Polyethers, polyamines, polythioethers, and methods for making same
The invention relates to polyethers, polyamines, and polythioethers, as well as to processes for synthesizing them, e.g., using olefins as starting material.
1. A compound according to Formula I:
or a salt thereof, wherein,
R1 is a bond, optionally substituted C2-C12 alkyl, optionally substituted C2-C12 alkenyl, or optionally substituted C2-C12 alkynyl;
X is O, NH, or S;
one of the is a double bond and the other is a single bond; and
n is an integer between 2 and 100, provided that the compound of Formula I is not a compound wherein R1 is a bond, X is O and n is 2.
2. The compound of claim 1 , wherein X is O.
3. The compound of claim 1 , wherein X is NH.
4. The compound of claim 1 , wherein X is S.
5. The compound of claim 1 , wherein R1 is optionally substituted branched C3-C12 alkyl.
6. The compound of claim 1 , wherein R1 is unsubstituted branched C3-C12 alkyl.
7. The compound of claim 1 , wherein R1 is optionally substituted linear C2-C12 alkenyl or branched C3-C12 alkenyl.
8. The compound of claim 1 , wherein R1 is unsubstituted linear C2-C12 alkenyl or branched C3-C12 alkenyl.
9. The compound of claim 1 , wherein n is 2, 3, 4, 5, 6, 7, 8, 9, or 10.
10. The compound of claim 1 , wherein n is 2 or 3.
11. A method of producing a compound of claim 1 , or a salt thereof, comprising reacting a compound of Formula II or Formula III:
with methanesulfonic acid to obtain a compound of Formula I or a salt thereof:
wherein,
R1 is a bond, optionally substituted C2-C12 alkyl, optionally substituted C2-C12 alkenyl, or optionally substituted C2-C12 alkynyl;
X is O, NH, or S;
one of the is a double bond and the other is a single bond; and
n is an integer between 2and 100.
12. The method of claim 11 , wherein the reaction of a compound of Formula II or Formula III with methane sulfonic acid comprises an incubation step, quenching step, a phase separation step, and a distillation step.
13. The method of claim 12 , wherein the incubation step occurs at room temperature.
14. The method of claim 12 , wherein the incubation step occurs over four days.
15. The method of claim 11 , wherein the distillation step occurs at 85° C.
16. The method of claim 11 , wherein the distillation step occurs at 1.5 mbar.
17. The method of claim 11 , further comprising an amidation step, wherein a compound of Formula I, wherein X is O, reacts with NH3 under an elevated pressure to obtain a corresponding compound of Formula I, wherein X is NH.
18. The method of claim 11 , wherein the compound of Formula II is selected from the group consisting of:
19. The method of claim 11 , wherein the compound of Formula II is citronellol.
20. The compound according to claim 1 , wherein the compound of Formula I is:
wherein n is an integer between 2 and 100, or a salt thereof.
21. The compound according to claim 20 , wherein n is 2, 3, 4, 5, 6, 7, 8, 9, or 10.
22. A cosmetic or personal care composition comprising the compound according to claim 1 .
23. A cosmetic or personal care composition comprising the compound according to claim 20 .