US622854A - On-the-main - Google Patents
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- Publication number
- US622854A US622854A US622854DA US622854A US 622854 A US622854 A US 622854A US 622854D A US622854D A US 622854DA US 622854 A US622854 A US 622854A
- Authority
- US
- United States
- Prior art keywords
- sulfonic acid
- main
- acids
- nitrobenzyliden
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 10
- -1 NITROBENZYLIDEN Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 2
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 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 2
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical compound [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- MEXUXCVMECAUOM-UHFFFAOYSA-N benzyl-(2-nitrophenyl)sulfamic acid Chemical class [N+](=O)([O-])C1=C(N(S(=O)(=O)O)CC2=CC=CC=C2)C=CC=C1 MEXUXCVMECAUOM-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- CVMIVKAWUQZOBP-UHFFFAOYSA-L manganic acid Chemical compound O[Mn](O)(=O)=O CVMIVKAWUQZOBP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
- G03C7/4136—Developers p-Phenylenediamine or derivatives thereof
Definitions
- This invention relates to the production of orthoand paranitrobenzylanilin and its homologues.
- saltv vhere M represents a monovalent metal atom-for instance, Na, K, NH &c.
- potassium permanganate the equivalent quantities of other oxidizing agents may be emp1oyed-for instance, salts of alkali and alkaline earths of the manganic acid or permanganic acid, manganese dioxid, (MnO leadperoxid, (PbO ferric chlorid, (Fe Gh ferric sulfate, Fe (SO,) ferricyanid of potassium, ammonium persulfate, &c. It is of advantage to introduce carbonic acid or to add mangnesium sulfate. As soon as the violet color of the potassium permanganate has disappeared the oxidation is completed.
- Filtration is done from the precipitated manganese dioxid, and a clear yellow solution of the nitrobenzylidenanilinsulfonate salt or of a salt of the nitrobenzyliden-toluidin sulfonic acid, the nitrobenzyliden or Xylidin sulfonic acid, or the nitrobenzyliden-naphthylamin sulfonic acid remains behind. From this solution are obtained the solid salts either by salting out with chlorid of sodium or by evaporation. The salts thus obtained are yellowish powders, soluble in water, insoluble in the other usual mineral solvents.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
. and their homologues lose, under the influ- U NITED STATES PATENT OFFIcE.
BENNO HOMOLKA, OF FRANKFORT, AND AUGUST STOCK, OF HOOHST- ON-THE-MAIN, GERMANSI, ASSIGNORS TO THE FARBWERKE, VORMALS MEISTER, LUOIUS 85 BRUNING, OF HOOHST-ON-Tl-IE-MAIN, GERMANY.
NITROBENZYLIDEN SULFONIC ACID AND PROCESS OF MAKING SAME.
SPECIFICATION forming part of Letters Patent No. 622,854, dated April 1 1, 1899.
V, Application filedrDecember 15, I897- Serial No. 662,029. (SpecimensJ' V v .To all whom it may concern.-
Be it known that we, BENNO HoMoLKA, doctor of philosophy, a citizen of theEmpire of Austria-Hungary, residing at Frankforton-the-Main, and AUGUST STOCK, doctor of philosophy, a citizen of the Empire of Germany, residing at Hochst-on-the-Main, Germany, have invented certain new and useful Improvements in the Manufacture of Orthoand Para- Nitrobenzylidenanilinsulfonic Acids and Their Homologues, of Which the following is a description.
This invention relates to the production of orthoand paranitrobenzylanilin and its homologues.
We have found that the nitrobenzylanilinsulfonic acids, described in our American application, dated December 15, 1897, Serial No. 662,028, of the general formula Nitro- Benzyl Anilin Sulfonic acid ence of oxidizing agents, two atoms of hydrogen and are transformed into the nitrobenzylidenanilin sulfonic acids or their homologues according to the following equations:
2 e'. e., ortho-nitrobenzyliden anilinsulfonate Anilin sulfonic acid.
saltv vhere M represents a monovalent metal atom-for instance, Na, K, NH &c.
Thefree acids do not exist, but decompose completely, in presence of Water, into nitrobenzaldehyde and aromatic aminsulfonic acid according to the equations:
(1)OH=N.O H,SO H C l-I, I ,+H O:
2 Ortho=nitrobenzy1iden anilin sulfonic acid (1)COH 6 h 2 Ortho=nitrobenza1dehyd (1)CH':N.C H SO H V 0 7 4 2 (4:)NO Para-nitrobenzyliden-toluidin sulfonic acid (1)0OH Y 0 H H N. (3 H S0 11 Para-nitrobenzaldehyd Toluidin sulfonic acid. The nitrobenzylidenanilin sulfonic acids and their honiologues therefore form a particularly suitable material for the manufacture of orthoand paranitrobenzaldehyde.
We illustrate the practical application of our invention, for instance, as follows: Thirtythree kilograms of orthoor paranitrobenzylidenanilinsnlfonate of sodium (or the equivalent quantity of the salt of an orthoor paranitrobenzyliden-toluidin-sulfonic acid of an orthoor paranitrobenzyliden-Xylidin sulfonic acid, or of an orthoorparanitrobenzylnaphthylamin' sulfonic acid) are dissolved in water, whereupon a concentrated solution of 10.5 kilograms potassium permanganate (KMnO is slowly introduced While cooling and stirring rapidly. Instead of potassium permanganate the equivalent quantities of other oxidizing agents may be emp1oyed-for instance, salts of alkali and alkaline earths of the manganic acid or permanganic acid, manganese dioxid, (MnO leadperoxid, (PbO ferric chlorid, (Fe Gh ferric sulfate, Fe (SO,) ferricyanid of potassium, ammonium persulfate, &c. It is of advantage to introduce carbonic acid or to add mangnesium sulfate. As soon as the violet color of the potassium permanganate has disappeared the oxidation is completed. Filtration is done from the precipitated manganese dioxid, and a clear yellow solution of the nitrobenzylidenanilinsulfonate salt or of a salt of the nitrobenzyliden-toluidin sulfonic acid, the nitrobenzyliden or Xylidin sulfonic acid, or the nitrobenzyliden-naphthylamin sulfonic acid remains behind. From this solution are obtained the solid salts either by salting out with chlorid of sodium or by evaporation. The salts thus obtained are yellowish powders, soluble in water, insoluble in the other usual mineral solvents. The free sulfuric acids isolated in the usual way from these salts decompose, as already said above, into nitrobenzaldehyd and anilin sulfoacid 0r toluidin-sulfonic acid, Xylidin sulfonic acid, or naphthylamin-sulfonic acid.
Having now described our invention, what we claim is 1. The herein-described process for the mancomposition With diluted minerals acids, ni-
trobenzaldehyde, substantially as set forth.
In testimony that we claim the foregoing as our invention we have signed our names in presence of two subscribing witnesses.
BENNO HOMOLKA. AUGUST STOCK.
Witnesses:
HEINRICH HAHN, ALFRED BRISBISS.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US622854A true US622854A (en) | 1899-04-11 |
Family
ID=2691459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US622854D Expired - Lifetime US622854A (en) | On-the-main |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US622854A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277492A (en) * | 1980-05-21 | 1981-07-07 | The Dow Chemical Company | Novel 4-bis((Phenylmethyl)amino)-benzenesulfonic acids possessing antiviral activity |
| US4328244A (en) * | 1980-05-21 | 1982-05-04 | The Dow Chemical Company | Novel (((substituted-phenyl)methyl)amino)benzenesulfonic acids and pharmaceutically-acceptable salts thereof |
| US20090131941A1 (en) * | 2002-05-15 | 2009-05-21 | Ilwhan Park | Total joint arthroplasty system |
| CN110709693A (en) * | 2017-05-29 | 2020-01-17 | 荷兰联合利华有限公司 | Detergent composition and method for detecting the presence of a marker molecule in a solution |
-
0
- US US622854D patent/US622854A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277492A (en) * | 1980-05-21 | 1981-07-07 | The Dow Chemical Company | Novel 4-bis((Phenylmethyl)amino)-benzenesulfonic acids possessing antiviral activity |
| US4328244A (en) * | 1980-05-21 | 1982-05-04 | The Dow Chemical Company | Novel (((substituted-phenyl)methyl)amino)benzenesulfonic acids and pharmaceutically-acceptable salts thereof |
| US20090131941A1 (en) * | 2002-05-15 | 2009-05-21 | Ilwhan Park | Total joint arthroplasty system |
| CN110709693A (en) * | 2017-05-29 | 2020-01-17 | 荷兰联合利华有限公司 | Detergent composition and method for detecting the presence of a marker molecule in a solution |
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