GB583874A - Production of organic fluorine compounds - Google Patents
Production of organic fluorine compoundsInfo
- Publication number
- GB583874A GB583874A GB7549/44A GB754944A GB583874A GB 583874 A GB583874 A GB 583874A GB 7549/44 A GB7549/44 A GB 7549/44A GB 754944 A GB754944 A GB 754944A GB 583874 A GB583874 A GB 583874A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- tetrafluoroethylene
- compounds
- products
- fluorine
- 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.)
- Expired
Links
- 150000004812 organic fluorine compounds Chemical class 0.000 title 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 abstract 25
- 150000001875 compounds Chemical class 0.000 abstract 13
- 239000000047 product Substances 0.000 abstract 12
- 239000003054 catalyst Substances 0.000 abstract 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 9
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract 8
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 8
- 229910052731 fluorine Inorganic materials 0.000 abstract 8
- 239000011737 fluorine Substances 0.000 abstract 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 7
- -1 trifluorochloroethylene, difluorodichloroethylene, trifluorobromoethylene Chemical group 0.000 abstract 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 abstract 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 6
- 150000002894 organic compounds Chemical class 0.000 abstract 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 6
- 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 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 229910052708 sodium Inorganic materials 0.000 abstract 5
- 239000011734 sodium Substances 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 239000012263 liquid product Substances 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- 239000000376 reactant Substances 0.000 abstract 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 239000001282 iso-butane Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- 239000012265 solid product Substances 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 150000001241 acetals Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 229920002678 cellulose Chemical group 0.000 abstract 2
- 235000010980 cellulose Nutrition 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 abstract 2
- 125000001033 ether group Chemical group 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 2
- 239000011118 polyvinyl acetate Substances 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- QZFIQARJCSJGEG-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2-(1,2,2,2-tetrafluoroethoxy)ethane Chemical compound FC(F)(F)C(F)OC(F)C(F)(F)F QZFIQARJCSJGEG-UHFFFAOYSA-N 0.000 abstract 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 abstract 1
- OMMADTGFNSRNEJ-UHFFFAOYSA-N 2,2,3-trichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)(Cl)CCl OMMADTGFNSRNEJ-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- IWOIFKQCZJIYMQ-UHFFFAOYSA-N 2,4-dimethoxybutyl acetate Chemical compound C(C)(=O)OCC(OC)CCOC IWOIFKQCZJIYMQ-UHFFFAOYSA-N 0.000 abstract 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 abstract 1
- FVTWJXMFYOXOKK-UHFFFAOYSA-N 2-fluoroacetamide Chemical compound NC(=O)CF FVTWJXMFYOXOKK-UHFFFAOYSA-N 0.000 abstract 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 229920002367 Polyisobutene Polymers 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract 1
- 229920002472 Starch Chemical group 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- WQULVXNWEYLDJY-UHFFFAOYSA-N bis(2-chloroethyl) carbonate Chemical compound ClCCOC(=O)OCCCl WQULVXNWEYLDJY-UHFFFAOYSA-N 0.000 abstract 1
- 229910021538 borax Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000000295 complement effect Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 abstract 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 abstract 1
- 229910000397 disodium phosphate Inorganic materials 0.000 abstract 1
- 235000019800 disodium phosphate Nutrition 0.000 abstract 1
- 239000005038 ethylene vinyl acetate Substances 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 150000004676 glycans Polymers 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 abstract 1
- 229960003868 paraldehyde Drugs 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 239000005017 polysaccharide Substances 0.000 abstract 1
- 150000004804 polysaccharides Polymers 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 239000004328 sodium tetraborate Substances 0.000 abstract 1
- 235000010339 sodium tetraborate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 abstract 1
- KBMBVTRWEAAZEY-UHFFFAOYSA-N trisulfane Chemical group SSS KBMBVTRWEAAZEY-UHFFFAOYSA-N 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
-
- 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
- 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
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- 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
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US583874XA | 1943-04-23 | 1943-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB583874A true GB583874A (en) | 1947-01-01 |
Family
ID=22016493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7549/44A Expired GB583874A (en) | 1943-04-23 | 1944-04-24 | Production of organic fluorine compounds |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE463259A (enrdf_load_stackoverflow) |
| GB (1) | GB583874A (enrdf_load_stackoverflow) |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2646449A (en) * | 1950-06-29 | 1953-07-21 | Du Pont | Fluorocarbon compounds and preparation of same |
| US2657761A (en) * | 1950-06-12 | 1953-11-03 | Phillips Petroleum Co | Method of separating ethane from hydrocarbon mixtures |
| US2861989A (en) * | 1955-01-29 | 1958-11-25 | Hoechst Ag | New photo-sensitizing dyestuffs containing a tetrahydroquinazoline group |
| US2870222A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Polymers of 2-difluorovinyl methyl ether |
| US2870219A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Difluorovinyl methyl ether |
| DE1057270B (de) * | 1957-01-10 | 1959-05-14 | Bayer Ag | Brandfeste Schmiermittel, Steuerfluessigkeiten und Hydraulikoele |
| US2907795A (en) * | 1956-08-02 | 1959-10-06 | Du Pont | Co-telomers and process for making them |
| DE1069318B (de) * | 1955-06-08 | 1959-11-19 | Minnesota Mining And Manufacturing Company, St. Paul, Minn. (V. St. A.) | Schmiermittel-Mischungen |
| US2925424A (en) * | 1956-05-03 | 1960-02-16 | Du Pont | Fluoroketals and their preparation |
| US2992276A (en) * | 1959-05-20 | 1961-07-11 | Du Pont | Process for preparing polyfluoro alkyl compounds |
| US3004961A (en) * | 1957-09-24 | 1961-10-17 | Pennsalt Chemicals Corp | Polymeric material and method of making same |
| DE1115873B (de) * | 1957-03-20 | 1961-10-26 | Minnesota Mining & Mfg | Daempfungs- und Kreiselfluessigkeit |
| US3012021A (en) * | 1956-05-16 | 1961-12-05 | Pennsalt Chemicals Corp | Polymerization of vinylidene fluoride |
| US3029252A (en) * | 1958-04-23 | 1962-04-10 | Du Pont | Omega-hydropolyfluoroperhalo-alkanones and ketals thereof |
| US3032543A (en) * | 1959-02-04 | 1962-05-01 | Du Pont | Polymerization of tetrafluoroethylene |
| US3067262A (en) * | 1961-05-10 | 1962-12-04 | Du Pont | Telomers of tetrafluoroethylene |
| US3272871A (en) * | 1962-02-01 | 1966-09-13 | Du Pont | Fluorocarbon-hydrocarbon polyethers |
| US3336189A (en) * | 1966-02-02 | 1967-08-15 | Baxter Laboratories Inc | Composition and method of inducing 3, 3, 3-trichloro-1, 1, 2, 2-tetrafluoropropane anesthesia |
| US3342875A (en) * | 1962-03-26 | 1967-09-19 | Du Pont | Hydrogen capped fluorocarbon polyethers |
| US4079084A (en) * | 1972-03-15 | 1978-03-14 | Imperial Chemical Industries Limited | Fluorocarbon surfactants |
| CN112552148A (zh) * | 2020-12-31 | 2021-03-26 | 浙江诺亚氟化工有限公司 | 全氟己酮生产过程中副产物2-氯-1,1,1,3,3,3-六氟丙烷的资源化利用方法 |
-
0
- BE BE463259D patent/BE463259A/xx unknown
-
1944
- 1944-04-24 GB GB7549/44A patent/GB583874A/en not_active Expired
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2657761A (en) * | 1950-06-12 | 1953-11-03 | Phillips Petroleum Co | Method of separating ethane from hydrocarbon mixtures |
| US2646449A (en) * | 1950-06-29 | 1953-07-21 | Du Pont | Fluorocarbon compounds and preparation of same |
| US2861989A (en) * | 1955-01-29 | 1958-11-25 | Hoechst Ag | New photo-sensitizing dyestuffs containing a tetrahydroquinazoline group |
| DE1069318B (de) * | 1955-06-08 | 1959-11-19 | Minnesota Mining And Manufacturing Company, St. Paul, Minn. (V. St. A.) | Schmiermittel-Mischungen |
| US2925424A (en) * | 1956-05-03 | 1960-02-16 | Du Pont | Fluoroketals and their preparation |
| US3012021A (en) * | 1956-05-16 | 1961-12-05 | Pennsalt Chemicals Corp | Polymerization of vinylidene fluoride |
| US2907795A (en) * | 1956-08-02 | 1959-10-06 | Du Pont | Co-telomers and process for making them |
| DE1057270B (de) * | 1957-01-10 | 1959-05-14 | Bayer Ag | Brandfeste Schmiermittel, Steuerfluessigkeiten und Hydraulikoele |
| DE1115873B (de) * | 1957-03-20 | 1961-10-26 | Minnesota Mining & Mfg | Daempfungs- und Kreiselfluessigkeit |
| US2870222A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Polymers of 2-difluorovinyl methyl ether |
| US2870219A (en) * | 1957-05-20 | 1959-01-20 | Allied Chem | Difluorovinyl methyl ether |
| US3004961A (en) * | 1957-09-24 | 1961-10-17 | Pennsalt Chemicals Corp | Polymeric material and method of making same |
| US3029252A (en) * | 1958-04-23 | 1962-04-10 | Du Pont | Omega-hydropolyfluoroperhalo-alkanones and ketals thereof |
| US3032543A (en) * | 1959-02-04 | 1962-05-01 | Du Pont | Polymerization of tetrafluoroethylene |
| US2992276A (en) * | 1959-05-20 | 1961-07-11 | Du Pont | Process for preparing polyfluoro alkyl compounds |
| US3067262A (en) * | 1961-05-10 | 1962-12-04 | Du Pont | Telomers of tetrafluoroethylene |
| US3272871A (en) * | 1962-02-01 | 1966-09-13 | Du Pont | Fluorocarbon-hydrocarbon polyethers |
| US3342875A (en) * | 1962-03-26 | 1967-09-19 | Du Pont | Hydrogen capped fluorocarbon polyethers |
| US3336189A (en) * | 1966-02-02 | 1967-08-15 | Baxter Laboratories Inc | Composition and method of inducing 3, 3, 3-trichloro-1, 1, 2, 2-tetrafluoropropane anesthesia |
| US4079084A (en) * | 1972-03-15 | 1978-03-14 | Imperial Chemical Industries Limited | Fluorocarbon surfactants |
| CN112552148A (zh) * | 2020-12-31 | 2021-03-26 | 浙江诺亚氟化工有限公司 | 全氟己酮生产过程中副产物2-氯-1,1,1,3,3,3-六氟丙烷的资源化利用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE463259A (enrdf_load_stackoverflow) |
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