Patents Represented by Attorney Richard J. Hammond
  • Patent number: 5210243
    Abstract: A ruthenium-phosphite complex having the formula ##STR1## wherein a is from 1 to 3; b is 1 or 2; c is from 0 to 3; and R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR2## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl.This complex can be used to effect the reduction of unsaturated organic compounds or, when comprised of ligands having optical activity, can be used as the catalyst for effecting the asymmetric reduction of unsaturated organic compounds.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: May 11, 1993
    Assignee: Ethyl Corporation
    Inventor: Charles H. Kolich
  • Patent number: 5210304
    Abstract: A continuous process for the hydrocarbylthiation of aromatic amines is disclosed. The process involves forming an admixture of aromatic amine, hydrocarbyl disulfide and an effective amount of a Lewis acid catalyst and subsequently allowing such admixture to flow as a thin film along a column. An inert gas is passed in a counter-current manner through the admixture.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: May 11, 1993
    Assignee: Ethyl Corporation
    Inventors: John F. Balhoff, Donald E. Balhoff
  • Patent number: 5206377
    Abstract: Melatonin compounds are disclosed of the formula ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkylene substituted with phenyl; R.sub.1 is hydrogen, substituted benzyl, naphthylmethyl or taken together with R.sub.2 and the two carbon atoms of the five-membered hetero ring form the group ##STR2## where R.sub.1 ' is C.sub.1 to C.sub.6 linear or branched alkanoyl and R.sub.1 " is hydrogen, C.sub.1 to C.sub.6 linear or branched alkyl or phenyl optionally substituted with one or more halogen, amino, nitro, hydroxy, alkyl, alkoxy or haloalkyl; R.sub.2 is hydrogen, 1-pyrrolyl, 1-pyrrolyl substituted with one or more alkyl or alkoxy, the group --(CH.sub.2).sub.m --NHR.sub.2 '1, where m is 1 to 3 and R.sub.2 ' is phenyl sulfonyl, the phenyl group optionally substituted with alkyl, or --C(O)--R.sub.2 ", where R.sub.2 " is C.sub.1 to C.sub.
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: April 27, 1993
    Assignee: Whitby Research, Inc.
    Inventor: Donald A. McAfee
  • Patent number: 5206004
    Abstract: Improved molecular sieves and processes for treatment of molecular sieves which permit use for separation of ethylene and silane without attending formation of ethylsilane. Such treatment includes treatment of sieves with silane at an effective temperature, pressure and time.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: April 27, 1993
    Assignee: Ethyl Corporation
    Inventor: Won S. Park
  • Patent number: 5204307
    Abstract: Production of alkyl substituted aromatic diamines by reacting triethlyaluminum with an aromatic diamine and a chloride ion source in the presence of an olefin is disclosed. The alkyl substituted aromatic diamines are useful as chain extenders in polyurethane processes.
    Type: Grant
    Filed: January 13, 1992
    Date of Patent: April 20, 1993
    Assignee: Ethyl Corporation
    Inventors: Kryn G. Ihrman, Olan W. Mitchell, R. Woodrow Wilson, Jr.
  • Patent number: 5204339
    Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein X is selected from the group consisting of oxygen and sulfur; R' is H or a lower alkyl group having 1-4 carbon atoms; m is 2-6; n is 0-17 and R is --CH.sub.3 ; wherein R is H or a lower alkyl group, m is 5-7 and n is 0-17.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: April 20, 1993
    Assignee: Whitby Research, Inc.
    Inventors: Gevork Minaskanian, James V. Peck, Vithal J. Rajadhyaksha
  • Patent number: 5202472
    Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: April 13, 1993
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
  • Patent number: 5198576
    Abstract: Bicyclooctyl phosphines are disclosed having the formula: ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, phenyl, substituted phenyl, halo, or C.sub.1 or C.sub.6 alkoxy; Ar is phenyl, substituted phenyl, naphthyl or substituted naphthyl; and x is 0 or 1.These phosphines are treated with ruthenium compounds to form a complex of the formula Ru.sub.x H.sub.y Cl.sub.z (anthraphos-m).sub.2 (S).sub.p, where S is a tertiary amine; and when y is 0, then x is 2, z is 4 and p is 1; and when y is 1, then x is 1, z is 1 and p is 0; where anthraphos-m is: ##STR2## where R is C.sub.1 to C.sub.6 linear or branched alkyl, phenyl, substituted phenyl, C.sub.1 to C.sub.6 linear or branched alkoxy or halo; Ar is phenyl or substituted phenyl or naphthyl or substituted naphthyl; and m is 0 or 1.The complex is useful in a process for the asymmetric reduction of olefinic carboxylic acids of the formula: ##STR3## where R.sub.1 and R.sub.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: March 30, 1993
    Assignee: Ethyl Corporation
    Inventor: Ralph T. Scannell
  • Patent number: 5196418
    Abstract: Compounds of the present invention are those having the formula: ##STR1## where R is a linear or branched chain of 1 to 22 carbon atoms selected from the group consisting of alkyl, alkenyl or alkynyl or said C.sub.1 to C.sub.22 chains substituted with --SR.sub.3, --OR.sub.3, --NHR.sub.3, --CH.sub.3, or --C(O)OR.sub.2 where R.sub.2 is hydrogen or C.sub.1 to C.sub.6 alkyl; R.sub.1 is hydrogen, C.sub.1 to C.sub.6 alkyl, --SR.sub.3, --OR.sub.3, --NHR.sub.3, --NR'.sub.3 R.sub.3, or --C(O)OR.sub.2 where R.sub.2 is as previously defined; R.sub.3 and R'.sub.3 are the same or different and are hydrogen, C.sub.1 to C.sub.6 alkyl, alkylthioalkyl, alkoxyalkyl, aminoalkyl, aminoalkyl substituted with phenyl, substituted phenyl, benzoyl, substituted benzoyl, heteroaryl or substituted heteroaryl; R.sub.4 is hydrogen, C.sub.1 to C.sub.6 alkyl, or --C(O)OR.sub.2 where R.sub.2 is defined previously; R.sub.5 is hydrogen, C.sub.1 to C.sub.6 alkyl, phenyl, or substituted phenyl; R.sub.6 is hydrogen, C.sub.1 to C.sub.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Board of Supervisors, Louisiana State University Agricultural & Mechanical College
    Inventors: Richard D. Gandour, Gnanasambandam Kumaravel
  • Patent number: 5194651
    Abstract: A process is disclosed for the preparation of aliphatic toluenesulfonates. The process comprises reacting a solution of an aliphatic alcohol and an alkali metal hydroxide in a solution of an aprotic solvent with toluenesulfonyl chloride for from about 1 to about 12 hours and forming said aliphatic toluenesulfonate. These compounds are useful intermediates in the preparation of complex organic molecules.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: March 16, 1993
    Assignee: Ethyl Corporation
    Inventor: Merrikh Ramezanian
  • Patent number: 5190905
    Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: March 2, 1993
    Assignee: Ethyl Corporation
    Inventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
  • Patent number: 5191095
    Abstract: A process for the asymmetric reduction of olefinic amides of the formula ##STR1## where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: March 2, 1993
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
  • Patent number: 5189208
    Abstract: A process for obtaining a substantially pure enantiomer of ibuprofen is described. The process utilizes first an enantiomerically enriched mixture of ibuprofen obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is dissolved in a solvent and solid racemic ibuprofen is separated, leaving a mother liquid comprising the solvent and the enriched enantiomer substantially free of the other enantiomer.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: February 23, 1993
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 5187285
    Abstract: 3,3'-Thiobis(2,5-dihydrothiophene-1,1-dioxides) on heating with a reactive Diels-Alder dienophile undergo a reaction producing thioethers having two six-membered alicyclic rings in the molecule, such as 4,4'-thiobis(3,6-dihydrophthalic acids) or the esters, anhydrides or imides thereof, and 4,4'-thiobis-(1,2,3,6-tetrahydrophthalic acids) or the esters, anhydrides or imides thereof. Both rings of the dihydrothiophene dioxides participate in the reaction, apparently by forming a tetraene structure which co-reacts with two equivalents of the dienophile to form an adduct in which each six-membered ring has one or two olefinic double bonds. During the course of the reaction, the thioether bridge remains intact. Some of the bis(alicyclic) thioethers are readily converted to the corresponding bis(aromatic)thioethers by use of known aromatization methods and systems. Various utilities for the products of the foregoing reactions are described.
    Type: Grant
    Filed: August 22, 1990
    Date of Patent: February 16, 1993
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 5187281
    Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: February 16, 1993
    Assignee: Ethyl Corporation
    Inventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
  • Patent number: 5187136
    Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: February 16, 1993
    Assignee: Ethyl Corporation
    Inventors: W. Dirk Klobucar, Charles H. Kolich, Thanikavelu Manimaran
  • Patent number: 5187135
    Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: February 16, 1993
    Assignee: Ethyl Corporation
    Inventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
  • Patent number: 5183061
    Abstract: Organic silicon compounds such as tetraloweralkylorthosilicates, silicon tetracarboxylates, and silicon-containing reaction products derived from carbohydrates, such as glucose, sucrose, and ascorbic acid are useful in treating, preventing, or delaying the onset of bone disease in warm blooded vertebrates, including man and domesticated animals of economic importance, such as poultry, house pets, and horses, cattle, swine, and sheep.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: February 2, 1993
    Assignee: Ethyl Corporation
    Inventors: Karl E. Wiegand, Patrick C. Hu
  • Patent number: 5177231
    Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: January 5, 1993
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
  • Patent number: 5177250
    Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: January 5, 1993
    Assignee: Ethyl Corporation
    Inventor: Kathleen S. Laurenzo