DE529538C - Process for the preparation of aromatic nitro compounds - Google Patents
Process for the preparation of aromatic nitro compoundsInfo
- Publication number
- DE529538C DE529538C DE1930529538D DE529538DD DE529538C DE 529538 C DE529538 C DE 529538C DE 1930529538 D DE1930529538 D DE 1930529538D DE 529538D D DE529538D D DE 529538DD DE 529538 C DE529538 C DE 529538C
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen fluoride
- nitro compounds
- aromatic nitro
- preparation
- parts
- 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
- 238000000034 method Methods 0.000 title claims description 5
- -1 aromatic nitro compounds Chemical class 0.000 title claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 10
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000004323 potassium nitrate Substances 0.000 description 2
- 235000010333 potassium nitrate Nutrition 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- RIDYGARTUIQVAD-UHFFFAOYSA-N potassium sulfuric acid nitrate Chemical compound [K+].[O-][N+]([O-])=O.OS(O)(=O)=O RIDYGARTUIQVAD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000725 suspension Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung aromatischer Nitroverbindungen Es ist bekannt, daß man aromatische Verbindungen durch verdünnte und konzentrierte Salpetersäure, durch Salpeterschwefelsäure, durch Schwefelsäurekaliumnitrat usw. nitrieren kann. Dabei ist es in den meisten Fällen unbedingt erforderlich, bestimmte Temperaturgrenzen einzuhalten, da sonst die Reaktionen zu stürmisch verlaufen und zu unerwünschten Nebenprodukten führen. In einigen Fällen lassen auch die Ausbeuten zu wünschen übrig.Process for the production of aromatic nitro compounds It is known that aromatic compounds can be obtained by dilute and concentrated nitric acid, can nitrate by nitric sulfuric acid, by sulfuric acid potassium nitrate, etc. In most cases it is absolutely necessary to set certain temperature limits to be observed, otherwise the reactions will be too stormy and undesirable Lead by-products. In some cases, the yields also leave something to be desired.
Es wurde nun. gefunden, daß manNitrierungen in einfacher und bequemer Weise durchführen kann, indem man die Nitrierung in wasserfreiem oder hochkonzentriertem Fluorwasserstoff als Lösungs- oder Suspensionsmittel vornimmt. Als Nitriermittel kann man z. B. wasserfreie Salpetersäure, Kaliumnitrat, Calciumnitrat oder andere Nitrate verwenden. Die Einwirkung erfolgt - zweckmäßig unter Kühlung - ohne Stickoxyd'entwicklung in sehr milder Form, wobei auch die Ausbeuten in sehr vielen Fällen die nach en üblichen Verfahren übertreffen. Derartig stürmische Steigerungen des Reaktionsverlaufs mit der Temperatur wie bei den bisherigen Nitrierungsverfahren treten bei den Nitrierungen in Fluorwasserstoff nicht auf. Es ist jedoch zweckmäßig, die Temperatur relativ niedrig, auf etwa o° oder darunter, zu halten, damit der durch Verdampfen eintretende Verlust an Fluorwasserstof möglichst gering wird. Der Fluorwasserstoff läßt sich im übrigen weitgehendst zurückgewinnen. Beispiel i Zu einer Suspension von 6,7 Gewichtsteilen Benzol in io Gewichtsteilen Fluorwasserstoff fügt man bei Zimmertemperatur oder besser bei o° eine Lösung von 12 Gewichtsteilen Kaliumnitrat in 3o Gewichtsteilen Fluorwasserstoff nach und nach portionsweise hinzu. Nach beendeter Reaktion wird der Fluorwasserstoff durch Luft oder indifferente Gase abgeblasen. Den Rückstand wäscht man mehrere Male mit Wasser, neutralisiert schließlich mit Soda oder Lauge und destilliert im Wasserdampfstrom. Es entsteht ausschließlich Mononitrobenzol in quantitativer Ausbeute. Beispiel e Zu einer Lösung von 9,2 Gewichtsteilen Phenol in io Gewichtsteilen Fluorwasserstoff fügt man eine Lösung von 12 Gewichtsteilen Kaliumnitrat in 3o Gewichtsteilen Fluorwasserstaff bei o° portionsweise hinzu. Nach längerem Stehen wird .der F luorwasserstoff durch Erwärmen und Durchleiten von Luft weitgehend entfernt. Der Rückstand wird mit Wasser zweimal dekantiert und nach Hinzufügen von genügend Natriumacetat das o-Nitrophenol mit Wasserdampf übergetrieben. Ausbeute 3,a Gewichtsteile. Der Rückstand der Wasserdampf destllation wird stark alkalisch gemacht, filtriert und durch Eindampfen eingeengt. Das filtrierte und abgepreßte Natriumsalz .des p-Nitrophenols wird in wenig Wasser gelöst und durch Zusatz von konzentrierter Salzsäure das p-Nitrophenol ausgefällt. Ausbeute 5 Gewichtsteile.. Eine-Verharzung ist nicht zu beobachten.It was now. found that it was easier and more convenient to carry out nitriding Way can be carried out by getting the nitration in anhydrous or highly concentrated Carries out hydrogen fluoride as a solvent or suspending agent. As a nitrating agent you can z. B. anhydrous nitric acid, potassium nitrate, calcium nitrate or others Use nitrates. The action takes place - expediently with cooling - without the development of nitrogen oxide in a very mild form, the yields in very many cases also being those according to en exceed usual procedures. Such stormy increases in the course of the reaction with the temperature as in the previous nitration processes occur in the nitrations does not occur in hydrogen fluoride. However, it is advisable to keep the temperature relative low, at about 0 ° or below, so that the evaporation occurs Loss of hydrogen fluoride is as low as possible. The hydrogen fluoride can otherwise largely recover. Example i To a suspension of 6.7 parts by weight Benzene in 10 parts by weight of hydrogen fluoride is added at room temperature or better at 0 ° a solution of 12 parts by weight of potassium nitrate in 3o parts by weight Gradually add hydrogen fluoride in portions. When the reaction is complete, the hydrogen fluoride is blown off by air or inert gases. The residue washed several times with water, then neutralized with soda or lye and distilled in a stream of steam. Only mononitrobenzene is produced in quantitative yield. Example e To a solution of 9.2 parts by weight of phenol a solution of 12 parts by weight is added in 10 parts by weight of hydrogen fluoride Potassium nitrate in 3o parts by weight of hydrogen fluoride is added in portions at 0 °. To After standing for a long time, the hydrogen fluoride is converted by heating and passing air through largely removed. The residue is decanted twice with water and after adding of enough sodium acetate that o-Nitrophenol driven over with steam. Yield 3, a parts by weight. The residue of the steam distillation becomes strong made alkaline, filtered and concentrated by evaporation. That filtered and squeezed out sodium salt .des p-nitrophenol is dissolved in a little water and washed through Addition of concentrated hydrochloric acid precipitates the p-nitrophenol. Yield 5 parts by weight. No gumming can be observed.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE529538T | 1930-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE529538C true DE529538C (en) | 1931-07-15 |
Family
ID=6554112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930529538D Expired DE529538C (en) | 1930-08-02 | 1930-08-02 | Process for the preparation of aromatic nitro compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE529538C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0251953A1 (en) * | 1986-07-04 | 1988-01-07 | Rhone-Poulenc Chimie | Process for the preparation of dinitroalkyl benzenes |
-
1930
- 1930-08-02 DE DE1930529538D patent/DE529538C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0251953A1 (en) * | 1986-07-04 | 1988-01-07 | Rhone-Poulenc Chimie | Process for the preparation of dinitroalkyl benzenes |
| FR2601003A1 (en) * | 1986-07-04 | 1988-01-08 | Rhone Poulenc Chim Base | PROCESS FOR THE PREPARATION OF DINITROALKYLBENZENES |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE529538C (en) | Process for the preparation of aromatic nitro compounds | |
| DE2131561B2 (en) | Process for the preparation of 3,5-dinitrobenzotrifluorides | |
| DE2508247A1 (en) | METHOD FOR MANUFACTURING CYCLOHEXANONOXIME | |
| DE1002309B (en) | Process for the production of glyoxylic acid | |
| DE372842C (en) | Process for the preparation of amidines | |
| DE932793C (en) | Process for the preparation of aromatic nitrocarbonyl compounds | |
| DE877303C (en) | Process for the preparation of oximes | |
| DE510432C (en) | Process for the preparation of aminopyridine compounds | |
| DE558468C (en) | Process for the production of ª ‡ -nitronaphthalene | |
| DE900341C (en) | Process for the continuous production of nitroform | |
| DE1210880B (en) | Process for the preparation of 2,4-dinitro-6-chloromethylphenol | |
| DE966201C (en) | Process for the preparation of cyclohexanone oxime by catalytic hydrogenation of nitrocyclohexane salts | |
| DE535049C (en) | Process for the preparation of oxyalkylamines | |
| DE924241C (en) | Process for the production of cyanuric acid decoctions | |
| DE512639C (en) | Production of concentrated nitric acid | |
| CH282274A (en) | Process for the preparation of 2,9-dimethyl-1,10-phenanthroline. | |
| DE805400C (en) | Process for the production of dinitrophenyl ethers | |
| DE602999C (en) | Process for the production of formic acid by reacting sodium formate with nitric acid | |
| DE528113C (en) | Process for the preparation of pyridinarsic acids | |
| DE635185C (en) | Process for the preparation of symmetrical hexanitrodiphenyloxide | |
| DE723497C (en) | Process for the preparation of ethylpentaerythritol trinitrate | |
| AT132717B (en) | Process for the preparation of formic acid from formates. | |
| DE453429C (en) | Process for the production of nitrophenol alkyl ethers | |
| DE851188C (en) | Process for the preparation of dicyclohexylamine | |
| DE562821C (en) | Process for the simultaneous production of ammonium salt and alcohols |