Solvay Interox Gmbh

Interox Chemicals Limited

Solvay (societe Anonyme)

John P Sankey

William R Sanderson

Alun P James

Craig W Jones

Graham R Horne

Graham Carr

Paul Richard Harrison

Paul John Middleton

Sharon Lesley Wilson

Kelly J Morton

Robert Johnson

Inderbir K Tranter

Valerie Lawton

Joseph M Schofield

A Pryce James

Alasdair Stuart Martin

Johnathan McAdam

The invention concerns compound HO&mdash;(CH ) &mdash;COOOH or 6 -hydroxypercaproic acid, its preparation process, i.e. from &egr;-caprolactone, aqueous compositions thereof and their use as disinfectant or bleaching agents.

Peroxy-carboxylic acid and aqueous compositions thereof

Storage stable aqueous acidic solutions, often having a pH of up to 1 containing an ester peracid and/or an acid peracid can be obtained by reacting a diester satisfying the general formula R,&mdash;O&mdash;CO&mdash;R,&mdash;CO&mdash;O&mdash;R,in which R,and R,each represents a alkyl group containing from 1 to 4 carbon atoms which may the same of different and R,represents an aliphatic alkylene group optionally unsaturated which may be linear or branched containing from 2 to 6 carbon atoms with aqueous hydrogen peroxide in the presence of an acid, such as sulphuric acid and permitting the compositions to progress towards equilibrium concentrations. By starting with a diester, perhydrolysis generates an ester peracid which is a particularly effective peracid. The process can be controlled to produce solutions containing a high peracid content and within a wide range of ratios of ester peracid to acid peracid.

Percarboxylic acid solutions

Detergent builders/activators derived from the oxidation and acylation

Percarboxylic acids

Peracid compounds

Oxidation process

A one pot process for the perfluoroalkylation and/or perfluoroacyloxylation of organic substrates is provided. The process comprises contacting a substrate with a perfluoroalkanoic anhydride in the presence of an inorganic peroxygen compound at a temperature of greater than 10.degree. C. Substrates that can be perfluoroalkylated and/or perfluoroacyloxylated include alkylbenzenes, halogenated aromatic compounds, alkoxybenzenes, aryl benzenes, and aromatic and aliphatic disulphides. Preferably, the perfluoroalkanoic anhydride is trifluoroacetic anhydride and the inorganic peroxygen compound is sodium percarbonate.

Process for the introduction of fluoro substituents

Peroxycompounds

The compound 6,6'-terephthal-di(amidoperoxyhexanoic) acid is disclosed.

Peroxyacid manufacture

Peroxycarboxylic acids and compositions containing such

The incorporation of many percarboxylic acids in household formulations is precluded from by adverse physicochemical properties, such as a propensity to decompose too quickly during storage or explode on impact or when subjected to pressure, though otherwise they would be effective disinfectants and bleaching agents, especially at hand-hot temperatures. The invention provides a stable and effective selection of organic percarboxylic acids which satisfy one or other of the general formulae (1) or (2):

Hitherto processes proposed in recent years for preparing esters of phenol sulphonate salts by reaction between a carboxylic acid chloride and a phenol sulphonate salt place considerable emphasis upon dehydrating the reactants before they are brought into contact in an organic solvent reaction medium. The present invention avoids the problems of employing non-aqueous solvents by carrying out the reaction under aqueous conditions but with controlled alkalinity and water content, especially at a base to phenol sulphonate mole ratio of from 1.3:1 to 1.6:1 and a total water to phenol sulphonate (as the anhydrous material) of not more than 4.5:1. The reaction advantageously employs in preference only a small molar excess of carboxylic acid chloride over the phenol sulphonate and preferably has a reaction temperature controlled to below 30.degree. C., expecially 5.degree. to 20.degree. C. In a further improvement to the process, the difficulty of enhanced contamination with benzoic acid in the products can be ameliorated by employing a small but effective amount of a surfactant, especially an alcohol ethoxylate, in the reaction mixture. The process is especially well suited to making sodium benzoyl oxybenzene sulphonate from sodium phenol sulphonate dihydrate and benzoyl chloride.

Preparation of esters

Phenol sulphonate esters can be made in a known process by reacting an alkali metal phenol sulphonate salt with an acyl halide in a hydrocarbon solvent at elevated temperatures, but the use of anhydrous materials were strongly advocated because any residual water hydrolyses the acyl chloride in a competitive reaction. However, it becomes particularly difficult and expensive to dehydrate phenol sulphonate salts below about 2% w/w water on a commercial scale and the product obtained by reaction from such partly dehydrated salts can be comparatively impure or reduced in yield. Consequently, changes to the process such as omitting the solvent or using a different acylating agent have been proposed, but these alternatives introduce their own respective manufacturing problems such as entrainment of viscous acyl chloride and anhydride in the product or introduction of a cumbersome and hence expensive recovery process involving an extra distillation step amongst others. The present invention provides a surprisingly convenient modification to the known process in which the esterification and product separation steps are incorporated into a cycle together with an acyl halide preparation step in which residual carboxylic acid and anhydride in solution after product separation is preferably augmented with a replenishing amount of carboxylic acid and then reacted with thiony halide. The resultant ester is readily separable and is obtained in comparatively good yield.

Ester manufacture

Sulphophenyl esters can be made amongst other routes by reacting an acyl halide with a phenol sulphonate salt, but it has been suggested in the prior art that there are substantial problems or disadvantages associated with carrying out the reaction in the presence of an organic solvent such as gelation of the reaction medium or excessive reaction times. In the present invention, the process employs as organic solvent high boiling point primarily aliphatic hydrocarbons which forms with linear acyl halide a reaction medium in which products of high and/or improved purity and/or yield are obtainable without gelation and in reasonable reaction periods, especially between C.sub.6 -C.sub.10 linear acyl chlorides and sodium phenol sulphonate. It has been found advantageous to pre-dry the phenol sulphonate salt by heating it when dispersed in a high boiling aliphatic or aromatic hydrocarbon solvent such that water and solvent are co-removed, with the result that in a subsequent esterification reaction with acyl halide an improvement in yield and/or purity of the sulphophenyl ester can be achieved.

Preparation of sulphophenyl esters

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Warrington, United Kingdom

John P Sankey