Polyamides, and methods of producing thereof
Provided are methods of producing polyamides from beta-lactones. The polyamides include bio-based polyamides that may be obtained, either in part or completely, from renewable sources.
1. A method of producing a polymer, comprising:
contacting an alkylene oxide and carbon monoxide to form a compound of formula (1);
combining the compound of formula (1) with a nitrogen-containing compound of formula (2) under aqueous conditions to produce a compound of formula (3-a), wherein:
the compound formula (1) is
wherein each R 1a , R 1b , R 1c and R 1d is independently H or alkyl,
the nitrogen-containing compound of formula (2) is R 2 —NH 2 , wherein R 2 is H or alkyl, and
combining the compound of formula (3-a) with a weak base to produce the polymer, wherein:
the compound of formula (3-a) is
wherein each R 1a , R 1b , R 1c , R 1d and R 2 is independently H or alkyl, and
the polymer comprises repeating units of formula
or a salt thereof wherein each R 1a , R 1b , R 1c , R 1d and R 2 are as defined above for formula (3-a).
2. The method of claim 1 , further comprising isolating the compound of formula (3-a) prior to combining with the weak base to produce the polymer.
3. The method of claim 1 , wherein the nitrogen-containing compound of formula (2) is aqueous ammonia.
4. The method of claim 1 , wherein the weak base has a pKb value between 7.2 and 10.4.
5. The method of claim 1 , wherein the weak base is a carbonate salt or a bicarbonate salt, or a combination thereof.
6. The method of claim 1 , wherein the weak base is sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, sodium bicarbonate, potassium bicarbonate, calcium bicarbonate, or magnesium bicarbonate or any combinations thereof.
7. The method of claim 1 , wherein the polymer is produced from the compound of formula (3-a) at a temperature of at least 70° C.
8. The method of claim 1 , wherein the polymer is produced from the compound of formula (3-a) at a temperature between 80° C. to 160° C.
9. The method of claim 1 , wherein R 1a is H.
10. The method of claim 1 , wherein R 1a is alkyl.
11. The method of claim 10 , wherein R 1a is C 1-6 alkyl.
12. The method of claim 10 , wherein R 1a is methyl, ethyl or propyl.
13. The method of claim 1 , wherein R 1b is H.
14. The method of claim 1 , wherein R 1b is alkyl.
15. The method of claim 14 , wherein R 1b is C 1-6 alkyl.
16. The method of claim 14 , wherein R 1b is methyl, ethyl or propyl.
17. The method of claim 1 , wherein R 1c is H.
18. The method of claim 1 , wherein R 1c is alkyl.
19. The method of claim 18 , wherein R 1c is C 1-6 alkyl.
20. The method of claim 18 , wherein R 1c is methyl, ethyl or propyl.
21. The method of claim 1 , wherein R 1d is H.
22. The method of claim 1 , wherein R 1d is alkyl.
23. The method of claim 22 , wherein R 1d is C 1-6 alkyl.
24. The method of claim 22 , wherein R 1d is methyl, ethyl or propyl.
25. The method of claim 1 , wherein R 2 is H.
26. The method of claim 1 , wherein R 2 is alkyl.
27. The method of claim 26 , wherein R 2 is C 1-6 alkyl.
28. The method of claim 26 , wherein R 2 is methyl, ethyl, propyl or butyl.
29. The method of claim 1 , wherein the polymer has a biocontent of at least 10%.
30. The method of claim 1 , wherein the compound of formula (1) is obtained from renewable feedstock.
31. The method of claim 1 , wherein the compound of formula (2) is obtained from renewable feedstock.
32. The method of claim 1 , wherein the polymer is converted from the compound of formula (3-a) in an amount of about 70 percent.
33. The method of claim 1 , wherein the polymer is produced from the compound of formula (3-a) after heating to a temperature of about 180 degrees Celsius, and wherein the polymer is produced from the compound of formula (3-a) after 5 hours.
34. The method of claim 1 , wherein the polymer is produced under a gas stream comprising nitrogen.
35. The method of claim 1 , wherein the alkylene oxide comprises ethylene oxide.