Patents Assigned to Reilly Tar & Chemical Corporation
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Patent number: 5099028Abstract: A process for preparing a 4-amino-1,2,4-(4H)triazole derivative compositions having the formula ##STR1## wherein R is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms, which alkyl group can be additionally substituted by one or more aryl, heteroaryl, hydroxy, or alkenyl substituents, comprising the step of reacting hydrazine or an aqueous hydrazine solution with a carboxylic acid having the formula RCO.sub.2 H in the presence of an insoluble polymer containing acidic functional groups sufficiently strong to cause the reaction to proceed under mild conditions to produce a product of high yield and purity.Type: GrantFiled: December 19, 1989Date of Patent: March 24, 1992Assignee: Reilly Tar and Chemical CorporationInventors: Gerald L. Goe, Eric F. V. Scriven, James G. Keay, Lowell M. Huckstep
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Patent number: 4839323Abstract: Insoluble complex oxidation catalysts comprising chromium salts bound on an insoluble polymer supports having pendant pyridine groups, that are useful in oxidation reactions such as Tetralin.RTM. to .alpha.-tetralone, ethylbenzene to acetophenone, and 2-methyl-5-ethylpyridine to 2-methyl-5-acetylpyridine. Also disclosed are processes for accomplishing such oxidations utilizing such catalysts.Type: GrantFiled: November 2, 1987Date of Patent: June 13, 1989Assignee: Reilly Tar & Chemical CorporationInventors: Gerald L. Goe, Thomas D. Bailey, James R. Beadle
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Patent number: 4695352Abstract: Electrochemical reductions of pyridine carboxamide bases performed by electrolysis in a divided flow cell utilizing an ion-exchange membrane at a high hydrogen-overvoltage cathode and in an aqueous or partly aqueous medium comprising a Lowry-Bronsted acid in at least a 1:1 equivalent ratio with the pyridine carboxamide base. A titanium salt catalyst and other means are disclosed to add selectivity to the reduction and improve yield of the amine or other desired reaction product. With all bases, significant advantages of a commercial and industrial nature are reported over prior art static, beaker cell technology.Type: GrantFiled: December 31, 1984Date of Patent: September 22, 1987Assignee: Reilly Tar & Chemical CorporationInventor: Joseph E. Toomey, Jr.
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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
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Patent number: 3979400Abstract: Pyridyl ketones are produced from substituted pyridines containing at least one lower alkyl group or aryl-methylene group connected to a carbon of the pyridine nucleus by a methylene radical of such group, by air oxidizing the pyridine in the liquid phase at elevated temperature, e.g., 200.degree. C., and pressure, e.g., 400 psig. The reaction is preferably carried out in the presence of an inorganic oxidation catalyst, such as a heavy metal or oxide or hydrated oxide or inorganic salt thereof, but with some pyridines, especially 2-substituted and 4-substituted pyridines, reaction occurs without a catalyst. The reaction mixture is fractionated to recover the pyridyl ketone and unreacted starting material.Type: GrantFiled: December 11, 1974Date of Patent: September 7, 1976Assignee: Reilly Tar & Chemical CorporationInventors: William H. Rieger, Ernest W. Crowe