Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1993-07-19
1996-03-12
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554154, 554160, 554162, 554213, C11B 100, C11C 102
Patent
active
054987334
ABSTRACT:
Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.
REFERENCES:
Journal of American Chemical Society, vol. 83, 20 Apr. 1961, Lamar Field et al.: Isomerization of Aldoximes to Amides under Substantially Neutral Conditions; (Beckmann Rearrangement), pp. 1983-1986.
Contribution from the Department of Chemistry, Duke University, Nov. 1955, David S. Hoffenberg and Charles R. Hauser: Dehydration or Beckmann Rearrangement of Aldoximes with Boron Fluoride. Conversion of Aldoximes to Corresponding Amides, pp. 1496-1500.
Recueil, Journal of the Royal Netherlands Chemical Society, 95/5, May 1976, A. J. Leusink, et al.: Beckmann rearrangement of aldoximes catalyzed by transition metal salts: a dehydration-hydration reaction, pp. 123-125.
Department of Chemistry, University of California, Riverside, CA, Apr. 1974, Philip Radlick and Lauren R. Brown: A Versatile Modification of the Hofmann Rearrangement, p. 87.
Communications, p. 291, Apr. 1974: Hofmann Rearrangement with Methyl Hupobromite in situ.
Bulletin of the Chemical Society of Japan, vol. 46, No. 11, pp. 3474-3477 (1973), Mutsuo Kataoka and Masaji Ohno: Syntheses and the Beckmann Fission of Cyclic .alpha.-Hydroxyimino Ketones.
Ayorinde Folahan O.
Nwaonicha Chukwuma P.
Dees Jos,e G.
Howard University
Jones Dwayne C.
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