary within wide limits, but is generally between a few minutes and a few hours.

Videre kan man arbeide ved en hvilken som helst temperatur forutsatt at kloraluminatbadet er flytende, man foretrekker å arbeide under 300 og helst mellom 200 og 300°C. Furthermore, one can work at any temperature provided that the chloraluminate bath is liquid, one prefers to work below 300 and preferably between 200 and 300°C.

Destrueringshastigheten for de klorerte produkter og spesielt dé aromatiske, øker med kloraluminatbadets temperatur. The destruction rate for the chlorinated products and especially the aromatic ones increases with the temperature of the chloraluminate bath.

Man kan i gassfasen til kloraluminatbadet finne lette klorerte dekomponeringsprodukter som man ønsker å destruere; for eksempel karbontetraklorid og/eller heksakloretan. Man gjenfinner ikke i dampfasen til kloraluminatbadet de klorerte organiske produkter man søker å destruere. Når man analy-serer kloraluminatbadet etter å ha overholdt kontakttiden mellom de klorerte produkter og kloraluminat, gjenfinner man ikke de organiske produkter man har søkt å destruere. In the gas phase of the chloraluminate bath, you can find light chlorinated decomposition products that you want to destroy; for example carbon tetrachloride and/or hexachloroethane. The chlorinated organic products you seek to destroy are not found in the vapor phase of the chloraluminate bath. When you analyze the chloraluminate bath after observing the contact time between the chlorinated products and chloraluminate, you do not find the organic products that you tried to destroy.

Man kan videre periodisk spyle kloraluminatbadet for å unngå akkumulering av uoppløselige produkter der disse ikke kan forbli i suspensjon i badet. Ved denne spyling gjenfinner man heller ikke spor av de klorerte organiske produkter. Man kan således fastslå at de klorerte produkter man har ønsket å fjerne, er borte. You can also periodically flush the chloraluminate bath to avoid the accumulation of insoluble products where these cannot remain in suspension in the bath. With this flushing, traces of the chlorinated organic products are also not found. You can thus determine that the chlorinated products you wanted to remove are gone.

I en foretrukket gjennomførelsesform av oppfinnelsen til-settes det til kloraluminatbadet ett eller flere pulver-formige metaller valgt blant reduserende metaller som for eksempel aluminium eller sink. Man foretrekker å benytte et pulver hvis midlere granulometri ligger under 500 pm. Hvis man benytter metaller fjernes totalt de klorerte organiske produkter som tidligere men med en sterkt øket hastighet i størrelsesorden flere ganger til flere titalls den tidligere hastighet. In a preferred embodiment of the invention, one or more powdered metals selected from reducing metals such as aluminum or zinc are added to the chloraluminate bath. It is preferred to use a powder whose average granulometry is below 500 pm. If metals are used, the chlorinated organic products are removed in total as before, but with a greatly increased speed, several times to tens of times the previous speed.

Man fastslår et forbruk av pulverformig metall (eller metaller) som kan bekrefte at klorider dannes ved å overta klor fra de klorerte organiske produkter under disses destruksjon. Det er ingen grense for den mengde metallpulver som kan innføres i kloraluminatet. Man foretrekker å benytte aluminium i pulverform, man kan benytte helt opp til 5 eller 10 vekt-$ pulverformig aluminium i kloraluminatbadet. Man fastslår at destruksjonshastigheten for klorerte produkter øker med mengden pulverformig aluminium og med temperaturen i kloraluminatbadet. Man foretrekker å omrøre badet slik at metallpulveret er godt dispergert. Det eller de metalliske klorider som dannes kan blandes med badet av kloraluminat og fordeles mellom flytende og gassfase. Man kan hvis nødvendig fjerne metallkloridene fra gassfasen og behandle disse med et hydroksyd som for eksempel natrium- eller kaliumhydroksyd. A consumption of powdered metal (or metals) is determined which can confirm that chlorides are formed by taking over chlorine from the chlorinated organic products during their destruction. There is no limit to the amount of metal powder that can be introduced into the chloraluminate. It is preferred to use aluminum in powder form, you can use up to 5 or 10 wt% of powdered aluminum in the chloraluminate bath. It is determined that the rate of destruction for chlorinated products increases with the amount of powdered aluminum and with the temperature in the chloraluminate bath. It is preferred to stir the bath so that the metal powder is well dispersed. The metallic chloride(s) that are formed can be mixed with the chloraluminate bath and distributed between liquid and gas phase. If necessary, the metal chlorides can be removed from the gas phase and treated with a hydroxide such as sodium or potassium hydroxide.

De følgende eksempler illusterer oppfinnelsen. The following examples illustrate the invention.

Eksempel 1 Example 1

I en pyrexkolbe på 1 1, oppvarmet elektrisk og utstyrt med skruerører på 300 omdr./min. innføres 500 g kloraluminat av natrium med et forhold AlCl3:NaCl = 1, beregnet på molbasis. In a 1 1 pyrex flask, heated electrically and fitted with screw stirrers at 300 rpm. introduce 500 g of sodium chloroaluminate with a ratio AlCl3:NaCl = 1, calculated on a molar basis.

Produktet oppvarmes til 200°C, omrøres og deretter innføres 0,2 g heksaklorbenzen og 0,1 g decaklorbisfenyl. Etter 1 time ved 200° C vaskes det smeltede bad i 15 min. med en mengde på 50 l/time N2 som så vaskes i en vasker med 100 ml heksan. The product is heated to 200°C, stirred and then 0.2 g of hexachlorobenzene and 0.1 g of decachlorobisphenyl are introduced. After 1 hour at 200° C, the molten bath is washed for 15 min. with a quantity of 50 l/hour N2 which is then washed in a washer with 100 ml of hexane.

Man bestemmer så ved gassfasekromatografi de klorerte organiske forbindelser i det endelige bad og også i heksanet. The chlorinated organic compounds in the final bath and also in the hexane are then determined by gas phase chromatography.

Resultatene er gitt i Tabell 1. The results are given in Table 1.

Eksempel 2 Example 2

Man gjennomfører den samme prøve men man innfører i tillegg til kloraluminatbadet 5$ finpulverisert aluminium av typen "PECHINEY XY 49". Etter 1 time ved 200°C og etter spyling i 15 minutter med 50 l/time N£ tar man av en prøve fra badet og fra heksanet for analyse. Resultatene er gitt i Tabell 1. The same test is carried out, but in addition to the chloraluminate bath, 5$ of finely powdered aluminum of the type "PECHINEY XY 49" is introduced. After 1 hour at 200°C and after flushing for 15 minutes with 50 l/hour N£, a sample is taken from the bath and from the hexane for analysis. The results are given in Table 1.

Eksempel 3 Example 3

Man arbeider i den samme apparatur som ble benyttet i eksemplene 1 og 2 men modifiserer driftsbetingelsene: One works in the same apparatus as was used in examples 1 and 2, but modifies the operating conditions:

- badtemperatur: 250°C - bath temperature: 250°C

- vekt av kloraluminatbadet: 500 g - weight of the chloraluminate bath: 500 g

- tilsetning av 5% Al pulver "PECHINEY XY 49" - addition of 5% Al powder "PECHINEY XY 49"

- eksempelvarighet: 2 timer - sample duration: 2 hours

- spyling med nitrogen etter 2 timer: 15 minutter - flushing with nitrogen after 2 hours: 15 minutes

- ved start tilsetning av: 500 mg heksaklorbenzen - at the start addition of: 500 mg hexachlorobenzene

500 mg decaklorbifenyl Resultatene er gitt i Tabell 2. 500 mg decachlorobiphenyl The results are given in Table 2.

Eksempel 4 Example 4

Samme analyse som i Eksempel 3 men varigheten var 4 timer. Same analysis as in Example 3 but the duration was 4 hours.

Resultatene er gitt i Tabell 2. The results are given in Table 2.

Claims (7)

1. Fremgangsmåte for destruering av klorerte organiske produkter med mer enn 2 karbonatomer, hvor man bringer produktene i kontakt med et bad av minst ett kloraluminat, k a r a k t e risert ved at begynnelses-konsentrasjonen av de klorinerte organiske produkter i badet er under 5000 ppm og fortrinnsvis under 2000 ppm, beregnet på kloraluminatet og at temperaturen i badet er under 300"C.1. Process for destroying chlorinated organic products with more than 2 carbon atoms, where the products are brought into contact with a bath of at least one chloroaluminate, characterized in that the initial concentration of the chlorinated organic products in the bath is below 5000 ppm and preferably below 2000 ppm , calculated for the chloraluminate and that the temperature in the bath is below 300"C. 2. Fremgangsmåte ifølge krav 1,karakterisert ved at kloraluminatet er kloraluminat av natrium.2. Method according to claim 1, characterized in that the chloraluminate is sodium chloraluminate. 3. Fremgangsmåte ifølge krav 2,karakterisert ved at kloraluminatet av natrium inneholder minst 50 mol-# aluminiumklorid.3. Process according to claim 2, characterized in that the chloroaluminate of sodium contains at least 50 mol-# of aluminum chloride. 4. Fremgangsmåte ifølge et hvilket som helst av kravene 1 til 3, karakterisert ved at temperaturen i badet av kloraluminat er mellom 200 og 300°C.4. Method according to any one of claims 1 to 3, characterized in that the temperature in the bath of chloraluminate is between 200 and 300°C. 5. Fremgangsmåte ifølge et hvilket som helst av kravene 1 til 4, karakterisert ved at kloraluminatet inneholder minst et metall i pulverform.5. Method according to any one of claims 1 to 4, characterized in that the chloraluminate contains at least one metal in powder form. 6. Fremgangsmåte ifølge krav 5, karakterisert ved at det som metall benyttes aluminium.6. Method according to claim 5, characterized in that aluminum is used as the metal. 7. Fremgangsmåte ifølge et hvilket som helst av kravene 5 eller 6,karakterisert ved at den midlere partik-kelstørrelse for pulveret er under 500 pm.7. Method according to any one of claims 5 or 6, characterized in that the average particle size of the powder is below 500 pm.
NO880104A 1987-01-21 1988-01-12 Process for the destruction of chlorinated organic products at low temperature NO174088C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8700669A FR2609652B1 (en) 1987-01-21 1987-01-21 PROCESS FOR THE DESTRUCTION OF LOW TEMPERATURE CHLORINE PRODUCTS

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NO880104D0 NO880104D0 (en) 1988-01-12
NO880104L NO880104L (en) 1988-07-22
NO174088B true NO174088B (en) 1993-12-06
NO174088C NO174088C (en) 1994-03-16

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DE (1) DE3860064D1 (en)
DK (1) DK166432B1 (en)
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FR (1) FR2609652B1 (en)
GR (1) GR3000437T3 (en)
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US4931167A (en) * 1987-10-13 1990-06-05 Advanced Refinery Technology Degradation of polychlorinated biphenyls
US5490919A (en) * 1990-08-14 1996-02-13 State Of Isreal, Atomic Energy Commission Process for the dehalogenation of organic compounds
JP4458585B2 (en) * 1999-09-09 2010-04-28 祝治 朝倉 Methods for decomposing and detoxifying harmful organic compounds

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JPS5257149A (en) * 1975-11-07 1977-05-11 Gunma Daigakuchiyou Method of decomposing halogenated aromatic compounds to carboneous substance using molten salts
US4469661A (en) * 1982-04-06 1984-09-04 Shultz Clifford G Destruction of polychlorinated biphenyls and other hazardous halogenated hydrocarbons
US4447262A (en) * 1983-05-16 1984-05-08 Rockwell International Corporation Destruction of halogen-containing materials

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EP0277858A1 (en) 1988-08-10
FI880241A (en) 1988-07-22
GR3000437T3 (en) 1991-06-28
AU610552B2 (en) 1991-05-23
FI880241A0 (en) 1988-01-20
DK23288A (en) 1988-07-22
DE3860064D1 (en) 1990-05-10
NO880104D0 (en) 1988-01-12
DK23288D0 (en) 1988-01-20
IE880137L (en) 1988-07-21
EP0277858B1 (en) 1990-04-04
IN170563B (en) 1992-04-11
PT86577B (en) 1991-12-31
FR2609652A1 (en) 1988-07-22
NZ223232A (en) 1991-05-28
IE60535B1 (en) 1994-07-27
CN1012142B (en) 1991-03-27
FR2609652B1 (en) 1992-05-15
JPS63192468A (en) 1988-08-09
DK166432B1 (en) 1993-05-24
ATE51531T1 (en) 1990-04-15
NO880104L (en) 1988-07-22
CN88100299A (en) 1988-08-03
CA1333404C (en) 1994-12-06
NO174088C (en) 1994-03-16
AU1062188A (en) 1988-07-28
PT86577A (en) 1988-02-01
ES2014508B3 (en) 1990-07-16

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