Process for the preparation of 3-methyltetrahydrofuran
AssigneeEastman Chemical Company
InventorWilliam Anthony Beavers
Life of this patent
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Abstract
Disclosed is a process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF) by a plurality of process steps comprising (1) esterifying 3-HOMeTHF to produce a carboxylate ester of 3-HOMeTHF, (2) pyrrolyzing the carboxylate ester to produce 3-methylenetetrahydrofuran (3-methyleneTHF), and (3) hydrogenating the 3-methyleneTHF to produce 3-MeTHF. The 3-MeTHF produced in accordance with the present invention is useful as an industrial solvent and as a monomer in the manufacture of polymers such as elastomers.
Claims12
Process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) by the steps comprising (1) contacting 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF) with a carbonyl esterification compound under esterification conditions to produce a carboxylate ester of 3-HOMeTHF;
- (2) heating the carboxylate ester of step (1) under pyrrolysis conditions to convert the carboxylate ester of 3-HOMeTHF to 3-methylenetetrahydrofuran (3-methyleneTHF);
- and (3) contacting the 3-methyleneTHF with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions of temperature and pressure.
Process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) by the steps comprising (1) contacting 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF) with acetic acid at a temperature of about 120 to 210.degree. C. in an esterification zone using apparatus which permits water to be removed from the esterification zone to produce 3-(acetoxymethyl)tetrahydrofuran (3-AcOMETHF);
- (2) heating the 3-AcOMETHF in a pyrolysis zone at a temperature in the range of about 380 to 510.degree. C. for a about 1 to 10 seconds to convert the ester compound to 3-methyleneTHF;
- and (3) contacting the 3-methyleneTHF with hydrogen at a temperature of 25 to 100.degree. C. and a pressure in the range of about 1 to 50 bar absolute in the presence of a hydrogenation catalyst selected from supported catalysts comprising about 1 to 10 weight percent palladium, platinum or rhodium deposited on a catalyst support material to convert the 3-methyleneTHF to 3-MeTHF.
Process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) by the steps comprising (1) contacting an aqueous solution of 3-(hydroxy-methyl)tetrahydrofuran (3-HOMeTHF) with acetic acid in an esterification zone at a temperature of about 120 to 210.degree. C. under reactive distillation conditions wherein water is removed as a vapor from the esterification zone and a mixture comprising 3-(acetoxymethyl)tetrahydrofuran (3-AcOMeTHF), 3-HOMeTHF and acetic acid is removed as a liquid from the esterification zone;
- (2) heating the liquid mixture from step (1) in a pyrolysis zone at a temperature in the range of about 380 to 510.degree. C. for a about 1 to 10 seconds to convert the 3-AcOMeTHF to 3-methylenetetrahydrofuran (3-methyleneTHF)THF and condensing and recovering the 3-methyleneTHF as a solution in acetic acid;
- and (3) contacting the solution of 3-methyleneTHF in acetic acid with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions of temperature and pressure to convert the 3-methyleneTHF to 3-methyltetrahydrofuran (3-MeTHF).
Dependencies are inferred from the claim text.