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Soap‐based detergent formulations: XVII. Synthesis and surface active properties of alkylbenzene derived amine oxides
Author(s) -
Marmer W. N.,
Linfield W. M.
Publication year - 1976
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02637396
Subject(s) - anhydrous , amine gas treating , chemistry , aqueous solution , sodium silicate , alkyl , alkylation , nuclear chemistry , organic chemistry , materials science , catalysis , composite material
Amine oxides C n H 2n+1 C 6 H 4 SO 2 NH(CH 2 ) 3 ‐NMe 2 —O − were prepared for testing as lime soap dispersing agents in phosphate free, soap‐based, sodium silicate built laundry detergents. These amine oxides were synthesized via a three step route from a variety of pure 1‐phenylalkanes and also from a commerical detergent alkylate mixture. The process included (a) the sulfonation of the phenylalkane with chlorosulfonic acid, (b) reaction of the resulting alkarylsulfonyl chloride with H 2 N(CH 2 ) 3 NMe 2 or with H 2 N(CH 2 ) 3 N(CH 2 CH 2 OH) 2 under anhydrous conditions, and (c) oxidation with aqueous H 2 O 2 . The amine oxides were water soluble and in some instances isolable as crystalline hydrates. They were found to be thermally stable below 125 C and highly surface active. Optimum detergency and lime soap dispersability were achieved by the model compound of alkyl chain length n=8. This was in contrast to the behavior of the related amphoteric sulfobetaine series C n H 2n+1 C 6 H 4 SO 2 NH(CH 2 ) 3 NMe 2 (CH 2 ) 3 ‐SO 3 − , whose optimum detergency and lime soap dispersability previously had been observed to reach a maximum at chain length n=12. Detergency screening tests showed that soap‐based detergents formulated with the sulfobetaines outperformed the ones formulated with the amine oxides.