Process for preparing esteramide compounds
View Patent ↗The present invention concerns a process for preparing esteramide compounds. More particularly, the invention relates to a process for preparing esteramide compounds by reaction between a diester and an amine, in the presence of a basic compound, wherein the basic compound and the amine in gaseous form are co-added to the diester, the reaction being conducted at a temperature of 30° C. or higher.
1. A process for preparing an esteramide compound of following formula (I):
R 1 OOC-A-CONR 2 R 3 (I)
comprising a reaction step between:
a diester compound of following formula (II):
R 1 OOC-A-COOR 1 (II)
and an amine of following formula (III):
HNR 2 R 3 (III)
in the presence of a basic compound,
formulae in which:
A is a covalent bond or a straight-chain or branched divalent alkylene group comprising a number of carbon atoms ranging from 1 to 12,
R 1 is an optionally substituted hydrocarbon group, comprising from 1 to 36 carbon atoms,
R 2 and R 3 , the same or different, are groups chosen from the hydrogen atom and the hydrocarbon groups, optionally substituted, comprising from 1 to 36 carbon atoms,
R 2 and R 3 are able together to form a ring comprising the nitrogen atom with which they are linked, the said ring optionally being substituted and/or comprising an additional heteroatom, and
R 2 and R 3 not simultaneously being hydrogen atoms,
wherein:
the amine of formula (III) in gaseous form and the basic compound are co-added to the diester compound of formula (II),
and the reaction is conducted at a temperature of 30° C. or higher;
wherein the diester compound of formula (II) is a mixture of diester compounds of following formulae (II.1), (II.2) and (II.3):
R 1 OOC—CH(CH 3 )—CH 2 —CH 2 —COOR 1 (II.1)
R 1 OOC—CH(CH 2 —CH 3 )—CH 2 —COOR 1 (II.2)
R 1 OOC—CH 2 —CH 2 —CH 2 —CH 2 —COOR 1 (II.3).
2. The process according to claim 1 , wherein the R 1 groups, the same or different, are hydrocarbon groups comprising from 1 to 16 carbon atoms optionally carrying one or more substituents.
3. The process according to claim 1 , wherein the R 1 groups, the same or different, are chosen from the group consisting of the alkyl, alkenyl, cycloalkyl, aryl and arylalkyl groups, the said groups optionally carrying one or more substituents.
4. The process according to claim 1 , wherein R 1 is chosen from the group consisting of the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiobutyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, cyclopentyl, n-hexyl, isohexyl, sec-hexyl, cyclohexyl, methylcyclohexyl, 2-ethylbutyl, 3-methylpentyl, n-heptyl, isoheptyl, sec-heptyl, 3-methylhexyl, 4-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, isooctyl, 3-methylheptyl, n-nonyl, n-decyl, undecyl, n-dodecyl, tridecyl, tetradecyl and pentadecyl groups.
5. The process according to claim 1 , wherein the mixture of diester compounds of formula (II.1), (II.2) and (II.3) has the following composition:
from 75 to 95% by weight of the formula (II.1) compound, from 3 to 23% by weight of the formula (II.2) compound, and
from 0.1 to 10% by weight of the formula (II.3) compound.
6. The process according to claim 1 , wherein the R 1 groups are methyl groups.
7. The process according to claim 1 , wherein the groups R 2 and R 3 , the same or different, are chosen from the group consisting of the alkyl, alkenyl, cycloalkyl, aryl and arylalkyl groups, the said groups optionally carrying one or more substituents.
8. The process according to claim 7 , wherein R 2 and R 3 , the same or different, are chosen from the group consisting of the methyl, ethyl, hydroxyethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiobutyl, n-pentyl, isoamyl, hexyl and cyclohexyl groups.
9. The process according to claim 1 , wherein R 2 and R 3 together form a ring with 5 to 6 atoms, comprising the nitrogen atom with which they are linked, one of the atoms of the ring optionally being another heteroatom.
10. The process according to claim 9 , wherein R 2 and R 3 together form a ring chosen from morpholine, piperidine and piperazine.
11. The process according to claim 1 , wherein the basic compound is an alkoxide of an alkaline metal or alkaline-earth metal; potassium or sodium carbonate, alkyl titanates and mixtures thereof.
12. The process according to claim 1 , wherein the basic compound is in solution in an organic solvent.
13. The process according to claim 12 , wherein the organic solvent is chosen from alcohols and ethers, and mixtures thereof.
14. The process according to claim 1 , wherein the added quantity of amine (III) in gaseous form corresponds to a molar ratio relative to the diester compound (II) ranging from 1 to 1.5.
15. The process according to claim 1 , wherein the basic compound is added at a molar concentration relative to the diester compound comprised from 0.01 to 20%.
16. The process according to claim 1 , wherein the reaction is conducted at a temperature comprised from 30° C. to 130° C.
17. The process according to claim 1 , wherein the reaction is conducted at a temperature comprised from 40° C. to 90° C.
18. The process according to claim 1 , wherein the reaction is conducted at a temperature comprised from 45° C. to 65° C.
19. A process for preparing an esteramide compound of following formula (I):
R 1 OOC-A-CONR 2 R 3 (I)
comprising a reaction step between:
a diester compound of following formula (II):
R 1 OOC-A-COOR 1 (II)
and an amine of following formula (III):
HNR 2 R 3 (III)
in the presence of a basic compound,
formulae in which:
A is a covalent bond or a straight-chain or branched divalent alkylene group comprising a number of carbon atoms ranging from 1 to 12,
R 1 is an optionally substituted hydrocarbon group, comprising from 1 to 36 carbon atoms,
R 2 and R 3 , the same or different, are groups chosen from the hydrogen atom and the hydrocarbon groups, optionally substituted, comprising from 1 to 36 carbon atoms,
R 2 and R 3 are able together to form a ring comprising the nitrogen atom with which they are linked, the said ring optionally being substituted and/or comprising an additional heteroatom, and
R 2 and R 3 not simultaneously being hydrogen atoms,
wherein:
the amine of formula (III) in gaseous form and the basic compound are co-added to the diester compound of formula (II),
and the reaction is conducted at a temperature of 30° C. or higher; and
wherein the added quantity of amine (III) in gaseous form corresponds to a molar ratio relative to the diester compound (II) ranging from 1 to 1.5.
20. The process according to claim 19 , wherein the diester compound of formula (II) is a mixture of diester compounds of following formulae (II.1), (II.2) and (II.3):
R 1 OOC—CH(CH 3 )—CH 2 —CH 2 —COOR 1 (II.1)
R 1 OOC—CH(CH 2 —CH 3 )—CH 2 —COOR 1 (II.2)
R 1 OOC—CH 2 —CH 2 —CH 2 —CH 2 —COOR 1 (II.3).
21. The process according to claim 19 , wherein the mixture of diester compounds of formula (II.1), (II.2) and (II.3) has the following composition:
from 75 to 95% by weight of the formula (II.1) compound,
from 3 to 23% by weight of the formula (II.2) compound,
from 0.1 to 10% by weight of the formula (II.3) compound.
22. A process for preparing an esteramide compound of following formula (I):
R 1 OOC-A-CONR 2 R 3 (I)
comprising a reaction step between:
a diester compound of following formula (II):
R 1 OOC-A-COOR 1 (II)
and an amine of following formula (III):
HNR 2 R 3 (III)
in the presence of a basic compound,
formulae in which:
A is a covalent bond or a straight-chain or branched divalent alkylene group comprising a number of carbon atoms ranging from 1 to 12,
R 1 is an optionally substituted hydrocarbon group, comprising from 1 to 36 carbon atoms,
R 2 and R 3 , the same or different, are groups chosen from the hydrogen atom and the hydrocarbon groups, optionally substituted, comprising from 1 to 36 carbon atoms,
R 2 and R 3 are able together to form a ring comprising the nitrogen atom with which they are linked, the said ring optionally being substituted and/or comprising an additional heteroatom, and
R 2 and R 3 not simultaneously being hydrogen atoms,
wherein:
the amine of formula (III) in gaseous form and the basic compound are co-added to the diester compound of formula (II),
and the reaction is conducted at a temperature of 30° C. or higher; and
wherein the basic compound is added at a molar concentration relative to the diester compound comprised from 0.01 to 20%.
23. The process according to claim 22 , wherein the diester compound of formula (II) is a mixture of diester compounds of following formulae (II.1), (II.2) and (II.3):
R 1 OOC—CH(CH 3 )—CH 2 —CH 2 —COOR 1 (II.1)
R 1 OOC—CH(CH 2 —CH 3 )—CH 2 —COOR 1 (II.2)
R 1 OOC—CH 2 —CH 2 —CH 2 —CH 2 —COOR 1 (II.3).
24. The process according to claim 22 , wherein the mixture of diester compounds of formula (II.1), (II.2) and (II.3) has the following composition:
from 75 to 95% by weight of the formula (II.1) compound,
from 3 to 23% by weight of the formula (II.2) compound,
from 0.1 to 10% by weight of the formula (II.3) compound.
25. A process for preparing an esteramide compound of following formula (I):
R 1 OOC-A-CONR 2 R 3 (I)
comprising a reaction step between:
a diester compound of following formula (II):
R 1 OOC-A-COOR 1 (II)
and an amine of following formula (III):
HNR 2 R 3 (III)
in the presence of a basic compound,
formulae in which:
A is a covalent bond or a straight-chain or branched divalent alkylene group comprising a number of carbon atoms ranging from 1 to 12,
R 1 is an optionally substituted hydrocarbon group, comprising from 1 to 36 carbon atoms,
R 2 and R 3 , the same or different, are groups chosen from the hydrogen atom and the hydrocarbon groups, optionally substituted, comprising from 1 to 36 carbon atoms,
R 2 and R 3 are able together to form a ring comprising the nitrogen atom with which they are linked, the said ring optionally being substituted and/or comprising an additional heteroatom, and
R 2 and R 3 not simultaneously being hydrogen atoms,
wherein:
the amine of formula (III) in gaseous form and the basic compound are co-added to the diester compound of formula (II),
and
wherein the reaction is conducted at a temperature comprised from 45° C. to 65° C.
26. The process according to claim 25 , wherein the diester compound of formula (II) is a mixture of diester compounds of following formulae (II.1), (II.2) and (II.3):
R 1 OOC—CH(CH 3 )—CH 2 —CH 2 —COOR 1 (II.1)
R 1 OOC—CH(CH 2 —CH 3 )—CH 2 —COOR 1 (II.2)
R 1 OOC—CH 2 —CH 2 —CH 2 —CH 2 —COOR 1 (II.3).
27. The process according to claim 25 , wherein the mixture of diester compounds of formula (II.1), (II.2) and (II.3) has the following composition:
from 75 to 95% by weight of the formula (II.1) compound,
from 3 to 23% by weight of the formula (II.2) compound,
from 0.1 to 10% by weight of the formula (II.3) compound.