DE148110C - - Google Patents
Info
- Publication number
- DE148110C DE148110C DENDAT148110D DE148110DA DE148110C DE 148110 C DE148110 C DE 148110C DE NDAT148110 D DENDAT148110 D DE NDAT148110D DE 148110D A DE148110D A DE 148110DA DE 148110 C DE148110 C DE 148110C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amido
- sulfuric acid
- acids
- heated
- 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.)
- Active
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- 239000005711 Benzoic acid Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- AIWWFEBAHIXODC-UHFFFAOYSA-N 2h-anthracene-1,9,10-trione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(=O)CC=C2 AIWWFEBAHIXODC-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 14
- 125000003368 amide group Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 5
- -1 monooxybenzoylbenzoic acid derivatives Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 150000005171 halobenzenes Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000003022 phthalic acids Chemical class 0.000 description 2
- 239000012262 resinous product Substances 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- XNAREJANYHLQSW-UHFFFAOYSA-N 2-benzoyl-3,4-dimethoxybenzoic acid Chemical class COc1ccc(C(O)=O)c(C(=O)c2ccccc2)c1OC XNAREJANYHLQSW-UHFFFAOYSA-N 0.000 description 1
- JEZQCHJJLYRNOZ-UHFFFAOYSA-N 2-benzoyl-3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 JEZQCHJJLYRNOZ-UHFFFAOYSA-N 0.000 description 1
- JITXOIOEKZVBBI-UHFFFAOYSA-N 2-benzoyl-3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1C(=O)C1=CC=CC=C1 JITXOIOEKZVBBI-UHFFFAOYSA-N 0.000 description 1
- VQCAQTNPROLAJK-UHFFFAOYSA-N 2-benzoyl-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 VQCAQTNPROLAJK-UHFFFAOYSA-N 0.000 description 1
- ZHXJPZWBJBDDTE-UHFFFAOYSA-N 2-benzoyl-4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 ZHXJPZWBJBDDTE-UHFFFAOYSA-N 0.000 description 1
- FUDJXNWNBSSUKI-UHFFFAOYSA-N 2-benzoyl-4-methoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C(C(=O)C=2C=CC=CC=2)=C1 FUDJXNWNBSSUKI-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE148110C true DE148110C (en:Method) |
Family
ID=415229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT148110D Active DE148110C (en:Method) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE148110C (en:Method) |
-
0
- DE DENDAT148110D patent/DE148110C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE148110C (en:Method) | ||
| DE282711C (en:Method) | ||
| DE205036C (en:Method) | ||
| DE185663C (en:Method) | ||
| DE484357C (de) | Verfahren zur Herstellung von Acidyl- und Halogenderivaten des 1íñ4-Diaminoanthrachinons | |
| DE167699C (en:Method) | ||
| DE2248704B2 (en:Method) | ||
| DE234742C (en:Method) | ||
| DE292395C (en:Method) | ||
| DE508322C (de) | Verfahren zur Darstellung von Benzanthronderivaten | |
| DE326486C (de) | Verfahren zur Darstellung der Nitroverbindungen von im aromatischen oder Cyklohexenring durch Hydroxyl- oder Aminogruppen substituierten Tetrahydronaphthalinen und Alkyltetrahydronaphthalinen | |
| DE234917C (en:Method) | ||
| DE268984C (en:Method) | ||
| DE510435C (de) | Verfahren zur Darstellung von negativ substituierten Carbazolen | |
| DE2846432C2 (en:Method) | ||
| DE295817C (en:Method) | ||
| DE148109C (en:Method) | ||
| DE275833C (en:Method) | ||
| DE167410C (en:Method) | ||
| DE180157C (en:Method) | ||
| Bogert et al. | RESEARCHES ON QUINAZOLINES (TWENTY-FIFTH PAPER). THE SYNTHESIS OF 6-AND 7-AMINO-2-METHYL-4-QUINAZOLONES FROM 4-AND 5-ACETAMINOACETANTHRANILS. | |
| DE156388C (en:Method) | ||
| DE98637C (en:Method) | ||
| DE282374C (en:Method) | ||
| DE947167C (de) | Verfahren zur Herstellung von 1-Aminobenzophenonsulfon-2-carbonsaeuren bzw. deren Estern |