Rhodia Operations

Centre National De La Recherche Scientifique

Solvay Sa

Specialty Operations France

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Philippe Marion

Rémy Leroy

Mikel Morvan

Pascal Herve

Jian Zhou

Patrick Moreau

Rose Ndong

Remy Leroy

Sergio Mastroianni

Laurent Garel

Hong Liu

Didier Morvan

Valerio Bramati

Bing Hong

Eric Muller

Mathieu Pucheault

Flavie Sarrazin

Roberto Company

Kevin Olivon

Raphaël Wischert

Matthieu Guirardel

Christelle Florence Chretien

Raphael Wischert

The invention concerns new keto-ammonium compounds with surfactant properties and improved biodegradability.

Keto-ammonium compounds

The present invention concerns new cationic quaternary ammonium compounds which exhibit excellent adsorption properties on negatively charged surfaces. These ones can notably be obtained firstly by reacting an internal ketone with a twin-tail amine under reductive amination conditions to obtain a twin tail triamine, then subjecting the twin tail triamine to a quaternization reaction. They can also obtained be obtained by the quaternization reaction of a certain diamine.

Cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture

Methods of acidizing a subterranean formation penetrated by a wellbore that include the steps of (a) injecting into the wellbore at a pressure below subterranean formation fracturing pressure a treatment fluid having a first viscosity and including an aqueous acid and a gelling agent selected from the group consisting of Formulas I-XI and combinations thereof; (b) forming at least one void in the subterranean formation with the treatment fluid; and (c) allowing the treatment fluid to attain a second viscosity that is greater than the first viscosity.

Method of acidizing a subterranean formation comprising a gelling agent

The present invention pertains to a process for the cross-ketonization (Piria reaction) between an aryl carboxylic acid and an aliphatic carboxylic acid using a metal-based compound and a slight or a moderate excess of aryl carboxylic acid. A good selectivity, up to 99 mol %, can be achieved. The aryl aliphatic ketone can be used for the preparation of surfactants and other downstream products.

Process for the catalytic decarboxylative cross-ketonization of aryl and aliphatic carboxylic acid

Process Pfor the manufacture of a secondary fatty alcohol, said process Pcomprising synthesizing an internal ketone K1 by a process Pcomprising the decarboxylative ketonization reaction of a fatty acid or the like in a liquid phase with a metal compound as catalyst in a reaction medium, wherein a ketone Kat liquid state, which is identical or similar to the internal ketone K, is introduced into the reaction medium, and subjecting the internal ketone Kto a hydrogenation reaction with hydrogen gas as hydrogenating agent to form the secondary fatty alcohol. Use of the secondary fatty alcohol manufactured by the process Pfor the manufacture of an internal olefin or of an internal olefin sulfonate.

Processes for the manufacture of secondary fatty alcohols, internal olefins and internal olefin sulfonates

Compositions suitable for enhanced oil recovery comprising a) a mixture of &#x3b1;-sulfocarbonyl compounds of formulae (1) and (2) in a mixture ratio (1) to (2) of from 1:99 to 99:1 wherein R, Rand R, which may be the same or different at each occurrence, are hydrogen or a linear or branched alkyl chain having 1 to 20 carbon atoms, Rand R, which may be the same or different at each occurrence, may be a linear or branched alkyl group having 4 to 24 carbon atoms and in which the alkyl chain may comprise one or more cycloaliphatic groups, and X is H or a metal forming a salt with the sulfonate group, and b) a salt containing aqueous solution.

Formulations for enhanced oil recovery comprising sulfonates

The invention relates to a process for preparing an &#x3b1;-methylene ketone comprising the step of reacting a ketone with formaldehyde in the presence of a catalyst which is an organic compound comprising at least one acid function or the corresponding salt, ester or amide thereof and at least one amine function or the corresponding ammonium salt, or a zwitterion thereof.

Process for the direct alpha-methylenation of ketones

Method (M) for the preparation of an end compound from an internal ketone, said method comprising: &#x2014;synthesizing the internal ketone by a process (P) for the decarboxylative ketonization of a fatty acid, a fatty acid derivative or a mixture thereof in a liquid phase with a metal compound as catalyst in the substantial absence of added solvent, wherein the fatty acid, fatty acid derivative or mixture thereof is added in sequential steps, the first step taking place at a temperature sequentially at a temperature from 100&#xb0; C. to 270&#xb0; C., &#x2014;causing the internal ketone to react in accordance with a single or multiple chemical reaction scheme involving at least one reagent other than the internal ketone, wherein at least one product of the chemical reaction scheme is the end compound that is not further caused to be chemically converted into another compound.

Method for making end compounds from internal ketones issued from the decarboxylative ketonization of fatty acids or fatty acid derivatives

A compound of general formula (I) or (II), wherein Rand Rindependently represent a C-Caliphatic group, Rto R, which may be the same or different at each occurrence, represent hydrogen or a C-Calkyl group, Xand X, which may be the same or different at each occurrence, represent a linear or branched divalent hydrocarbon radical with 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups, and Rand R, which may be the same or different at each occurrence, represent a group selected from &#x2014;O, -Alk-CH(OH)&#x2014;CH&#x2014;SO&#x2014; and -Alk-CO&#x2014; wherein Alk represents an alkylene group. 

Twin tail amine compounds and their zwitterionic derivatives

Process (P) for the decarboxylative ketonization of fatty acids, fatty acid derivatives or mixtures thereof in the liquid phase with metal compounds as catalyst wherein the fatty acids, fatty acid derivatives or mixtures thereof are added sequentially. Downstream chemistry can be realized starting from internal ketones obtained by process (P), especially in order to design and develop new surfactants.

Process for the decarboxylative ketonization of fatty acids or fatty acid derivatives

The present invention is directed to a process for synthesizing an internal ketone K1 by decarboxylative ketonization reaction of a fatty acid, a fatty acid derivative or a mixture thereof in a liquid phase with a metal compound as catalyst in a reaction medium, said process being characterized in that a ketone K2 at liquid state, which is identical or similar to the ketone K1, is introduced into the reaction medium. The so-synthesized internal ketone K1 can be used for the preparation of a variety of end compounds, including surfactants having a twin-tail structure or a Gemini structure.

The instant invention relates to surfactants having the following formula (I) wherein: each of Rand Ris a linear or branched, saturated or unsaturated, hydrocarbon chain, each of Rand Ris a alkyl chain having 1 to 10 carbon atoms, each of (E) and (E) is a divalent hydrocarbon radical, A is: a group a carboxylate group &#x2014;COO(optionally in all or part in the form &#x2014;COOH); or a sulfonate group &#x2014;SO(optionally in all or part in the form &#x2014;SOH). The invention also relate to the preparation of these surfactants and their use in oil extraction, especially in EOR applications. 

Zwitterionic surfactants suitable for enhanced oil recovery

The present invention relates to the production of xylene derivatives from furfural and its derivatives. The invention describes new routes for converting furfural and its derivatives into xylene derivatives including novel intermediates.

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Lyons, France

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