Patents Assigned to Davy McKee (Oil & Chemicals) Limited
  • Patent number: 4414420
    Abstract: 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.
    Type: Grant
    Filed: April 7, 1982
    Date of Patent: November 8, 1983
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4391677
    Abstract: A process is disclosed for producing a substantially sulphur-free, butene-1 rich stream from a butene-containing C.sub.4 hydrocarbon feed stream by passage through a desulphurization zone, e.g. successive beds of active alumina and zinc oxide, and then distilling it. The desulphurization zone adsorbs, absorbs or converts to higher boiling sulphurous compounds low boiling sulphurous impurities such as H.sub.2 S, COS and CH.sub.3 SH. A sulphur-free butene-1 rich stream is recovered overhead from the distillation zone, while a butene-2 rich stream containing higher boiling sulphurous impurities originally present or produced in the desulphurization zone is recovered as a bottom product. A dechlorination zone (containing, for example, a charge of copper impregnated active carbon) can be provided upstream or downstream from the desulphurization zone but upstream from the distillation zone or can be provided in the path of the butene-1 rich stream from the distillation zone.
    Type: Grant
    Filed: August 27, 1981
    Date of Patent: July 5, 1983
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, John F. Flintoff, John W. Kippax
  • Patent number: 4383125
    Abstract: 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.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: May 10, 1983
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4311564
    Abstract: A distillation tray is described which is suitable for use in a distillation column of a barge-mounted plant. This distillation tray is provided with a plurality of cup-like cavities, each cavity having an apertured bottom for upward passage of vapor and being provided with respective weir means and downpipe means for feeding excess liquid to the tray below. In use of such a distillation tray a body of liquid can be maintained in each cavity for contact with the upflowing vapor and for providing a liquid seal between stages despite tilting of the tray. Each cavity can be provided by an insert comprising an apertured bottom plate, upstanding walls defining together with the bottom plate a cup-like cavity, at least one of the walls being provided with weir means for overflow of excess liquid from the cavity and downpipe means mounted below the bottom plate for transferring excess liquid that has overflowed the weir means to the tray below.
    Type: Grant
    Filed: June 6, 1980
    Date of Patent: January 19, 1982
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventor: Dennis R. Aldridge
  • Patent number: 4302394
    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.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: November 24, 1981
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventor: Alan J. Dennis
  • Patent number: 4287370
    Abstract: 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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 1, 1981
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, Alan J. Dennis, Thomas F. Shevels
  • Patent number: 4287127
    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.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: September 1, 1981
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4287369
    Abstract: A rhodium-catalyzed hydroformylation process in disclosed in which an overhead vapor stream is recovered from the hydroformylation zone containing reactant alkene, hydrogen, carbon monoxide, alkene hydrogenation product(s), aldehyde product and aldehyde condensation products. This vapor stream is subjected to condensation conditions in one or two stages to condense therefrom condensible components comprising unreacted alkene, aldehyde product, and aldehyde condensation products. Non-condensed components of the vapor stream (e.g. H.sub.2 and CO) are recycled to the hydroformylation zone. Unreacted alkene is also recycled in liquid form to the hydroformylation zone.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 1, 1981
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, Thomas F. Shevels