SUBSTITUTED (ALPHA)-AMINOACETAMIDES AND CATALYTIC METHODS FOR THEIR PREPARATION

Novel .alpha.-aminoacetamides are powerful stabilizers for organic materials subject to oxygen and heat degradation, and particularly for synthetic natural rubber and synthetic ester lubricants. A wide range of substituents on the amine and amide N atoms, and also on the saturated carbon atoms, yiel...

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Bibliographic Details
Main Author LAI, JOHN T
Format Patent
LanguageEnglish
French
Published 13.10.1981
Subjects
ADHESIVES
CHEMISTRY
COMPOSITIONS BASED THEREON
COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
DYES
FUELS
HETEROCYCLIC COMPOUNDS
LUBRICANTS
LUBRICATING COMPOSITIONS
MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FORELSEWHERE
METALLURGY
MISCELLANEOUS APPLICATIONS OF MATERIALS
MISCELLANEOUS COMPOSITIONS
NATURAL RESINS
ORGANIC CHEMISTRY
ORGANIC MACROMOLECULAR COMPOUNDS
PAINTS
PEAT
PETROLEUM, GAS OR COKE INDUSTRIES
POLISHES
TECHNICAL GASES CONTAINING CARBON MONOXIDE
THEIR PREPARATION OR CHEMICAL WORKING-UP
USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATINGINGREDIENTS IN A LUBRICATING COMPOSITION
USE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES ASCOMPOUNDING INGREDIENTS
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Summary:Novel .alpha.-aminoacetamides are powerful stabilizers for organic materials subject to oxygen and heat degradation, and particularly for synthetic natural rubber and synthetic ester lubricants. A wide range of substituents on the amine and amide N atoms, and also on the saturated carbon atoms, yields an array of stabilizers having a wide range of compatibility in compositions comprising various synthetic resinous compounds to be stabilized. Novel synthesis are provided utilizing at least one amine nucleophilic agent, a dichlorocarbene ion generating agent, and an alkoxide ion generating agent, which together in the presence of aqueous alkali and an onium salt, yield novel .alpha.-aminoacetamides in which a wide choice of substituents may be introduced. The nucleophilic agent may be a primary or secondary amine, or one of each. The dichlorocarbene ion generating agent is haloform. the alkoxide ion generating agent may be a ketone, an aldehyde, or a cyanohydrin which reacts with the haloform. An .alpha.-trihalomethyl alcohol also reacts with the amine nucleophilic agent, without the benefit of a dichlorocarbene ion generating agent. When the alkoxide ion generating agent is an .alpha.-trihalomethyl alcohol, an .alpha.hydrogen may optionally be substituted.
Bibliography:Application Number: CA19790326317