CH384566A - Procédé de préparation de la dichlorodiphénylsulfone - Google Patents

Info

Publication number

CH384566A

CH384566A CH7263159A CH7263159A CH384566A CH 384566 A CH384566 A CH 384566A CH 7263159 A CH7263159 A CH 7263159A CH 7263159 A CH7263159 A CH 7263159A CH 384566 A CH384566 A CH 384566A

Authority

CH

Switzerland

Prior art keywords

dichlorodiphenylsulfone

preparing

chlorobenzene

sulfone

sulfur trioxide

Prior art date

1958-07-05

Links

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• 238000004519 manufacturing process Methods 0.000 title claims description 4
• IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 title description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 14
• GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 claims description 7
• HTIBHCNKRMYWAG-UHFFFAOYSA-N methoxysulfonyl methyl sulfate Chemical compound COS(=O)(=O)OS(=O)(=O)OC HTIBHCNKRMYWAG-UHFFFAOYSA-N 0.000 claims description 5
• 150000003457 sulfones Chemical class 0.000 claims description 5
• 238000001556 precipitation Methods 0.000 claims description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 3
• 238000006243 chemical reaction Methods 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 4
• 238000003756 stirring Methods 0.000 description 3
• ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
• MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• 206010024229 Leprosy Diseases 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 238000005576 amination reaction Methods 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000005260 corrosion Methods 0.000 description 1
• 230000007797 corrosion Effects 0.000 description 1
• DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000003822 epoxy resin Substances 0.000 description 1
• -1 for example Chemical compound 0.000 description 1
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• CEFSVYOPCJUCQP-UHFFFAOYSA-N methyl sulfo sulfate Chemical compound COS(=O)(=O)OS(O)(=O)=O CEFSVYOPCJUCQP-UHFFFAOYSA-N 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 229920000647 polyepoxide Polymers 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• XAVPBEPMEPVYDL-UHFFFAOYSA-N sulfane sulfur dioxide Chemical compound S.O=S=O XAVPBEPMEPVYDL-UHFFFAOYSA-N 0.000 description 1
• UYTGDDAPMOSNND-UHFFFAOYSA-N sulfane sulfur trioxide Chemical compound S.O=S(=O)=O UYTGDDAPMOSNND-UHFFFAOYSA-N 0.000 description 1
• 125000001174 sulfone group Chemical group 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 239000013638 trimer Substances 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1