Patents Represented by Attorney Carl G. Ries
  • Patent number: 5401889
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solution of tertiary butyl hydroperoxide in a cosolvent mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: March 28, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: John R. Sanderson, Mark A. Mueller, Yu-Hwa E. Sheu
  • Patent number: 5399794
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina having gold-promoted palladium deposited thereon and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: March 21, 1995
    Assignee: Texaco Chemical Inc.
    Inventor: John R. Sanderson
  • Patent number: 5395982
    Abstract: An impure methyl tertiary butyl ether product contaminated with isobutylene, methanol and water is purified by continuous counter-current contact with water and isobutylene in a counter-current contact extraction tower to provide an overhead extract comprising isobutylene, methyl tertiary butyl ether and water and a raffinate comprising methanol, water and a minor amount of methyl tertiary butyl ether, the overhead raffinate being separated in a methyl tertiary butyl ether purification distillation zone into a lighter distillation fraction comprising isobutylene and water and a heavier distillation fraction consisting essentially of methyl tertiary butyl ether, the lighter distillation fraction being decanted to remove water and to provide a distillate isobutylene fraction that is charged to a surge drum from which isobutylene is returned to the contact tower.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: March 7, 1995
    Assignee: Texaco Chemical Company
    Inventors: John R. Cassata, Stuart J. Parker, Rei-Yu J. Hwan, Catherine J. Conkwright
  • Patent number: 5391826
    Abstract: Diamidopolyamines are prepared by reacting glutamic acid with two moles, per mole of glutamic acid, of a defined class of diamines, including oxyethyelene diamines, oxypropylenediamines, oxyethylene/propylene diamines, oxypropylene triamines, 1,2-diaminocyclohexane and isophorone diamine, whereby each of the carboxyl groups of the glutamic acid will react with an amine group of the amine reactant to thereby provide primary amine terminated amidopolyamines containing, internally, the unreacted primary amine group of the glutamic acid.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: February 21, 1995
    Assignee: Huntsman Corporation
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5364988
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina having chromium deposited thereon and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: November 15, 1994
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Roger G. Duranleau
  • Patent number: 5359130
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina having palladium and platinum deposited thereon and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: October 25, 1994
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Roger G. Duranleau, John F. Knifton
  • Patent number: 5354431
    Abstract: Crude propylene oxide is purified by a distillation process wherein it is (a) extractively distilled in a first column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a first overhead fraction comprising propylene oxide, C.sub.5 -C.sub.7 hydrocarbons, methanol, water and oxygen-containing impurities, (b) wherein the first overhead fraction is separated in a plurality of intermediate distillation columns to provide an intermediate propylene oxide overhead fraction consisting essentially of propylene oxide and water, and (c) the intermediate propylene oxide overhead fraction is charged to a final distillation column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a final overhead fraction consisting essentially of propylene oxide.
    Type: Grant
    Filed: September 23, 1993
    Date of Patent: October 11, 1994
    Assignee: Texaco Chemical Company
    Inventor: Mark E. Taylor
  • Patent number: 5354912
    Abstract: An isobutylene feed mixture comprising MTBE, isobutylene and methanol is passed through an isobutylene conversion zone to form an isobutylene conversion product comprising unreacted methanol, unreacted isobutylene, dimethyl ether, MTBE and water, then charged to a countercurrent methanol extraction zone and contacting with water to provide an overhead raffinate comprising isobutylene, MTBE and water, and an extract comprising methanol, water, MTBE, isobutylene and dimethyl ether;the extract is distilled to provide a vaporized overhead fraction comprising MTBE, isobutylene, methanol, and dimethyl ether;the vaporized overhead fraction is partially condensed and from about 5 to 10 wt. % of the mixed phase condensate is vented to thereby provide a liquid condensate that is substantially free from dissolved dimethyl ether, and the condensate is recycled to the methanol extraction zone.
    Type: Grant
    Filed: June 1, 1993
    Date of Patent: October 11, 1994
    Assignee: Texaco Chemical Company
    Inventors: Rei-Yu J. Hwan, Charles J. Kruse
  • Patent number: 5354917
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of alumina or carbon having rhodium deposited thereon and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: October 11, 1994
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Roger G. Duranleau, John F. Knifton
  • Patent number: 5354430
    Abstract: Contaminants are removed from impure propylene oxide by fractionating in a first column to remove overhead essentially all of the pentenes and pentanes and most of the oxygen-containing impurities to provide a partially purified first propylene oxide bottoms fraction, extractively distilling the first bottoms fraction in a second extractive column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a second overhead fraction comprising propylene oxide, hexenes, hexanes, water, residual quantities of pentenes and pentanes and oxygen-containing impurities, extractively distilling the second overhead fraction in a third column using a C.sub.6 to C.sub.10 alkane hydrocarbon extractive distillation agent to form a third bottoms fraction comprising the extractive distillation agent, propylene oxide, hexenes, hexanes, residual quantities of pentenes and pentanes and water, and extractively distilling said third bottoms fraction in a fourth column using a C.sub.6 to C.sub.
    Type: Grant
    Filed: October 26, 1993
    Date of Patent: October 11, 1994
    Assignee: Texaco Chemical Company
    Inventors: William K. Culbreth, III, Yu-Hwa E. Sheu, David G. Pottratz
  • Patent number: 5354925
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of lead oxide supported on alumina and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: October 11, 1994
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Roger G. Duranleau
  • Patent number: 5349072
    Abstract: In reacting tertiary butyl hydroperoxide in solution in tertiary butyl alcohol with propylene to produce propylene oxide and tertiary butyl alcohol in a reactor system comprising a first isothermal segment and a second adiabatic segment about 60 to 80 wt % of the tertiary butyl hydroperoxide is converted in the isothermal segment to provide an intermediate reaction mixture, a recycle stream comprising about 25 to 100 wt. % of the combined weight of the propylene and the tertiary butyl alcohol solution is removed from the intermediate reaction mixture and recycled to the first isothermal segment and the remainder of the intermediate reaction mixture is passed through the adiabatic segment where an additional 20 to 40 wt. % of the tertiary butyl hydroperoxide is converted.
    Type: Grant
    Filed: July 6, 1993
    Date of Patent: September 20, 1994
    Assignee: Texaco Chemical Company
    Inventors: Kyle L. Preston, Chung-Nan T. Wu, Mark E. Taylor, Mark A. Mueller
  • Patent number: 5345009
    Abstract: A method for conjointly preparing tertiary butyl alcohol and ditertiary butyl peroxide wherein a solution of a tertiary butyl hydroperoxide feedstock in tertiary butyl alcohol is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of palladium supported on pelleted carbon, and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol and ditertiary butyl peroxide.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: September 6, 1994
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John F. Knifton
  • Patent number: 5340446
    Abstract: An extractive distillation agent consisting essentially of a mixture of triethylene glycol with a lower boiling cosolvent selected from the group consisting of 2-methyl-2,4-pentanediol, tertiary butyl alcohol and ethylene glycol is fed to an extractive distillation column used for the distillation of propylene oxide contaminated with water, acetone and methanol to obtain an overhead distillate fraction consisting of essentially anhydrous propylene oxide contaminated with reduced quantities of acetone and methanol, and a heavier bottoms distillation fraction containing substantially all of the extractive distillation agent, water and acetone and some of the methanol introduced into the distillation column.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: August 23, 1994
    Assignee: Texaco Chemical Company
    Inventors: William P. Nelson, William A. Smith
  • Patent number: 5286884
    Abstract: A method and apparatus for continuously catalytically exothermally reacting propylene with tertiary butyl hydroperoxide in a reaction mixture stream comprising a tertiary butyl alcohol solution of catalyst, reacting propylene, reacting tertiary butyl hydroperoxide, propylene oxide and reaction by-products by thermosyphonically circulating the reaction mixture stream around a thermosyphonic reactor loop; continuously removing heat from the circulating stream in a downflow heat exchange zone in the reactor and continuously passing the circulating stream of reaction mixture through an adiabatic zone such as an upflow reaction zone of progressively increasing temperature while withdrawing or displacing a product stream in an amount sufficient to maintain a predetermined volume of reaction mixture in the reactor and whereby the density of the reaction mixture in the heat exchange zone will be greater than the density of the reaction mixture in the adiabatic zone whereby continuous thermosyphonic circulation can be
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: February 15, 1994
    Assignee: Texaco Chemical Company
    Inventors: Roderick S. Cowley, Darrell D. Kinzler
  • Patent number: 5262017
    Abstract: Impure propylene oxide is purified by a distillation process wherein it is (a) extractively distilled in a first column using a C.sub.2 to C.sub.6 alkylene glycol extractive distillation agent to form a first overhead fraction comprising propylene oxide, C.sub.5 -C.sub.7 hydrocarbons methanol, water and oxygen-containing impurities, (b) wherein the first overhead fraction is separated in a second column into a second overhead fraction comprising most of the pentanes, pentenes and oxygen-containing impurities and a partially purified propylene oxide bottoms fraction comprising propylene oxide, hexenes, hexanes, and only residual quantities of pentenes and pentanes, (c) wherein the partially purified bottoms fraction is extracting distilled in a third column using a C.sub.7 -C.sub.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: November 16, 1993
    Assignee: Texaco Chemical Company
    Inventors: Robert A. Meyer, William A. Smith, Mark A. Mueller, Gregory B. Demoll
  • Patent number: 5254759
    Abstract: Tertiary butyl alcohol contaminated with residual amounts of peroxide contaminants such as tertiary butyl hydroperoxide, ditertiary butyl peroxide, allyl tertiary butyl peroxide, etc., (which may be prepared, for example, by catalytically reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and tertiary butyl alcohol) can be effectively catalytically treated under mild conversion conditions including a temperature of about 100.degree. to about 300.degree. C. with a catalyst comprising ferrous oxide to substantially completely decompose the peroxide contaminants to thereby provide a treated tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: October 19, 1993
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John F. Knifton, Melvin E. Stockton
  • Patent number: 5243100
    Abstract: A method for preparing tertiary butyl alcohol wherein a solution of a tertiary butyl hydroperoxide feedstock comprising a solution of tertiary butyl hydroperoxide in tertiary butyl alcohol is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of a mixture of a soluble cycloalkenyl iron compound with a soluble ruthenium compound, and is brought into contact with the catalyst in liquid phase with agitation under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: September 7, 1993
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John F. Knifton
  • Patent number: 5243101
    Abstract: Motor-fuel tertiary butyl alcohol contaminated with residual amounts of tertiary butyl hydroperoxide, ditertiary butyl peroxide and allyl tertiary butyl peroxide (which is prepared, for example, by reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and a motor fuel grade tertiary butyl alcohol reaction product) can be effectively catalytically treated under mild conversion conditions including a temperature of about 160.degree. to 200.degree. C. with a catalyst consisting essentially of vitrified silica to substantially completely decompose the peroxide contaminants to thereby provide a treated tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: September 7, 1993
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Yu-Hwa E. Sheu, Michael W. Peters
  • Patent number: 5243091
    Abstract: A method for the preparation of methyl tertiary butyl ether is provided wherein a mixture of methanol and substantially peroxides-free tertiary butyl alcohol are catalytically reacted to form a reaction product that is separated into a first lighter distillation fraction comprising isobutylene, methanol and methyl tertiary butyl ether and a second heavier distillation fraction comprising methanol, tertiary butyl alcohol and water, wherein the first distillation fraction and a first recycle isobutylene fraction are reacted to form an isobutylene conversion product that is charged, together with recycle isobutylene to a methanol extraction zone and countercurrently contacted with water to provide an overhead extract comprising aqueous isobutylene, and wherein the isobutylene is recovered and recycled.
    Type: Grant
    Filed: November 19, 1992
    Date of Patent: September 7, 1993
    Assignee: Texaco Chemical Company
    Inventors: Charles J. Kruse, Rei-Yu J. Hwan, Kyle L. Preston, Feng-Ran Sheu