Systems and processes for polymer production

• US 10,683,390 B2
• Filed: 02/12/2016
• Issued: 06/16/2020
• Est. Priority Date: 02/13/2015
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Farmer, Jay J., Galebach, Peter, Sherry, Kyle, Sookraj, Sadesh H.
• Primary Examiner(s): Truong, Duc
• Application Number:
  US15/550,161
• Publication Number:
  US 20180094100A1
• Time in Patent Office: 1,586 Days
• Field of Search: 528355
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 57/04 Acrylic acid; Methacrylic acid
• CPC Class Codes: C08F 120/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 4/30 Inorganic compounds
• CPC Class Codes: C08G 2650/04 End-capping
• CPC Class Codes: C08G 63/06 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 63/08 Lactones or lactides

Abstract

Disclosed are compositions, systems and methods related to a polypropiolactone composition comprising polypropiolactone polymers. Such polymers include polypropiolactone chains of Formula (I): [Formula should be inserted here] where n is an integer from 10 to about 1,000 and Y is either —H or a cation.

Claims

1. A method for producing a polypropiolactone composition, comprising:

combining beta propiolactone and at least one salt of a compound of Formula (III) to produce the polypropiolactone composition, wherein;

the compound of Formula (III) has the structure;

2. The method of claim 1, wherein the polypropiolactone polymers, or salts thereof, independently have a structure of Formula (I):

3. The method of claim 1, wherein the beta propiolactone is combined with the at least one salt of the compound of Formula (III) at a temperature greater than 50°

C.

4. The method of claim 3, wherein the temperature is in the range from 140°

C. to 200°

C.

5. The method of claim 1, wherein at least 95 wt % of the polypropiolactone composition comprises polypropiolactone polymers, or salts thereof, having the acrylate end group.

6. The method of claim 2, wherein at least 90 wt % of the polypropiolactone composition comprises polypropiolactone polymers, or salts thereof, having the structure of Formula (I).

7. The method of claim 2, wherein the polypropiolactone composition has a polydispersity index (PDI) less than 1.7.

8. The method of claim 1, wherein p is 0.

9. A method of producing a superabsorbent polymer, comprising:

converting a polypropiolactone composition of claim 1 to produce acrylic acid, and

polymerizing the acrylic acid blended with sodium hydroxide in the presence of a radical initiator to produce the superabsorbent polymer.

10. A superabsorbent polymer produced according to the method of claim 9.

11. The method of claim 1, wherein the combining of beta propiolactone and the at least one salt of the compound of Formula (III) produces a chain transfer agent, wherein the chain transfer agent is at least one salt independently comprising an acrylate end group having the structure

12. The method of claim 11, wherein the chain transfer agent is at least one salt independently further comprising:

a chain comprising one or more units having the structure

13. The method of claim 8, wherein the at least one salt of the compound of Formula (III) comprises a cation selected from the group consisting of ammonium, protonated amine, and iminium.

14. The method of claim 13, wherein the ratio of the beta propiolactone to the at least one salt of the compound of Formula (III) is between 1:

9,000 and 1;

14,500.

15. The method of claim 1, wherein the beta propiolactone and the at least one salt of the compound of Formula (III) are further combined with a compound of Formula (III).