Allied Chemical Corporation

Allied Corporation

Martin A Robinson

Richard E Eibeck

Francis E Evans

Louis G Anello

Michael Van Der Puy

Morris B Berenbaum

Henry R Nychka

Robert E Booth

Charles J Lind

Edward Stephen Jones

Timothy R Demmin

Larry L Hendrickson

David S Soriano

David J Friedland

Eugene B Recla

Ralph C Gatrone

Floyd L Tewksbury

Charles J Felice, Jr

Michael Van De Puy

John B Hino

Novel .beta.-oximinoalkylphosphonic acid ester derivatives of general formula B are prepared from the corresponding .alpha.-halo oxime A: ##STR1## wherein R.sup.1 is a substituent selected from the group consisting of H and C.sub.1 -C.sub.20 alkyl, cycloalkyl and aryl substituents;

.beta.-Oximinoalkylphosphonic acid esters

The invention relates to novel urease inhibited fertilizer compositions containing urea and a urease inhibiting amount of one or more organo boron acid compounds, and to a method and composition for inhibiting the catalytic activity of urease through use of such compounds.

Urease inhibited urea based fertilizer compositions containing organo

A process for the preparation of perhaloalkanoyl chloride is disclosed which comprises reacting 1,1,1-trichloroperfluoroalkane, with a sulfur trioxide-containing compound selected from the group consisting of oleum sulfur trioxide and stabilized sulfur trioxide in the presence of catalytic amounts of a halogen catalyst selected from the group consisting of iodine, bromine, iodine monobromide and iodine monochloride and bromine monochloride wherein the 1,1,1-trichloroperhaloalkane is a straight or branched chain acyclic organic compound having 2 to 8 carbon atoms and having at least one trihalomethyl group wherein at least one halo atom is fluorine and having the remaining carbon atoms substituted by F, Cl, Br or I atoms.

Conversion of 1,1,1-trichloroperhaloalkanes into perhaloalkanoyl

Octafluoropropane or perfluoropropane is produced by introducing fluorine into an elongated inner zone surrounded by a porous member which is substantially resistant to fluorine corrosion and introducing a three carbon compound which is propane, a partially fluorinated propane, propene, a partially fluorinated propene, hexafluoropropene or mixtures thereof outside the porous member. When the porous member is metal, a perfluorinated diluent is used. When the porous member is fused alumina, conventional diluents such as nitrogen, or even no diluent may be employed.

Production of perfluoropropane

A process for the preparation of trifluoroacetyl fluoride is disclosed, which comprises reacting, in the liquid phase, hexafluorothioacetone dimer in an aprotic solvent with at least a catalytic amount of an alkali metal fluoride in the presence of an oxidizing agent selected from the group consisting of Ag.sub.2 O, oxides of Pb, Sn, Ni, Co and Fe and M.sub.2 S.sub.2 O.sub.8 wherein M is an alkali metal. The preferred aprotic solvent is dimethylformamide; the preferred alkali metal fluoride is KF; and the preferred oxidizing agents are NiO, PbO.sub.2, and M.sub.2 S.sub.2 O.sub.8 wherein M is Na or K.

Synthesis of trifluoroacetyl fluoride

A process for the conversion of boron trifluoride dimethyl ether complex to boron trifluoride dialkyl ether complex substantially free of dimethyl ether impurities, which comprises reacting the boron trifluoride-dimethyl ether complex, in the liquid phase, in the presence of dialkyl ether wherein at least one of the alkyl groups contains at least two carbon atoms, in a restricted vapor equilibration region, while simultaneously sweeping the said vapor equilibration region with a substantially inert gas, and heating to distill off the dimethyl ether. High purity of the boron trifluoride dialkyl ether complex is attained with this method, with only minimal traces of the boron trifluoride dimethyl ether complex, dimethyl ether remaining. The preferred product is boron trifluoride diethyl ether.

Process for the conversion of boron trifluoride dimethyl ether complex

A process for the preparation of perhaloalkanoyl chloride is disclosed which comprises reacting 1,1,1-trichloroperfluoroalkane, with a sulfur trioxide-containing compound selected from the group consisting of oleum sulfur trioxide and stabilized sulfur trioxide in the presence of catalytic amounts of a halogen catalyst selected from the group consisting of iodine, bromine, iodine monobromide and iodine monochloride and bromine monochloride. The preferred product is trifluoroacetyl chloride.

Process for the preparation of perhaloalkanoyl chloride

A process for the preparation of hexafluoroacetone which comprises contacting, in the liquid phase, hexafluorothioacetone dimer in the presence of an aprotic solvent containing a catalytic amount of an alkali metal fluoride with a gaseous oxidant selected from the group consisting of air, O.sub.2, O.sub.3, NO.sub.2 and NO is disclosed. The preferred aprotic solvent is dimethylformamide, and the preferred gaseous oxidant is O.sub.2.

Liquid phase synthesis of hexafluoroacetone

The production of hexafluoroacetone by liquid phase reaction, at elevated temperatures, from hexafluorothioacetone dimer in an aprotic solvent containing an effective amount of an alkali metal fluoride with at least about a stoichiometric amount of an oxidizing agent selected from the group consisting of HgO, Ag.sub.2 O, Cu.sub.2 O, CuO, P.sub.2 O.sub.5, MIO.sub.3 and MIO.sub.4 wherein M is an alkali metal or alkaline earth metal. HgO and MIO.sub.3 are the preferred oxidizing agents; KIO.sub.3 is most preferred.

Preparation of hexafluoroacetone from hexafluorothioacetone dimer

Certain metals, and especially uranium, are recovered from an organic solvent by stripping with an aqueous solution containing polymeric phosphates under conditions in which the polymeric phosphate does not quickly hydrolize and metal preferentially dissolves in the aqueous solution. The metal may then be recovered from the aqueous solution by hydrolizing the polymeric phosphates and either precipitating the metal or reextracting the metal at higher concentrations with an organic solvent containing extractants.

Stripping metals from organic solvent with aqueous solution of polymeric

Sulfuric acid contaminated with boron and fluoride values such as the waste acid of a boron trifluoride process is purified by contacting the contaminated acid with an inert gas to desorb boron trifluoride, and the inert gas is stripped by contacting with an absorbing liquid including concentrated sulfuric acid. Fluosulfonic acid is added to contaminated sulfuric acid at levels approximately three times the molar values of boric acid contaminant as an agent to spring non-volatile boron values. The absorption of boron trifluoride into the absorbing sulfuric acid is improved when it contains boric acid. Preferably the contaminated sulfuric acid to be purified is one portion of the waste liquid and the absorbing liquid is another portion of the waste liquid of a boron trifluoride manufacturing process. Boric acid is added to the absorbing liquid, then boron trifluoride is stripped from the inert gas and absorbed into the absorbing liquid. The absorbing liquid along with stripped boron trifluoride is recycled to a boron trifluoride manufacturing process. The inert gas can be recycled to the desorbing step.

Purification of boron-containing sulfuric acid

When saturated with boron trifluoride, certain polyhydric alcohols form adducts which catalyze hydrocarbon alkyl transfer reactions for which boron trifluoride is catalytic. The adduct is recovered from the reaction mixture and recycled, greatly reducing boron and fluoride values in the product and in any effluent. Examples include propylation of toluene in the presence of a recycled adduct of boron trifluoride with mannitol or sorbitol, and the oligomerization of decene by a recycled adduct of boron trifluoride with mannitol or butanediol. Some of the catalysts become viscous on cooling and are thus more easily separated from the reaction products which remain in a separate liquid phase.

Recyclable boron trifluoride catalyst and method of using same

High purity tetrahydrocarbylammonium tetrahydridoborates are prepared under anhydrous conditions by reacting tetrahydrocarbylammonium salts with at least 8% molar excess of an alkali metal hydroxide in the presence of ethanol to produce the corresponding tetrahydrocarbylammonium hydroxides and alkali metal salts, removing the alkali metal salts and adding an alkali metal borohydride to the solution to produce the corresponding tetrahydrocarbylammonium tetrahydridoborates and alkali metal hydroxides.

Preparation of high purity tetrahydrocarbylammonium tetrahydridoborates

When saturated with boron trifluoride, certain polyhydric alcohols form adducts which catalyze reactions for which boron trifluoride is catalytic. The adduct is recovered from the reaction mixture and recycled, greatly reducing boron and fluoride values in the product and in any effluent. Examples include propylation of toluene in the presence of a recycled adduct of boron trifluoride with mannitol or sorbitol.

Fluoroorganic compounds are prepared by reacting a haloorganic starting material in which at least one halo atom is replaceable with a fluorine atom by metathetical exchange, with calcium fluoride in the presence of a crown ether and an anhydrous, polar, basic organic solvent which complexes with the calcium ion and contains no --OH groups, at a temperature and for a period of time adequate to effect fluorination.

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East Amherst, NY, United States of America

Martin A Robinson