DE117268C - - Google Patents
Info
- Publication number
- DE117268C DE117268C DENDAT117268D DE117268DA DE117268C DE 117268 C DE117268 C DE 117268C DE NDAT117268 D DENDAT117268 D DE NDAT117268D DE 117268D A DE117268D A DE 117268DA DE 117268 C DE117268 C DE 117268C
- Authority
- DE
- Germany
- Prior art keywords
- dinitronaphthalene
- sulfuric acid
- acid
- fuming sulfuric
- pure
- 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.)
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- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- XNKFCDGEFCOQOM-UHFFFAOYSA-N 1,2-dinitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C21 XNKFCDGEFCOQOM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- QTRNDORTMVTOEG-UHFFFAOYSA-N [O-][N+](=O)OS(=O)(=O)[N+]([O-])=O Chemical class [O-][N+](=O)OS(=O)(=O)[N+]([O-])=O QTRNDORTMVTOEG-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- NMMHJWYKFNBEFR-UHFFFAOYSA-N 2,3-dinitronaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=C([N+]([O-])=O)C([N+]([O-])=O)=CC2=C1 NMMHJWYKFNBEFR-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
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical group [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- XTXBFFMUMHUUNL-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C2=CC=CC=C2C=1)O)N=O Chemical class [N+](=O)([O-])C=1C(=C(C2=CC=CC=C2C=1)O)N=O XTXBFFMUMHUUNL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In den Patentschriften 90414 und 91391 ist mitgetheilt worden, dafs sowohl Ct1 a3-Dinitronaphtalin, wie Ci1 ct4-Dinitronaphtalin durch Behandeln mit einem gröfseren Ueberschufs von rauchender Schwefelsäure bei niedriger Temperatur in wasserunlösliche Körper übergeführt werden, welche von Grabe (Berichte XXXII, 2876) und von Friedländer (Berichte XXXII, 3528) übereinstimmend-als Nitronitrosonaphtole erkannt wurden.In patents 90414 and 91391 it was reported that both Ct 1 a 3 dinitronaphthalene and Ci 1 ct 4 dinitronaphthalene are converted into water-insoluble bodies by treatment with a large excess of fuming sulfuric acid at low temperature, which by Grabe (Reports XXXII , 2876) and by Friedländer (Reports XXXII, 3528) consistently-recognized as nitronitrosonaphthols.
Es wurde nun gefunden, dafs die Dinitronaphtaline beim Erhitzen mit schwach rauchender Schwefelsäure schon bei einer Temperatur von 80° in normalerweise in Dinitronaphtalinsulfosäuren übergehen, ohne dafs eine Umlagerung der einen Nitrogruppe stattfindet. Da die gebildeten Dinitrosulfosäuren gegen rauchende Schwefelsäure ziemlich indifferent sind, ist es ohne Belang, wenn eine gröfsere als die theoretisch erforderliche Menge Anhydrid zur Anwendung kommt. Aus Ct1 «4-Dinitronaphtalin wird eine fl1a4-Dinitronaphtalin-ßS!-monosulfosäure erhalten, die in ihren Eigenschaften mit der von Hellström (Oefversigt af Kongl. Vetenskaps- Akademiens Förhandligar, Stockholm. 1888. 10, 613) und in Patentschrift 67017 beschriebenen übereinstimmt; aus Ci1 ct3-Dinitronaphtalinentsteht die Ci1 a3-Dinitronaphtalinß2-monosulfosäure des Patentes 85058.It has now been found that the dinitronaphthalenes, when heated with weakly fuming sulfuric acid, are converted into dinitronaphthalenesulfonic acids normally at a temperature of 80 ° without any rearrangement of the one nitro group taking place. Since the dinitrosulfonic acids formed are quite indifferent to fuming sulfuric acid, it is of no consequence if an amount of anhydride greater than the theoretically required is used. Ct 1 « 4 -Dinitronaphtalin becomes a fl 1 a 4 -Dinitronaphtalin-ß S! -monosulfonic acid obtained, the properties of which correspond to those of Hellström (Oefversigt af Kongl. Vetenskaps- Akademiens Förhandligar, Stockholm. 1888. 10, 613) and described in patent 67017; Ci 1 ct 3 -Dinitronaphtalinent is the Ci 1 a 3 -Dinitronaphtalinß 2 -monosulfonic acid of the patent 85058.
40 kg rohes Dinitronaphtalin werden in 240 kg Schwefelsäuremonohydrat bei 100 bis iio° gelöst und in diese Lösung bei derselben Temperatur 80 kg rauchende Schwefelsäure von 20 pCt. S O3-Gehalt einfliefsen gelassen. Wenn kein unangegriffenes Dinitronaphtalin mehr vorhanden ist, wird die Sulfirungsmasse in dünne Kochsalzlösung eingerührt und nach kurzer Zeit scheiden sich die Natronsalze der Dinitrosulfosäuren als brauner krystallinischer Niederschlag vollständig ab. Durch Umkrystallisiren aus Alkohol können die Salze leicht rein erhalten werden.40 kg of crude dinitronaphthalene are dissolved in 240 kg of sulfuric acid monohydrate at 100 to 100 ° and in this solution at the same temperature 80 kg of fuming sulfuric acid of 20 pCt. S O 3 content allowed to flow. When there is no longer any unaffected dinitronaphthalene, the sulphurisation mass is stirred into a thin solution of common salt and after a short time the sodium salts of the dinitrosulphonic acids separate out completely as a brown crystalline precipitate. The salts can easily be obtained in pure form by recrystallization from alcohol.
Wendet man reines α-, α4-Dinitronaphtalin zur Sulfurirung an, so können die oben angegebenen Verhältnisse beibehalten werden; bei Verwendung von reinem Ci1 ci3 - Dinitronaphtalin ist dagegen eine etwas gröfsere Menge rauchender Schwefelsäure erforderlich.If pure α-, α 4 -dinitronaphthalene is used for sulfurization, the above-mentioned ratios can be maintained; when using pure Ci 1 ci 3 - dinitronaphthalene, on the other hand, a somewhat larger amount of fuming sulfuric acid is required.
Das Ci1 a4-dinitronaphtalin-ß2-sulfosaure Natron löst sich in circa 6,5 Theile kochendem Wasser und krystallisirt daraus in kleinen farblosen Nadeln. Die wässerige Lösung wird durch Schwefelnatrium zuerst tief gelb und dann rein blau gefärbt. Der Schmelzpunkt vom Sulfochlorid wurde bei 143 bis 1440 gefunden (Hellström: 145°).The Ci 1 a 4 -dinitronaphthalene-β 2 -sulphous acid soda dissolves in about 6.5 parts of boiling water, and crystallizes from it in small, colorless needles. The aqueous solution is first colored deep yellow and then pure blue by sodium sulphide. The melting point of the sulfochloride was found to be 143 to 144 0 (Hellström: 145 °).
Das H1 a3-dinitronaphtalin-ß2-sulfosaure Natron löst sich in circa 12 Theilen kochenden Wassers und krystallisirt daraus in langen vveifsen Nadeln. Die wässerige Lösung wird durch Schwefelnatrium nur schwach gelb gefärbt. Durch Behandeln mit neutralem oder saurem Natriumsulfit wird eine Nitronaphtylaminsulfosäure gebildet. Durch die Einwirkung vonThe H 1 a 3 -dinitronaphthalene-β 2 -sulphous acid soda dissolves in about 12 parts of boiling water and crystallizes from it in long, veined needles. The aqueous solution is only slightly yellow in color due to sodium sulphide. Treatment with neutral or acidic sodium sulfite forms a nitronaphthylamine sulfonic acid. By the action of
rauchender Schwefelsäure in Gegenwart von Reductionsmitteln entsteht ein in Wasser blau lösliches Zwischenproduct, das durch Kochen in eine Naphtazarinsulfosäure übergeführt wird. Das aus Chloroform in derben Prismen krystallisirendeSulfochloridderDinitrosulfosäure schmilzt bei 118 bis ι iq°.fuming sulfuric acid in the presence of reducing agents creates a blue in water soluble intermediate product which is converted into a naphtazarin sulphonic acid by boiling. The sulfochloride of dinitro sulfonic acid, which crystallizes from chloroform in coarse prisms melts at 118 to ι iq °.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE117268C true DE117268C (en) |
Family
ID=386544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT117268D Active DE117268C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE117268C (en) |
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