Patents by Inventor Charles K. McGill
Charles K. McGill has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5416217Abstract: 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: GrantFiled: June 22, 1993Date of Patent: May 16, 1995Assignee: Reilly Industries Inc.Inventors: Gerald R. Goe, Charles K. McGill, Angela R. sherman
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Patent number: 5221747Abstract: 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: GrantFiled: June 9, 1992Date of Patent: June 22, 1993Assignee: Reilly Industries, Inc.Inventors: Gerald R. Goe, Charles K. McGill, Angela R. Sherman
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Patent number: 5003069Abstract: In a Chichibabin amination of a nitrogen-containing heterocyclic base by sodamide in an organic solvent, the improvement comprising conducting the reaction under pressure of at least about 50 psi in the gas phase above the reaction mixture and adding ammonia to the mixture sufficient to produce a partial pressure of ammonia of at least about 5 psi in the gas phase. Preferred temperature and pressure ranges are disclosed, as are catalysts and other preferred steps for practicing the reaction. Significant results are obtained including improved and changed yields from those classically expected in Chichibabin aminations, including new compositions of matter in at least three cases.Type: GrantFiled: July 26, 1989Date of Patent: March 26, 1991Assignee: Reilly Industries, Inc.Inventors: Charles K. McGill, James J. Sutor
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Patent number: 4966972Abstract: A process 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. 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.Type: GrantFiled: January 19, 1989Date of Patent: October 30, 1990Assignee: Reilly Industries, Inc.Inventors: Gerald L. Goe, Charles K. McGill, Angela R. Sherman
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Patent number: 4405790Abstract: An improved process for preparing the 2-alkylamino-5-alkylpyridine and 2-amino-5-alkylpyridine amination products of 3-alkylpyridines, comprising the step of initially reacting the base directly with the sodium salt of a primary alkylamine to produce the 2-alkylamino form, wherein the alkyl group in each reactant has from 1 to about 20 carbon atoms. The sodium salt is preferably preformed in situ by adding the alkylamine to a dispersion of sodium in an organic solvent heated to about 100.degree.-120.degree. C. The substituted amination preferably proceeds at a temperature of about 100.degree.-140.degree. C. in a solvent such as toluene and under an inert nitrogen atmosphere. The ratio of 2,5-:2,3- isomer products of the reaction is up to about 10:1 or more, with the effective yield of the 2,5-alkylated isomer being about 25% or more.Type: GrantFiled: April 8, 1982Date of Patent: September 20, 1983Assignee: Reilly Tar & Chemical Corp.Inventors: Charles K. McGill, Thomas D. Bailey
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Patent number: 4386209Abstract: In a Chichibabin amination of a pyridine base by sodamide in an organic solvent, the improvement comprising conducting the reaction under pressure of at least about 50 psi in the gas phase above the reaction mixture and adding ammonia to the mixture sufficient to produce a partial pressure of ammonia of at least about 5 psi in the gas phase. Preferred temperature and pressure ranges are disclosed, as are catalysts and other preferred steps for practicing the reaction. Significant results are obtained including improved and changed yields from those classically expected in Chichibabin aminations, including new compositions of matter in at least one case.Type: GrantFiled: April 8, 1982Date of Patent: May 31, 1983Assignee: Reilly Tar & Chemical CorporationInventors: Charles K. McGill, James J. Sutor
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Patent number: 4267335Abstract: A process for preparing substituted 2,2'-bipyridyl compounds and several compounds so prepared, the process comprising the steps of first selecting a substituted pyridine of the formula defined herein, then mixing a stoichiometric excess of the substituted pyridine with an amount of sodamide, causing the resultant mixture to be at a temperature sufficiently high to cause substituted 2,2'-bipyridyl formation, and isolating the substituted 2,2'-bipyridyl thereby formed. The new substituted 2,2'-bipyridyl compounds are selected from the group consisting of 4,4'-di-(5-nonyl)-2,2'-bipyridyl; 4,4'-di-(3-pentyl)-2,2'-bipyridyl; 6,6'-di-(3-pentyl)-2,2'-bipyridyl; 6,6'-di-(5-nonyl)-2,2'-bipyridyl; 4,4'-di-(cyclohexylmethyl)-2,2'-bipyridyl; 5,5'-di-(5-nonyl)-2,2'-bipyridyl; 4,4'-di-(3-phenylpropyl)-2,2'-bipyridyl; 4,4'-di-(4-tetrahydropyranyl)-2,2'-bipyridyl; 4,4'-di-benzyl-2,2'-bipyridyl; 6,6'-di-isoamyl-2,2'-bipyridyl; and 4,4'-di-(t-butyl)-2,2'-bipyridyl.Type: GrantFiled: May 21, 1979Date of Patent: May 12, 1981Assignee: Reilly Tar & Chemical CorporationInventor: Charles K. McGill
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Patent number: 4177349Abstract: A process for preparing substituted 2,2'-bipyridyl compounds and several compounds so prepared, the process comprising the steps of first selecting a substituted pyridine of the formula defined herein, then mixing a stoichiometric excess of the substituted pyridine with an amount of sodamide, causing the resultant mixture to be at a temperature sufficiently high to cause substituted 2,2'-bipyridyl formation, and isolating the substituted 2,2'-bipyridyl thereby formed. The new substituted 2,2'-bipyridyl compounds are selected from the group consisting of 4,4'-di-(5-nonyl)-2,2'-bipyridyl; 4,4'-di-(3-pentyl)-2,2'-bipyridyl; 6,6'-di-(3-pentyl)-2,2'-bipyridyl; 6,6'-di-(5-nonyl)-2,2'-bipyridyl; 4,4'-di-(cyclohexylmethyl)-2,2'-bipyridyl; 5,5'-di-(5-nonyl)-2,2'-bipyridyl; 4,4'-di-(3-phenylpropyl)-2,2'-bipyridyl; 4,4'-di-(4-tetrahydropyranyl)-2,2'-bipyridyl; 4,4'-di-benzyl-2,2'-bipyridyl; 6,6'-di-isoamyl-2,2'-bipyridyl; and 4,4'-di-(t-butyl)-2,2'-bipyridyl.Type: GrantFiled: July 27, 1978Date of Patent: December 4, 1979Assignee: Reilly Tar & Chemical CorporationInventor: Charles K. McGill
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Patent number: 4158093Abstract: A process for dequaternizing a 2-(2-pyridyl)ethyl or 2-(4-pyridyl)ethyl quaternary salt of a pyridine or bipyridine base comprising the step of heating or reacting the pyridylethyl quaternary salt with a caustic material such as sodium hydroxide. Also included is a process for preparing a second pyridine base (or a bipyridine base) in which a first pyridine base is initially selected and its 2-(2-pyridyl)ethyl or 2-(4-pyridyl)ethyl quaternary salt or its acid salt prepared. An electrophilic, nucleophilic or coupling reaction can then be performed on the quaternary salt to change the substituent or to form the bipyridyl coupling and the resultant salt dequaternized with a caustic material, such as sodium hydroxide, to produce a second pyridine or a bipyridine base.Type: GrantFiled: December 15, 1977Date of Patent: June 12, 1979Assignee: Reilly Tar & Chemical CorporationInventors: Thomas D. Bailey, Charles K. McGill