The B. F. Goodrich Company

Ronald M Kovach

John T Lai

Angelo J Magistro

Pyong-Nae Son

Pyong N Son

George Kletecka

Charles P Jacobs

Joseph A Cowfer

Dane E Jablonski

Victor L Ledesma

The prior art solvent process for the manufacture of an oxo-piperazinyl triazine (PIP-T) compound required carrying out the reaction between an appropriately hindered cyclic amine and cyanuric chloride in the presence of caustic catalyst, in alkylbenzene solution, typically toluene. The chloride ions generated during the reaction, in presence of water present in the reaction zone, produced serious corrosion and resulted in off-color product which had a melt absorptivity greater than 3.5 mL/gm.cm. This 'color' in the product made the product generally unmarketable. Another process to make a PIP-T termed 'the solventless' process used no toluene solvent, and no caustic but required such a very large excess of amine that the catalytic function of the amine.HCl salt went unnoticed. In the novel process, referred to as the 'hybrid' process, this catalytic function allows the use of only as much toluene in the reactor as is needed to keep the product formed and the excess amine in solution, and the use of less than a two-fold molar excess over the molar amount to displace each chlorine atom of the cyanuric chloride. The result is exceptionally high purity and yield with color no greater than that which the marketplace accepts.

Hybrid process for preparing a tri-substituted triazine

A staged process is disclosed for forming a tri-substituted triazine ring in which the substituents are cyclic amines referred to as hindered amines. A prior art process for making such amines in a reaction mixture of aqueous and organic phases has been modified to produce a stabilizer with desirable whiteness, at the same time avoiding the loss of the cyclic amine reactant which is water-soluble. Conversion of the amine to yield at least 90% of the tri-substituted product having at least 90% purity allows the reaction to be commercially significant despite the high cost of the reactants. The staged process is preferably conducted in two sequences in two reactors, with an intermediate step in which the aqueous saline and basic solution from the first sequence is withdrawn. In the first sequence, a mono-chloro intermediate ('MCI') is formed at ambient temperature, but below 100.degree. C. to yield a colored solution. Flowing only the organic phase to the second reactor which must be pressurized, allows use of an economical reactor. In the second sequence, preferably in a separate reaction zone, reacting 3 moles of MCI with no more than 3.5 moles of a third amine, yields the tri-substituted product which is formed at below 200.degree. C. but in excess of 125.degree. C. Only a small portion of the molar excess of amine used in the second sequence need be discarded. The time required to run the reaction in two stages is less than required to run it in a single sequence. Further saving in time is effected by using a phase transfer catalyst.

Process for the manufacture of a tri-substituted triazine stabilizer

Certain polysubstituted piperazinones (PSP) having two or three methylene groups linking the N.sup.1 atom of the ring to the N atom of a terminal amine group, are found to be peculiarly prone to decomposition when subjected to elevated temperature after being contacted with water, and sensitive to the amount of base used in the base-induced ketoform reaction which generates the PSP represented by the structure ##STR1## These PSP are therefore produced by a modification of the ketoform reaction under essentially anhydrous conditions, using enough ketone to dissolve the PSP formed and a molar ratio of solid alkali metal hydroxide/diamine reactant in the range from at least 5 but less than 7. The PSP produced is recovered as a solution in the ketone, without contacting the PSP with water. The PSP product obtained after the ketone is distilled, is essentially pure.

Process for desensitizing a 1-(alkylamino)alkyl-polysubstituted

A method is disclosed for using a pendulum viscometer having damped torsional oscillations, in a laboratory catalytic fluid-bed reactor, to monitor a propensity to stick which is exhibited by certain supported catalysts. A fluid-bed of such catalysts has been found to become suddenly more sticky just before a point at which a change in pressure drop across the fluid-bed can be measured due to a process 'upset'. At this point ('the inversion point'), the upset is usually irremediable. The method includes correlating data on catalyst stickiness from a laboratory reactor operating at atmospheric pressure, with an expected level of catalyst stickiness in a commercial reactor operating at elevated pressure. A pendulum viscometer and related auxiliary apparatus is disclosed for magnetically and electrically measuring and recording the rate at which the pendulum's torsional oscillations are damped. Frequent measurements are made during normal operation of the fluid-bed to determine its stickiness (as evidenced by the rate at which the pendulum's torsional oscillations are damped) relative to the stickiness at the inversion point. Operation of the fluid-bed under conditions for which measured rates of damping are predeterminedly lower than the rate near the inversion point, assures operation of the fluid-bed reactor at maximum efficiency.

Growing community of inventors

Avon Lake, OH, United States of America

Ronald M Kovach