Method of making cyclobutane-1, 2-diacids degradable building blocks for materials
A method of making cyclobutane-1,2-diacid building blocks includes using trans-cinnamic acid in its beta form (head to head packing) and photodimerizing the trans-cinnamic acid to create cis-cyclobutane-1,2-dicarboxylic acid (CBDA-4).
1. A method of making a cis-cyclobutane-1,2-dicarboxylic acid monomer comprises:
a. melting trans-cinnamic acid;
b. dissolving trans-cinnamic acid from step a in an organic solvent to form a trans-cinnamic acid solution;
c. mixing the trans-cinnamic acid solution from step b into a poor solvent to create a slurry; and
d. irradiating the slurry from step c with a UV irritation source to photo-dimerize β-trans-cinnamic acid and form cis-cyclobutane-1,2-dicarboxylic acid.
2. The method of claim 1 , wherein melting is done between 134 and 240 degrees Celsius in step a.
3. The method of claim 1 , wherein the organic solvent is selected from the group consisting of dimethylformamide, dimethyl sulfoxide, diethylformamide, N-methyl-2-pyrrolidone tetrahydrofuran, acetonitrile, and alcohols in step b.
4. The method of claim 1 , wherein dissolving trans-cinnamic acid in the organic solvent comprises heating the trans-cinnamic acid in the organic solvent.
5. The method of claim 1 , wherein dissolving trans-cinnamic acid in the organic solvent comprises sonicating the trans-cinnamic acid in the organic solvent.
6. The method of claim 1 , further comprising filtering the trans-cinnamic acid solution between steps b and c to avoid formation of α-trans-cinnamic acid.
7. The method of claim 1 , wherein the poor solvent is selected from the group consisting of ice water, brine, hexane, cyclohexane, pentane, heptane, and petroleum ether.
8. The method of claim 1 , wherein the poor solvent has a temperature lower than 15 degrees Celsius.
9. The method of claim 1 , wherein mixing the trans-cinnamic acid solution into the poor solvent in step c comprises adding the solution dropwise to the ice water and stirring.
10. The method of claim 1 , wherein mixing the trans-cinnamic acid solution into the poor solvent in step c comprises adding the solution directly to the poor solvent.
11. The method of claim 1 , wherein mixing the trans-cinnamic acid solution into the poor solvent comprises injection with an injection device or a dropping device.
12. The method of claim 1 , wherein mixing the trans-cinnamic acid solution into the poor solvent avoids formation of α-trans-cinnamic acid.
13. The method of claim 1 , further comprising precipitating the β-trans-cinnamic acid in crystal form as part of step c.
14. The method of claim 1 , wherein irradiating the slurry as part of step d comprises applying a UV irritation source.
15. The method of claim 1 , irradiating the slurry as part of step d is done for at least 15 minutes.
16. The method of claim 14 , wherein the UV irritation source is selected from the group consisting of blacklight, germicidal lamp, floodlight, mercury vapor lamp, LED, and sunlight.
17. The method of claim 1 , further comprising cleaning the cis-cyclobutrane-1,2-dicarboxylic acid.
18. The method of claim 1 , wherein the trans-cinnamic acid has head-to-head packing.
19. The method of claim 1 , wherein the cis-cyclobutrane-1,2-dicarboxylic acid is recovered as trans-cinnamic acid after heating above 250 degree Celsius.