DE221967C - - Google Patents
Info
- Publication number
- DE221967C DE221967C DENDAT221967D DE221967DA DE221967C DE 221967 C DE221967 C DE 221967C DE NDAT221967 D DENDAT221967 D DE NDAT221967D DE 221967D A DE221967D A DE 221967DA DE 221967 C DE221967 C DE 221967C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- parts
- sodium salt
- sulfonic 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.)
- Active
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- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N Ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- FPBOSUGVPBRYCA-UHFFFAOYSA-N (4-nitrophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 FPBOSUGVPBRYCA-UHFFFAOYSA-N 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N Benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- -1 aryl carbamates Chemical class 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants Carbamic acid esters Drugs 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- MYDQAEQZZKVJSL-UHFFFAOYSA-N pentyl carbamate Chemical compound CCCCCOC(N)=O MYDQAEQZZKVJSL-UHFFFAOYSA-N 0.000 description 1
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 221967 KLASSE 12 o. GRUPPE- M 221967 CLASS 12 or GROUP
Patentiert im Deutschen Reiche vom 11. Juli 1909 ab.Patented in the German Empire on July 11, 1909.
Es hat sich gezeigt, daß die Carbaminsäurealkyl- und -aralkylester der 2-Amino-5-naphtol-7-sulfosäure (J-Säure) von der allgemeinen FormelIt has been shown that the carbamic acid alkyl and aralkyl esters of 2-amino-5-naphthol-7-sulfonic acid (J-acid) from the general formula
' \ ~ '\ ~ ΛΛ NH.COORNH.COOR
OHOH
in der R — Alkyl oder Aralkyl ist, außergewöhnlich leicht und glatt erhalten werden, wenn man die Chlorkohlensäurealkyl- oder -aralkylester auf die genannte Aminonaphtolsulfosäure zweckmäßig in Gegenwart von mineralsäurebindenden Mitteln einwirken läßt. Die erhaltenen Carbaminsäureester zeichnen sich im Gegensatz zu den entsprechenden Carbaminsäurearylestern, welche sich zum Teil schon in wäßriger Lösung wieder zersetzen, durch große Beständigkeit aus und bilden ein außerordentlich wertvolles und billiges Ausgangsmaterial zur Herstellung von Farbstoffen.in which R - is alkyl or aralkyl, can be obtained exceptionally easily and smoothly if the chlorocarbonic acid alkyl or aralkyl esters are allowed to act on the aminonaphthol sulfonic acid mentioned, expediently in the presence of mineral acid binding agents. In contrast to the corresponding aryl carbamates, some of which already decompose again in aqueous solution, the carbamic acid esters obtained are distinguished by great stability and are an extremely valuable and inexpensive starting material for the production of dyes.
2r Beispiel I. 2 r example I.
261 Teile 2 · 5 · 7 - aminonaphtolsulfosaures Natron werden mit 700 Teilen Wasser angerührt ; hierzu läßt man unter Umrühren etwa 120 Teile Chlorkohlensäureäthylester langsam zufließen. Wenn der Geruch nach diesem verschwunden ist, verdünnt man mit Wasser und filtriert die Lösung des Natriumsalzes des Carbaminsäureäthylesters der J - Säure von ausgeschiedener J-Säure ab.261 parts of 2 · 5 · 7-aminonaphtholsulfonate of soda are mixed with 700 parts of water ; for this purpose, about 120 parts of ethyl chlorocarbonate are slowly allowed to stir while stirring flow in. When the smell after this has disappeared, dilute with water and the solution of the sodium salt of the ethyl carbamic acid ester of I-acid is filtered off precipitated J-acid from.
35 Beispiel II. 35 Example II.
239 Teile 2 - Amino - 5 - naphtol - 7 - sulfosäure werden mit 700 Teilen Wasser aufgeschlemmt, 100 Teile calcinierte Soda und 34 Teile kristallisiertes Natriumacetat zugefügt; man läßt unter Umrühren so viel Chlorkohlensäureäthylester allmählich zutropfen, bis sich eine Probe, der Flüssigkeit, mit Säure und Nitrit versetzt, auf Sodazusatz nicht mehr rot, sondern rein gelb färbt.239 parts of 2 - amino - 5 - naphthol - 7 - sulfonic acid are suspended in 700 parts of water, 100 parts of soda ash and 34 parts of crystallized sodium acetate were added; one lets Gradually add dropwise as much chlorocarbonic acid ethyl ester, while stirring, until a sample the liquid, mixed with acid and nitrite, is no longer red when soda is added, but pure turns yellow.
Das in Wasser sehr leicht lösliche Natriumsalz des gebildeten Carbaminsäureäthylesters der J-Säure kristallisiert beim Abkühlen der Reaktionsflüssigkeit zum Teil aus. Das Bariumsalz besitzt eine geringere Löslichkeit in Wasser.The sodium salt of the ethyl carbamate formed, which is very readily soluble in water the J-acid partially crystallizes out when the reaction liquid cools. The barium salt has a lower solubility in water.
In analoger Weise wird der Carbaminsäureamylester der J-Säure durch Einwirkung von Chlorkohlensäureamylester auf J-Säure erhalten. Das Natriumsalz dieser Verbindung ist schwerer löslich in Wasser als das des betreffenden Äthylesters; die Lösung gelatiniert leicht.In an analogous manner, the amyl carbamate of the J-acid is obtained by the action of Obtained amyl chlorocarbonate on J-acid. The sodium salt of this compound is less soluble in water than that of the ethyl ester concerned; the solution gelatinizes easy.
Der analog durch Einwirkung von ChIorkohlensäurebenzylester auf J-Säure erhaltene Benzylester bildet ein in Wasser leicht lösliches Natriumsalz; dagegen ist das Natrium-The analogue by the action of chlorocarbonic acid benzyl ester Benzyl ester obtained on I-acid forms a readily soluble in water Sodium salt; on the other hand, the sodium
salz des Carbaminsäure-p-nitrobenzylesters der J-Säure in Wasser ziemlich schwer löslich.Salt of the carbamic acid p-nitrobenzyl ester of I-acid rather sparingly soluble in water.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221967C true DE221967C (en) |
Family
ID=482902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT221967D Active DE221967C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221967C (en) |
-
0
- DE DENDAT221967D patent/DE221967C/de active Active
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