CS270876B1

CS270876B1 - Method of 1-bromododecane preparation

Info

Publication number: CS270876B1
Application number: CS888354A
Authority: CS
Inventors: Dusan Ing Csc Berkes; Roman Ing Kacina; Juraj Ing Gomory; Maria Ing Frankova; Jozef Ing Niznansky
Original assignee: Dusan Ing Csc Berkes; Kacina Roman; Gomory Juraj; Maria Ing Frankova; Niznansky Jozef
Priority date: 1988-12-16
Filing date: 1988-12-16
Publication date: 1990-08-14
Also published as: CS835488A1

Abstract

The method of 1-bromdecane preparation by the reaction of 1-dodecane with hydrobromic acid in the presence of NaBr and/or KBr an ajacine as an interfacial catalyst with the aim to prepare ajacine from 1-bromodecane and benzyl-dimethyl-amine. The compound prepared is an intermediate product within the production of disinfecting solutions.

Description

(57) Spósob přípravy 1-brómdodekánu reakciou 1-dodekanolu s kyselinou bromovodíkovou v přítomnosti NaBr alebo KBr a ajatínu ako medzifázového katalyzátora, s cielom přípravy ajatínu z 1-brómdodekánu a benzyldimetylamínu. Připravovaná zlúčenina je medziprodukt při výrobě dezinfekčných roztokov.(57) A process for preparing 1-bromododecane by reacting 1-dodecanol with hydrobromic acid in the presence of NaBr or KBr and ajatin as an interfacial catalyst to prepare ajatin from 1-bromododecane and benzyldimethylamine. The compound is an intermediate in the manufacture of disinfectant solutions.

CS 270876 01CS 270876 01

CS 270 876 01CS 270 876 02

Vynález sa týká spósobu přípravy 1-brómdodekánu, medziproduktu při syntéze benzyldodedyldimetylamónium bromidu (ajatínu), ktorý je komponentom dezinfekčných roztokov. Při syntéze sa vychádza z 1-dodekanolu a vodného roztoku HBr za podmienok medzifázovéj katalýzy, pričom ako medzifázový katalyzátor sa využívá samotný ajatín.The invention relates to a process for the preparation of 1-bromododecane, an intermediate in the synthesis of benzyldodedyldimethylammonium bromide (ajatin), which is a component of disinfectant solutions. The synthesis starts from 1-dodecanol and an aqueous solution of HBr under interfacial catalysis conditions using ajatin alone as the interfacial catalyst.

Doteraz sa 1-brómdodekán připravuje z 1-dodekanolu reakciou s bromom a fosforom (Houben-Weyl 5/4, 404 (1960), resp. s NaBr a H₂S0₄ (Rom. R0 76, 601). Óaíšie postupy využívajú medzifázovú katalýzu, kde sa ako katalyzátory požívajú stearylpyridínium bromid (Japan Kokai 78 15, 303) tributylhexadecylfosfónium bromid (CH 589 015 resp. Synthesis 1974, 37). Nedostatkom při použití brómu je vysoká agresivita reakčného prostredia a obtiažna manipulácia, v systéme NaBr + H₂S0₄ nízká konverzia a při použití medzifázovej katalýzy potřeba odstránenia medzifázových katályzátorov z 1-brómdodekánu, keďže ve finál* nom produkte - ajatíne predstavujú nečistoty.To date, 1-bromododecane is prepared from 1-dodecanol by reaction with bromine and phosphorus (Houben-Weyl 5/4, 404 (1960), respectively with NaBr and H ₂ SO ₄ (Rom. R 76, 601). catalysis, wherein as the catalyst enjoy stearylpyridínium bromide (Japan Kokai 78 15, 303) tributylhexadecylphosphonium bromide (CH 589 015 respectively. Synthesis 1974, 37). the disadvantage of the use of bromine is very aggressive reaction medium and difficult to handle, the system NaBr + H ₂ S0 ₄ and the low conversion using the inter-phase catalysis, the need to remove the catalyst from the interfacial 1-brómdodekánu, whereas in the final product * nom - Ajatin are impurities.

Claims

To date, 1-bromododecane is prepared from 1-dodecanol by reaction with bromine and phosphorus (Houben-Weyl 5/4, 404 (1960), respectively with NaBr and H ₂ SO ₄ (Rom. R 76, 601). catalysis, wherein as the catalyst enjoy stearylpyridínium bromide (Japan Kokai 78 15, 303) tributylhexadecylphosphonium bromide (CH 589 015 respectively. Synthesis 1974, 37). the disadvantage of the use of bromine is very aggressive reaction medium and difficult to handle, the system NaBr + H ₂ S0 ₄ and the low conversion using the inter-phase catalysis, the need to remove the catalyst from the interfacial 1-brómdodekánu, whereas in the final product * nom - Ajatin are impurities.

The above disadvantages are overcome by the process for preparing 1-bromododecane according to the invention.

The present invention is based on the reaction of 1-dodecanol with hydrobromic acid in the presence of NaBr or KBr, using ajatin as an interfacial catalyst. The prepared 1-bromododecane containing the interfacial catalyst is used in reaction with benzyldimethylamine to prepare ajatin alone, the aqueous layer containing unreacted hydrobromic acid being used for the next reaction to prepare 1-bromododecane. In the following, the process of the invention is illustrated, but not limited by the following examples:

Example 1

A flask equipped with a stirrer, a condenser and a thermometer was charged with 100 g (0.54 mol) of 1-dodecanol, 11 g (0.023 mol) of ajatin and 12.8 g (0.11 mol) of KBr. The mixture is heated to 80-100 ° C and 272 g (1.61 mol) of 48% hydrobromic acid are added. The reaction mixture was stirred at 118-120 ° C for 3 hours while removing the reaction water (40-50 mL). After cooling, the organic layer is separated from the aqueous layer containing HBr and KBr. The product was shaken with a solution of soda and water (10 g Na ₂ CO 3 j 100 mL H ₂ O). The reaction yield is 128 g (96%) of theory containing 1-bromododecane in the range of 97-99.4 [deg.] (Gas chromatography analysis).

Example 2

To the flask equipped with stirrer, condenser and thermometer was charged an aqueous layer containing HBr-KBr from Example 1. 100 g (0.54 mol) of 1-dodecanol and 89 g (0.53 mol) of 48 4 HBr were added and the reaction mixture was heated to 120 ° C. 3 hours The mixture was stirred at 118-120 ° C while water (40-50 ml) was distilled off. After cooling, the product is worked up as in Example 1. The yield of the reaction is 127 to 129 g i.e. 95 to 96% of theory with 1-bromododecane content of 97 to 99%.

OBJECT OF THE INVENTION