Process of preparing N-substituted aldonamides

US5386018A · kind A · utility

Assignee

• Lever Brothers Company, division of Conopco, Inc. · US

Inventors

• Van Au · Oxford, US
• Bijan Harichian · Brookfield, US
• Michael I. Hill · Fords, US
• Mikhail Raykh · East Brunswick Township, US
• Jerry J. Krupa · Rockaway, US

Key dates

• Filing date: Nov 4, 1993
• Grant date: Jan 31, 1995
• Expiry date: Nov 4, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C235/06
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

N-substituted aldonamides are synthesized by the reaction of alkylamines and aldonolactone. Commercially available sources of aldonolactones (e.g., lactobiono-1,5-lactone) include aldonic acid (e.g., lactobionic acid). The presence of the acid leads to the formation of an ammonium salt impurity. The ammonium salt formation during the synthesis of N-alkyl aldonamides was minimized by the addition of an external acid. External acids and, optionally, emulsifiers were utilized to substantially reduce or eliminate the formation of an ammonium salt and to obtain N-substituted aldonamides of high purity.