Patents by Inventor George E. Harrison

George E. Harrison has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5536856
    Abstract: Esterification is carried out in a column reactor (14) in which there is a plurality of esterification trays (15) each having predetermined liquid hold-up and containing a charge of a solid esterification catalyst thereon. e.g. an ion exchange resin containing a --SO.sub.3 H and/or --COOH groups. A liquid phase containing the carboxylic acid component, e.g. a fatty acid mixture, flows down the column reactor from one esterification tray to the next downward one against an upflowing alcohol vapour stream, e.g. methanol vapour. Relatively dry alcohol vapour is injected (21) into the bottom of the column reactor. Water of esterification is removed from the top of the column reactor in the vapour stream (26), whilst ester product is recovered (23) from the sump of the reactor. As the liquid flows down the trays it encounters progressively drier alocohol and the esterification equilibrium reaction is driven further and further towards 100% ester formation.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: July 16, 1996
    Assignee: Davy Process Technology Limited
    Inventors: George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
  • Patent number: 5434313
    Abstract: An aldolisation-dehydration process is disclosed for converting an aldehyde, e.g. n-valeraldehyde, to a substituted acrolein, e.g. propyl butyl acrolein (2-propylhept-2-enal). Aldolisation and dehydration are effected in a stirred tank reactor (16; 111) using an alkali catalyst, such as sodium hydroxide. A reaction product stream (23; 113) containing both organic and aqueous phases is distilled (in column 25; 123) to yield a heterogeneous azeotrope containing water and aldehyde. On condensation and phase separation the lower water layer (34; 150) can be discharged from the plant without the need for neutralisation. From the bottom of the distillation zone a mixture (36;157) of substituted acrolein and alkali catalyst solution is obtained. The substituted acrolein is recovered as product (45;173), while the catalyst solution (47;175) is recycled to the aldolisation reactor. Part (49; 181) of the catalyst solution is purged to control the level of Cannizzaro reaction products.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: July 18, 1995
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, Arthur J. Reason, Alan J. Dennis, Mohammad Sharif
  • Patent number: 5426207
    Abstract: 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.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: June 20, 1995
    Assignee: Davy Research and Development Limited
    Inventors: George E. Harrison, Alan J. Dennis, Mohammad Sharif
  • Patent number: 5292428
    Abstract: Liquid sulphur-containing hydrocarbon feedstock is passed through two or more hydrodesulfurization zones and connected in a series each containing a packed bed of solid sulfurized catalyst. The liquid is passed from the first zone to the next until the final zone. Make up hydrogen is supplied to a hydrodesulfurization zone (i) other than the first hydrodesulfurization zone; hydrogen-containing gas is recovered from each hydrodesulfurization zone. The first hydrodesulfurization zone is supplied with hydrogen-containing gas recovered from a subsequent hydrodesulfurization zone. Hydrogen-containing gas recovered from the first hydrodesulfurization zone is purged. Liquid material recovered from the first hydrodesulfurization zone is recycled to the inlet of the hydrosulfurization zone so as to provide diluent for admixture with liquid feedstock.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: March 8, 1994
    Assignee: Davy McKee (London) Ltd.
    Inventors: George E. Harrison, Donald H. McKinley, Alan J. Dennis
  • Patent number: 5252198
    Abstract: A hydrodesulfurization process is provided for continuously effecting hydrodesulfurization of a liquid sulfur-containing hydrocarbon feedstock which comprises: (a) providing a hydrodesulfurization zone maintained under hydrodesulfurization conditions and comprising a column reactor having a plurality of reaction trays therein mounted one above another, each tray defining a respective reaction stage adapted to hold a predetermined liquid volume and a charge of a sulfided solid hydrodesulfurization catalyst therein, liquid downcomer means associated with each reaction tray adapted to allow liquid to pass down the column reactor from that tray but to retain solid catalyst thereon, and gas upcomer means associated with each reaction tray adapted to allow gas to enter that tray from below and to agitate the mixture of liquid and catalyst on that tray; (b) supplying liquid sulfur-containing hydrocarbon feedstock to the uppermost one of said plurality of reaction trays; (c) supplying hydrogen-containing gas below th
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: October 12, 1993
    Assignee: Davy McKee (London) Ltd.
    Inventors: George E. Harrison, Donald H. McKinley, Alan J. Dennis
  • Patent number: 5157168
    Abstract: An improved process for the production of fatty alcohols is provided. The fatty alcohols are produced by hydrogenation of lower alkyl esters, especially methyl esters, of fatty acids derived from natural triglycerides, under conditions which minimize formation of by-product alkanes and ethers. The hydrogenation is followed by refining of any resulting ester-containing hydrogenation product to produce a substantially ester free fatty alcohol.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: October 20, 1992
    Assignee: Davy McKee (London) Limited
    Inventors: Martyn Wilmott, George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
  • Patent number: 5138106
    Abstract: An improved process for refining alcohols produced by hydrogenation of esters wherein the crude hydrogenation product still contains a minor amount of unconverted ester starting material. In one embodiment, the process includes a method for recovering fatty alcohol or alcohols from a fatty alcohol fraction containing a major molar amount of at least one fatty alcohol and a minor molar amount of at least one lower alkyl fatty acid ester. In another embodiment, there is provided a process for the production of fatty alcohols which comprises, in addition to other steps, hydrogenating a lower alkyl fatty acid ester to yield a mixture of a lower alkanol, a fatty alcohol fraction and a minor amount of unreacted lower alkyl fatty acid ester.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: August 11, 1992
    Assignee: Davy McKee (London) Limited
    Inventors: Martyn Wilmott, George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
  • Patent number: 5093535
    Abstract: A liquid phase catalytic hydrogenation process is described in which an organic feedstock, such as an aldehyde containing from 2 to about 20 carbon atoms, is contracted with hydrogen in the presence of a solid hydrogenation catalyst under hydrogenation conditions to produce a hydrogenation product, such as the corresponding alcohol containing from 2 to about 20 carbon atoms, which process comprises passing a feed solution of the organic feedstock in an inert diluent therefor downwardly in co-current with a hydrogen-containing gas through a hydrogenation zone containing a bed of a particulate hydrogenation catalyst whose particles substantially all lie in the range of from about 1.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: March 3, 1992
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, Alan J. Dennis
  • Patent number: 5053551
    Abstract: Continuous process for hydroformylation of olefins containing, typically, from 6 to 20 carbon atoms to produce the corresponding aldehydes. The rate of formation of high boiling aldehyde condensation products is minimized by use of a high boiling inert solvent whose boiling point, at the pressure prevailing in the product recovery zone, lies intermediate between that of the highest boiling aldehyde product produced in the hydroformylation reaction and that of the ligand, as well as by maintaining the concentration of product aldehyde at or below a predetermined minor amount. In this way the length of a production run can be significantly extended before it becomes necessary to shut down the plant due to accumulation of high boiling aldehyde condensation products.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: October 1, 1991
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, Alan J. Dennis
  • Patent number: 4960960
    Abstract: Hydrogen is supplied first to a last hydrogenation zone, and gases recovered from the last hydrogenation zone are passed to the first hydrogenation zone of a continuous multi-zone liquid phase process for hydrogenating an organic compound to a corresponding hydrogenation product. The organic compound, with a suitable diluent or recycle hydrogenation product, flows successively through the zones beginning with the first and ending with the last hydrogenation zone to undergo hydrogenation with the hydrogenation product being recovered from the last hydrogenation zone.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: October 2, 1990
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, John R. Hensman
  • Patent number: 4919765
    Abstract: Tetrahydrofuran is recovered by a two stage distillation procedure from a crude hydrogenation product resulting from vapor phase hydrogenation of diethyl maleate and containing water, ethanol and a minor amount of n-butanol, and possibly also dissolved hydrogen, in addition to butane-1,4-diol, gamma-butyrolactone and "heavies" such as diethyl ethoxysuccinate. In the first distillation stage, conveniently operated substantially at atmospheric pressure, ethanol, water, and tetrahydrofuran are recovered as overhead product, are condensed to separate the condensible components from a hydrogen stream which can be vented, and then redistilled in the presence of a molar excess of a hydroxylic solvent containing at least two hydroxyl groups, such as butane-1,4-diol, in a second distillation zone.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: April 24, 1990
    Assignee: Davy McKee (London) Limited
    Inventors: Peter R. Wilkes, John Scarlett, George E. Harrison
  • Patent number: 4792636
    Abstract: A process is provided for the recovery of an optionally substituted C.sub.7 to C.sub.17 aldehyde from a liquid hydroformylation product medium obtained by rhodium catalyzed hydroformylation of an optionally substituted C.sub.6 to C.sub.16 olefin which contains (i) a rhodium complex hydroformylation catalyst containing rhodium in complex combination with carbon monoxide and with a ligand, (ii) excess ligand, (iii) at least one optionally substituted C.sub.7 to C.sub.17 aldehyde, and (iv) aldehyde condensation products, which process comprises:(a) degassing said liquid hydroformylation medium;(b) passing the degassed liquid hydroformylation medium through an evaporation zone maintained under temperature and pressure conditions conducive to evaporation of said at least one C.sub.7 to C.sub.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: December 20, 1988
    Assignee: Davy McKee (London) Limited
    Inventors: John R. Hensman, Andrew J. Roberts, George E. Harrison
  • Patent number: 4767869
    Abstract: A process is described for the production of substantially pure gamma-butyrolactone from a feed mixture containing a major amount of gamma-butyrolactone and a minor amount of diethyl succinate which comprises fractionally distilling the mixture in a fractionation zone in the presence of added diethyl maleate and recovering from the fractionation zone an overhead vaporous product comprising gamma-butyrolactone which is substantially free from diethyl succinate and a liquid bottom product comprising diethyl maleate and diethyl succinate in admixture one with another. This procedure can be used to separate a gamma-butyrolactone rich fraction obtained by distillation in one or more stages of a crude reaction product obtained by hydrogenation of a C.sub.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: August 30, 1988
    Assignee: Davy McKee Limited
    Inventors: George E. Harrison, Norman Harris
  • Patent number: 4567306
    Abstract: A continuous hydroformylation process for the production of an aldehyde by hydroformylation of an olefin comprises:providing a hydroformylation zone containing a charge of a liquid reaction medium having dissolved therein (a) a complex rhodium hydroformylation catalyst comprising rhodium in complex combination with carbon monoxide and with a cyclic phosphite having a phosphorus atom linked to three oxygen atoms at least two of which form together with the phosphorus atom part of a ring and (b) a ligand stabilizing amount of a tertiary amine;supplying said olefin to the hydroformylation zone;maintaining temperature and pressure conditions in the hydroformylation zone conducive to hydroformylation of the olefin;supplying make-up hydrogen and carbon monoxide to the hydroformylation zone; andrecovering from the liquid hydroformylation medium a hydroformylation product comprising at least one aldehyde.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: January 28, 1986
    Assignee: Davy Mckee (London) Limited
    Inventors: Alan J. Dennis, George E. Harrison, James P. Wyber
  • Patent number: 4503275
    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.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: March 5, 1985
    Assignee: Davy McKee (London) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4496768
    Abstract: A continuous process for the production an aldehyde by hydroformylation of an optionally substituted alpha-olefin comprises:providing a hydroformylation zone containing a charge of a liquid reaction medium having dissolved therein a complex rhodium hydroformylation catalyst comprising rhodium in complex combination with carbon monoxide and with a cyclic phosphite having a bridgehead phosphorus atom linked to three oxygen atoms at least two of which form together with the bridgehead phosphorus atom part of a ring;supplying said alpha-olefin to the hydroformylation zone;maintaining temperature and pressure conditions in the hydroformylation zone conducive to hydroformylation of the alpha-olefin;supplying make-up hydrogen and carbon monoxide to the hydroformylation zone; andrecovering from the liquid hydroformylation medium a hydroformylation product comprising at least one aldehyde.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: January 29, 1985
    Assignee: Davy McKee Limited
    Inventors: Alan J. Dennis, George E. Harrison, James P. Wyber
  • Patent number: 4496769
    Abstract: A process for the production of an aldehyde by hydroformylation of an olefin comprises:providing a hydroformylation zone containing a charge of a liquid reaction medium having dissolved therein a complex rhodium hydroformylation catalyst comprising rhodium in complex combination with carbon monoxide and with an organic phosphite ligand of the general formula:(RO).sub.3 P (I)in which each R represents an optionally substituted hydrocarbyl radical;supplying said olefin to the hydroformylation zone;maintaining temperature and pressure conditions in the hydroformylation zone conducive to hydroformylation of the olefin;supplying make-up hydrogen and carbon monoxide to the hydroformylation zone;recovering from the liquid hydroformylation medium a hydroformylation product comprising at least one aldehyde; andsupplying make-up phosphite ligand to the hydroformylation zone at a rate sufficient to maintain a predetermined level of free phosphite ligand in the hydroformylation medium.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: January 29, 1985
    Assignee: Davy McKee (London) Limited
    Inventors: Alan J. Dennis, George E. Harrison, James P. Wyber
  • Patent number: 4482749
    Abstract: A process for the production of a non-linear aldehyde by hydroformylation of an optionally substituted internal olefin comprises:providing a hydroformylation zone containing a charge of a liquid reaction medium having dissolved therein a complex rhodium hydroformylation catalyst comprising rhodium in complex combination with carbon monoxide and with a cyclic phosphite having a bridgehead phosphorus atom linked to three oxygen atoms at least two of which form together with the bridgehead phosphorus atom part of a ring;supplying said internal olefin to the hydroformylation zone;maintaining temperature and pressure conditions in the hydroformylation zone conducive to hydroformylation of the internal olefin;supplying make-up hydrogen and carbon monoxide to the hydroformylation zone; andrecovering from the liquid hydroformylation medium a hydroformylation product comprising at least one non-linear aldehyde.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: November 13, 1984
    Assignee: Davy McKee (London) Limited
    Inventors: Alan J. Dennis, George E. Harrison, James P. Wyber
  • 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: 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