Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
AssigneeEastman Chemical Company
InventorsThomas James Devon, Damon Ray Billodeaux
Life of this patent
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Abstract
A vapor phase hydrogenolysis reaction to convert cyclic acetal compounds and/or cyclic ketal compounds in the presence of hydrogen to their corresponding hydroxy ether hydrocarbon reaction products using a supported noble metal catalyst. The hydrogenolysis reaction can be carried out in the vapor phase and in the absence of a polyhydroxyl hydrocarbon co-solvent.
Claims48
A hydrogenolysis process comprising:
- (a) feeding hydrogen and a cyclic compound composition to a reaction zone within a reaction vessel, said cyclic compound composition comprising cyclic acetal compounds having two oxygen atoms single bonded to the same carbon atom in the ring structure, cyclic ketal compounds having two oxygen atoms single bonded to the same carbon atom in the ring structure, or a combination thereof, and
- (b) conducting a reaction in the reaction zone comprising contacting the hydrogen with at least a portion of the cyclic compound composition in the vapor phase in the reaction zone under reaction zone conditions above the dew point of the cyclic compound composition to produce hydroxy ether hydrocarbons having at least one ether linkage and at least one primary hydroxyl group, and
- (c) withdrawing a product stream from the reaction zone comprising the hydroxy ether hydrocarbons, hydrogen, and if present any unreacted cyclic compounds;
- wherein the selectivity to the hydroxy ether hydrocarbons is greater than 80 mole %.
A hydrogenolysis process comprising reacting cyclic compounds having two oxygen atoms single bonded to the same carbon atom in the ring structure with hydrogen in a reaction zone over a noble metal catalyst in the absence of a liquid in the reaction zone to produce hydroxyl ether hydrocarbons having at least one ether linkage and at least one primary hydroxyl group, wherein said cyclic compounds comprise cyclic acetals, cyclic ketals, or a combination thereof, wherein the selectivity to said hydroxy ether hydrocarbons is greater than 80 mole %.
A process comprising contacting cyclic compounds containing 1,3-dioxolane moeities in the vapor phase with hydrogen in a reaction zone to produce a vapor hydroxy ether hydrocarbon, wherein said cyclic compounds are fed to the reaction zone as a vapor, and wherein the selectity of the process to the production of hydroxy ether hydrocarbons is at least 80%.
A hydrogenolysis process comprising feeding hydrogen and cyclic compounds, comprising cyclic acetal compounds having two oxygen atoms single bonded to the same carbon atom in the ring structure, cyclic ketal compounds having two oxygen atoms single bonded to the same carbon atom in the ring structure, or a combination thereof, to a reaction zone and reacting hydrogen and the cyclic compounds, in the vapor phase, in the presence of a -catalyst composition and withdrawing from the reaction zone a product stream comprising hydroxy ether hydrocarbons having at least one ether linkage and at least one primary hydroxyl group, wherein said catalyst composition comprises:
- A. palladium on an aluminum oxide support or a zirconium oxide support at a loading ranging from more than 0.2 wt. % up to 1 wt. % based on the weight of the catalyst composition, said support having a BET surface area of less than 300 m2/g, or
- B. palladium metal supported on an aluminum oxide support or a zirconium oxide support at a loading ranging from 0.1 wt. % up to 2 wt. %, said support doped with an alkali metal composition comprising C1-C8 carboxylates and halides of Li, other than lithium acetate, K, Na, Rb, Cs, or an alkaline earth metal;
- or a triphosphine oxide compound.
Dependencies are inferred from the claim text.