CA2070663C - Sulfonating agent and process - Google Patents
Sulfonating agent and process Download PDFInfo
- Publication number
- CA2070663C CA2070663C CA002070663A CA2070663A CA2070663C CA 2070663 C CA2070663 C CA 2070663C CA 002070663 A CA002070663 A CA 002070663A CA 2070663 A CA2070663 A CA 2070663A CA 2070663 C CA2070663 C CA 2070663C
- Authority
- CA
- Canada
- Prior art keywords
- sulfonic acid
- sulfonating
- aromatic
- aromatic compound
- acid
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 26
- -1 aromatic amine compound Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 13
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 claims description 12
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- QJSRFGIVFRUUKG-UHFFFAOYSA-N 2,3,4,5,6-pentamethylbenzenesulfonic acid Chemical compound CC1=C(C)C(C)=C(S(O)(=O)=O)C(C)=C1C QJSRFGIVFRUUKG-UHFFFAOYSA-N 0.000 claims description 4
- CTQUHMJRQMWPKN-UHFFFAOYSA-N 2,3,4,6-tetramethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1C CTQUHMJRQMWPKN-UHFFFAOYSA-N 0.000 claims description 4
- KJJMOCUMRBSKTE-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(C)C(S(O)(=O)=O)=C1C KJJMOCUMRBSKTE-UHFFFAOYSA-N 0.000 claims description 4
- IHGWXBWYZUMHLR-UHFFFAOYSA-N 2,4,6-triethylbenzenesulfonic acid Chemical compound CCC1=CC(CC)=C(S(O)(=O)=O)C(CC)=C1 IHGWXBWYZUMHLR-UHFFFAOYSA-N 0.000 claims description 4
- ZNLSYQWAJLYIOZ-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-disulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1S(O)(=O)=O ZNLSYQWAJLYIOZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 59
- 239000000243 solution Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 31
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 238000010812 external standard method Methods 0.000 description 14
- 125000000542 sulfonic acid group Chemical group 0.000 description 14
- 238000006277 sulfonation reaction Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002699 waste material Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 229920002492 poly(sulfone) Polymers 0.000 description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 2
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- CXZOCEZMGWOOFD-UHFFFAOYSA-N phenanthren-1-amine Chemical compound C1=CC2=CC=CC=C2C2=C1C(N)=CC=C2 CXZOCEZMGWOOFD-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- MKQJRXLAJNHANO-UHFFFAOYSA-N (4-methoxyphenyl)-sulfosulfamic acid Chemical compound COC1=CC=C(N(S(O)(=O)=O)S(O)(=O)=O)C=C1 MKQJRXLAJNHANO-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical class ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- KZNJSFHJUQDYHE-UHFFFAOYSA-N 1-methylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=CC2=C1 KZNJSFHJUQDYHE-UHFFFAOYSA-N 0.000 description 1
- ZAPYLSLVQJQGEY-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-amine Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3N)=CC=CC2=C1 ZAPYLSLVQJQGEY-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- LTVGUIAXXNMYRT-UHFFFAOYSA-N 2,3,4,5,6-pentaethylbenzenesulfonic acid Chemical compound CCC1=C(CC)C(CC)=C(S(O)(=O)=O)C(CC)=C1CC LTVGUIAXXNMYRT-UHFFFAOYSA-N 0.000 description 1
- VVZMWPOBDPSOLJ-UHFFFAOYSA-N 2,3,4,5-tetramethylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(C)C(C)=C1C VVZMWPOBDPSOLJ-UHFFFAOYSA-N 0.000 description 1
- XNJVIJQATFJERB-UHFFFAOYSA-N 2,3,4-trimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C)=C1C XNJVIJQATFJERB-UHFFFAOYSA-N 0.000 description 1
- GMAVOKCCIVJURU-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-disulfonic acid Chemical compound CC1=C(C)C(S(O)(=O)=O)=C(C)C(C)=C1S(O)(=O)=O GMAVOKCCIVJURU-UHFFFAOYSA-N 0.000 description 1
- KNRWYSXDLZUMBO-UHFFFAOYSA-N 2,3,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1C KNRWYSXDLZUMBO-UHFFFAOYSA-N 0.000 description 1
- RFDZNGIWELUYOT-UHFFFAOYSA-N 2,4,5-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C=C1C RFDZNGIWELUYOT-UHFFFAOYSA-N 0.000 description 1
- YHGKEORTCHVBQH-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC(C(C)C)=C(S(O)(=O)=O)C(C(C)C)=C1 YHGKEORTCHVBQH-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CXOWHCCVISNMIX-UHFFFAOYSA-N 2-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(N)=CC=C21 CXOWHCCVISNMIX-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WONRDHPFOHAWOG-UHFFFAOYSA-N 2-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(Cl)C=CC2=C1 WONRDHPFOHAWOG-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- RURDPZYLLQHSDR-UHFFFAOYSA-N 2-ethyl-4,5-dimethylbenzenesulfonic acid Chemical compound CCC1=CC(C)=C(C)C=C1S(O)(=O)=O RURDPZYLLQHSDR-UHFFFAOYSA-N 0.000 description 1
- IQRJHSFBLQGIIE-UHFFFAOYSA-N 2-ethyl-4,6-dimethylbenzenesulfonic acid Chemical compound CCC1=CC(C)=CC(C)=C1S(O)(=O)=O IQRJHSFBLQGIIE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- PEXGTUZWTLMFID-UHFFFAOYSA-N 2-phenyldiazenylphenol Chemical compound OC1=CC=CC=C1N=NC1=CC=CC=C1 PEXGTUZWTLMFID-UHFFFAOYSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- DAHXFCMWZOXMPP-UHFFFAOYSA-N 4-ethyl-2,6-dimethylbenzenesulfonic acid Chemical compound CCC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 DAHXFCMWZOXMPP-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical group OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000035871 PIK3CA-related overgrowth syndrome Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VMICULCQFMPUQV-UHFFFAOYSA-N n-chloronaphthalen-1-amine Chemical compound C1=CC=C2C(NCl)=CC=CC2=C1 VMICULCQFMPUQV-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- SXAUVYZLBJSWNT-UHFFFAOYSA-N n-methoxynaphthalen-1-amine Chemical compound C1=CC=C2C(NOC)=CC=CC2=C1 SXAUVYZLBJSWNT-UHFFFAOYSA-N 0.000 description 1
- AKEYUWUEAXIBTF-UHFFFAOYSA-N n-methylnaphthalen-1-amine Chemical compound C1=CC=C2C(NC)=CC=CC2=C1 AKEYUWUEAXIBTF-UHFFFAOYSA-N 0.000 description 1
- XSCFKJGIAYKLRV-UHFFFAOYSA-N n-naphthalen-1-ylnitramide Chemical compound C1=CC=C2C(N[N+](=O)[O-])=CC=CC2=C1 XSCFKJGIAYKLRV-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical class C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/02—Formation or introduction of functional groups containing sulfur of sulfo or sulfonyldioxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP273725/1990 | 1990-10-12 | ||
| JP27372590 | 1990-10-12 | ||
| PCT/JP1991/001372 WO1992006935A1 (en) | 1990-10-12 | 1991-10-09 | Sulfonating agent and process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2070663A1 CA2070663A1 (en) | 1992-04-13 |
| CA2070663C true CA2070663C (en) | 2002-05-07 |
Family
ID=17531694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002070663A Expired - Lifetime CA2070663C (en) | 1990-10-12 | 1991-10-09 | Sulfonating agent and process |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5596128A (en:Method) |
| EP (1) | EP0505582B1 (en:Method) |
| KR (1) | KR0185224B1 (en:Method) |
| CA (1) | CA2070663C (en:Method) |
| DE (1) | DE69121188T2 (en:Method) |
| TW (1) | TW198708B (en:Method) |
| WO (1) | WO1992006935A1 (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048904A (en) * | 1998-12-01 | 2000-04-11 | Exxon Research And Engineering Co. | Branched alkyl-aromatic sulfonic acid dispersants for solublizing asphaltenes in petroleum oils |
| US7754844B2 (en) * | 2002-10-08 | 2010-07-13 | Toyo Boseki Kabushiki Kaisha | Polyarylene ether compound containing sulfonic acid group, composition containing same, and method for manufacturing those |
| US8187734B2 (en) | 2004-11-10 | 2012-05-29 | Toyo Boseki Kabushiki Kaisha | Proton-conducting polymer composition and method for preparation thereof, catalyst ink containing said proton-conducting polymer composition and fuel cell including said catalyst ink |
| JPWO2006137473A1 (ja) * | 2005-06-24 | 2009-01-22 | 日産化学工業株式会社 | 芳香族スルホン酸化合物の製造法 |
| EP3205698B1 (en) | 2006-06-15 | 2020-05-13 | Dow Global Technologies LLC | Functionalized olefin interpolymers, compositions and articles prepared therefrom, and methods for making the same |
| JP4836080B2 (ja) * | 2007-01-09 | 2011-12-14 | 小西化学工業株式会社 | スルホン化排出液の処理方法及びスルホン化排出液のリサイクル方法 |
| KR101731242B1 (ko) | 2011-12-22 | 2017-04-28 | 고니시가가꾸고오교가부시끼가이샤 | 방향족 폴리머의 술폰화물의 제조방법 |
| CN103936636B (zh) * | 2013-01-23 | 2016-05-25 | 中国科学院大连化学物理研究所 | 一种甲苯磺化制备对甲苯磺酸的方法 |
| CN103274971B (zh) * | 2013-06-19 | 2014-08-06 | 太仓沪试试剂有限公司 | 一种5-磺基水杨酸的纯化方法 |
| CN104447420B (zh) * | 2014-10-29 | 2016-08-24 | 宁夏共享化工有限公司 | 一种铸造砂型喷墨打印树脂用磺酸固化剂的生产方法 |
| CN105968033B (zh) * | 2016-05-12 | 2018-02-16 | 浙江正大新材料科技有限公司 | 一种3,4‑二氯苯胺‑6‑磺酸的生产方法 |
| CN106146356B (zh) * | 2016-07-01 | 2018-07-20 | 宁夏紫光川庆化工有限公司 | 连续生产1-萘磺酸的方法 |
| CN106831500A (zh) * | 2017-01-19 | 2017-06-13 | 南通海之阳膜化工有限公司 | 一种g盐及其副产物r盐的制备方法 |
| CN108863856B (zh) * | 2018-06-15 | 2021-06-01 | 永华化学股份有限公司 | 一种分析纯试剂5-磺基水杨酸提纯方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3222393A (en) * | 1962-05-07 | 1965-12-07 | Union Oil Co | 1,2,3,4-tetraalkyl benzene sulfonic acid production |
| GB1434019A (en) * | 1972-10-30 | 1976-04-28 | Koebner A | Sulphonation of aromatic compounds |
-
1991
- 1991-10-09 DE DE69121188T patent/DE69121188T2/de not_active Expired - Lifetime
- 1991-10-09 EP EP91919286A patent/EP0505582B1/en not_active Expired - Lifetime
- 1991-10-09 WO PCT/JP1991/001372 patent/WO1992006935A1/ja active IP Right Grant
- 1991-10-09 CA CA002070663A patent/CA2070663C/en not_active Expired - Lifetime
- 1991-10-09 KR KR1019920701398A patent/KR0185224B1/ko not_active Expired - Lifetime
- 1991-10-12 TW TW081104798A patent/TW198708B/zh active
-
1994
- 1994-09-06 US US08/300,844 patent/US5596128A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992006935A1 (en) | 1992-04-30 |
| DE69121188T2 (de) | 1997-01-02 |
| TW198708B (en:Method) | 1993-01-21 |
| EP0505582A1 (en) | 1992-09-30 |
| EP0505582A4 (en) | 1993-03-31 |
| CA2070663A1 (en) | 1992-04-13 |
| KR0185224B1 (ko) | 1999-05-15 |
| EP0505582B1 (en) | 1996-07-31 |
| KR927003488A (ko) | 1992-12-18 |
| DE69121188D1 (de) | 1996-09-05 |
| US5596128A (en) | 1997-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |