Production of butane-1,4-diol

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

C - Chemistry, Metallurgy

07

C

260/635.1

C07C 31/20 (2006.01) C07C 29/10 (2006.01) C07C 43/15 (2006.01) C07C 43/162 (2006.01) C07C 45/49 (2006.01)

Patent

CA 1134392

ABSTRACT PRODUCTION OF BUTANE-1,4-DIOL. Butane-1,4-diol is produced by converting allyl alcohol to an allyl t-alkyl or -cycloalkyl ether of the general formula: (III) Image wherein R1 and R2 each, independently of the other, represent a C1 to C4 alkyl radical, and R3 and R4 each, independently of the other, represent a hydrogen atom or a C1 to C3 alkyl radical, or wherein R1 represents a C1 to C4 alkyl radical, R2 and R3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R4 represents a hydrogen atom or a C1 to C3 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: Image (I) reducing resulting aldehyde-ether of the general formula (II) to form a corresponding hydroxy-ether of the general formula: (II) Image and cleaving resulting hydroxy-ether of the general formula (II) to give butane-1,4-diol. Typically R1 and R2 each represent a methyl group whilst R3 and R4 each represent a hydrogen atom. The alkene of the general formula: Image (IV) 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).

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