US 4,302,394 A · Production of butyrolactone

Abstract

Butyrolactone is produced by oxidizing an aldehyde-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, to form an acid ether of the general formula: ##STR2## followed by deetherification, dehydration and cyclization. Oxidation can be carried out with e.g. gaseous oxygen. Deetherification can be accomplished by contact with an acid catalyst, while cyclization may occur spontaneously. A cyclic process is described in which allyl alcohol is converted by reaction with a suitable olefin, e.g. iso-butylene, to an allyl ether of a tertiary alcohol, e.g. allyl t-butyl ether, which is then hydroformylated to form the compound of formula (I), while the olefin, e.g. iso-butylene, released on deetherification of the acid ether of formula (II), is recycled to the allyl ether formation step.

Claims10

Dependent claims

A process for the production of butyrolactone which comprises oxidizing an aldehyde-ether of the general formula:

##STR9## 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, to form an acid-ether of the general formula:
##STR10## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above, followed by deetherification and cyclization.

A proccess for the production of butyrolactone which comprises (a) reacting allyl alcohol with an olefin of the general formula:

##STR11## 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, to form an allyl ether of the general formula:
##STR12## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above;
(b) contacting resulting allyl ether of the general formula (III) with hydrogen and carbon monoxide under hydroformylation conditions in the presence of a catalytic amount of a hydroformulation catalyst;
(c) oxidising resulting aldehyde-ether of the general formula:
##STR13## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above to form an acid-ether of the general formula:
##STR14## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above;
(d) subjecting resulting acid-ether of the general formula (II) to deetherification, dehydration and cyclisation conditions;
(e) recovering resulting butyrolactone and regenerated olefin of the general formula (IV);
and
(f) recycling resulting regenerated olefin of the general formula (IV) to step (a).

7 more elements

Dependencies are inferred from the claim text.

Production of butyrolactone

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Production of butyrolactone

Life of this patent

Abstract

Claims10