Reilly Industries, Inc.

Reilly Tar and Chemical Corporation

Gerald L Goe

Eric F Scriven

James G Keay

Edward E Sowers

Donald W McQuigg

Michael L Prunier

Thomas D Bailey

Charles R Marston

Steven J Quimby

James R Beadle

Ramiah Murugan

Charles K McGill

Robert D Davis

Angela R Sherman

Lowell M Huckstep

Disclosed are preferred processes for producing .alpha.-2-pyridyl.alpha.-aryl carbinol or .alpha.-4-pyridyl .alpha.-aryl carbinol compounds.

Processes for producing .alpha.-pyridyl carbinols

A latent curing agent for an epoxy resin comprising boron trifluoride on a cross-linked polymer support having at least 10% by weight of pendant pyridine groups. The polymer support is preferably about 25% to 40% cross-linked, and preferably in the form of porous, macroreticular beads having average diameters of less than 30 .mu.m. The combination of this latent curing agent admixed with an epoxy resin is also disclosed, as is the process for making and using the same.

Vinylpyridine polymer support complexed with boron trifluoride

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.

Processes for the synthesis of unsymmetrical secondary amines

Processes for the synthesis of imines, aldehydes, and unsymmetrical

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.

4-(N-benzyl-N-methylamino)pyridine acid salts and use in preparation of

An improved Monsanto-type process for acetic acid preparation and a heterogeneous-supported catalyst for accomplishing the same, comprising reacting methanol with carbon monoxide under pressure of about 65-80 Bar and temperature of about 170.degree.-200.degree. C. in the presence of methyl iodide and a catalyst comprising an insoluble polymer having pendant free base, N-oxide or quaternized pyridine groups supporting a rhodium species loaded to less than about 10 weight percent (expressed as metal) of the polymer component.

Process for acetic acid preparation and heterogenous catalyst for same

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.

High temperature process for selective production of 3-methylpyridine

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.

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.

Process for the synthesis of 4-amino-1,2,4-(4h)triazole derivatives

A process for dealkylating the 2-position on a trisubstituted pyridine derivative having the formula ##STR1## where R.sub.1 is a straight chain alkyl group from about C.sub.2 -C.sub.5 and where R.sub.2 and R.sub.3 are alkyl, aryl or aralkyl groups up to about C.sub.10, comprising the step of reacting said pyridine derivative at reflux with excess sulfur. Of particular note is the preparation of 2,3,5-trimethylpyridine including the initial preparation of its 2-ethyl precursor by the Chichibabin reaction of propionaldehyde and ammonia.

Process for preparing 2-methyl-3,5-dialkylpyridines by dealkylation with

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.

Process and catalyst for the preparation of 2,2'-bipyridyls

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.

Insoluble complex oxidation catalysts

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.

A new polymer composition comprised substantially of monomeric units having the formula ##STR1## or its acid salt, wherein R.sub.1 is an alkyl group having from 1 to about 20 carbon atoms or an arylalkyl group having from 7 to about 12 carbon atoms, and R.sub.2 is hydrogen or an alkyl group having from 1 to about 10 carbon atoms. A process for preparing the new polymer comprising the step of hydrogenating the quaternary salt of the pyridine precursor of the polymer under mild reaction conditions and in the presence of a hydrogenation catalyst selected from the Group VIII metals. A further step for preparing the free base polymer from the acid salt by reacting the same under mild conditions with a basic material such as sodium hydroxide.

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Greenwood, IN, United States of America

Gerald L Goe