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Investigated on the Rubber Antioxidant 2,2,4-Trimethyl-1,2-dihydroquinoline Polymer
Corresponding Author(s) : Yu Liu
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
The paper investigated the mechanism of the reaction which are used in synthesis of 2,2,4-trimethyl-1,2-dihydroquinoline and 2,2,4-trimethyl-1,2-dihydroquinoline polymer. Aromatic amines and a-alkenyl alkyl ether condensation of synthetic quinoline and polymerization. one is acetone, aniline on direct condensation to form Schiff base and then further reduced synthesis loop; the other is the first for two molecules of acetone condensation to form iso-propylidene acetone and then iso-propylidene acetone condense with aniline ring. Aniline and acryladehyde will not form Schiff base in acid and directed formed quinoline. Acetone molecules to produce diacetone alcohol, diacetone alcohol shrink generated iso-propylidene acetone. In acidic conditions, iso-propylidene acetone oxygen atoms combine to form hydroxyl and hydrogen ions to form positively charged enol structure. Others aniline and acetone, carried out the nucleophilic addition reaction of N-isopropyl aniline fork. Two molecules of N-isopropyl fork intermediates after addition of aniline, cyclization under acidic conditions, off part of aniline to produce a monomer of 2,2,4-trimethyl-1,2-dihydroquinoline.
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- C.A. Migdal and R.D. Abbott, Lubricant Compositions Comprising Multiple Antioxidants, US Patent 6,726,855 B1 (2004).
- T. Kojima, E. Okino and R. Ishimoto, Manufacture of Polymerized 2,2,4-Trimethyl-1,2-dihydroquinoline, US Patent 4,326,062 (1982).
- B.F. Goodrich Company, Improvements in or Relating to Aniline Condensation Products and Process of Preparing Same, GB Patent 620314, (1949).
- B.F. Goodrich Company, Preparation of Monomeric 2,2,4-Trimethyl1,2-di-hydroquinoline, US Patent 2514648 (1950).
- Institute Organicheskoi Khimii lmeni N.D. Zelinskogo An SSSR, Process for the Production of Substituted 1,2-Dihydroquinolines, GB Patent 1256725 (1971).
- Process for the Production of Substituted 1,2-Dihydroquinolines, US Patent 38994932 (1975).
- H.M. Rivera, Novel Apparatus for the Obtention of Substituted 1,2- Dihydroquinolines, US Patent 3829292 (1974).
References
C.A. Migdal and R.D. Abbott, Lubricant Compositions Comprising Multiple Antioxidants, US Patent 6,726,855 B1 (2004).
T. Kojima, E. Okino and R. Ishimoto, Manufacture of Polymerized 2,2,4-Trimethyl-1,2-dihydroquinoline, US Patent 4,326,062 (1982).
B.F. Goodrich Company, Improvements in or Relating to Aniline Condensation Products and Process of Preparing Same, GB Patent 620314, (1949).
B.F. Goodrich Company, Preparation of Monomeric 2,2,4-Trimethyl1,2-di-hydroquinoline, US Patent 2514648 (1950).
Institute Organicheskoi Khimii lmeni N.D. Zelinskogo An SSSR, Process for the Production of Substituted 1,2-Dihydroquinolines, GB Patent 1256725 (1971).
Process for the Production of Substituted 1,2-Dihydroquinolines, US Patent 38994932 (1975).
H.M. Rivera, Novel Apparatus for the Obtention of Substituted 1,2- Dihydroquinolines, US Patent 3829292 (1974).