Gerald L. Goe - Greenwood IN Eric F. V. Scriven - Greenwood IN James G. Keay - Indianapolis IN Lowell M. Huckstep - Plainfield IN
Assignee:
Reilly Tar and Chemical Corporation - Indianapolis IN
International Classification:
C07D24914
US Classification:
5482656
Abstract:
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.
Gerald R. Goe - Greenwood IN Charles K. McGill - Indianapolis IN Angela R. sherman - Lebanon IN
Assignee:
Reilly Industries Inc. - Indianapolis IN
International Classification:
C07D40104
US Classification:
546260
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.
High Temperature Process For Selective Production Of 3-Methylpyridine
Gerald L. Goe - Greenwood IN Robert D. Davis - Indianapolis IN
Assignee:
Reilly Industries - Indianapolis IN
International Classification:
C07D21309
US Classification:
546251
Abstract:
A process for the selective production of 3-methylpyridine in high yield comprising the step of contacting a vaporized feed stream containing 2-methyl-1,5-pentanediamine with a metal-oxide catalyst of other than an alkali metal at a temperature of about 500. degree. -600. degree. C. for a contact time of less than about 30 seconds. The catalyst may be on a suitable heterogeneous support, and additives in the feed stream may include 3-methylpiperidine as well as water, hydrogen, ammonia, or nitrogen or some other inert gas. A fluid-bed reactor is preferred, with recycling of by-product and continuous effective runs without catalyst regeneration being accomplished at the stated temperatures.
Processes For The Synthesis Of Imines, Aldehydes, And Unsymmetrical Secondary Amines
Gerald L. Goe - Greenwood IN James G. Keay - Indianapolis IN Eric F. V. Scriven - Greenwood IN Michael L. Prunier - Vernon IL Steven J. Quimby - Carmel IN
Assignee:
Reilly Industries, Inc. - Indianapolis IN
International Classification:
C07D21324
US Classification:
546329
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.
Improved Process And Catalyst For The Preparation Of 2,2' Bipyridyls
Gerald R. Goe - Greenwood IN Charles K. McGill - Indianapolis IN Angela R. Sherman - Lebanon IN
Assignee:
Reilly Industries, Inc. - Indianapolis IN
International Classification:
C07D40104
US Classification:
546260
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.
Processes For The Synthesis Of Unsymmetrical Secondary Amines
Gerald L. Goe - Greenwood IN James G. Keay - Indianapolis IN Eric F. V. Scriven - Greenwood IN Michael L. Prunier - Vernon IL Steven J. Quimby - Carmel IN
Assignee:
Reilly Industries, Inc. - Indianapolis IN
International Classification:
C07D21324
US Classification:
546329
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.
4-(N-Benzyl-N-Methylamino)Pyridine Acid Salts And Use In Preparation Of Polymer-Supported Catalysts
Donald W. McQuigg - Mooresville IN Edward E. Sowers - Mooresville IN Gerald L. Goe - Greenwood IN Eric F. V. Scriven - Greenwood IN James G. Keay - Indianapolis IN
Assignee:
Reilly Industries, Inc. - Indianapolis IN
International Classification:
C07D21172
US Classification:
546304
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.
Gerald L. Goe - Greenwood IN Thomas D. Bailey - Greenwood IN James R. Beadle - Plainfield IN
Assignee:
Reilly Tar and Chemical Corp. - Indianapolis IN
International Classification:
B01J 3104 B01J 3106
US Classification:
502159
Abstract:
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 Tetralino. 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.