Production of butane-1,4-diol

Details Production of butane-1,4-diol Production of butane-1,4-diol

1983-09-16

1985-03-05

Evans, J. E.

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

Organic compounds

Oxygen containing

568671, 568678, 568689, C07C 2900, C07C 3120

Patent

active

045032750

ABSTRACT:
Butane-1,4-diol 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 (II) to form a corresponding hydroxy-ether of the general formula: ##STR3## and cleaving resulting hydroxy-ether of the general formula (II) to give butane-1,4-diol. 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: 2067385 (1937-01-01), Evans et al.
patent: 3022340 (1962-02-01), Bloch
patent: 3448157 (1969-06-01), Slaugh et al.
patent: 4024197 (1977-05-01), Cumbo et al.
patent: 4029710 (1977-06-01), Suzuki
patent: 4287127 (1981-09-01), Harris et al.
Evans et al., "Industrial and Engineering Chemistry", vol. 28, No. 10, Oct. 1936, pp. 1186 to 1188.

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