Patents Assigned to Chemical Research & Licensing Company
  • Patent number: 6337412
    Abstract: A three stage process for producing propylene oxide from propylene, oxygen, and hydrogen. The first reaction step is the oxidation of isopropanol/water with molecular oxygen in a reaction-distillation column (approx. 500 psi and 350° F.), to produce hydrogen peroxide and acetone. The column is configured with an upper high liquid holdup reaction zone and a lower short residence time stripping zone. Inert gas circulating through the column effects separation of the hydrogen peroxide as part of the bottoms fraction and acetone as part of the distillate fraction. The liquid part of the distillate fraction comprising acetone, isopropanol and water is then reacted with hydrogen (second reaction step) under reactive-distillation conditions to convert the contained acetone back to isopropanol for subsequent recycle to the first reaction step. The third reaction step is the epoxidation of propylene (in stoichiometric excess) with the hydrogen peroxide solution in the presence of a titanium silicalite catalyst.
    Type: Grant
    Filed: April 24, 2001
    Date of Patent: January 8, 2002
    Assignee: Chemical Research & Licensing Company
    Inventor: Abraham P. Gelbein
  • Patent number: 5792428
    Abstract: An apparatus for oligomerization of C.sub.4 and C.sub.5 isoolefins or the etherification thereof with C.sub.1 to C.sub.6 alcohols wherein the reactants are contacted first in a partial liquid phase reactor (boiling point reactor) with a fixed bed acid cation exchange resin catalyst at an LHSV of 5 to 20, pressure of 0 to 400 psig and temperature of 120.degree. to 300.degree. F., at a pressure to maintain the reaction mixture at its boiling point whereby at least a portion but less than all of the reaction mixture is vaporized and the entire reaction stream is directed to a catalytic distillation column reactor for further reaction of the reactants, where the improvement is having a decoupling drum between the boiling point reactor and the catalytic distillation column reactor. The addition of a decoupler drum allows the reactors to operate at a pressure independent of each other.
    Type: Grant
    Filed: May 20, 1996
    Date of Patent: August 11, 1998
    Assignee: Chemical Research & Licensing Company
    Inventors: Amarjit S. Bakshi, Timothy P. McGuirk, J. C. Gupta, Thomas Koval
  • Patent number: 5741930
    Abstract: A process for selectively reducing nitrile contaminants in fluids such as water, methanol or hydrocarbon streams containing mono olefins and which contain minor amounts of contaminants comprising nitriles in the presence of hydrogen and a supported cobalt catalyst. In the olefin stream the nitrile contaminants are substantially reduced without substantial reduction of the mono olefins.
    Type: Grant
    Filed: April 28, 1997
    Date of Patent: April 21, 1998
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Kyte H. Terhune
  • Patent number: 5730843
    Abstract: A contact structure, useful as a distillation structure, has a rigid frame made of two substantially vertical duplicate grids spaced apart and held rigid by a plurality of substantially horizontal rigid members and a plurality of substantially horizontal wire mesh tubes mounted to the grids to form a plurality of fluid pathways among the tubes. For use as a catalytic distillation structure, which serves as both the distillation structure and the catalyst, at least a portion of the wire mesh tubes contain a particulate catalytic material. The catalyst within the tubes provides a reaction zone where catalytic reactions may occur and the wire mesh provides mass transfer surfaces to effect a fractional distillation. The spacing elements provide for a variation of the catalyst density and loading and structural integrity.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: March 24, 1998
    Assignee: Chemical Research & Licensing Company
    Inventors: Willibrord A. Groten, Derwyn Booker, Clifford S. Crossland
  • Patent number: 5684213
    Abstract: A method for producing dialkyl ethers comprising feeding a stream containing a C.sub.1 to C.sub.4 alcohol to a distillation column reactor into a feed zone, contacting the stream with a fixed bed zeolite prepared as a distillation structure to form the corresponding dialkyl ether and water, and concurrently fractionating the ether product from the water and unreacted materials wherein the improvement is the addition of a small amount of hydrogen to the reaction zone to inhibit catalyst fouling and substantially increasing the catalyst life and activity.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: November 4, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Speros Peter Nemphos, Dennis Hearn
  • Patent number: 5679862
    Abstract: A process for the amination of aliphatic alkane derivatives such as alcohols (mono and polyhydric) which uses catalytic distillation to take advantage of the condensing distillate within the distillation reaction zone in the distillation column reactor. The operation of the distillation column reactor results in both a liquid and vapor phase within the distillation reaction zone. The catalyst is prepared in the form of a distillation structure. The reaction is carried out in a distillation column reactor at a low hydrogen partial pressure, e.g. in the range of 0.1 psia to less than 10 psia.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: October 21, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Speros Peter Nemphos, Dennis Hearn
  • Patent number: 5679241
    Abstract: The C.sub.2 to C.sub.5 and heavier acetylenes and dienes in a thermally cracked feed stream are hydrogenated without significantly hydrogenating the C.sub.2 and C.sub.3 olefins. Additionally, the C.sub.4 and heavier olefins may be hydrogenated. Specifically, the cracked gas feed in an olefin plant is hydrogenated in a distillation reaction column containing a hydrogenation catalyst without the necessity of separating the hydrogen out of the feed and without any significant hydrogenation of the ethylene and propylene. A combined reaction-fractionation step known as catalytic distillation hydrogenation is used to simultaneously carry out the reactions and separations while maintaining the hydrogenation conditions such that the ethylene and propylene remain substantially un-hydrogenated and essentially all of the other C.sub.2 and heavier unsaturated hydrocarbons are hydrogenated. Any unreacted hydrogen can be separated by a membrane and then reacted with separated C.sub.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: October 21, 1997
    Assignees: ABB Lummus Global Inc., Chemical Research & Licensing Company
    Inventors: Stephen J. Stanley, Francis D. McCarthy, Charles Sumner, Gary Robert Gildert
  • Patent number: 5628880
    Abstract: A process for removing dienes from etherification uses a hydrogenation zone in the reactor distillation column above the etherification zone. MTBE is produced and the unreacted C.sub.4 stream is also subjected to selective hydrogenation of the butadiene contained in the C.sub.4 feed stream. The C.sub.4 stream is first contacted with methanol in the etherification zone where the MTBE is distilled downward. The unreacted C.sub.4 's then are subjected to selective hydrogenation in the hydrogenation zone where butadiene in the overhead raffinate is reduced by over 90%. The hydrotreated C.sub.4 's are thus suitable for cold acid alkylation or other use wherein butadiene is harmful.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: May 13, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Gary R. Gildert, Willibrord A. Groten
  • Patent number: 5629451
    Abstract: A process for selectively reducing nitrile contaminants in fluids such as water, methanol or hydrocarbon streams containing mono olefins and which contain minor amounts of contaminants comprising nitriles in the presence of hydrogen and a supported cobalt catalyst. In the olefin stream the nitrile contaminants are substantially reduced without substantial reduction of the mono olefins.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: May 13, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Kyte H. Terhune
  • Patent number: 5618503
    Abstract: A method of preparing antimony pentafluoride comprising converting antimony compounds to hydroxonium fluoroantimonates by reaction of the antimony compounds with fluorinating material, such as hydrogen fluoride, in the presence of an oxidizing agent, such as hydrogen peroxide, removing water from the reaction product to concentrate the hydroxonium fluoroantimonates and reacting the hydroxonium fluoroantimonates with carbonyl difluoride to produce antimony pentafluoride. In one embodiment the hydroxonium fluoroantimonates are prepared by recovering the antimony from spent alkylation catalyst comprising SbF.sub.5 deposited on silica. The silica can also be recovered and recycled to produce a remanufactured alkylation catalyst.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: April 8, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Alan Johnson, H. J. Woods, H. J. Connor
  • Patent number: 5600049
    Abstract: In the alkylation of benzene with propylene in a distillation column reactor to produce cumene the overheads from the distillation reactor are fed to a depropanizer where the unreacted benzene is separated from C.sub.3 's. Liquid propylene feed for the distillation column reactor is vaporized by indirect heat exchange with the overheads from the depropanizer to condense the overheads, thereby reducing the pressure in the depropanizer below what would be normally achieved with conventional condensing systems.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: February 4, 1997
    Assignee: Chemical Research & Licensing Company
    Inventor: Angel Sy
  • Patent number: 5599997
    Abstract: A process for the hydrogenation of aniline to produce cyclohexyl amine is disclosed wherein the reaction is carried out in a distillation column reactor at a hydrogen partial pressure in the range of 0.1 psia to less than 100 psia. The catalyst is prepared in the form of a catalytic distillation structure. Within the distillation reaction zone there is an internal reflux and liquid from an external reflux which cool the rising vaporous aniline condensing a portion within the bed.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: February 4, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Speros P. Nemphos
  • Patent number: 5597476
    Abstract: A catalytic cracked naphtha is desulfurized with minimum loss of olefins and octane. The naphtha is fed to a first distillation column reactor which acts as a depentanizer or dehexanizer with the lighter material containing most of the olefins and mercaptans being boiled up into a first distillation reaction zone where the mercaptans are reacted with diolefins to form sulfides which are removed in the bottoms along with any higher boiling sulfur compounds. The bottoms are subjected to hydrodesulfurization in a second distillation column reactor where the sulfur compounds are converted to H.sub.2 S and removed. The lighter fraction containing most of the olefins is thus not subjected to the more harsh hydrogenation conditions of the second reactor.
    Type: Grant
    Filed: August 28, 1995
    Date of Patent: January 28, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Thomas P. Hickey
  • Patent number: 5595634
    Abstract: A process for treating C.sub.3 to C.sub.12 petroleum fractions, such as a light cracked naphtha to be used as an etherification feed stock in which H.sub.2 S is removed by distillation of at least the C.sub.3 fraction and mercaptans and diolefins are removed simultaneously in a distillation column reactor using a dual catalyst bed. The mercaptans and H.sub.2 S are reacted with the diolefins in the presence of a reduced nickel catalyst to form sulfides which are higher boiling than the portion of the feed which is fractionated to an upper hydrogenation catalyst bed of palladium for hydrogenating diolefins and acetylenes. The higher boiling sulfides are removed as bottoms along with heavier materials. Any diolefins not converted to sulfides and acetylenes are selectively hydrogenated to mono-olefins in the presence of a palladium oxide catalyst in an upper bed, producing overheads, substantially free of sulfur compounds, diolefins and acetylenes.
    Type: Grant
    Filed: July 10, 1995
    Date of Patent: January 21, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Gary R. Gildert, Hugh M. Putman
  • Patent number: 5554264
    Abstract: To heat the circulating reboiler streams of multiple distillation columns a fired reboiler is provided for a first column requiring the most heat. A portion of the bottoms from the first column is passed through the tubes of the heater in the fired reboiler and recycled to the first column as is normal. A slip stream is taken from the recycle after heating and passed on to provide heat by indirect heat exchange to a second reboiler and if desired other reboilers or heat exchangers. The slip stream may then be recycled to the bottoms of the first column directly or to the circulating steam of the first reboiler. A portion of the recycled slip stream can be taken as feed into the second column.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: September 10, 1996
    Assignee: Chemical Research & Licensing Company
    Inventor: Angel Sy
  • Patent number: 5510089
    Abstract: A method is provided for removing catalyst from a distillation column reactor and replacing the catalyst with fresh or regenerated catalyst. More specifically a small particulate catalyst is supported by wire mesh or screen or filter medium on trays in a conventional distillation column and substantially submerged by the liquid on the trays. The vapor rising through the liquid tends to keep the catalyst in suspension in the liquid. A draw-off is provided for each tray having catalyst supported thereon whereby liquid containing the suspended or slurried catalyst can be removed to a separator during operation. The catalyst is separated, as in a settling tank separator, from the liquid recycled to the tray until all the catalyst has been removed. The separated catalyst is removed for either regeneration or discarding. Fresh catalyst can then be added to the separator where it is slurried into the liquid again being recirculated from the tray.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: April 23, 1996
    Assignee: Chemical Research & Licensing Company
    Inventor: Edward M. Jones
  • Patent number: 5510568
    Abstract: A process for treating a light cracked naphtha to be used as an etherification or alkylation feedstock in which the mercaptans and diolefins are removed simultaneously in a distillation column reactor using a Pd catalyst. The mercaptans are reacted with the diolefins to form sulfides which are higher boiling than that portion of the naphtha which is used as feed to the etherification or alkylation unit. H.sub.2 S reacts in the same manner as the mercaptans to for the sulfides and is similarly removed from streams. The higher boiling sulfides are removed as bottoms along with any C.sub.6 and heavier materials. Any diolefins not converted to sulfides are selectively hydrogenated to mono-olefins for use in the etherification process. Certain C.sub.5 olefins, for example pentene-1 and 3-methyl butene-1 are isomerized during the process to more beneficial isomers.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: April 23, 1996
    Assignee: Chemical Research & Licensing Company
    Inventor: Dennis Hearn
  • Patent number: 5476978
    Abstract: Ethyl benzene is produced in a catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 50.degree. C. to 300.degree. C., using as the catalyst a mole sieve characterized as acidic by feeding ethylene to the catalyst bed while benzene is conveniently added through the reflux to result in a molar excess present in the reactor to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene and diethyl benzene in the bottoms. The bottoms are fractionated, the ethyl benzene recovered and the bottoms are contacted with benzene in the liquid phase in a fixed bed straight pass reactor under conditions to transalkylate the benzene thereby converting most of the diethyl benzene to ethyl benzene which is again separated and recovered.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: December 19, 1995
    Assignee: Chemical Research & Licensing Company
    Inventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
  • Patent number: 5457277
    Abstract: To heat the circulating reboiler streams of multiple distillation columns a fired reboiler is provided for a first column requiring the most heat. A portion of the bottoms from the first column is passed through the tubes of the heater in the fired reboiler and recycled to the first column as is normal. A slip stream is taken from the recycle after heating and passed on to provide heat by indirect heat exchange to a second reboiler and if desired other reboilers or heat exchangers. The slip stream may then be recycled to the bottoms of the first column directly or to the circulating steam of the first reboiler. A portion of the recycled slip stream can be taken as feed into the second column.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 10, 1995
    Assignee: Chemical Research & Licensing Company
    Inventor: Angel Sy
  • Patent number: 5446231
    Abstract: The present invention is a method for removing nitrile contaminants from C.sub.5 streams. In particular, a C.sub.5 stream is washed in a countercurrent fashion with a mixture comprising 50% methanol and 50% water to extract the nitriles from the C.sub.5 hydrocarbons into the water-methanol mixture. Propionitrile removal is enhanced by the presence of the methanol in the solvent. An further embodiments include (1) a method for recovering methanol from the extract stream by hydrogenating the nitriles to form amines, converting the amines to ammonium salts by acid treatment and distilling out the methanol and (2) distilling out methanol/nitriles from the extract stream, admixing the methanol/nitriles with an alkane/alkene/ether stream then distilling the methanol out in a azeotrope with the alkane/alkenes while leaving the nitriles in the ether.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: August 29, 1995
    Assignee: Chemical Research & Licensing Company
    Inventors: Robert P. Arganbright, Edward M. Jones, Jr., Dennis Hearn