PL124172B2 - Method of separation of p-nitroethylbenzene - Google Patents
Method of separation of p-nitroethylbenzene Download PDFInfo
- Publication number
- PL124172B2 PL124172B2 PL22935681A PL22935681A PL124172B2 PL 124172 B2 PL124172 B2 PL 124172B2 PL 22935681 A PL22935681 A PL 22935681A PL 22935681 A PL22935681 A PL 22935681A PL 124172 B2 PL124172 B2 PL 124172B2
- Authority
- PL
- Poland
- Prior art keywords
- nitroethylbenzene
- separation
- isomers
- mixture
- precipitate
- Prior art date
Links
- RESTWAHJFMZUIZ-UHFFFAOYSA-N 1-ethyl-4-nitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C=C1 RESTWAHJFMZUIZ-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 238000000926 separation method Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 1
- XAWCLWKTUKMCMO-UHFFFAOYSA-N 2-nitroethylbenzene Chemical class [O-][N+](=O)CCC1=CC=CC=C1 XAWCLWKTUKMCMO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Opis patentowy opublikowano: 31.01.1984 Int. Cl.3 C07C 76/06 C07C 79/10 C Z r . l l '* I A U Twórcywynalazku: Tomasz Kozluk, Wojciech Kulicki Uprawniony z patentu tymczasowego: Zaklad Doswiadczalny „CHEMIPAN" Instytut Chemii Fizycznej i Instytutu Chemii Organicznej Polskiej Akademii Nauk, Warszawa (Polska) Sposób wydzielania p-nitroetylobenzenu Przedmiotem wynlalazku jest sposób wydzielania p-nitroetylobenzenu z mieszaniny izome¬ rów o-, m-, p-nitroetylobenzenów. Izomer para jest cennym pólproduktem w przemysle chemi¬ cznym, zwlaszcza w produkcji srodków zapachowych oraz zwiazków o wlasnosciach cieklokrystalicznych.Dotychczas p-nitroetylobenzen otrzymywano przez rozdestylowanie mieszaniny izomerów powstalych w wyniku nitrowania etylobenzenu. Sposób ten wymaga wysoko wydajnych kolumn destylacyjnych ze wzgledu na niewiele rózniace sie temperatury wrzenia poszczególnych izomerów.Proces destylacji jest czasochlonny, a ponadto wymaga specjalnych srodków ostroznosci z uwagi na czeste wypadki eksploatacji wystepujace w czasie destylacji.Celem wynalazku bylo unikniecie tych niedogodnosci i opracowanie bezpiecznego sposobu otrzymywania p-nitroetylobenzenu z mieszaniny izomerów, otrzymanej po nitrowaniu etylobenzenu.Stwierdzono, ze cel ten uzyskuje sie, jezeli mieszanine izomerów nitroetylobenzenu w roztwo¬ rze rozpuszczalnika typu benzen, weglowodorów nasyconych, alkoholi, estrów lub mieszanin takich rozpuszczalników oziebia sie ponizej temperatury —40°C,po czym wytracony osad oddziela sie. Osad ten stanowi p-nitroetylobenzen o czystosci przekraczajacej 98%.Sposób wedlug wynalazku odznacza sie prostota, oraz wysokim stopniem bezpieczenstwa.Wielokrotne powtórzenie procesu wedlug wynalazku pozwala uzyskac produkt o bardzo wysokiej czystosci, zawierajacy 99,5% p-nitroetylobenzenu.Przy klad I. Do 200 g mieszaniny nitroetylobenzenów o skladzie 25% orto, 3% meta, 72% para, dodano 3 dcm3 ligroiny (frakcja wrzaca w temperaturze 68-80°C) i ochlodzono do tempera¬ tury —60°. Wytracone krysztaly odsacza sie, przemywa ligroina, a nastepnie w temperaturze pokojowej odparowuje sie rozpuszczalnik pod zmniejszonym cisnieniem i otrzymuje 163 g pro¬ duktu o zawartosci p-nitroetylobenzenu 98,8%, a izomeru orto i meta po 0,6%.2 124172 PLThe patent description was published: 01/31/1984 Int. Cl. 3 C07C 76/06 C07C 79/10 C Z r. ll '* IAU Inventors: Tomasz Kozluk, Wojciech Kulicki Authorized by the provisional patent: "CHEMIPAN" Experimental Plant Institute of Physical Chemistry and Institute of Organic Chemistry of the Polish Academy of Sciences, Warsaw (Poland) Method of p-nitroethylbenzene separation The subject of the invention is the method of separating p-nitroethylbenzene from mixtures of isomers of o-, m-, p-nitroethylbenzenes. The vapor isomer is a valuable intermediate in the chemical industry, especially in the production of fragrances and compounds with liquid crystalline properties. This process requires highly efficient distillation columns due to the slightly different boiling points of the individual isomers. The distillation process is time-consuming and also requires special precautions due to frequent operating accidents occurring during distillation. The aim of the invention was to avoid you. the disadvantages and the development of a safe method of obtaining p-nitroethylbenzene from the mixture of isomers obtained after the nitration of ethylbenzene. It has been found that this goal is achieved if a mixture of nitroethylbenzene isomers in a solvent of benzene type, saturated hydrocarbons, alcohols, esters or mixtures of such solvents is cooled temperature below -40 ° C, then the precipitate is separated. This precipitate is p-nitroethylbenzene with a purity exceeding 98%. The method according to the invention is characterized by simplicity and a high degree of safety. Repeating the process according to the invention many times allows to obtain a product of very high purity, containing 99.5% p-nitroethylbenzene. Clade I. To 200 g of a mixture of nitroethylbenzenes consisting of 25% ortho, 3% meta, 72% steam, 3 dcm 3 of ligroin (fraction boiling at 68-80 ° C.) was added and cooled to -60 °. The precipitated crystals are filtered off, washed with ligroin, and then the solvent is evaporated at room temperature under reduced pressure, yielding 163 g of the product with 98.8% p-nitroethylbenzene and 0.6% of the ortho and meta isomer.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL22935681A PL124172B2 (en) | 1981-01-23 | 1981-01-23 | Method of separation of p-nitroethylbenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL22935681A PL124172B2 (en) | 1981-01-23 | 1981-01-23 | Method of separation of p-nitroethylbenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL229356A2 PL229356A2 (en) | 1981-11-27 |
| PL124172B2 true PL124172B2 (en) | 1982-12-31 |
Family
ID=20007107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL22935681A PL124172B2 (en) | 1981-01-23 | 1981-01-23 | Method of separation of p-nitroethylbenzene |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL124172B2 (en) |
-
1981
- 1981-01-23 PL PL22935681A patent/PL124172B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL229356A2 (en) | 1981-11-27 |
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