Synthesis of carbamate or urea compounds
AssigneeNederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
InventorsAntonius Eduard Dominicus Maria Van Der Heijden, Erik Van Geest, Jos Johan Matthijs Hugo Van Den Elshout
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Abstract
The invention pertains to the synthesis of carbamate and urea compounds. In particular the invention is directed to the synthesis of carbamate and urea compounds which may be used in the production of compounds that are used to stabilize nitrocellulose. The method of the invention comprises preparing a carbamate or urea derivative comprising reacting an amine and a carbonate or carbamate in the presence of an ionic liquid.
Claims16
A method for preparing an N,N-diaryl substituted urea derivative for nitrocellulose stabilization, said method comprising a first step of preparing a carbamate according to formula I, comprising reacting an amine according to formula II and a compound according to formula III, in the presence of a catalyst that comprises an N,N-dialkylimidazolium ionic liquid or a non-nucleophilic base
- wherein
- Ar1 is an aryl that is optionally substituted with one or more of halide, alkoxy, alkyl, nitro, sulfonate, ester, amide and/or carboxylate;
- Ar2 is Ar1 or an aryl that is optionally substituted with one or more of halide, alkoxy, alkyl, nitro, sulfonate, ester, amide and/or carboxylate;
- X is an alkoxy, or an aryloxy and is optionally substituted with one or more of halide, alkoxy, alkyl, nitro, sulfonate, ester, amide and/or carboxylate;
- and
- LG is an alkoxy, an aryloxy, an amine that is optionally substituted with one or two C1-C4 alkyl groups, an amide, a sulfonate, a halide, a nitrate, a phosphate or a carboxylate;
- wherein the catalyst is present in less than 50 mol % with respect to the amine according to formula II;
- and
- followed by a second step wherein the carbamate according to formula I is reacted with an amine to form said N,N-diaryl substituted urea derivative for nitrocellulose stabilization.
Dependencies are inferred from the claim text.