Fatty amino alcohols and process for preparing same

Patent metadata

Field	Value
Publication number	US-10315983-B2
Application number	US-201615541769-A
Country	US
Kind code	B2
Filing date	Feb 9, 2016
Priority date	Feb 12, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

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.

First claim

The invention claimed is:

1. A compound of formula (IIIa):

in which
u is an integer between 1 and 5;
R 7 , R 8 , R 9 and R 10 represent a hydrogen,
R 1 , R 5 , and R 6 independently of one another and, for R 1 , independently for each of the units (CHR 1 ) u 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;
in which A is selected, independently for each of the units (A) n , from the groups of formula (IIa), (IIb), or (IIc)
—[(CH 2 ) q —CH═CH—(CH 2 ) t ]—  (IIa),

—[(CH 2 ) v —CH(CH 2 NR 3 R 4 )—CH 2 —(CH 2 ) w ]—  (IIb),

—[(CH 2 ) y —CH(CH 2 OH)—CH 2 —(CH 2 ) z ]—  (IIc),

—[(CH 2 ) 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;
R 3 and R 4 independently of one another represent H, C 1 -C 10 alkyl, C 6 -C 12 aryl, benzyl, C 3 -C 10 cycloalkyl, or R 3 and R 4 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycle;
the compound of formula (IIIa) 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 of formula (IIc).

2. A compound of formula (IIIa):

in which
R 7 , R 8 , R 9 , and R 10 represent a hydrogen,
u is 1,
R 1 , R 5 , and R 6 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;
in which A is selected, independently for each of the units (A) n , from the groups of formula (IIb) or (IIc)
—[(CH 2 ) q —CH═CH—(CH 2 ) t ]—  (IIa),

—[(CH 2 ) v —CH(CH 2 NR 3 R 4 )—CH 2 —(CH 2 ) w ]—  (IIb),

—[(CH 2 ) y —CH(CH 2 OH)—CH 2 —(CH 2 ) z ]—  (IIc),

—[(CH 2 ) 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;
R 3 and R 4 independently of one another represent H, C 1 -C 10 alkyl, C 6 -C 12 aryl, benzyl, C 3 -C 10 cycloalkyl, or R 3 and R 4 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycle;
n is an integer between 1 and 5;
each of the substituents R 1 , R 5 , and R 6 comprising at least 12 carbon atoms and at most 25 carbon atoms,
the compound of formula (IIIa) 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).

3. The compound as claimed in claim 1 of formula (IIIa) in which
R 7 , R 8 , R 9 , and R 10 represent a hydrogen and u is 1,
R 1 , R 5 , and R 6 independently of one another represent a group of formula (II) in which n is 1,
A is a group of formula (IIb) or (IIc)
[(CH 2 ) v —CH(CH 2 NR 3 R 4 )—CH 2 —(CH 2 ) w ]—  (IIb), or

[(CH 2 ) y —CH(CH 2 OH)—CH 2 —(CH 2 ) z ]—  (IIc);

R 3 and R 4 independently of one another represent H, C 1 -C 10 alkyl, C 6 -C 12 aryl, benzyl, C 3 -C 10 cycloalkyl, or R 3 and R 4 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycle;
v, y, w, and z independently of one another are an integer between 4 and 9, where v+w or y+z is an integer between 11 and 15,
the compound of formula (IIIa) comprising at least one group of formula (II) in which A is of formula (IIb) and at least one group of formula (II) in which A is of formula (IIc).

4. The compound as claimed in claim 1 where R 3 and R 4 independently represent C 2 -C 8 alkyl.

5. The compound as claimed in claim 1 where n is 1 in the group of formula (II), and the compound (IIIa) comprises at least one group of formula (II) in which A is (IIb), and at least one group of formula (II) in which A is (IIc).

6. The compound as claimed in claim 2 of formula (IIIa) in which
R 7 , R 8 , R 9 , and R 10 represent a hydrogen and u is 1,
R 1 , R 5 , and R 6 independently of one another represent a group of formula (II) in which n is 1,
A is a group of formula (IIb) or (IIc)
[(CH 2 ) v —CH(CH 2 NR 3 R 4 )—CH 2 —(CH 2 ) w ]—  (IIb), or

[(CH 2 ) y —CH(CH 2 OH)—CH 2 —(CH 2 ) z ]—  (IIc);

R 3 and R 4 independently of one another represent H, C 1 -C 10 alkyl, C 6 -C 12 aryl, benzyl, C 3 -C 10 cycloalkyl, or R 3 and R 4 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycle;
v, y, w, and z independently of one another are an integer between 4 and 9, where v+w or y+z is an integer between 11 and 15,
the compound of formula (IIIa) comprising at least one group of formula (II) in which A is of formula (IIb) and at least one group of formula (II) in which A is of formula (IIc).

7. The compound as claimed in claim 2 where R 3 and R 4 independently represent C 2 -C 8 alkyl.

8. The compound as claimed in claim 2 where n is 1 in the group of formula (II), and the compound (IIIa) comprises at least one group of formula (II) in which A is (IIb), and at least one group of formula (II) in which A is (IIc).

Assignees

• Pivert S A S
• Centre Nat Rech Scient
• Univ Dartois

Inventors

• Hapiot Frederic
• Monflier Eric
• Vanbesien Theodore

Classifications

• C07C227/10

  with simultaneously increasing the number of carbon atoms in the carbon skeleton · CPC title

• C07C229/12 Primary

  to carbon atoms of acyclic carbon skeletons · CPC title