US3657099A - Electrolytic cell for producing adiponitrile by electrolytic hydrodimerization of acrylonitrile - Google Patents

Electrolytic cell for producing adiponitrile by electrolytic hydrodimerization of acrylonitrile Download PDF

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Publication number
US3657099A
US3657099A US33630A US3657099DA US3657099A US 3657099 A US3657099 A US 3657099A US 33630 A US33630 A US 33630A US 3657099D A US3657099D A US 3657099DA US 3657099 A US3657099 A US 3657099A
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Prior art keywords
electrolytic cell
duct
electrode
cathode
membrane
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US33630A
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English (en)
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Maomi Seko
Akira Yomiyama
Tetsuya Miyake
Koji Nakagawa
Muneo Yoshida
Koji Inada
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Asahi Kasei Corp
Asahi Chemical Industry Co Ltd
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Asahi Chemical Industry Co Ltd
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    • 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
    • C25B3/29—Coupling reactions
    • C25B3/295—Coupling reactions hydrodimerisation

Definitions

  • ABSTRACT An electrolytic cell for producing adiponitrile by electrolytic hydrodimerization of acrylonitrile, which comprises one or more sets of an anode plate, a cation exchange membrane and a cathode plate superposed with each other, and at least one duct formed between said anode plate and said membrane and between said cathode plate and said membrane through which electrolyte is passed at a high flowing rate, said duct having at least one turning portion which is positioned outside of an electric current path flowing across the anode and cathode plates.
  • the present invention relates to a construction of an electrolytic cell for producing adiponitrile by electrolytic hydrodimerization of acrylonitrile.
  • acrylonitrile and adiponitrile are easily oxidized to be lost and hydrogen cyanide gas is produced at the anode area of an electrolytic cell. Furthermore, gaseous mixtures of oxygen and acrylonitrile produced at the anode area may cause explosion, which is dangerous Accordingly, it is desired to separate anode and cathode chambers by means of a sheet of membrane.
  • a surface of the cathode becomes alkaline, and at this surface layer bis-cyanoethyl-ether is produced by reaction of acrylonitrile and water. Further hydrolysis products of acrylonitrile and adiponitrile and propionitrile are produced at this surface layer.
  • a dual-electrode type electrolytic cell includes a plurality of unit cells which are superposed with each other and electrically connected in series, and consequently high voltage can be applied thereto, so that rectification efficiency is increased, with a transformer having reduced capacity, which is economical.
  • electrolyte is usually fed to the cells of the respective units separately, so that current leakage may occur through pipings for feeding the electrolyte.
  • the current leakage is of course undesirable in itself because it produces loss of current, and it is particularly undesirable for electrolysis of acrylonitrile because hydrogen cyanide and the explosive oxygen and acrylonitrile gas mixture may be produced and a part of the piping may be abnormally corroded since a part of cathode works as an anode because of the current leakage. If highly conductive liquid such as sulfuric acid is used as anolyte the current leakage is further increased and a dangerous gas mixture of hydrogen and oxygen may be produced.
  • the duct for passing electrolyte on the cathode surface comprises only straight portions through which the electrolyte uniformly flows.
  • the electrolytic cell comprises an anode chamber and a cathode chamber separated by a membrane, the cathode chamber providing at least one duct for passing electrolyte, said at least one duct preferably having a rectangular shape in the cross section and being formed by the electrode, the membrane and a spacer for holding uniform the distance between the electrode and the membrane, with no obstacle being formed in said duct.
  • the duct has a width of 0.5 to 50 cm. in the direction of flow therein.
  • the duct has at least one turning portion so that the entire length of the duct in the perpendicular direction of flow is made longer than the length of one side of the electrode, and electric current is applied only on the straight portions of the duct.
  • the electrolytic cell is a dual-electrode type cell in which a duct for passing electrolyte comprises straight portions situated on the cathode surface and turning portions around the periphery of the electrode, so that electric current does not pass through the turning portions.
  • a duct for passing electrolyte comprises straight portions situated on the cathode surface and turning portions around the periphery of the electrode, so that electric current does not pass through the turning portions.
  • the membrane may be made of any material which can prevent acrylonitrile and adiponitrile from diffusing into the anode chamber and has high conductivity, a cationexchange membrane is preferred.
  • a sulphonic type cationexchange membrane based on styrene-divinyl benzene is superior in chemical stability and mechanical strength, and can be used in a reinforced form with any reinforcement such as glass fiber or a homogeneous form having no reinforcement.
  • the membrane having thickness of 0.5 to 2 mm. is used to prevent the diffusion of acrylonitrile or other material and to provide necessary mechanical strength.
  • the cathode may be made from lead, lead alloy, cadmium, zinc, carbon or the like. More particularly, lead-antimony, lead-silver, lead-antimony or like alloys which can be also used as anode material may be advantageously used in the dual-electrode type cell since such material can be used as an anode at one side and as a cathode at the other side.
  • the anode may be made from lead peroxide, lead, lead alloy such as lead-antimony, lead-silver, lead-antimony-silver or ferrous oxide, carbon, platinum or the like.
  • the anolyte is preferably an acidic solution, particularly, sulfuric acid solution, where lead alloy which is superior in corrosion resistant property is used as the anode material.
  • an electrode acts as an anode at one side and a cathode at the other side, so that the electrode can be made as a single piece when the same material is used as the anode and cathode.
  • the anode and cathode plates are connected together to form a dual-electrode.
  • an electrode frame of insulating material which has an anode plate and a cathode plate attached to the opposite sides of said frame and electrically connected together by a rod passing through the frame.
  • a spacer may be provided to hold the cathode plate and the membrane at uniform distance. If the distance between the cathode plate and the membrane is extremely small, there is a danger of these parts coming into contact with each other, while if the distance is extremely large the required voltage is increased and the required volume of flow is also increased.
  • the desired distance is between 0.5 and mm.
  • the spacer contacting with the cathode surface is made in the form of a straight strip arranged in parallel relationship.
  • the strip has practically 2 to 20 mm. width. If the distance between the strips is too great, the membrane may come into contact with the electrode, while if the distance is to little, the pressure loss is excessively increased. Therefore, the preferable distance is 0.5 to 50 cm.
  • the duct is formed between the strips which serves as spacers positioned between the cathode plate and the membrane.
  • the catholyte flows in the duct as a straight flow.
  • the length of one side of the electrode is about 20 cm. to 2 m., in industrial equipment.
  • the flow of the electrolyte has at least one turning portion so as to make the entire length of the duct longer than the length of said one side of the electrode, and the turning portion is positioned at the outside of the cathode plate, so as to prevent electric current from passing through the turning portion.
  • the turning portion may be provided within the thickness of the spacer, or it may be carved in the electrode frame outside the periphery of the electrode plate. In the latter case, it is essential to form the duct in such shape that the eddy current produced in the turning portion exerts substantially no effect over the flow in the straight portions.
  • the turning portions and the straight portions may be connected successively so as to form a single duct, but pressure loss may be excessively increased in a large scale electrolytic cell.
  • two or more sets of ducts may be provided.
  • the feeding pressure of the electrolyte should be maintained below kg./cm. at the inlet side.
  • the anode chamber is preferably made in the similar construction with that of the cathode chamber. If the both constructions are identical, the pressure losses in these chambers are equal when the flowing rates are maintained at the same value, so that the differential pressure acting on the membrane becomes null.
  • the differential pressure should be below 1 kg./cm. preferably below 0.3 kg./cm.
  • the anode chamber requires less accuracy than the cathode chamber, so that a reinforcing porous plate or screen may be set in the anode chamber at the side of the membrane for the purpose of facilitating the discharge of gas or sludge produced in the anode chamber.
  • the electrolyte can be fed into the anode and cathode chambers through noales provided around the electrode frame.
  • the respective nozzles are connected to conduits having sufficiently long distance and sufficiently small diameter to maintain the current leakage outside of the cell to low value, and the electrolyte is fed through a header thereto.
  • the current leakage is preferably maintained at 5 percent or less.
  • conduits may be formed in the peripheral portions of superposed unit cells, and slits may be formed to connect said conduits to the ducts on the cathode and anode surfaces, whereby the catholyte and anolyte can be fed.
  • slits In order to reduce the current leakage the slits should be as long and fine as possible.
  • the spacer, the electrode frame and the conduits may be made from any material which is electrically insulating and corrosion-resistant to the catholyte and anolyte, such as polypropylene, rubber, heat-resistant vinyl-chloride, vinylchloride or the like.
  • FIGS. 1a, 1b, 1c and 1d illustrate a first embodiment of the present invention
  • FIG. 1a being an exploded perspective view of the electrolytic cell
  • FIG. 1b being an exploded perspective view of one set of components of the cell, namely electrode plates, spacers and a membrane
  • FIG. 1c being front views of these components
  • FIG. 1d being an enlarged sectional view of the set of the components
  • FIGS. 20, 2b and 2c illustrate a second embodiment of the present invention, FIG. 20 being an exploded perspective view of one set of components of the electrolytic cell, FIG. 2b being front views of these components and FIG. 2c being an enlarged sectional view of the set of the components;
  • FIGS. 3a, 3b and 3c illustrate a third embodiment of the present invention, FIG. 3a being an exploded perspective view of one set of components of the electrolytic cell, FIG. 3b being front views of the components and FIG. 30 being an enlarged sectional view of the set of the components;
  • FIGS. 4a, 4b and 4 c illustrate a fourth embodiment of the present invention, FIG. 4a being an exploded perspective view of one set of components of the cell, FIG. 4b being front views of the components and FIG. 40 being an enlarged sectional view of the set of the components; and
  • FIGS. 5a, 5b and 5c illustrate a fifth embodiment of the present invention, FIG. 5a being an exploded perspective view of a set of components of the cell, FIG. 5b being front views of the components and FIG. 5c being an enlarged sectional view of the set of the components.
  • FIGS. la, 1b, 1c and 1d illustrate a first embodiment of the invention.
  • the electrolytic cell includes electrode frames 1, spacers 2 and cationexchange membranes 3.
  • the frame 1 comprises a board 8 of insulating material and electrode plates 9 fitted in both sides of said board 8 in flush therewith.
  • the electrode plates 9 are electrically connected together by a conductive rod 10 passing through the board 8.
  • the electrode frame 1 has feeding and discharging nozzles 16 at its periphery, through which tunnel-like feeding and discharging ports 11 and 12 extend to the surface of the electrode.
  • the spacer 2 is made of a thin plate of insulating material having substantially the same size as the frame 1 and having a cut-out portion 20 therein to form a duct 19.
  • the frames 1, the spacers 2 and the cation exchange membrane 3 are superposed successively, the respective cut-out portions are enclosed between the electrodes and the membrane to form the duct 19 for the electrolyte.
  • the duct 19 forms essentially one flowing path which leads from the feeding port 11 to the discharging port 12 and includes at least one turning portion, the length of said path being substantially longer than that of one side of said electrode frame.
  • the turning portions are formed at the outside of the electrode plate 9, so that electrolysis occurs only in the straight portions of the duct 19.
  • the width and the thickness of the duct 19 depend on the conditions of the electrolysis and the property of the cation exchange membrane, the width within the range from 0.5 to 50 cm. and the thickness within the range from 0.5 to 5 mm. are employed in practical use.
  • the thickness of the duct 19 is substantially equal to that of the insulating plate 18 used for the spacer 2,
  • the electrolytic cell is fabricated from the above components, as will be described below.
  • a pair of press heads 6 are put with a substantial space therebetween and a pair of anode and cathode frames 4 and 5 respectively are put inside of said press heads 6, as shown in FIG. 1a.
  • Each of the anode and cathode frames 4 and 5 respectively has an electrode plate 9 fitted in one side thereof.
  • the spacers 2, the cation-exchange membranes 3, the spacers 2 and the electrode frames 1 are put in this order successively and they are pressed together by means of the press heads 6 to form the electrolytic cell.
  • one electrolytic cell may include two to several hundred electrode frames to obtain desired capacity, it is preferable in practical use that the one cell includes less than two hundred electrode frames.
  • the above electrolytic cell can be used to perform the electrolytic hydrodimerization of acrylonitrile, as follows.
  • Direct current is applied across the anode and cathode frames 4 and 5, respectively while the catholyte and the anolyte are being fed to a cathode chamber 22 formed by the duct 19 enclosed between the cation-exchange membrane and the cathode, and an anode chamber 23 adjoining to said cathode chamber, respectively.
  • the electrode plates 9 fitted in the electrode frame 1 forms a cathode when it confronts the anode frame 4, while it forms an anode when it confronts the cathode frame 5.
  • no obstruction is formed in the duct 19 and there is no restriction therein as in the electrolytic cell disclosed in Dutch Pat. No. 6,707,472, so that any kind of electrolyte can be used.
  • the electrolytic cell can be used in horizontal position as shown in FIG. 1, vertical position or inclined position at any angle,
  • the distribution of the electrolyte to the electrolytic cell can be made by headers for the anolyte and the catholyte through flexible tubes leading to the respective electrode frames.
  • the flexible tubes In order to prevent the current leakage, the flexible tubes must be as long and small in cross section as possible.
  • the flexible tubes can be made sufiiciently long in length and small in diameter to reduce the current leakage to negligible value, since the volume of the electrolyte flowing one electrode chamber is substantially small.
  • FIGS. 2 and 3 illustrate modified forms of the electrolytic cell according to the present invention.
  • FIG. 2 illustrates a construction which is substantially similar to that shown in FIG. 1, except that portions corresponding to the turning portions of the duct 19 in the spacer 2 shown in FIG. 1 are formed by grooves 14 carved in an electrode frame 1 and a spacer 2 is formed in a shape of a ladder as shown in FIG. 21).
  • FIG. 3 illustrates another construction in which a portion corresponding to the spacer 2 is formed as an integral part of an electrode frame 1, and consequently an electrolytic cell is constituted from two components, namely, electrode frames 1 and cation-exchange membranes 3. Electrolyte passing through a duct 19 flows into a groove 14 formed in the frame at the end of said duct, where it reverses its flowing direction and then flows into a next duct 19. Thus, the electrolyte fed to a feeding port 11 at one end of the electrode frame flows through an essentially single duct having at least one turning portion and it is discharged through a discharging port 12.
  • the width of the duct 19 depends mainly on the surface area of the electrode and the entire length of the duct as required. If the cation-exchange membrane 3 has not sufficient strength to maintain the required width of the duct, one or more fine strips 21 are provided in the duct to prevent the deformation of the membrane.
  • the strip used for such purpose may be made of fine insulating material having the same thickness as that of the spacer 2 and width of 3 to 20 mm., and positioned in parallel with the flowing direction.
  • FIGS. 4 and 5 illustrate other forms of the electrolytic cell according to the present invention, which are somewhat different from those shown in FIGS. 1 to 3.
  • FIG. 4 shows a construction in which an electrode frame 1 is formed of a single electrode plate 9 having feeding and discharging conduits 15 at its peripheral portion.
  • the electrode plate forms an anode at its one side surface and a cathode at its other side surface when current is applied thereto.
  • a spacer 2 used in this construction is made of a thin plate having a cut portion 20 to form a duct 19 having at least one turning portion, which is substantially identical with that shown in FIG. 1, and said spacer has conduits 15 as shown in FIG. 4b.
  • a shield plate 7 having a central opening and feeding and discharging conduits 15 at its peripheral portion is positioned between the spacer 2 and the electrode plate 9, so that the turning portions of the duct 19 are shielded from direct current applied to the cell.
  • the shield plate 7 is made of a thin insulating plate having a thickness of 0.05 to 0.2 mm.
  • the electrolytic cell is fabricated by setting a pair of press heads 6, putting an anode plate 4 and a cathode plate 5 inside of said press heads, in the same manner as shown in FIG. 1, then putting the shield plate 7, the spacer 2, the cationexchange membrane 3, the spacer 2, the shield plate 7 and the electrode plate repeatedly in this order between said anode and cathode plates and pressing these parts together by said press heads.
  • the electrolyte is fed to the respective chambers of the cell through the feeding and discharging conduits 15 and the nozzles 16 extending through the press heads 6.
  • the feeding and discharging conduits extending through the electrode plates 9 must be completely sealed by means of seals 17 at the area contacting with the electrolyte passing through the conduits, in order to prevent the electrolyte from contacting with the electrode plates, which may cause electrolysis.
  • FIG. 5 illustrates another form of the electrolytic cell according to the present invention, which is a modified form of FIG. 4.
  • an electrode frame 1 made from insulating material has a central opening, into which an electrode plate 9 having the same thickness as that of the electrode frame is fixed.
  • the electrolytic cell includes spacers 2 and cation-exchange membranes 3 which are identical with those shown in FIG. 4.
  • the electrode plate 9 has such dimensions as to sufficiently cover only straight portions of a duct 19 to prevent current from flowing through turning portions of the duct.
  • the electrode plate is formed as an integral piece which acts as an anode at one side and a cathode at the other side.
  • the electrode plate 1 has conduits 15 at its peripheral portion, as shown in FIG. 5b, through which electrolyte is fed to the respective chambers.
  • the electrolytic cell includes three components, namely, the electrode frames 1, the spacers 2 and the cation-exchange membranes 3, which are repeatedly superposed with each other to form a cell having any desired capacity.
  • a single electrolytic cell can be formed from two to several hundred electrode plates, it is preferably made from less than two hundred plates in practical use.
  • EXAMPLE 1 The electrolytic cell as shown in FIG. 3 has been operated under the following conditions.
  • Electrode frame Material polypropylene Size: 1,300 X 1,300 X 20 mm.
  • Electrode plate (anode & cathode) Material hard lead Size: 1,220 X 1,140 X 4 mm.
  • Spacer Material polypropylene Size: 1,300 X 1,300 X 2 mm.
  • Cation-exchange membrane Material sulphonate type strong acidic ion exchange membrane based on butadiene copolymer Size: 1,280 X 1,280 X 1.2 mm.
  • Catholyte Material aqueous solution containing acrylonitrile and tetraalkyl ammonium salt as supporting salt Flowing rate: 600 l./hr./chamber Anolyte Material: 2N aqueous solution of sulphuric acid Flowing rate: 550 l./hr./chamber Number of chambers 40 pairs Current 2,200 amp.
  • Example 2 The electrolytic cell and the conditions of operation in Example l were modified as follows:
  • Catholyte Flowing rate 1.7 M /hr./chamber Anolyte Flowing rate: 1.6 M /hr./chamber Number of chambers 10 pairs Current 2,200 amp.
  • EXAMPLE 3 The electrolytic cell as shown in FIG. 5 was operated under the following conditions.
  • Electrode frame Outer frame Material polypropylene Outside size: 1,000 X 1,000 X 6 mm. Inside size: 820 X 810 mm.
  • Electrode plate Size 838 X 828 X 6 mm.
  • Conduits Number 1 for feeding anolyte l for discharging anolyte 1 for feeding catholyte l for discharging catholyte Size: 80 X 30 mm.
  • the outer frame and the electrode plate were connected by stepped joint, with packing material inserted therein to prevent leakage.
  • Spacer Material polypropylene Size: 1,000 X 1,000 X 2 mm.
  • Catholyte Material same as Example 1.
  • An electrolytic cell for producing adiponitrile by electrolytic hydrodimerization of acrylonitrile comprising at least one set of an anode plate, a cathode plate and a membrane superposed between said anode and cathode plates, and at least one duct formed between said membrane and said cathode plate, said at least one duct having at least one turning portion therein to form a substantially longer path for flowing electrolyte than the length of one side of said plate, said turning portion being positioned outside of the path of the current applied across said anode and cathode plates.
  • At least one duct is formed by a spacer having a cut-out portion, said spacer being positioned between said membrane and said

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
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  • Metallurgy (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
US33630A 1969-05-07 1970-05-01 Electrolytic cell for producing adiponitrile by electrolytic hydrodimerization of acrylonitrile Expired - Lifetime US3657099A (en)

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US (1) US3657099A (de)
BR (1) BR7018862D0 (de)
DE (1) DE2022696C3 (de)
FR (1) FR2042464A1 (de)
GB (1) GB1312319A (de)
NL (1) NL151447B (de)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3972793A (en) * 1975-09-26 1976-08-03 Eli Lilly And Company Continuous flow-through mercury cathode electrolysis cell
US4065376A (en) * 1976-05-04 1977-12-27 Diamond Shamrock Corporation Electrolytic cell
US4067794A (en) * 1977-01-14 1978-01-10 Ionics, Inc. Sealing gasket for chamber wall
USRE30864E (en) * 1977-06-27 1982-02-09 Olin Corporation Process for electrolysis in a membrane cell employing pressure actuated uniform spacing
US4432858A (en) * 1981-08-04 1984-02-21 Helmut Schmitt Monopolar filter-press type electrolyzer
US4495048A (en) * 1981-05-22 1985-01-22 The Japan Carlit Co., Ltd. Apparatus for electrolysis of saline water
US4596638A (en) * 1985-04-26 1986-06-24 International Fuel Cells Corporation Method for the electrochemical production of adiponitrile using anodes having NiCo2 O4 catalyst
US4605482A (en) * 1981-04-28 1986-08-12 Asahi Glass Company, Ltd. Filter press type electrolytic cell
US4675254A (en) * 1986-02-14 1987-06-23 Gould Inc. Electrochemical cell and method
US6607655B1 (en) * 1998-09-10 2003-08-19 Institut Fur Mikrotechnik Mainz Gmbh Reactor and method for carrying out electrochemical reactions
CN102400174A (zh) * 2011-11-30 2012-04-04 青岛双瑞海洋环境工程有限公司 电解丙烯腈二聚制备己二腈的新型装置
GB2578292A (en) * 2018-10-17 2020-05-06 Vapourtec Ltd Flow reactor

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2708658A (en) * 1952-07-18 1955-05-17 Ionics Apparatus for removing electrolytes from solutions
US3084113A (en) * 1960-02-01 1963-04-02 Gen Electric Methods of and apparatus for demineralizing water

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2708658A (en) * 1952-07-18 1955-05-17 Ionics Apparatus for removing electrolytes from solutions
US3084113A (en) * 1960-02-01 1963-04-02 Gen Electric Methods of and apparatus for demineralizing water

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3972793A (en) * 1975-09-26 1976-08-03 Eli Lilly And Company Continuous flow-through mercury cathode electrolysis cell
US4065376A (en) * 1976-05-04 1977-12-27 Diamond Shamrock Corporation Electrolytic cell
US4067794A (en) * 1977-01-14 1978-01-10 Ionics, Inc. Sealing gasket for chamber wall
USRE30864E (en) * 1977-06-27 1982-02-09 Olin Corporation Process for electrolysis in a membrane cell employing pressure actuated uniform spacing
US4605482A (en) * 1981-04-28 1986-08-12 Asahi Glass Company, Ltd. Filter press type electrolytic cell
US4495048A (en) * 1981-05-22 1985-01-22 The Japan Carlit Co., Ltd. Apparatus for electrolysis of saline water
US4432858A (en) * 1981-08-04 1984-02-21 Helmut Schmitt Monopolar filter-press type electrolyzer
US4596638A (en) * 1985-04-26 1986-06-24 International Fuel Cells Corporation Method for the electrochemical production of adiponitrile using anodes having NiCo2 O4 catalyst
US4675254A (en) * 1986-02-14 1987-06-23 Gould Inc. Electrochemical cell and method
US6607655B1 (en) * 1998-09-10 2003-08-19 Institut Fur Mikrotechnik Mainz Gmbh Reactor and method for carrying out electrochemical reactions
CN102400174A (zh) * 2011-11-30 2012-04-04 青岛双瑞海洋环境工程有限公司 电解丙烯腈二聚制备己二腈的新型装置
GB2578292A (en) * 2018-10-17 2020-05-06 Vapourtec Ltd Flow reactor

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Publication number Publication date
BR7018862D0 (pt) 1973-04-17
NL151447B (nl) 1976-11-15
GB1312319A (en) 1973-04-04
DE2022696C3 (de) 1975-06-26
DE2022696B2 (de) 1974-11-07
NL7006605A (de) 1970-11-10
DE2022696A1 (de) 1970-11-19
FR2042464A1 (de) 1971-02-12

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