Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
  • Patent number: 5457240
    Abstract: A method for starting a preformer reactor disposed within a hydroformylation system which comprises an oxo reactor, a stripper reactor and a preformer reactor, wherein the bottoms from the stripper reactor comprise at least a water soluble cobaltous salt and wherein the overhead from the stripper reactor comprises entrained volatile cobalt compounds, wherein at least a portion of the entrained volatile cobalt compounds from the stripper reactor are recycled to the preformer reactor to act an initiator in the conversion of the cobaltous salt to cobalt carbonyl.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: October 10, 1995
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Stephen W. Beadle, Claude A. Poulin
  • Patent number: 5434311
    Abstract: In hydroformylation comprising allowing an ethylenically unsaturated compound to react with carbon monoxide and hydrogen in the presence of a catalyst to convert it into a corresponding aldehyde, the catalyst is a rhodium-containing catalyst comprising;(a) a rhodium compound;(b) an organic phosphorus compound having at least one tertiary amine residual group and at least one tertiary phosphorus residual group, having the ability of coordination to said rhodium compound; and optionally(c) an acidic compound with which at least part of the tertiary amine residual group of the organic phosphorus compound is converted into ammonium ions.
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: July 18, 1995
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiro Omatsu, Yasuo Tokitoh
  • Patent number: 5434318
    Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are reactivated or regenerated by treatment with a mixture of an aqueous organic acid solution and an alcohol at a temperature of about 120.degree. C. to 170.degree. C. and a pressure of about 13.78 MPa to 31.00 MPa for about 2 to 50 hours.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: July 18, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Ronald R. Hill, Patricia B. Roussel
  • Patent number: 5414138
    Abstract: A process for producing 2-formyl-1,4-butanediol comprises effecting reaction of 2-butene-1,4-diol with hydrogen and carbon monoxide in the presence of:(a) a rhodium compound,(b) a tris(substituted aryl) phosphite having an electronic parameter, .nu.-value, of 2,080 to 2,090 cm.sup.-1 and a steric parameter, .theta.-value, of 135.degree. to 190.degree. and being represented by the formula P(OR).sub.3wherein each of R's, which may be the same or different, represents a substituted aryl group having at least 7 carbon atoms, and(c) a bis (diphenylphosphino) alkane represented by the formula Ph.sub.2 P-(CH.sub.2)n-PPh.sub.2 where n n is an integer of 2 to 6, andat a temperature of not more than 80.degree. C.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: May 9, 1995
    Assignee: Kuraray Company Ltd.
    Inventors: Toshihiro Omatsu, Yasuo Tokitoh
  • Patent number: 5410090
    Abstract: A method for removing cobalt values from the crude product of a cobalt-catalyzed hydroformylation reaction by the application of an airless cobalt demetalling step upstream of the stripping step of a Cobalt Flash hydroformylation catalyst recovery process for C.sub.4 to C.sub.14 olefins, whereby no oxygen is required to oxidize cobalt carbonyls to their cobaltous form. This airless demetalling step may also be used downstream of the stripping step in the case of C.sub.7 to C.sub.20 olefins to remove carbonyls from a water soluble cobaltous salt and carbon carbonyl stream which is taken as bottoms from the stripper reactor.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: April 25, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Stephen W. Beadle, William H. Summerlin, Eddy T. A. Van Driessche
  • Patent number: 5410091
    Abstract: An improved process for the hydroformylation of olefins with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst in a continuous tubular reactor, the improvement comprising:a. employing an rhodium hydroformylation catalyst;b. maintaining the reaction temperature at less than about 145.degree. C.; andc. maintaining the pressure at less than 450 psig and the partial pressure therein attributable to carbon monoxide no greater than about 90% of the total pressure;whereby the hydroformylated olefin product is rich in normal aldehydes.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: April 25, 1995
    Assignee: Quimica Oxal C.A.
    Inventor: Charles S. Nall
  • Patent number: 5406006
    Abstract: Carbonaceous preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are activated or regenerated by treatment with an aqueous cobalt salt solution in the presence of a light alcohol having from about 4 to 7 carbon atoms and syn gas prior to exposure to or processing with any other organic stream at a temperature of about 120.degree. C. to 190.degree. C. and a pressure of about 13 MPa to 32 MPa for about 2 to 50 hours.
    Type: Grant
    Filed: May 24, 1994
    Date of Patent: April 11, 1995
    Assignee: Exxon Chemical Patents Inc
    Inventors: Ronald R. Hill, Patricia B. Roussel
  • Patent number: 5395979
    Abstract: A catalyst for use in hydroformylation of olefins which comprises a Group VIII noble metal complexed with a phosphine ligand having at least one alkyl or aryl group bonded thereto, such as tris-4-propylphenyl phosphines and tris-4-octylphenyl phosphines. These and other triphenylphosphine catalysts can be separated from a crude reaction product of a noble metal-catalyzed hydroformylation reaction by contacting the crude reaction product with a dense polymeric, nonpolar membrane, preferably nonpolar polyolefin membranes.
    Type: Grant
    Filed: February 25, 1993
    Date of Patent: March 7, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Harry W. Deckman, Edward Kantner, Joel R. Livingston, Jr., Michael G. Matturro, Edmund J. Mozeleski
  • Patent number: 5387719
    Abstract: A process for the preparation of aldehydes by hydroformylation of olefins having more than 7 carbon atoms, comprising hydroformylation by means of a rhodium catalyst dissolved homogeneously in the reaction medium, removal of the rhodium catalyst from the hydroformylation reaction product, and recycling of the rhodium separated off from the hydroformylation product into the hydroformylation step, in which the rhodium catalyst is extracted from the hydroformylation product into the aqueous phase by means of an aqueous solution of a nitrogen-containing complexing agent from the group comprising of sulfonated pyridines, sulfonated quinolines, substituted or unsubstituted, sulfonated or sulfonated substituent-carrying 2,2'-bipyridines, 1,10-phenanthrolines, 2,2'-biquinolines, 2,2',6',2"-terpyridines and porphines, and/or from the group comprising of carboxylated pyridines, carboxylated quinolines, substituted or unsubstituted, carboxylated or carboxylated substituent-carrying 2,2'-bipyridines, 1,10-phenanthrolines
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: February 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Michael Roeper, Rocco Paciello
  • Patent number: 5382701
    Abstract: A method for producing a potassium paradiphenyl phosphino sulfonate ligand which comprises reacting potassium diphenyl phosphide with a lithium salt of para-chloro benzenesulfonic acid in the presence of tetrahydrofuran at elevated temperatures.
    Type: Grant
    Filed: November 18, 1993
    Date of Patent: January 17, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Elena N. Suciu, Joel R. Livingston, Jr., Edmund J. Mozeleski
  • Patent number: 5367106
    Abstract: In a primary process for hydroformylating olefins in the presence of a rhodium-containing catalyst solution to produce aldehydes and a gaseous effluent comprising unreacted olefin is vented, the improvement which comprises employing the effluent as a reactant feed for a coupled secondary hydroformylation process conducted jointly therewith in which the catalyst solution is cycled back and forth between the primary and secondary hydroformylation processes.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: November 22, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry D. Unruh, Wendell L. Pieper, Milo C. Pass
  • Patent number: 5367107
    Abstract: The hydroformylation of olefins in liquid phase in the presence of an aqueous solution containing water-soluble rhodium-phosphine complex compounds as catalysts and salts of quaternary phosphonium compounds as solubilizers.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: November 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Peter Lappe
  • Patent number: 5364970
    Abstract: A process for the hydroformylation of .alpha.-substituted, .alpha.-.beta.-unsaturated carbonyl compounds in the presence of a catalyst system based ona) a source of rhodium cations andb) a source of ligands of the formula MR.sub.1 R.sub.2 R.sub.3 wherein M represents a phosphorus, arsenic or antimony atom and R.sub.1, R.sub.2, and R.sub.3 independently represent substituted or non-substituted hydrocarbyl groups, together containing not more than 24 carbon atoms. At least one of R.sub.1, R.sub.2, and R.sub.3 is linked to M via an aliphatic carbon atom. The process is selective for the generation of alpha reaction products.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: November 15, 1994
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Eric Kragtwijk
  • Patent number: 5362823
    Abstract: In a transition metal catalyst system, the improvement comprising including in the catalyst system an autoacceleration inhibitor, which (i) at about the temperature at which the catalyst system autoaccelerates, decomposes into a poison for the catalyst system; (ii) is present in the catalyst system in an amount sufficient to provide the quantity of poison required to inhibit the autoacceleration of the catalyst system at the autoacceleration temperature; and (iii) is either essentially inert at the normal operating temperature of the catalyst system or will cause substantially less inhibition of the catalyst system at the normal operating temperature than at the autoacceleration temperature.
    Type: Grant
    Filed: March 6, 1990
    Date of Patent: November 8, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Frederick J. Karol, Kao Sun-Chueh, James S. Drage
  • Patent number: 5362917
    Abstract: A method for controlling a hydroformylation reaction for producing an aldehyde by subjecting an olefin, a feed oxo gas containing hydrogen and carbon monoxide, and a recycled gas withdrawn from a reactor and returned to the reactor, to a hydroformylation reaction in the reactor in the presence of a catalyst, which comprises:setting out a target value for the partial pressure of carbon monoxide in the reaction system to control the hydroformylation reaction;detecting the partial pressure of carbon monoxide corresponding to the target value; andcomparing the detected partial pressure of carbon monoxide with the target value to adjust a flow rate of a discharged gas from the reactor; orcomparing the detected partial pressure of carbon monoxide with the target value to adjust a flow rate of the feed oxo gas.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: November 8, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Morimasa Ogawa, Genichi Emoto, Akio Ueda, Takao Kibayashi, Keitaro Nakata, Tsuneo Inoue
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5354908
    Abstract: A method for absorbing cobalt within an olefinic feedstock which comprises the steps of introducing a volatile cobalt compound and an olefinic feedstock into an absorber to form a cobalt-containing olefin mixture, withdrawing the cobalt-containing olefin mixture from the absorber, introducing at least a portion of the cobalt-containing olefin mixture into a reactor, wherein a substantial portion of the volatile cobalt compound entrained within the cobalt-containing olefin mixture decomposes to its non-volatile cobalt compound species, and recycling this mixture back to the absorber so that it can be used to further absorb volatile cobalt such that a more concentrated cobalt-containing olefin solution is formed.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: October 11, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Kirk C. Nadler
  • Patent number: 5344993
    Abstract: This invention relates to a process for making 3-hydroxyaldehydes having 4 or more carbon atoms by intimately contacting(a) 1,2-epoxides having 3 or more carbon numbers,(b) ditertiary phosphine-modified cobalt carbonyl catalyst, said phosphine being a hydrocarbylene-bis(monophosphabicyclononane) in which each phosphorus atom is joined to hydrocarbylene and is a member of a bridge linkage without being a bridgehead atom and which hydrocarbylene-bis(monophosphabicyclononane) has 11 to 80 carbon atoms, 5 to 12 carbon atoms thereof together with a phosphorus atom being members of each of the two bicyclic skeletal structures,(c) carbon monoxide, and(d) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6, in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C. and a pressure of from about 50 psi to about 10,000 psi.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: September 6, 1994
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Juan P. Arhancet
  • Patent number: 5344988
    Abstract: Disclosed are bis-phosphine compounds having the general formula ##STR1## wherein: each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is an arylene radical wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR2## constitutes a 5-membered ring; each of A.sup.5 and A.sup.6 is an arylene radical wherein A.sup.5 and A.sup.6 are bonded to each other and to residues R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 by ring carbon atoms and R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 are connected to each other through a chain of 4 carbon atoms; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or a hydrocarbyl radical containing up to about 8 carbon atoms.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: September 6, 1994
    Assignee: Eastman Chemical Company
    Inventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jeffrey J. Vanderbilt
  • Patent number: 5321168
    Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are activated or regenerated by treatment with H.sub.2 O at 120.degree. to 170.degree. C., 13.78 MPa (2,000 psig) to 31.00 MPa (4,500 psig) for 2-50 hours.
    Type: Grant
    Filed: September 16, 1993
    Date of Patent: June 14, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Patricia B. Roussel, William H. Summerlin
  • Patent number: 5312996
    Abstract: This invention relates to a hydroformylation process for producing a 1,6-hexanedial which comprises reacting a butadiene with hydrogen and carbon monoxide in the presence of a catalytic amount of rhodium complexed with certain poly-phosphite ligands to achieve high conversions of the butadiene to the 1,6-hexanedial.
    Type: Grant
    Filed: May 20, 1993
    Date of Patent: May 17, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5298669
    Abstract: A method for separating a noble metal catalyst from a crude reaction product of a noble metal-catalyzed hydroformylation reaction which comprises: (a) contacting the crude reaction product under perstraction conditions with a membrane capable of allowing a substantial portion of unreacted olefin feed and hydroformylation reaction product to pass therethrough as permeate while retaining a substantial portion of the catalyst as retentate; (b) removing the permeate by sweeping it away from the membrane by means of a sweep stream which is the same as the olefin feed used in the hydroformylation reaction; and (c) retaining the catalyst as retentate.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: March 29, 1994
    Assignee: Exxon Chemical Patent Inc.
    Inventors: Francis J. Healy, Joel R. Livingston, Edmund J. Mozeleski, John G. Stevens
  • Patent number: 5288918
    Abstract: An improved rhodium-organophosphite complex catalyzed hydroformylation process, the improvement comprising carrying out said process in the presence of a catalytic activity enhancing additive said additive being selected from the class consisting of added water, a weakly acidic compound, or both added water and a weakly acidic compound.
    Type: Grant
    Filed: September 29, 1992
    Date of Patent: February 22, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John M. Maher, James E. Babin, Ernst Billig, David R. Bryant, Tak W. Leung
  • Patent number: 5260491
    Abstract: Cationic rhodium bis(dioxaphosphorus heterocycle) complexes of the formula: ##STR1## in which R is preferably ##STR2## or (CH.sub.2).sub.2-5, Y . . . Y is any backbone chain of 2-5 atoms, and L and L' are any stabilizing ligands, used in hydroformylation of olefins to obtain regioselectivity of branched aldehyde products. The formula of the catalyst may include substituents which do not interfere with the branched product regioselectivity of the catalyst as a whole. In the hydroformylation method the olefin is reacted with hydrogen and carbon monoxide in the presence of the catalyst at a temperature and pressure sufficient to permit the desired branched product regioselectivity.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: November 9, 1993
    Assignee: New York University
    Inventors: Donald J. Wink, Thomas J. Kwok
  • Patent number: 5237105
    Abstract: A method for removing cobalt values from the crude product of a cobalt-catalyzed hydroformylation reaction which utilizes the same equipment in two different operating sequences to accommodate olefinic feedstocks having a wide range of carbon numbers. Olefinic feedstocks having a carbon number in the range C.sub.4 -C.sub.14, more preferably C.sub.5 -C.sub.7, can be decobalted by the application of an acid-air cobalt demetalling step upstream of the stripping step of a Cobalt Flash hydroformylation catalyst recovery process; whereas C.sub.7 to C.sub.20 olefinic feedstocks, more preferably C.sub.8 -C.sub.14, can be decobalted by application of the acid-air cobalt demetalling step downstream of the stripping step.
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: August 17, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventor: William H. Summerlin
  • Patent number: 5237104
    Abstract: An olefin of a heavier molecular weight than the feed olefin in a hydroformylation reaction process is used as an absorbent for recovering hydro cobalt carbonyl stripped from an oxonation reactor product. The cobalt in the stripping gas is completely absorbed but light hydrocarbons, e.g., hydrocarbons having a carbon number of C.sub.7 or less, are only partially absorbed, thus permitting hydro cobalt carbonyl to be recycled to the oxonation reactor without a continuing concentration build up of light hydrocarbons, e.g., paraffins.
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: August 17, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventor: William H. Summerlin
  • Patent number: 5235113
    Abstract: A hydroformylation process for preparing a hydroformylated product by reacting an olefinic compound with hydrogen and carbon monoxide in the presence of a Group VIII metal catalyst, in the reaction of which there is present a phosphite compound having the formula (I), ##STR1## wherein R.sup.1 and R.sup.2 are respectively an aromatic hydrocarbon groups which may be the same or different and the aromatic hydrocarbon group has at least a hydrocarbon group on a carbon atom adjacent to a carbon atom bonded with an oxygen atom as a substituent; A.sup.1 is an n-valent organic group having an aliphatic hydrocarbon group, a cycloaliphatic hydrocarbon group or an aromatic hydrocarbon group bonded with an adjacent oxygen atom, which may respectively have a substituent; n is an integer of from 2 to 4; and the respective ##STR2## group may be the same or different.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: August 10, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Yuji Kawaragi, Masaki Takai, Tooru Ookoshi
  • Patent number: 5235112
    Abstract: A method for removing cobalt values from the crude product of a cobalt-catalyzed hydroformylation reaction wherein an overhead stripper-reactor reflux product is recycled to a location on the stripper-reactor which is capable of forming a stripping zone in the upper portion of the stripper-reactor and a reaction zone in the lower portion of the stripper-reactor.
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: August 10, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Kirk C. Nadler, Thomas R. Broussard, Joseph K. Pitre
  • Patent number: 5233093
    Abstract: An improved allyl alcohol hydroformylation process and catalyst are disclosed. The process uses a catalyst system comprising a Group VIII metal carbonyl complex catalyst, a trisubstituted phosphine, a neutral Group VIII(a) metal complex cocatalyst, and optionally, a diphosphinoalkane. The process uniquely gives an enhanced linear:branched aldehyde product ratio.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: August 3, 1993
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Rangasamy Pitchai, Anne M. Gaffney, Manish K. Nandi, Yuan-Zhang Han
  • Patent number: 5198589
    Abstract: A method of olefin hydroformylation is provided wherein an olefin reacts with a carbonyl catalyst and with reaction gases such as hydrogen and carbon monoxide in the presence of a supercritical reaction solvent, such as carbon dioxide. The invention provides higher yields of n-isomer product without the gas-liquid mixing rate limitation seen in conventional Oxo processes using liquid media.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: March 30, 1993
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Jerome W. Rathke, Robert J. Klingler
  • Patent number: 5180854
    Abstract: Process for the separation and recovery of aldehyde product from a non-aqueous hydroformylation reaction product composition comprising the aldehyde product, a rhodium-ionically charged phosphorus ligand complex, a free ionically charged phosphorus ligand and an organic solubilizing agent for said complex and said free ligand via phase separation using added water or both added water and an added non-polar hydrocarbon compounds.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: January 19, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anthony G. Abatjoglou, David R. Bryant, Ronald R. Peterson
  • Patent number: 5177228
    Abstract: Hydroformylation process, wherein an olefinic compound is reacted with hydrogen and carbon dioxide in the presence of a Group VIII precious metal complex catalyst containing an organic phosphorus compound as a ligand, the process being characterized by use of trialkyl phosphine, as the organic phosphorus compound, having the total carbon atom number of 27 or more in its alkyl groups.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: January 5, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Yuji Kawaragi, Masaki Takai
  • Patent number: 5136096
    Abstract: The bis-homotris compounds 4-amino-4-[1-(3-hydroxypropyl)]-1,7-heptanediol and 4-[1-(3-aminopropyl)]-4-[1-(3-hydroxypropyl)]-1, 7-heptanediol, and organic synthetic methods for their preparation are described. Unique multifunctional aminotriols, as well as their percursors, quaternary nitroalkanes are disclosed as building blocks for unimolecular micelles, as well as new series of cascade polymers. The quaternary nitro compounds which are disclosed allow the synthesis of a new aminotriol containing a quaternary carbon.
    Type: Grant
    Filed: March 26, 1991
    Date of Patent: August 4, 1992
    Assignee: University of South Florida
    Inventors: George R. Newkome, Charles N. Moorefield
  • Patent number: 5130107
    Abstract: Cobalt is recovered from the oil/water mixed reaction product of oxonation by increasing the carbon dioxide level in the reaction product and adjusting the temperature to enhance the carbon dioxide level in the oil water phase to promote the formation of cobalt carbonate which is allowed to settle and may be removed and/or recycled increasing cobalt utilization and reducing environmental problems.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: July 14, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Nicolaas A. De Munck, Mattheus D. Olijve, Raf Caers, Arie Van Vliet, Jean A. A. Hanin, Eddy Van Driessche
  • Patent number: 5118867
    Abstract: The preparation of aldehydes by hydroformylation of olefinically unsaturated compounds. The reaction is carried out in the presence of a catalyst system which contains rhodium and an ammonium salt of a sulfonated phosphorous acid triester which is soluble in organic media.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: June 2, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Bernhard Fell, Georgios Papadogianakis
  • Patent number: 5105018
    Abstract: A process for hydroformylation of an olefin, which comprises reacting an olefin with carbon monoxide and hydrogen in the presence of a rhodium catalyst having a trivalent organic phosphorus compound as a ligand, wherein the hydroformylation reaction is conducted by two stage reactor systems i.e., a first stage reactor system comprising a reactor or reactors having a mixing characteristic of the liquid phase being substantially of complete mixing type, and a second stage reactor system being a reaction system of a catalyst solution circulating type and comprising a reactor or reactors having a mixing characteristic of piston flow type wherein when the mixing characteristic of the liquid phase is represented by a diffusion model, a non-dimensional number U (hereafter referred to as a "flow mixing parameter") defined by the formula (I):U.tbd.uL/2E (I)wherein u is an average flow velocity (cm/sec), L is the length (cm) of the reaction layer, and E is an average diffusion coefficient (cm.sup.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Chihiro Miyazawa, Hiroshi Mikami
  • Patent number: 5091599
    Abstract: Cobalt is recovered from the oil/water mixed reaction product of an oxonation reaction by converting the cobalt in the oil/water product to carbonyls and absorption of the carbonyls in the residue obtained from the upgrading of the heavy fraction of a hydroformylation reaction.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: February 25, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Nicolaas A. De Munck, Mattheus D. Olijve
  • Patent number: 5087763
    Abstract: An improved liquid recycle rhodium-catalyzed hydroformylation process wherein the improvement comprises recovering unreacted olefin contained in a vent gas of the process and recycling said unreacted olefin to the hydroformylation reaction medium.
    Type: Grant
    Filed: November 9, 1990
    Date of Patent: February 11, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Kirk D. Sorensen
  • Patent number: 5082977
    Abstract: Olefins are reacted with carbon monoxide and hydrogen to produce aldehydes to the near exclusion of alcohols in the presence of a solid phase catalyst consisting essentially of one or more sulfided Group VIII metals.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: January 21, 1992
    Assignee: University of Akron
    Inventor: Steven S. C. Chaung
  • Patent number: 5071572
    Abstract: In the the oxo process for alcohol production the heavy component left after enriching and recycling is itself recycled to oxonation to give yield improvement.
    Type: Grant
    Filed: September 1, 1989
    Date of Patent: December 10, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Nicolaas A. De Munck
  • 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: 5041684
    Abstract: Olefinically unsaturated compounds are hydroformylated in an organic reaction medium with the aid of rhodium complex catalysts which are soluble in the reaction medium by performing the reaction in the presence of water-insoluble rhodium complex catalysts and also in the presence of arylthiols of the general formula IAr--SH Iwhere Ar is substituted or unsubstituted aryl.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: August 20, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Koeffer, Werner Bertleff, Michael Roeper
  • Patent number: 5012008
    Abstract: Normal aldehydes are produced in high selectivity by the vapor phase reaction of lower olefins with hydrogen and carbon monoxide in the presence of supported liquid phase catalysts at temperatures of 80.degree. C. to 100.degree. C. under pressures of 1 to 5 atmospheres.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: April 30, 1991
    Inventors: Russell S. Drago, Mark J. Barnes, Michael J. Naughton
  • Patent number: 5012006
    Abstract: 2,2-Dialkylpropionaldehydes I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.4 -alkyl, are prepared by hydroformylation of 1,1-dialkylethylenes II ##STR2## with cobalt carbonyl complexes, entailing (a) carrying out the reaction in the presence of water-containing solvents in which water is soluble or at least partially soluble, with the water content of the reaction mixture being from 0.1 to 20% by weight, or(b) carrying out the reaction in the presence of a lactone which can have one or more C.sub.1 -C.sub.4 -alkyl substituents, or of an aliphatic or cycloaliphatic sulfone.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: April 30, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Bertleff, Dieter Koeffer
  • Patent number: 5001274
    Abstract: An improved process for the rhodium-catalyzed hydroformylation of olefins to aldehydes is described. The improvement provides a means for recovering valuable components in gaseous streams by scrubbing the streams with a stripped or cooled catalyst solution.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: March 19, 1991
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Donald L. Bunning
  • Patent number: 4996366
    Abstract: Process for the catalytic hydroformylation of olefins in which an olefin is reacted with hydrogen and carbon monoxide, with the process being carried out by operating in a liquid, aqueous-organic reaction medium, in the presence of a water-soluble complex catalyst containing a metal active in the hydroformylation, wherein said aqueous-organic medium is in the form of a microemulsion consituted by an oil phase, an aqueous phase, a surfactant and a co-surfactant, with said oil phase constituting the external phase of said microemulsion, and said aqueous phase constituting the internal phase of said microemulsion.
    Type: Grant
    Filed: January 23, 1990
    Date of Patent: February 26, 1991
    Assignee: Eniricerche S.p.A
    Inventors: Laura Tinucci, Edoardo Platone
  • Patent number: 4978801
    Abstract: Aromatic aldehydes are more efficiently produced by reacting carbon monoxide/hydrogen admixture with an aromatic halide in the presence of a noble metal-based catalyst, a tertiary nitrogenous based and, if necessary, a noble metal complexing agent, e.g., a phosphine or phosphite, wherein the CO/H.sub.2 ratio is less than 1.
    Type: Grant
    Filed: April 28, 1987
    Date of Patent: December 18, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Norbert Bluthe, Robert Perron
  • Patent number: 4960949
    Abstract: The hydroformylation of olefins with rhodium complex catalysts is described. The catalysts employed comprise a rhodium complex with at least one bidentate ligand having a specified structure, ##STR1## Hydroformylation reactions at relatively low temperatures and pressure and yet with high rates of reaction and high selectivity to aldehyde product are obtained by the practice of the present invention.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: October 2, 1990
    Assignee: Eastman Kodak Company
    Inventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jeffrey J. Vanderbilt
  • Patent number: 4950798
    Abstract: A novel hydroformylation process for the conversion of olefins having up to about 20 carbon atoms to their corresponding aldehydes is provided herein involving the use of catalysts comprising chelates in which a ligand is chelated at a metal center to produce at least one heterocyclic ring with the central metal atom as part of the ring, i.e., platinum-group metal phosphinoalkylsilyl complexes with bis- or tris(phosphinoalkyl)silyl. Novel catalysts are also provided which are platinum-group metal complexes with bis- or tris(phosphinoalkyl)silyl ligands, which are synthesized by using novel bis(phosphinoalkyl)silanes or tris(phosphinoalkyl)silanes.
    Type: Grant
    Filed: December 14, 1988
    Date of Patent: August 21, 1990
    Assignee: University of Victoria
    Inventors: Stephen R. Stobart, Stephen L. Grundy, Frederick L. Joslin
  • Patent number: 4947003
    Abstract: A process for the hydroformylation of alkenes and other olefinically unsaturated reactants by reaction with carbon monoxide and hydrogen in the presence of a heterogeneous catalyst comprising a solid surface having immobilized thereon a solution of one or more rhodium complexes which is essentially immiscible with the organic reactant. Catalyst is subsequently recovered from the resulting hydroformylation product by one or more solid-liquid separation techniques.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: August 7, 1990
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Mark E. Davis, Juan P. Arhancet, Brian E. Hanson