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Phase transfer catalysts as co‐catalysts in the ethoxylation of nonyl phenol
Author(s) -
Wesslén Bengt,
Andreasson Eva,
Holmberg Krister
Publication year - 1989
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/bf02670094
Subject(s) - catalysis , chemistry , ethylene oxide , phenol , alkali metal , protonation , ethylene , inorganic chemistry , ether , crown ether , polymer chemistry , organic chemistry , ion , copolymer , polymer
Ethoxylation of nonyl phenol has been carried out at 130°C and at an absolute pressure of two bars. Alkali metal hydroxides were used as catalysts, either neat or in conjunction with added co‐catalysts such as 18‐crown‐6 and tetramethyl ethylene diamine (TMEDA). The overall reaction rates were found to increase fivefold on the addition of the co‐catalysts. The use of TMEDA as the sole catalyst gave equally high reaction rates. This fact can be explained by the high basicity of TMEDA and by the formation of a highly reactive ion pair similar to those found in phase transfer catalysis. The differences in the kinetics of the reactions were analysed by computer simulation, using a five parameter model. According to this model, the crown ether‐catalyzed ethoxylation of nonyl phenol was found to proceed via protonated ethylene oxide, while pure alkali catalysis proceeded mainly via uncomplexed ethylene oxide. Small differences in the oligomer distributions were noted.