Patents Assigned to Chemical Research & Licensing Company
  • Patent number: 4918243
    Abstract: A portion of the best of vaporization, required to separate and recover methanol from wash water used to remove methanol from a C.sub.4 raffinate resulting from the reaction of isobutene containing C.sub.4 hydrocarbons and methanol to produce MTBE is recovered by conducting the distillation of the methanol/water mixture at a pressure of 40 to 60 psig, thereby increasing the temerature of the methanol overhead to 104.degree. to 114.degree. C. and using the reaction effluent from the MTBE reactor to cool and condense the methanol overhead, said reactor effluent being correspondingly heated prior to entry into a debutanizer tower where unreacted C.sub.4 's and methanol are removed as a raffinate and MTBE product recovered. It is this raffinate that is washed with water to recover the unreacted methanol, with the methanol/water mixture being distilled as set forth above.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: April 17, 1990
    Assignee: Chemical Research & Licensing Company
    Inventors: Lawrence A. Smith, Jr., Edward M. Jones, Jr., Dennis Hearn
  • Patent number: 4849569
    Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: July 18, 1989
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4551567
    Abstract: Ethers such as isobutyl tertiary butyl ether are dissociated into their component alcohols and isolefins by heat stabilized catalyst compositions prepared from nuclear sulfonic acid, for example, macroporous crosslinked polyvinyl aromatic compounds containing sulfonic acid groups are neutralized with a metal of Al, Fe, Zn, Cu, Ni, ions or mixtures and alkali, alkaline earth metals or ammonium ions by contacting the resin containing the sulfonic acid with aqueous solutions of the metals salts and alkali, alkaline earth metal or ammonium salts. The catalysts have at least 50% of the sulfonic acid groups neutralized with metal ions and the balance of the sulfonic acid groups neutralized with alkali, alkaline earth ions or ammonium ions.
    Type: Grant
    Filed: September 7, 1984
    Date of Patent: November 5, 1985
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4536373
    Abstract: A method and apparatus for conducting catalytic chemical reactions and fractionation of the reaction mixture, comprising and feeding reactants into a distillation column reactor contracting said reactant in a liquid phase with a fixed bed catalyst in the form of a contact catalyst structure, consisting of closed porous containers containing the catalyst for the reaction and a clip means to hold and support said containers, which are disposed above, i.e., on the distillation trays in the tower. The trays have weir means to provide a liquid level on the trays to substantially cover the containers. In other words, the trays function in their ordinary manner with the addition thereto of the catalyst. The reaction mixture is concurrently fractionated in the column.
    Type: Grant
    Filed: October 19, 1983
    Date of Patent: August 20, 1985
    Assignee: Chemical Research & Licensing Company
    Inventor: Edward M. Jones, Jr.
  • Patent number: 4510336
    Abstract: Transetherification is carried out in a catalytic distillation reactor, wherein the catalytic structure also serves as a distillation structure, by feeding a first ether to the catalyst bed to at least partially dissociate it into a first olefin and a first alcohol while concurrently therewith feeding either a second olefin (preferably a tertiary olefin) having a higher boiling point than said first olefin or a second alcohol having a higher boiling point than said first alcohol to the catalyst whereby either the second olefin and the first alcohol or the first olefin and the second alcohol react to form a second ether which has a higher boiling point than the first ether, which second ether is concurrently removed as a bottoms in the concurrent reaction-distillation to force that reaction to completion, while the unreacted first olefin or first alcohol is removed in the overhead.
    Type: Grant
    Filed: October 20, 1982
    Date of Patent: April 9, 1985
    Assignee: Chemical Research & Licensing Company
    Inventor: Dennis Hearn
  • Patent number: 4504687
    Abstract: A method for producing tertiary ethers from C.sub.4 or C.sub.5 streams containing isobutene and isoamylene respectively in a process wherein a acidic cation exchange resin is used as the catalyst and as a distillation structure in a distillation reactor column, wherein the improvement is the operation of the catalytic distillation in two zones at different pressures, the first zone containing the catalyst packing and operated a higher pressure in the range of 100 to 200 psig in the case of C.sub.4 's and 15 to 100 psig in the case of C.sub.5 's which favors the etherification reaction and the second zone being a distillation operated at a lower pressure in the range of 0 to 100 psig in the case of C.sub.4 's and 0 to 15 psig in the case of C.sub.
    Type: Grant
    Filed: September 7, 1983
    Date of Patent: March 12, 1985
    Assignee: Chemical Research & Licensing Company
    Inventor: Edward M. Jones, Jr.
  • Patent number: 4482775
    Abstract: A method for isomerizing isobutene or n-butene to produce a mixture of isobutene and normal butene, and polymerizing at least a portion thereof to produce isobutene/n-butene codimer, which comprieses feeding at least 80 weight % of either the isobutene or n-butene to a catalytic distillation reactor containing a fixed bed acidic cation exchange resin catalyst packing which provides both the catalyst sites and distillation sites for the reaction products, isomerizing a portion of the isobutene or n-butene to produce a mixture of isobutene and n-butene and reacting at least a portion of the isobutene and n-butene to form codimer of isobutene and n-butene, whereby an overhead fraction containing any unreacted isobutene and n-butene and a bottoms fraction containing codimer is produced. The result of the reaction is substantially the same regardless whether the feed is isobutene or n-butene. Other aspects of the invention, include combinations of procedures to produce high purity isobutene and n-butene.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: November 13, 1984
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4447668
    Abstract: Alkyl tertiary butyl ether or alkyl tertiary amyl ether is dissociated by vapor phase contact with a cation acidic exchange resin at temperatures in the range of 150.degree. to 250.degree. F. at LHSV of 0.1 to 20 to produce a stream consisting of unreacted ether, isobutene or isoamylene and an alcohol corresponding to the alkyl radical. After the alcohol is removed, the ether/isoolefin stream may be fractionated to obtain a high purity isoolefin (99+%) or the ether/isoolefin stream can be contacted in liquid phase with a cation acidic exchange resin to selectively dimerize the isoolefin in a highly exothermic reaction, followed by fractionation of the dimerization product to produce high purity diisoolefin (97+%). In the case where the alkyl is C.sub.3 to C.sub.6 and the corresponding alcohol is produced on dissociation of the ether, combined dissociation-distillation may be carried out such that isoolefin is the overhead product and alcohol the bottom.
    Type: Grant
    Filed: May 25, 1983
    Date of Patent: May 8, 1984
    Assignee: Chemical Research & Licensing Company
    Inventors: Lawrence A. Smith, Jr., Edward M. Jones, Jr., Dennis Hearn
  • Patent number: 4443559
    Abstract: Catalytic distillation structure for use in reaction distillation columns, a providing reaction sites and distillation structure and consisting of a catalyst component and a resilient component intimately associated therewith. The resilient component has at least about 70 volume % open space and being present with the catalyst component in an amount such that the catalytic distillation structure consist of at least 10 volume % open space.
    Type: Grant
    Filed: September 30, 1981
    Date of Patent: April 17, 1984
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4439350
    Abstract: A method for conducting catalytic chemical reactions and fractionation of the reaction mixture comprising feeding reactants into a distillation column reactor contracting said reactant in liquid phase with a fixed bed catalyst in the form of a contact catalyst structure consisting of closed porous containers containing the catatlyst for the reaction and a clip means to hold and support said containers, which are disposed above, i.e., on the distillation trays in the tower. The trays have weir means to provide a liquid level on the trays to substantially cover the containers. In other words, the trays function in their ordinary manner with the addition thereto of the catalyst. The reaction mixture is concurrently fractionated in the column.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: March 27, 1984
    Assignee: Chemical Research & Licensing Company
    Inventor: Edward M. Jones, Jr.
  • Patent number: 4336407
    Abstract: A method for conducting chemical reactions and fractionation of the reaction mixture comprising feeding reactants to a distillation column reactor into a feed zone and concurrently contacting the reactants with a fixed bed catalytic packing to concurrently carry out the reaction and fractionate the reaction mixture.For example, a method for preparing methyl tertiary butyl ether in high purity from a mixed feed stream of isobutene and normal butene comprising feeding the mixed feed stream to a distillation column reactor into a feed zone at the lower end of a distillation reaction zone, and methanol into the upper end of said distillation reaction zone, which is packed with a properly supported cationic ion exchange resin, contacting the C.sub.4 feed and methanol with the catalytic distillation packing to react methanol and isobutene, and concurrently fractionating the ether from the column below the catalytic zone and removing normal butene overhead above the catalytic zone.
    Type: Grant
    Filed: February 17, 1981
    Date of Patent: June 22, 1982
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4332968
    Abstract: A method for separating primary and secondary amines by contacting a mixture thereof with mesityl oxide, which forms acetone and an adduct with the primary amine. Acetone is removed to force the reaction. The reaction is particularly useful for separating close boiling amines. The primary amine adducts have high boiling points, thereby allowing the secondary amine to be recovered in high purity by distillation. The primary amine may also be recovered by hydrolyzing the adduct which produces the primary amine and acetone.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: June 1, 1982
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4307254
    Abstract: A method for conducting chemical reactions and fractionation of the reaction mixture comprising feeding reactants to a distillation column reactor into a feed zone and concurrently contacting the reactants with a fixed bed catalytic packing to concurrently carry out the reaction and fractionate the reaction mixture. For example, a method for preparing methyl tertiary butyl ether in high purity from a mixed feed stream of isobutene and normal butene comprising feeding the mixed feed stream to a distillation column reactor into a feed zone at the lower end of a distillation reaction zone, and methanol into the upper end of said distillation reaction zone, which is packed with a properly supported cationic ion exchange resin, contacting the C.sub.4 feed and methanol with the catalytic distillation packing to react methanol and isobutene, and concurrently fractionating the ether from the column below the catalytic zone and removing normal butene overhead above the catalytic zone.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: December 22, 1981
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4306068
    Abstract: A method for separating primary and secondary amines by contacting a mixture thereof with mesityl oxide, which forms acetone and an adduct with the primary amine. Acetone is removed to force the reaction. The reaction is particulary useful for separating close boiling amines. The primary amine adducts have high boiling points, thereby allowing the secondary amine to be recovered in high purity by distillation. The primary amine may also be recovered by hydrolyzing the adduct which produces the primary amine and acetone.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: December 15, 1981
    Assignee: Chemical Research and Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4250052
    Abstract: Sulfonated cation resin catalyst structures are prepared by extruding a vinyl aromatic polymer or copolymer or by depositing a solution containing a vinyl aromatic polymer or copolymer on a base of the desired structure and sulfonating the structure.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: February 10, 1981
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4242530
    Abstract: A method for the separation of isobutene from a mixture comprising n-butene and isobutene comprising feeding a C.sub.4 stream containing n-butene and isobutene to a distillation column reactor into a feed zone contacting the stream with fixed bed acidic cation exchange resin to form diisobutene which passes to the bottom of the column, said n-butene being removed overhead. The reaction and distillation occur concurrently.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: December 30, 1980
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4232177
    Abstract: A method for conducting chemical reactions and fractionation of the reaction mixture comprising feeding reactants to a distillation column reactor into a feed zone and concurrently contracting the reactants with a fixed bed catalytic packing to concurrently carry out the reaction and fractionate the reaction mixture.For example, a method for preparing methyl tertiary butyl ether in high purity from a mixed feed stream of isobutene and normal butene comprising feeding the mixed feed stream to a distillation column reactor into a feed zone at the lower end of a distillation reaction zone, and methanol into the upper end of said distillation reaction zone, which is packed with a properly supported cationic ion exchange resin, contacting the C.sub.4 feed and methanol with the catalytic distillation packing to react methanol and isobutene, and concurrently fractionating the ether from the column below the catalytic zone and removing normal butene overhead above the catalytic zone.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: November 4, 1980
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4215011
    Abstract: A component of a distillation system having both a catalytic function and a distillation function.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: July 29, 1980
    Assignee: Chemical Research and Licensing Company
    Inventor: Lawrence A. Smith, Jr.