Patents Assigned to Reilly Industries
  • Patent number: 5493028
    Abstract: Disclosed are preferred processes for the preparation of 2-halo-nicotinic acid derivatives of formula (IV): ##STR1## by cyclocondensation of a 4-halo-4-cyanocarbonyl compound of formula (III): ##STR2## wherein X is Cl or Br; Y is a carbonyl group and R.sup.1, R.sup.2 and R.sup.3 are each, independently, H, Cl, Br or an organic radical. Further preferred aspects include the preparation of the above-noted 4-halo-4-cyanocarbonyl compound via Michael addition of a 2-halonitrile with an .alpha.,.beta.-unsaturated aldehyde or ketone, and the preparation of the 2-halonitrile by redistribution of halogen between a 2,2-dihalonitrile and a parent nitrile.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: February 20, 1996
    Assignee: Reilly Industries, Inc.
    Inventors: Tony Y. Zhang, Eric F. V. Scriven
  • Patent number: 5484929
    Abstract: A process for the selective chlorination of pyridine, a lower alkyl pyridine or 3-cyanopyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350.degree. to about 500.degree. C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340.degree. C.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: January 16, 1996
    Assignee: Reilly Industries
    Inventor: Joseph E. Toomey
  • Patent number: 5484873
    Abstract: Described are novel triethylenediamine adducts of certain 4-hydroxy-substituted, 3,5-hydroxy-substituted and 2,3,4-hydroxy-substituted benzoic acid derivatives, and novel boron trifluoride complexes with cyclic amidines, which are useful for the conversion of thermosettable compositions. Also described are novel thermosettable compositions incorporating the adducts and complexes.
    Type: Grant
    Filed: September 14, 1994
    Date of Patent: January 16, 1996
    Assignee: Reilly Industries
    Inventor: John R. Johnson
  • Patent number: 5446163
    Abstract: Processes for preparing pyridyl-substituted hydrazoles, dihydrothiadiazones or aminotriazinones by reaction of iminopyridines preformed in situ or otherwise with hydrazides or carbazides, or their sulfur counterparts, or with aminotriazinones.
    Type: Grant
    Filed: October 2, 1992
    Date of Patent: August 29, 1995
    Assignee: Reilly Industries, Inc.
    Inventors: Eric F. V. Scriven, James G. Keay, Tony Zhang
  • Patent number: 5444137
    Abstract: Described are preferred monomers including a vinylbenzyl moiety N-bonded to an alkylaminopyridinyl or pyridylimidazolyl function. Also described are preferred acid salts of such monomers. Additionally, preferred processes involving and resins formed from these preferred monomers are described. The preferred resins are highly selective for valuable heavy metal ions such as copper and demonstrate superior iron rejection values.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: August 22, 1995
    Assignee: Reilly Industries, Inc.
    Inventors: Donald W. McQuigg, Edward E. Sowers
  • Patent number: 5424436
    Abstract: Imines are synthesized by the hydrogenation of pyridinecarbonitriles with amines in the presence of a rhodium-loaded catalyst. The resulting imines are stable and may be transiminated and then hydrogenated to form selected secondary amine products or may be hydrolyzed to aldehydes.Further, a very useful class of unsymmetrical secondary amines represented by the formula RCH.sub.2 NHAr (in which R is not aliphatic and Ar is aromatic and not attached to R), which has heretofore been accessible only with some difficulty, can be synthesized by processes herein disclosed utilizing the reductive intermolecular coupling of nitriles and primary aromatic amines.
    Type: Grant
    Filed: September 8, 1993
    Date of Patent: June 13, 1995
    Assignee: Reilly Industries, Inc.
    Inventors: Gerald L. Goe, James G. Keay, Eric F. V. Scriven, Michael L. Prunier, Steven J. Quimby
  • Patent number: 5420223
    Abstract: Described are several preferred acid salts and complexes of N,N-dimethylpyridine (DMAP) and 4-(4-methyl-1-piperidinyl)pyridine (MPP) which are useful as curing agents or as accelerators in preferred epoxy resin curing processes. Also described are particularly preferred processes for forming cured epoxy resin materials which are advantageously employed in large production line scale operations, and curable coating compositions.
    Type: Grant
    Filed: October 19, 1993
    Date of Patent: May 30, 1995
    Assignee: Reilly Industries, Inc.
    Inventor: John R. Johnson
  • Patent number: 5416217
    Abstract: Processes for the preparation of 2,2'-bipyridyls by reacting a pyridine base in the presence of an elemental nickel catalyst, along with an effective amount of borohydride salt and ammonium hydroxide to reduce the inactivation of the nickel catalyst during the reactions.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: May 16, 1995
    Assignee: Reilly Industries Inc.
    Inventors: Gerald R. Goe, Charles K. McGill, Angela R. sherman
  • Patent number: 5403906
    Abstract: Described are preferred processes for producing linear polyvinylpyridines. The processes involve the use of hydrogen peroxide to initiate polymerization of vinylpyridine monomers in an alcohol/water solvent. Processes of the invention provide good reaction rates and conversions, and are particularly advantageous in achieving control of the M.sub.w 's of the final product polymers.
    Type: Grant
    Filed: October 25, 1993
    Date of Patent: April 4, 1995
    Assignee: Reilly Industries, Inc.
    Inventors: Eric F. V. Scriven, James R. Stout, James G. Keay, Ramiah Murugan
  • Patent number: 5371160
    Abstract: Described are unique polymerization processes for preparing linear polyvinylpyridine polymers as well as unique linear polyvinylpyridine polymer compositions. The processes involve the use of an alkylpyridine anion as an anionic polymerization catalyst and result in linear polyvinylpyridines having alkylpyridine end groups homologous to the pendant pyridines of the polymer. Processes of the invention are particularly advantageous in preparing relatively low molecular weight linear polyvinylpyridines without the need to use large amounts of catalyst to achieve the same.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: December 6, 1994
    Assignee: Reilly Industries, Inc.
    Inventors: Ernest Crowe, James G. Keay, Eric F. V. Scriven
  • Patent number: 5290404
    Abstract: A preferred electrochemical process for producing an alcohol or carboxylic acid from a corresponding metal salt while also recovering metal cation residues is described. The preferred process does not require a three-compartment desalination cell but rather can be performed in a standard two-compartment cell divided by a cation-permeable membrane. The process comprises the step of electrolyzing an aqueous medium containing the metal salt in the anolyte of the cell to thereby yield alcohol or carboxylic acid in the anolyte and pass the metal cation into the catholyte. In one particularly preferred mode, the process provides a highly effective recovery of valuable materials from byproduct streams of base-catalyzed syntheses of polyols such as such as trimethylolpropane or pentaerythritol from aldehydes, and in another provides an efficient recovery of phenol.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: March 1, 1994
    Assignee: Reilly Industries, Inc.
    Inventor: Joseph E. Toomey
  • Patent number: 5266731
    Abstract: Described are processes for producing amines from nitriles. The processes include electrocatalytic hydrogenations of nitriles in the presence of transition metal-oxide and/or transition metal-hydroxide cathodes to thereby form amines. Preferred modes of the invention provide highly advantageous processes for producing hexamethylenediamine from adiponitrile.
    Type: Grant
    Filed: July 17, 1991
    Date of Patent: November 30, 1993
    Assignee: Reilly Industries
    Inventors: William M. Ayers, Mary H. Dean
  • Patent number: 5266184
    Abstract: Described is a preferred process for obtaining an increased pitch yield from the distillation of crude coal tar material. The process includes treating a crude coal tar material by reaction with formaldehyde, followed by distillation of the coal tar to afford a yield of coal tar pitch which is significantly increased over that obtained without the formaldehyde treatment.
    Type: Grant
    Filed: February 7, 1992
    Date of Patent: November 30, 1993
    Assignee: Reilly Industries, Inc.
    Inventor: William R. Roder
  • Patent number: 5252741
    Abstract: Imines are synthesized by the hydrogenation of pyridinecarbonitriles with amines in the presence of a rhodium-loaded catalyst. The resulting imines are stable and may be transiminated and then hydrogenated to form selected secondary amine products or may be hydrolyzed to aldehydes.Further, a very useful class of unsymmetrical secondary amines represented by the formula RCH.sub.2 NHAr (in which R is not aliphatic and Ar is aromatic and not attached to R), which has heretofore been accessible only with some difficulty, can be synthesized by processes herein disclosed utilizing the reductive intermolecular coupling of nitriles and primary aromatic amines.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: October 12, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Gerald L. Goe, James G. Keay, Eric F. V. Scriven, Michael L. Prunier, Steven J. Quimby
  • Patent number: 5247093
    Abstract: A process for the selective chlorination of pyridine or a lower alkyl pyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350.degree. to about 500.degree. C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340.degree. C.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: September 21, 1993
    Assignee: Reilly Industries, Inc.
    Inventor: Joseph E. Toomey
  • Patent number: 5229479
    Abstract: A cross-linked polymer-supported 4-(N-benzyl-N-methylamino) pyridine material and process for its preparation in high yield and having effective physical and catalytic properties. The polymer-supported catalyst is characterized by the suspension copolymerization of an organic phase containing the corresponding vinyl-substituted pyridine monomer, a styrene monomer, and a suitable cross-linking agent and free radical-generating catalyst in the presence of an aqueous phase containing a cellulose ether derivative as the stabilizing agent. The catalyst is further characterized by its yield in excess of 90% by weight and by its predominant and generally spherical and smooth bead form and substantially uniform size that is efficiently hard and durable and possesses sufficient catalytic activity for effective use in acylation, alkylation or other related reactions.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: July 20, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Donald W. McQuigg, Heather K. Webb, Edward E. Sowers
  • Patent number: 5229519
    Abstract: Disclosed are preferred processes for preparing a 2-halo-5-halomethylpyridine compound. The preferred processes involve cyclocondensing a 2-halo-2-halomethyl aldehyde or ketone of the formula (II) ##STR1## to form a 2-halo-2-halomethylpyridine compound of the formula (III) ##STR2## wherein X is Cl or Br, Y is a cyano group or an aminocarbonyl group, and R, R.sup.1, R.sup.2 and R.sup.3 are, independently, H or an organic radical which does not interfere with the cyclocondensation.
    Type: Grant
    Filed: March 6, 1992
    Date of Patent: July 20, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Tony Y. Zhang, Eric F. V. Scriven
  • Patent number: 5221747
    Abstract: Processes for the preparation of 2,2'-bipyridyls by reacting a pyridine base in the presence of a nickel catalyst which comprises a significant amount of elemental nickel bound on a suitable support. In one embodiment the coupling reaction takes place in several reactor designs at a temperature of about 200.degree.-240.degree. C. and a pressure sufficient to maintain at least some of the base in a liquid state during the reaction. In other preferred embodiments, processes for preparing 2,2'-bipyridyls are conducted at a temperature between about 175.degree.-240.degree. C. These latter processes require that the nickel have a high specific Ni surface area.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: June 22, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Gerald R. Goe, Charles K. McGill, Angela R. Sherman
  • Patent number: 5218122
    Abstract: An improved base synthesis process and catalyst for the preparation of pyridine or its alkylpyridine derivatives involving the catalytic reaction of one or more aldehydes and/or ketones containing from one to about five carbon atoms, with at least one reactant having more than one carbon atom, with ammonia in the gas phase. The improved catalyst comprises an effective amount of a shape-selective zeolite which has been modified by treatment with one or more metal ions or compounds of tungsten. zinc or tin. The preferred zeolite has a constraint index of about 1 to 12 and a high silica content and correspondingly low concentration of ion-exchange sites with minimal to no acidic sites present.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: June 8, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Gerald I. Goe, Robert D. Davis
  • Patent number: 5183895
    Abstract: A cross-linked polymer-supported 4-(N-benzyl-N-methylamino) pyridine material and process for its preparation in high yield and having effective physical and catalytic properties. The polymer supported catalyst is characterized by the suspension copolymerization of an organic phase containing the corresponding vinyl-substituted pyridine monomer, a styrene monomer, and a suitable cross-linking agent and free radical-generating catalyst in the presence of an aqueous phase containing a cellulose ether derivative as the stabilizing agent. A purified acid salt of the vinyl-substituted pyridine monomer useful in polymerizations and stable for storage as either a solid or an aqueous solution.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: February 2, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Donald W. McQuigg, Edward E. Sowers, Gerald L. Goe, Eric F. V. Scriven, James G. Keay