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US 4,056,543 AGranted
Process of preparing substituted acrylates
AssigneeEastman Kodak Company
InventorIgnazio Salvatore Ponticello
Life of this patent
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Abstract
Methylenemalonates are prepared by reacting a substituted norbornene with an electrophilic material in the presence of a lithium amide complex and pyrolyzing. The resulting acrylates are useful as fast setting, polymerizable adhesives.
Claims7
A process for preparing methylenemalonates having the formula ##STR9## wherein R.sup.2 is selected from the group consisting of alkyl or R.sup.1 ;
- R.sup.1 is selected from the group consisting of alkyl, allyl R.sup.5-- O(CH.sub.2).sub.n, glycidyl, haloalkyl, vinyl, propargyl, and cycloalkyl;
- R.sup.5 is alkyl and n is an integer of from 1 to 10, comprising (1) reacting a compound having the formula ##STR10## wherein R.sup.2 is as described above with an electrophilic material having the formula XCOOR.sup.1 wherein R.sup.1 is as described above and X is halogen in the presence of an alkyl-substituted lithium amide complex at a temperature range of -78.degree. C to -40.degree. C and (2) pyrolyzing the resulting norbornene at a temperature of 400.degree. C to 800.degree. C at 1mm to 760mm Hg pressure in an inert atmosphere.
A process of preparing a compound having the formula ##STR11## wherein R.sup.2 is alkyl or R.sup.1 ;
- R.sup.1 is selected from the group consisting of alkyl, allyl, R.sup.5 0 (CH.sub.2).sub.n, glycidyl, haloalkyl, vinyl, propargyl, and cycloalkyl;
- R.sup.5 is alkyl and n is an integer from 1 to 10 comprising (1) reacting the compound having the formula ##STR12## wherein R.sup.2 is as defined above with a compound having the formula XCOOR.sup.1 wherein R.sup.1 is as defined above and X is halide in the presence of lithium N-isopropylcyclohexylamide at at temperature of -78.degree. C to -40.degree. C and (2) pyrolyzing the resultant product at a temperature of 400.degree. C to 800.degree. C at 1mm to 760mm Hg pressure in an inert atmosphere.
Dependencies are inferred from the claim text.