Davy Mckee (london) Limited

Davy Mckee (oil & Chemicals) Limited

Davy Mckee Corporation

Davy Research and Development Limited

Alan J Dennis

George E Harrison

Norman Harris

James P Wyber

Donald H McKinley

Mohammad Sharif

Arthur James Reason

Thomas F Shevels

Aldolisation-dehydration process

A diaryl carbonate is produced by transesterification of a dialkyl carbonate, such as dimethyl carbonate, with an aromatic hydroxy compound, such as phenol, in three successive reaction zones. A transesterification catalyst, such as a titanate ester or ester mixture is used in each zone. Conditions are selected to maximize formation of alkyl aryl carbonate in the first and second reaction zones, while conversion to diaryl carbonate is favored in the third reaction zone. The vaporous mixture from the first two reaction zones is a mixture containing alkyl alcohol, dialkyl carbonate, alkyl aryl carbonate and aromatic hydroxy compound. This mixture is separated in an alkyl alcohol recovery zone by distillation in the distillation columns to produce useful recycle streams. The second of these distillation columns can be operated at a lower pressure than the first, thus enabling the heat of vaporization of this mixture to be used as the source of heat for the reboiler of the second distillation column of the alkyl alcohol recovery zone.

Continuous production process of diarylcarbonates

Multi-step hydrodesulphurization process

Multi-step hydrodesulphurisation process

Catalytic hydrogenation process

Process for the production of aldehydes by hydroformylation

A continuous hydroformylation process for the production of an aldehyde by hydroformylation of an olefin comprises:

Continuous process for the production of aldehydes by hydroformylation

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).

Production of butane-1,4-diol

A process for the production of an aldehyde by hydroformylation of an olefin comprises:

Process for the preparation of aldehydes by hydroformylation of olefins

A continuous process for the production an aldehyde by hydroformylation of an optionally substituted alpha-olefin comprises:

Process for the production of aldehydes by hydroformylation of

A process for the production of a non-linear aldehyde by hydroformylation of an optionally substituted internal olefin comprises:

Hydroformylation process

Aldehyde ethers 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, and wherein Y represents --CH.sub.2 --CH.sub.2 --CH.sub.2 or --CH.sub.2 --CH (CH.sub.3)--, are prepared by hydroformylation of a corresponding compound of formula. ##STR2## by reaction with hydrogen and carbon monoxide in the presence of a hydroformylation catalyst, e.g. a rhodium complex catalyst. Preferred compounds include 4-t-butoxybutyraldehyde and 3-t-butoxy-2-methylpropionaldehyde. The compounds are useful chemical intermediates in the production of, for example, butane-1,4-diol, butyrolactone and tetrahydrofuran.

Aldehyde-ethers

Aldehyde ethers 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, and wherein Y represents --CH.sub.2 --CH.sub.2 --C.sub.2 or --CH.sub.2 --CH (CH.sub.3)--, are prepared by hydroformylation of a corresponding compound of formula: ##STR2## by reaction with hydrogen and carbon monoxide in the presence of a hydroformylation catalyst, e.g. a rhodium complex catalyst. Preferred compounds include 4-t-butoxybutyraldehyde and 3-t-butoxy-2-methylpropionaldehyde. The compounds are useful chemical intermediates in the production of, for example, butane-1,4-diol, butyrolactone and tetrahydrofuran.

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.

Production of butyrolactone

n-Valeraldehyde is produced by hydroformylation of butene-1 in the presence of one or more of cis- and trans-butene-2 and iso-butylene using a rhodium complex catalyst such as HRh(CO)PPh.sub.3).sub.3. Reaction conditions include use of at least about 100 moles of free triorganophosphine per gram atom of rhodium, a temperature of about 80.degree. C. to about 130.degree. C., a total pressure of not more than about 50 kg/cm.sup.2 absolute, a partial pressure of carbon monoxide of not more than about 1.5 kg/cm.sup.2 absolute, and a partial pressure of hydrogen of from about 1.0 to about 7.5 kg/cm.sup.2 absolute. An n-/iso-ratio of 20:1 and a conversion efficiency of butene-1 to n-valeraldehyde of over 85% are possible under these conditions with essentially no resin formation despite the presence of iso-butylene. The n-/iso-valeraldehyde mixture can be aldolized and reduced without intermediate purification to give a commercially acceptable C.sub.10 -plasticizer alcohol.

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Middlesbrough, United Kingdom

Alan J Dennis