Preparation of urethane and carbonate products
AssigneeMonsanto Company
InventorsWilliam D. McGhee, Barry L. Parnas, Dennis P. Riley, John J. Talley
Life of this patent
Estimating the term…
Abstract
The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
Claims14
A process for preparing urethanes comprising:
- (a) bringing CO.sub.2 and an amine represented by the formula R.sub.2 R.sub.3 NH or an amino acid, wherein R.sub.2 and R.sub.3 independently are hydrogen, radicals having 1 to about 22 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl, and radicals having the formula --(--R.sub.5 --).sub.n --NHR wherein R represents hydrogen and radicals selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl having 1 to about 22 carbon atoms, R.sub.5 represents alkylene radicals having from 1 to about 22 carbon atoms and n is an integer from 0 to about 8 provided that no more than one of R.sub.2 and R.sub.3 is hydrogen into reactive contact in the presence of a strongly basic nitrogenous compound selected from amidine and guanidine bases to form the corresponding ammonium carbamate salt, and
- (b) reacting, in a polar aprotic solvent, said salt with a primary or secondary hydrocarbyl halide.
A process for preparing urethanes of the formula ##STR14## wherein R.sub.1 represents alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl and aralkenyl radicals having from 1 to about 22 carbon atoms provided that R.sub.1 is not a tertiary radical of the formula (R).sub.3 C-- or (R).sub.2 .dbd.C(R)--;
- R.sub.2 ' and R.sub.3 ' independently are hydrogen, radicals having 1 to about 22 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl, and radicals having the formula ##STR15## wherein R.sub.1 is as defined above, R represents hydrogen and radicals having 1 to about 22 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl, R.sub.5 represents alkylene radicals having from 1 to about 22 carbon atoms and n is an integer from 0 to about 8, provided that no more than one of R.sub.2 ' and R.sub.3 ' is hydrogen;
- and R.sub.3 " is hydrogen and radicals having 1 to about 22 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl, comprising:
- (a) bringing CO.sub.2 and an amine represented by the formula R.sub.2 R.sub.3 NH or an amino acid, wherein R.sub.2 and R.sub.3 independently are hydrogen, radicals having 1 to about 22 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl, and radicals having the formula --(--R.sub.5 --).sub.n --NHR wherein R represents hydrogen and radicals having 1 to about 22 carbon atoms selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkenaryl and alkaryl, R.sub.5 represents alkylene radicals having from 1 to about 22 carbon atoms and n is an integer from 0 to about 8, provided that no more than one of R.sub.2 and R.sub.3 is hydrogen, into reactive contact in the presence of a strongly basic nitrogenous compound selected from amidine and guanidine bases to form the corresponding ammonium carbamate salt, and
- (b) reacting, in a polar aprotic solvent, said salt with a primary or secondary hydrocarbyl halide.
Dependencies are inferred from the claim text.