DE3635613A1 - Verfahren zur herstellung von, gegebenenfalls in der 11-stellung substiuierten, 3,7,11-tri-(methyl)-2e,4e-dodecadiensaeuren - Google Patents
Verfahren zur herstellung von, gegebenenfalls in der 11-stellung substiuierten, 3,7,11-tri-(methyl)-2e,4e-dodecadiensaeurenInfo
- Publication number
- DE3635613A1 DE3635613A1 DE3635613A DE3635613A DE3635613A1 DE 3635613 A1 DE3635613 A1 DE 3635613A1 DE 3635613 A DE3635613 A DE 3635613A DE 3635613 A DE3635613 A DE 3635613A DE 3635613 A1 DE3635613 A1 DE 3635613A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- tri
- methyl
- optionally substituted
- mixture
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims description 68
- 238000006317 isomerization reaction Methods 0.000 claims description 32
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 28
- 150000003863 ammonium salts Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- QMVSVDPAWIVPNR-YMOPAIQUSA-N (2e,4e)-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical class CC(C)CCCC(C)C\C=C\C(\C)=C\C(O)=O QMVSVDPAWIVPNR-YMOPAIQUSA-N 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- QMVSVDPAWIVPNR-CFXNRPSHSA-N (2z,4e)-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical class CC(C)CCCC(C)C\C=C\C(\C)=C/C(O)=O QMVSVDPAWIVPNR-CFXNRPSHSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 6
- 239000002516 radical scavenger Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000003464 sulfur compounds Chemical class 0.000 claims description 2
- 150000005826 halohydrocarbons Chemical class 0.000 claims 1
- -1 alkoxy radical Chemical class 0.000 description 33
- MNYBEULOKRVZKY-QQZWAFJOSA-N (2z,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound COC(C)(C)CCCC(C)C\C=C\C(\C)=C/C(O)=O MNYBEULOKRVZKY-QQZWAFJOSA-N 0.000 description 21
- 150000001735 carboxylic acids Chemical class 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 17
- 238000004817 gas chromatography Methods 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 229910003002 lithium salt Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000000475 acetylene derivatives Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229930003633 citronellal Natural products 0.000 description 3
- 235000000983 citronellal Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 150000001261 hydroxy acids Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- UCSIFMPORANABL-SNVBAGLBSA-N (3r)-3,7-dimethyloctanal Chemical compound CC(C)CCC[C@@H](C)CC=O UCSIFMPORANABL-SNVBAGLBSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FDQBRYVHALQXLL-PGMBSLALSA-N (2e,4e)-11-hydroxy-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound CC(O)(C)CCCC(C)C\C=C\C(\C)=C\C(O)=O FDQBRYVHALQXLL-PGMBSLALSA-N 0.000 description 1
- RNPDCAAZAYHCFV-HULFFUFUSA-N (2e,4e)-2-methyldodeca-2,4-dienoic acid Chemical class CCCCCCC\C=C\C=C(/C)C(O)=O RNPDCAAZAYHCFV-HULFFUFUSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- GTRLQRHWPXEBLF-UHFFFAOYSA-N benzyl carbamimidothioate Chemical class NC(=N)SCC1=CC=CC=C1 GTRLQRHWPXEBLF-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 description 1
- WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU854023A HU200583B (en) | 1985-10-18 | 1985-10-18 | Process for producing unsaturated carboxylic acids with 2e, 4e configuration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3635613A1 true DE3635613A1 (de) | 1987-04-23 |
Family
ID=10966563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3635613A Withdrawn DE3635613A1 (de) | 1985-10-18 | 1986-10-20 | Verfahren zur herstellung von, gegebenenfalls in der 11-stellung substiuierten, 3,7,11-tri-(methyl)-2e,4e-dodecadiensaeuren |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS62181233A (it) |
| CS (1) | CS268682B2 (it) |
| DD (1) | DD253994A5 (it) |
| DE (1) | DE3635613A1 (it) |
| ES (1) | ES2002040A6 (it) |
| FI (1) | FI864219A (it) |
| FR (1) | FR2588862A1 (it) |
| GB (1) | GB2181732B (it) |
| HU (1) | HU200583B (it) |
| IT (1) | IT1197887B (it) |
| NL (1) | NL8602620A (it) |
| YU (1) | YU176786A (it) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818047A (en) * | 1972-08-07 | 1974-06-18 | C Henrick | Substituted pyrones |
| FR2265714A1 (en) * | 1974-03-26 | 1975-10-24 | Zoecon Corp | 3,7,11-Trimethyl-2,4,11-dodecatrienoic acid and derivs. - with juvenile hormone insecticidal activity |
-
1985
- 1985-10-18 HU HU854023A patent/HU200583B/hu not_active IP Right Cessation
-
1986
- 1986-10-17 FI FI864219A patent/FI864219A/fi not_active IP Right Cessation
- 1986-10-17 GB GB8624988A patent/GB2181732B/en not_active Expired
- 1986-10-17 JP JP61245615A patent/JPS62181233A/ja active Pending
- 1986-10-17 DD DD86295359A patent/DD253994A5/de not_active IP Right Cessation
- 1986-10-17 YU YU01767/86A patent/YU176786A/xx unknown
- 1986-10-17 ES ES8602656A patent/ES2002040A6/es not_active Expired
- 1986-10-17 CS CS867543A patent/CS268682B2/cs unknown
- 1986-10-17 IT IT22043/86A patent/IT1197887B/it active
- 1986-10-17 FR FR8614425A patent/FR2588862A1/fr active Pending
- 1986-10-17 NL NL8602620A patent/NL8602620A/nl not_active Application Discontinuation
- 1986-10-20 DE DE3635613A patent/DE3635613A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CS268682B2 (en) | 1990-04-11 |
| ES2002040A6 (es) | 1988-07-01 |
| HU200583B (en) | 1990-07-28 |
| YU176786A (en) | 1988-06-30 |
| FI864219A (fi) | 1987-04-19 |
| DD253994A5 (de) | 1988-02-10 |
| IT8622043A0 (it) | 1986-10-17 |
| IT1197887B (it) | 1988-12-21 |
| GB2181732B (en) | 1989-09-27 |
| JPS62181233A (ja) | 1987-08-08 |
| CS754386A2 (en) | 1989-07-12 |
| FR2588862A1 (fr) | 1987-04-24 |
| HUT41725A (en) | 1987-05-28 |
| FI864219A0 (fi) | 1986-10-17 |
| GB8624988D0 (en) | 1986-11-19 |
| GB2181732A (en) | 1987-04-29 |
| NL8602620A (nl) | 1987-05-18 |
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