CH396885A - Herstellung von Halogendiphenylsulfonen - Google Patents

Info

Publication number

CH396885A

CH396885A CH7323559A CH7323559A CH396885A CH 396885 A CH396885 A CH 396885A CH 7323559 A CH7323559 A CH 7323559A CH 7323559 A CH7323559 A CH 7323559A CH 396885 A CH396885 A CH 396885A

Authority

CH

Switzerland

Prior art keywords

oxidizing agent

potassium

nitrate

halodiphenyl

nitric acid

Prior art date

1958-05-17

Links

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• 150000003457 sulfones Chemical class 0.000 title claims description 23
• 238000004519 manufacturing process Methods 0.000 title claims description 7
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 24
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
• 239000007800 oxidant agent Substances 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 13
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 11
• 229910017604 nitric acid Inorganic materials 0.000 claims description 11
• 150000005171 halobenzenes Chemical class 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
• XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 3
• 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
• 150000001555 benzenes Chemical group 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 2
• 239000004615 ingredient Substances 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 235000010344 sodium nitrate Nutrition 0.000 claims description 2
• 239000004317 sodium nitrate Substances 0.000 claims description 2
• IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 claims 2
• KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims 2
• FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 2
• QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 claims 1
• PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims 1
• 230000001419 dependent effect Effects 0.000 claims 1
• SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims 1
• RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 claims 1
• VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 claims 1
• 235000010333 potassium nitrate Nutrition 0.000 claims 1
• 239000004323 potassium nitrate Substances 0.000 claims 1
• 239000012286 potassium permanganate Substances 0.000 claims 1
• USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims 1
• 235000019394 potassium persulphate Nutrition 0.000 claims 1
• XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• 150000002823 nitrates Chemical class 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• -1 ether peroxides Chemical class 0.000 description 2
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
• 230000000895 acaricidal effect Effects 0.000 description 1
• 239000000642 acaricide Substances 0.000 description 1
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
• 238000006482 condensation reaction Methods 0.000 description 1
• 238000010924 continuous production Methods 0.000 description 1
• KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 239000002917 insecticide Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• 150000001451 organic peroxides Chemical class 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• OQBAIYJURBWUML-UHFFFAOYSA-N sulfurochloridic acid 1,2,4-trichlorobenzene Chemical compound S(=O)(=O)(O)Cl.ClC1=CC=C(C(=C1)Cl)Cl OQBAIYJURBWUML-UHFFFAOYSA-N 0.000 description 1