Transketalized compositions, synthesis, and applications
Ketal compounds of the structure I and a method of preparation of the compound from polyols and oxocarboxylates, as well as uses thereof.
1. A compound comprising structure I
wherein
R 1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety, wherein R 1 is the same or different for each occurrence;
R 2 is a covalent bond or a linear or branched alkyl group wherein R 2 is the same or different for each occurrence;
R 3 is the same or different for each occurrence and is a linear, branched, or cyclic alkyl group, or at least one R 3 is
wherein
n is 0, 1, or 2,
R′ is a linear or branched alkyl having between 1 and 6 carbon atoms, and
X is O or NR, wherein R is hydrogen or a linear or branched alkyl group having six or less carbon atoms;
R 4 is a covalent bond, methylene, or alkylmethylene, wherein a covalent bond indicates a 5-membered ring and a methylene or alkylmethylene indicates a 6-membered ring, wherein R 4 is the same or different for each occurrence;
R 5 is a covalent bond, methylene, ethylene, hydroxymethylene, —CH 2 —O—CH 2 —, or a polymeric moiety, wherein R 5 is the same or different for each occurrence;
R 6 and R 7 are independently linear, branched, or cyclic alkyl groups;
R 8 and R 9 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety;
Z is O or NR, wherein R is hydrogen or a linear or branched alkyl group having six or less carbon atoms wherein Z is the same or different for each occurrence;
γ is an integer of at least 1; and
the structure I comprises at least one α unit and at least one β unit.
2. The compound of claim 1 wherein γ is 1, α is 1, and β is 1, R 2 is —CH 2 CH 2 —, R 3 is CH 3 —, R 8 and R 9 are hydrogen, Z is O, and all R 4 and R 5 are covalent bonds.
3. The compound of claim 1 wherein R 1 is a cation or a linear or branched alkyl group having between 1 and 8 carbon atoms.
4. The compound of claim 1 wherein γ is 2, the sum of all α is 1, the sum of all β is 2, all R 2 are —CH 2 —, all R 3 are CH 3 —, R 8 and R 9 are hydrogen, all Z are O, and all R 4 and R 5 are covalent bonds.
5. The compound of claim 4 wherein R 6 and R 7 are independently methyl, ethyl, and isobutyl.
6. The compound of claim 4 wherein R 1 is sodium cation, ethyl, or n-butyl.
7. The compound of claim 1 wherein γ is 2, the sum of all α is 2, the sum of all β is 1, all R 2 are —CH 2 CH 2 —, all R 3 are CH 3 —, R 8 and R 9 are hydrogen, all Z are O, and all R 4 and R 5 are covalent bonds.