Shell Oil Comapny

David Cleve Eubanks

Joseph Broun Powell

Paul Richard Weider

Lynn Henry Slaugh

Juan Pedro Arhancet

Thomas Carl Semple

Stephen Blake Mullin

Jiang-Jen Lin

Thomas C Forschner

Howard L Fong

Timothy Michael Nisbet

Kevin Dale Allen

Raymond Lawrence June

Marinus Van Zwienen

Terry Blane Thomason

Stephan Blake Mullin

Terry Blain Thomason

David William Johnson

The invention pertains to a method of preparing styrene or substituted styrene involving (1) converting a mixture containing alkylbenzene hydroperoxide or substituted alkylbenzene hydroperoxide to a mixture containing phenyl alkanol or substituted phenyl alkanol and (2) dehydrating the phenyl alkanol or substituted phenyl alkanol, characterized by oxidizing an alkene to an alkylene oxide in step (1) in the presence of a heterogenous catalyst and dehydrating the phenyl alkanol or substituted phenyl alkanol in step (2) in the presence of a homogenous dehydration catalyst to obtain styrene or substituted styrene.

Preparation method

1,3-Propanediol is prepared in a process which involves reacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a catalyst promoter to produce an intermediate product mixture containing 3-hydroxypropanal in an amount less than 15 wt %; extracting the 3-hydroxypropanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing 3-hydroxypropanal from the organic phase containing cobalt catalyst; hydrogenating the 3-hydroxypropanal in the aqueous phase to 1,3-propanediol; and recovering the 1,3-propanediol. The process enables the production of 1,3-propanediol in high yield and selectivity without the use of a phosphine ligand-modified cobalt catalyst.

Cobalt-catalyzed process for preparing 1, 3-propanediol from etylene

1,3-propanediol is prepared in a process which involves hydroformylating ethylene oxide:

Cobalt-catalyzed process for preparing 1,3-propanidiol

1,3-propanediol is prepared in a process in which ethylene oxide is reacted with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a catalyst promoter under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal. The 3-hydroxypropanal is extracted in water from the product mixture in more concentrated form, with the majority of the cobalt catalyst remaining in the solvent phase for recycle to the hydroformylation reaction. At least a portion of any residual catalyst in the water phase following extraction is removed by re-extraction with non-water-miscible solvent and recycled to hydroformylation. The 3-hydroxypropanal is then hydrogenated in aqueous solution to the desired 1,3-propanediol.

Process for preparing 1,3-propanediol

Growing community of inventors

Houston, TX, United States of America

David Cleve Eubanks