DE145190C - - Google Patents
Info
- Publication number
- DE145190C DE145190C DENDAT145190D DE145190DA DE145190C DE 145190 C DE145190 C DE 145190C DE NDAT145190 D DENDAT145190 D DE NDAT145190D DE 145190D A DE145190D A DE 145190DA DE 145190 C DE145190 C DE 145190C
- Authority
- DE
- Germany
- Prior art keywords
- nitroresorcinol
- resorcinol
- acid
- nitrated
- specific weight
- 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
Links
- ZLCPKMIJYMHZMJ-UHFFFAOYSA-N 2-nitrobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1[N+]([O-])=O ZLCPKMIJYMHZMJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- GQTHXQVZAKGYGN-UHFFFAOYSA-N 2,4-dihydroxybenzene-1,3-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C(O)=C1S(O)(=O)=O GQTHXQVZAKGYGN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VBDSIPITQVYVRX-UHFFFAOYSA-N 1-nitrocyclohexa-3,5-diene-1,3-diol Chemical compound OC1=CC=CC(O)([N+]([O-])=O)C1 VBDSIPITQVYVRX-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitrogen oxide Substances O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N Potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- MBXIRNHACKAGPA-UHFFFAOYSA-N 4,6-Dinitroresorcinol Chemical compound OC1=CC(O)=C([N+]([O-])=O)C=C1[N+]([O-])=O MBXIRNHACKAGPA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 229910052813 nitrogen oxide Inorganic materials 0.000 description 1
- -1 potassium chlorine Chemical compound 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Entstehung von 1 · 2 · 3-Nitroresorcin als Nebenprodukt wurde schon bei der Einwirkung von Salpetersäure auf ätherische Resorcinlösung beobachtet (Monatshefte f. Chemie I, 887), auch wurde es durch Spaltung von Nitrofluorescein, sowie vonNitromethylumbelliferon (Ber. XXXlV, 660) erhalten. Nach keinem dieser Verfahren ist eine technische Darstellung des 1 · 2 · 3-Nitroresorcins möglich.The formation of 1 · 2 · 3-nitroresorcinol as a by-product was already evident upon exposure observed from nitric acid on essential resorcinol solution (monthly notebooks f. Chemistry I, 887), too it was obtained by cleavage of nitrofluorescein and nitromethylumbelliferone (Ber. XXXlV, 660) received. Neither of these procedures is a technical representation of the 1x2x3-nitroresorcinol possible.
Außerdem ist in der Patentschrift 127283 ein Verfahren zur Darstellung von Nitroresorcin beschrieben, das von Acetmetanilsäure ausgeht; das entstehende Nitroresorcin ist indes ohne Zweifel das as. Nitroresorcin 1 · 2 · 4.In addition, the patent specification 127283 discloses a method for the preparation of nitroresorcinol described that starts from acetmetanilic acid; the resulting nitroresorcinol, however, is without Doubt the as. Nitroresorcinol 1 · 2 · 4.
Es wurde nun ein Verfahren gefunden, das die Herstellung desNitroresorcins (OH: N0.2: OH= 1:2:3) m einfachster Weise von Resorcin bezw. dessen Sulfosäuren ausgehend gestattet, während dies bisher nicht gelungen ist. Das Verfahren besteht darin, daß man Resorcindisulfosäure nitriert und aus dem entstehenden Nitroprodukt die Sulfogruppen abspaltet.It has been found now a process which comprises preparing desNitroresorcins (OH: 3 N0. 2: OH = 1: 2) m BEZW einfachster way of resorcinol. whose sulfonic acids are permitted, while this has not yet been achieved. The process consists in nitrating resorcinol disulfonic acid and splitting off the sulfo groups from the nitro product formed.
Bei der Nitrierung der schon bekannten Resorcindisulfosäure (vergl. Ber. IX, 1479; Monatshefte f. Chemie II, 331) ist für Kühlung Sorge zu tragen, da anderenfalls leicht Entwicklung von Stickoxyden stattfindet und auch die Bildung von mehrfach nitrierten Körpern begünstigt ist. Die Abspaltung der Sulfogruppen aus dem gebildeten Nitroprodukt wird bewirkt, indem man dasselbe mit Schwefelsäure unter Zusatz von Wasser kocht. Für diesen Zweck ist es nicht notwendig, das Nitroprodukt zu isolieren, was leicht in Form des Kaliumsalzes durch Zusatz von Chlorkalium geschehen kann, vielmehr kann man die Reaktionsmasse, wie man sie durch Sulfurieren von Resorcin und nachfolgendes Nitrieren erhält, direkt mit Wasser versetzen und mit überhitztem Dampf das Nitroresorcin abdestillieren.In the nitration of the well-known resorcinol disulfonic acid (cf. Ber. IX, 1479; Monthly booklets f. Chemistry II, 331) care must be taken to keep it cool, otherwise it can develop easily of nitrogen oxides takes place and also the formation of multiply nitrided bodies is favored. The elimination of the sulfo groups from the nitro product formed is effected by boiling it with sulfuric acid with the addition of water. For this purpose it is not necessary to isolate the nitro product, which can easily be in the form of the potassium salt can be done by adding potassium chlorine, rather you can the reaction mass, such as they are obtained by sulphurising resorcinol and then nitriding, directly with water add and distill off the nitroresorcinol with superheated steam.
In 440 g concentrierter Schwefelsäure (spez. Gew. 1,875) werden unter Erwärmen 44 Teile gepulvertes Resorcin eingetragen. Wenn die Sulfierung vollendet ist, läßt man erkalten und läßt unter Kühlung eine Mischung von 28 g Salpetersäure (spez. Gew. 1,52) und 80g Schwefelsäure (spez. Gew. 1,875) unter Umrühren einfließen. Dabei wird der Brei dünner, und nach mehrstündigem Stehen ist fast alles in Lösung gegangen. Alsdann gibt man 400 ecm Wasser zu und destilliert durch überhitzten Dampf das Nitroresorcin ab.In 440 g of concentrated sulfuric acid (specific weight 1.875) 44 parts are obtained with heating powdered resorcinol entered. When the sulfonation is complete, it is allowed to cool and leaves a mixture of 28 g of nitric acid (specific weight 1.52) and 80 g of sulfuric acid with cooling (specific weight 1.875) pour in with stirring. The pulp becomes thinner, and after standing for several hours almost everything went into solution. Then you give 400 ecm Water is added and the nitroresorcinol is distilled off using superheated steam.
Durch ihren Schmelzpunkt 850, sowie ihre Flüchtigkeit ist die erhaltene Verbindung als das Nitroresorcin charakterisiert, in dem die Substituenten die Stellung 1 · 2 · 3 einnehmen.The compound obtained is characterized by its melting point 85 ° and its volatility as nitroresorcinol, in which the substituents are in the 1 · 2 · 3 position.
Es ist selbstverständlich, daß bei der Nitrierung des sulfurierten Resorcins die Salpetersäure auch durch Salpeter ersetzt werden kann.It goes without saying that when the sulfurized resorcinol is nitrated, nitric acid can also be replaced by saltpetre.
Als Nebenprodukt des Nitroresorcins lassen sich in der sauren Flüssigkeit, aus der das Nitroresorcin mit Wasserdampf abgetrieben wurde, ein Dinitroresorcin sowie eine nitrierte Sulfosäure des Resorcins nachweisen.As a by-product of nitroresorcinol, the acidic liquid from which the Nitroresorcinol was driven off with steam, a dinitroresorcinol and a nitrated one Detect sulphonic acid of resorcinol.
Das ι · 2 · 3-Nitroresorcin findet Verwendung zur Herstellung von Farbstoffen und für Zwecke der Photographie.The ι · 2 · 3-nitroresorcinol is used for the production of dyes and for purposes of photography.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE145190C true DE145190C (en) | 1900-01-01 |
Family
ID=412556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT145190D Expired DE145190C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE145190C (en) |
-
0
- DE DENDAT145190D patent/DE145190C/de not_active Expired
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