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

A method M for the preparation of at least one end compound from at least one internal ketone, said method M comprising:

• synthesizing the internal ketone by a process P for the decarboxylative ketonization of at least one fatty acid, at least one fatty acid derivative or a mixture thereof in a liquid phase with a metal compound as catalyst, wherein
• a) in a first step, elementary metal or a metal compound and the fatty acid, fatty acid derivative or mixture thereof comprising at least 10 mol %, based on the entire amount of fatty acid or fatty acid derivative, of fatty acid having 12 carbon atoms or less or derivative of fatty acid having 12 carbon atoms or less, are mixed in a molar ratio of from 1:0.8 to 1:3.5 (molar ratio metal:carboxyl group equivalent) and reacted for a period P1 of from 5 min to 24 h at a temperature T1 of from 100° C. to 270° C. in the substantial absence of added solvent, and
• b) thereafter the temperature is raised to a temperature T2 which is strictly above 270° C. and up to 400° C., and additional fatty acid, fatty acid derivative or a mixture thereof comprising at least 10 mol %, based on the entire amount of fatty acid or fatty acid derivative, of fatty acid having 12 carbon atoms or less or derivative of such fatty acid, is added over a period of time P2 of from 5 min to 24 h in the substantial absence of added solvent until the molar ratio of fatty acid, fatty acid derivative or mixture thereof to metal is in the range of from 6:1 to 99:1,
• and
• 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,
• with the proviso that
• when the internal ketone is caused to react by being subjected to a hydrogenation reaction to obtain a secondary alcohol, the so-obtained secondary alcohol is an intermediate that is in turn caused to react in accordance with a single or multiple reaction scheme that does not include a dehydration reaction that would convert said internal secondary alcohol into an internal olefin as an other intermediate or as the end compound, and
• the end compound differs from an α-sulfocarbonyl compound C1* of formula (1)
• from an α-sulfocarbonyl compound C2* of formula (2)
• and from a mixture thereof,
• wherein in above formulae (1) and (2)
• 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, are 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 cation forming a salt with the sulfonate group, and
• the end compound further differs from a surfactant C3* of formula (3)
• from a diamine C4* of formula (4)
• and from a mixture thereof,
• wherein in above formulae (3) and (4)
• each of Ra and Rb, which are identical or different, is a linear or branched, saturated or unsaturated, hydrocarbon chain that may be interrupted and/or substituted by at least a monocyclic or polycyclic group
• each of Rc and Rd, which are identical or different, is a linear or branched, alkyl chain having 1 to 10 carbon atoms
• each of (E1) and (E2) is a divalent hydrocarbon radical linear or branched, not substituted or substituted,
• A is:
• a carboxylate group —COO−, optionally in all or part in its protonated form —COOH;
• or a sulfonate group —SO3−, optionally in all or part in its protonated form —SO3H.