DE211959C - - Google Patents
Info
- Publication number
- DE211959C DE211959C DENDAT211959D DE211959DA DE211959C DE 211959 C DE211959 C DE 211959C DE NDAT211959 D DENDAT211959 D DE NDAT211959D DE 211959D A DE211959D A DE 211959DA DE 211959 C DE211959 C DE 211959C
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acids
- aldehydes
- acid
- hypochlorite
- nitrobenzaldehyde
- 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
- WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 10
- 230000000875 corresponding Effects 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 3
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NPDODHDPVPPRDJ-UHFFFAOYSA-N permanganate Chemical compound [O-][Mn](=O)(=O)=O NPDODHDPVPPRDJ-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KIHAMCBHCNQCST-UHFFFAOYSA-N 2-formyl-5-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C=O KIHAMCBHCNQCST-UHFFFAOYSA-N 0.000 description 1
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 1
- VWLGQKLHWIVCCZ-UHFFFAOYSA-N 53992-33-9 Chemical compound OS(=O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 VWLGQKLHWIVCCZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 211959 KLASSE 12 o. GRUPPE- M 211959 CLASS 12 or GROUP
BADISCHE ANILIN- & SODA-FABRIK in LUDWIGSHAFEN a. Rh.BADISCHE ANILINE & SODA FACTORY in LUDWIGSHAFEN a. Rh.
aus den entsprechenden Aldehyden.from the corresponding aldehydes.
Patentiert im Deutschen Reiche vom 2. August 1908 ab.Patented in the German Empire on August 2, 1908.
Während Benzaldehyd sowie die entsprechenden Halogensubstitutionsderivate mit größter Leichtigkeit schon durch den Sauerstoff der Luft zu. den entsprechenden Carbonsäuren oxydiert werden, sind die Derivate mit negativen Substituenten —■ z. B. die Nitro- und Sulfobenzaldehyde, Benzaldehydcarbonsäuren usw. — gegen Oxydationsmittel verhältnismäßig beständig. Zur ÜberführungWhile benzaldehyde as well as the corresponding halogen substitution derivatives with the greatest lightness from the oxygen in the air. the corresponding carboxylic acids are oxidized, the derivatives with negative substituents - ■ z. B. the nitro and sulfobenzaldehydes, benzaldehyde carboxylic acids, etc. - relative to oxidizing agents resistant. To the transfer
ίο dieser Aldehyde in die entsprechenden Carbonsäuren sind bisher als Oxydationsmittel Chromsäure, Salpetersäure und Permanganat verwendet worden (vgl. z.B. Beilstein, 3. Auflage, Bd. Ill, S. 16; Berichte 24, 796; Beilstein, Bd. II, S. 1625).ίο these aldehydes into the corresponding carboxylic acids chromic acid, nitric acid and permanganate have so far been used as oxidizing agents (see e.g. Beilstein, 3rd edition, vol. Ill, p. 16; reports 24, 796; Beilstein, Vol. II, p. 1625).
Es wurde nur gefunden, daß obige Aldehyde mit großer Leichtigkeit in vorzüglicher Ausbeute ohne Bildung von Chlorsubstitutionsprodukten in. die entsprechenden Carbonsäuren übergeführt werden, wenn man auf sie Hypochloritlösungen bei Gegenwart von Alkali einwirken läßt. Es ist auf diese Weise möglich, die oben genannten teuren Oxydationsmittel, Chromsäure, Salpetersäure, Permanganat, durch das ganz wesentlich billigere Hypochlorit zu ersetzen und so aromatische Carbonsäuren technisch darzustellen, welche auf anderem Wege bisher nicht in einheitlicher Form zugänglich waren. So z. B. erhält man die m-Nitrobenzoesäure, zu deren Darstellung man bisher auf die Nitrierung der Benzoesäure und die dabei notwendige mühevolle Abtrennung der isomeren Nitroverbindungen angewiesen war, auf dem geschilderten Wege aus dem technisch einheitlich vorhandenen m-Nitrobenzaldehyd in reiner Form.It has only been found that the above aldehydes can be obtained with great ease in excellent yield without the formation of chlorine substitution products in the corresponding carboxylic acids be transferred if you act on them hypochlorite solutions in the presence of alkali leaves. In this way it is possible to use the above-mentioned expensive oxidizing agents, Chromic acid, nitric acid, permanganate, due to the much cheaper hypochlorite replace and so technically represent aromatic carboxylic acids, which on other Paths were previously not accessible in a uniform form. So z. B. you get the m-Nitrobenzoic acid, for the representation of which one has so far relied on the nitration of benzoic acid and instructed the laborious separation of the isomeric nitro compounds which is necessary was, on the route outlined above from the technically uniform m-nitrobenzaldehyde in pure form.
Über die Verwendbarkeit von Hypochloriten als Mittel zur Oxydation solcher Aldehyde zu den entsprechenden Säuren ist bisher nichts bekannt geworden. Man mußte aus den bisherigen Literaturangaben schließen, daß derartige Aldehyde gegen Hypochloritlösungen beständig seien, da z. B. der p-Nitro-o-sulfobenzaldehyd aus p-Nitrotoluolsulfosäure durch Oxydation mit einem großen Überschuß von Natriumhypochloritlösung dargestellt wird (Patentschrift 115410).About the usability of hypochlorites as a means of oxidizing such aldehydes So far nothing has been known about the corresponding acids. You had to get out of the previous ones References conclude that such aldehydes are resistant to hypochlorite solutions, since z. B. p-nitro-o-sulfobenzaldehyde from p-nitrotoluenesulfonic acid by oxidation with a large excess of Sodium hypochlorite solution is represented (patent specification 115410).
Zu 151 Teilen m-Nitrobenzaldehyd wird eine Natriumhypochloritlösung, welche 71 Teile wirksames Chlor und 40 Teile Natronhydrat enthält, langsam unter Umrühren zugefügt. Unter lebhafter Wärmeentwicklung geht der m-Nitrobenzaldehyd in Lösung. Durch zeitweise Kühlung wird dafür Sorge getragen, daß die Reaktion nicht zu heftig verläuft. Nach Beendigung des Eintragens wird noch einige Zeit erwärmt, bis alles Hypochlorit verschwunden ist. Das Natriumsalz der gebildeten m-Nitrobenzoesäure scheidet sich größtenteils beim Erkalten in reiner Form ab und wird abfiltriert. Der Rest der m-Nitrobenzoesäure kann aus dem Filtrat durch Ansäuern gewonnen werden.To 151 parts of m-nitrobenzaldehyde is one Sodium hypochlorite solution, which contains 71 parts of effective chlorine and 40 parts of sodium hydrate contains, added slowly while stirring. The goes under vigorous heat development m-nitrobenzaldehyde in solution. Temporary cooling ensures that the Reaction is not too violent. After completing the entry, there will be a few more Heated time until all hypochlorite is gone. The sodium salt of the formed Most m-nitrobenzoic acid separates out in pure form on cooling and is filtered off. The remainder of the m-nitrobenzoic acid can be removed from the filtrate by acidification be won.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE211959C true DE211959C (en) |
Family
ID=473723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT211959D Active DE211959C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE211959C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220793A (en) * | 1977-11-17 | 1980-09-02 | Labaz | Process for preparing a thiophene derivative |
| FR2495138A1 (en) * | 1980-12-01 | 1982-06-04 | Daicel Chem | PROCESS FOR THE PREPARATION OF GLOXYLIC ACID |
-
0
- DE DENDAT211959D patent/DE211959C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220793A (en) * | 1977-11-17 | 1980-09-02 | Labaz | Process for preparing a thiophene derivative |
| FR2495138A1 (en) * | 1980-12-01 | 1982-06-04 | Daicel Chem | PROCESS FOR THE PREPARATION OF GLOXYLIC ACID |
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