Patents by Inventor Robert C. Michaelson

Robert C. Michaelson 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: 6303827
    Abstract: Alkyl aromatic compounds are converted to alkyl aromatic aldehydes by a carbonylation reaction. The carbonylation catalyst can be a high boiling point carbonylation catalyst which allows for the separation of the aldehyde product by selective volatilization. Alternatively, the carbonylation catalyst can be selected from perfluoroalkyl sulfonic acids having 2 to 18 carbon atoms, perfluoroether sulfonic acids having 2 to 18 carbon atoms, BF3(ROH)x wherein R represents CH3 or H and X is a number within the range of from 0.2 to 2, GaBr3, GaCl3, TaF5, NbF5, and NbBr5, with the proviso that when the catalyst is TaF5, NbF5, or NbBr5, then the reaction takes place in the absence of added HF. Preferably, all of the carbonylation reactions take place in the absence of added HF. The alkyl aromatic aldehydes can be oxidized to form an aromatic acid.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: October 16, 2001
    Assignee: ExxonMobil Chemicals Patents Inc.
    Inventors: Ramzi Yanni Saleh, Christopher L. Becker, Robert C. Michaelson, Richard H. Schlosberg
  • Patent number: 5565603
    Abstract: A process for making a dialkyl carbonate which comprises reacting urea with a first alcohol in a carbamate reactor at a temperature and pressure sufficient to convert said urea to an alkyl carbamate; and reacting the alkyl carbamate with a second alcohol in the presence of a dialkyl isocyanato alkoxy tin catalyst or derivatives in a carbonate reactor at a temperature and pressure sufficient to convert the alkyl carbamate to a dialkyl carbonate, wherein the molar ratio of alkyl carbamate to second alcohol is in the range between about 2:1 to about 10:1 and wherein dialkyl carbonate is present within the carbonate reactor in an amount between about 1 to about 3 weight %, based on total alkyl carbamate and second alcohol content, and wherein the second alcohol is either the same as or different from the first alcohol or a mixture of alcohols.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: October 15, 1996
    Inventors: Ramzi Y. Saleh, Robert C. Michaelson, Elena N. Suciu, Barbara Kuhlmann
  • Patent number: 5561094
    Abstract: A process for making a dialkyl carbonate which comprises reacting urea with a first alcohol in a carbamate reactor at a temperature and pressure sufficient to convert said urea to an alkyl carbamate; and reacting the alkyl carbamate with a second alcohol in the presence of a dialkyl isocyanato alkoxy tin catalyst or derivatives in a carbonate reactor at a temperature and pressure sufficient to convert the alkyl carbamate to a dialkyl carbonate, wherein the molar ratio of alkyl carbamate to second alcohol is in the range between about 2:1 to about 10:1 and wherein dialkyl carbonate is present within the carbonate reactor in an amount between about 1 to about 3 weight %, based on total alkyl carbamate and second alcohol content, and wherein the second alcohol is either the same as or different from the first alcohol or a mixture of alcohols.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: October 1, 1996
    Inventors: Ramzi Y. Saleh, Robert C. Michaelson, Elena N. Suciu, Barbara Kuhlmann
  • Patent number: 5545600
    Abstract: A process for making a catalyst product which comprises reacting dialkyltin oxide with an alcohol and the corresponding dialkyl carbonate at a temperature in the range between about 50.degree. to 200.degree. C. and at a pressure in the range between about 75 to 600 psi (0.52 to 4.14 MPa), wherein the catalyst product comprises dialkyltin dialkoxide in the range between about 90 to 100 mole % based on the tin species of the catalyst product. This process also forms effective catalyst product when the methanol is replaced with either a primary or secondary alcohol.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: August 13, 1996
    Inventors: George A. Knudsen, Elena N. Suciu, Robert C. Michaelson
  • Patent number: 5223464
    Abstract: A process for regenerating a catalyst which involves washing a catalyst with a liquid at a temperature within the range of about 50.degree. C. to about 70.degree. C. for a time sufficient to remove foulants thereby recovering catalyst activity. The wash liquid is preferably a member selected from the group consisting of ethers, alcohols and mixtures of ethers and alcohols wherein the ether is a tertiary alkyl ether, preferably selected from the group consisting of tertiary amyl methyl ether and methyl tertiary butyl ether, and wherein the alcohol is preferably selected from the group consisting of tertiary butyl alcohol and methanol. The catalyst is preferably a clay treated with an acid selected from the group consisting of hydrofluoric acid, hydrochloric acid and mixtures of hydrofluoric and hydrochloric acid, wherein the clay is preferably selected from the group consisting of montmorillonite, kaolinite, attapulgite, bentoninte and natural clay.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: June 29, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert C. Michaelson, Gustavo Cerri
  • Patent number: 5177290
    Abstract: The present invention is directed to a process for producing dienes which involves reacting a reaction mixture of tertiary alkyl ether and a source of oxygen over two functionally distinct catalysts under reaction conditions sufficient to produce high yields of the dienes with minimal recycle of the ether. The two functionally different catalysts are selected from a group of bifunctional catalysts having both oxidation sites and acidic sites and monofunctional acidic catalysts, such as bifunctional catalysts containing components selected from a group of oxides of vanadium, tungsten, molybdenum, copper, iron, chromium, and uranium and mixtures thereof; and monofuctional acid catalysts such as acid treated montmorillonite clays, and acid catalysts comprising an inorganic amorphous or substantially amorphous oxide material comprising the following components reacted therein:M.sup.1 /M.sup.2 /P/Owherein M.sup.1 is at least one Group IIIB element selected from the group consisting of Al, Ga, In and Tl; M.sup.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: January 5, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Ji-Yong Ryu, Robert C. Michaelson
  • Patent number: 5118871
    Abstract: A method for producing alkyl tertiary alkyl ether involves supplying a feed including isoolefins, alcohols, and dialkyl sulfides into a feed zone of a reactor; contacting the feed with a catalyst material in the reaction zone; and catalytically reacting the isooolefins and alcohols under conditions which favor forming resultant ether and inhibiting reaction of dialkyl sulfides with the catalyst material.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: June 2, 1992
    Assignee: Exxon Chemical Patents Inc
    Inventors: John J. Cikut, Robert C. Michaelson, Dan E. Hendriksen, Terry A. Fons, Di-Yi Ou, Daniel D. Rosenfeld
  • Patent number: 5113033
    Abstract: A catalyst system for codimerization of alpha-monoolefins and conjugated diolefins to yield 1,4-dienes. The catalyst system includes at least one ruthenium salt and at least one aluminum halide. Suitable aluminum halides include both alkyl aluminum halides and nonalkylated aluminum halides, as well as mixtures thereof.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: May 12, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Richard S. Myers, Daniel R. Mills, Robert C. Michaelson
  • Patent number: 5073663
    Abstract: A method for increasing the ratio of 2-methyl-2-butene (2MB2) to 2-methyl-1-butene (2MB1) in isoamylenes involves fractionating a feedstream containing tertiary amyl methyl ether (TAME) and isoamylenes including 2MB2 and 2MB1 in a ratio of about 2:1 to effect a separation between an overhead hydrocarbon fraction of isoamylenes including 2MB2 and 2MB1 in a ratio of about 1:1, a bottoms fraction including TAME, and a sidestream hydrocarbon fraction consisting essentially of isoamylenes including 2MB2 and 2MB1 in a ratio of about 6 to 12:1, recovering the sidestream hydrocarbon fraction, and recycling the overhead hydrocarbon fraction of isoamylenes to form a mixture which is subsequently reacted to form the feedstream. Prior to fractionation, the feedstream is formed by passing isoamylene, and optionally TAME, in a vapor phase over an ether cracking catalyst which isomerizes isoamylene and converts 2MB1 to 2MB2, i.e., the feedstream for fractionating, which contains 2MB2 and 2MB1 in a ratio of 2 to 5:1.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: December 17, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Gustavo Cerri, Robert C. Michaelson
  • Patent number: 5043518
    Abstract: A process for regenerating a catalyst which involves washing a catalyst with a liquid at a temperature within the range of about 50.degree. C. to about 70.degree. C. for a time sufficient to remove foulants thereby recovering catalyst activity. The wash liquid is preferably a member selected from the group consisting of ethers, alcohols and mixtures of ethers and alcohols wherein the ether is a tertiary alkyl ether, preferably selected from the group consisting of tertiary amyl methyl ether and methyl tertiary butyl ether, and wherein the alcohol is preferably selected from the group consisting of tertiary butyl alcohol and methanol. The catalyst is preferably a clay treated with an acid selected from the group consisting of hydrofluoric acid, hydrochloric acid and mixtures of hydrofluoric and hydrochlorica acid, wherein the clay is preferably selected from the group consisting of montmorillonite, kaolinite, attapulgite, bentonite and natural clay.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: August 27, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert C. Michaelson, Gustavo Cerri
  • Patent number: 4824969
    Abstract: A process for reacting in admixture, an olefin with oxygen, CO, and water, to form a cyclic alkylene carbonate, in the presence of a catalyst composition comprising a catalytically active osmium compound, copper containing co-catalyst I (e.g. CuBr.sub.2) and a co-catalyst II (e.g. pyridine) is disclosed.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: April 25, 1989
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard G. Austin, Robert C. Michaelson, Richard S. Myers
  • Patent number: 4714788
    Abstract: In a process for separating C.sup.4 to C.sup.7 tertiary mono-olefins(s) present in a C.sup.4 to C.sup.7 hydrocarbon mixture containing diolefins which comprises selectively reacting said tertiary mono-olefin mixture with a primary alcohol in the presence of an acid catalyst to convert it to tertiary ether(s), separating the tertiary ether(s) from the unreacted hydrocarbon mixture and containing said tertiary ether(s) in the presence of a catalyst to decompose it to tertiary olefin(s) and a primary alcohol, the improvement which comprises hydrogenating the tertiary ether(s) after it has been separated from the unreacted hydrocarbon mixture and prior to decomposition to saturate the unsaturated ether(s) formed from the diolefins present in the hydrocarbon mixture.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: December 22, 1987
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert C. Michaelson, Jeffrey S. Plotkin
  • Patent number: 4691073
    Abstract: High purity tertiary olefins are obtained in extremely high yields over a sustained period by cracking alkyl tert-alkyl ethers over clay catalysts which have been treated with HF and/or HC1. Preferably temperature are 100.degree.-250.degree. C., the surface area of the catalyst is above 40 M.sup.2 /gm and the cracking step is part of a process for recovering isobutylene or isoamylene from steam cracked streams.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: September 1, 1987
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Robert C. Michaelson
  • Patent number: 4533773
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an osmium oxide catalyst such as OsO.sub.4, a carboxylate salt co-catalyst, such as sodium acetate, and organic hydroperoxide oxidant is disclosed.
    Type: Grant
    Filed: March 22, 1984
    Date of Patent: August 6, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4533772
    Abstract: The process for hydroxylating olefins with oxygen in the presence of water, an osmium-halide (e.g., OsBr.sub.3) catalyst and transition metal containing co-catalyst (CuBr.sub.2) is disclosed.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: August 6, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4496778
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as pyridine is disclosed.
    Type: Grant
    Filed: October 3, 1983
    Date of Patent: January 29, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
  • Patent number: 4496779
    Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as 1,4-diazabicyclo [2.2.2.] octane is disclosed.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: January 29, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
  • Patent number: 4486613
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an oxidant selected from organic hydroperoxides, H.sub.2 O.sub.2, and oxygen and a catalyst composition comprising at least one osmium carbonyl catalyst, such as Os.sub.3 (CO).sub.12, and optionally at least one cocatalyst such as NaI, is disclosed.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: December 4, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
  • Patent number: 4482763
    Abstract: A process for hydroxylating olefins with an organic hydroperoxide and water in the presence of an osmium containing catalyst (e.g. OsO.sub.4) and an organic halogenated hydrocarbon co-catalyst (e.g., n-butyl iodide) is disclosed.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: November 13, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard G. Austin, Robert C. Michaelson
  • Patent number: 4413151
    Abstract: A process for hydroxylating olefins using a supported osmium catalyst such as Os.sub.3 (CO).sub.12 adsorbed on a support, such as MgO, and optionally in conjunction with a co-catalyst such as NaI, is disclosed.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: November 1, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White