Koppers Company, Inc.

Nicholas P Greco

David A Webb

Byung K Ahn

John J Kozak

Arsenic acid is formed from arsenous acid and water under oxygen pressure with catalytic amounts of nitric acid and a halide whereby the nitric oxide by-product is regenerated to nitric acid for contact with fresh arsenous acid.

Process for preparation of arsenic acid

2,6-dialkyl substituted phenols such as 2,6-ditertiary butylphenol are reacted with formaldehyde in methyl alcohol in the presence of an inert gas and a tertiary amine catalyst to produce a bis(3,5-di-t-butyl-4-hydroxybenzyl)ether; and the bis ether subjected to hydrogenolysis in the presence of a catalyst, a solvent and an amine to prepare a trisubstituted phenol such as 2,6-di-t-butyl-4-methyl-phenol.

Process for preparation of trisubstituted phenols

There is disclosed a process for removing tar bases and neutral oils from the Lurgi tar acids by treating the tar acids with aqueous sodium bisulfate to change the tar bases to salts and to hydrolyze the neutral oils to hydrolysis products and distilling the tar acids to obtain refined tar acid as the distillate while the tar base salts and neutral oil hydrolysis products remain as residue.

Refining lurgi tar acids

A process is disclosed for making resorcinol and substituted resorcinols by a first reaction step of vapor-phase cyclization of a delta-keto carboxylic acid ester over a carbon catalyst bed to form a 1,3-cyclic dione intermediate. The delta-keto ester is conveyed through the catalyst bed by a vaporized carrier characterized by being liquid at 25.degree. C. and having a sufficiently high boiling point that the vaporized carrier is easily condensable under ambient conditions. In a second reaction step, a liquid solvent containing the 1,3-cyclic dione intermediate is contacted with a supported noble-metal catalyst to form resorcinol or a substituted resorcinol.

Preparation of resorcinol and substituted resorcinols by liquid-phase

A process is disclosed for making 1,3-cyclic diones by vapor-phase cyclization of delta-keto carboxylic acid esters over a carbon catalyst bed. The delta-keto ester is conveyed through the catalyst bed by a carrier gas characterized by being liquid at 25.degree. C. and having a sufficiently high boiling point that the carrier gas is easily condensable under ambient conditions. The delta-keto ester is highly soluble in the liquid carrier, while the cyclic dione product of the ester has very low solubility in the liquid carrier. Use of the described carrier in vapor-phase cyclization of delta-keto esters allows efficient separation of cyclic dione product and unreacted starting material from the carrier after the cyclization reaction.

Preparation of 1,3-cyclic diones by vapor phase cyclization of

Effluent containing cresols such as are contained in Lurgi tar acids are separated by preferentially treating the cresols with an aqueous alkali metal carbonate or bicarbonate at elevated temperature for a time sufficient to form the alkali metal salt of at least part of the cresols, but not so long as to form any appreciable alkali metal salt of 2,6-xylenol or o-ethylphenol. The water soluble alkali metal salts of cresols are then separated from the water insoluble phenols and said salts acidified to 'spring' the cresols and the water insoluble cresols separated from the aqueous solution.

Separation of phenols

Ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylphenols can be produced from phenolic compounds in good yields. The phenolic compound is reacted with an aldehyde having one to ten carbon atoms and a secondary aliphatic amine having a basic dissociation constant, pK.sub.b, of less than about 3.6 measured at 25.degree. C. The reaction is conducted in the liquid phase with at least a stoichiometric amount of the phenolic compound, the aldehyde and the secondary amine, or with an excess of the phenolic compound with the stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of around 0.degree. C. to about 25.degree. C., and the reaction produces an aminoalkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 120.degree. C. to about 140.degree. C. at a hydrogen pressure not greater than 150 psi to produce a mixture of ortho-monoalkylphenol, para-monoalkylphenol and 2,4- and 2,6-alkylphenol. These compounds are separated to produce ortho-monoalkylphenol, para-monoalkylphenol, 2,4-dialkylphenol and 2,6-dialkylphenol.

Process for alkylating phenolic compounds to produce ortho- and

Alpha-resorcylic acid is produced by the hydrolysis of 3,5-diamino benzoic acid in an aqueous solution of ammonium bisulfate. The reactants are contacted at an elevated temperature for a period of time sufficient to hydrolyze the 3,5-diamino benzoic acid to alpha-resorcylic acid and the alpha-resorcylic acid so produced is separated from the reaction mixture. The ammonium sulfate is regenerated to ammonium bisulfate by removing the water and thermally decomposing the by-product ammonium sulfate at an elevated temperature.

Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acid

An improved creosote wood preservative that has a light color and that forms a non-sticky crud deposit is prepared from a coal tar creosote. The coal tar creosote is reacted with one or more of the following groups of neutral compounds: paraformaldehyde, trioxane; or nitrobenzene, nitrotoluene, nitroxylene, tris (hydroxymethyl) nitromethane; or aluminum, zinc or sulfur, to produce a reacted creosote. This reacted creosote is distilled to yield a distillate, which is the improved creosote wood preservative, and a pitch residue.

Method for preparing an improved creosote wood preservative from a coal

An improved creosote wood preservative that has a light color and that forms a non-sticky crud deposit is prepared from a coal tar creosote. The coal tar creosote is distilled to an end temperature in the range of 395.degree. to 410.degree.C. at atmospheric pressure. This distillation produces a distillate and a pitch residue. The distillate is contacted with at least 1% by weight of one or more of the following caustic compounds: alkali metal alcoholates of alkali metal hydroxides to produce the improved creosote wood preservative. The pitch residue from distillation is recovered and it is utilized in the production of various pitch products or in combustion for its fuel value.

A catalyst for use in preparing p-aminophenol by catalytic hydrogenation of nitrobenzene in an acidic solution. The catalyst is either powdered molybdenum sulfide-on-carbon or powdered platinum sulfide-on-carbon.

Hydrogenation of nitrobenzene to p-aminophenol

Hydroquinone is made by electrolytically reducing nitrobenzene in an aqueous acid medium and thereafter maintaining the reaction medium containing the amino product, at a temperature of 200.degree. to 300.degree.C. for a sufficient time to hydrolyze the amino product to hydroquinone, and extracting the hydroquinone from the aqueous reaction medium.

Production of hydroquinone

Hydroquinone is made by contacting nitrobenzene in an aqueous acid medium with hydrogen at elevated temperatures and pressures in the presence of an acid resistant reducing catalyst until hydrogen absorption ceases, removing any unreduced nitrobenzene from the reaction medium, removing the catalyst from the reaction medium, thereafter maintaining the reaction medium containing the hydrogen reduction product at a temperature of 200.degree. to 300.degree.C. for a sufficient time to hydrolyze the reduction product to hydroquinone, and extracting the hydroquinone from the aqueous reaction medium.

Methyl resorcinols are produced by the hydrolysis of toluene diamines in an aqueous excess of ammonium bisulfate. The reactants are contacted at an elevated temperature for a period of time sufficient to hydrolyze the toluene diamines to methyl resorcinols. The methyl resorcinols so produced are separated from the reaction mixture. The ammonium sulfate is regenerated to ammonium bisulfate by removing the water and thermally decomposing the by-product ammonium sulfate at an elevated temperature.

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Pittsburgh, PA, United States of America

Nicholas P Greco