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Synthesis and in situ transformation of poly(oxybutylene)amides by butoxylation
Author(s) -
Lin JiangJen,
Wu JengJaw,
Ho YungSheng
Publication year - 2001
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1869
Subject(s) - amide , chemistry , polymer chemistry , titration , steric effects , hydrolysis , fourier transform infrared spectroscopy , amine gas treating , organic chemistry , chemical engineering , engineering
A family of gasoline detergents was prepared by a two‐step process—(1) preparation of amide initiators by reacting hydrophilic amines with ethyl acetate at high temperature; (2) consecutive butoxylation of the initiators with 1,2‐epoxybutane (BO) to obtain oil‐soluble products. The process led to the preparation of amide‐initiated butoxylates, which were characterized by FTIR, NMR, and amine titration. During the butoxylation, it was found that the unexpected ester by‐products were generated via an amide/ester exchange. The reaction profile was studied. The amide/ester exchange reaction, characterized by IR absorption of amide (1650 cm −1 ) vs. ester (1735 cm −1 ), reached equilibrium during the process of butoxylation to 1600 M w . Steric hindrance of the amide structures is an important factor controlling the formation of these ester byproducts. Selective hydrolysis to remove the ester by‐products is necessary to render the final product with an improved engine performance of octane requirement. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 435–445, 2001