Acetone → Ethyl Propionate

The crude alcohol product typically will further comprise unreacted acetic acid and unreacted higher acid, depending on conversion, for example, in an amount of less than 90 wt. %, e.g., less than 80 wt. % or less than 70 wt. %. In terms of ranges, the unreacted acetic acid and unreacted higher acid is optionally present in amounts from 0 to 90 wt. %, e.g., from 5 wt. % to 80 wt. %, from 15 wt. % to 70 wt. %, from 20 wt. % to 70 wt. % or from 25 wt. % to 65 wt. %. Where acetone is included as a reactant, the crude alcohol product may comprise from 0.01 wt. % to 10 wt. % isopropanol, e.g., from 0.1 wt. % to 10 wt %, from 1 wt. % to 9 wt. % or from 3 wt. % to 7 wt. %. In other embodiments, the crude alcohol product comprises from 0.01 wt. % to 20 wt. % diethyl ether, e.g., from 0.1 wt. % to 10 wt. %, from 1 wt. % to 9 wt. % or from 3 wt. % to 7 wt. %. As water is formed in the reaction process, the crude alcohol product will generally comprise water, for example, in amounts ranging from 5 wt. % to 35 wt. %, e.g., from 10 wt. % to 30 wt. % or from 10 wt. % to 26 wt. %. Ethyl acetate and higher esters, e.g., propyl acetate or ethyl propionate, may also be produced during the hydrogenation of acetic acid and higher acids or through side reactions. In these embodiments, the crude alcohol product may comprise esters in an amount ranging from 0 to 20 wt. %, e.g., from 0 to 15 wt. %, from 1 to 12 wt. % or from 3 to 10 wt. %. Acetaldehyde may also be produced through side reactions. Higher esters, such as propyl acetate and ethyl propionate, may be present in an amount from 0.001 to 5 wt. %, e.g., from 0.01 to 3 wt. % or from 0.1 to 1 wt. %. In these embodiments, the crude alcohol product comprises acetaldehyde in amounts ranging from 0 to 10 wt. %, e.g., from 0 to 3 wt. %, from 0.1 to 3 wt. % or from 0.2 to 2 wt. %. In some embodiments, where propionic acid is included as a reactant, the n-propanol formed via hydrogenation may be present in the crude alcohol product in an amount ranging from 0.001 wt. % to 40 wt. %, e.g., from 0.01 wt. % 20 wt. %, from 0.04 wt. % to 20 wt. %, from 0.5 to 10 wt. %, from 1 to 8 wt. % or from 2 to 5 wt. %, or in other embodiments, in an amount ranging from 0.001 wt. % to 20 wt. %, e.g., from 0.001 wt. % to 15 wt. %, from 0.01 wt. % to 14 wt. %, from 0.13 wt. % to 13.2 wt. %, from 1.3 wt. % to 11.9 wt. %, or from 4 wt. % to 9.3 wt. %.

ORD record

ord-51fa0b05944149fbb6d92fe6b5bc0a1f

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08932372B2