BE504707A - - Google Patents

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Publication number

BE504707A

BE504707A BE504707DA BE504707A BE 504707 A BE504707 A BE 504707A BE 504707D A BE504707D A BE 504707DA BE 504707 A BE504707 A BE 504707A

Authority

BE

Belgium

Prior art keywords

compounds

parts

general formula

compound

hal

Prior art date

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• 150000001875 compounds Chemical class 0.000 claims description 55
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
• 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 15
• -1 chloroacetyl-chlorophenylamide compounds Chemical class 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 13
• 238000006243 chemical reaction Methods 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 239000000463 material Substances 0.000 claims description 6
• 150000001450 anions Chemical class 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 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
• 238000002360 preparation method Methods 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 102000011782 Keratins Human genes 0.000 claims description 3
• 108010076876 Keratins Proteins 0.000 claims description 3
• 150000003868 ammonium compounds Chemical class 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 150000002790 naphthalenes Chemical class 0.000 claims description 3
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
• 229930195729 fatty acid Natural products 0.000 claims description 2
• 239000000194 fatty acid Substances 0.000 claims description 2
• 150000004665 fatty acids Chemical class 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims 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 claims 1
• SFFFBHOVGWZKNP-UHFFFAOYSA-N 2-chloro-n-[4-chloro-3-(trifluoromethyl)phenyl]acetamide Chemical class FC(F)(F)C1=CC(NC(=O)CCl)=CC=C1Cl SFFFBHOVGWZKNP-UHFFFAOYSA-N 0.000 claims 1
• 230000001747 exhibiting effect Effects 0.000 claims 1
• 229910052736 halogen Inorganic materials 0.000 claims 1
• 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 238000002844 melting Methods 0.000 description 19
• 230000008018 melting Effects 0.000 description 19
• 239000013078 crystal Substances 0.000 description 18
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
• 238000009835 boiling Methods 0.000 description 13
• 239000002244 precipitate Substances 0.000 description 13
• 235000019439 ethyl acetate Nutrition 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• 235000019441 ethanol Nutrition 0.000 description 8
• 238000004821 distillation Methods 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• 210000002268 wool Anatomy 0.000 description 6
• 239000000155 melt Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
• 241001077660 Molo Species 0.000 description 4
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 125000005843 halogen group Chemical group 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 239000001632 sodium acetate Substances 0.000 description 4
• 235000017281 sodium acetate Nutrition 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• 241000238631 Hexapoda Species 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 210000004209 hair Anatomy 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000000344 soap Substances 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 241000254171 Curculionidae Species 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 150000003931 anilides Chemical class 0.000 description 2
• 150000001491 aromatic compounds Chemical class 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 150000001805 chlorine compounds Chemical class 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
• 239000007859 condensation product Substances 0.000 description 2
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
• 229940052303 ethers for general anesthesia Drugs 0.000 description 2
• 239000004744 fabric Substances 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 150000004780 naphthols Chemical class 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 150000002989 phenols Chemical class 0.000 description 2
• 230000001376 precipitating effect Effects 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 238000005292 vacuum distillation Methods 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• SXQXMKMHOFIAHT-UHFFFAOYSA-N 1,1-dichloro-2-(2,2-dichloroethoxy)ethane Chemical compound ClC(Cl)COCC(Cl)Cl SXQXMKMHOFIAHT-UHFFFAOYSA-N 0.000 description 1
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
• AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
• 150000005003 1-naphthylamines Chemical class 0.000 description 1
• DHTGRDDBCWWKQJ-UHFFFAOYSA-N 2-(2,2-dihydroxyethoxy)ethane-1,1-diol Chemical compound OC(O)COCC(O)O DHTGRDDBCWWKQJ-UHFFFAOYSA-N 0.000 description 1
• SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
• SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
• 150000005004 2-naphthylamines Chemical class 0.000 description 1
• MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 1
• WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
• WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
• 241000208202 Linaceae Species 0.000 description 1
• 235000004431 Linum usitatissimum Nutrition 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 208000002474 Tinea Diseases 0.000 description 1
• 241000893966 Trichophyton verrucosum Species 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229940072049 amyl acetate Drugs 0.000 description 1
• PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
• 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 150000005840 aryl radicals Chemical class 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 150000001555 benzenes Chemical class 0.000 description 1
• 229940073608 benzyl chloride Drugs 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 125000006267 biphenyl group Chemical group 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 239000003518 caustics Substances 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 150000001804 chlorine Chemical class 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 125000003963 dichloro group Chemical group Cl* 0.000 description 1
• 229960004132 diethyl ether Drugs 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000004043 dyeing Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
• 150000002191 fatty alcohols Chemical class 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 210000003746 feather Anatomy 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000009963 fulling Methods 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 125000005179 haloacetyl group Chemical group 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 230000000974 larvacidal effect Effects 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 235000014571 nuts Nutrition 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
• 235000011007 phosphoric acid Nutrition 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 150000003388 sodium compounds Chemical class 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 229960004793 sucrose Drugs 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1
• 150000003738 xylenes Chemical class 0.000 description 1