Processes for making C3 products from ethylene and syngas using hydroformylation strategies

A method of using ethylene, comprising the steps of:

• (a) providing an ethylene feed mixture comprising 80 to 98 weight percent of ethylene based on the total weight of hydrocarbons in the feed mixture, wherein a first portion of the ethylene is derived from a renewable feedstock and an optional second portion of the ethylene is derived from ethane;
• (b) contacting the feed mixture with a gas mixture comprising excess hydrogen and excess carbon monoxide in the presence of a catalyst under hydroformylation conditions effective to provide a product mixture comprising propionaldehyde, unreacted hydrogen, and unreacted CO;
• (c) recovering a first product mixture portion from the product mixture, said first product mixture portion comprising a major portion of the propionaldehyde prepared in step (b);
• (d) recovering a second product mixture portion from the product mixture, said second product mixture portion comprising a major portion of the unreacted CO and unreacted hydrogen in the product mixture;
• and
• (e) recycling and using at least a portion of the CO and hydrogen in the second product mixture portion in step (b);
• and
• wherein optionally substantially all of the ethylene used in step (a) is derived from at least one renewable resource;
• and wherein optionally substantially all of the hydrogen and carbon monoxide used in steps (c) and (d) are independently derived from one or more renewable resources;
• and wherein optionally substantially all of the reactants used in step (c) to prepare the propionaldehyde are derived from one or more renewable resources such that the propionaldehyde is a substantially 100% renewably sourced propionaldehyde.

A method of using ethylene, comprising the steps of:

• (a) using a first gas mixture comprising methane and ethane to make a second gas mixture comprising carbon monoxide and hydrogen;
• (b) contacting a portion of the second gas mixture with a feed mixture comprising ethane and ethylene in the presence of a catalyst under hydroformylation conditions effective to prepare a product mixture comprising unreacted ethane and propionaldehyde, wherein the feed mixture comprises 80 to 98 weight percent of ethylene based on the total weight of hydrocarbons in the feed mixture;
• (c) recovering a first product mixture portion from the product mixture, said first product mixture portion comprising a major portion of the propionaldehyde prepared in step (b);
• (d) recovering a second product mixture portion from the product mixture, said second product mixture portion comprising a major portion of the ethane in the product mixture;
• (e) using a portion of the hydrogen prepared in step (a) to convert at least a portion of the propionaldehyde in the first product mixture portion into propanol;
• and
• (f) optionally recycling and using at least a portion of the ethane in the second product mixture portion to prepare a portion of the carbon monoxide and hydrogen in step (a).

A method of purifying ethane from a mixture comprising ethane and ethylene, comprising the steps of:

• (a) providing a feed mixture comprising ethane, ethylene, a light fraction, and a heavy fraction, wherein the light fraction comprises hydrogen, carbon monoxide, and methane, and wherein the heavy fraction comprises one or more hydrocarbons comprising three or more carbon atoms;
• (b) partially purifying the feed mixture in a manner effective to separate a majority of the light fraction and a majority of the heavy fraction from the feed mixture and such that the partially purified feed mixture comprises 80 to 98 weight percent of ethylene and 1 to 20 weight percent ethane based on the total weight of hydrocarbons in the partially purified feed mixture;
• (c) contacting the partially purified feed mixture of step (b) with a gas mixture comprising hydrogen and carbon monoxide in the presence of a catalyst under hydroformylation conditions effective to provide a product mixture comprising propionaldehyde and unreacted ethane;
• (d) recovering a first product mixture portion from the product mixture, said first product mixture portion comprising at least 96 weight percent of the ethane in the product mixture based on the total weight of ethane in the product mixture;
• (e) recovering a second product mixture portion from the feed mixture, said second product mixture portion comprising a major portion of the propionaldehyde;
• (f) using at least a portion of the ethane in the first product mixture to prepare at least a portion of the ethylene used in step (a).