Functionalized cycloaliphatic nitrile oxides
AssigneeThe Dow Chemical Company
InventorsZenon Lysenko, Clark H. Cummins, Ramki Subramanian, Richard F. Fibiger
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Abstract
A suitably functionalized cycloaliphatic nitrile oxide can be used to convert unsaturated sites to alcohol or epoxy sites. The cycloaliphatic nitrile oxide may be useful in applications such as the preparation of polycarbonates, polyurethanes, or crosslinked polybutadiene, or poly(styrene-butadiene). The cycloaliphatic nitrile oxide is represented by the formula: ##STR1## wherein R' and each R are independently hydrogen, C.sub.1 -C.sub.12 alkyl, or halo; X and X' are independently hydrogen, halo, hydroxyl, or together with the carbon atoms to which they are attached form an epoxy group, with the proviso that at least one of X and X' is not hydrogen; and n is 1 or 2.
Claims12
A compound represented by the formula:
- ##STR16## wherein R' and each R are independently hydrogen, C.sub.1 -C.sub.12 alkyl, or halo;
- X and X' are independently hydrogen, halo, hydroxyl, or together with the carbon atoms to which they are attached form an epoxy group with the proviso that not more than one of X and X' is hydrogen;
- and n is 1 or 2.
A process for preparing a functionalized cycloaliphatic nitrile oxide represented by the formula:
- ##STR17## comprising the steps of:
- (a) contacting an epoxide represented by the formula:
- ##STR18## with a salt of hydroxyl amine under reaction conditions sufficient to form an aldoxime represented by the formula:
- ##STR19## (b) dehydrogenating the aldoxime to form the functionalized cycloaliphatic nitrile oxide;
- wherein R' and each R are independently hydrogen, C.sub.1 -C.sub.12 alkyl, or halo;
- X and X' are each independently hydroxy or halo, or together with the carbon atoms to which they are attached form an epoxy group;
- and n is 1 or 2.
A process of converting a monoalcohol having unsaturation to a polyol containing an isoxazoline group, comprising contacting the monoalcohol with a functionalized cycloaliphatic nitrile oxide under conditions suitable to form the polyol containing the isoxazoline group, wherein the cycloaliphatic nitrile oxide is represented by the formula:
- ##STR20## wherein R' and each R are independently hydrogen, C.sub.1 -C.sub.12 alkyl, or halo;
- X and X' are each independently hydroxy or halo, or X and X' together with the carbon atoms to which they are attached form an epoxy group, with the proviso that at least one of X and X' is not halo;
- and n is 1 or 2.
Dependencies are inferred from the claim text.