公开(公告)号：US11708317B2

公开(公告)日：2023-07-25

申请号：US17131021

申请日：2020-12-22

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Philippe Marion

IPC: C07C45/48 ,  C07C51/265 ,  C07C51/38 ,  C07C49/76

CPC classification number: C07C45/48 ,  C07C49/76 ,  C07C51/265 ,  C07C51/38

Abstract: 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.

公开(公告)号：US11692124B2

公开(公告)日：2023-07-04

申请号：US17013964

申请日：2020-09-08

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Remy Leroy ,  Mikel Morvan ,  Patrick Moreau ,  Philippe Marion

IPC: C09K8/584 ,  C07C309/07 ,  E21B43/16

CPC classification number: C09K8/584 ,  C07C309/07 ,  E21B43/16

Abstract: Compositions suitable for enhanced oil recovery comprising
a) a mixture of α-sulfocarbonyl compounds of formulae (1) and (2) in a mixture ratio (1) to (2) of from 1:99 to 99:1




wherein
R1, R3 and R5, 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,
R2 and R4, 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.

公开(公告)号：US11091417B2

公开(公告)日：2021-08-17

申请号：US16326460

申请日：2017-08-17

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Rémy Leroy ,  Philippe Marion

IPC: C07C45/48

Abstract: 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.

公开(公告)号：US20230312822A1

公开(公告)日：2023-10-05

申请号：US18331471

申请日：2023-06-08

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Valerio Bramati

IPC: C08G65/26 ,  A01N25/04 ,  A01N25/30 ,  A61K47/34

CPC classification number: C08G65/2609 ,  A01N25/04 ,  A01N25/30 ,  A61K47/34 ,  C08G65/2612 ,  A61K45/06

Abstract: A mixture of two alkoxylates surfactants, one being an aryl aliphatic carbinol alkoxylate, the other one being a dialiphatic carbinol alkoxylate, said mixture being useful for stabilizing emulsions and dispersions used in agricultural or pharmaceutical formulations. The alkoxylates surfactants may serve as substitutes for nonylphenol ethoxylates (NPE) and tristyrylphenol ethoxylates (TSE).

公开(公告)号：US11773053B2

公开(公告)日：2023-10-03

申请号：US16769845

申请日：2017-12-20

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Bing Hong ,  Matthieu Guirardel

IPC: C07C211/63 ,  C02F1/52 ,  C02F1/54 ,  C07C209/68

CPC classification number: C07C211/63 ,  C02F1/5272 ,  C02F1/547 ,  C07C209/68

Abstract: 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.

公开(公告)号：US11028315B2

公开(公告)日：2021-06-08

申请号：US16091227

申请日：2017-03-30

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Philippe Marion ,  Mikel Morvan

IPC: C09K8/584 ,  C07C229/12 ,  C07C309/14 ,  E21B43/16

Abstract: The instant invention relates to surfactants having the following formula (I) wherein: each of Ra and Rb is a linear or branched, saturated or unsaturated, hydrocarbon chain, each of Rc and Rd is a alkyl chain having 1 to 10 carbon atoms, each of (E1) and (E2) is a divalent hydrocarbon radical, A is: a group a carboxylate group —COO− (optionally in all or part in the form —COOH); or a sulfonate group —SO3− (optionally in all or part in the form —SO3H). The invention also relate to the preparation of these surfactants and their use in oil extraction, especially in EOR applications.

公开(公告)号：US11702386B2

公开(公告)日：2023-07-18

申请号：US16970987

申请日：2018-02-21

Applicant: RHODIA OPERATIONS ,  SOLVAY SA

Inventor： Olivier Back ,  Rémy Leroy ,  Philippe Marion

IPC: C07C303/06 ,  C07C29/149 ,  C07C31/02 ,  C07C309/20 ,  B01J19/00 ,  B01J23/745 ,  B01J35/02

CPC classification number: C07C303/06 ,  B01J19/0013 ,  B01J23/745 ,  B01J35/026 ,  C07C29/149 ,  B01J2219/00029 ,  C07C31/02 ,  C07C309/20

Abstract: Process P1 for the manufacture of a secondary fatty alcohol, said process P1 comprising synthesizing an internal ketone K1 by a process P0 comprising 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 K2 at liquid state, which is identical or similar to the internal ketone K1, is introduced into the reaction medium, and subjecting the internal ketone K1 to 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 P1 for the manufacture of an internal olefin or of an internal olefin sulfonate.

公开(公告)号：US20230026924A1

公开(公告)日：2023-01-26

申请号：US17781308

申请日：2020-11-27

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Sergio Mastroianni

IPC: C07C225/06 ,  C07D211/74

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

公开(公告)号：US11267781B2

公开(公告)日：2022-03-08

申请号：US16347977

申请日：2017-11-08

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Rémy Leroy ,  Philippe Marion

IPC: C07C45/48 ,  C07C215/18 ,  C07C221/00 ,  C07C225/06 ,  C07C41/03 ,  C07C67/03 ,  C07C29/145 ,  C08G65/08

Abstract: Method (M) for the preparation of an end compound from an internal ketone, said method comprising: —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° C. to 270° C., —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.

公开(公告)号：US10906857B2

公开(公告)日：2021-02-02

申请号：US16623100

申请日：2018-06-15

Applicant: RHODIA OPERATIONS

Inventor： Olivier Back ,  Philippe Marion

IPC: C07C45/48 ,  C07C51/00 ,  C07C49/76 ,  C07C51/265 ,  C07C51/38

Abstract: 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.