Glycitan esters of unsaturated fatty acids and their preparation
A method is disclosed for making an unsaturated glycitan ester by reacting intramolecular condensates of glycitols having four or more carbons with a metathesis-derived unsaturated fatty acid in the presence of an alkaline catalyst and under conditions sufficient to form the aforesaid unsaturated glycitan fatty ester. A composition is also disclosed comprising a compound of the following structure: wherein R 1 is hydrogen, alkyl, aryl or (CH 2 ) 1-9 —COOR 5 ; wherein R 5 is wherein R 2 , R 3 and R 4 are hydrogen, or —(O)C—(CH 2 ) m —CH═CH—R 1 or —(CH 2 CH 2 O) n H or mixtures thereof; wherein m is 1 to 9; and wherein n is 1 to 100.
1. A composition comprising the following structure:
wherein R 1 is a hydrogen atom, ethyl, propyl, pentyl, aryl or (CH 2 ) 1-9 —COOR 5 ; wherein R 5 is
wherein R 2 , R 3 and R 4 are independently at each occurrence a hydrogen atom, or —(O)C—(CH 2 ) m -CH═CH—R 1 or —(CH 2 CH 2 O) n H or mixtures thereof; wherein m is an integer from 1 to 9; and wherein n is an integer from 1 to 100.
2. The composition of claim 1 , wherein R 1 is a hydrogen atom.
3. The composition of claim 2 , wherein the composition comprises sorbitan 9-decenoate.
4. The composition of claim 1 , wherein R 1 is ethyl.
5. The composition of claim 4 , wherein the composition comprises sorbitan 9-dodecenoate.
6. The composition of claim 1 , wherein R 1 is propyl.
7. The composition of claim 6 , wherein the composition comprises sorbitan 9-tridecenoate.
8. The composition of claim 1 , wherein R 1 is pentyl.
9. The composition of claim 8 , wherein the composition comprises sorbitan 9-pentadecenoate.
10. The composition of claim 1 , wherein R 1 is —(CH 2 ) 1-9 —COOR 5 .
11. The composition of claim 10 , wherein R 1 is —(CH 2 ) 7 —COOR 5 .
12. The composition of claim 11 , wherein the composition comprises disorbitan 9-octadecene-1,18-dioate.