DE2238458A1 - Herstellung von fluoralkansulfiden - Google Patents
Herstellung von fluoralkansulfidenInfo
- Publication number
- DE2238458A1 DE2238458A1 DE2238458A DE2238458A DE2238458A1 DE 2238458 A1 DE2238458 A1 DE 2238458A1 DE 2238458 A DE2238458 A DE 2238458A DE 2238458 A DE2238458 A DE 2238458A DE 2238458 A1 DE2238458 A1 DE 2238458A1
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- sulfide
- reaction
- yield
- carried out
- 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
- 238000004519 manufacturing process Methods 0.000 title description 9
- 150000003568 thioethers Chemical class 0.000 title description 8
- 238000000034 method Methods 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 44
- -1 fluoroalkyl sulfides Chemical class 0.000 claims description 29
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 28
- 239000000376 reactant Substances 0.000 claims description 13
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 45
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 239000002253 acid Substances 0.000 description 19
- 238000009835 boiling Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Chemical group 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- XTGYEAXBNRVNQU-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-iodopropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)I XTGYEAXBNRVNQU-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 8
- 239000005297 pyrex Substances 0.000 description 8
- 239000013256 coordination polymer Substances 0.000 description 7
- 150000003457 sulfones Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 description 6
- 239000012286 potassium permanganate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- BBZVTTKMXRPMHZ-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoro-2-iodopropane Chemical compound FC(F)(F)C(F)(I)C(F)(F)F BBZVTTKMXRPMHZ-UHFFFAOYSA-N 0.000 description 5
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000013375 chromatographic separation Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- 150000003460 sulfonic acids Chemical class 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- YBNLWIZAWPBUKQ-UHFFFAOYSA-N trichloro(trichloromethylsulfonyl)methane Chemical class ClC(Cl)(Cl)S(=O)(=O)C(Cl)(Cl)Cl YBNLWIZAWPBUKQ-UHFFFAOYSA-N 0.000 description 3
- VRSDIWXVAUOVEA-UHFFFAOYSA-N trifluoro(methylsulfanyl)methane Chemical compound CSC(F)(F)F VRSDIWXVAUOVEA-UHFFFAOYSA-N 0.000 description 3
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 3
- BULLJMKUVKYZDJ-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-iodohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I BULLJMKUVKYZDJ-UHFFFAOYSA-N 0.000 description 2
- GHWVALHXBJGRMU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1,4-bis(methylsulfanyl)butane Chemical compound CSC(F)(F)C(F)(F)C(F)(F)C(F)(F)SC GHWVALHXBJGRMU-UHFFFAOYSA-N 0.000 description 2
- FZVCWPXQEFOEJF-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1-iodo-4-methylsulfanylbutane Chemical compound FC(C(C(F)(F)SC)(F)F)(C(I)(F)F)F FZVCWPXQEFOEJF-UHFFFAOYSA-N 0.000 description 2
- XNIBSTIKPHNKSO-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoro-2-iodoethane Chemical compound FC(F)(Cl)C(F)(F)I XNIBSTIKPHNKSO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- BLVKDXZGNZXMBZ-UHFFFAOYSA-M potassium;1,1,2,2,3,3,3-heptafluoropropane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F BLVKDXZGNZXMBZ-UHFFFAOYSA-M 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- UVBDRNICDIYMAS-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)octane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UVBDRNICDIYMAS-UHFFFAOYSA-N 0.000 description 1
- ZUMUOTAASDQYEZ-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-methylsulfanylpropane Chemical compound CSC(F)(F)C(F)(F)C(F)(F)F ZUMUOTAASDQYEZ-UHFFFAOYSA-N 0.000 description 1
- IEZBSKSOLBFSGG-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-methylsulfanylethane Chemical compound CSC(F)(F)C(F)(F)F IEZBSKSOLBFSGG-UHFFFAOYSA-N 0.000 description 1
- OXZBIZPWVZBBOH-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoro-2-methylsulfanylpropane Chemical compound CSC(F)(C(F)(F)F)C(F)(F)F OXZBIZPWVZBBOH-UHFFFAOYSA-N 0.000 description 1
- YYBMGVRXEFBHTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonyl fluoride Chemical compound FC(F)(F)C(F)(C(F)(F)F)S(F)(=O)=O YYBMGVRXEFBHTL-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- YGLIPWPVVGJDDA-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1,2-bis(methylsulfanyl)ethane Chemical compound CSC(F)(F)C(F)(F)SC YGLIPWPVVGJDDA-UHFFFAOYSA-N 0.000 description 1
- NZXVPCQHQVWOFD-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1,2-diiodoethane Chemical compound FC(F)(I)C(F)(F)I NZXVPCQHQVWOFD-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 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
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Chemical group 0.000 description 1
- 239000005935 Sulfuryl fluoride Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- WFRUBUQWJYMMRQ-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WFRUBUQWJYMMRQ-UHFFFAOYSA-M 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940038570 terrell Drugs 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3711871A GB1401431A (en) | 1971-08-06 | 1971-08-06 | Preparation of fluoroalkane sulphides and the conversion thereof into fluoroalkane sulphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2238458A1 true DE2238458A1 (de) | 1973-02-15 |
Family
ID=10393879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2238458A Pending DE2238458A1 (de) | 1971-08-06 | 1972-08-04 | Herstellung von fluoralkansulfiden |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3816277A (enExample) |
| JP (1) | JPS4828409A (enExample) |
| DE (1) | DE2238458A1 (enExample) |
| FR (1) | FR2149893A5 (enExample) |
| GB (1) | GB1401431A (enExample) |
| IT (1) | IT963759B (enExample) |
| NL (1) | NL7210763A (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935277A (en) * | 1974-02-04 | 1976-01-27 | Ciba-Geigy Corporation | New Rf -glycols containing two perfluoroalkylthio groups and useful compositions therefrom |
| CA2554293A1 (en) | 2004-01-30 | 2005-08-18 | Great Lakes Chemical Corporation | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| KR20060132889A (ko) * | 2004-01-30 | 2006-12-22 | 그레이트 레이크스 케미칼 코퍼레이션 | 제조 방법 및 시스템, 조성물, 계면활성제, 모노머 유닛,금속 착체, 포스페이트 에스테르, 글리콜, 수성 막 형성발포제, 및 발포 안정제 |
| JP2007526360A (ja) * | 2004-01-30 | 2007-09-13 | グレート・レークス・ケミカル・コーポレーション | 製造方法並びにシステム、組成物、界面活性剤、モノマー単位、金属錯体、燐酸エステル、グリコール、水性皮膜形成フォーム、及びフォーム安定剤 |
| WO2005074639A2 (en) * | 2004-01-30 | 2005-08-18 | Great Lakes Chemical Corporation | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| KR20080030572A (ko) * | 2005-07-28 | 2008-04-04 | 그레이트 레이크스 케미칼 코퍼레이션 | 제조 방법 및 시스템, 조성물, 계면활성제, 모노머 유닛,금속 착물, 포스페이트 에스터, 글리콜, 수성 필름 형성발포체, 및 발포 안정제 |
| US20070027349A1 (en) * | 2005-07-28 | 2007-02-01 | Stephan Brandstadter | Halogenated Compositions |
| EP2081881A2 (en) * | 2006-08-03 | 2009-07-29 | E. I. du Pont de Nemours and Company | Telomer compositions and production processes |
| US8318656B2 (en) | 2007-07-03 | 2012-11-27 | E. I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| EP3966286A1 (en) | 2019-05-10 | 2022-03-16 | 3M Innovative Properties Company | Hydrofluorothioethers and methods of using same |
| WO2021079223A1 (en) * | 2019-10-21 | 2021-04-29 | 3M Innovative Properties Company | Removal of electroluminescenct materials from substrates |
| US11920102B2 (en) * | 2020-01-29 | 2024-03-05 | 3M Innovative Properties Company | Deposition compositions and methods of making and using same |
| CN119798124B (zh) * | 2024-12-02 | 2026-04-14 | 西安近代化学研究所 | 一种双三氟甲基硫醚的制备方法 |
-
1971
- 1971-08-06 GB GB3711871A patent/GB1401431A/en not_active Expired
-
1972
- 1972-07-18 US US00272829A patent/US3816277A/en not_active Expired - Lifetime
- 1972-08-04 NL NL7210763A patent/NL7210763A/xx unknown
- 1972-08-04 IT IT27908/72A patent/IT963759B/it active
- 1972-08-04 FR FR7228165A patent/FR2149893A5/fr not_active Expired
- 1972-08-04 DE DE2238458A patent/DE2238458A1/de active Pending
- 1972-08-07 JP JP47079050A patent/JPS4828409A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2149893A5 (enExample) | 1973-03-30 |
| JPS4828409A (enExample) | 1973-04-14 |
| NL7210763A (enExample) | 1973-02-08 |
| US3816277A (en) | 1974-06-11 |
| IT963759B (it) | 1974-01-21 |
| GB1401431A (en) | 1975-07-16 |
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