US3859183A - Process for producing n-phosphonomethyl glycine triesters - Google Patents

Process for producing n-phosphonomethyl glycine triesters Download PDF

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Publication number
US3859183A
US3859183A US413476A US41347673A US3859183A US 3859183 A US3859183 A US 3859183A US 413476 A US413476 A US 413476A US 41347673 A US41347673 A US 41347673A US 3859183 A US3859183 A US 3859183A
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US
United States
Prior art keywords
tetra
triester
ester
phosphonomethyl glycine
diacetic acid
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.)
Expired - Lifetime
Application number
US413476A
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English (en)
Inventor
John H Wagenknecht
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
Original Assignee
Monsanto Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to US413476A priority Critical patent/US3859183A/en
Priority to IL45990A priority patent/IL45990A/en
Priority to NLAANVRAGE7414397,A priority patent/NL173773C/xx
Priority to EG493/74A priority patent/EG11633A/xx
Priority to ES431642A priority patent/ES431642A1/es
Priority to AU75087/74A priority patent/AU492150B2/en
Priority to BG028135A priority patent/BG27092A3/xx
Priority to IT29168/74A priority patent/IT1025475B/it
Priority to YU2974/74A priority patent/YU39930B/xx
Priority to IN2439/CAL/1974A priority patent/IN140891B/en
Priority to RO80441A priority patent/RO72486B/ro
Priority to SE7413908A priority patent/SE401926B/xx
Priority to PL1974175374A priority patent/PL92408B1/pl
Priority to BR9282/74A priority patent/BR7409282A/pt
Priority to CA213,144A priority patent/CA1030900A/en
Priority to CH1483874A priority patent/CH615932A5/de
Priority to FR7436868A priority patent/FR2249974B1/fr
Priority to ZA00747144A priority patent/ZA747144B/xx
Priority to AT889074A priority patent/AT337206B/de
Priority to DD182198A priority patent/DD116237A5/xx
Priority to CS7559A priority patent/CS177191B2/cs
Priority to GB4791574A priority patent/GB1452644A/en
Priority to PH16491A priority patent/PH10866A/en
Priority to BE150245A priority patent/BE821891A/xx
Priority to DK577674AA priority patent/DK140897B/da
Priority to JP12724074A priority patent/JPS5441573B2/ja
Priority to DE19742452701 priority patent/DE2452701C3/de
Priority to IE2284/74A priority patent/IE40538B1/xx
Priority to HU74MO00000922A priority patent/HU171934B/hu
Priority to AR256425A priority patent/AR216279A1/es
Application granted granted Critical
Publication of US3859183A publication Critical patent/US3859183A/en
Priority to MY41/78A priority patent/MY7800041A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/23—Oxidation

Definitions

  • a solution of a tetra ester of N- phosphonomethylimino diacetic acid dissolved in a suitable solvent containing an electrolyte is subjected to an electromotive force or electric current in an electrolytic cell to be electrolytically oxidized to a triester of N-phosphonomethyl glycine.
  • the triester of N-phosphonomethyl glycine produced can be hydrolyzed to the free acid and its salt derivatives which are useful as post-emergent herbicides.
  • This invention relates to a method of producing N- phosphonomethyl glycine triester thereof by the electrolytic oxidation of the tetra esters of N- (phosphonomethyl) imino-diacetic acid. More particularly, this invention relates to the production of N- phosphonomethyl glycine triesters by the electrolysis of tetra esters of N-(phosphonomethyl) imino-diacetic acid in a suitable solvent medium containing a supporting electrolyte.
  • an organic solvent electrolytic solution of the tetra ester of N-phosphonomethylimino diacetic acid is charged into an electrolytic cell fitted with an anode and a cathode and an electromotive force or electric current impressed upon the cell whereby the tetra ester of N- phosphonomethylimino diacetic acid is electrolytically oxidized to yield the triester of N-phosphonomethyl glycine, as the principal product.
  • a 5% to 20% solution of tetra ester of N- phosphonomethylimino diacetic acid dissolved in acetonitrile containing a dissolved supporting electrolyte is charged into an electrolytic cell maintained at a temperature of from C. or less to 100 C. or more and having noble metal, graphite or carbon electrodes.
  • An electric current is then impressed on the cell by connecting the anode and cathode to a proper source of direct current with controls to maintain the current density at between .01 and 100 ma/cm for a time sufficient to oxidize the tetra ester of N- phosphonomethylimino diacetic acid to the triester of N-phosphonomethyl glycine.
  • the resultant reaction solution is then vacuum evaporated to remove the solvent and reaction by-products.
  • the triester residue is then dissolved in water, hydrolyzed and recovered as a N-phosphonomethyl glycine by recrystallization upon the cooling of the water solution.
  • concentration of the tetra ester of N- phosphonomethylimino diacetic acid employed in the process of this invention is not critical and is limited only by the solubility of the starting material in the particular solvent employed. Thus, for example, although concentrations as low as 0.01% by weight in the solvent can be employed, for reasons of efficiency and economy, it is preferred to employ concentrations of from about 5 to about 30% by weight, or even higher, of the tetra ester of N-phosphonomethylimino diacetic acid in the solvent containing supporting electrolyte.
  • the temperature at which the process of the instant invention is conducted is not narrowly critical and can range from as low as 0 C. to as high as 110 C. or even higher if a pressure cell is employed.
  • the temperature employed is a function of the solvent boiling point, freezing point, pressure and solubility of reactants and reaction products. As is apparent to those skilled in the art, at lower temperatures a very dilute solution or a suspension must be employed since the solubility of the tetra ester of N-phosphonomethylimino diacetic acid starting material is lower at lower temperatures.
  • the process of the instant invention can be conducted at atmospheric pressure, super atmospheric pressures and subatmospheric pressures. For reasons of economy and ease of construction of the equipment employed in the process ofthis invention, it is preferred to conduct this process at approximately atmospheric pressure.
  • the type of electrolytic cell employed in the process of this invention is not critical.
  • the cell can consist of a glass container having one or more anodes and cathodes connected to a source of direct current, such as a battery and the like or a source of low frequence alternating current.
  • the cell can also consist of the two electrodes separated by an insulator such as a rubber or other non-conducting gasket.
  • the current densities employed in the process of-this invention can range from as low as 1 milliampere per square centimeter (malcm to 60 or more ma/cm In general, it is preferred to employ current densities of from about I to about 10 for best yields of the desired triester of N-phosphonomethyl glycine. At higher current densities, the electrolytic efficiency of the cell is decreased. At the higher current densities there are also undesirable side reactions, such as electrolysis of the solvent and decomposition of the desired product into desirable by-products.
  • the electrodes i.e., the anode and cathode, employed in the process of this invention can be constructed of a wide variety of materials and combinations of materials.
  • the anodes may be constructed of any conductive substance, such as lead, graphite, lead oxide, lead sulfate, carbon in various forms, platinum, various metal oxides such as manganese dioxide, copper oxide, nickel oxide and the like, and can be in many different forms such as gauze, solids, porous, etc.
  • Other electrode materials are less preferred since they corrode rapidly and their ions contaminate the electrolyte, thereby rendering the isolation of the product more expensive and difficult.
  • the cathodes can also be of any conductive substance such as copper, lead, platinum, palladium, lead oxide, graphite, carbon and the like. It is preferred to employ a noble metal such as palladium or platinum or various forms of graphite, carbon or glassy carbon as the electrode materials employed in the process of this invention.
  • the enabling electrolytes which can be employed to render the solvent medium conducting include the metal perchlorates, fluoroborates, acetates, hexafluoro phosphate and the like.
  • the only limitation on the enabling electrolyte being employed is that it dissolves in the solvent, that it ionizes in the solvent and that it is not oxidized at the potential of the oxidation of the tetra ester of N-phosphonomethyl glycine in the specific solvent being employed.
  • Such enabling electrolytes are salts such as ammonium hexafluoro phosphate, ammonium fluoroborate and the a]- kali or alkaline earth metal salts such as sodium, potassium or rubidium hexafluoro phosphate, sodium fluoroborate, tetramethylammonium fluoroborate, tetraethylammonium fluoroborate, tetramethylammonium ethylsulfate, tetraethylammonium ethylsulfate, trimethylammonium fluoroborate, trimethylammonium hexafluorophosphate, tetramethylammonium toluenesulfonate, tetraethylammonium toluenesulfonate dimethylammonium fluoroborate, diethylammonium perchlorate, tetrapropylammonium perchlorate, lithium perchlorate,
  • a solvent is essential.
  • the solvent must be one in which the tetra ester of N- phosphonomethylimino diacetic acid is soluble and also in which the supporting electrolyte is soluble so that the solution is conductive.
  • nitriles such as acetonitrile, propionitrile, benzonitrile, etc.
  • nitro compounds such as nitromethane, nitroethane, etc
  • halogenated hydrocarbons such as methylene chloride, ethylene chloride, etc
  • cyclic ethers such as tetrahydrofuran, and the ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl'ether and mixtures of the above solvents with each other and with aliphatic alcohols, etc.
  • time of reaction is variable and is determined by variables such as current density, electrode area concentration and volume of the reaction solution.
  • the triesters of N-phosphonomethyl glycine product of the process of the present invention is recovered from the reaction solution by conventional techniques known to .those skilled in the art, such as by extraction and recrystallization, centrifugation, concentration and the like.
  • the triesters can by hydrolyzed with an acid such as dilute hydrochloric acid to yield N- phosphonomethyl glycine which is useful as a herbicide.
  • the hydrolysis reaction solution can be vacuum evaporated to eliminate the water, acid, and alcohol by-product.
  • the solid which remains can be dissolved in water and then cooled to precipitate the N- phosphonomethyl glycine, which is recovered by filtration.
  • the tetra esters of N-phosphonomethylimino diacetic acid useful in the process of this invention are those having the general formula o o omo OR ⁇ ll /PCH2N ⁇ /O O CHzC wherein R, R, R" and R" are each independently monovalent hydrocarbon radicals containing from one to 12 carbon atoms, halogenated monovalent hydrocarbon radicals, and hydrocarbon oxyhydrocarbon groups containing from one to four oxygen atoms interconnecting the hydrocarbon moieties.
  • the monovalent hydrocarbon radicals represented by R, R, R" and R' are alkyl groups of the formula C l-I such as methyl, ethylpropyl, butylhexyl, octyl, decyl, dodecyl and their isomers, etc; alkenyl groups of the formula C l-I wherein a is as previously defined, such as ethenyl, propenyl, butenyl, octenyl, dodecenyl and their isomers, etc; aryl groups containing six through carbon atoms such as phenyl, tolyl, xylyl, ethylphenyl, diethylphenyl and the like; aralkyl groups such as benzyl, phenylethyl, phenylpropyl, dimethylphenylpropyl, dimethylphenylbutyl and the like; and the halogenated derivatives thereof
  • halogen as employed herein is meant fluorine, chlorine, bromine and iodine.
  • R, R, R" and R' are those of the formula RO-(R O),,,R wherein R is alkylene or alkoxy alkylene of not more than eight carbon atoms; R is alkylene of not more than four carbon atoms; R is selected from the group consisting of alkyl and alkenyl of not more than six carbon atoms; and m is an integer from 0 to 2.
  • R'O [R O]m R are alkoxyalkyl, alkenoxyalkyl, alkoxyalkoxyalkyl, alkenoxyalkoxyalkyl, dialkoxyalkyl, alkenoxy(alkoxy)alkyl, alkenoxyalkoxy(alkoxy)alkyl and alkoxyalkoxy(alkoxy)alkenyl such as 2-methoxyethyl, 4-ethoxy-2-methylbutyl, 2- ethoxyethyl, 2-propoxypropyl, 4-methoxybutyl, 4-methoxy-2-ethylbutyl, 2-butoxybutyl, 2- allyloxyethyl, Z-butenoxyethyl, 4-butenoxybutyl, 2-(2-methoxyethoxy)ethyl, 2-(2-ethoxy-ethoxy) ethyl, 2-(3-methoxypropoxy)propyl, 2-(3-allyloxypropoxy)-
  • EXAMPLE 1 This example was conducted in a glass frit divided electrolytic cell.
  • the anolyte consisted of l.l8g. of the tetraethylester of N-phosphonomethylimino diacetic acid dissolved in fifty milliliters of acetonitrile containing 0.2m.ammonium hexafluorophosphate.
  • the catholyte was 0.2m. NH, PF in acetonitrile.
  • the anode was platinum foil, the cathode platinum, and a saturated calomel reference electrode was in the anode compartment.
  • the electrolysis was conducted at +1 .6v vs. saturated calomel electrode.
  • the initial current was 30ma and after 5 hours had dropped to less than 3ma and 0.002 Faradays of electricity had been passed.
  • the anolyte was concentrated on a rotary evaporator. A portion of the residue was hydrolyzed in 20% hydrochloric acid by refluxing for 1 hour. Nuclear'magnetic spectral analysis indicated that the residue was a 2 to 1 mixture of N-phosphonomethylimino diacetic acid and N- phosphonomethyl glycine indicating that a 33% conversion of the tetra ester to triester had been accomplished.
  • a process for producing a triester of N- phosphonomethyl glycine which comprises subjecting a solution of a tetra ester of N-phosphonomethylimino diacetic acid in an organic solvent containing a supporting electrolyte to a direct electric current at a current density of about 0.0] to about ma/cm whereby said tetra ester is oxidized to the triester, said solvent being one in which the tetra ester and the supporting electrolyte is soluble.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US413476A 1973-11-07 1973-11-07 Process for producing n-phosphonomethyl glycine triesters Expired - Lifetime US3859183A (en)

Priority Applications (31)

Application Number Priority Date Filing Date Title
US413476A US3859183A (en) 1973-11-07 1973-11-07 Process for producing n-phosphonomethyl glycine triesters
IL45990A IL45990A (en) 1973-11-07 1974-11-04 Process for the production of N-phosphonomethyl glycine triesters
EG493/74A EG11633A (en) 1973-11-07 1974-11-05 Process for producing n-phosphonomethylglycine triesters
ES431642A ES431642A1 (es) 1973-11-07 1974-11-05 Un procedimiento para producir un triester de n-fosfonome- tilglicina.
NLAANVRAGE7414397,A NL173773C (nl) 1973-11-07 1974-11-05 Werkwijze voor de bereiding van triesters van n-fosfonomethylglycine.
CS7559A CS177191B2 (it) 1973-11-07 1974-11-06
IT29168/74A IT1025475B (it) 1973-11-07 1974-11-06 Procedimento per la produzione ditriesteri della n fosfonometil clicina
YU2974/74A YU39930B (en) 1973-11-07 1974-11-06 Process for obtaining n-phosphonomethylglycine
IN2439/CAL/1974A IN140891B (it) 1973-11-07 1974-11-06
RO80441A RO72486B (ro) 1973-11-07 1974-11-06 Procedeu de preparare a triesterului n-fosfonometilglicinei
SE7413908A SE401926B (sv) 1973-11-07 1974-11-06 Forfarande for framstellning av n-fosfonometylglycintriestrar genom elektrolytisk ocidering av tetraestrar av n-(fosfonometyl)imino-di-ettiksyra
PL1974175374A PL92408B1 (it) 1973-11-07 1974-11-06
BR9282/74A BR7409282A (pt) 1973-11-07 1974-11-06 Processo para producao de triesteres de n-fosfonometil-glicina
CA213,144A CA1030900A (en) 1973-11-07 1974-11-06 Process for producing n-phosphonomethyl glycine triesters
CH1483874A CH615932A5 (it) 1973-11-07 1974-11-06
FR7436868A FR2249974B1 (it) 1973-11-07 1974-11-06
AU75087/74A AU492150B2 (en) 1973-11-07 1974-11-06 Process for producing phosphonomethyl glycine thiesters
AT889074A AT337206B (de) 1973-11-07 1974-11-06 Verfahren zur herstellung von triestern des n-phosphonomethylglycins
DD182198A DD116237A5 (it) 1973-11-07 1974-11-06
BG028135A BG27092A3 (bg) 1973-11-07 1974-11-06 Метод за получаване на n-фосфонометилглицинови триестери
GB4791574A GB1452644A (en) 1973-11-07 1974-11-06 Production of n-phosphonomethyl glycine triesters
PH16491A PH10866A (en) 1973-11-07 1974-11-06 Process for producing n-phosphonomethyl glycine triesters
BE150245A BE821891A (fr) 1973-11-07 1974-11-06 Procede de production de triesters de n-phosphonomethylglycine et nouveaux produits ainsi obtenus
DK577674AA DK140897B (da) 1973-11-07 1974-11-06 Fremgangsmåde til fremstilling af en triester af N-phosphonomethylglycin.
JP12724074A JPS5441573B2 (it) 1973-11-07 1974-11-06
DE19742452701 DE2452701C3 (de) 1973-11-07 1974-11-06 Verfahren zur Herstellung eines Triesters von N-Phosphonomethylglycin durch elektrolytische Oxydation des entsprechenden Tetraesters der N-(PhosphonmethyD-iminodiessigsäure
IE2284/74A IE40538B1 (en) 1973-11-07 1974-11-06 Production of n-phosphonomethyl glycine triesters
HU74MO00000922A HU171934B (hu) 1973-11-07 1974-11-06 Sposob poluchenija tri-slozhnykh ehfirov n-fosfonometilglicina
AR256425A AR216279A1 (es) 1973-11-07 1974-11-06 Procedimiento para producir un triester de n-fosfonometilglicina convertible en n-fosfonometilglicina,la cual es util como herbicida de post-emergencia
ZA00747144A ZA747144B (en) 1973-11-07 1974-11-06 Process for producing n-phosphonomethyl glycine triesters
MY41/78A MY7800041A (en) 1973-11-07 1978-12-30 Production of n-phosphonomethyl glycine triesters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US413476A US3859183A (en) 1973-11-07 1973-11-07 Process for producing n-phosphonomethyl glycine triesters

Publications (1)

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US3859183A true US3859183A (en) 1975-01-07

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US413476A Expired - Lifetime US3859183A (en) 1973-11-07 1973-11-07 Process for producing n-phosphonomethyl glycine triesters

Country Status (29)

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US (1) US3859183A (it)
JP (1) JPS5441573B2 (it)
AR (1) AR216279A1 (it)
AT (1) AT337206B (it)
BE (1) BE821891A (it)
BG (1) BG27092A3 (it)
BR (1) BR7409282A (it)
CA (1) CA1030900A (it)
CH (1) CH615932A5 (it)
CS (1) CS177191B2 (it)
DD (1) DD116237A5 (it)
DK (1) DK140897B (it)
EG (1) EG11633A (it)
ES (1) ES431642A1 (it)
FR (1) FR2249974B1 (it)
GB (1) GB1452644A (it)
HU (1) HU171934B (it)
IE (1) IE40538B1 (it)
IL (1) IL45990A (it)
IN (1) IN140891B (it)
IT (1) IT1025475B (it)
MY (1) MY7800041A (it)
NL (1) NL173773C (it)
PH (1) PH10866A (it)
PL (1) PL92408B1 (it)
RO (1) RO72486B (it)
SE (1) SE401926B (it)
YU (1) YU39930B (it)
ZA (1) ZA747144B (it)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120689A (en) * 1975-12-29 1978-10-17 Monsanto Company Benzyl and aryl esters of N-phosphonomethyl glycines, herbicidal compositions and use thereof
US4127455A (en) * 1976-08-09 1978-11-28 Basf Aktiengesellschaft Manufacture of symmetrical carotenoids
CN104262393A (zh) * 2014-07-08 2015-01-07 重庆紫光化工股份有限公司 一种草甘膦的节能清洁生产方法及装置

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978392A (en) * 1957-08-12 1961-04-04 Celanese Corp Electrolytic process
US3137705A (en) * 1960-04-08 1964-06-16 Ciba Geigy Corp Hydroxylamino compounds
US3649484A (en) * 1969-04-09 1972-03-14 Uniroyal Inc Electrolytic process for the manufacture of azo compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978392A (en) * 1957-08-12 1961-04-04 Celanese Corp Electrolytic process
US3137705A (en) * 1960-04-08 1964-06-16 Ciba Geigy Corp Hydroxylamino compounds
US3649484A (en) * 1969-04-09 1972-03-14 Uniroyal Inc Electrolytic process for the manufacture of azo compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120689A (en) * 1975-12-29 1978-10-17 Monsanto Company Benzyl and aryl esters of N-phosphonomethyl glycines, herbicidal compositions and use thereof
US4127455A (en) * 1976-08-09 1978-11-28 Basf Aktiengesellschaft Manufacture of symmetrical carotenoids
CN104262393A (zh) * 2014-07-08 2015-01-07 重庆紫光化工股份有限公司 一种草甘膦的节能清洁生产方法及装置
CN104262393B (zh) * 2014-07-08 2017-01-11 重庆紫光化工股份有限公司 一种草甘膦的节能清洁生产方法及装置

Also Published As

Publication number Publication date
EG11633A (en) 1977-09-30
DE2452701A1 (de) 1975-05-15
YU297474A (en) 1982-06-30
FR2249974A1 (it) 1975-05-30
CA1030900A (en) 1978-05-09
BG27092A3 (bg) 1979-08-15
BR7409282A (pt) 1976-05-11
IE40538B1 (en) 1979-06-20
ATA889074A (de) 1976-10-15
DK577674A (it) 1975-07-07
DK140897C (it) 1980-05-12
MY7800041A (en) 1978-12-31
YU39930B (en) 1985-06-30
IN140891B (it) 1977-01-01
AU7508774A (en) 1976-05-06
DE2452701B2 (de) 1977-03-31
PL92408B1 (it) 1977-04-30
NL173773B (nl) 1983-10-03
RO72486B (ro) 1983-04-30
IE40538L (en) 1975-05-07
SE401926B (sv) 1978-06-05
PH10866A (en) 1977-09-16
AT337206B (de) 1977-06-27
HU171934B (hu) 1978-04-28
JPS5077320A (it) 1975-06-24
FR2249974B1 (it) 1976-10-22
IL45990A0 (en) 1975-02-10
CH615932A5 (it) 1980-02-29
NL173773C (nl) 1984-03-01
ES431642A1 (es) 1976-11-01
JPS5441573B2 (it) 1979-12-08
IT1025475B (it) 1978-08-10
DK140897B (da) 1979-12-03
AR216279A1 (es) 1979-12-14
IL45990A (en) 1977-02-28
ZA747144B (en) 1975-11-26
BE821891A (fr) 1975-05-06
NL7414397A (nl) 1975-05-12
GB1452644A (en) 1976-10-13
CS177191B2 (it) 1977-07-29
DD116237A5 (it) 1975-11-12
RO72486A (ro) 1983-04-29
SE7413908L (it) 1975-05-09

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