CH502973A - Verfahren zur Verknüpfung von Adamantan-Ringen durch C3- oder C4-Polymethylenketten - Google Patents
Verfahren zur Verknüpfung von Adamantan-Ringen durch C3- oder C4-PolymethylenkettenInfo
- Publication number
- CH502973A CH502973A CH915668A CH915668A CH502973A CH 502973 A CH502973 A CH 502973A CH 915668 A CH915668 A CH 915668A CH 915668 A CH915668 A CH 915668A CH 502973 A CH502973 A CH 502973A
- Authority
- CH
- Switzerland
- Prior art keywords
- adamantane
- alkyl
- bis
- hydrocarbon
- chloride
- Prior art date
Links
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title claims abstract description 113
- -1 polyethylene Polymers 0.000 title claims abstract description 61
- 239000004698 Polyethylene Substances 0.000 title abstract 2
- 230000008878 coupling Effects 0.000 title abstract 2
- 238000010168 coupling process Methods 0.000 title abstract 2
- 238000005859 coupling reaction Methods 0.000 title abstract 2
- 229920000573 polyethylene Polymers 0.000 title abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 78
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 29
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 19
- 150000001348 alkyl chlorides Chemical class 0.000 claims abstract description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000000047 product Substances 0.000 claims description 81
- 238000006243 chemical reaction Methods 0.000 claims description 72
- 150000001350 alkyl halides Chemical class 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000001273 butane Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000005376 secondary alkyl halides Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- HUCLCMAVGXHPPK-UHFFFAOYSA-N 1-ethyl-3-methyladamantane Chemical compound C1C(C2)CC3CC2(C)CC1(CC)C3 HUCLCMAVGXHPPK-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 10
- 229920006037 cross link polymer Polymers 0.000 abstract description 5
- 239000000178 monomer Substances 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 30
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000013849 propane Nutrition 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RPPKCFHVBDXPRZ-UHFFFAOYSA-N 1,2,2-trimethyladamantane Chemical class C1C(C2)CC3CC1C(C)(C)C2(C)C3 RPPKCFHVBDXPRZ-UHFFFAOYSA-N 0.000 description 2
- RTPQXHZLCUUIJP-UHFFFAOYSA-N 1,2-dimethyladamantane Chemical class C1C(C2)CC3CC1C(C)C2(C)C3 RTPQXHZLCUUIJP-UHFFFAOYSA-N 0.000 description 2
- UJSORZVCMMYGBS-UHFFFAOYSA-N 1,3,5,7-tetramethyladamantane Chemical class C1C(C2)(C)CC3(C)CC1(C)CC2(C)C3 UJSORZVCMMYGBS-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 2
- LXTHCCWEYOKFSR-UHFFFAOYSA-N 1-ethyladamantane Chemical compound C1C(C2)CC3CC2CC1(CC)C3 LXTHCCWEYOKFSR-UHFFFAOYSA-N 0.000 description 2
- DHWIUNJDGPKQKI-UHFFFAOYSA-N 1-hexyladamantane Chemical compound C1C(C2)CC3CC2CC1(CCCCCC)C3 DHWIUNJDGPKQKI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001805 chlorine compounds Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000005375 primary alkyl halides Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- HBIKNLNXSSBQCT-UHFFFAOYSA-N 1,2,5,7-tetramethyladamantane Chemical compound C1C(C2)(C)CC3(C)CC1C(C)C2(C)C3 HBIKNLNXSSBQCT-UHFFFAOYSA-N 0.000 description 1
- DZLCQHWJVJXVES-UHFFFAOYSA-N 1,3-dichloroadamantane Chemical compound C1C(C2)CC3CC1(Cl)CC2(Cl)C3 DZLCQHWJVJXVES-UHFFFAOYSA-N 0.000 description 1
- VQHPRVYDKRESCL-UHFFFAOYSA-N 1-bromoadamantane Chemical compound C1C(C2)CC3CC2CC1(Br)C3 VQHPRVYDKRESCL-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- AZCUIXHZJHFUFI-UHFFFAOYSA-N 1-butyladamantane Chemical compound C1C(C2)CC3CC2CC1(CCCC)C3 AZCUIXHZJHFUFI-UHFFFAOYSA-N 0.000 description 1
- LOVSGPXFIZDSNE-UHFFFAOYSA-N 1-decyladamantane Chemical class C1C(C2)CC3CC2CC1(CCCCCCCCCC)C3 LOVSGPXFIZDSNE-UHFFFAOYSA-N 0.000 description 1
- DMBMVJPNXOZMRN-UHFFFAOYSA-N 1-ethyl-2,2-dimethyladamantane Chemical class C1C(C2)CC3CC2C(C)(C)C1(CC)C3 DMBMVJPNXOZMRN-UHFFFAOYSA-N 0.000 description 1
- OSCLUJGAKICIRW-UHFFFAOYSA-N 1-ethyl-2-methyladamantane Chemical compound C1C(C2)CC3CC2C(C)C1(CC)C3 OSCLUJGAKICIRW-UHFFFAOYSA-N 0.000 description 1
- PMOPIGGDESIABT-UHFFFAOYSA-N 1-ethyl-4-methyladamantane Chemical compound C1C(C2)CC3CC1(CC)CC2C3C PMOPIGGDESIABT-UHFFFAOYSA-N 0.000 description 1
- UZUCFTVAWGRMTQ-UHFFFAOYSA-N 1-methyladamantane Chemical class C1C(C2)CC3CC2CC1(C)C3 UZUCFTVAWGRMTQ-UHFFFAOYSA-N 0.000 description 1
- RCXJARRRXOPXBC-UHFFFAOYSA-N 2-bromoadamantane Chemical compound C1C(C2)CC3CC1C(Br)C2C3 RCXJARRRXOPXBC-UHFFFAOYSA-N 0.000 description 1
- FKNCPNVBSHZODI-UHFFFAOYSA-N 2-ethyl-1,2-dimethyladamantane Chemical class C1C(C2)CC3CC1C(CC)(C)C2(C)C3 FKNCPNVBSHZODI-UHFFFAOYSA-N 0.000 description 1
- VMODAALDMAYACB-UHFFFAOYSA-N 2-methyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2C3 VMODAALDMAYACB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 238000006434 Ritter amidation reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical class [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64981067A | 1967-06-29 | 1967-06-29 | |
| US72588868A | 1968-05-01 | 1968-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH502973A true CH502973A (de) | 1971-02-15 |
Family
ID=27095710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH915668A CH502973A (de) | 1967-06-29 | 1968-06-20 | Verfahren zur Verknüpfung von Adamantan-Ringen durch C3- oder C4-Polymethylenketten |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE717261A (pm) |
| CH (1) | CH502973A (pm) |
| DE (1) | DE1768761A1 (pm) |
| FR (1) | FR1570330A (pm) |
| GB (1) | GB1190874A (pm) |
| NL (1) | NL6809226A (pm) |
-
1968
- 1968-06-20 CH CH915668A patent/CH502973A/de not_active IP Right Cessation
- 1968-06-27 DE DE19681768761 patent/DE1768761A1/de active Pending
- 1968-06-27 BE BE717261D patent/BE717261A/xx unknown
- 1968-06-28 NL NL6809226A patent/NL6809226A/xx unknown
- 1968-06-28 FR FR1570330D patent/FR1570330A/fr not_active Expired
- 1968-07-01 GB GB3125768A patent/GB1190874A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6809226A (pm) | 1968-12-30 |
| FR1570330A (pm) | 1969-06-06 |
| DE1768761A1 (de) | 1971-11-18 |
| BE717261A (pm) | 1968-12-27 |
| GB1190874A (en) | 1970-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2457550C3 (de) | Verfahren zur Herstellung von 1,1,3,4,4,6-Hexamethyl-1,2,3,4-tetrahydronaphthalin | |
| DE1543980A1 (de) | Katalysierte Wuertz-Fittig-Synthesen | |
| DE3339218C2 (de) | 4-[2-(4n-Alkylcyclohexyl)ethyl]cyclohexancarbonsäureester und deren Verwendung als elektro-optische Anzeigematerialien | |
| CH634814A5 (de) | Chlorierte 4-methylphthalsaeure oder deren anhydrid und herstellungsverfahren dafuer. | |
| DE69510131T2 (de) | Ein Verfahren zur Herstellung von Diaryliodoniumfluoroalkylsulfonatsalzen | |
| US3560578A (en) | Reaction for linking nuclei of adamantane hydrocarbons | |
| DE2223048A1 (de) | Hydrolytisch und thermisch bestaendige vinylaromatische Sulfonsaeureharze | |
| DE2532722A1 (de) | Verfahren zur reinigung von diphenylmethan-4,4'-diisocyanat | |
| DE69014386T2 (de) | Verfahren zur Herstellung von alkylsubstituierten Tetralinen und Indanen. | |
| CH502973A (de) | Verfahren zur Verknüpfung von Adamantan-Ringen durch C3- oder C4-Polymethylenketten | |
| DE2016128A1 (de) | Verfahren zur Isomerisierung von 5-Vinylbicyclo eckige Klammer auf 2.2.1 eckige Klammer zu hept-2-enen | |
| US3523137A (en) | Preparation of diamidoadamantane compounds from dihaloadamantanes | |
| US3523136A (en) | Preparation of diamidoadamantane compounds | |
| DE1026524B (de) | Verfahren zur Herstellung von Polymerisaten aus Olefinen | |
| US2047656A (en) | Manufacture of 4-acetyl-5-tertiarybutyl-1,3-xylene | |
| AT375067B (de) | Verfahren zur herstellung von reinem 3-amino-crotonitril | |
| DE1543458A1 (de) | Verfahren zur Herstellung von 2,6-Dimethylnaphthalin | |
| US3356718A (en) | Preparation of dicarboxyadamantane compounds from dihaloadamantanes | |
| DE607380C (de) | Verfahren zur Herstellung von Kondensationsprodukten | |
| EP0332124B1 (de) | Verfahren zur Herstellung von halogenhaltigen aromatischen Verbindungen | |
| DE1445384C3 (de) | Verfahren zur Herstellung hochmolekularer, thermoplastischer Mischpolyester | |
| DE2132961A1 (de) | Verfahren zur herstellung von n-alkylcarbazolen | |
| DE69220687T2 (de) | Polymere von 3-Ethyl-1-hexen | |
| DE1745137A1 (de) | Polymere Verbindungen | |
| AT357145B (de) | Verfahren zur herstellung von trans-cyclohexan- 1,4-diisocyanat |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |