CA1265154A - Procede de preparation des tetrahydro-1,1,2,2 perfluoroalcanols et de leurs esters - Google Patents
Procede de preparation des tetrahydro-1,1,2,2 perfluoroalcanols et de leurs estersInfo
- Publication number
- CA1265154A CA1265154A CA000555009A CA555009A CA1265154A CA 1265154 A CA1265154 A CA 1265154A CA 000555009 A CA000555009 A CA 000555009A CA 555009 A CA555009 A CA 555009A CA 1265154 A CA1265154 A CA 1265154A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- moles
- ester
- hydrogen peroxide
- iodide
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 150000002148 esters Chemical class 0.000 title claims abstract description 25
- 230000002194 synthesizing effect Effects 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 16
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 29
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims 2
- PDJAZCSYYQODQF-UHFFFAOYSA-N iodine monofluoride Chemical compound IF PDJAZCSYYQODQF-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 150000002978 peroxides Chemical class 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- -1 Hydroxide peroxide Chemical class 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NVVZEKTVIXIUKW-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCI NVVZEKTVIXIUKW-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/38—Halogenated alcohols containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/40—Halogenated alcohols perhalogenated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8617983 | 1986-12-22 | ||
| FR8617983 | 1986-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1265154A true CA1265154A (fr) | 1990-01-30 |
Family
ID=9342164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000555009A Expired - Lifetime CA1265154A (fr) | 1986-12-22 | 1987-12-21 | Procede de preparation des tetrahydro-1,1,2,2 perfluoroalcanols et de leurs esters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4791223A (enExample) |
| EP (1) | EP0275771B1 (enExample) |
| JP (1) | JPS63166840A (enExample) |
| KR (1) | KR910000250B1 (enExample) |
| AT (1) | ATE45346T1 (enExample) |
| AU (1) | AU599734B2 (enExample) |
| CA (1) | CA1265154A (enExample) |
| DE (1) | DE3760417D1 (enExample) |
| DK (1) | DK672687A (enExample) |
| ES (1) | ES2010714B3 (enExample) |
| FI (1) | FI875684L (enExample) |
| NO (1) | NO165188C (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO166122C (no) * | 1986-12-22 | 1991-06-05 | Atochem | Fremgangsmaate for fremstilling av en blanding av 1,1,2,2-tetrahydroperfluoralkanoler og deres estere. |
| US5852148A (en) * | 1991-07-10 | 1998-12-22 | Minnesota Mining & Manufacturing Company | Perfluoroalkyl halides and derivatives |
| CA2071596A1 (en) * | 1991-07-10 | 1993-01-11 | Frederick E. Behr | Perfluoroalkyl halides and derivatives |
| US6048952A (en) | 1991-07-10 | 2000-04-11 | 3M Innovative Properties Company | Perfluoroalkyl halides and derivatives |
| JP4525884B2 (ja) * | 1999-05-12 | 2010-08-18 | ダイキン工業株式会社 | 含フッ素アルコール化合物製造用触媒及び含フッ素アルコール化合物の製造方法 |
| DE102004006103A1 (de) * | 2004-02-06 | 2005-10-20 | Voith Fabrics Patent Gmbh | Modular aufgebaute Papiermaschinenbespannung |
| EP1757574A4 (en) * | 2004-04-26 | 2008-04-09 | Daikin Ind Ltd | PROCESS FOR PREPARING FLUORIZED (METH) ACRYLIC ACID ESTERS |
| US20070232766A1 (en) * | 2004-04-26 | 2007-10-04 | Takeomi Hirasaka | Method for Producing Fluorine-Containing Acrylic Ester |
| JPWO2005102983A1 (ja) * | 2004-04-26 | 2008-03-13 | ダイキン工業株式会社 | 含フッ素アクリル酸エステルの製造方法 |
| US8212064B2 (en) * | 2008-05-14 | 2012-07-03 | E.I. Du Pont De Nemours And Company | Ethylene tetrafluoroethylene intermediates |
| US8318877B2 (en) * | 2008-05-20 | 2012-11-27 | E.I. Du Pont De Nemours And Company | Ethylene tetrafluoroethylene (meth)acrylate copolymers |
| EP3933963B1 (de) | 2020-07-01 | 2025-09-24 | VARTA Microbattery GmbH | Verfahren und anlage zur herstellung elektrochemischer zellen sowie elektrode für eine elektrochemische zelle |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239557A (en) * | 1962-01-18 | 1966-03-08 | Du Pont | Process for converting halides to esters |
| CA1023768A (en) * | 1972-12-21 | 1978-01-03 | Horst Jager | Polyfluoroalkyl iodides, process for their manufacture, and their use |
| FR2463113A1 (fr) * | 1979-08-08 | 1981-02-20 | Ugine Kuhlmann | Procede de preparation des 1,1,2,2, tetrahydro perfluoro alcanols et des esters de ces alcools |
| DE3035641A1 (de) * | 1980-09-20 | 1982-05-06 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von perfluoralkyl-alkanolen |
| JPS59141538A (ja) * | 1983-02-01 | 1984-08-14 | Agency Of Ind Science & Technol | ハロゲン化プロピオン酸エステルの製法 |
| NO166122C (no) * | 1986-12-22 | 1991-06-05 | Atochem | Fremgangsmaate for fremstilling av en blanding av 1,1,2,2-tetrahydroperfluoralkanoler og deres estere. |
-
1987
- 1987-11-26 NO NO874942A patent/NO165188C/no unknown
- 1987-12-04 US US07/128,825 patent/US4791223A/en not_active Expired - Fee Related
- 1987-12-18 DE DE8787402923T patent/DE3760417D1/de not_active Expired
- 1987-12-18 EP EP87402923A patent/EP0275771B1/fr not_active Expired
- 1987-12-18 AT AT87402923T patent/ATE45346T1/de not_active IP Right Cessation
- 1987-12-18 ES ES87402923T patent/ES2010714B3/es not_active Expired
- 1987-12-21 CA CA000555009A patent/CA1265154A/fr not_active Expired - Lifetime
- 1987-12-21 DK DK672687A patent/DK672687A/da not_active Application Discontinuation
- 1987-12-21 AU AU82874/87A patent/AU599734B2/en not_active Ceased
- 1987-12-22 KR KR1019870014098A patent/KR910000250B1/ko not_active Expired
- 1987-12-22 JP JP62325105A patent/JPS63166840A/ja active Granted
- 1987-12-22 FI FI875684A patent/FI875684L/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK672687D0 (da) | 1987-12-21 |
| DK672687A (da) | 1988-06-23 |
| NO165188C (no) | 1991-01-09 |
| NO874942D0 (no) | 1987-11-26 |
| FI875684A7 (fi) | 1988-06-23 |
| FI875684A0 (fi) | 1987-12-22 |
| EP0275771B1 (fr) | 1989-08-09 |
| FI875684L (fi) | 1988-06-23 |
| NO165188B (no) | 1990-10-01 |
| AU599734B2 (en) | 1990-07-26 |
| AU8287487A (en) | 1988-06-23 |
| DE3760417D1 (en) | 1989-09-14 |
| US4791223A (en) | 1988-12-13 |
| NO874942L (no) | 1988-06-23 |
| ES2010714B3 (es) | 1989-12-01 |
| JPH0416451B2 (enExample) | 1992-03-24 |
| JPS63166840A (ja) | 1988-07-11 |
| KR880007415A (ko) | 1988-08-27 |
| KR910000250B1 (ko) | 1991-01-23 |
| ATE45346T1 (de) | 1989-08-15 |
| EP0275771A1 (fr) | 1988-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |