CS270521B1

CS270521B1 - Method of 3-methyl-4-nitrosophenol production

Info

Publication number: CS270521B1
Application number: CS881210A
Authority: CS
Inventors: Peter Ing Hauskrecht; Ivan Ing Zervan; Henrich Kovacic; Juraj Lacko
Original assignee: Hauskrecht Peter; Ivan Ing Zervan; Henrich Kovacic; Juraj Lacko
Priority date: 1988-02-25
Filing date: 1988-02-25
Publication date: 1990-07-12
Also published as: CS121088A1

Abstract

3-metyl-4r-nitrózofenol sa vyrába nitrozáciou 3-metylCenolu s dusitanom sodným. v prostředí minerálně;) kyseliny v přítomnosti tenzidu.3-Methyl-4-nitrosophenol is produced by nitrosation 3-methyl-phenol with sodium nitrite. in the mineral; acid in the presence surfactant.

Description

Vynález sa týká sposobu výroby 3-metyl-4-nitrózofenolu nitrozáciou 3-metylfenolu s roztokou dusitanu sodného v prostředí, minerálnej kyseliny v přítomnosti tenzidu 3-metyl-4-nitrózofenol sa najčaetejšie používá ako medziprodukt při výrobě nitroderivátov 3-metylfenolu. Výrobu 3-metyl-4-nitrózofenolu popisuje Bridge Morgan, J. Am, Chem. Soc. 20 766 (1898) nitrozáciou 3-metylfenolu s kyselinou dusitou. Nitrozácia 3-metylfenolu s alkalickým dusitanem v prostředí kyseliny sírovej popisuje USA pat. δ. 1 502 849. Rozpustnosti 3-metylfenolu vo vodných roztokoch minerálnej kyseliny s minerálnymi solami je malá a z toho dSvodu reakcia prebieha prakticky na rozhraní kvapalnej páry organickej vrstvy a vodných roztokpv. 3-metyl-4-nitrózofenol je velmi málo rozpustný v reakčnej zmesi. V priemyselnom měřítku sa často stává, že dochádza k tvorbo inkrustov na stěnách reaktora, miešadlách a pod., pričom časti 3-metylfenolu zostáva nezreagovaná a samotná inkrusty znižujú přestup tepla cez stenu reaktora, pričom mČže dochádzat k lokálnemu prehriatiu reakčnej zmesi.The invention relates to a process for the preparation of 3-methyl-4-nitrosophenol by nitrosation of 3-methylphenol with a solution of sodium nitrite in a medium, a mineral acid in the presence of a surfactant. The preparation of 3-methyl-4-nitrosophenol is described by Bridge Morgan, J. Am, Chem. Soc. 20,766 (1898) by nitrosation of 3-methylphenol with nitrous acid. The nitrosation of 3-methylphenol with alkali nitrite in a sulfuric acid medium is described in U.S. Pat. δ. 1,502,849. The solubility of 3-methylphenol in aqueous solutions of mineral acid with mineral salts is small and therefore the reaction takes place practically at the interface of the liquid vapor of the organic layer and the aqueous solutions. 3-methyl-4-nitrosophenol is very slightly soluble in the reaction mixture. On an industrial scale, it often happens that incrustations form on the reactor walls, stirrers, etc., while parts of 3-methylphenol remain unreacted and the incrustations themselves reduce heat transfer through the reactor wall, whereby local overheating of the reaction mixture can occur.

Vyššie uvedené nedostatky sú zmiernené spSsobom výroby 3-metyl-4-nitrózofenolu, podstata ktorého spočívá v tom, že 3-metylfenol sa nitrozuje s vodným roztokom dusitanu sodného v přítomnosti minerálnej kyseliny, najčastejšie kyseliny sírovéj alebo chlorovodíkovéj. Nitrozácia prebieha v přítomnosti tenzidu.The above drawbacks are alleviated by the process for the preparation of 3-methyl-4-nitrosophenol, which consists in nitrosating 3-methylphenol with an aqueous solution of sodium nitrite in the presence of a mineral acid, most often sulfuric or hydrochloric acid. Nitrosation takes place in the presence of a surfactant.

Výhodou postupu podlá vynálezu je, že pri výrobě 3-metyl-4-nitrózofenolu sa netvoria inkrusty na stěnách reakčnej aparatuře, ktoré zhoršovali přestup tepla, čím mohlo nastat miestne prehriatie. Po ukončení výroby 3-metyl-4-nitrňzofenolu sa museli inkrusty odstránit, čo. bolo podstatné a ap8Bobovalo časové a materiálně stráty. Tenzid zabezpečuje lepší styk organickej i anorganickej časti kvapalnej fázy a reakcia m3 že prebiehať čiastočne v emulzii, ktorá umožňuje váčSiu reakčnú rýchlost ako i lepší odvod tepla. ’An advantage of the process according to the invention is that in the production of 3-methyl-4-nitrosophenol no incrustations are formed on the walls of the reaction apparatus which impair the heat transfer, which could lead to local overheating. After the production of 3-methyl-4-nitrosophenol was stopped, the incrustations had to be removed, which. it was substantial and ap8Bobobed time and material losses. The surfactant ensures better contact of the organic and inorganic parts of the liquid phase and the reaction can take place partly in an emulsion, which allows a higher reaction rate as well as better heat dissipation. ’

Příklad 1Example 1

Do reakčnej banky sa dalo 340 g 60,3 % hmot, kyseliny sírovéj a 35 g 3-metylfenolu a 2 mg etylenoxidovaný adukt kyseliny nanoolejovej s počtom etylenoxidových jednotiek 19 až 24 (Slovasol-BL). Zmes sa za miešania ochladila na 0 °C. Potom sa . k zmesi přidávalo počas 90 minut 70 g 38 % hmot, vodného roztoku NaNOg. Po ukončení premývania sa suspenzia odfiltrovala a premyla a 100 ml vody. Piltračný koláč o hmotnosti 44,3 g obsahoval 99 % hmot. 3-metyl-4-nitrózofenolu.340 g of 60.3% by weight of sulfuric acid and 35 g of 3-methylphenol and 2 mg of an ethylene-oxidized adduct of nano-oleic acid with a number of ethylene oxide units of 19 to 24 (Slovasol-BL) were added to the reaction flask. The mixture was cooled to 0 ° C with stirring. Then. 70 g of a 38% strength by weight aqueous NaNOg solution were added to the mixture over a period of 90 minutes. After washing, the suspension was filtered and washed with 100 ml of water. The 44.3 g filter cake contained 99% by weight. 3-methyl-4-nitrosophenol.

Příklad 2 .Example 2.

Do reakčného kotlá sa dalo 1 220 1 60-,3 % hmot, kyeeliny sírovéj, ktorá sa vychladila na 5 °C. Potom sa k roztoku HgSO^ přidalo 183 1 3-metylfenolu a 0,02 1 20 % hmot, vodného roztoku dodecylbenzénsulfonanu sodného (Abeson NAM). Potom se po ochladení na 0 °C začalo dávkovat za miešania pod hladinu 300 1 38 % hmot, vodného roztoku dusitanu sodného, pričom teplota nepresiahla 5 °C. Doba dávkovania bola 160 min. Reakčná zmes sa miešala ešte 30 minút. Získaná suspenzia obsahovala v přepočítaní 235 kg 100 % hmot 3-metyl-4-nitrózofenolu.1,220 L of 60.3% by weight of sulfuric acid was charged to the reaction vessel and cooled to 5 ° C. Then 183 L of 3-methylphenol and 0.02 L of a 20% w / w aqueous solution of sodium dodecylbenzenesulfonate (Abeson NAM) were added to the HgSO 4 solution. Then, after cooling to 0 [deg.] C., 38 l of a 38% strength by weight aqueous sodium nitrite solution were started to be metered in with stirring below the level of 300 l, the temperature not exceeding 5 [deg.] C. The dosing time was 160 min. The reaction mixture was stirred for another 30 minutes. The suspension obtained contained 235 kg of 100% by weight of 3-methyl-4-nitrosophenol.

Vynález sa uplatní pri výrobě 3-metyl-4-nitrózofenolu, ktorý je medziprodukt pri výrobě viacerých organických látok, například 0,0-dimetyl-0-/3~metyl-4-nitrofenyl/tiofosfátu.The invention is useful in the preparation of 3-methyl-4-nitrophenol, which is an intermediate in the production of several organic substances, for example 0,0-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate.

Claims

OBJECT OF THE INVENTION

Process for the preparation of 3-methyl-4-nitrosophenol by nitrosation of 3-methylphenol with an aqueous solution of sodium nitrite in a mineral acid medium, characterized in that the nitrosation is carried out in the presence of a surfactant.