It is known that ditertiary butyl peroxide is a minor constituent of the reaction product when tertiary butyl hydroperoxide is thermally or catalytically decomposed to form tertiary butyl alcohol. Ditertiary butyl peroxide is a valuable commercial product used, for example, as a high temperature free radical initiator in chemical reactions. U.S. Pat. Nos. 4,810,809 and 4,900,850, to Sanderson et al. disclose methods which can be used to recover purified ditertiary butyl peroxide from a reaction product formed by the thermal or catalytic decomposition of tertiary butyl hydroperoxide.
In "Organic Peroxides" edited by Daniel Swern (Wiley Interscience, a Division of John Wiley & Sons, New York), in Vol II, page 157, it is stated that the metal-ion-catalyzed decomposition of primary hydroperoxide yields mainly alcohols, aldehydes and carboxylic acids.
In U.S. Pat. No. 2,854,487, Quin discloses the hydrogenation of hydrocarbon peroxides in the presence of hydrogen and palladium on activated alumina to provide carbinols.
In U.S. Pat. No. 3,474,151 it is disclosed that tertiary butyl alcohol starts to dehydrate at 450.degree. .F and to decompose at a "rapid rate" at temperatures above 475.degree. F. It was disclosed that residual quantities of hydroperoxide contaminants present in tertiary butyl alcohol could be thermally decomposed by heating the contaminated tertiary butyl alcohol at a temperature of 375.degree. F. to 475.degree. F. for about 1 to 10 minutes.
In U.S. Pat. No. 4,294,999 there is disclosed a process wherein isobutane is oxidized in a pressured reactor in the presence of solubilized molybdenum catalyst to provide a mixture of tertiary butyl alcohol, tertiary butyl hydroperoxide, methanol, acetone, and other oxygen-containing compounds. The tertiary butyl hydroperoxide is thermally decomposed under pressure at about 280.degree. F. to provide a tertiary butyl alcohol product containing only residual quantities of tertiary butyl hydroperoxide which are then decomposed in accordance with Grane, U.S. Pat. No. 3,474,151, by heating the tertiary butyl alcohol at 375.degree. to 475.degree. F. for about 1 to 10 minutes. Heating tertiary butyl alcohol containing small amounts of peroxides at high temperatures for even short periods of time to remove the peroxides produces undesirable products such as isobutylene.
In U.S. Pat. No. 4,551,553 to Taylor et al. there is disclosed a process for the formation of alcohols such as tertiary butyl alcohol by the catalytic decomposition of an organic hydroperoxide such as tertiary butyl hydroperoxide using a binary catalyst composed of a mixture of a ruthenium compound with a chromium compound. It is stated that the use of the binary catalyst eliminates the need for stabilizing ligands.
Sanderson et al. disclose the use of a variety of catalysts for the decomposition of tertiary butyl hydroperoxide in a series of U.S. patents, including a catalyst composed of unsupported nickel, copper, chromia and iron (U.S. Pat. No. 4,704,482), a catalyst composed of iron, copper, chromia and cobalt (U.S. Pat. No. 4,705,903), a catalyst composed of a base treated hydrogenation catalyst from Groups VIB or VIIIB of the Periodic Table (U.S. Pat. No. 4,742,179), a catalyst consisting essentially of nickel, copper, chromium and barium (U.S. Pat. No. 4,873,380), a catalyst composed of a metal phthalocyanine promoted with a rhenium compound (U.S. 4,910,349), a catalyst composed of a base promoted metal phthalocyanine compound, (U.S. Pat. No. 4,912,269), a catalyst composed of a soluble ruthenium compound promoted with a bidentate ligand (U.S. Pat. No. 4,912,033), a catalyst composed of a metal porphine such as iron (III) or manganese(III) promoted with an alkyl thiol or an amine, a catalyst composed of an imidazole promoted metal phthalocyanine compound (U.S. Pat. No. 4,912,266), (U.S. Pat. No. 4,922,034), a catalyst composed of a metal phthalocyanine promoted with a thiol and a free radical inhibitor (U.S. Pat. No. 4,922,035), a catalyst composed of a borate promoted metal phthalocyanine, (U.S. Pat. No. 4,922,036) or a catalyst composed of a soluble ruthenium compound and an iron compound such as an acetate, a borate, a bromide, a chloride, a 1,3-propanedionate, a 2-ethyl-hexanoate, an iodide, a nitrate, a 2,4-pentanedionate, a perchlorate or a sulfate (U.S. Pat. No. 5,025,113).
In U.S. Pat. No. 5,345,009, to Sanderson et al., there is disclosed the conjoint production of tertiary butyl alcohol and ditertiary butyl peroxide from tertiary butyl hydroperoxide.
In U.S. Pat. No. 5,288,919, there is disclosed a process for the preparation of dialkyl peroxide which comprises reacting an alcohol (ROH) or an olefin having the formula ##STR1## and mixtures in the liquid phase with a hydroperoxide (R.sub.1 OOH) in the presence of an inorganic heteropoly or isopoly acid catalyst.
A process is described in U.S. Pat. No. 5,312,998, where isobutane oxidate is reacted in the presence of a water soluble acid catalyst. A reaction mixture is formed which is separated into two phases, an aqueous phase and an organic phase which contains the ditertiary butyl peroxide which is subjected to a series of separation steps to recover the product.
It would be desirable if there were an improved method available for selectively generating ditertiary butyl peroxide which demonstrated improved yields of di-t-butyl peroxide and a simpler means of recovery, preferably through the use of a heterogeneous, solid acid catalyst.
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