Polyether derivatives, uses, and methods of making the same

1. A compound according to Formula I:

or a salt thereof, wherein,

R 1 is optionally substituted C 1 -C 12 alkyl;

R 2 is C 1-2 alkyl, or C(O)—C 1-6 alkyl; and

n is an integer between 0 and 20.

2. The compound according to claim 1 , wherein R 1 is unsubstituted linear C 1 -C 12 alkyl or unsubstituted branched C 3 -C 12 alkyl.

3. The compound according to claim 1 , wherein R 1 is unsubstituted branched or unsubstituted linear C 6 alkyl.

4. The compound according to claim 3 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 .

5. The compound according to claim 1 , wherein R 2 is C 1-20 alkyl.

6. The compound according to claim 1 , wherein R 2 is C(O)—C 1-6 alkyl.

7. The compound according to claim 6 , wherein R 2 is selected from the group consisting of C(O)—C 1-5 alkyl, C(O)—C 1-4 alkyl, C(O)—C 1-3 alkyl and C(O)—C 1-2 alkyl.

8. The compound according to claim 1 , wherein n is 0, 1, 2, or 3.

9. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, or n-hexyl.

10. A composition comprising the compound according to claim 1 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

11. The composition according to claim 10 which is a fragrance composition, or a perfume composition, or a soap composition, or an insect repellant composition, or an insecticide composition, or a detergent composition, or a household cleaning agent composition, or an air freshener composition, or a room spray composition, or a pomander composition, or a candle composition, or a cosmetic composition, or a toilet water composition, or a pre-shave or after-shave lotion composition, or a talcum-powder composition, or a hair-care product composition, or a body deodorant composition, or an antiperspirant composition, or a shampoo composition, or a pet litter composition, or a topically applied skin care composition, or a paint or coating composition, or a lubricant composition, or a plastic composition, or a defoamer composition, or a hydraulic fluid composition, or an antimicrobial composition.

12. The composition according to claim 10 , which is a fragrance composition, insect repellent composition, candle composition, or cosmetic composition.

13. A method of making a compound according to claim 1 , or a salt thereof, wherein the method comprises the steps of

(1) introducing into a reactor a compound of Formula A:

wherein, R 1 is optionally substituted C 1 -C 12 alkyl; and

(2) exposing said compound to a solid ion-exchange resin, thereby causing the polymerization of the compound of Formula A to yield the compound of Formula I, wherein R 2 is H; and

(3) isolating and/or purifying said compound, wherein n is from 0-5; and

(4) reacting the compound of Formula I, wherein R 2 is H, with a suitable reagent to convert R 2 to C(O)—C 1-6 alkyl.

14. The method according to claim 13 , wherein the C(O)—C 1-6 alkyl is methyl or ethyl.

15. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is methyl.

16. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is ethyl.

17. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is propyl.

18. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 0, 1 or 2, and R 2 is C(O)—C 1-6 alkyl.

19. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 0, 1 or 2, and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is methyl, ethyl or propyl.

20. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 0, 1 or 2, and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is methyl.

21. A compound of the formula:

wherein R 2 is H, C 1-20 alkyl, aryl, aryl C 1-2 alkyl, optionally unsaturated alkyl esters, or optionally substituted aryl esters; and n is an integer between 0 and 20.

22. The compound according to claim 21 , wherein n is 0, 1, 2, or 3.

23. A composition comprising the compound according to claim 21 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

24. A compound according to Formula II:

or a salt thereof, wherein,

R 1 is optionally substituted C 1 -C 12 alkyl;

n1 and n2 are each independently an integer between 0 and 20; and

X is a diacyl moiety of the formula —C(O)—R 3 —C(O)—, wherein R 3 is optionally substituted C 1-22 alkyl, optionally substituted C 2-22 alkenyl or optionally substituted aryl.

25. The compound according to claim 24 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 .

26. The compound according to claim 25 , wherein R 3 is unsubstituted C 1-10 alkyl or wherein R 3 is unsubstituted C 1-6 alkyl.

27. The compound according to claim 25 , wherein n1 and/or n2 are each independently 0, 1, 2 or 3.

28. A composition comprising the compound according to claim 24 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

29. A method of making an ester Compound 1A, according to Formula I:

wherein, R 1 is optionally substituted C 1 -C 12 alkyl; and wherein R 2 is (C═O)C 1-4 alkyl, and n is an integer between 0 and 20;

wherein the method comprises reacting the alcohol Compound 1 of Formula I, wherein R 2 is H, with an alkyl anhydride of the formula R 2 O(C═O)OR 2 , wherein R 2 is (C═O)C 1-4 alkyl, and wherein the reaction is conducted under continuous flow conditions in the absence of a base or catalyst.