Process for preparing amide derivatives from haloaminotriazines and acid halides
AssigneeAmerican Cyanamid Company
InventorRam B. Gupta
Life of this patent
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Abstract
This invention provides a process for preparing amide derivatives of acids by the reaction of haloaminotriazines and acid halides. This invention also provides a process for preparing isocyanates and isocyanate adducts from amide derivatives derived from haloaminotriazines and acid halides such as oxalyl chloride, phosgene and phosgene analogs. Melamine derived acid amides are prepared by reaction of trichloro and hexachloromelamines with chloroformates and acid chlorides. The by-product chlorine may be recycled in this process. Amides, carbamates, sulfonamides, phosphoramides, and related amide derivatives may be prepared by the novel processes of the invention.
Claims13
A process for preparing an acid amide from a haloaminotriazine and an acid halide comprising:
- contacting said haloaminotriazine with said acid halide at a temperature and for a length of time sufficient to produce said acid amide, wherein the haloaminotriazine is selected from the group consisting of:
- (i) a halogenated melamine represented by the formula (I):
- ##STR28## wherein each X group is the same or different and is selected from the group consisting of hydrogen, chloro, bromo, iodo and fluoro groups, provided that at least one X group is a halogen;
- and wherein each B group is the same or different and is selected from the group consisting of hydrogen, chloro, bromo, iodo, fluoro, alkyl, alkylenealkoxy, triazino, pyrimidino, pyridino, imidazolo, tetrazolo, silyl, cyano, perfluoroalkyl, perfluoroaryl, and perfluoroaralkyl groups;
- (ii) a halogenated guanamine represented by the formula (II):
- ##STR29## wherein X and B are the same as described above;
- and wherein R is selected from the group consisting of linear alkyl of 1 to 20 carbon atoms, cyclic or branched alkyl of 3 to 20 carbon atoms, alkenyl of 2 to 20 carbon atoms, aryl of 6 to 20 carbon atoms, aralkyl of 7 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, aryloxy of 6 to 20 carbon atoms, alkylthio of 1 to 20 carbon atoms, arylthio of 6 to 20 carbon atoms, alkylamino of 1 to 20 carbon atoms, dialkylamino of 2 to 40 carbon atoms, morpholino, piperidino, pyrrolidino, aminotriazino, alkylaminotriazino, aminoalkylaminotriazino, hydrogen, chloro, bromo, iodo, fluoro, perfluoroalkyl, perfluoroaryl, and perfluoroaralkyl groups;
- and
- (iii) a mixture of any of (i) and (ii).
A process for producing a triazine tris-acid amide from melamine via trihalomelamine comprising:
- (a) contacting said melamine with an halogen to produce hexahalomelamine;
- (b) contacting melamine with hexahalomelamine to produce trihalomelamine;
- (c) contacting said trihalomelamine with an acid halide at a temperature and for a length of time sufficient to produce triazine tris-acid amide as a product and halogen as a by-product;
- and
- (d) recycling the halogen by-product into step (a) to halogenate melamine to hexahalomelamine.
A process for producing a triazine tris-acid amide from melamine via hexahalomelamine comprising:
- (I) contacting said melamine with a halogen to produce hexahalomelamine;
- (II) contacting said hexahalomelamine with an acid halide at a temperature and for a length of time sufficient to produce triazine N,N',N"- trihalo tris-acid amide as an intermediate product and halogen as a by-product;
- (III) contacting the triazine N,N',N"-trihalo tris-acid amide intermediate of step (II) with hydrogen halide to produce triazine tris-acid amide as a final product and additional halogen as a by-product;
- and
- (IV) recycling the halogen by-product of steps (II) and (III) into step (I) to halogenate melamine to hexahalomelamine.
Dependencies are inferred from the claim text.