CS209901B2 - Method of production of quadruple cyclic ketons - Google Patents
Method of production of quadruple cyclic ketons Download PDFInfo
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- CS209901B2 CS209901B2 CS782257A CS225778A CS209901B2 CS 209901 B2 CS209901 B2 CS 209901B2 CS 782257 A CS782257 A CS 782257A CS 225778 A CS225778 A CS 225778A CS 209901 B2 CS209901 B2 CS 209901B2
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- CS
- Czechoslovakia
- Prior art keywords
- acid
- formula
- halide
- mol
- iii
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 125000004122 cyclic group Chemical group 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 39
- -1 alkenyl radical Chemical class 0.000 claims abstract description 37
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 27
- 150000001336 alkenes Chemical class 0.000 claims abstract description 24
- 239000002841 Lewis acid Substances 0.000 claims abstract description 18
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 18
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 claims abstract description 18
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011592 zinc chloride Substances 0.000 claims abstract description 14
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- 150000003857 carboxamides Chemical class 0.000 claims description 12
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003997 cyclic ketones Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 239000011260 aqueous acid Substances 0.000 claims 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000002917 insecticide Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000011541 reaction mixture Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 238000010992 reflux Methods 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 238000006352 cycloaddition reaction Methods 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- PDKAXHLOFWCWIH-UHFFFAOYSA-N 1,1-dichlorobuta-1,3-diene Chemical compound ClC(Cl)=CC=C PDKAXHLOFWCWIH-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000002561 ketenes Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZFBGKBGUMMBBMY-UHFFFAOYSA-N 1,1,2-trichlorobuta-1,3-diene Chemical compound ClC(Cl)=C(Cl)C=C ZFBGKBGUMMBBMY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GBSXCHLYXIBMCZ-UHFFFAOYSA-N 2-ethyl-n,n-dimethylbutanamide Chemical compound CCC(CC)C(=O)N(C)C GBSXCHLYXIBMCZ-UHFFFAOYSA-N 0.000 description 2
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JBCOYDRQCPJFHJ-UHFFFAOYSA-N cyclohexanecarboxylic acid dimethylamide Natural products CN(C)C(=O)C1CCCCC1 JBCOYDRQCPJFHJ-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 1
- CRNSOGJNJXTEQG-ARJAWSKDSA-N (1z)-1,2-dichlorobuta-1,3-diene Chemical compound Cl\C=C(/Cl)C=C CRNSOGJNJXTEQG-ARJAWSKDSA-N 0.000 description 1
- PQQAVRNNAPPTJZ-NSCUHMNNSA-N (3e)-1,1-dibromopenta-1,3-diene Chemical compound C\C=C\C=C(Br)Br PQQAVRNNAPPTJZ-NSCUHMNNSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- VSEFNECOXSMFGP-UHFFFAOYSA-N 1,1,2-trichloro-3-methylpenta-1,3-diene Chemical compound CC=C(C)C(Cl)=C(Cl)Cl VSEFNECOXSMFGP-UHFFFAOYSA-N 0.000 description 1
- IHGFJCDCRGMWPU-UHFFFAOYSA-N 1,1,2-trichlorohepta-1,3-diene Chemical compound CCCC=CC(Cl)=C(Cl)Cl IHGFJCDCRGMWPU-UHFFFAOYSA-N 0.000 description 1
- XYEIXXAZOHMEPP-UHFFFAOYSA-N 1,1,2-trichloropenta-1,3-diene Chemical compound CC=CC(Cl)=C(Cl)Cl XYEIXXAZOHMEPP-UHFFFAOYSA-N 0.000 description 1
- LEAVKXWGBWVZTN-UHFFFAOYSA-N 1,1,2-trifluoro-3-methylbuta-1,3-diene Chemical compound CC(=C)C(F)=C(F)F LEAVKXWGBWVZTN-UHFFFAOYSA-N 0.000 description 1
- FWTUDISDSYABRU-UHFFFAOYSA-N 1,1,2-trifluorobuta-1,3-diene Chemical compound FC(F)=C(F)C=C FWTUDISDSYABRU-UHFFFAOYSA-N 0.000 description 1
- HVKWWGONWHKKJH-UHFFFAOYSA-N 1,1-dibromo-2-chlorobuta-1,3-diene Chemical compound C=CC(Cl)=C(Br)Br HVKWWGONWHKKJH-UHFFFAOYSA-N 0.000 description 1
- VFQACGLDVJLGAQ-UHFFFAOYSA-N 1,1-dibromo-2-fluorobuta-1,3-diene Chemical compound C=CC(F)=C(Br)Br VFQACGLDVJLGAQ-UHFFFAOYSA-N 0.000 description 1
- GRZADSLMRHHZDB-UHFFFAOYSA-N 1,1-dibromo-2-fluoropenta-1,3-diene Chemical compound CC=CC(F)=C(Br)Br GRZADSLMRHHZDB-UHFFFAOYSA-N 0.000 description 1
- RNBKPCKISNMDNC-UHFFFAOYSA-N 1,1-dichloro-2-fluorobuta-1,3-diene Chemical compound C=CC(F)=C(Cl)Cl RNBKPCKISNMDNC-UHFFFAOYSA-N 0.000 description 1
- LRFNZMGZAXBYDJ-UHFFFAOYSA-N 1,1-dichloro-2-fluoropenta-1,3-diene Chemical compound CC=CC(F)=C(Cl)Cl LRFNZMGZAXBYDJ-UHFFFAOYSA-N 0.000 description 1
- GUWMWOIPQGUEBX-UHFFFAOYSA-N 1,1-dichloro-2-methylbuta-1,3-diene Chemical compound C=CC(C)=C(Cl)Cl GUWMWOIPQGUEBX-UHFFFAOYSA-N 0.000 description 1
- QETIAVHXKWYRDJ-UHFFFAOYSA-N 1,1-dichloro-3-methylbuta-1,3-diene Chemical compound CC(=C)C=C(Cl)Cl QETIAVHXKWYRDJ-UHFFFAOYSA-N 0.000 description 1
- ZCYYSKXOJVSHHI-UHFFFAOYSA-N 1,1-dichlorohepta-1,3-diene Chemical compound CCCC=CC=C(Cl)Cl ZCYYSKXOJVSHHI-UHFFFAOYSA-N 0.000 description 1
- AMLGIWNESUNRFV-UHFFFAOYSA-N 1,1-dichlorohexa-1,3-diene Chemical compound CCC=CC=C(Cl)Cl AMLGIWNESUNRFV-UHFFFAOYSA-N 0.000 description 1
- XWOKUHDOBJAMAL-UHFFFAOYSA-N 1,1-difluorobuta-1,3-diene Chemical compound FC(F)=CC=C XWOKUHDOBJAMAL-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DBEWPASGNDEPPK-UHFFFAOYSA-N 1,2-dibromobuta-1,3-diene Chemical compound BrC=C(Br)C=C DBEWPASGNDEPPK-UHFFFAOYSA-N 0.000 description 1
- AIUXFDGAMNRPSC-UHFFFAOYSA-N 1,3-dibromo-2-methylpenta-1,3-diene Chemical compound CC=C(Br)C(C)=CBr AIUXFDGAMNRPSC-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- SHFPIKZCGRKOKS-UHFFFAOYSA-N 1-chloro-2-ethenylcyclohexene Chemical compound ClC1=C(C=C)CCCC1 SHFPIKZCGRKOKS-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- GVIVQCNNFDHBAG-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxole Chemical compound CC1(C)OC=CO1 GVIVQCNNFDHBAG-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- DOPFCVBSOPCWAQ-UHFFFAOYSA-N 2,2-dimethylcyclobutan-1-one Chemical compound CC1(C)CCC1=O DOPFCVBSOPCWAQ-UHFFFAOYSA-N 0.000 description 1
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 description 1
- LKVWJQBODUNMAV-UHFFFAOYSA-N 2-bromo-1,1-dichlorobuta-1,3-diene Chemical compound ClC(Cl)=C(Br)C=C LKVWJQBODUNMAV-UHFFFAOYSA-N 0.000 description 1
- HUIZFMJDJQHJOX-UHFFFAOYSA-N 2-but-3-en-2-ylidenepropanedinitrile Chemical compound C=CC(C)=C(C#N)C#N HUIZFMJDJQHJOX-UHFFFAOYSA-N 0.000 description 1
- PKVRTDNAPQGMGP-UHFFFAOYSA-N 2-chloro-3-methylbuta-1,3-diene Chemical compound CC(=C)C(Cl)=C PKVRTDNAPQGMGP-UHFFFAOYSA-N 0.000 description 1
- FQRMJJJRCOMBKG-UHFFFAOYSA-N 2-cyclobutylacetic acid Chemical compound OC(=O)CC1CCC1 FQRMJJJRCOMBKG-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- GZVUWANWWQXKQR-UHFFFAOYSA-N 2-methylpropanamide;hydrochloride Chemical compound Cl.CC(C)C(N)=O GZVUWANWWQXKQR-UHFFFAOYSA-N 0.000 description 1
- PTNFILLRHCVPKZ-UHFFFAOYSA-N 2-methylsulfonylbuta-1,3-diene Chemical compound CS(=O)(=O)C(=C)C=C PTNFILLRHCVPKZ-UHFFFAOYSA-N 0.000 description 1
- WFYXNYMBYDZLLP-UHFFFAOYSA-N 2-prop-2-enylidenepropanedinitrile Chemical compound C=CC=C(C#N)C#N WFYXNYMBYDZLLP-UHFFFAOYSA-N 0.000 description 1
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 1
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
- CTKQONQLKZBJQK-UHFFFAOYSA-N 3-(dichloromethylidene)pent-1-ene Chemical compound CCC(C=C)=C(Cl)Cl CTKQONQLKZBJQK-UHFFFAOYSA-N 0.000 description 1
- ZFDCBQQVYKAWHX-UHFFFAOYSA-N 3-ethenyl-2,2,3-trimethylcyclopentan-1-one Chemical compound CC1(C)C(=O)CCC1(C)C=C ZFDCBQQVYKAWHX-UHFFFAOYSA-N 0.000 description 1
- WWAKYXYJMRXUKE-UHFFFAOYSA-N 5,5,5-trifluoro-4-(trifluoromethyl)penta-1,3-diene Chemical compound FC(F)(F)C(C(F)(F)F)=CC=C WWAKYXYJMRXUKE-UHFFFAOYSA-N 0.000 description 1
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 241000250966 Tanacetum cinerariifolium Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- 238000006074 cyclodimerization reaction Methods 0.000 description 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OZZYKXXGCOLLLO-TWTPFVCWSA-N ethyl (2e,4e)-hexa-2,4-dienoate Chemical compound CCOC(=O)\C=C\C=C\C OZZYKXXGCOLLLO-TWTPFVCWSA-N 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- XSGHLZBESSREDT-UHFFFAOYSA-N methylenecyclopropane Chemical compound C=C1CC1 XSGHLZBESSREDT-UHFFFAOYSA-N 0.000 description 1
- QIRVGKYPAOQVNP-UHFFFAOYSA-N methylidenecyclobutane Chemical compound C=C1CCC1 QIRVGKYPAOQVNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- LEBSGWZESXZDHD-UHFFFAOYSA-N n-methylmethanamine;2-methylpropanoic acid Chemical compound CNC.CC(C)C(O)=O LEBSGWZESXZDHD-UHFFFAOYSA-N 0.000 description 1
- ABRWESLGGMHKEA-UHFFFAOYSA-N n-tert-butylaniline Chemical compound CC(C)(C)NC1=CC=CC=C1 ABRWESLGGMHKEA-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940102001 zinc bromide Drugs 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
- C07C45/51—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
- C07C45/516—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 involving transformation of nitrogen-containing compounds to >C = O groups
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 |
|---|---|---|---|
| DE19772715336 DE2715336A1 (de) | 1977-04-06 | 1977-04-06 | Verfahren zur herstellung viergliedriger cyclischer ketone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209901B2 true CS209901B2 (en) | 1981-12-31 |
Family
ID=6005749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS782257A CS209901B2 (en) | 1977-04-06 | 1978-04-06 | Method of production of quadruple cyclic ketons |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4216172A (de) |
| JP (1) | JPS53124239A (de) |
| AT (1) | AT356644B (de) |
| BE (1) | BE865758A (de) |
| BR (1) | BR7802114A (de) |
| CA (1) | CA1110649A (de) |
| CH (1) | CH638481A5 (de) |
| CS (1) | CS209901B2 (de) |
| DD (1) | DD137098A5 (de) |
| DE (1) | DE2715336A1 (de) |
| DK (1) | DK151078A (de) |
| ES (1) | ES468565A1 (de) |
| FR (1) | FR2386510A1 (de) |
| GB (1) | GB1587390A (de) |
| HU (1) | HU175441B (de) |
| IL (1) | IL54430A (de) |
| IT (1) | IT7821982A0 (de) |
| NL (1) | NL7803627A (de) |
| ZA (1) | ZA781952B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675342A (en) * | 1979-02-02 | 1987-06-23 | The United States Of America As Represented By The Secretary Of Agriculture | Cockroach repellents |
| DE3013565A1 (de) * | 1980-04-09 | 1981-10-15 | Consortium für elektrochemische Industrie GmbH, 8000 München | Neue (beta) - a -ungesaettigte ketone und isoprenoide 2,6-dienone, verfahren zu deren herstellung und ihre verwendung als geruchs- und geschmacksstoffe |
| US4505905A (en) * | 1982-04-15 | 1985-03-19 | E. I. Du Pont De Nemours And Company | Cyclobutanone antibacterials |
| DE3220730A1 (de) * | 1982-06-02 | 1983-12-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,2-dimethyl-3-aryl-cyclopropan-carbonsaeuren (carbonsaeureestern), neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
| US4524219A (en) * | 1984-02-03 | 1985-06-18 | Xerox Corporation | Process for squaraine compositions from half esters of squaric acid |
| US4585895A (en) * | 1985-02-20 | 1986-04-29 | Xerox Corporation | Processes for the preparation of mixed squaraine compositions |
| US4746756A (en) * | 1985-06-24 | 1988-05-24 | Xerox Corporation | Photoconductive imaging members with novel fluorinated squaraine compounds |
| US5420356A (en) * | 1993-08-11 | 1995-05-30 | Sumitomo Chemical Company, Limited | Process for producing cyclobutanones |
| US20030105279A1 (en) * | 2001-08-30 | 2003-06-05 | Pharmacia Corporation | Aromatic and heteroaromatic acid halides for synthesizing polyamides |
| US6677487B2 (en) | 2001-08-30 | 2004-01-13 | Pharmacia Corporation | α-haloenamine reagents |
| IN2014DN10229A (de) * | 2012-05-25 | 2015-08-07 | Nutech Ventures |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078306A (en) * | 1958-04-24 | 1963-02-19 | Basf Ag | Process for the production of alphachloroximes and their hydrochlorides |
| US3129248A (en) * | 1960-07-18 | 1964-04-14 | Du Pont | Preparation of fluorocyclobutanones |
| US3408398A (en) * | 1964-03-17 | 1968-10-29 | Eastman Kodak Co | 2-cyclobuten-1-one compounds and process for their preparation |
| CA1051454A (en) * | 1975-05-21 | 1979-03-27 | Marinus J. Van Den Brink | Process for the preparation of cyclobutanones |
| DE2654061A1 (de) * | 1976-08-26 | 1978-03-23 | Bayer Ag | Verfahren zur herstellung von cyclobutanonen |
-
1977
- 1977-04-06 DE DE19772715336 patent/DE2715336A1/de not_active Withdrawn
-
1978
- 1978-03-13 US US05/886,229 patent/US4216172A/en not_active Expired - Lifetime
- 1978-04-03 GB GB12931/78A patent/GB1587390A/en not_active Expired
- 1978-04-03 CH CH357178A patent/CH638481A5/de not_active IP Right Cessation
- 1978-04-03 IL IL54430A patent/IL54430A/xx unknown
- 1978-04-04 DD DD78204581A patent/DD137098A5/de unknown
- 1978-04-04 CA CA300,360A patent/CA1110649A/en not_active Expired
- 1978-04-04 AT AT236478A patent/AT356644B/de not_active IP Right Cessation
- 1978-04-04 IT IT7821982A patent/IT7821982A0/it unknown
- 1978-04-04 JP JP3886678A patent/JPS53124239A/ja active Pending
- 1978-04-05 ES ES468565A patent/ES468565A1/es not_active Expired
- 1978-04-05 ZA ZA00781952A patent/ZA781952B/xx unknown
- 1978-04-05 FR FR7810057A patent/FR2386510A1/fr active Granted
- 1978-04-05 DK DK151078A patent/DK151078A/da not_active Application Discontinuation
- 1978-04-05 BR BR7802114A patent/BR7802114A/pt unknown
- 1978-04-05 NL NL7803627A patent/NL7803627A/xx not_active Application Discontinuation
- 1978-04-06 BE BE186620A patent/BE865758A/xx not_active IP Right Cessation
- 1978-04-06 HU HU78BA3645A patent/HU175441B/hu unknown
- 1978-04-06 CS CS782257A patent/CS209901B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7803627A (nl) | 1978-10-10 |
| IL54430A0 (en) | 1978-07-31 |
| BR7802114A (pt) | 1979-04-03 |
| BE865758A (fr) | 1978-10-06 |
| IT7821982A0 (it) | 1978-04-04 |
| CA1110649A (en) | 1981-10-13 |
| US4216172A (en) | 1980-08-05 |
| ATA236478A (de) | 1979-10-15 |
| AT356644B (de) | 1980-05-12 |
| CH638481A5 (de) | 1983-09-30 |
| ZA781952B (en) | 1979-03-28 |
| GB1587390A (en) | 1981-04-01 |
| JPS53124239A (en) | 1978-10-30 |
| ES468565A1 (es) | 1978-12-01 |
| DE2715336A1 (de) | 1978-10-19 |
| DD137098A5 (de) | 1979-08-15 |
| DK151078A (da) | 1978-10-07 |
| FR2386510B1 (de) | 1983-10-28 |
| FR2386510A1 (fr) | 1978-11-03 |
| HU175441B (hu) | 1980-08-28 |
| IL54430A (en) | 1981-11-30 |
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