NL192876C - Process for the hydroxylation of aromatic hydrocarbons. - Google Patents
Process for the hydroxylation of aromatic hydrocarbons. Download PDFInfo
- Publication number
- NL192876C NL192876C NL8300962A NL8300962A NL192876C NL 192876 C NL192876 C NL 192876C NL 8300962 A NL8300962 A NL 8300962A NL 8300962 A NL8300962 A NL 8300962A NL 192876 C NL192876 C NL 192876C
- Authority
- NL
- Netherlands
- Prior art keywords
- hydrogen peroxide
- phenol
- pitch
- hydroxylation
- reaction
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
1 1928761 192876
Werkwijze voor het hydroxyleren van aromatische koolwaterstoffenProcess for the hydroxylation of aromatic hydrocarbons
De uitvinding heeft betrekking op een werkwijze voor het hydroxyleren van aromatische koolwaterstoffen met behulp van waterstofperoxide, waarbij de aromatische koolwaterstof wordt gekozen uit fenol, tolueen, 5 anisool, de xylenen, mesityleen, benzeen, nitrobenzeen, ethylbenzeen, of aceetanilide en men deze verbindingen laat reageren in tegenwoordigheid van een keton en titaansilicaliet bij een temperatuur van 80-120°C.The invention relates to a process for the hydroxylation of aromatic hydrocarbons using hydrogen peroxide, wherein the aromatic hydrocarbon is selected from phenol, toluene, anisole, the xylenes, mesitylene, benzene, nitrobenzene, ethylbenzene, or acetanilide and these compounds are left react in the presence of a ketone and titanium silicalite at a temperature of 80-120 ° C.
Een dergelijke werkwijze is bekend uit de Franse octrooiaanvrage 2.489.816 (overeenkomend met de Nederlandse octrooiaanvrage 8104175, inmiddel octrooi 191629), en wordt uitgevoerd in tegenwoordigheid 10 van synthetische zeolieten die ofwel gesubstitueerde ofwel uitgewisselde heteroatomen bevatten. Het gebruik van een dergelijk zeoliet bleek het mogelijk te maken om de reactie te richten op de vorming van één product. Zeolietmaterialen die kunnen worden toegepast bij de werkwijze volgens deze octrooiaanvrage kunnen worden gekozen uit bijvoorbeeld die, welke zijn beschreven in de Nederlandse octrooiaanvrage 7904909, zoals bijvoorbeeld titaansilicaliet: een kristallijn siliciumdioxlde dat is gemodificeerd met titaan. De 15 reactie van de aromatische koolwaterstof voert men uit bij een temperatuur van 80-120°C, desgewenst in aanwezigheid van een oplosmiddel, waardoor althans gedeeltelijke vermenging met het waterstofperoxide mogelijk wordt, waarvoor water, methanol, azijnzuur, isopropanol en acetonitril kunnen worden gebruikt. Blijkens de voorbeelden en FR-A-2489816 kan de reactie voorts worden uitgevoerd in aanwezigheid van een keton, in het bijzonder methylisobutylketon en methylisopropylketon.Such a method is known from French patent application 2,489,816 (corresponding to Dutch patent application 8104175, in patent 191629), and is carried out in the presence of synthetic zeolites containing either substituted or exchanged heteroatoms. The use of such a zeolite has been found to make it possible to direct the reaction towards the formation of one product. Zeolite materials that can be used in the process of this patent application can be selected from, for example, those described in Dutch patent application 7904909, such as, for example, titanium silicalite: a crystalline silicon dioxide which has been modified with titanium. The reaction of the aromatic hydrocarbon is carried out at a temperature of 80-120 ° C, optionally in the presence of a solvent, permitting at least partial mixing with the hydrogen peroxide, for which water, methanol, acetic acid, isopropanol and acetonitrile can be used. . According to the examples and FR-A-2489816, the reaction can further be carried out in the presence of a ketone, in particular methyl isobutyl ketone and methyl isopropyl ketone.
20 Gevonden is nu dat het mogelijk is om de hierboven aangeduide reactie uit te voeren met hoge toevoerverhoudrngen en met hoge opbrengsten en selectiviteiten ten opzichte van de bekende werkwijze onder toepassing van methylisobutylketon, waartoe de werkwijze volgens de uitvinding wordt gekenmerkt doordat men de reactie uitvoert in tegenwoordigheid van aceton en een molaire waterstofperoxide/ aromatische koolwaterstofverhouding van 15 tot 60.10'2.It has now been found that it is possible to carry out the above-indicated reaction with high feed ratios and with high yields and selectivities compared to the known method using methyl isobutyl ketone, for which the method according to the invention is characterized in that the reaction is carried out in presence of acetone and a hydrogen peroxide / aromatic hydrocarbon molar ratio of 15 to 60.10'2.
25 Opgemerkt wordt dat het op zichzelf voorgesteld is om bij dergelijke hydroxyleringswerkwijzen aceton toe te passen als oplosmiddel voor zowel waterstofperoxide als de koolwaterstof (zie EP-A-0 021 848 en FR-A-2.290.411). Deze bekende werkwijzen met een α-hydroxy- of een α,β-onverzadigde alkyl-gesubstitueerde aromatische verbinding respectievelijk met een fenylether worden echter uitgevoerd in aanwezigheid van een vloeibare proton-zure katalysator.It should be noted that it has been proposed per se to use acetone as a solvent for both hydrogen peroxide and the hydrocarbon in such hydroxylation processes (see EP-A-0 021 848 and FR-A-2,290,411). However, these known processes with an α-hydroxy or an α, β-unsaturated alkyl-substituted aromatic compound or with a phenyl ether are carried out in the presence of a liquid protonic acid catalyst.
30 Voorts wordt opgemerkt dat de reactie volgens de uitvinding bij voorkeur wordt uitgevoerd bij de terugvloeitemperatuur. De daarbij gevormde hoeveelheid zware nevenproducten bleek zeer gering te zijn.It is further noted that the reaction according to the invention is preferably carried out at the reflux temperature. The amount of heavy by-products formed thereby was found to be very small.
De uitvoeringsomstandigheden van de werkwijze volgens de uitvinding worden hierna toegelicht aan de hand van de hiernavolgende voorbeelden, waarin de volgende definities worden toegepast: „ , Toegevoerde aantal moleculen H202 35 oevoerver ou ing = joegevoer(je aantal moleculen fenol x 100 * i °°The operating conditions of the method according to the invention are explained below with reference to the following examples, in which the following definitions are applied: ", Number of molecules supplied H2O2 35 feed = feed feed (your number of molecules phenol x 100 * i ° °
CftnfttnpmaHrnn Aantal omgezette moleculen fenol 40 e o o e g - Aanta( toegevoerde moleculen fenolx 0 ._____Aantal moleculen hvdrochinon.. *ΛΛCftnfttnpmaHrnn Number of converted phenol molecules 40 e o o e g - Number (introduced phenol molecules 0 ._____ Number of hvdroquinone molecules .. * ΛΛ
Hydrochinonselectiviteit = Aantal moleculen difenden x10°Hydroquinone selectivity = Number of molecules diffends x10 °
Voorbeeld IExample I
Men brengt 50 g fenol, 39 g aceton en 2,5 g titaansilicaliet (volgens voorbeeld I van FR-A-2489816) in een 45 250 ml kolf. Als het systeem een temperatuur van 80°C bereikt, voegt men 10 cc 30%’s w/v waterstofperoxide toe. Na een reactieduur van twee uren worden de volgende resultaten verkregen, fenol selectiviteit 96,25% fenol omzetting 18,36% waterstofperoxide opbrengst 88,5 % 50 pek/pek+difenolen 4,2 % hydrochinon selectiviteit 50 %50 g of phenol, 39 g of acetone and 2.5 g of titanium silicalite (according to Example I of FR-A-2489816) are placed in a 250 ml flask. When the system reaches a temperature of 80 ° C, 10 cc of 30% w / v hydrogen peroxide is added. After a reaction time of two hours, the following results are obtained, phenol selectivity 96.25% phenol conversion 18.36% hydrogen peroxide yield 88.5% 50 pitch / pitch + diphenols 4.2% hydroquinone selectivity 50%
Voorbeeld IIExample II
Men volgt de werkwijze van voorbeeld I, doch voegt 15 cc 36%’s w/v waterstofperoxide toe. Men verkrijgt 55 na 2 uren de volgende resultaten: fenol selectiviteit 94,45% fenol omzetting 24,25% 192876 2 waterstofperoxide opbrengst 79,6 % pek/pek+difenolen 5,1 % hydrochinon selectiviteit 50 %The procedure of Example 1 is followed, but 15 cc of 36% w / v hydrogen peroxide is added. After 2 hours, 55 the following results are obtained: phenol selectivity 94.45% phenol conversion 24.25% 192876 2 hydrogen peroxide yield 79.6% pitch / pitch + diphenols 5.1% hydroquinone selectivity 50%
5 Voorbeeld IIIExample III
Men volgt de werkwijze van voorbeeld II, doch voegt 20 cc 36%’s w/v waterstofperoxide toe. Na 2 uren verkrijgt men de volgende resultaten: fenol selectiviteit 92,96% fenol omzetting 31,28% 10 waterstofperoxide opbrengst 73,9 % pek/pek+difenolen 7,8 % hydrochinon selectiviteit 50 %The procedure of Example II is followed, but 20 cc of 36% w / v hydrogen peroxide is added. After 2 hours the following results are obtained: phenol selectivity 92.96% phenol conversion 31.28% 10 hydrogen peroxide yield 73.9% pitch / pitch + diphenols 7.8% hydroquinone selectivity 50%
Voorbeeld IVExample IV
15 Men volgt de werkwijze van voorbeeld lil, doch voegt 25 cc 36%’s w/v waterstofperoxide toe. De volgende resultaten verkrijgt men na 2 uren: fenol selectiviteit 91,29% waterstofperoxide opbrengst 68,9 % pek/pek+difenolen 9,7 % 20 hydrochinon selectiviteit 50 % fenol omzetting 36,64%The procedure of Example 11 is followed, but 25 cc of 36% w / v hydrogen peroxide is added. The following results are obtained after 2 hours: phenol selectivity 91.29% hydrogen peroxide yield 68.9% pitch / pitch + diphenols 9.7% 20 hydroquinone selectivity 50% phenol conversion 36.64%
Voorbeeld VExample V
Men volgt de werkwijze van voorbeeld IV, doch voegt 30 cc 36%’s w/v waterstofperoxide toe. Na 2 uren 25 verkrijgt men de volgende resultaten: fenol selectiviteit 89,4 % waterstofperoxide opbrengst 59,4 % pek/pek+difenolen 12 % hydrochinon selectiviteit 50 % 30 fenol omzetting 37,76%The procedure of Example IV is followed, but 30 cc of 36% w / v hydrogen peroxide is added. After 2 hours 25 the following results are obtained: phenol selectivity 89.4% hydrogen peroxide yield 59.4% pitch / pitch + diphenols 12% hydroquinone selectivity 50% phenol conversion 37.76%
Voorbeeld VIExample VI
Men brengt 30 cc anisool, 70 cc aceton en 3 g katalysator in een kolf van 250 cc, voorzien van een bolcondensor. Wanneer een temperatuur van 70°C is bereikt, voegt men druppelsgewijze 7,5 cc 36%’s 35 waterstofperoxide toe. De reactie wordt uitgevoerd bij een temperatuur van 70°C. Na afloop van de reactie verkrijgt men de volgende resultaten: waterstofperoxide opbrengst 72,8 % anisool omzetting 22,7 % pek/pek+producten 6,26% 40 anisooiopbrengst 90,6 % berekend als moleculen HMME + moleculen gevormd guajacol 1QQ moleculen omgezet anisool w 45 Productverdeling: hydrochinonmonomethylether (HMME) 64% guajacol 36%.30 cc of anisole, 70 cc of acetone and 3 g of catalyst are placed in a 250 cc flask fitted with a condenser condenser. When a temperature of 70 ° C is reached, 7.5 cc of 36% hydrogen peroxide is added dropwise. The reaction is carried out at a temperature of 70 ° C. After the reaction, the following results are obtained: hydrogen peroxide yield 72.8% anisole conversion 22.7% pitch / pitch + products 6.26% 40 anisole yield 90.6% calculated as molecules HMME + molecules formed guajacol 1QQ molecules converted anisole w 45 Product distribution: hydroquinone monomethyl ether (HMME) 64% guajacol 36%.
Voorbeeld VIIExample VII
Men volgt de werkwijze van voorbeeld VI, doch voegt 10 cc 36%’s waterstofperoxide toe.The procedure of Example VI is followed, but 10 cc of 36% hydrogen peroxide is added.
Men verkrijgt de volgende resultaten: 50 watersofperoxide opbrengst 70% anisooiopbrengst 85% anisoolomzetting 24% pek/pek+producten 11% product verdeling:HMME 64% 55 guajacol 36%The following results are obtained: 50 hydrogen peroxide yield 70% anisoo yield 85% anisole conversion 24% pitch / pitch + products 11% product distribution: HMME 64% 55 guajacol 36%
De in bovenstaande voorbeelden toegepaste katalysator bestaat uit een titaansilicaliet, bereid volgens de in voorbeeld I van de Nederlandse octrooiaanvrage 8006939 beschreven werkwijze.The catalyst used in the above examples consists of a titanium silicalite, prepared according to the method described in Example 1 of Dutch patent application 8006939.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2026282 | 1982-03-19 | ||
| IT20262/82A IT1150699B (en) | 1982-03-19 | 1982-03-19 | PROCEDURE FOR THE OXIDRILATION OF AROMATIC HYDROCARBONS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8300962A NL8300962A (en) | 1983-10-17 |
| NL192876B NL192876B (en) | 1997-12-01 |
| NL192876C true NL192876C (en) | 1998-04-02 |
Family
ID=11165238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8300962A NL192876C (en) | 1982-03-19 | 1983-03-17 | Process for the hydroxylation of aromatic hydrocarbons. |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE896225A (en) |
| CH (1) | CH652114A5 (en) |
| DE (1) | DE3309669A1 (en) |
| DK (1) | DK171933B1 (en) |
| FR (1) | FR2523575B1 (en) |
| GB (1) | GB2116974B (en) |
| IT (1) | IT1150699B (en) |
| NL (1) | NL192876C (en) |
| NO (1) | NO156648C (en) |
| SE (1) | SE461730B (en) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2618143B1 (en) * | 1987-07-17 | 1989-09-22 | Rhone Poulenc Chimie | PHENOL HYDROXYLATION PROCESS |
| US5254746A (en) * | 1987-10-29 | 1993-10-19 | Rhone-Poulenc Chimie | Hydroxylation of phenols/phenol ethers |
| FR2622575B1 (en) * | 1987-10-29 | 1990-02-23 | Rhone Poulenc Chimie | PROCESS FOR HYDROXYLATION OF PHENOLS AND PHENOL ETHERS |
| FR2622574B1 (en) * | 1987-10-29 | 1990-02-23 | Rhone Poulenc Chimie | PROCESS FOR HYDROXYLATION OF PHENOLS AND PHENOL ETHERS |
| FR2643633B1 (en) * | 1989-02-28 | 1991-05-10 | Rhone Poulenc Chimie | PROCESS FOR HYDROXYLATION OF PHENOLS AND PHENOL ETHERS |
| FR2666333B1 (en) * | 1990-08-31 | 1994-04-08 | Rhone Poulenc Chimie | PROCESS FOR HYDROXYLATION OF PHENOLS AND PHENOL ETHERS. |
| EP0466545A1 (en) * | 1990-06-29 | 1992-01-15 | Rhone-Poulenc Chimie | Zeolites based on silica and oxides of tetravalent elements, method for their synthesis and their use |
| EP0473509A3 (en) * | 1990-08-29 | 1992-03-18 | Rhone-Poulenc Chimie | Method for preparation of zeolites based on silica and, possibly, oxides of tetravalent elements |
| DE4138155A1 (en) | 1991-11-21 | 1993-05-27 | Basf Ag | METHOD FOR PRODUCING ESSENTIALLY ALKALIFIED TITANICILICATE CRYSTALS WITH ZEOLITE STRUCTURE |
| US5426244A (en) * | 1991-12-20 | 1995-06-20 | Mitsubishi Gas Chemical Company, Inc. | Method for preparing dihydric phenols |
| DE4214174A1 (en) * | 1992-04-30 | 1993-11-04 | Basf Ag | METHOD FOR PRODUCING N-HYDROXYAZOLES |
| FR2693457B1 (en) * | 1992-07-10 | 1994-09-02 | Rhone Poulenc Chimie | Process for the hydroxylation of phenolic compounds. |
| US5233097A (en) * | 1992-10-15 | 1993-08-03 | Uop | Oxidation of aromatics to hydroxyaromatics using aluminosilicates containing framework titanium |
| ATE143831T1 (en) * | 1992-12-03 | 1996-10-15 | Kataleuna Gmbh Catalysts | OXIDATION CATALYSTS |
| DE4419195A1 (en) * | 1993-07-12 | 1995-01-19 | Degussa | Structured catalyst consisting of microporous oxides of silicon, aluminum and titanium |
| RU2058286C1 (en) * | 1994-04-12 | 1996-04-20 | Институт катализа им.Г.К.Борескова СО РАН | Method for production of phenol or its derivatives |
| RU2074164C1 (en) * | 1994-04-12 | 1997-02-27 | Институт катализа им.Г.К.Борескова СО РАН | Method of producing phenol and derivatives thereof |
| US5712402A (en) | 1994-08-22 | 1998-01-27 | Board Of Trustees Operating Michigan State University | Catalytic applications of mesoporous metallosilicate molecular sieves and methods for their preparation |
| DE19607577A1 (en) * | 1996-02-29 | 1997-09-04 | Basf Ag | Mesh catalyst based on titanium or vanadium zeolites and inert mesh fabrics to accelerate oxidation reactions |
| US5874646A (en) * | 1996-08-07 | 1999-02-23 | Solutia Inc. | Preparation of phenol or phenol derivatives |
| US5892132A (en) * | 1996-08-08 | 1999-04-06 | Solutia Inc. | Transport hydroxylation reactor |
| US5808167A (en) * | 1996-08-20 | 1998-09-15 | Solutia Inc. | Selective introduction of active sites for hydroxylation of benzene |
| US5874647A (en) * | 1996-08-20 | 1999-02-23 | Solutia Inc. | Benzene hydroxylation catalyst stability by acid treatment |
| BR9711870B1 (en) | 1996-10-07 | 2011-10-18 | process for making phenol. | |
| US6156938A (en) * | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
| EE200000234A (en) | 1997-11-14 | 2001-06-15 | Dupont Pharmaceuticals Company | Radioactive seed crystals for brachytherapy and process for their preparation |
| EP1044196A2 (en) * | 1997-11-24 | 2000-10-18 | E.I. Du Pont De Nemours And Company | Process for the selective oxidation of organic compounds |
| DE19939416A1 (en) | 1999-08-20 | 2001-02-22 | Basf Ag | Production of zeolite, e.g. titanium zeolite, useful as catalyst (support), sorbent, pigment or filler for plastics, involves crystallizing solid from precursor(s) and direct drying of reaction mixture |
| US6437197B1 (en) * | 2000-04-27 | 2002-08-20 | Shell Oil Company | Process for catalytic hydroxylation of aromatic hydrocarbons |
| JP2005060384A (en) * | 2003-07-30 | 2005-03-10 | Ube Ind Ltd | Manufacturing method of phenol compound |
| WO2005063664A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific & Industrial Research | Process for conversion of phenol to hydroquinone and quinones |
| CA2598013C (en) | 2005-02-17 | 2014-11-25 | Monsanto Technology Llc | Transition metal-containing catalysts and catalyst combinations including transition metal-containing catalysts and processes for their preparation and use as oxidation catalysts |
| FR2987046B1 (en) * | 2012-02-17 | 2014-03-21 | Rhodia Operations | HYDROXYLATION PROCESS FOR AROMATIC COMPOUNDS, HYDROXYLATION CATALYST AND PROCESS FOR PREPARING THE SAME |
| TWI471299B (en) | 2012-10-04 | 2015-02-01 | China Petrochemical Dev Corp Taipei Taiwan | Hydroxylation of phenol |
| CN105523898B (en) * | 2014-09-29 | 2019-03-22 | 中国石油化工股份有限公司 | A kind of method of oxidation of phenol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1448358A (en) * | 1974-04-04 | 1976-09-08 | Ube Industries | Process for preparint dihydric phenol derivatives |
| US4013727A (en) * | 1974-11-07 | 1977-03-22 | Ube Industries, Ltd. | Process for preparing hydroxyphenyl ethers |
| IT1195029B (en) * | 1980-09-09 | 1988-09-28 | Anic Spa | PROCEDURE FOR THE OXIDRILATION OF AROMATIC HYDROCARBONS |
-
1982
- 1982-03-19 IT IT20262/82A patent/IT1150699B/en active
-
1983
- 1983-03-16 GB GB08307296A patent/GB2116974B/en not_active Expired
- 1983-03-16 CH CH1454/83A patent/CH652114A5/en not_active IP Right Cessation
- 1983-03-16 NO NO830926A patent/NO156648C/en not_active IP Right Cessation
- 1983-03-17 DK DK123783A patent/DK171933B1/en not_active IP Right Cessation
- 1983-03-17 NL NL8300962A patent/NL192876C/en not_active IP Right Cessation
- 1983-03-17 DE DE19833309669 patent/DE3309669A1/en active Granted
- 1983-03-18 FR FR8304502A patent/FR2523575B1/en not_active Expired
- 1983-03-18 SE SE8301492A patent/SE461730B/en not_active IP Right Cessation
- 1983-03-21 BE BE0/210368A patent/BE896225A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE461730B (en) | 1990-03-19 |
| BE896225A (en) | 1983-09-21 |
| DK123783A (en) | 1983-09-20 |
| IT8220262A1 (en) | 1983-09-19 |
| GB8307296D0 (en) | 1983-04-20 |
| NL8300962A (en) | 1983-10-17 |
| SE8301492D0 (en) | 1983-03-18 |
| CH652114A5 (en) | 1985-10-31 |
| DE3309669C2 (en) | 1990-10-25 |
| IT1150699B (en) | 1986-12-17 |
| GB2116974A (en) | 1983-10-05 |
| DE3309669A1 (en) | 1983-09-29 |
| NO156648C (en) | 1987-10-28 |
| NO156648B (en) | 1987-07-20 |
| FR2523575B1 (en) | 1986-10-10 |
| FR2523575A1 (en) | 1983-09-23 |
| NL192876B (en) | 1997-12-01 |
| NO830926L (en) | 1983-09-20 |
| SE8301492L (en) | 1983-09-20 |
| GB2116974B (en) | 1985-10-02 |
| IT8220262A0 (en) | 1982-03-19 |
| DK171933B1 (en) | 1997-08-18 |
| DK123783D0 (en) | 1983-03-17 |
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