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US 5,200,547 AGranted
Preparation of urethane and carbonate products
AssigneeMonsanto Company
InventorsDennis P. Riley, William D. McGhee
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Abstract
The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and an allyl halide. The amine or alcohol is reacted with carbon dioxide to form the ammonium carbamate or carbonate salt which is then reacted with a palladium tertiary phosphine catalyst complex of an allyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
Claims19
A process for preparing urethanes and carbonates comprising:
- a) bringing CO.sub.2 and a primary or secondary amine, an alcohol, an aminoalcohol, or a mixture thereof into reactive contact in the presence of a tertiary amine base, and in a solvent to form the corresponding ammonium carbamate salt or carbonate salt, and
- b) reacting said salt with an allyl halide in the presence of a palladium tertiary phosphine catalyst system.
A process of preparing a compound of the formula:
- ##STR8## wherein R.sub.1 represents an allyl radical;
- A represents a radical selected from the group consisting of --NR.sub.2 R.sub.3 and --OR.sub.4 wherein R.sub.2, R.sub.3 and R.sub.4 independently represent hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or aralkenyl radicals having from 1 to about 22 carbon atoms;
- or R.sub.2 and R.sub.3 together with the nitrogen of the radical --NR.sub.2 R.sub.3 may be bound to form a heterocyclic 5 to 9 membered ring radical;
- or R.sub.2 or R.sub.3 represents a radical of the formula ##STR9## or R.sub.4 represents a radical of the formula ##STR10## wherein R represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or aralkenyl radicals having from 1 to about 22 carbon atoms;
- R.sub.5 represents an alkylene radical having from 1 to about 22 carbon atoms and n represents an integer of from 0 to about 8;
- comprising:
- a) bringing CO.sub.2 and a primary or secondary amine, an alcohol, an aminoalcohol, or a mixture thereof into reactive contact in the presence of a tertiary amine base, and in a solvent to form the corresponding ammonium carbamate salt or carbonate salt, and
- b) reacting said salt with an allyl halide in the presence of a palladium tertiary phosphine catalyst system.
5 more elements
Dependencies are inferred from the claim text.