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A one-step, phosgene-free route to urethane

By Chemical Engineering |

Researchers at the National Institute of Advanced Industrial Science and Technologys (AIST) Interdisciplinary Research Center for Catalytic Chemistry (Tsukuba, Japan; www.aist.go.jp) have developed a new reaction process to synthesize aromatic urethane — a promising starting material for the production of polyurethanes. Unlike traditional urethane routes, no phosgene is required. The process is a one-step reaction in which an amine is reacted with a tin-alkoxide compound and pressurized CO2. Yields as large as 82% have been achieved by reacting aniline and dibutyltin dimethoxide (mole ratio of 1:5) for 20 min at 150°C, using a CO2 pressure of 5 MPa. A 49% yield was found using 2,4-diaminotoluene — the precursor for polyurethanes. After the reaction, the tin compound could be recovered and reused after treatment with an alcohol. The group plans to enhance the efficiency, and scale up the process to realize industrial applications.
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