Chemical News

Tuesday, April 21, 2009

Ethylene Glycol without Ethylene Route

A route for making ethylene glycol without starting from ethylene is under development. Shell Chemical is a leading provider of ethylene glycol (EG) process technology. The conventional process for making EG is hydrolysis of ethylene oxide (EO), which is made by oxidizing ethylene over a silver catalyst.

For many years, the selectivity of the ethylene oxidation has been no better than ~85%; however, lately Shell has developed catalysts that are capable of achieving 90% selectivity. EO hydrolysis is typically carried out noncatalytically in a large excess of water. The selectivity to EG is only ~90%; diethylene glycol, and triethylene glycol are the byproducts. As one remedy, Shell now offers a two-step process for converting EO to EG via an ethylene carbonate intermediate that produces EG in almost 100% selectivity.

A. Lenero and colleagues at Shell are working on a different route to EG—one that does not begin with ethylene. Their method proceeds by hydroformylating formaldehyde to give glycolaldehyde, which can undergo hydrogenolysis to make EG. The first step is the difficult part, and the key to this invention is an improved catalyst for the hydroformylation step.

In one example, 0.15 mol of formaldehyde (in the form of 37% aqueous formalin), 37 mL (0.22 mol) of N,N-dibutylacetamide, 7.5 mL of water, 0.49 mmol of Rh(acac)(CO)2, 0.96 mmol of 2-phospha-2-(ethyl-N,N-dimethylamido)-1,3,5,7-tetramethyl-6,9,10-trioxa-tricyclo[3.3.1.1{3,7}]-decane, and 9.1 mmol of trimethylbenzoic acid are added to an autoclave. After the air is flushed out, the autoclave is pressurized to 3 MPa with CO and heated to 90 °C for 5 h. The conversion of formaldehyde is 90%, and the yield of glycolaldehyde is calculated to be 90%. In a separate example, glycolaldehyde is easily converted to EG by hydrogenolysis at 40 °C over Raney nickel. (Shell Oil [Houston]. US Patent 7,511,178




Source: CAS Patent Watch

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