Process for preparing methylolhydantoins

Details Process for preparing methylolhydantoins Process for preparing methylolhydantoins

C - Chemistry, Metallurgy

07

D

C07D 233/72 (2006.01) C07D 233/78 (2006.01)

Patent

CA 2096675

There are provided methods for producing solid anhy- drous methylolhydantoins. Initially, an aqueous stirrable medium is dehydrated and heated to yield a substantially anhydrous stirrable melt. The aqueous stirrable medium includes (A) a solute selected from the group consisting of (i) a dimethyloldimethylhydantoin, (ii) a hydantoin reactant, (iii) a formaldehyde source reactant, or (iv) a combination of any of the foregoing; and (B) optionally a catalyst. A molten system is then provided by adding, to the stirrable melt, a reactant mixture which includes (A)(i) the same or a different hydantoin reactant, (ii) a substantially anhydrous formaldehyde source reactant which may be the same as or different than the formalde- hyde source reactant, or (iii) a combination thereof; and (B) optionally, the same or a different catalyst; wherein the molten system includes (i) at least one hydantoin reactant and (ii) at least one dehydrated formaldehyde source reactant or substan- tially anhydrous formaldehyde source reactant. The at least one hydantoin reactant and the at least one dehydrated formaldehyde source reactant or substantially anhydrous formaldehyde source reactant in the molten system are reacted, while reaction water is removed, to yield anhydrous molten methylolhydantoin. Final- ly, the molten methylolhydantoin is solidified. Alternatively, solid anhydrous methylolhydantoin is produced by reacting, in an aqueous stirrable medium as above, a reactant mixture of (i) the same or a different hydantoin reactant, (ii) a substantially anhydrous formaldehyde source reactant which may be the same as or different than the formaldehyde source reactant, or (ii) a combination thereof and (iv) optionally, the same as or different catalyst; wherein (i) at least one hydantoin reactant and (ii) at least one formaldehyde source reactant or substantially anhydrous formaldehyde reactant is present; while heating to at least the melting temperature of the methylolhydantoin and while removing substantially all water; to yield a molten methylolhydantoin; and subsequently solidifying the molten methylolhydantoin. These methods can be practiced as batch processes or as semi-continuous processes.

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