Preparation of urethane and carbonate products

Details Preparation of urethane and carbonate products Preparation of urethane and carbonate products

1992-10-15

1994-04-12

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

558275, 560115, C07D21116, C07C 6804

Patent

active

053027175

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 a base selected from the group consisting of a phosphazene compound and a mixture of a phosphazene compound and an organic, nitrogenous 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.

REFERENCES:
patent: 4467089 (1984-08-01), Bechara
patent: 5200547 (1993-04-01), Riley et al.
Grant, R., Grant & Hackh's Chemical Dictionary, fifth edition, 1987, p. 444.
Aresta, M. and Quaranta, E., "Role of the Macrocyclic Polyether in the Synthesis of N-Alkylcarbamate Esters from Primary Amines, CO.sub.2 and Alkyl Halides in the Presence of Crown-Ethers", Tetrahedron, 48, 1515-30 (1992).
Yoshida, Y. et al., "Novel Synthesis of Carbamate Ester from Carbon Dioxide, Amines, and Alkyl Halides", Bull. Chem. Soc. Jpn., 62, 1534-38 (1989).
Hori, Y. et al., "New Organic Synthesis with DBU: Part 7. Synthesis of Carbonates and Carbamates with Carbon Dioxide Gas as the Starting Material", Chemistry Express, vol. 1, No. 4, pp. 224-227 (1986).
Schwesinger, R. and Schlemper, H., "Peralkylated Polyaminophosphazenes--Extremely Strong, Neutral Nitrogen Bases", Angew. Chem. Int. Ed. Engl., 26, 11, pp. 1167-1169 (1987).
Schwesinger, R. "Extremely Strong, Non-ionic Bases: Synthesis and Applications", Chimia, 39, 9, pp. 269-272 (1985).

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