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US 11,708,317 B2Granted
Process for the catalytic decarboxylative cross-ketonization of aryl and aliphatic carboxylic acid
AssigneeRhodia Operations
InventorsOlivier Back, Philippe Marion
Life of this patent
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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.
Claims20
A process for the preparation of at least one end compound from at least one aryl aliphatic ketone K,
- said aryl aliphatic ketone K being an aryl aliphatic ketone of formula (I)
- wherein Ar represents an aryl radical and Rn represents a C3-C27 aliphatic group,
- said process comprising
- synthesizing the aryl aliphatic ketone K through a process for the catalytic decarboxylative cross-ketonisation of aryl- and aliphatic carboxylic acids comprising the steps of:
- a) Providing a mixture containing:
- i) an aryl carboxylic acid,
- ii) an aliphatic carboxylic acid,
- iii) a metal-containing compound;
- in which the number of moles of the metal in the mixture is at least equal to 90% of the sum of the number of moles of aryl carboxylic acid and the number of moles of aliphatic carboxylic acid divided by the valency of the metal,
- said mixture being substantially free of any added solvent;
- b) heating the mixture at a temperature sufficient to form metal carboxylates;
- c) further heating the mixture at a temperature sufficient to form a dialiphatic ketone and an aryl aliphatic ketone K;
- d) adding to the reaction mixture of step c):
- i) aryl carboxylic acid in an amount which corresponds substantially to the amount of aryl carboxylic acid consumed during the formation of the aryl aliphatic ketone K in step c);
- ii) aliphatic carboxylic acid in an amount which corresponds substantially to the amount of aliphatic carboxylic acid consumed during the formation of the aryl aliphatic ketone K and the dialiphatic ketone in step c);
- maintaining the mixture at a temperature sufficient to continue forming the dialiphatic ketone and the aryl aliphatic ketone K;
- e) optionally repeating step d),
- causing the aryl aliphatic ketone K to react in accordance with a single or multiple chemical reaction scheme involving at least one reagent other than the aryl aliphatic ketone K, wherein at least one product of the chemical reaction scheme is the end compound product that is not further caused to be chemically converted into another compound.
15 more elements
A compound of formula (XXIII)
- wherein Ar represents an aryl radical and R′n represents a C2-C26 aliphatic group.
A compound of formula (XXXa) or (XXXb), or a mixture thereof,
- wherein
- Ar represents an aryl radical,
- Rn represents a C11-C27 aliphatic group,
- m and n are integers ranging from 0 to 50, provided at least one of m and n is of at least 1.
1 more element
Dependencies are inferred from the claim text.