Process for producing 3-methyltetrahydrofuran

Details Process for producing 3-methyltetrahydrofuran Process for producing 3-methyltetrahydrofuran

1996-02-01

1997-04-08

Owens, Amelia

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30702

Patent

active

056189532

ABSTRACT:
A process for producing 3-methyltetrahydrofuran, wherein in a first step, prussic acid is reacted with methyl methacrylate to produce methyl 3-cyanoisobutyrate. The methyl 3-cyanoisobutyrate is then reacted with water and sulfuric acid to produce a resultant product which is reacted with a C.sub.1 -C.sub.8 aliphatic alcohol to produce a methylsuccinic acid ester. The methylsuccinic acid ester is catalytically hydrogenated to prepare the 3-methyltetrahydrofuran. Alternatively, the methyl 3-cyanoisobutyrate is hydrated to produce methyl 3-carbamoylisobutyrate, which is then reacted with a formic acid ester to form a methylsuccinic acid ester and formamide and the resultant methylsuccinic acid ester is catalytically hydrogenated. The 3-methyltetrahydrofuran is produced in high selectivity and in a commercially advantageous manner from inexpensive reactants. The 3-methyltetrahydrofuran is useful as a commoner for producing polyether glycol, which is utilized as starting raw material for preparing spandex fiber.

REFERENCES:
patent: 3859369 (1975-01-01), Copelin
patent: 4124600 (1978-11-01), Jenkins, Jr.
patent: 4772729 (1988-09-01), Rao
Elisabeth Dane et al, "Uber die Umsetzung von Brenz-traubens aure mit primaren aromatischen Aminen zu Derivaten der Brenzweins aure und der Aceturs aure Reaktionen der Brenztraubens aure I", Justus Liebigs Annalen der Chemie, vol. 607, 1957, pp. 92-108.
Database WPI, Section Ch, Week 9549, Derwent Publications Ltd., London, GB, AN 95-380015 of JP-A-07 258 149 (Kuraray Co., Ltd.) Oct. 9, 1995.

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