DE181179C - - Google Patents

Info

Publication number

DE181179C

DE181179C DE1905181179D DE181179DA DE181179C DE 181179 C DE181179 C DE 181179C DE 1905181179 D DE1905181179 D DE 1905181179D DE 181179D A DE181179D A DE 181179DA DE 181179 C DE181179 C DE 181179C

Authority

DE

Germany

Prior art keywords

acid

sulfonic acid

aminodiphenylamine

percent

water

Prior art date

1905-11-21

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

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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 10
• ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 10
• 239000000155 melt Substances 0.000 claims description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
• 150000008064 anhydrides Chemical class 0.000 claims description 6
• KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims description 4
• 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
• 150000004682 monohydrates Chemical class 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
• 238000000034 method Methods 0.000 claims 2
• ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims 1
• 239000003153 chemical reaction reagent Substances 0.000 claims 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 17
• 239000000243 solution Substances 0.000 description 5
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 125000003003 spiro group Chemical group 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 238000009835 boiling Methods 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
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 230000001376 precipitating effect Effects 0.000 description 2
• 238000001226 reprecipitation Methods 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
• 238000005987 sulfurization reaction Methods 0.000 description 2
• FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
• IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 150000008049 diazo compounds Chemical class 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 239000003973 paint Substances 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1