METHOD FOR PREPARING 3-HYDROXYPROPIONATE ESTERS
A method includes contacting an epoxide and carbon monoxide to form a beta-propiolactone compound; contacting the beta-propiolactone compound and an initiator to form poly-3-hydroxy-propionate; and contacting the poly-3-hydroxy-propionate, an alcohol, and an esterification catalyst at a temperature sufficient to form an ester compound terminated by a hydroxyl group. The ester compound may be free of carbonylation and/or esterification catalysts.
1 . A method comprising:
contacting an epoxide and carbon monoxide to form a beta-propiolactone compound;
contacting the beta-propiolactone compound and an initiator to form poly-3-hydroxy-propionate; and
contacting the poly-3-hydroxy-propionate, an alcohol, and an esterification catalyst at a temperature sufficient to form an ester compound terminated by a hydroxyl group.
2 . The method of claim 1 , wherein the epoxide and the carbon monoxide are contacted in a first chamber.
3 . The method of claim 1 , wherein the beta-propiolactone compound and the initiator are contacted in a second chamber that is separated from the first chamber.
4 . The method claim 1 , wherein the poly-3-hydroxy-propionate, the alcohol, and the esterification catalyst are contacted in the second chamber or a third chamber that are each separated from the first chamber.
5 . The method of claim 1 , wherein the epoxide and the carbon monoxide are contacted in the presence of a carbonylation catalyst.
6 . The method of claim 1 , further comprising:
separating the beta-propiolactone compound from the carbonylation catalyst so that the beta-propiolactone compound is free of residues of the carbonylation catalyst.
7 . The method of claim 1 , wherein the epoxide has the following formula:
wherein each R 1 independently comprises one or more of hydrogen, straight or branched alkyl groups, aryl groups, alkyl-aryl groups, aryl-alkyl groups, or any combination thereof.
8 . The method of claim 1 , wherein the beta-propiolactone compound has the following formula:
wherein each R 1 independently comprises one or more of hydrogen, straight or branched alkyl groups, aryl groups, alkyl-aryl groups, aryl-alkyl groups, or any combination thereof.
9 . The method of claim 1 , further comprising:
separating the ester compound from the alcohol and/or the esterification catalyst.
10 . The method of claim 9 , wherein the separation of the ester compound may be performed by distillation, filtration, or oxidation.
11 . The method of claim 1 , wherein the ester compound comprises a hydroxyl group connected to an alkyl chain of at least three carbons.
12 . The method of claim 1 , wherein the ester compound comprises the following formula:
wherein each R 1 independently comprises one or more of hydrogen, straight or branched alkyl groups, aryl groups, alkyl-aryl groups, aryl-alkyl groups, or any combination thereof, and wherein R 2 comprises a straight or branched alkyl group, aryl group, alkyl-aryl group, or aryl-alkyl group.
13 . The method of claim 1 , wherein the ester compound is free of residues of the carbonylation catalyst.
14 . The method of claim 1 , wherein the esterification catalyst is configured to facilitate formation of the ester compound.
15 . The method of claim 1 , wherein the esterification catalyst comprises an acid catalyst.
16 . The method of claim 1 , wherein the alcohol comprises one or more straight or branched alkyl, aryl, alkyl-aryl, or aryl-alkyl groups.
17 . The method of claim 1 , wherein the contacting of the poly-3-hydroxy-propionate by the alcohol and the esterification catalyst is free of polymerization inhibitors.
18 . The method of claim 1 , wherein the ester compound is contacted with an amide to form an acrylonitrile compound.
19 . A composition comprising:
an ester compound that is a residue of a poly-3-hydroxy-propionate, a residue of a poly-3-hydroxy-propionate initiator, and a residue of an esterification catalyst.
20 . The composition of claim 19 , wherein the ester compound comprises any one of the following formulas:
wherein each R 1 independently comprises one or more of hydrogen, straight or branched alkyl groups, aryl groups, alkyl-aryl groups, aryl-alkyl groups, or any combination thereof, and wherein R 2 comprises a straight or branched alkyl group, aryl group, alkyl-aryl group, or aryl-alkyl group.