DE2820410A1 - Verfahren zur herstellung von dihalogencyclopropan-derivaten - Google Patents
Verfahren zur herstellung von dihalogencyclopropan-derivatenInfo
- Publication number
- DE2820410A1 DE2820410A1 DE19782820410 DE2820410A DE2820410A1 DE 2820410 A1 DE2820410 A1 DE 2820410A1 DE 19782820410 DE19782820410 DE 19782820410 DE 2820410 A DE2820410 A DE 2820410A DE 2820410 A1 DE2820410 A1 DE 2820410A1
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- onium
- unsaturated compound
- compound
- hydroxide
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 9
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- -1 compound Ester Chemical class 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 11
- 150000004010 onium ions Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical group BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 150000001925 cycloalkenes Chemical class 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229950005228 bromoform Drugs 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004026 tertiary sulfonium compounds Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000000126 substance Substances 0.000 description 23
- 239000008346 aqueous phase Substances 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- QEVYQHFZTXUKJU-UHFFFAOYSA-M methyl-tri(octan-2-yl)azanium;chloride Chemical compound [Cl-].CCCCCCC(C)[N+](C)(C(C)CCCCCC)C(C)CCCCCC QEVYQHFZTXUKJU-UHFFFAOYSA-M 0.000 description 10
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- KNXISWJTUXKGCI-UHFFFAOYSA-N tert-butyl 3-methylbut-2-enoate Chemical compound CC(C)=CC(=O)OC(C)(C)C KNXISWJTUXKGCI-UHFFFAOYSA-N 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XRLIZCVYAYNXIF-IAFSNKLZSA-N (1E,3Z,5E)-cyclododeca-1,3,5-triene Chemical compound C1CCC\C=C\C=C/C=C/CC1 XRLIZCVYAYNXIF-IAFSNKLZSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- BTTDZADGGXIQJC-UHFFFAOYSA-M S(=O)(=O)(OCC)[O-].C(C)[S+](C(CCCCCCCCCC)C)C(CCCCCCCCCC)C Chemical compound S(=O)(=O)(OCC)[O-].C(C)[S+](C(CCCCCCCCCC)C)C(CCCCCCCCCC)C BTTDZADGGXIQJC-UHFFFAOYSA-M 0.000 description 2
- SFWCTNOMXZGGPM-UHFFFAOYSA-M S(=O)(=O)(OCC)[O-].C(C)[S+](CCCCCCCCCCC)CCCCCCCCCCCCCCCC Chemical compound S(=O)(=O)(OCC)[O-].C(C)[S+](CCCCCCCCCCC)CCCCCCCCCCCCCCCC SFWCTNOMXZGGPM-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YSNAFJBMOMSMDU-UHFFFAOYSA-M [OH-].[Na+].C(Br)(Br)Br Chemical compound [OH-].[Na+].C(Br)(Br)Br YSNAFJBMOMSMDU-UHFFFAOYSA-M 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001942 cyclopropanes Chemical class 0.000 description 2
- CTRVMZJBEVWFHM-OWOJBTEDSA-N cyclotetradecene Chemical compound C1CCCCCC\C=C\CCCCC1 CTRVMZJBEVWFHM-OWOJBTEDSA-N 0.000 description 2
- KEFTYRIPQSPONC-UHFFFAOYSA-N diethyl(hydroxymethyl)azanium iodide Chemical compound [I-].C(C)[NH+](CO)CC KEFTYRIPQSPONC-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 description 1
- 229930006713 (+)-car-3-ene Natural products 0.000 description 1
- FHBJNBBNAAXQKT-XCADPSHZSA-N (1Z,3Z,5Z)-cyclonona-1,3,5-triene Chemical compound C1C\C=C/C=C\C=C/C1 FHBJNBBNAAXQKT-XCADPSHZSA-N 0.000 description 1
- WFLPGXDWMZEHGP-CLFYSBASSA-N (1z)-1-methylcyclooctene Chemical compound C\C1=C\CCCCCC1 WFLPGXDWMZEHGP-CLFYSBASSA-N 0.000 description 1
- WLWFQGXZIDYWQF-UHFFFAOYSA-N (2,2-dichlorocyclopropyl)benzene Chemical compound ClC1(Cl)CC1C1=CC=CC=C1 WLWFQGXZIDYWQF-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- RITONZMLZWYPHW-UHFFFAOYSA-N 3-methylhex-1-ene Chemical compound CCCC(C)C=C RITONZMLZWYPHW-UHFFFAOYSA-N 0.000 description 1
- XQUAFNTWCYIHKC-UHFFFAOYSA-N Br[IH]C(I)(I)Br Chemical compound Br[IH]C(I)(I)Br XQUAFNTWCYIHKC-UHFFFAOYSA-N 0.000 description 1
- LWPZJRVHNOWJPA-UHFFFAOYSA-N Br[IH]C(I)(I)Cl Chemical compound Br[IH]C(I)(I)Cl LWPZJRVHNOWJPA-UHFFFAOYSA-N 0.000 description 1
- ZJPRLMAXLPJNAI-UHFFFAOYSA-N Br[IH]C(I)(I)F Chemical compound Br[IH]C(I)(I)F ZJPRLMAXLPJNAI-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LSDWVVLCKONBMU-UHFFFAOYSA-N ClC(Cl)(Br)[ClH]Br Chemical compound ClC(Cl)(Br)[ClH]Br LSDWVVLCKONBMU-UHFFFAOYSA-N 0.000 description 1
- WJIJEZMNUSOOPQ-UHFFFAOYSA-N Cl[IH]C(I)(I)Cl Chemical compound Cl[IH]C(I)(I)Cl WJIJEZMNUSOOPQ-UHFFFAOYSA-N 0.000 description 1
- BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 1
- OXYGVBGMQWOGIA-UHFFFAOYSA-N FC(I)(I)[IH]Cl Chemical compound FC(I)(I)[IH]Cl OXYGVBGMQWOGIA-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- YBOZNTGUYASNRA-UHFFFAOYSA-N beta-Methyl-beta-octylen Natural products CCCCCC=C(C)C YBOZNTGUYASNRA-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- BXXZYCGUNVYWSA-UHFFFAOYSA-N butyl 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylate Chemical group C(CCC)OC(=O)C1C(C1(C)C)(Cl)Cl BXXZYCGUNVYWSA-UHFFFAOYSA-N 0.000 description 1
- IJZWZSGPEJOCHI-UHFFFAOYSA-N butyl 3-methylbut-2-enoate Chemical group CCCCOC(=O)C=C(C)C IJZWZSGPEJOCHI-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- UCIYGNATMHQYCT-OWOJBTEDSA-N cyclodecene Chemical compound C1CCCC\C=C\CCC1 UCIYGNATMHQYCT-OWOJBTEDSA-N 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- GMUVJAZTJOCSND-OWOJBTEDSA-N cycloundecene Chemical compound C1CCCC\C=C\CCCC1 GMUVJAZTJOCSND-OWOJBTEDSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- RJTBSDBMSCZHNS-UHFFFAOYSA-M di(decan-2-yl)-methylsulfanium;chloride Chemical compound [Cl-].CCCCCCCCC(C)[S+](C)C(C)CCCCCCCC RJTBSDBMSCZHNS-UHFFFAOYSA-M 0.000 description 1
- PWLCLNYZHRGZJS-UHFFFAOYSA-M dodecan-2-yl-ethyl-hexadecan-2-ylsulfanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCCC(C)[S+](CC)C(C)CCCCCCCCCC PWLCLNYZHRGZJS-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- OGFUUSCSLHJVFP-UHFFFAOYSA-M hexadecan-2-yl(dimethyl)sulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCCCC(C)[S+](C)C OGFUUSCSLHJVFP-UHFFFAOYSA-M 0.000 description 1
- PKSRDJZZJZNWQB-UHFFFAOYSA-M hexadecyl(dimethyl)sulfanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCC[S+](C)C PKSRDJZZJZNWQB-UHFFFAOYSA-M 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- MPSSKVPWSSCCFY-UHFFFAOYSA-M hydroxy(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)O MPSSKVPWSSCCFY-UHFFFAOYSA-M 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- QTYFQZHJYYULRV-UHFFFAOYSA-N n-methyloctan-2-amine;hydrochloride Chemical compound Cl.CCCCCCC(C)NC QTYFQZHJYYULRV-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- AXTDZHQPXGKMIB-UHFFFAOYSA-N octan-2-amine;hydrochloride Chemical compound [Cl-].CCCCCCC(C)[NH3+] AXTDZHQPXGKMIB-UHFFFAOYSA-N 0.000 description 1
- NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- VDJIUIIELCBIBH-UHFFFAOYSA-M potassium;chloroform;hydroxide Chemical compound [OH-].[K+].ClC(Cl)Cl VDJIUIIELCBIBH-UHFFFAOYSA-M 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Inorganic materials [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PRAJLVIUHUDWDZ-UHFFFAOYSA-M sodium;chloroform;hydroxide Chemical compound [OH-].[Na+].ClC(Cl)Cl PRAJLVIUHUDWDZ-UHFFFAOYSA-M 0.000 description 1
- XEACEWUMVUWRDS-UHFFFAOYSA-N sulfanium ethyl sulfate Chemical compound S(=O)(=O)(OCC)[O-].[SH3+] XEACEWUMVUWRDS-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SNIFAVVHRQZYGO-UHFFFAOYSA-N tetradec-5-ene Chemical compound CCCCCCCCC=CCCCC SNIFAVVHRQZYGO-UHFFFAOYSA-N 0.000 description 1
- WRSDPVGFRCMMHT-UHFFFAOYSA-N trideca-4,8-diene Chemical compound CCCCC=CCCC=CCCC WRSDPVGFRCMMHT-UHFFFAOYSA-N 0.000 description 1
- YFNPDWVAVPFSGM-UHFFFAOYSA-M triethyl(hydroxy)azanium;hydroxide Chemical compound [OH-].CC[N+](O)(CC)CC YFNPDWVAVPFSGM-UHFFFAOYSA-M 0.000 description 1
- LKDQWVKWYGOVJW-UHFFFAOYSA-M triethylsulfanium;iodide Chemical compound [I-].CC[S+](CC)CC LKDQWVKWYGOVJW-UHFFFAOYSA-M 0.000 description 1
- GOTIICCWNAPLMN-UHFFFAOYSA-M trimethylsulfanium;bromide Chemical compound [Br-].C[S+](C)C GOTIICCWNAPLMN-UHFFFAOYSA-M 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| GB19989/77A GB1600414A (en) | 1977-05-12 | 1977-05-12 | Preparation of dihalocyclopropane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2820410A1 true DE2820410A1 (de) | 1978-11-16 |
| DE2820410C2 DE2820410C2 (enrdf_load_stackoverflow) | 1987-12-03 |
Family
ID=10138484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782820410 Granted DE2820410A1 (de) | 1977-05-12 | 1978-05-10 | Verfahren zur herstellung von dihalogencyclopropan-derivaten |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS53141246A (enrdf_load_stackoverflow) |
| AU (1) | AU527083B2 (enrdf_load_stackoverflow) |
| CH (1) | CH640207A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2820410A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2390411A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1600414A (enrdf_load_stackoverflow) |
| NL (1) | NL7804900A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004039917A1 (ja) * | 2002-10-29 | 2004-05-13 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | プラスチック用難燃剤 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432540A (en) * | 1972-05-16 | 1976-04-22 | Shell Int Research | Process for the preparation of cyclopropane derivatives |
| US4008287A (en) * | 1972-05-16 | 1977-02-15 | Shell Oil Company | Process for the preparation of cyclopropane derivatives |
| US4012430A (en) * | 1972-05-16 | 1977-03-15 | Shell Oil Company | Process for the preparation of cyclopropane derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265743A (en) * | 1962-05-14 | 1966-08-09 | Ethyl Corp | Production of dihalocarbene adducts |
| US3375286A (en) * | 1965-10-04 | 1968-03-26 | Texaco Inc | Preparation of 1, 1-dichlorocyclopropane compounds |
| GB1323183A (en) * | 1971-01-14 | 1973-07-11 | Bdh Pharmaceuticals Ltd | Cyclopropane esters and acids thereof |
-
1977
- 1977-05-12 GB GB19989/77A patent/GB1600414A/en not_active Expired
-
1978
- 1978-05-08 NL NL7804900A patent/NL7804900A/xx not_active Application Discontinuation
- 1978-05-10 FR FR7813904A patent/FR2390411A1/fr active Granted
- 1978-05-10 JP JP5455978A patent/JPS53141246A/ja active Granted
- 1978-05-10 DE DE19782820410 patent/DE2820410A1/de active Granted
- 1978-05-10 CH CH507378A patent/CH640207A5/de not_active IP Right Cessation
- 1978-05-10 AU AU35988/78A patent/AU527083B2/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432540A (en) * | 1972-05-16 | 1976-04-22 | Shell Int Research | Process for the preparation of cyclopropane derivatives |
| US4008287A (en) * | 1972-05-16 | 1977-02-15 | Shell Oil Company | Process for the preparation of cyclopropane derivatives |
| US4012430A (en) * | 1972-05-16 | 1977-03-15 | Shell Oil Company | Process for the preparation of cyclopropane derivatives |
Non-Patent Citations (1)
| Title |
|---|
| Angew. Chem. 86, 187-196 (1974) * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004039917A1 (ja) * | 2002-10-29 | 2004-05-13 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | プラスチック用難燃剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3598878A (en) | 1979-12-06 |
| GB1600414A (en) | 1981-10-14 |
| FR2390411B1 (enrdf_load_stackoverflow) | 1981-01-02 |
| NL7804900A (nl) | 1978-11-14 |
| FR2390411A1 (fr) | 1978-12-08 |
| AU527083B2 (en) | 1983-02-17 |
| CH640207A5 (en) | 1983-12-30 |
| JPS53141246A (en) | 1978-12-08 |
| DE2820410C2 (enrdf_load_stackoverflow) | 1987-12-03 |
| JPS6160053B2 (enrdf_load_stackoverflow) | 1986-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |