US 5,856,531 A · Preparation of 3-methytetra-hydrofuran from 2,3-dihydrofuran

Abstract

Disclosed is a two-step process wherein (1) 2,3-dihydrofuran is reacted with a trialkyl orthoformate in the presence of an acidic catalyst to produce a 2-alkoxy-3-(dialkoxymethyl)tetrahydrofuran intermediate and (2) the intermediate is contacted with hydrogen in the presence of a catalyst system comprising a Group VIII noble metal or rhenium and a strong acid to convert the intermediate to a mixture of 3-methyltetrahydrofuran (3-MeTHF) and 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF). The 3-MeTHF produced in accordance with the present invention is useful as an industrial solvent and as a co-monomer in the manufacture of polymers such as elastomers. 3-HOMeTHF may be used as a solvent and in the manufacture of pharmaceutical and agricultural chemicals and acrylate and methacrylate esters for use in preparing polymers such as polyacrylates.

Claims9

Dependent claims

Process for the preparation of a mixture of 3-methyltetrahydrofuran (3-MeTHF) and 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF) which comprises the steps of:

(1) contacting 2,3-dihydrofuran (2,3-DHF) with a trialkyl orthoformate having the formula ##STR4## in the presence of an acidic catalyst to produce an intermediate compound having the formula ##STR5## and (2) contacting the intermediate compound from step (1) with hydrogen and water in the presence of a catalytic amount of a Group VIII noble metal or rhenium and a strong acid;
wherein R.sup.1, R.sup.2 and R.sup.3 are alkyl radicals.

Process for the preparation of a mixture of 3-methyltetrahydrofuran (3-MeTHF) and 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF) which comprises the steps of:

(1) contacting 2,3-dihydrofuran (2,3-DHF) with a trialkyl orthoformate having the formula ##STR6## in the presence of in the presence of an acidic catalyst selected from Bronsted and Lewis acids at a temperature of about -10.degree. to 20.degree. C. in an orthoformate (I):2,3-DHF mole ratio of 2:1 to 10:1 to produce an intermediate compound having the formula ##STR7## and (2) contacting the intermediate compound from step (1) with hydrogen and water in the presence of a catalytic amount of a Group VIII noble metal selected from palladium and platinum and a strong acid selected from sulfuric, phosphoric and sulfonic acids at a temperature of about 70.degree. to 180.degree. C. and a hydrogen pressure of about 8 to 50 bars absolute;
wherein R.sup.1, R.sup.2 and R.sub.3 are independently selected from alkyl of up to about 4 carbon atoms.

Dependencies are inferred from the claim text.

Preparation of 3-methytetra-hydrofuran from 2,3-dihydrofuran

Life of this patent

Preparation of 3-methytetra-hydrofuran from 2,3-dihydrofuran

Life of this patent

Abstract

Claims9