Celanese Gmbh

Hoechst Celanese Corporation

James H George

Theodore Horlenko

Jerry A Broussard

Wayne C Fuqua

A process is provided for the production of a monohydroxy monocyclic acetal, e.g., trimethylolpropane cyclic formal, of a trihydroxy alcohol, e.g., trimethylolpropane, and an aldehyde, e.g., formaldehyde, by subjecting a 'heavier condensation product' of the trihydroxy alcohol and the aldehyde than the desired cyclic acetal, i.e., one having a higher molecular weight and boiling point, to acetal formation conditions. In a preferred embodiment, the product of reaction of the trihydroxy alcohol and aldehyde is treated to remove the desired monohydroxy monocyclic acetal product and at least part of the remainder comprising the heavier condensation product is recycled to the reaction together with a flesh supply of trihydroxy alcohol and aldehyde. The monohydroxy monocyclic acetal product may be further reacted to obtain a desired ester, e.g. trimethylolpropane cyclic formal acrylate, such as by transesterifying the acetal with a low boiling ester of the esterifying acid, e.g., methyl acrylate, using tetra-isopropyl orthotitanate as transesterification catalyst.

Production of monohydroxy monocyclic acetals and their esters

A process is provided for producing N-acyl-acyloxy aromatic amine, such as 4-acetoxyacetanilide by reacting a hydroxy-aromatic ketoxime with a carboxylic acid anhydride, e.g. acetic anhydride, in the presence of phosphoric or oxalic acid as a Beckmann rearrangement catalyst. Preferably the ketoxime is prepared by reacting a hydroxy aromatic ketone such as 4-hydroxyacetophone with a hydroxyl amine salt, and the ketone is obtained by the Fries rearrangement of a phenolic ester, e.g. phenyl acetate or the Friedel-Crafts acylation of a phenolic compound, e.g. phenol, with an acylating agent, e.g. acetic acid.

Process for producing n-acyl-acyloxy aromatic amines

Phenolic compounds, such as phenol itself, are formed by oxidizing the corresponding aromatic aldehyde precursors, in the vapor phase, with molecular oxygen, the gaseous oxidation product being cooled in the presence of an inert diluent to prevent formation of tarry condensation products. In a particular embodiment a mixture of toluene and benzaldehyde is reacted with oxygen to convert the benzaldehyde to phenol while a portion of the toluene is oxidized to benzaldehyde which is recycled. The products are separated by solvent extraction.

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Portland, TX, United States of America

James H George