Fatty amino alcohols and process for preparing same
AssigneesPivert, Centre National de la Recherche Scientifique (CNRS), Universite D'Artois
InventorsFrederic HAPIOT, Eric MONFLIER, Theodore VANBESIEN
Life of this patent
Estimating the term…
Abstract
The present invention relates to amino alcohol compounds and to the preparation thereof from fatty esters comprising at least two carbon-carbon double bonds. In particular, the present invention relates to fatty amino alcohol compounds obtained by means of a process coupling, in a single step, a hydroaminomethylation reaction and a hydrohydroxymethylation reaction.
Claims14
A compound of formula (IIIa), (IIIb) or (IIIc):
- in which
- u is an integer between 1 and 7,
- R1, R7, R8, R9, R10, R5, and R6 independently of one another and, for R1, independently for each of the units (CHR1)u represent a moiety of formula (II), H, —OR15, C1-C10 alkyl unsubstituted or substituted by one or more groups —OR15, C6-C12 aryl unsubstituted or substituted by one or more groups —OR15, or C3-C10 cycloalkyl unsubstituted or substituted by one or more groups —OR15,
- R15 represents H or C1-C10 alkyl unsubstituted or substituted by one or more —OH groups, by one or more groups of formula (II), or by a group of formula (IV)
- in which
- R20, R21, R22, and R23 independently of one another represent H, —OH, C1-C10 alkyl unsubstituted or substituted by one or more groups —OR24;
- R24 represents H or C1-C10 alkyl unsubstituted or substituted by one or more —OH groups or by one or more groups of formula (II);
- or
- in which
- R1, R2, R5, and R6 independently of one another represent a group of formula (II), —OR15, C1-C10 alkyl unsubstituted or substituted by one or more groups —OR15,
- R15 represents H or C1-C10 alkyl unsubstituted or substituted by one or more —OH groups, by one or more groups of formula (II), or by a group of formula (IV);
- or
- in which
- R5 and R6 independently of one another represent a group of formula (II);
- the group of formula (II) being
- and comprising at least 4 carbon atoms and at most 80 carbon atoms, and in which n is an integer between 1 and 10;
- A is selected, independently for each of the units (A)n, from the groups of formula (IIa), (IIb), (IIc) or (IId)
- —[(CH2)q—CH═CH—(CH2)t]— (IIa),
- —[(CH2)v—CH(CH2NR3R4)—CH2—(CH2)w]— (IIb),
- —[(CH2)y—CH(CH2OH)—CH2—(CH2)z]— (IIc),
- —[(CH2)x]— (IId),
- where q, t, v, w, y and z are integers between 0 and 20, the sum of q+t, v+w or y+z being less than 20;
- x is an integer between 10 and 30;
- R3 and R4 independently of one another represent H, C1-C10 alkyl, C6-C12 aryl, benzyl, C3-C10 cycloalkyl, or R3 and R4 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycle;
- the compound of formula (IIIa), (IIIb) or (IIIc) comprising at least one group of formula (II) in which at least one of the units (A)n is of formula (IIb), and at least one group of formula (II) in which at least one of the units (A)n is of formula (IIc).
A process for preparing amino alcohol from a compound B comprising at least two carbon-carbon double bonds, said process comprising a step a) of combining with stirring at least one precatalyst, being a complex comprising a transition metal selected from columns 8 to 10 of the periodic table, an amine of formula HNR3R4 in which R3 and R4 independently of one another represent H, C1-C10 alkyl, C6-C12 aryl, C3-C10 cycloalkyl, or R3 and R4 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycle;
- and said compound B, in an atmosphere of hydrogen and carbon monoxide, to form a compound obtained from said compound B in which one carbon atom of at least one of the carbon-carbon double bonds of the compound B has been substituted by a moiety —CH2NR3R4, the other carbon atom of this same carbon-carbon double bond being substituted by a hydrogen;
- and in which one carbon atom of at least one other of the carbon-carbon double bonds of the compound B has been substituted by a —CH2OH moiety, the other carbon atom of this same carbon double bond being substituted by a hydrogen.
Dependencies are inferred from the claim text.