Allied Corporation

Allied Chemical Corporation

Other

Alliedsignal Inc.

John H Bonfield

Harry E Ulmer

Donald Pickens

James T Yardley

Charles J Cole

Morris B Berenbaum

Andiappan K Murthy

Frederick R Hopf

Paul W Harris

Thomas P Izod

Karen M Bland

Stylianos Sifniades

Stephen E Belsky

Bela I Karsay

A new class of sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazole compounds and method for using them and other sulfonated hydroxyaryl benzotriazoles on nylon fibers to improve stain resistance and dye lightfastness has been discovered. A process is provided for improving stain resistance of nylon fibers by treatment with sulfonated aromatic-formaldehyde condensate and fluorinated dry soil resist agents.

Sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazoles and/or sulfonated

A vapor phase synthesis of hexafluoroisobutylene, which comprises contacting in the vapor phase in a catalyst zone, B, of a reactor hexafluoropropylene oxide with a fluorinated catalyst such as fluorinated silica-alumina at a temperature of about 400.degree.-600.degree. C. for a residence time sufficient to form a vapor stream comprising hexafluoroacetone which is thereafter directly contacted in a heating zone of the reactor with a vapor stream comprising a keytone-generating compound such as acetic anhydride at a temperature of about 500.degree.-700.degree. C. for a residence time sufficient to form a stream comprising hexafluoroisobutylene, substantially-free of perfluoroisobutylene and recovering the hexafluoroisobutylene product is disclosed. A direct one reactor vapor phase synthesis of hexafluoroisobutylene which comprises (a) contacting, in the vapor phase, hexafluoropropene with less than a stoichiometric amount of oxygen required to convert substantially all the hexafluoroisopropene into hexafluoropropylene oxide in the presence of a fluorinated catalyst such as fluorinated silica-alumina at a temperature of about 400.degree.-600.degree. C. for a time sufficient to form a vapor stream comprising hexafluoropropylene oxide substantially-free of oxygen; (b) directly contacting said vapor stream, in a catalyst zone, B, containing a fluorinated catalyst which is preferably the same as used in catalyst zone, A, at a temperature of about 400.degree.-650.degree., preferably about 500.degree.-650.degree. C. for a time sufficient to form a vapor stream comprising hexafluoroacetone; (c) directly contacting the vapor stream comprising hexafluroacetone with a vaporized compound such as acetic anhydride at a temperature of about 500.degree.-700.degree. C., preferably about 600.degree. C. for a time sufficient to form a vapor stream comprising hexafluoroisobutylene, substantially-free of perfluoroisobutylene; and (d) recovering hexafluoroisobutylene is also disclosed.

Vapor phase synthesis of hexafluoroisobutylene

An improved process for preparing formaldoxime trimer is provided in which loss of the product is minimized and the prior art problems of long retention times to afford precipitation of the trimer which is difficult to filter and which occludes the undesirable salt of the acid that is difficult to remove. The method disclosed involved oximation of paraformaldehyde using dehydroxylamine sulfate and ammonia gas followed by steam stripping to recover formaldoxime and separate trimerization thereof followed by filtration recovery and drying. The formaldoxime trimer is produced in essentially quantitative yield and proceeds specifically by a procedure of steam stripping out the formaldoxime monomer from the synthesis liquor and allowing separate trimer formation and recovery. The product is free from inorganic salts and the mother liquor with formaldoxime monomer content, resulting from its recovery by filtration, does not represent a yield loss in that it is recyclable to the next synthesis reaction.

Method of preparing formaldoxime trimer

Crude hexafluoroacetone containing as impurities nitrogen oxides and sulfur dioxide is purified by admixing with water to form an aqueous solution, admixing the aqueous solution with concentrated sulfuric acid or oleum to form a vapor and scrubbing the vapor with liquid concentrated sulfuric acid to produce purified anhydrous hexafluoroacetone. The sulfur dioxide and nitrogen oxides interact with the aqueous solution and concentrated sulfuric acid so as not to be found in the purified product, thus obviating the need for a neutralization step.

Purification of crude hexafluoroacetone containing nitrogen oxides and

A mixture of ketoxime such as methyl ethyl ketone oxime (MEKO), an inorganic acid such as sulfuric acid and optionally water is fed to an intermediate point of a fractional distillation column. Steam is fed to the base of the column and operating conditions are sufficient to produce the corresponding ketone (e.g. methyl ethyl ketone) or its water azeotrope as the overhead product and the corresponding hydroxylammonium salt (e.g. the sulfate) as the bottoms. Crystallization of the salt from the bottoms leaves a mother liquor which may be recycled to a reboiler from which the steam is generated.

Continuous hydrolysis of ketoxime

Acetaldehyde oxime, a commercially useful intermediate in the production of pesticides, is prepared by oximating acetaldehyde with an aqueous hydroxylamine-containing solution to form an aqueous oximation reaction mixture and recovering acetaldehyde oxime from the aqueous oximation reaction mixture by distilling a mixture of acetaldehyde oxime and water directly from the aqueous oximation reaction mixture.

Production of acetaldehyde oxime

In the halogenation under reflux conditions of an unhalogenated aldehyde of the formula ##STR1## with Cl.sub.2, Br.sub.2 or I.sub.2, the aldehyde and halogen are continuously fed into a reactor at a molar ratio of halogen to unhalogenated aldehyde between about 0.8:1 and about 1.1:1 and water is continuously fed into the unhalogenated reactor at a rate of between about 1% and about 20% by weight of aldehyde. The product .alpha.-haloaldehyde is thiohydrocarbylated and then oximated to form a 2-hydrocarbylthioaldoxime of the formula ##STR2## with improved yield and quality because of the improved yield and quality of unhalogenated .alpha.-haloaldehyde. An exemplary process includes the chlorination of isobutyraldehyde (IBA) to form .alpha.-chloroisobutyraldehyde (CIBA), the thiomethylation of CIBA to form 2-methyl-2 methylthio-propionaldehyde (MTIBA) and the oximation of MTIBA to form 2-methylthio-propionaldehyde oxime (aldicarb oxime or ADO).

Process for halogenation of aldehydes and production of oximes therefrom

In the halogenation under reflux conditions of an aldehyde of the formula ##STR1## with Cl.sub.2, Br.sub.2 or I.sub.2, the aldehyde and halogen are continuously fed into a reactor at a molar ratio of halogen to aldehyde between about 0.8:1 and about 1.1:1 and water is continuously fed into the reactor at a rate of between about 1 and about 20% by weight of aldehyde. The product .alpha.-haloaldehyde is thioalkylated and then oximated to form a 2-hydrocarbylthioaldoxime of the formula ##STR2## with improved yield and quality because of the improved yield and quality of .alpha.-haloaldehyde. An exemplary process includes the chlorination of isobutyraldehyde (IBA) to form .alpha.-chloroisobutyraldehyde (CIBA), the thiomethylation of CIBA to form 2-methyl-2 methylthio-propionaldehyde (MTIBA) and the oximation of MTIBA to form 2-methylthio-propionaldehyde oxime (aldicarb oxime or ADO).

An improved process for producing ammonium nitrite in high yield which comprises contacting a gaseous stream containing nitric oxide and oxygen with an aqueous solution containing a basically reacting ammonium compound in the presence of free carbon dioxide.

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Basking Ridge, NJ, United States of America

John H Bonfield