JPS6254093B2 - - Google Patents
Info
- Publication number
- JPS6254093B2 JPS6254093B2 JP53026088A JP2608878A JPS6254093B2 JP S6254093 B2 JPS6254093 B2 JP S6254093B2 JP 53026088 A JP53026088 A JP 53026088A JP 2608878 A JP2608878 A JP 2608878A JP S6254093 B2 JPS6254093 B2 JP S6254093B2
- Authority
- JP
- Japan
- Prior art keywords
- phenoxytoluene
- phenoxybenzylidene
- compound
- azobisisobutyronitrile
- carbon tetrachloride
- 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
Links
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 34
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims description 26
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 18
- -1 monocyclic aromatic hydrocarbons Chemical class 0.000 claims description 17
- XGCVFGOKEISJGC-UHFFFAOYSA-N 1-(dibromomethyl)-3-phenoxybenzene Chemical compound BrC(Br)C1=CC=CC(OC=2C=CC=CC=2)=C1 XGCVFGOKEISJGC-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- JOVSDWRNVGOQNK-UHFFFAOYSA-N 1-(dichloromethyl)-3-phenoxybenzene Chemical compound ClC(Cl)C1=CC=CC(OC=2C=CC=CC=2)=C1 JOVSDWRNVGOQNK-UHFFFAOYSA-N 0.000 claims description 9
- 230000002140 halogenating effect Effects 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- WCOYPFBMFKXWBM-UHFFFAOYSA-N 1-methyl-2-phenoxybenzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1 WCOYPFBMFKXWBM-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006251 dihalogenation reaction Methods 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- IMPIIVKYTNMBCD-UHFFFAOYSA-N 2-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1=CC=CC=C1 IMPIIVKYTNMBCD-UHFFFAOYSA-N 0.000 description 1
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7706941A FR2383153A1 (fr) | 1977-03-09 | 1977-03-09 | Nouveaux halogenures de benzylidene, procede de preparation et application a la preparation du metaphenoxy benzaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53112824A JPS53112824A (en) | 1978-10-02 |
| JPS6254093B2 true JPS6254093B2 (xx) | 1987-11-13 |
Family
ID=9187808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2608878A Granted JPS53112824A (en) | 1977-03-09 | 1978-03-09 | Novel halobenzylidene process for preparing same and process for preparing mmphenoxybenzaldehyde |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS53112824A (xx) |
| AT (1) | AT356081B (xx) |
| BE (1) | BE864674A (xx) |
| CA (1) | CA1111447A (xx) |
| CH (1) | CH628605A5 (xx) |
| DE (1) | DE2810305A1 (xx) |
| DK (1) | DK164783C (xx) |
| ES (1) | ES467646A1 (xx) |
| FR (1) | FR2383153A1 (xx) |
| GB (1) | GB1602161A (xx) |
| HU (1) | HU180060B (xx) |
| IE (1) | IE46430B1 (xx) |
| IT (1) | IT1101829B (xx) |
| LU (1) | LU79194A1 (xx) |
| NL (1) | NL189189C (xx) |
| SE (2) | SE7802318L (xx) |
| SU (1) | SU1028245A3 (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH641435A5 (en) * | 1979-01-03 | 1984-02-29 | Shell Int Research | Process for the preparation of 3-phenoxybenzaldehyde |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4994639A (xx) * | 1973-01-19 | 1974-09-09 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085147A (en) * | 1976-02-05 | 1978-04-18 | Shell Oil Company | Preparation of meta-aryloxy-benzaldehydes |
| GB1588517A (en) * | 1976-10-06 | 1981-04-23 | Shell Int Research | Preparation of m-aryloxybenzyl chloride and m-aryloxybenzal chloride |
| DE2707232A1 (de) * | 1977-02-19 | 1978-08-24 | Bayer Ag | Verfahren zur herstellung halogenmethylierter diphenylaether |
-
1977
- 1977-03-09 FR FR7706941A patent/FR2383153A1/fr active Granted
-
1978
- 1978-02-22 SU SU782582817A patent/SU1028245A3/ru active
- 1978-03-01 SE SE7802318A patent/SE7802318L/xx unknown
- 1978-03-03 NL NLAANVRAGE7802393,A patent/NL189189C/xx not_active IP Right Cessation
- 1978-03-08 IT IT48347/78A patent/IT1101829B/it active
- 1978-03-08 CA CA298,509A patent/CA1111447A/fr not_active Expired
- 1978-03-08 ES ES467646A patent/ES467646A1/es not_active Expired
- 1978-03-08 LU LU79194A patent/LU79194A1/xx unknown
- 1978-03-08 IE IE470/78A patent/IE46430B1/en not_active IP Right Cessation
- 1978-03-08 DK DK102178A patent/DK164783C/da active
- 1978-03-08 BE BE185753A patent/BE864674A/xx not_active IP Right Cessation
- 1978-03-08 GB GB9247/78A patent/GB1602161A/en not_active Expired
- 1978-03-09 AT AT170478A patent/AT356081B/de not_active IP Right Cessation
- 1978-03-09 HU HU78RO968A patent/HU180060B/hu not_active IP Right Cessation
- 1978-03-09 JP JP2608878A patent/JPS53112824A/ja active Granted
- 1978-03-09 DE DE19782810305 patent/DE2810305A1/de active Granted
- 1978-03-09 CH CH258478A patent/CH628605A5/fr not_active IP Right Cessation
-
1983
- 1983-10-27 SE SE8305906A patent/SE8305906L/sv not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4994639A (xx) * | 1973-01-19 | 1974-09-09 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53112824A (en) | 1978-10-02 |
| DK164783B (da) | 1992-08-17 |
| SE8305906D0 (sv) | 1983-10-27 |
| ATA170478A (de) | 1979-09-15 |
| DK164783C (da) | 1993-01-04 |
| CH628605A5 (en) | 1982-03-15 |
| IT7848347A0 (it) | 1978-03-08 |
| SE7802318L (sv) | 1978-09-10 |
| IE780470L (en) | 1978-09-09 |
| HU180060B (en) | 1983-01-28 |
| DE2810305C2 (xx) | 1990-03-08 |
| DK102178A (da) | 1978-09-10 |
| FR2383153A1 (fr) | 1978-10-06 |
| GB1602161A (en) | 1981-11-11 |
| SE8305906L (sv) | 1983-10-27 |
| NL7802393A (nl) | 1978-09-12 |
| FR2383153B1 (xx) | 1980-03-21 |
| DE2810305A1 (de) | 1978-09-14 |
| IT1101829B (it) | 1985-10-07 |
| SU1028245A3 (ru) | 1983-07-07 |
| ES467646A1 (es) | 1978-12-01 |
| LU79194A1 (fr) | 1978-11-27 |
| NL189189B (nl) | 1992-09-01 |
| AT356081B (de) | 1980-04-10 |
| IE46430B1 (en) | 1983-06-01 |
| BE864674A (fr) | 1978-09-08 |
| NL189189C (nl) | 1993-02-01 |
| CA1111447A (fr) | 1981-10-27 |
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