Processing

Please wait...

Settings

Settings

Goto Application

1. WO2020117519 - METHOD OF MAKING CYCLOBUTANE-1, 2-DIACIDS DEGRADABLE BUILDING BLOCKS FOR MATERIALS

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

1. A method of making a s-cyclobutane-l,2-dicarboxylic acid monomer comprises: a. melting trans- cinnamic acid;

b. dissolving //vmv-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 /-/ran.v-cinnamic acid and form m-cyclobutane- 1 ,2-dicarboxyl ic 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, /V-methyl-2-pyrrolidone tetrahydrofuran, acetonitrile, and alcohols in step b.

4. The method of claim 1, wherein dissolving /ran.v-cinnamic acid in the organic solvent comprises heating the trans- cinnamic acid in the organic solvent.

5. The method of claim 1, wherein dissolving /ran.v-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 a-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 a-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 s-cyclobutrane-1,2-dicarboxylic acid.

18. The method of claim 1, wherein the //v/n.v-cinnamic acid has head-to-head packing.

19. The method of claim 1, wherein the m-cyclobutrane- 1 ,2-dicarboxylic acid is recovered as trans- cinnamic acid after heating above 250 degree Celsius.