DE1229102B - Process for the preparation of monochloro-9-thiabicyclo-2-nonenes and their 9-oxides and 9,9-dioxides - Google Patents
Process for the preparation of monochloro-9-thiabicyclo-2-nonenes and their 9-oxides and 9,9-dioxidesInfo
- Publication number
- DE1229102B DE1229102B DEH51835A DEH0051835A DE1229102B DE 1229102 B DE1229102 B DE 1229102B DE H51835 A DEH51835 A DE H51835A DE H0051835 A DEH0051835 A DE H0051835A DE 1229102 B DE1229102 B DE 1229102B
- Authority
- DE
- Germany
- Prior art keywords
- carbon atom
- thiabicyclo
- monochloro
- nonenes
- oxides
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- RGOSAZGMQBSPCA-UHFFFAOYSA-N 2,3-dichloro-2-cyclononylthionane Chemical compound ClC1C(SCCCCCC1)(C1CCCCCCCC1)Cl RGOSAZGMQBSPCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- -1 FeC Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- AMMGLXRNTZTJRO-UHFFFAOYSA-N 6-chloro-9-thiabicyclo[3.3.1]non-2-ene Chemical compound S1C2C(Cl)CCC1C=CC2 AMMGLXRNTZTJRO-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 description 1
- QUZIEYDEASXPSN-UHFFFAOYSA-N 2,6-dichloro-9-thiabicyclo[3.3.1]nonane Chemical compound S1C2C(Cl)CCC1C(Cl)CC2 QUZIEYDEASXPSN-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- ZEAOMAZLLAHTAP-UHFFFAOYSA-N 6-chloro-9$l^{6}-thiabicyclo[3.3.1]non-2-ene 9,9-dioxide Chemical compound C1=CCC2C(Cl)CCC1S2(=O)=O ZEAOMAZLLAHTAP-UHFFFAOYSA-N 0.000 description 1
- HABQOJNIEKGJMQ-UHFFFAOYSA-N 8-chloro-9-(cyclononen-1-yl)-2,3,4,5,6,7-hexahydrothionine Chemical compound ClC1=C(SCCCCCC1)C1=CCCCCCCC1 HABQOJNIEKGJMQ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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Description
Verfahren zur Herstellung von Monochlor-9-thiabicyclo-2-nonenen sowie deren 9-Oxyden und 9,9-Dioxyden Die Erfindung betrifft ein Verfahren zur Her. stellung von Monochlor-9-thiabicyclo-2-nonenen so. wie deren 9-Oxyden und 9,9-Dioxyden der allgemeinen Formel in der das Chlor an das Kohlenstoffatom 5 gebunden ist, wenn sich die Schwefelbrücke von dem Kohlenstoffatom 1 zu dem Kohlenstoffatom 6 erstreckt, dagegen an das Kohlenstoffatom 6 gebunden ist, wenn sich die Schwefelbrücke von dem Kohlenstoffatom 1 zu dem Kohlenstoffatom 5 erstreckt, und t = 0, 1 oder 2 bedeutet.Process for the production of monochloro-9-thiabicyclo-2-nonenes and their 9-oxides and 9,9-dioxydes. The invention relates to a process for the production of monochloro-9-thiabicyclo-2-nonenes. such as their 9-oxides and 9,9-dioxides of the general formula in which the chlorine is bonded to carbon atom 5 when the sulfur bridge extends from carbon atom 1 to carbon atom 6, whereas it is bonded to carbon atom 6 when the sulfur bridge extends from carbon atom 1 to carbon atom 5, and t = Means 0, 1 or 2.
Erfindungsgemäß wird dabei so vorgegangen, daß man Dichlor-9-thiabicyclononan so lange auf eine Temperatur von etwa 110 bis etwa 220"C erhitzt, bis 1 Moläquivalent Halogenwasserstoff freigesetzt ist, und gegebenenfalls das erhaltene Monochlor-9-thiabicyclononen in an sich bekannter Weise zum 9-Oxyd oder 9,9-Dioxyd oxydiert. According to the invention, the procedure is that dichloro-9-thiabicyclononane is used heated to a temperature of about 110 to about 220 "C until 1 molar equivalent Is released hydrogen halide, and optionally the resulting monochloro-9-thiabicyclononen oxidized in a manner known per se to 9-oxide or 9,9-dioxide.
Chlor-9-thiabicyclo-2-nonen verhält sich chemisch in vielen seiner
Reaktionen so, als ob es ein Gleichgewichtsgemisch von [3,3,1]- und [4,2,1]-Strukturen,
wahrscheinlich auch im Gleichgewicht mit einer ionischen Form
Die Reaktion dauert etwa 1 Stunde bei den höheren Temperaturen und bis zu mehreren Tagen bei den niedrigeren Temperaturen, bis Chlorwasserstoffent wicklung auftritt. Es ist nicht erforderlich, genau 1 Moläquivalent Chlorwasserstoff abzutrennen, doch ist dies nahezu das Optimum. Wenn mehr oder weniger Chlorwasserstoff abgetrennt wird, so kann das Endprodukt leicht durch fraktionierte Destilla tion von Nebenprodukten und/oder nicht umgesetztem Ausgangsmaterial isoliert werden. Harzartige Neben produkte können auf ein Minimum herabgesetzt werden, indem die Reaktion bis zu etwas weniger als der 1000/oigen Umwandlung durchgeführt wird. The reaction takes about 1 hour at the higher temperatures and up to several days at the lower temperatures until hydrogen chloride is found winding occurs. It is not necessary to use exactly 1 molar equivalent of hydrogen chloride to be separated, but this is almost the optimum. If more or less hydrogen chloride is separated, so the end product can easily tion by fractional distillation isolated from by-products and / or unreacted starting material. Resin-like by-products can be minimized by the Reaction to a little less than 1000% conversion is carried out.
Die Reaktion erfordert zwar kein Lösungsmittel, doch kann gegebenenfalls ein inertes Lösungsmittel verwendet werden, um die Wärmeüberführung oder Temperaturkontrolle zu erleichtetn oder die Austreibung des freigesetzten Chlorwasserstoffs zu unterstützen. Zu geeigneten Lösungsmitteln gehören aromatische oder aliphatische Kohlenwasserstoffe, wie beispielsweise Xylol, Cumol, Octan, Decahydronaphthalin oder Tetrahydronaphthalin; chlorierte Kohlenwasserstoffe, wie beispielsweise Tetrachloräthan, Dichlorbenzol, Trichlorbenzol; Anisol; Nitrobenzol; Diphenyläther und andere gegenüber Chlorwasserstoff beständige Lösungsmittel. Although the reaction does not require a solvent, it can optionally an inert solvent can be used for heat transfer or temperature control to facilitate or to support the expulsion of the released hydrogen chloride. Suitable solvents include aromatic or aliphatic hydrocarbons, such as xylene, cumene, octane, decahydronaphthalene or tetrahydronaphthalene; chlorinated hydrocarbons, such as tetrachloroethane, dichlorobenzene, Trichlorobenzene; Anisole; Nitrobenzene; Diphenyl ether and others against hydrogen chloride resistant solvents.
Bei dem erfindungsgemäßen Verfahren ist kein Katalysator erforderlich. Die Reaktion kann jedoch durch Lewis-Säuren (wie beispielsweise FeC, ZnCl2, SbCls, NiCl2, CoCl2 und andere bekannte Schwermetallsalze mit den Eigenschaften von Lewis-Säuren) und oberflächenaktive Festsubstanzen mit Eigenschaften von Lewis-Säuren, wie beispielsweise Aluminiumoxyd, Ton und Aktivkohle, beschleunigt werden. Zur Vermeidung einer Verharzung des Produktes ist es gut, nur kleinere Mengen derartiger Katalysatoren zu verwenden, wobei der übliche Mengenanteil etwa 1 Teil je Million bis zu etwa 50/0 beträgt. No catalyst is required in the process of the invention. However, the reaction can be triggered by Lewis acids (such as FeC, ZnCl2, SbCls, NiCl2, CoCl2 and other known heavy metal salts with the properties of Lewis acids) and surface-active solid substances with properties of Lewis acids, such as aluminum oxide, clay and activated carbon, can be accelerated. To avoid If the product becomes resinous, it is good to use only small amounts of such catalysts to use, the usual proportion of about 1 part per million up to about 50/0 is.
Soll das 9-Oxyd oder 9,9-Dioxyd hergestellt werden, so wird das entsprechende Sulfid durch Behandlung mit 1 bzw. 2 Aquivalenten eines dafür geeigneten Oxydationsmittels oxydiert. Dafür geeignet sind Wasserstoffperoxyd, Peressigsäure, Perbenzoesäure, Perphthalsäure oder andere organische Peroxysäuren, Salpetersäure, Stickstoffdioxyd oder -tetroxyd, Permanganate, Chromsäure oder Dichromate, Bromsäuren oder Bromate, unterchlorige Säure. (oder Chlor + Wasser) oder Ozon. Molektilarer Sauerstoff kann ebenfalls verwendet werden, vorzugsweise unter Verwendung eines Katalysators, wie beispielsweise Vanadiumoxyd oder Stickstoffoxyd. If the 9-Oxide or 9,9-Dioxide is to be produced, then the corresponding is Sulphide by treatment with 1 or 2 equivalents of a suitable oxidizing agent oxidized. Suitable for this are hydrogen peroxide, peracetic acid, perbenzoic acid, Perphthalic acid or other organic peroxy acids, nitric acid, nitrogen dioxide or tetroxide, permanganate, chromic acid or dichromate, bromic acid or bromate, hypochlorous acid. (or chlorine + water) or ozone. Molectilar oxygen can can also be used, preferably using a catalyst such as for example vanadium oxide or nitrogen oxide.
Die erfindungsgemäß erhältlichen neuen Verbindungen sind als Zwischenprodukte, als Schädlingsbekämpfungsmittel, als Zusätze für Hochdruckschmieröle und Schneidöle und als Monomere und Comonomere für Harzsynthesen brauchbar. The novel compounds obtainable according to the invention are available as intermediates, as pesticides, as additives for high pressure lubricating oils and cutting oils and useful as monomers and comonomers for resin synthesis.
Im allgemeinen zeigen die erfindungsgemäß erhältlichen Verbindungen Wirksamkeit auf Mikroorganismen, d. h. Fungi, Bakterien, und in einigen Fällen Nematoden. In general, the compounds obtainable according to the invention show Effectiveness on microorganisms, d. H. Fungi, bacteria, and in some cases nematodes.
Die Verfahrensprodukte können auch mit anderen Wirkstoffen, beispielsweise anderen Fungiciden, z. B. The process products can also with other active ingredients, for example other fungicides, e.g. B.
Schwefel, Dithiocarbamaten, Dodecylguanidin, Nitropolychlorbenzolen und verschiedenen chlorierten Alkylthiogruppen enthaltenden Verbindungen, wie beispielsweise N - Trichlormethylmercapto - 4 - cyclohexen-1,2-dicarboximid, gemeinsam angewandt werden, auch mit Insekticiden, wie beispielsweise chlorierten Kohlenwasserstoff-Insekticiden, Phosphat-Insekticiden und Carbamat-Insekticiden, sowie mit Herbiciden, wie beispielsweise Natriumchlorid, Natriumborat, 2,4-Dichlorphenoxyessigsäure, herbiciden Triazinen, herbiciden Harnstoffen und herbiciden Urazilen.Sulfur, dithiocarbamates, dodecylguanidine, nitropolychlorobenzenes and various chlorinated alkylthio group-containing compounds such as N - trichloromethyl mercapto - 4 - cyclohexene-1,2-dicarboximide, used together also with insecticides, such as chlorinated hydrocarbon insecticides, Phosphate insecticides and carbamate insecticides, as well as with herbicides such as Sodium chloride, sodium borate, 2,4-dichlorophenoxyacetic acid, herbicidal triazines, herbicidal ureas and herbicidal uracilene.
Schließlich können die Verfahrensprodukte mit synergistischen Mitteln, die zur Erhöhung der Aktivität als Schädlingsbekämpfungsmittel dienen, beispielsweise Piperonylbutylat, gemeinsam eingesetzt werden. Finally, the process products can be used with synergistic agents, which serve as pesticides to increase the activity, for example Piperonyl butylate, can be used together.
Die folgenden Beispiele erläutern die Erfindung. The following examples illustrate the invention.
Beispiel 1 6-Chlor-9-thiabicyclo-[3,3,1]-2-nonen 211 g 2,6 - Dichlor - 9 - thiabicyclo - [3,3,1] - nonan (1 Mol), erhalten gemäß Beispiel 1 der Patentanmeldung H 51 834 IV/12 q, wurden 20 Stunden auf 166 bis 184"C erhitzt, bis 36,5 Volumteile (1 Mol) Chlorwasserstoff (gemessen durch Auffangen in Wasser und Titration) abgegeben waren. Der Rückstand wurde im Vakuum destilliert, wobei man 148 g (850/0) farbloses Destillat vom Kp.o.i = 64 bis 69"C erhielt. N2D5= 1,5713. Example 1 6-chloro-9-thiabicyclo- [3,3,1] -2-nonene 211 g 2,6-dichloro - 9 - thiabicyclo - [3,3,1] - nonane (1 mol), obtained according to Example 1 of the patent application H 51 834 IV / 12 q, were heated to 166 to 184 "C for 20 hours, up to 36.5 parts by volume (1 mol) of hydrogen chloride (measured by collecting in water and titration) given off was. The residue was distilled in vacuo, giving 148 g (850/0) of colorless Distillate obtained from b.p.o.i = 64 to 69 "C. N2D5 = 1.5713.
Analyse: C8H11SCl. Analysis: C8H11SCl.
Berechnet ... Cl 20,3, S 18,35°/o; gefunden ... Cl 19,9, S 18,290/0. Calculated ... Cl 20.3, S 18.35%; found ... Cl 19.9, S 18.290 / 0.
Beispiel 2 6-Chlor-9-thiabicyclo- [3,3,1 ]-2-nonen-9-oxyd 17,5 Teile 6-Chlor-9- thiabicyclo- [3,3,1]-2-nonen wurden in 10() Volumteilen Eisessig gelöst. Zu dieser Lösung wurden allmählich 11,4Volumteile 300/obiges Wasserstoffperoxyd zugegeben. Man ließ die exotherme Reaktion bis -auf 76"C kommen. Nach dem Nachlassen der Wärmefreisetzung wurde das Reaktionsgemisch auf einem Wasserbad 15 Minuten auf 95"C erwärmt. Das Reaktionsgemisch wurde dann mit 1000 Teilen Wasser verdünnt und das organische Produkt mit Chloroform extrahiert. Der Extrakt wurde im Vakuum eingedampft, wobei man einen viskosen öligen Rückstand erhielt, der sich bei längerem Stehen verfestigte. Example 2 6-chloro-9-thiabicyclo- [3,3,1] -2-nonene-9-oxide 17.5 parts 6-chloro-9-thiabicyclo- [3,3,1] -2-nonene were dissolved in 10 () parts by volume of glacial acetic acid. 11.4 parts by volume of 300 / above hydrogen peroxide were gradually added to this solution admitted. The exothermic reaction was allowed to come to -76 "C. After subsiding To release heat, the reaction mixture was left on a water bath for 15 minutes 95 "C. The reaction mixture was then diluted with 1000 parts of water and the organic product extracted with chloroform. The extract was evaporated in vacuo, a viscous oily residue was obtained, which upon prolonged standing was obtained solidified.
Analyse: CsH11SOC1 Berechnet . . Cl l8,701o; gefunden . . Cl 16,7010.Analysis: CsH11SOC1 calculated. . Cl 18,701o; found . . Cl 16.7010.
Dieses Produkt ergab bei Anwendung auf zweigefleckte Milben bei 0,1 0/oiger Konzentration in wäßriger Dispersion in 24 Stunden eine praktisch vollständige Abtötung. This product when applied to two-spotted mites gave 0.1 0 / o concentration in aqueous dispersion practically complete in 24 hours Mortification.
Die Infrarotprüfung zeigte eine kleine Verunreinigung durch einen Acetatester, der für den etwas niedrigen Chlorgehalt verantwortlich ist. The infrared test showed a small amount of contamination from one Acetate ester, which is responsible for the somewhat low chlorine content.
Beispiel 3 6-Chlor-9-thiabicyclo- [3,3,1 ]-2-nonen-9,9-dioxyd Zu einer Lösung von 52,5 g (0,3 Mol) 6-Chlor-9-thiabicyclo-[3,3,1]-2-nonen in 300 ml Eisessig wurden 85,2 g (0,75 Mol) 300/obiges Wasserstoffperoxyd innerhalb von 20 Minuten unter Rühren zugesetzt, wobei die Temperatur bis zum Siedepunkt steigen gelassen wurde. Dann wurde das Gemisch 20 Minuten auf dem Dampfbad erhitzt, zu 3 1 Wasser gegeben und mit 400 ml Chloroform extrahiert. Die Extrakte wurden über Magnesiumsulfat getrocknet, filtriert, zur Entfernung des Chloroforms eingedampft und der Rückstand aus Essigsäure umkristallisiert, wobei 38 g farblose Kristalle vom F. 114 bis 115"C erhalten wurden. Umkristallisation aus Essigsäure lieferte 34 g (550/o) Ausbeute vom F. 119 bis 1200C, aus Methanol vom F. 120,5 bis 121,5"C. Das Infrarotspektrum (Nujol) zeigte eine C = C-Bande bei 1646 cm-1 und - SO2 --Banden bei 1119 und 1297 cm-l. Example 3 6-chloro-9-thiabicyclo- [3,3,1] -2-nonene-9,9-dioxide To a solution of 52.5 g (0.3 mol) of 6-chloro-9-thiabicyclo- [3,3,1] -2-nonene in 300 ml Glacial acetic acid was 85.2 g (0.75 mol) of 300 / above hydrogen peroxide within 20 Added minutes with stirring, the temperature rising to the boiling point was left. Then the mixture was heated on the steam bath for 20 minutes, to 3 1 added water and extracted with 400 ml of chloroform. The extracts were over Dried magnesium sulfate, filtered, evaporated to remove the chloroform and the residue was recrystallized from acetic acid, giving 38 g of colorless crystals with a melting point of 114 to 115 ° C. Recrystallization from acetic acid provided 34 g (550 / o) yield from 119 ° to 1200 ° C. from methanol from 120.5 ° to 121.5 ° C. The infrared spectrum (Nujol) showed a C = C band at 1646 cm-1 and - SO2 - bands at 1119 and 1297 cm-l.
Analyse: CsHllSO2Cl Berechnet C 46,48, H 5,36, Cl 17,16, S 15,510/0; gefunden C 46,52, H 5,33, Cl 17,20, S 15,470/0. Analysis: CsHIISO2Cl Calculated C 46.48, H 5.36, Cl 17.16, S 15.510 / 0; Found C 46.52, H 5.33, Cl 17.20, S 15.470 / 0.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26124963A | 1963-02-25 | 1963-02-25 | |
| US26090963A | 1963-02-25 | 1963-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1229102B true DE1229102B (en) | 1966-11-24 |
Family
ID=26948260
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641543648 Pending DE1543648B1 (en) | 1963-02-25 | 1964-02-25 | Process for the preparation of chlorination products of dichloro-9-thiabicyclononanes |
| DEH51834A Pending DE1232976B (en) | 1963-02-25 | 1964-02-25 | Process for the preparation of beta, beta'-dichloro-9-thiabicyclononanes or their 9-oxides or 9, 9-dioxides |
| DEH58112A Pending DE1297111B (en) | 1963-02-25 | 1964-02-25 | Thiabicyclo-2-nonene compounds |
| DEH58369A Pending DE1295567B (en) | 1963-02-25 | 1964-02-25 | Process for the preparation of 9-thiabicyclononane derivatives |
| DEH51835A Pending DE1229102B (en) | 1963-02-25 | 1964-11-25 | Process for the preparation of monochloro-9-thiabicyclo-2-nonenes and their 9-oxides and 9,9-dioxides |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641543648 Pending DE1543648B1 (en) | 1963-02-25 | 1964-02-25 | Process for the preparation of chlorination products of dichloro-9-thiabicyclononanes |
| DEH51834A Pending DE1232976B (en) | 1963-02-25 | 1964-02-25 | Process for the preparation of beta, beta'-dichloro-9-thiabicyclononanes or their 9-oxides or 9, 9-dioxides |
| DEH58112A Pending DE1297111B (en) | 1963-02-25 | 1964-02-25 | Thiabicyclo-2-nonene compounds |
| DEH58369A Pending DE1295567B (en) | 1963-02-25 | 1964-02-25 | Process for the preparation of 9-thiabicyclononane derivatives |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE673676A (en) |
| DE (5) | DE1543648B1 (en) |
| FR (1) | FR1412397A (en) |
| GB (2) | GB1061472A (en) |
| IT (1) | IT1193788B (en) |
| NL (3) | NL6401629A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4458061A (en) * | 1982-09-29 | 1984-07-03 | The Dow Chemical Company | 9-Thiabicyclononanediisocyanates and polymers made therefrom |
| US4581435A (en) * | 1982-12-29 | 1986-04-08 | The Dow Chemical Company | Alkyl-substituted thiapolycyclic polyahl and polyurethanes, polyamides and polyureas based thereon |
| JPS61500965A (en) * | 1984-06-29 | 1986-05-15 | ザ・ダウ・ケミカル・カンパニ− | Alkyl-substituted thia polycyclic polyal and polymers produced therefrom |
| AU571553B2 (en) * | 1984-06-29 | 1988-04-21 | Dow Chemical Company, The | 9-thiabicyclononanediisocyanates and polymers prepared therefrom |
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
| DE69728531T2 (en) * | 1996-05-13 | 2004-09-30 | Syngenta Ltd., Guildford | BICYCLIC AMINES AS INSECTICIDES |
| GB9623944D0 (en) * | 1996-11-15 | 1997-01-08 | Zeneca Ltd | Bicyclic amine derivatives |
| GB9624114D0 (en) * | 1996-11-20 | 1997-01-08 | Zeneca Ltd | Pesticidal bicyclic amine derivatives |
| GB9624611D0 (en) * | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
| ES2216131T3 (en) * | 1996-11-26 | 2004-10-16 | Syngenta Limited | DERIVATIVES OF 8-AZABICICLO 3,2,1) OCTANO-, 8- AZABICICLO 3,2.1) OCT-6- ENO- 9-AZABICICLO 3.3.1) NONANO-, 9-AZA -3- OXABICICLO 3.3.1) NONANO - AND 9 -AZA-3- THIABICICLE 3.3.1) NONANO, ITS PREPARATION AND ITS USE AS INSECTICIDES. |
-
0
- NL NL129205D patent/NL129205C/xx active
-
1964
- 1964-02-06 GB GB5166/64A patent/GB1061472A/en not_active Expired
- 1964-02-07 GB GB5314/64A patent/GB1061473A/en not_active Expired
- 1964-02-21 NL NL6401629A patent/NL6401629A/xx unknown
- 1964-02-21 NL NL6401628A patent/NL6401628A/xx unknown
- 1964-02-24 FR FR964895A patent/FR1412397A/en not_active Expired
- 1964-02-25 IT IT04157/64A patent/IT1193788B/en active
- 1964-02-25 DE DE19641543648 patent/DE1543648B1/en active Pending
- 1964-02-25 DE DEH51834A patent/DE1232976B/en active Pending
- 1964-02-25 DE DEH58112A patent/DE1297111B/en active Pending
- 1964-02-25 DE DEH58369A patent/DE1295567B/en active Pending
- 1964-11-25 DE DEH51835A patent/DE1229102B/en active Pending
-
1965
- 1965-12-13 BE BE673676A patent/BE673676A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1295567B (en) | 1969-05-22 |
| NL6401628A (en) | 1964-08-26 |
| DE1232976B (en) | 1967-01-26 |
| NL6401629A (en) | 1964-10-26 |
| GB1061473A (en) | 1967-03-15 |
| GB1061472A (en) | 1967-03-15 |
| DE1543648B1 (en) | 1970-04-02 |
| FR1412397A (en) | 1965-10-01 |
| BE673676A (en) | 1966-04-01 |
| IT1193788B (en) | 1988-08-24 |
| DE1297111B (en) | 1969-06-12 |
| NL129205C (en) |
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