Production of tetrahydrofuran

Details Production of tetrahydrofuran Production of tetrahydrofuran

1980-04-11

1981-09-01

Raymond, Richard

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

568670, 568678, C07D30708

Patent

active

042871271

ABSTRACT:
Tetrahydrofuran is produced by converting allyl alcohol to an allyl t-alkyl or -cycloalkyl ether of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, followed by reacting resulting compound of formula (III) under hydroformylation conditions with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst to form a corresponding aldehyde-ether of the general formula: ##STR2## reducing resulting aldehyde-ether of the general formula (I) a corresponding hydroxy-ether of the general formula: ##STR3## and cleaving resulting hydroxy-ether of the general formula (II) under dehydrating conditions to produce tetrahydrofuran. Typically R.sub.1 and R.sub.2 each represent a methyl group while R.sub.3 and R.sub.4 each represent a hydrogen atom. The alkene of the general formula: ##STR4## released upon cleavage of the hydroxy-ether of formula (II) can be recycled for reaction with further allyl alcohol to form a further quantity of the ether of the general formula (III).

REFERENCES:
patent: 3929915 (1975-12-01), Cumbo et al.
patent: 4005112 (1977-01-01), Smith
patent: 4064145 (1977-12-01), Taylor
Brown et al., Tetrahedron Letters, No. 22, (1969), pp. 1725 and 1726.
Takeshige et al., Chemical Abstracts, vol. 84, (1976), 30856k.

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